r/ChastityStories • • Dec 23 '23

Before posting your RL "stories" - READ THIS POST NSFW

92 Upvotes

We are all glad that more and more people are incorporating chastity into their lifestyle. However, this subreddit is not to be used as a journal entry for your chastity journey.

If you are looking to get feedback or discuss a short experience you had w/ chastity please take it to another sub like /r/chastityjourney or others.

What We're Looking For:

  • Depth and Length: We encourage stories that offer more than a quick glance. Think of narratives with a beginning, middle, and end, regardless of whether they're fiction or based on real-life events.
  • Engaging Narratives: Share stories that pull readers into a journey, whether it's through detailed character development, intriguing plotlines, or insightful personal experiences.

What To Avoid:

  • Brief Anecdotes/Journal Entries: To maintain the quality of content, we kindly ask that shorter, journal-type entries and brief personal anecdotes be shared elsewhere. Our platform thrives on more developed storytelling.

Why This Matters:

  • Quality Engagement: Longer, thoughtfully crafted stories foster deeper discussions and a more engaged community.
  • Diverse Storytelling: While we appreciate the simplicity of short posts, the essence of our community lies in stories that are told with attention to detail and narrative structure.

r/ChastityStories • • Jul 24 '22

Story Requests NSFW

90 Upvotes

If you have a request for a story, have a look in here, someone may have already made the same request.

If your request is not already in here, feel free to make a comment asking.


r/ChastityStories • • 18h ago

M Chaste,F Keyholder Sorority Rush - Part 5 NSFW

111 Upvotes

Noah awoke to an insistent pounding on his door. His head was foggy from too much beer and too little sleep. He had stayed up late into the night digging through every Cyberlok forum he could find on the internet. He had to find a way to get out of the cage. But his findings had been damning. Apparently, it had been proven time and time again, even in the court of law in multiple instances, that when a person clicked through the ‘terms and conditions’ on the Cyberlok app and put the cage on, they essentially consented to everything that happens to their chastity sentence going forward.

He stumbled out of bed and groped for the pair of sweatpants he normally slept in. He was still naked from the night before when he had stripped down with the goal of releasing all his pent-up horniness, only to have his dreams dashed in the cruelest imaginable way. Pulling them on, he went to see who was still pounding on his door. Checking the peephole this time, he really didn’t want to talk to anyone at the moment, he saw that it was Hannah who had woken him up. She looked even worse than he felt. Her hair a rat’s nest, her shirt unchanged from the night before, although she had traded in her little skirt for some leggings, and her makeup looked like she had been crying.

Opening the door, he caught her with her hand raised and poised to knock again. Not knowing what he wanted to say to her, he was in this mess because of her after all, he simply turned and walked back into his room, leaving the door ajar. He scooped up a t-shirt on his way back to his bed and pulled it on.

He heard the door close behind him as he sat on his bed, his eyes focused on the floor. An uncomfortable silence spread between them until Hannah finally broke it.

“I didn’t know what was going to happen, I swear. I’m so sorry. You have to believe me. You believe me, right? I’d never lie to you like that,” Hannah pled, her voice cracking as she tried to hold back her swirling emotions.

“I don’t know what I believe,” Noah mumbled, still refusing to look at Hannah. “You were so nice and convincing when you came to me yesterday and begged for my help. I don’t know if you’re that good of an actor, or if they tricked you too. I don’t know what to think.”

“Noah. No. I would never lie to you and trick you like that. You’re my best friend here, joining a sorority isn’t worth betraying you,” she said, tears now streaming freely down her cheeks. “I know, I’ll go tell them I quit and they’ll have to let you out then,” she added, sounding like she had just stumbled upon the solution.

Before Noah could respond to her idealistic idea, his phone vibrated loudly on the wooden bedside table it was resting on. Picking it up to check what the notification was, his heart plummeted.

Message from Keyholder SneakyStella: “Be at Pi Delta at 1 PM. And bring Hannah with you, she is ignoring my messages. Don’t be late.”

The whole time he was staring at the message from his jailor, Hannah had kept rambling on about how she could find a new sorority next semester. And how Stella would have to let him out once she informed her that she was quitting.

Her anxiety induced, rapid-fire words were cut off when Noah held his phone out for her to take.

She stared at the phone for a long moment, her newfound energy completely extinguished. After tapping around on the screen a few times she resignedly handed it back to him.

“29 days,” she said, her voice dead of all emotions. “I’m so sorry. I can’t believe Riley allowed this. Stella is a little crazy and over the top, but I can’t believe Riley allowed her to do this. And that she even participated in it too.”

Noah had no idea who Riley was or whatever else Hannah was talking about. But over the few minutes Hannah had been in his room he had decided one thing. Hannah had no knowledge of the trap she had walked him into. He had known her for too long, and she was too kind and her emotions too raw to be believably faked. Everything pointed to her being duped—the same as him.

“I guess we just have to go and talk to Stella in person and convince her to let you out. We should probably hurry; it’s almost noon already. Do you want to grab lunch before we go?” It was remarkable how fast she was able to compartmentalize his plight and speak of normal things like food. All he could think about was the cage. He could feel it pressing down on his penis every second since he had woken up.

“I guess. Let me take a quick shower. I feel gross after last night,” he mumbled as he went to collect some clean clothes from his dresser. “Fuck. How am I supposed to clean myself? Can this thing even get wet?”

“Umm, I remember reading that all Cyberloks are waterproof in the brochure it came with. They are designed for near permanent wear if the keyholder desires it,” Hannah said awkwardly.

Great, he thought, this psycho chick can keep my dick locked away for the rest of my life if she wants and there’s nothing I can do about it.

He needn’t have worried about getting the cage wet. Imperceptible holes allowed water to flow in and out of the cage freely. In no time he was washed, dried and dressed and as ready as he could be to face the nightmare of a day he had before him. With a final glance at his sentence, he followed Hannah out into the world in a way that could become his new normal. Locked and hopelessly horny.

Remaining time: 29 days 11 hours 57 minutes 19 seconds

***

Noah dragged Hannah along as he rushed her towards the Pi Delta house, she had insisted on stopping at her dorm to freshen up after they ate. She had somehow convinced herself that by quitting the sorority he would be immediately released. He doubted it would be that simple. So he refused to be late. He saw what had happened to Sofia last night when she was late and Stella held way more power over him than she did over any of the pledges.

They arrived at the house slightly out of breath but with ten minutes to spare.

“So do we knock or can we just walk right in now that you’re a full-time member,” he said. Even though he believed Hannah when she said she’d been tricked, he couldn’t help a little venom from leaking into his words. He was the one still paying the price for her actions after all.

“We can just walk in,” Hannah said, unable to hide the hurt in her voice. Noah felt a stab of guilt at his harsh words. He knew she felt bad about how everything was turning out, but it was tough to keep his emotions bottled up. Masturbating was how he usually let go of any pent-up emotions, but that option was off the table for who knew how long. Maybe forever. He shivered at the thought.

There was no evidence that a party had been held in the sorority house the previous night. The floor was spotless; there were no red solo cups laying around and the house even smelled like it had been freshly cleaned. A few girls looked up from one of the handful of couches that now occupied what had been a dance floor just a few hours earlier.

“Leave it to Stella to already be summoning her boy to her,” a gorgeous Indian girl said, causing a ripple of laughter to pass between the other older girls. “Hi, Hannah,” she added with a cheery wave and a genuine smile.

“Hi, guys,” Hannah said with an awkward little wave as she stood beside Noah, still just inside the front door of the house. “Do you, uhh, know where we can find Stella?”

“She’s in her room.” The answer came from a tall, busty blonde who was walking down the grand staircase that was on the far side of the large entrance room. Noah winced as his dick swelled painfully in its prison. The tall blonde was only wearing a black sports bra, spandex shorts and running shoes, like she wanted to turn every head on campus during her run. “Top floor, last door on the left.”

“Good luck,” she added with a sympathetic smile and a pat on his shoulder as she walked by him and out into the warm fall day.

Noah glanced at Hannah, hoping that she would lead the way. He felt too uncomfortable to march across the room full of girls by himself.

Thankfully she understood his look and started walking. “Come on. We better hurry up. Knowing Stella, she’ll probably still claim we’re late unless we are standing before her when the clock strikes one.”

Hannah led the way up the large staircase. Noah did his best not to stare at her leggings clad rear. Both out of respect and to keep his penis from struggling any more than it already was. Once they reached the second floor, they had to travel down a long hallway filled with doors until they came upon a smaller staircase that accessed the upper floors. Up another two flights they went until they emerged in a hallway with only a handful of rooms branching off of it.

“This is where all the senior officers live,” Hannah said under her breath, almost like she was in awe of standing here. “I’ve never been allowed up here before.”

Noah felt more confident striding down the hallway in the lead without a room full of girls watching him. He stopped before the last door on the left, took a deep breath and knocked twice on the door.

The sound of his knock had barely dissipated before he felt a quick vibration from his cage. Pulling out his phone he looked down in shock.

SneakyStella removed 4 days from BestieNoah’s sentence

Remaining time: 25 days 11 hours 4 minutes 31 seconds

Noah’s eyes almost fell out of his skull as the door flew open and he was met with Stella standing proudly before him. She wore nothing but the skimpiest and sexiest light pink lingerie he had ever seen.

“That was lesson one, pet. Do what I say and you’ll be rewarded. Too bad you didn’t decide to show up thirty minutes early instead of just four.”


r/ChastityStories • • 16h ago

M Chaste,M Keyholder Locked For the Prince of Blanffe - Chapter 18 - A Night in Milan. NSFW

7 Upvotes

For all my other stories and other parts of this one:

https://www.reddit.com/user/Chastity_Wannabe/comments/1k9n4xt/story_index_file/

Thanks for all the love, everyone!

I created a Patreon and it already has a few exclusive stories that will only be here in a month: Maybe give it a look??? It would help to be able to keep writing stories!

******************************************************************

On their third day in Milan, the three boys had already done every touristy activity they wanted to, they had even watched an AC Milan match at San Siro, where Peyton was announced as a guest of honor. Boise was quickly going crazy, seeing sex in everything, but, as they agreed, he didn’t ask to have the black carbon tube removed from his body a single time… He quickly found out that a deodorant tube up his ass wouldn’t give him an orgasm, but he still felt some relief with the constant ooze of pre-cum coming off his tip, so he started doing it every night.

On the third night, after a GREAT day outside touristing, they got back to their rented apartment and Peyton ordered lots of food and wine for them to relax… As the three boys jumped on the sofa, glasses in their hands, it was time for them to chat and unwind after a long but great day.

— Out of curiosity, what are our plans for tomorrow? — Boise asked. — We have two more days here, right? But we’ve already done everything.
— Tomorrow we’re going to the Galeria Vittorio Emanuele to do some shopping. — Marty explained. — Get the wardrobes a little bigger.
— Ohh, nice! Can i go with you? — Boise asked. — I absolutely don’t have money to buy anything, but it would be nice to see the kinds of stuff you guys wear.
— Dude, we’re throwing your luggage in the garbage and buying everything new for you! — Marty replied, smiling. — Well, not actually throwing stuff away, but you get my point.
— You can’t do that to me! — Boise replied nervously. — I can’t abuse of you guys! Or of the Crown. My dad would kill me.
— I actually don’t remember having asked your opinion.— Peyton replied jokingly.
— You guys are getting me too spoiled. — Boise lamented.
— Those are just some demonstrations of love. — Peyton said, stretching out to steal a kiss from Marty before going for a new sip of wine. — How’s your caged situation going downstairs?
— Cage check time? — Marty asked joyfully.
— I’m desperate. — Boise admitted. He stood up, pulled his shorts and underwear down and revealed his locked, leaking dick to the Prince and the Duke. — Seriously, make sure none of you EVER ends up in one of those!
— Maybe tiny dicks that don’t work properly should always stay like that… — Peyton said, teasing Boise. — To keep them from having any accidents.
— Don’t even joke about it. I’m so desperate that when i’m free, i’ll just touch it and it’s gonna keep exploding for a month. — Boise replied.
— I agree with Pey… — Marty said, inspecting the cage. — I like it more when you’re like this… Less risk of creaming yourself while you suck our feet!
— Can i lick your feet now? — Boise asked, not even blushing.
— Get naked! — Marty replied.

Boise quickly got naked, and then, as Peyton instructed him, he got on his knees and removed both boys’ socks with his mouth… None of them ever got smelly, but after a whole day of walking, there was a bit of sweat, and aparently that was enough to get Boise crazy. Boise had no idea, but under his black shorts, Marty was also leaking inside his own cage… At least he had Payton as a nut extractor for later that night.

As Boise was sucking both boys’ feet and toes, the two boys started getting more and more excited, using their hands to explore their bodies, kissing each other, and certainly being more explicit than they would be in any other public situation… Eventually, they grabbed Boise and put the boy in the sofa with them, so Peyton started kissing and licking the boy’s neck, even pinching the boy’s nipples… Marty got between Boise’s legs, and, wanting to make the boy go crazy, he started sucking on the boy’s trapped balls. Boise couldn’t stop moaning, he was sweating, desperate, but nothing happened at all! He just couldn’t cum.

— Now it’s time for you to go to bed, Boise! — Peyton said, desperate to go fuck his boyfriend in their suite.
— You’re going to leave me like this? — Boise asked, shameless.
— Were you under the impression i was gonna let you nut? — Peyton asked, confused.
— Do something for me, please! Anything. — Boise begged. 
— What do you want that doesn't involve you having orgasms? — Peyton asked, laughing.
— Can i watch… You two… Doing it? — Boise asked. — The sex, i mean.
— Not today… — Peyton replied in a way that left Marty just as confused as Boise.
— Maybe let me see your guys's dicks? — Boise tried his luck.
— What do i get if i let you see mine? — Peyton asked, still laughing.
— Anything you guys want! — Boise replied, watching the couple turning to each other with naughty looks.
— You'll have to stay naked the entire time you're at the apartment with us! — Marty replied. — Until the end of the trip.
— Deal! — Boise replied a bit too quick, a bit too loud. — I'm already like this, i just need to keep going!
— So come here, really close! — Peyton said, pointing to his own lap. — On your knees to your majesty!
— Yes Sir, Your Highness! — Boise replied, getting on his knees between the prince's legs.
— Marty, would you open the button of my pants? — Peyton asked.
— Ohh, with all the pleasure in the world, my love! — Marty replied, and then the couple kissed once more!

Boise stood still, squeezing both his balls and alternate nipples, looking desperate at the kissing couple. One of Marty's hands went to Peyton's crotch, and, without looking, he opened the button with ease. Marty then forced his hand inside Peyton's underwear, pulling that HUGE dick from inside. It was the biggest cock Boise had ever seen in his life. He just kept staring, in shock, squeezing his balls with more strength by the second, desperate to cum.

— This looks just perfect! — Boise said in awe. — The royal blood must make some kind of difference.
— And Peyton knows how to use it like a master. Like it's a form of art. — Marty said, jerking his boyfriend's cock a little.
— Can i touch it? — Boise asked. — I'll do anything you guys want in return.
— My dick's only Marty's. I'm sorry, Boise. — Peyton replied, for as much as he wanted to let the boy touch the Royal Meat.
— Ohh, okay, so can i just admire it a little longer? — Boise asked and both boys LOVED him for it.
— How about i jerk off my man? — Marty offered, teasing Boise. — And make sure his milk gets all over your face?
— Fuck, am i dreaming? — Boise replied, feeling his tiny nub of a dick twitching inside his micro cage. — What will it cost me?
— I just hope you're prepared to repeat all of this when we go to Australia on the next vacation. — Peyton replied, winking at the boy.

Boise wasn't sure if he understood it or not, but he agreed while beaming. Peyton's smile was even bigger as Marty's hand closed around his bat and then began to slowly jerk him off. Boise was watching it all feeling desperate, wanting to touch that cock, but only admiring it while twisting his own nipples and balls. He didn't have access to his own boy toy, but he could feel the constant flow of pre-cum dripping from the cage's tip.

Boise had no idea it was possible for someone to last that long but also to make him suffer longer, Marty was taking his time in jerking his boyfriend's pole… It was only 10 minutes after Marty started that the boy sped up. In the 12-minute mark, Peyton let his first moan escape his lips, making Boise moan with him.

Marty could, at the same time, feel his boyfriend's dick pulsating in his hand, his own dick trapped inside his cage, dripping pre-cum, but also, most importantly, see what Boise was doing with his trapped dick. When Peyton said “i'm gonna cum”, Marty pointed that dick's tip to Boise's face and then started only jerking the tip off. Peyton began producing copious amounts of his seed, and every single blast was landing on Boise's face. The boy was stretching his tongue out as much as he could, loving every moment of all that was happening to him.

— Thanks! — Boise said, finally giving a rest to his nipples in order to use his fingers to get all that warm seed and put it inside his mouth. — That's the best thing that ever happened to me.
— Stand up, let me feel your testies. — Peyton replied and Boise obeyed, letting the prince squeeze his full balls for a few moments. — Fuck, there are exploding.
— Let me feel them! — Marty asked, also squeezing the boy's balls. — They really are… And locked, as they should.
— Thank you so much! — Boise replied, his whole body desperate for sex.
— Now… Go to your room, Boise. — Marty said, and, without complaints, Boise stood up and left the room. — Let's go to ours, baby?
— Let's go… That was wonderful! — Peyton replied, going for an extra kiss. — Do you need an orgasm?
— For the love of God! — Marty replied, beaming, leaning in for a deeper kiss. — Take off me what i can't extract alone.
— Leave it to me! — Peyton replied, picking Marty up in his arms and taking his boyfriend to their room. — You look SO PERFECT in this cage!
— I know! And he's all yours! — Marty replied. — You… Know what it the next thing Boise is gonna ask, right?
— See yours? — Peyton asked. — I'm gonna tell him your dick is only for me and that's it!
— Okay! It works for me. — Marty replied. — And what you want from Boise?
— I'd love to keep him locked up until we graduate. — Peyton said, laughing.
— Me too. — Marty agreed. — Let's make that happen, okay?
— Deal, baby! — Peyton said, smiling.

As Peyton got Marty naked in bed, he decided to take advantage of the fact that he just nutted and wasn't horny or hard yet, so he did the complete service for his boyfriend. The Prince sucked on the Duke's ears, then the mouth, followed by the neck and nipples. He started going down to the stomach, even forcing his tongue up the Duke's belly button, and just then he finally arrived at the cage. 

Peyton sucked and licked on both sides of the boy's crotch, then put both testicles inside his mouth, even humming to make them tingle. At the end, he spared a good five minutes to just blow the cage up, his tongue going up the pee hole as much as he could, licking that salty tip, his lips brushing the bits of tip that were escaping the breathing holes.

Finally, Peyton spread Marty's legs, forcing the Duke's ass up, and, with him already at full mast, the Prince allowed himself inside his boyfriend's hole, finding his prostate in seconds. Peyton focused on massaging it with all his might, his tip brushing that little bump with care and love, with a lot of precision.

He was making Marty start to moan in just a little bit, and as his loving Duke got hornier and hornier, his body started glitching, twitching, and all that arousal was desperate to escape through his dick. After 10 long minutes of lovemaking, Marty started screaming, and, as he did it, rope after rope of cum started erupting from his cage's tip, his dick twitching and throbbing so much cum was landing everywhere on that bed. 

As Marty's orgasm finally faded after minutes of the boy riding the pleasure wave, it was Peyton's turn to have his fun. He not only started thrusting it much faster, but he was also using his whole length to fuck the boy he loved the most in the world. It just took him a few minutes, but, with Marty helping by squeezing his hole, Peyton let out a guttural, powerful moan and let out all of his juices inside Marty's back entrance.

Even with both boys feeling exhausted, they got up from the bed and went for a quick shower. Soon after, they were back in bed, naked, clean, spooning like always. Peyton hugged his boyfriend, back touching chest, Peyton's dick finding his housing between Marty's butt cheeks. After a kiss on the back of the neck, Peyton held Marty's cage in his hand and soon both boys were sleeping, both feeling in love.

In the other room, Boise was stretched in bed, a metal tube of deodorant up his hole, and since he had the last drops of Prince Peyton's seed in his right hand, he was looking at it, appreciating it, and treasuring it like it was the most important thing he ever touched. He even took a picture of the Prince's seed so he could remember forever. Boise knew the rest of his vacations would be REALLY LONG, and… Did he just agreed on going on a state visit to Australia with the KING???


r/ChastityStories • • 1d ago

M Chaste Family visit (part 2) NSFW

63 Upvotes

This chapter ended up a bit shorter than the previous one, unfortunately. I hope you'll still enjoy it.

----

The knocking on the door should have woken me up easily if it wasn't for my morning wood already beating it to it. "Wake up, boys! You've got one hour to get ready!" I adjusted my cage and grabbed my phone, looking for something to distract me from the futile attempts of my cock trying to break out. 

"I slept great, how about you?" Jack asked. 

"I slept oke, the first night in the cage is always a bit rough" I replied.

"You better get used to it then!" Jack said with a wink before pulling away the covers and revealing his freely throbbing morning wood. "Seems like the problem from last night still isn't fixed, mind helping me out quickly" He said. 

"I don't think we have time right now, we've got to be ready in 50 minutes now. 

"You better come over and start working on it then." Jack sat on the edge of the bed again, like last night and I got back in the same position. This time I focused extra on stimulating him as much as possible, so he would come quickly. 

"Ooh, that feels good. And remember, you're still not allowed to waste anything. I want to give you a proper breakfast!"

Jack was much quieter and didn't moan as much as last night, probably now being a bit more aware of the others in the house hearing us. It did make it harder for me to know what he liked and how close he was. I continued sucking and wasn't prepared yet when he came unexpectedly. I had to react fast to swallow everything. His load was just as big as last night. "Fuck that was good, I could get used to this every morning. I am really going to have to find some submissive twink at home." Jack said. I got up and wiped my mouth clean. 

"I'm showering first." I said, quickly grabbing a fresh pair of underwear and making my way towards the shower. It felt very refreshing and I did my best to clean my caged cock from all the dried precum. After a few minutes, I was ready and only had to dry myself off and get dressed. When I got downstairs, I had about 30 minutes left for breakfast, which was plenty of time for me. Jack followed another 15 minutes later. 

My parents had planned a day to the zoo today and we were to leave early because it was a two hour drive and because they wanted enough time to spend there. I wasn't looking forward to it a lot, I felt like zoos were more for young children and not for a group of adults. The situation with Jack had made everything even more complicated.

Right on schedule, everyone was ready to go and we split up over the two cars. Me, Jack, my father and my uncle took our car and the rest went in the other car.

As I was putting on my shoes my sister walked over to me and whispered in my ear. "Can you guys be a bit more quiet in your room next time? It's great that you get along so well, but your talking kept us awake." She sounded as annoyed as she always sounded. "Yeah sorry, we'll keep it down next time" I said. The hairs on my neck stood up straight and I wondered what they might have heard. Jack wasn't particularly quiet in his talking and moaning last night and I worried that they might have heard what exactly was going on. Great, another thing to worry about I thought to myself. 

The drive to the zoo was quite uneventful. We talked about generic stuff mostly. At the zoo, Jack couldn't keep himself from whispering some jokes about things being caged towards me. 

"About that topic" I said after the third bad joke about a snake in a cage, "my sister came up to me this morning to complain about how much noise we made last night. Well, I say me but it was mostly you. I don't think she knows what happened, but we've got to be a bit more careful if you don't want to out yourself too."

Jack seemed not very interested in what I said and waved it off with a simple "I'll try to think about it" and we continued with our day. The rest of the day was uneventful. I had some experience with being caged and could deal with it quite well during the day. Yes, it took some extra effort to hide it under my clothes and toilet visits took slightly longer because I had to sit to pee, but overall it didn't bother me too much.

It was already late in the evening when we got home again. My parents and my aunt and uncle went to bed not long after coming home. Jack and I were also tired and decided to go to my room. Jack was already upstairs when my sister stopped me in the hallway downstairs. "I don't know what you guys were doing last night, but you really need to be quieter." I got the feeling my sister had a much clearer idea about what happened last night than I thought, or hoped, she had. "Sorry sis, but honestly, it's mostly on Jack, I told him to quiet down several times." She gave me a look of disbelief before letting me go.

Jack and I were much too tired from the day to stay awake longer than necessary and we both went to sleep not long after getting in bed.

Before Jack turned around to sleep, he said to me: "I want you to have breakfast in bed tomorrow, if you know what I mean." "Fine." I said with a sigh before turning around myself.

The next morning, we were again woken up by knocking on the door. "Hurry up boys, get ready quickly and Jack pack your stuff, you are going back today." We both looked at each other a bit puzzeled, I thought they would stay at least one more night, but apparently plans had changed.

"Well, you heard what your mother said, you'd better hurry up." Jack said while looking at his groin. His cock was obviously already fully erect and clearly visible through the bedsheets. I contemplated complaining, but figured it would only cost more time and probably not get me anywhere. Barely awake, I got up from my bed and moved over to Jack's. He folded away his bedsheets and spread his legs. He gestured for me to take place in between his legs. I was about to step on the bed when Jack told me to take off my underwear. "I wanna see you strain in your cage". I obliged and got into place. The position was quite awkward, I had to get on my knees and elbows to get my head in the right position. My ass was pointing high up in the air while I took his cock in my mouth. I immediately got to work and used my experience from the previous two blowjobs to quickly get Jack to a climax. It took only a minute before I could feel Jack tensing up. He remaind remarkably quiet this time, only breaking the silence now to let me know he was close. Just seconds later Jack filled my mouth again with his hot seed and I had to swallow several times to not spill anything. 

"Fuck that was good, I'm going to miss this so much after today." We both quickly got dressed after and I helped Jack to pack his suitcase. 

When we got downstairs and took a seat at the breakfast table, my uncle was already apologizing. "I'm sorry we have to go back a day early so suddenly, but something has gone wrong at my work and they really need me to fix it today. We are leaving in 30 minutes." We quickly got to eating some breakfast and continued chatting about the situation at my uncle's work. He kept apologizing and me and my parents kept telling him to stop. While eating I felt a sense of relief on one hand, it meant the weird thing with Jack would come to an end and he would have to give me the keys back. The thought of finally jacking off already made me strain and I couldn't wait for the first opportunity to do so. On the other hand, I also felt a little bit sad. As wrong as it was to have this relation with my nephew, the past two days were incredibly hot. I hated him finding my secret out and blackmailing me into locking myself up and giving him the keys, but I absolutely loved being locked up by someone else and not having access to the keys. The bj's also were humiliating but very hot at the same time. My thoughts drifted back to those moments and I could almost taste Jack's seed again.

"Are you almost ready Ron?" My thoughts were interrupted by my mother. I had slowed down eating while thinking and the others had already finished eating. "Yes, almost ready!" I said and I quickly finished my sandwich. 

My aunt had already finished packing the car by now and the Roseberry's were ready to leave again. I gave them all a hug one by one and Jack was the last one. Jack pressed his body a bit harder into me than the others did and I could feel his leg pressing into my crotch. A subtle reminder to our little situationship. Shit, he still had the keys. During day to day life, I often wouldn't even notice the cage when I'm wearing it. "It was good to see you again", I said to him, “but aren't we forgetting something?" I whispered.

"We'll see each other again in October, right? I'm sure you can manage until then." 

"No idiot, unless you want to visit me in hospital with an infection, I need to take the cage off once a week for cleaning." I whispered slightly angrily to Jack.

"Loads of people online seem to do fine without unlocking, so why can't you?" Jack really seemed to live in a fantasy world. I rolled my eyes and explained to him that most people take it off regularly for cleaning and that those who said they don't are mostly liars. I saw Jack sigh and think and didn't like it a bit. "I have an idea." He finally said after a few seconds. "Until the next time" he said with a smile and he gave me a final hug and then walked away. I felt my stomach drop as Jack walked towards my sister and whispered something into her ear. He then pulled the keys from his pocket and handed them over to her and whispered some more to her. I felt my head starting to spin. This couldn't be real, right? What would my sister think of it, knowing her it couldn't be any good. My only hope was that she was either not interested or so repulsed by it that she would hand me the keys back straight away. She looked at Jack, then to the keys and then looked towards me. She smiled and pocketed the keys.

End of part 2.


r/ChastityStories • • 1d ago

M Chaste,M Keyholder The White Champion’s Cage, chapter 9 [m/m, interracial, bnwo, slow-burn] NSFW

8 Upvotes

Summary: Jett's urges are spinning out of control. His cravings push him to a dark place - literally. What he sees there might be what the future has in store for him.

Keywords: BNWO, interracial, chastity, humiliation, straight to gay, slow-burn, psychological, athletics

Disclaimer: English is not my first language, so I rely on AI assistance to polish the text.

Chapter 9: Fresh Meat After Dark

Day 18

The headlights swept across Jett Whitaker’s windshield like twin searchlights, freezing him in place behind the wheel. The sudden glare turned the inside of his car into a white void for half a second. When the lights passed, the world outside snapped back into focus: Riverbend Park at night.

The park stretched dark under the trees, dense trails and secluded clearings running down toward the river. By day it was just another public park near the college. At this hour it felt abandoned and seedy—the kind of place people came for things they didn’t want anyone to know about.

A few other cars were parked in the lot, windows dark, engines silent. Jett sat there, hands still gripping the steering wheel, breathing shallow. The trails leading deeper into the wooded area looked like black tunnels. Fuck, this is insane, he thought. What the hell am I doing, man?

***

It had started two days ago, on Monday, after Jett had sucked off Jamal, the Doctor’s assistant in the janitor’s closet. After that, the “relief package” — a big black realistic dildo — only reinforced his anal cravings. On Tuesday, his mind had become a haze of horniness.

By Wednesday Jett threw himself into training with almost manic energy, trying to outrun the ache that had settled deep in his bones.

The team’s weight room was loud with the clang of iron and the grunts of teammates pushing their limits, but Jett’s focus kept fracturing. Every time Marcus or Tyrone, the black basketball jocks, stepped up to the bench, Jett’s eyes drifted toward them. Tyrone, tall and wiry, lay back on the bench. Jett pretended to adjust his own form, but his gaze kept sliding to the heavy outline in those shorts. Marcus was no better: broader, more muscular, his shorts tenting slightly as he spotted Tyrone, the bulge shifting with every movement.

As Tyrone finished his set and sat up, he locked eyes with Jett. The usual intensity in his face sharpened. Marcus followed his gaze; the easy laugh that had been on his face a second earlier was gone, one eyebrow raised. Shit. They saw me staring. They fucking know. He was about to mutter some lame excuse when Gabe Mendoza burst into the weight room, the younger teammate’s loud voice cutting through the tension like a lifeline.

“Whitaker! Bro, you have to hear this,” Gabe said, grabbing Jett’s arm and pulling him out of the weight room to the hallway. Gabe’s eyes were bright with excitement.

“Bro, I'm like actually in the program now. Shit’s fucking insane, man. The cage? Yeah it’s weird as hell at first… but you just gotta trust the process, right?”

Jett just nodded while Gabe kept talking.

“It's totally worth it, bro. I mean, look at you and Magnus — you two went from solid to muscle gods in weeks.” Gabe’s hands gestured wildly, his light olive face flushed with pride.

Jett forced a tight smile and mumbled something noncommittal about being happy for his teammate.

***

Jett had cornered Magnus in the far corner of the locker room after practice, his voice low and hesitant.

“Bro… I gotta ask you a huge favor. Hook me up with Jabari again, man,” he muttered. “Please… tonight if he can swing it.”

Magnus blinked, surprised. Jett rushed on.

“I know how it sounds, alright? But Saturday… it actually helped, man. I just need that kind of relief again so I can keep balling out. That’s all this is. I’m not… I just gotta survive the rest of the program.”

Magnus shook his head slowly.

“Jett… it doesn’t work like that with Jabari, bro.”

“Why not?” Jett pressed.

Magnus sighed. “He won’t see you again until you bring him fresh meat, man. That’s how he rolls. His whole thing is breaking in new guys.”

Jett recoiled. “Fresh meat? What the fuck, Magnus? Was that what you did with me?”

Magnus stayed silent. Jett changed tactics. “Fine. Then tell me about the spot. The one you mentioned at the cafeteria — that relief spot.”

Magnus’ cheeks flushed bright red. “Shit... Did I mention that?”

“Yes, you did,” Jett said forcefully. “Just tell me where the fuck it is, bro. I’m losing my goddamn mind here. I just need something to get me through the next couple weeks. I just need to survive this shit.”

Magnus leaned in closer. “It’s not in Lockridge, bro. It’s over in Riverside — Riverbend Park. The big one by the river, right near the college… that’s where all the down-low dudes go after dark. When a white guy shows up, they know exactly what you’re there for.’”

Jett had pressed him for more details, his craving overriding everything. Magnus had warned him, voice low and serious: “Just… be careful, man. It’s risky. Anyone could see you. People go there for quick, anonymous shit. If someone from school ever spotted you…”

The warning had only made Jett’s cage feel tighter.

***

Now, sitting in the car at the park entrance, Jett took a deep breath. He knew he should start the engine and drive home. Instead of turning the key, he stuck one finger up his ass to make sure that he had douched properly. The finger came out clean. He opened the door and stepped out into the cool night air.

Leaving the parking lot he stepped onto the trail. Occasional lampposts threw short pools of light across the path; between them the dark felt thick. Shadowy figures moved ahead of him. He kept his head down, too afraid to meet anyone’s eyes.

On a wider trail he saw a man in a hoodie leaning against a tree, another figure approaching him slowly. Are they here for the same shit? He stole another glance as he passed — the two men were already moving closer together, voices low. Jett looked away quickly.

Further along, he spotted a lone figure sitting on a bench — older, Black, scrolling on his phone. Jett’s eyes flicked down involuntarily to the man’s lap. The bulge was unmistakable. He forced himself to keep walking.

On a secluded trail he spotted another young white guy — messy ginger hair, a faded rival high-school letterman jacket half-on, sleeves dangling off one shoulder. The redhead moved with the same nervous energy Jett recognized in himself: shoulders slightly hunched, eyes darting around, the way he kept adjusting his pants. Jett knew instantly what it was.

Jett hid behind a tree and watched briefly as the redhead approached the sitting Black man. The sight sent a powerful jolt through Jett’s cage — he felt both jealousy and fear. He turned away.

***

As Jett crept deeper along the shadowed trail, the distant river murmur was the only sound besides his own careful footsteps. Out of the silence, a figure materialized in the deeper darkness between two sturdy oaks — a tall Black man leaning against a tree, hoodie pushed back just enough to catch the faint glow of a lamppost. Lamplight slid across velvet-dark skin and the sharp cut of a strong jaw. A small gold earring winked in one ear; a cross tattoo traced the thick vein running down his powerful forearm. His heavy chocolate-brown cock was already out, the broad head glistening as he stroked it with slow, lazy pulls. The shaft filled his dark fist completely.

Jett froze ten feet away. Their eyes locked. The man’s gaze was dark and . Jett felt a shiver going down his spine, and his cage responded with a twitch.

Without thinking, Jett peeled his hoodie and shirt off in one quick motion, baring the sculpted power of his fair-skinned torso to the cool night air. The Black man’s eyes dragged over every inch of him but he never stopped stroking. His big hand kept working the massive cock in long, unhurried strokes, the heavy balls swinging low beneath.

Jett swallowed hard. He waited for a gesture, a nod, a single word of invitation. Nothing came. The man simply watched him, eyes hungry but unmoving, fist sliding steadily up and down the thick, veined length.

Shame and arrogance crashed together in Jett’s chest. Shouldn’t he be begging for this ass?

He shoved his jeans down to his thighs, turning just enough to present the full, rounded cheeks of his bubble butt. The wide white elastic straps framed the pale, muscular globes like lewd gift-wrapping, digging in deep as he arched his back and pushed his ass out into the cool air.

The Black man’s breathing roughened. His fist sped up, thick shaft glistening, the flared head flaring darker with every stroke. White ropes of cum erupted from the heavy cock, splattering the leaves and dirt at his feet in powerful, pulsing jets. He milked himself through the last spasms, then tucked the spent length away, zipped up, and melted back into the shadows without a word.

Jett stood there half-naked, ass still pushed out, the night air suddenly cold against his flushed skin. That’s it? Dude just used me as jerk-off material and bounced? The hunger inside him felt even sharper now. He had offered everything — his body, his pride, his perfect quarterback ass — and all he got was a stranger’s cum on the dirt.

***

Further along the trail, a deep voice cut through the darkness.

“What’cha looking for, boy?”

A tall Black man stepped out from the shadows into the faint glow of the lamppost. Short-cropped curly black hair gleamed above a round, strong face framed by a moustache and goatee. He was solid and mature with a raw construction-worker body. He had powerful arms, a broad chest, and a soft, heavy belly that pushed against the tight black t-shirt.

As the man drew nearer, Jett’s eyes dropped involuntarily to the heavy, promising bulge in the front of his jeans. A knowing smirk appeared on the man's full lips.

“You look like you’re carrying something heavy, boy.”

“I… I don’t know,” was all that Jett managed to say.

The man chuckled low. “Yeah, you do. Come on. Let’s find somewhere quieter.”

Jett followed without a word. They walked a short distance to a secluded picnic table hidden in the trees. The man leaned against the table, arms crossed, studying Jett like he was sizing up a new toy. A low, satisfied rumble vibrated deep in his chest.

“You came all the way out here for a reason, white boy. You want it bad, don’t you?”

His big hand came up, gripping Jett’s jaw firmly. His thumb brushed slowly across Jett’s bottom lip as he stared down at him with dark, hungry eyes. His face split into a hungry grin.

“Strip,” the man ordered. “Everything off. I wanna see the whole package before I decide if that ass is worth my time.”

Jett’s hands shook as he obeyed. He pulled off his hoodie, then his t-shirt, revealing his broad, athletic chest and carved six-pack. The cool night air made his skin prickle. He kicked off his shoes, shoved down his jeans and jockstrap together, and stood there completely naked except for the black chastity cage locked tight around his cock.

The man let out a low whistle. “Goddamn… look at this boy. Perfect little white jock body, and now it’s just here for my Black cock. Tell me if I'm right, boy.”

"Yes... sir," Jett replied, staring at his feet.

Just as the man reached for hus belt buckle, a branch snapped somewhere near. Another figure stepped out from the trail. Both the startled naked Jett and the unflinching older man turned toward him. It was a younger Black man, tall and lean with a sleek, wiry build. His sinewy arms flexed under a sleeveless hoodie as he drew closer.

"Evenin', Reggie. Found some fresh meat tonight, huh?" the new guy said. A commanding goatee framed his lips that had curled to a hungry grin. His droopy, heavy-lidded bedroom eyes never left Jett's body.

The older man let out a low chuckle. “Wassup, Leon. Yeah, locked and hungry. Just take a look at this guy.”

The naked quarterback stood there frozen as the two Black men slowly circled him. The younger man stepped closer. “Shit, Reggie, check out that ass. Round, tight, and built just right." His palm cracked sharply across one firm cheek, the sound echoing through the trees. "And look at that little white dick — all locked up. That cage is doing its job, huh? Got this jock boy desperate and drippin'.”

Reggie laughed darkly, reaching down to give Jett’s caged cock a light, mocking flick. “Cute. All that athletic power and you still ended up with your dick in a cage. Turn around. Let me see that booty.”

Jett spun slowly, humiliation flooding through him as the two men openly inspected his naked body. Both Black men smelled of night air, faint cologne, and pure dominant male musk that made Jett’s hole clench involuntarily.

Reggie nodded in approval. “Yeah… that’s a nice jock ass. Now get on the table. Ass up. Let me see what that pussy is working with.”

Jett climbed onto the wooden picnic table on all fours, completely exposed under the night sky. The cool air hit his bare skin and his leaking cage. Reggie tore open a small packet of lube, coated his fingers, and pressed one thick digit inside Jett without warning. Jett gasped sharply at the sudden stretch.

Leon moved to the side, unzipping. He fished out his cock, cut, straight and long. He started to slowly rub its length.

While Reggie worked a second finger, then a third, inside him, the sensations crashed over Jett all at once: The relentless stretch and burn as Reggie opened him wider. The rough wood of the picnic table pressed cold and unforgiving against his palms and knees. His own caged dick leaked in a steady, humiliating drip onto the weathered planks.

Reggie pulled his fingers out. He mounted the table, straddling Jett from behind, and teased Jett's ass with the plump head of his cock. He pushed in slowly, inch by thick inch, stretching Jett open until he was buried to the hilt. Jett moaned loudly while Leon jerked his cock harder. Reggie started fucking him with long, deep strokes, hips slapping against Jett’s ass. Leon matched the rhythm with his hand, sliding his slim, elegant cock in and out of his palm.

“Fuck yeah… look at this white boy taking every inch,” Reggie growled, voice low and rough, hips snapping forward. “That hungry little hole is swallowing me so deep. You came here for this, didn’t you, white boy?”

The humiliation sizzled in Jett's chest, but it only made him push back harder onto Reggie’s thick cock.

Leon smirked down at him, pumping his long, straight dick. “He a natural, man. Like he been waitin’ on Black dick his whole life. Keep goin’, pretty boy — take all a Reggie’s shit. You gettin’ this one next.”

Jett’s thoughts were a storm of shame and overwhelming pleasure. Reggie’s chocolate-brown cock stretched Jett’s pink hole wide, veins dragging along his inner walls with every deep thrust. Jett’s muscular pecs bounced with every impact, his bubble butt rippling as Reggie’s heavy balls slapped against him.

"Come on Reggie, it's my turn on that pussy now", Leon said, moving behind the white boy. Reggie moved aside.

Leon laughed softly, low and filthy, as he lined up behind Jett and drove his long, straight cock straight into the slick, stretched heat in one smooth thrust. “Look at this pretty boy hole open up for me… you was walkin’ around all day with that cage on just waitin’ for a real nigga to stretch it out, wasn’t you?” He started pumping Jett's ass with long, steady strokes, hitting Jett's prostate every time.

Jett whimpered, the mix of shame and raw pleasure making his caged dick throb uselessly. He couldn’t stop. He didn’t want to stop. Every thrust, every filthy aspect of it only pushed him deeper into helpless surrender.

The two men kept using him, taking turns at his ass, their voices low and constant with dirty praise and mockery. “That’s it… take that Black cock in your hole, locked boy", Reggie grunted when it was his turn to plow Jett's white ass. Then it was Leon's turn again. “You feel that? That’s pure Black dick rearrangin’ that tight little hole. Keep pushin’ back on it — I wanna hear that cage rattle while I breed you,” he barked as his long, straight shaft pumped in and out of the jock boy's hole.

Jett was close — so close — but the cage kept him denied, leaking endlessly onto the picnic table while the two Black men fucked him senseless.

After what felt like an eternity of being used, the two men began to lose control as they took turns fucking the young athlete. Reggie’s thrusts grew shorter, harder, more possessive, his thick cock slamming deep into Jett’s stretched hole. “Fuck… gonna breed this white jock pussy,” he growled, voice rough and ragged. “You feel that, boy? Take every fucking drop.” His hips stuttered, then slammed forward one last time as he came hard, ropes of hot cum pulsing deep inside Jett. Reggie kept grinding through it, making sure every spurt was pushed as far as possible. “That’s it… take my load. Black seed, deep in your ass.”

Leon immediately stepped forward. With a wet, filthy splosh, he drove his cock straight into Jett’s overflowing hole, pushing Reggie’s load deeper. He set a relentless, rapid-fire pace at once. Jett moaned and whimpered as the older man’s cum sloshed loudly inside him with every brutal thrust.

“Take it, take it, take it… fucking little bitch,” Leon grunted, his possessive strokes turning frantic. His lean body tensed, abs flexing hard, heavy balls drawing up tight in their wrinkled sac as his erect black cock swelled even harder inside Jett’s slick fuck-hole. Then, with a long, guttural “fuuuck,” he unloaded, flooding the quarterback’s ass with heavy, throbbing spurts of hot semen.

Jett could only whimper helplessly as Leon’s cum mixed with Reggie’s, filling him beyond capacity.

Finally spent, Leon pulled out slowly. Thick strings of mixed cum leaked from Jett’s ruined hole and dribbled down his trembling thigh.

Reggie gave Jett’s ass a light, possessive slap. “Good job, boy. You took those dicks like a champ.”

Leon smirked, wiping the last bit of spit and cum from his cock onto Jett’s flushed cheek. “Yeah… not bad. Keep practicing and maybe we’ll see you around again.”

The two Black men casually zipped up, breathing hard but looking satisfied. Without another word they turned and disappeared down the dark trail.

***

Jett stayed on the table, legs shaking, cum slowly leaking from his used hole and dripping down on the picnic table. Tomorrow someone would sit here to have a meal and be disgusted with the filthy stains. Jett pulled up his jockstrap and jeans, the fabric instantly soaking through. He started walking back toward his car.

But the lust and curiosity were too strong. Instead of heading back to his car, Jett decided to wander a little further, “just to see.” He moved deeper into the paths of Riverbend Park.

A low, rhythmic slapping sound and muffled moans drifted through the trees. Jett froze, then crept forward carefully, staying hidden in the shadows. He pushed aside a low branch and peered through the foliage.

There, pressed against a huge oak tree, was the red-haired jock — the same boy Jett had spotted earlier. His letterman jacket hung open, pants and underwear shoved down around his ankles. The redhead’s pale, athletic ass was pushed out, his hands braced against the rough bark as he took a brutal pounding from behind.

The man fucking him was a burly Black daddy, thick and powerfully built, his heavy belly pressing against the redhead’s lower back. Jeans bunched around his ankles, his round, powerful ass flexed with raw, rhythmic hunger in the moonlight, dark skin gleaming with sweat as every heavy thrust claimed the white jock completely.

“Take that dick, you little bitch,” the burly top growled. He slammed in hard, hips slapping loudly against the redhead’s ass. “This is what you came here for.”

The red-haired jock whimpered helplessly.

The Black daddy laughed darkly and picked up the pace, his belly jiggling with every thrust. “Beg for it, boy. Tell me how much you love it.”

“God, yes! I love it! Please don’t stop, daddy… take me…” the redhead moaned, pushing back desperately, his pale freckled ass flexing around the Black top’s massive, curved cock. The wet, filthy sounds of skin on skin made Jett’s own cage throb in jealous sympathy.

Suddenly the burly daddy pulled out with a wet pop. His cock was thick and heavily curved, a fat banana shape that glistened with lube and the redhead’s ass juices.

“Turn around,” he ordered roughly. “On your knees, boy. Mouth open.”

The red-haired jock spun instantly and dropped to his knees, tongue sticking out, eyes glazed over with a dazed, cock-drunk stare. The burly Black daddy stroked his curved cock twice, then groaned deep in his chest as he came. Heavy strands of semen erupted across the redhead’s face — landing on his outstretched tongue, painting his cheeks, dripping down his chin. The top kept grunting, stroking out every last drop.

“That’s right… take my load, you locked-up white slut. This is what you get for coming out here begging like a whore.”

The boy moaned gratefully, tongue still out, his face painted completely with the older man's load. Then he quickly pulled out his phone and took a selfie of his cum-streaked face, the flash catching the thick white ropes dripping down his chin and the heavy, curved Black cock still resting against his swollen, glistening lips.

Jett stood hidden in the shadows, breathing hard, the image burned into his brain forever.

***

End of Chapter 9. Want the next chapter right now? Join my free Patreon membership for one-week early access: → https://www.patreon.com/HenryRaude. New chapters drop here first for free members. Full series coming soon.

– Henry Raude ([henryraude@proton.me](mailto:henryraude@proton.me))


r/ChastityStories • • 2d ago

M Chaste,F Keyholder Locked and Feminized in London (continued) [mf35] NSFW

61 Upvotes

Part 1 on my profile! Enjoy!

My wife had left me helpless. I stood there with my wrists and ankles cuffed out wide from my body. The Fembot costume I was dressed in had hiked up so my pink cage was likely on full display…but I wasn’t sure because of my blindfold. I hoped my makeup still looked good so I didn’t look too sloppy for whoever may encounter me.

Simon and Mia were having fun with the remote control as soon as Allie left. Initially the vibration was turned down very low so I could barely feel it and it was left there for a few minutes. Then suddenly it shot up to full power and my body twitched. I could hear them both laugh at my reaction and could feel a spurt of precum start to leak from my cage.

Their laughter was broken by the sound of the front door opening and the chorus of chatter amongst a number of women. They greeted Simon and Mia and from their conversation I understood it was a bachelorette party.

I was positioned so that I could be seen from the checkout but not from the front door so they hadn’t seen me yet. “We’ve had a few drinks so we might be a little loud but I promise we will try to behave”, one of them warned.

“Enjoy yourselves as much as you’d like”, Mia responded, “have fun”.

The chatter returned and I could hear the sound of the ladies making their way into the store. It only took a few seconds before I knew I had been spotted.

One of them stopped mid sentence and curiously asked aloud “what is this??”. The footsteps all approached me now when I heard Simon’s familiar voice state plainly, “This sissy is owned by his wife and she dropped him off here while she goes and hooks up with guys at the bar”.

The women broke into a chorus of laughter that soon shifted into a series of questions. Simon and Mia explained to them Locktober and the challenge that was posed to me.

Once they understood what was on the line, they teased me relentlessly. It felt like they were taking turns trying to push me over the edge. I’d feel an ass twerk against me, a warm breath on my cage, or a firm grab of my balls like they were playing a cruel game of roulette.

I fought with every ounce of my will to keep it together when I heard an unfamiliar male voice. “Oh shit she wasn’t lying”, he said with a chuckle. I could feel the attention of the room shift to this person.

He greeted the room when one of the women asked who “wasn’t lying”. He let them know, “My buddy is hanging out with his wife next door and she told me there was another Fembot here who I could get to know”.

His steps moved closer to me until I could hear him stopped right in front of me. “She’s very cute”, he complimented as his hand reached behind me and squeezed my ass. “Can we turn him around?”, he asked Simon and Mia.

They were agreeable and helped detach and reattach me to the restraints, now with my ass facing out to the room. The new voice commented on my plug and Mia handed him the remote. He immediately turned the speed up high and left it there.

The women in the bachelorette party saw this opportunity to spank my ass relentlessly. I felt many hands on me at once with smacks coming down one after the next on my cheeks. They burned and the women just laughed on cruelly. My ass must have been bright red.

The spanking subsided when I felt a light pressure on my plug. The pressure began to wiggle, moving the plug back and forth inside me. This sensation pushed another spurt of precum out of me. “Look at this slut drip”, the male voice commented.

“This is getting me way too hot, I need to get out of here”, one of the woman said. This seemed to snap the other women out of it and I could hear them all start to move away from me and toward the front of the store.

Before they exited, I heard a familiar voice from afar, Allie had returned. The matching costume being a dead giveaway, the bachelorette party immediately identified Allie. They complimented her costume and how hot she looked and told her what a good slut she has. She thanked them and approached me.

I could hear another set of footsteps with Allie when a new male voice said, “you found the other one”. “As soon as we saw you two out front we knew we needed to get to know you” he added.

“Turn him back around, I want to see my sissy”, Allie asked. Simon and Mia once again helped to reposition me. When I was facing forward, my blindfold suddenly came off.

My eyes adjusted to the light and I could see Allie standing in front of me with men on either side of her. In typical Allie taste, the men were both tall and dark skinned. Above her I could see the clock in the store showing 10 minutes until midnight.

Noticing me look at the clock, Allie commented that I was almost done with the challenge. However, she told me plainly that she didn’t think I would make it. As she said this, she started to show me why.

Allie grabbed each guy by the hand and moved those hands onto her body. She left one hand on her tit and the other on her ass cheek while looking me right in the eyes. “You like it too much when other men touch me… you’re going to cum”.

Her words were a statement of fact and my body believed it. I could feel my arousal accelerate and watching her be groped by these horny guys was pushing me towards the finish line.

The guy grabbing her ass moved behind her and began kissing her neck, his other hand on her upper thigh. The other man leaned over and pulled Allie’s top down so he could grab one tit while sucking the other. Allie loved this and I could see her squirm while these hands overwhelmed her.

When my wife pulled that free hand up from her thigh onto her clit, I knew I was approaching the point of no return. Time felt like it was standing still though. The clock still showed 7 minutes to midnight.

After this futile glance at the clock, something inside me told me I just needed to succumb to this orgasm. I needed to stop fighting and just let this month of pent up frustration explode from inside me.

When Allie’s panties were yanked down around her knees and ass-man’s thick finger found its way inside Allie’s wet pussy, it was over for me. “Just let go”, it told me.

It was a slow rise from inside me that felt like it took forever to build. I sat on the edge until my whole body reached the peak and convulsed. The release was overwhelming and I moaned in a high pitch as I came. I sounded like I was in heat. Cum shot and dripped from my flat cage as it felt like I was producing pints of jizz.

When I started to gather myself I looked up to see Allie staring at me with a slightly evil smile. “You were sooooo confident you would win”, she teased. “I was getting really wet thinking about sucking you off in the middle of this store”.

I was disappointed I missed the blowjob but that orgasm was earth shattering so I was feeling good nonetheless. “I really wanted to give some head”, Allie pouted playfully, “I guess I’ll just have to do it anyway”, she said as she hurriedly dropped to her knees and pulled out one of their cocks.

“Oh fuck” he said, his voice telling me he was the guy she came in with. My wife paused for a second and turned to the other guy. “I bet if you untie her she will suck you too”, she said, motioning toward me before quickly getting back to the cock in her hand.

The other man, the one who had played with me earlier but I had only just seen, began to untie my restraints. When he freed my last wrist, he led me by the hand next to Allie and pushed me to my knees.

Side by side, my wife and I sucked their cocks. The visual of two large black guys being sucked off next to each other by two Fembots must have been hilarious.

We bobbed on their cocks and sucked their balls, stopping to make out with each other intermittently. It was oddly, erotically, romantic to kiss each other deeply between throating these big cocks.

Both guys were getting more vocal so we knew they were getting close. “I’m bout to cum”, Allie’s guy grunted, pulling his cock from her mouth and jerking it over her face.

My guy followed suit immediately and we both pushed our chests out and presented our faces for their loads. Their grunting was near simultaneous as they both began to shoot thick ropes of cum over our faces.

These guys must have been pent up because they just kept shooting cum. Allie giggled and complimented her guy on how much he shot. When they were finished cumming, we looked at each other and both broke into a laugh. I could feel the amount of cum on my face and Allie was absolutely coated.

The guys left shortly after and we cleaned up our mess in the store. I had collected my thong and Mia returned the butt plug remote to Allie as we thanked her and Simon for the fun night.

Rather than walk back to the hotel with my cum on her face, we walked back together with both of our faces covered in other men’s cum. It was late and dark so we likely went unnoticed until we got back to the hotel.

We entered the empty elevator and the door was closing when a hand reached in to catch it before it closed. In walked the same hotel employee from earlier, initially apologizing for stopping the door so late before recognizing us as the costumed Americans from before.

“Fun night?” she asked with a smile, clearly recognizing the substance coating our faces and nighties. We both smiled, looked at each other, and nodded in agreement. Truly a Halloween to remember.


r/ChastityStories • • 2d ago

M Chaste,F Keyholder The Edge Olympics [Part 4] NSFW

24 Upvotes

This is Part 4 of The Edge Olympics. [Part 1, Part 2, Part 3].

This week, the girls decide the boys' edges require some "Quality Control"...

* * * * * *

On Sunday morning Andy Wilson woke from erotic dreams and found his girlfriend pinning him to the bed with a monstrous growl. He was lying on his back, as hard as possible in the tiny cage, and when he blinked open his eyes he saw Tash’s firm brown breast inches from his lips. His legs, pitifully weak compared to Tash's muscles, waved beneath the dome of the duvet, and were pinned helplessly beneath her calves.

“What’s happening, babe?” he moaned, and Tash simply gave another growl.

Andy swallowed, kissed her breast, and realised for the first time what an error he had made in telling Tash he wanted to win Gold: it had awoken something almost dangerous in her. Exciting, too – god yes exciting – but definitely dangerous.

And he couldn’t walk it back now.

It was impossible to pretend he’d somehow been lying or playing mind games: the chance to get a night with Tash and Martha and Liz made the mere idea he wouldn’t want to win absolutely absurd. It wasn’t just that the Gold prize meant the promise of sleeping with three women at once, although god knew that would have been motivation enough, but it was who those women were.

Tash, of course… but as much as he adored Tash, as desperately as he loved her, Andy would’ve had to be blind not to have fancied Martha with her glossy chestnut hair and incredible curves, and now that she was flaunting that key on the necklace against her chest, and now Andy knew precisely how much frustration that one key could imply… Jesus. The mere thought made him strain against the tiny little cage. And then there was Liz, slender, ginger, pretty… and apparently a natural fucking dominatrix who’d spent the first nine days of October quietly edging Dennis into an early grave?? Andy had adored Tash because of her dominance but the discovery that Liz had such a sadistic streak had made it almost impossible to sleep.

Unfortunately, Tash knew it. And knew she was twelve points behind.

For the first nine days of the competition, Tash had treated edging him almost as a luxury: something to linger over, a mutual pleasure to be stretched out until Andy was frantic, a game whose goal was the deliciously prolonged period in which she could control every thought in his head.

Now she knew she was behind, Tash changed gear with such suddenness Andy almost got whiplash; she barely let him wake before unlocking the cage to edge him, and his Sunday was transformed beyond all recognition; it was enough to make him almost wish for the safety of the Central Line – but they’d had nowhere special to be. Tash had no work waiting for her, no reason to dress, no reason not to spend half the day wandering around the house with the curtains drawn and her body stark naked and Andy as… Well, as her prey.

By breakfast, he was starting to think he might never be able to enjoy Jurassic Park again; she was taller than him – she was taller than almost anyone Andy knew – and when he’d gone down to make a cup of tea first thing, she’d actually pounced him, pinning him on the cold kitchen lino, tearing open his pyjama bottoms, unlocking and edging him right there in the kitchen, laughing as he yelped in astonishment, utterly helpless against her strength.

“We’re twelve points behind, babe,” she laughed “and I’m going to fix it. If you’re genuinely about to come tell me – but otherwise we’re spending today catching back up”.

Andy had whimpered, moaning as she clamped her hands against his chest and took his already twitching cock into her mouth – but he hadn’t realised then how determined Tash was.

“We’re going to win this fucking thing, babe,” she’d moaned, “or don’t you want to suck on Martha's tits?”

After Sunday’s brutally exhausting effort, Tash slowed down, at least. She had a major commission on and spent half of each evening in her workshop, sculpting what looked like, to Andy’s now firmly-fixated mind, a series of mildly obscene caged cocks all somehow far bigger than his nub cage would allow. She burst out laughing when he mentioned this, and patiently explained it was a series of bespoke cruet sets intended as wedding favours for a bridal party.

Even so, the look she shot him as she wiped slick grey clay from her fingers made it very clear he shouldn’t have reminded her about how small his cage was.

Her looming deadline aside, Tash’s teasing had become methodical in a way Andy had never previously associated with sex. She learned how long he needed to recover before she could start again. She learned which kinds of teasing made him too excited too quickly and which let her hold him exactly where she wanted. She stopped sending filthy photographs during the workday – partly because she had less time, but also because she’d decided any teasing that didn’t leave him sobbing on the brink of orgasm was a waste of the energy he’d need to survive the week.

She explained this in between his third and fourth edges on Thursday evening, giggling as his cock bounced and throbbed helplessly against her lips, and felt a rush of raw heat as he twitched, precome beading simply at the words. Simply at the knowledge she was actively managing his lust, driving him to endure being edged almost to the breaking point.

But by Friday evening even Tash was concerned she might be pushing Andy too hard. Edging him for the seventh time before dinner she’d come up for air, her mouth flooded with precome and found him clinging to the duvet for dear life, eyes staring blankly at the ceiling, his lips locked in a silent wail of need. She was smirking as she watched his cock twitch, thrusting helplessly with the adorable hope of a penis pleading to be granted a release, but when she glanced back at his face she shook her head and reached reluctantly for the little steel nub on the bedside table.

“That’s enough for now, babe.”

Andy looked at her, and blinked. “W-what are we on now? I lost count,” he said, laughing weakly.

“47,” she smiled, “you’re doing amazing.” Andy closed his eyes and tried to work out the maths. Six days ago, Liz had been on 22; if she’d put Dennis through five edges a day since then she’d be well over 50, and if she gave him six…

He opened his eyes, sat up, and kissed her. Then he rolled onto his side, kissing down the hollow of her neck, across the slope of her breast, and captured her dark nipple in his mouth. It was already rock hard, and she gasped as he started to suck, letting his teeth graze. When she looked down at him, she saw the frustration etched on his face, the tired bags beneath his eyes… and the resolution in his eyes themselves.

“One more,” he said, “I can take another. Give me one more. Then we’ll stop. I can take more tomorrow before the meeting. I can do this.”

Tash moaned, reached out, and clamped his head against her breast, keeping him suckling as she thrust her hand between her thighs and started to fuck herself.

This was far more intoxicating than simply making him obey. Andy knew exactly what another point would cost him. He was exhausted precisely because he understood. And he was still asking her to take control again because he wanted what waited at the other end of the month badly enough to endure it.

“Alright,” she sighed, her voice raw as her fingers curled against her clit, “alright. But first… keep sucking. Worship me. And… and give me your hand!”

He reached out, and she took his fingers in hers, deftly moulding his grip with her hand as she brought his fingertips to her swollen, splayed lips.

“Feel how fucking wet you’ve made me,” she whispered as he sucked frantically “feel how much I’m getting off on that beautiful locked cock of yours. This is what you’re doing to me, Andy. Every fucking edge, every little whimper, every day I keep you locked… you’re teasing me!”

He moaned, the sound muffled against her breast, but his tongue moved faster, his teeth keeping her sensitive nipple pinned as she made him masturbate her.

“You’re gonna regret teaching me how competitive you are, Andy,” she purred “but right now… right now you’re gonna make me come. And then we’ll make sure you’re set up to win the Olympics…”

He sucked even harder, his fingers finding the rhythm she liked, pressing deeper, curling inside her now as she guided his thumb to flick her clit.

“That’s it. Please me. Good!” Tash moaned, “You’re gonna win. And then… mmmmf, fuck! Good boy! When we’ve won you can do this to all of us. Fingerfuck Liz. Make Martha come on your other hand. And I’ll be sat right there on your face as the three of us use you as our clever, sexy, champion fucking dildo- OHHHH!!” Her thighs clenched so hard around his hand that Andy almost screamed, but his voice was too muffled, Tash’s wail as she came too loud, and he could only keep sucking, keep pleasing her. Keep doing his best as his cock surged and throbbed, soaking her outer thigh with precome as his balls ached harder than he’d ever imagined possible.

But he was going to win. He was sure he would.

* * *

The Committee met at Tash’s house that week, principally because Andy had announced in the group chat that if he had to fit the bloody thing across his back seats again he was going to start charging expenses. There was no hesitation or smalltalk this time; everyone was too invested in the scores. Again, Nigel poured the drinks while Martha watched him with obvious approval; Dennis sat beside Liz wearing the horrified expression of someone who’d spent the week discovering exactly how expensive a five-point lead could become; Andy remained standing beside the flipchart, purely because Tash had told him to.

Tash uncapped her pen and turned to the board, smiling.

ANDY: 50.

Martha’s eyebrows rose, Liz put her hand over her mouth, and Andy, despite the cramping of his balls, grinned proudly.

He'd endured hours of edging for that: 40 edges as Tash tormented him, took him shaking and pleading to the edge again and again. He barely remembered what orgasm felt like – but he'd shown Liz and Martha how he wanted them! Martha gave Tash a long, appraising look.

“Jesus. Andy are you sure you wouldn’t prefer the spikes?!”

Tash laughed, and waved Martha forwards. “Your turn.”

Martha took the red pen. She hadn’t been idle either, but even so all she could write was

NIGEL: 47.

Nigel sank a little deeper into the sofa, and Andy fought back the urge to cheer. For the first time since the competition began, he was ahead of someone. Only by three – but ahead. In the lead. Tash punched the air.

“Oh, fuck off,” Martha laughed. “You were twelve points behind Dennis last week, don’t start celebrating yet! Come on, Liz. What’s Dennis been doing in detention?!”

She sniggered, but fell silent as Liz rose, smiling.

“No.” Tash breathed, and Liz’s smile widened.

“Jesus. You haven’t? Liz?”

Liz turned towards the flipchart and wrote:

DENNIS: 60.

For several seconds nobody said anything, and then Andy flung himself down in the chair with a quiet “Oh… fuck”.

Tash stared at the flipchart.

Ten points.

She’d added 40 edges in seven days, driven Andy harder than she’d ever imagined she could, turned almost every spare hour of their week into some variation on erotic torture...

...and somehow Liz had still kept ahead.

And apparently, Martha was doing the same calculation Tash was, because she said sharply,

“You’ve added 38?”

“Well,” Liz smiled, “I wasn’t aiming for 38 specifically.”

Dennis gave a hollow laugh.

“No. She was aiming for all of them. Guys should we maybe ban spas?”

Liz patted his knee proudly, and leaned over to kiss him, but Tash kept staring at the board. Clearly something about it was bothering her. Not Liz. Not dishonesty. She believed Liz. Dennis’s expression alone was evidence enough that his week had been appalling.

But the numbers no longer made intuitive sense. Tash had spent seven days learning Andy’s limits. She’d pushed him hard enough that on Friday night he had asked for another edge against her better judgement, and she was still ten points behind a woman who had started October apparently worried she might not even know what she was doing. “I believe you,” Tash said.

Liz’s smile disappeared. “So I should fucking hope!”

“No, listen. I believe the 60. I’m not accusing you of cheating.” Tash gestured towards the board. “But I added 40 this week. 40. And I’m telling you now, some of those were fucking brutal. I made Andy cry twice, it was so fucking ho- it made me feel quite bad. But if I only managed 40 and you racked up a full 38 as well, then, Liz, either you’re much better at this than I am-”

Liz beamed, and Tash stuck her tongue out at her; Nigel couldn’t help noticing that even that made Andy wince, and Tash continued, “-or we’re not all measuring exactly the same thing. That could happen, right?”

Martha looked from Tash to the scores, and slowly nodded.

They had agreed an edge was an edge. At the time, none of them had considered how inadequate that definition was. Each woman knew what she meant; each man knew when he was about to lose control – but none of them had ever seen how the other couples were arriving at their numbers.

“OK,” Martha nodded, leaning back into the sofa. “She could be right.”

Liz looked betrayed. “You’ve spent the whole week telling me 22 was terrifying!”

“It was! 60 is worse. But that’s not the point.” Martha gestured at Nigel. “I know when he’s close because I can feel him change. Tash presumably knows because Andy cries and that does sound fucking hot…” Andy whimpered, reached out, and gripped Tash’s hand, and Martha went on, “and you know Dennis. But we’re assuming all three of us mean precisely the same thing when we say close, and we have absolutely no evidence that’s true.”

“Fine,” Liz snapped, and set down her glass. “Tash, we’re borrowing your bedroom.”

“What? For what? What?”

Dennis suddenly looked terrified.

“Liz,” he pleaded, “just think about this-” he began.

“No. You think I don’t know what an edge is, Martha? You think I can't make my man cry? Fucking watch me. Dennis – get upstairs.”

Dennis flinched at the pure headmistress-y command of her tone, but only said, “yes, Liz.”

Tash looked from one of them to the other, and grinned. “That’s perfect. Quality Control! I’m serious,” she urged as Martha laughed, “we each demonstrate one. Same conditions: own partner, own technique, other two women witnessing. The other boys stay down here so they get privacy from each other, but they each get a little taste of what it’s like to be fucking in the same room as each of the two women,” she said.

“Nigel’s up for that, right?” Martha declared, “I know he desperately wants Gold, I bet you’d love to let Tash and Liz see how fucking talented you are at… uh. Well, you want to show what you can do?”

Nigel nodded. Tash stuck her tongue out at Andy and glanced from him to her friends until he mumbled agreement, and then Tash grinned. “It’s official! Liz, do the honours.”

Liz nodded, uncapped her pen, and wrote on the flipchart.

QC: ONE WITNESSED EDGE EACH.

And beneath it:

QC EDGES COUNT FOR TOTALS.

And Martha bit back a moan of anticipatory pleasure.

* * *

Dennis went first; Liz insisted that having volunteered him it was only fair, and managed not to blush when Martha muttered something about ”showing off this legendary dick” as they climbed the stairs to Tash’s back bedroom. The space was technically a guest room, although like most guest rooms it had been quietly colonised by Andy’s collection of LPs, some flatpack furniture nobody had got round to assembling, and several carefully packed boxes of ceramics Tash hadn’t yet sold. But there was a bed and space for all three women, and so it would do: Dennis hovered by the bed staring at the floor and occasionally glancing at Liz for reassurance while Tash and Martha took up station against the opposite wall.

Liz felt far more nervous than she hoped she looked. She knew Dennis. She knew his body. She knew exactly what she was doing. But, with Tash and Martha watching, it felt different.

She’d slept with both of them years ago; once there had been almost no secrets between them. But after years where their intimacy had dropped she was sure they’d continued growing, becoming more experienced, more sexually adventurous. It felt like they were more naturally capable of doing exactly the kinds of things Liz had only just begun to enjoy, and she suddenly felt crushingly inadequate to the task she’d proposed. But then Dennis looked at her.

Not at Tash, nor Martha, but at her. Only her.

His expression combined pure adoration and nervousness and trust, and she realised she couldn’t feel nervous herself, not in the face of that faith. Because whatever experience and confidence or kink Tash and Martha might be used to, they didn’t know Dennis.

Still, she was terrified of exposing him.

“You… you’re comfortable? Can you hold the headboard?” she asked nervously, and then glanced at the others, blushing. “I… Normally I tie his hands back so he can’t… he’s strong,” she mumbled, and bit her lip as Tash purred approval.

“I’ve got some cuffs if you want? Strong ones. Metal. You can keep them even.”

“I… no. Um,” Liz mumbled, and then, “maybe… after? Not in the contest though, Andy might… It seems unfair to borrow kit. Let me unlock him though, I have the emergency key…”

She rummaged in her bag for a moment and drew out a dull brown envelope, somewhat crumpled. Dennis craned his head to see it and gave a yelp of outrage.

“You said that was a tax form!” he protested, staring at the neatly addressed ‘HMRC’ Liz had sharpied onto it. “Christ, I might have found that and posted it for you!”

“Well, it’s not a tax form. It’s the spare key,” Liz said, “but I didn’t put a stamp on it, so if you had posted it, well… um. Actually it might’ve got lost in a sorting centre forever, but I’d still have the other key, right? You know I have to unlock you to keep the numbers up.”

Tash covered her mouth, and Dennis lay back, face scarlet, unable to meet her and Martha’s amused gaze. Slowly, Liz unbuttoned his trousers and pulled them and his boxers down around his knees, carefully blocking her friends’ view until she had the cage open.

Martha gasped.

It dawned on Liz that there was a significant difference between telling her friends that Dennis was unusually well endowed and literally exposing him so they saw exactly what she meant.

They’d known, of course; once or twice Liz had confided in them, simply because her sense of sexual inadequacy was so painful there were times she simply wanted to beg for advice, but it had mostly consisted of “relax” and “you ought to try more lube”, and eventually she stopped asking because none of it helped. She’d never have dared betray Dennis’s trust by showing them photographs; the first time either woman saw what she meant was when Liz set the cage down and moved aside, by which time Dennis’s cock was already stiffening.

“Fucking hell,” Tash breathed.

Liz sagged with relief. Neither of them had laughed. Neither expressed confusion. Not the least wrinkle of their shocked expressions privately conveyed that Liz had somehow made an embarrassing fuss about nothing.

Instead, Martha’s face held something very close to sudden comprehension.

“Oh,” she said.

Tash’s eyes looked Liz up and down, and she grinned, “Yeah,” she nodded. “I get it. But… Christ, Dennis. Congratulations on winning the genetic lottery, I guess? Has it ever helped?” Despite himself, despite the fact his cock was now jutting up almost vertically, Dennis looked downcast.

“Not as much as you’d think,” he sighed, “I get a bigger cage, I guess?”

“You don’t have to,” Martha said, smirking, “We could standardise…”

Liz giggled, and Dennis fell silent instantly, but he kept his gaze on Liz. She was smiling. She looked so relieved his heart began pounding. For years, he knew, she’d carried the faint, irrational conviction that another woman would simply have managed better, ludicrously behaving as if he’d be happier if they could fuck more, or do anal, or… or if she simply fucked him more often. She’d always acted like she was the only person who thought he was unusually thick and that every other woman would simply look at him and be unimpressed.

Neither Tash nor Martha gave anything like that impression.

Martha gave Dennis another appreciative glance, then shook her head. “No offence, Dennis, because I mean, congratulations and everything, but Liz, darling, I withdraw every stupid comment about relaxing I’ve ever made.” She laughed to try and take the sting away and added, “I mean fucking hell, Dennis, I’m actually a little bit scared. Were you adopted? Is it possible your real father was a horse?!”

Dennis laughed despite his embarrassment; Liz finally met his gaze – and now, when she stepped back towards him, she wasn’t remotely nervous.

“Alright love,” she said, “let’s show them what we can do, shall we? Ready for 61?”

Dennis groaned, and clutched at the headboard until his knuckles turned white. Liz straddled his legs, stretched out her hand, and began to very lightly stroke his cock, while Martha and Tash watched in silent wonder, their eyes drifting from Dennis’s twitching shaft to Liz’s focused face.

It didn’t take long. Naturally it didn’t take long; his sixtieth edge had been barely more than two hours ago, and Liz could read him like a book. Her tongue flicked out, lapping up his precome in a way that made Martha’s breathing hitch, and then she resumed stroking his cock, using both hands to pump him up and down, faster and faster, working his cock as her fingers twisted.

Dennis thrashed on the bed, the headboard creaking as he struggled, his hips bucking.

“Liz please!” he choked, and then caught sight of Tash’s hungry gaze and clamped his teeth together as Liz drove him closer and closer to orgasm. Martha was breathing heavily, Liz’s pretty face was a mask of concentration; Dennis was whimpering in raw anguish as her hand rose and fell and twisted, his cock throbbing, sweat beading on his brow as his balls swelled and churned with need – and then, suddenly, almost at random as far as Tash and Martha were concerned, Liz stopped, pulled her hands away, and Dennis wailed, his hips bucking, and clung on until the wooden headrest warped to breaking point.

His cock throbbed, twitching and bobbing, swaying as the blood surged and stimulation faded, and then with a long gasp of “Oh god. S-s-sixty-one, Miss, p-please…” Dennis subsided, a single huge bead of gleaming precome slowly trickling across his cockhead.

Even the stimulation of that making him whimper.

“Miss?” Martha asked, breathing hard, and Liz glanced up with a kind of anguished embarrassment.

“On Tuesday I told him I was an expert in discipline,” she mumbled. “I liked the thought.” And her voice took on a harsher, businesslike register as she added, “So now he tells me. If Dennis doesn’t declare his edge count aloud, then that edge doesn’t count, right Dennis?”

“R-right, Miss,” Dennis groaned.

“Fuck,” Tash breathed, “No wonder you were pissed off when I said ‘actual edges’!”

“But… you let go before he counted,” Martha said. “So how the fuck did you know to stop?”

Liz shrugged.

“His legs had locked. And he swells a bit. And, well, you must have heard how instead of groaning fuck his voice got a bit lower? It’s… it’s just what he always does.”

Dennis’s eyes were clenched shut, his cock still twitching, each futile clench of his muscle setting it swinging like an upturned pendulum. Liz waited patiently, chattering to him idly, telling him about her ongoing frustration with the sports hall building works, and Tash stared in astonishment as the flow of talk distracted him enough to soften.

“You… you really know him…” Tash said as Liz picked the cage back up and began to ease his softened shaft back inside it. “Fuck. That’s how you’re doing it. You… You can jerk him right to the absolute edge because you… because that’s how you usually fuck him, right?”

Liz blushed pink, and nodded.

“OK,” Tash said, shaking her head. “Yeah. That absolutely fucking counts. Shit. That’s fucking hot but I need to up my game.”

The satisfaction that rushed through Liz was almost obscene.

“Thank you Dennis,” Martha said in her most formal voice. “You can let go of the headboard now. Don’t call us, we’ll call you.”

And then, as Tash burst out laughing, she added, “can you send the next candidate for the role of Boyfriend Being Edged Out Of His Fucking Mind up please?”

“I… yeah,” Dennis said, tugging his trousers back up. “I… I get to keep the job I have, right?”

Liz beamed, stood on tiptoe, and kissed him on the cheek.

* * *

After seeing how closely Liz read Dennis, Martha felt far less confident, but Nigel insisted he should go next. And she’d become astonishingly comfortable using him in private over the past fortnight. She ordered, Nigel obeyed, and the rest of the world ceased to matter – but that could hardly be true if Tash and Liz were there watching, and she found herself acutely conscious of being observed.

Tash and Liz were going to watch her ask for things, watch Nigel obey… Watch her enjoy it.

But after all, they’d seen her come before. They’d made her come before; it was the loss of that intimacy that had driven her, why she’d encouraged Nigel to push for agreement towards the Edge Olympics.

But she hadn’t anticipated mounting her boyfriend’s face in Tash’s back bedroom. Liz gave a hungry little growl as Martha hitched her dress up high and exposed herself, and Nigel took one frantic look at her and then focused all his attention on Martha as she descended over his face, leaning down to unlock his cock with the key around her neck and then steadily stroking him towards the edge as he licked her.

At one point, Martha glanced up to see Tash breathing heavily; she simply winked and dipped her head back down, while Nigel strained and licked beneath her, moaning as he bucked his hips up.

She closed her eyes, screaming as she came, listening to Nigel choke, almost forgetting the others were there as she shook in pleasure. Only when she dismounted did she see Nigel's soaking face crimson with embarrassment and gleaming from her wetness. She giggled, and tried her best to wipe him clean, kissing him before Tash could tease him about it.

In fact Tash said,

“That’s why you’ve been doing so many!”

“Because I’m getting eaten out?”

“No,” Tash said, and laughed, “well, yeah, probably. But he’s helping you.”

Nigel frowned, and Tash went on quickly. “Not in any kind of cheating way. I mean… It looks like he’s actively trying to give you the edge. He's getting off on licking you. Andy spends half his time panicking in anticipation of how long I'll hold him there.”

“I get it now," Liz nodded, blushing. "Why you like it.”

Martha beamed at her. It seemed Liz understood. For years, receiving oral left Martha wondering what Nigel expected for it. Now, she could come on his face, give him nothing - and he'd simply take it.

“Exactly,” she admitted softly. “It's so fucking hot.”

* * *

Andy came up last, looking terrified. He’d spent the last 40 minutes feeling less and less sure about this. Watching Dennis come down with a new and – as far as Andy could tell – entirely unwarranted swagger in his step had been bad enough; watching Nigel return grinning had been worse.

And now it was his turn. Tash’s turn. And Andy was just a little bit frightened of what that might mean, how he might end up looking. She could be almost animalistic when it was just him; he dreaded to think how she might act with an audience.

And then he stepped through the door and his cock surged at the heavy musk of feminine arousal in the little room. His eyes widened, and swivelled towards Martha. Nigel had just been up here. If the room smelled of pussy right now…

“Holy fuck,” he muttered under his breath, and winced as the tiny nub cage wrestled his cock back into submission. Martha was right there, legs crossed beneath her dress, the little key still visible at her chest, her cheeks rosy with arousal and the scent in the room…

Jesus and he could be with all three of them if he just did what they wanted, if he could prove he was worthy by winning the Edge Olympics!

He whimpered deep in his throat and sat on the edge of the bed before Tash could even tell him to, making her grin. For years Tash’s fantasies had focused on Andy’s erotic attention; she’d even told Martha and Liz about it – but she’d never imagined how intoxicating it would be if they were really there, intensifying his desires while she controlled whether he could come.

“Look at them,” she whispered, leaning in but still making sure the others could hear. “They don’t mind, Andy. They’d like you to look. I want you to look. Look at them – and remember who’s in control, babe.”

Andy whimpered as Tash began, and his whimpers did not stop for some time.

Tash was on her knees before him, blocking Liz and Martha’s view of the tiny cage. They already knew it was small; even if he didn’t know how absurdly well-endowed Dennis was, Tash didn’t want Andy to feel embarrassed: she didn’t want his humiliation, only the joy of cramming his perfectly decent-sized cock into a tiny nub – but that was a pleasure she preferred to keep private.

He took almost no time at all to get hard; she didn’t even have to remove the basering. His shaft simply sprang to life as she unlocked the cage and set it on the bed beside her, and then she closed her lips around the head of his cock with a happy little sigh and sucked gently.

Andy groaned, his eyes wide, staring, flickering desperately between Martha and Liz as if he couldn’t tell where to focus. The key hanging against Martha’s breasts, framed by her low-cut dress was enough to drive him to distraction, never mind the still-pervasive scent of her pleasure in the room, but as Tash began to bob her head to take his full, denied length down her throat, Liz gave a little moan of shock and crossed her legs.

Her audible arousal shot through Andy like lightning, a pulse of pleasure that sank into his depths and set his blue denied balls cramping in anguish as Tash paused, his whole cock throbbing in the hot confines of her mouth, and hummed.

“Oh god!” Andy choked, and Martha stirred in her seat, leaning forwards eagerly, convinced she was about to see him edge. Andy’s eyes stared desperately into the dark valley between her full breasts, and she bit her lip as she caught his gaze but didn’t shift position. She stayed leaning forwards intently, waiting.

...and waiting.

“Oh,” Liz muttered, and Tash pulled back slowly, still slowly, and let Andy recover for a moment before she swirled her tongue around his cockhead and then took him deep into her mouth again. Again Andy groaned, again his fingers clawed at the sheets of the spare bed, bunching the duvet as Tash deepthroated him, paused, hummed…

...and came back up while Andy whimpered, a high, strangled “Tash… fuck!!”. He was sweating now, his face scarlet, his eyes wide as he stared at his girlfriend’s best friends, and for a second, Tash hesitated – and then decided she had nothing to hide. She reached down and slipped her fingers under the waistband of her leggings, quietly, privately, masturbating as she edged Andy with the same slow determination she always did. The fact her friends were watching only made it hotter, and the little gasp of lust she heard Martha give as she realised what was happening was almost enough to tip Tash over the edge by herself.

“Look at them,” she said again, and her teeth grazed the tip of his head in that way she’d learned made him almost scream, forcing his swollen denied tip back to a level of almost post-orgasmic hypersensitivity. “Suffer for me, babe. We’re going to show that just because we’re behind it doesn’t mean I’m going easy on you.”

“Tash!” Andy choked, but her top front teeth had hooked just behind the curve of his glans and her tongue was thrashing across his tip with such twisting delicacy he could only lie back, choking on his own lust, whimpering in a way that only made Tash wetter.

She moaned around him and carried on, bringing him almost to the edge another ten times, and she could hear Martha almost panting behind her; even Liz’s breathing had changed, and Andy, writhing, tormented almost beyond endurance until Tash had to pin his thighs with her free arm, had long since lost the ability to look at either of their faces. He might adore Martha’s generous cleavage, but it was Liz who held him fixated now, all his attention on her modest, almost flat chest – and the suddenly prominent, jutting hardness of her nipples straining at her blouse.

And he could only look!

Which was already more than he deserved; he knew he was the luckiest man in the world to get head from his partner while her two best friends were sat there, watching and moaning – but to see the vivid, thrusting pink peaks of Liz’s nipples through her blouse and not be able to even reach out… It was enough to make him want to cry.

His cock pulsed as he imagined the prize in store if he could just endure enough edges to reach Gold; the way he’d be able to lick them, suck them if she’d only let him.

“Oh my god,” he whimpered, “oh god this is torture!”

And Tash came, convulsing; her throat tightening around his cock as she moaned, still sucking feverishly, still fucking herself with her fingers – and then as her own breathing subsided and her pleasure began to plateau, she bobbed her head faster and faster, throatfucking him until she felt the telltale twitching of his cock, and pulled away, gasping.

Martha stared at Andy’s throbbing, dripping cock, and put her hand over her mouth.

“Fuck me, Tash,” she whispered. “You’re evil…”

“I told you,” Tash moaned, wiping her lips delicately, “he tries to get away.”

“Yeah…” Martha said doubtfully, as she looked from Andy’s twitching cock to his almost despairing face, “but that’s so cruel. That’s fucking hot...”

Liz was pink, biting her lip hard, shaking her head, and then she said “you take ages though! That’s what you count as one?? Mine still count too, right?”

“Yeah,” Tash nodded, straightening, wiping her lips delicately, “it’s not about how you do it. It’s about how it affects them. I like the bit before the edge. The power. I… I like the idea I can make an edge so intense he’ll find orgasm a disappointment.”

“Tash!” Andy whimpered, “don’t tell them…”

“They’ll find out when you win, babe,” she purred, patting his thigh affectionately. “What the Gold winner gets to do is still up to us, remember.”

Liz moaned in a way that made Andy’s cock twitch and throb, a sound of such raw, passionate hunger his aching balls cramped even harder, and Martha shook her head in awe. “Oh Andy!” she breathed, “you are completely fucked.”

Tash laughed and leaned down to kiss his thigh before she took a firm grip on his balls and squeezed. Liz winced; Martha shivered. Andy’s cock slowly wilted until his erection had softened enough for Tash to be able to seal him back inside his cage.

“Well,” she said brightly, “I think after that… we deserve to have a drink and tease the boys, don’t you?”

And the three women burst out laughing.

* * *

Twenty minutes later the Committee reconvened and gave their official ruling: all three methods counted, and a new definition had been agreed: an edge required the controlling partner genuinely to believe that any continued stimulation would produce an orgasm imminently, with the man confirming afterwards that he had reached that point.

“You’re quite sure we don’t need a video review?” Tash said maliciously, and Liz and Martha sniggered while the boys yelped in protest. “It’s really common in sport, right?”

“It’s common in all the best sporting contests,” Tash continued, “Like… VAR? When was that, Andy?”

“Video Assistant Referee,” Andy said instantly, “introduced to the Premier League in 2016.”

“Cricket has Ultra Edge,” Liz beamed. “Dennis is always going on about it. Snicks and edges, right? We could… set up mics to track moans? Pulse monitors? Slow-mo precome analysis? Right love?”

“NO!” Dennis almost wailed, and this time everyone laughed.

“Fine,” Tash said. “Honour system, then. We know what methods each contestant is using. If the contestant declares her man has been edged, that’s what counts. Agreed?”

There was a murmur of assent, and Tash stood to amend the board:

ANDY: 51

NIGEL: 48

DENNIS: 61

Andy stared at the numbers. Liz was still ten ahead. And he wanted to win Gold more than ever.

“Everything just got worse, right?” He asked helplessly, “For you guys too?”

Dennis took a long, long drink, and nodded. “Yeah mate,” he sighed, “I think it might’ve just got worse. Feel free to drop out though. I’ll have Gold for you.”

The women exchanged a triumphant glance, and Martha felt a surge of pure happiness. It was the kind of look they’d once exchanged almost every morning, certainly every weekend; the kind of look that said ”Morning, I shagged that guy I pulled last night; shall we compare notes?, a look that practically begged for intimacy, a shared connection and joy in one another’s pleasure.

She’d missed that connection more than she could ever have realised, and the intense furnace of Quality Control had finally returned it – and given her a far deeper appreciation of exactly what they were, collectively, putting their men through. Martha had watched Liz turn years of intimate familiarity into frightening precision, but now she also knew Tash could keep Andy hovering in psychological agony for far longer than she’d ever attempted with Nigel.

She bit her lip.

Nigel isn’t going to get much sleep she thought to herself with a laugh, and then, astonishing herself, I might not even bother to edge him while he licks me.

God. She was soaking.

“Same time next week?” Tash grinned, and all of them – even the men – nodded.

Later, after the others had finally left, Andy found Tash standing in the kitchen looking at the Habit Tracker on her phone.

She reached out her arms when he paused beside her, placing her hands on his chest and backing him slowly up against the wall before she kissed him deeply.

“Ten points behind,” she said, “and now Liz knows what she’s up against. I take it you still want to win this? Despite everything?”

“Yeah,” he said, swallowing hard. “More than ever. Only I don’t know if I can.”

“Don’t worry,” Tash whispered. “We’ve got a whole week. I’ll make you succeed, babe.”


r/ChastityStories • • 2d ago

M Chaste,F Keyholder Sister (slow burn) Pt2 Ch5 NSFW

28 Upvotes

Links to: Pt1 Ch1; Pt2 Ch1, Pt2 Ch2, Pt2 Ch3, Pt2 Ch4

All characters in this story are 18+

CHAPTER 5.0

Pairs with Pt1 Ch5 & Ch6

Like I said before, I never approached Kent or, really, any other person in my life, with the intention of keeping them in chastity.  But especially not my brother.  I was observing behavior, not thinking of it sexually.  And there were no outwards signs that he’d even be into chastity.  He was just… submissive.  That’s who he was, and is.  Regardless of who I am, that’s who he is.  It was evident.

With him, with us, it must have been a culmination.  Horny teenager stuff, plus being in close proximity enforced by Covid, without any supervision, both of us exploring our dominant and submissive sides.  Or perhaps embracing those sides, more as a coping mechanism. 

He had been moping for as long as I could remember, when suddenly: a package!
More than that, a package that he ran, sprinted, downstairs to get, and then refused to tell me what it was.

How unlike him, to not immediately comply with one of my requests.  It piqued my interest enough to be on the lookout for packages in the future, and holy shit, did I hit the jackpot! 

It was a silver micro nub chastity cage.  I had a pretty good idea what it was, but I posted it, and my ladies confirmed.  They asked if it was electronic, but it didn’t seem to be.

Well well well, my big brother.  Most guys are growers, to some extent.  But flaccid and locked up, this thing would barely be noticeable in a bikini bottom. 

I began to drift in my thinking.

Chastity is a bit selfish, you know...  On the part of the chaste person.  I know people think it’s the other way around, but it’s not.

Yes, the chaste person is “owned”.  The keyholder own his erections, his orgasms, and his ever-present unrelenting desire.  But really, what submissive boys want is for someone to focus on them.  They’re sexually useless, and chastity “makes up” for that.  For my brother, it’s the only way he’d get someone to have any interest in his penis.  I love him, but it’s true.

I could imagine it being special to me as well.  Letting my brother be selfish is something I’ve denied all the other boys who have slipped into, and then unexcitingly faded out of, my life. 

Not that there aren’t benefits for me.  Don’t be silly!  Any relationship is a give and take.  But the way I perceive it (and the chaste person’s opinion doesn’t matter if he’s in my cage), we both have the unique, exciting, authentic, and very pleasurable opportunity to be on the outside who we are on the inside.

Suddenly, I snapped out of it.  What was I doing thinking about my brother’s penis??  Flaccid or otherwise?

The little sexual games I played with him were the same as I played with every man.  I don’t think it was exactly “normal”, but for me, for my personality, there was no differentiation. 

Yet, I was wet.

Why?

People get wet by things they aren’t turned on by.  That’s a fact.  Bodies respond to stimuli they think they’re supposed to, and it misfires.  I bet every boy who got an erection in 12th grade math class can attest to that.

Maybe there’s no reason I was wet.  But still.  I’m analytical.  Why?

In all honestly, I couldn’t come to a non-sexual conclusion which didn’t feel… off… wrong.

I don’t know if the knowledge made me more flirty, more dangerous, or both.

I didn’t like having this much focus on it, but the idea kept popping into my head.

My brother, my older brother, my VIRGIN older brother, could have his cock locked in chastity literally any time we were interacting.

I wanted to know when it was on or off.  One of the most obvious ways I could tell was when he would or wouldn’t come swimming with me.  I teased him a lot about that, since I knew his cock was locked up, and knew he didn’t know I knew.  I loved seeing him so uncomfortable!

Omg there was this one time where I went to the door in my undies (which I will add, plenty of people were doing during lockdown), and the little chastity bitch had the NERVE to talk to me about it, to tell me it wasn’t right.

It’s ok though (especially now that I control his little horny nub).
But I did try to humiliate him a bit, baiting him into admitting he was attracted to me.
Bet that really got him going.
I couldn’t believe I was even thinking this way, but I bet he was touching himself thinking about me!

 

CHAPTER 5.5

Pairs with Pt1 Ch7

My little corner of the internet, was convinced he was a panty boi.  They were convinced it would give me complete power over him.  I was not, and to be a little honest, am still not convinced they’re right.

It’s just not his thing.  It’s the same way it was with the feet.  It’s not the feet, it’s not panties, it’s me!

But then I thought about it a different way.  How incredibly self-centered, possibly even delusional, my thinking was.  I resolved to at least try their suggestion.  It wouldn’t confirm whether he was a submissive pervert, or a submissive pervert for me alone, but at least it was data.  So, panties. 

And as it turns out, they were partially right.  I’d later be quite surprised to discover the depth of his panty-related fetishes.

I still didn’t think it would get a result though.  Even while setting things up, I didn’t think I would.  I guess we were just so comfortable with each other that I might have missed it.  But the coven had taught me long ago what I should be looking for.  The stammering, the uncomfortable body language, and oh let’s not forget, the leaning over his crotch and trying to cover it with his hands.  Hilarious because, if he was in the micro cage, as I suspected he was, there wouldn’t be anything to cover anyways.  Biology though. 

I left my panties out for him to find.  When he asked about it, I tried to play it off as an accident, and I think he bought it.  Right at the end of the conversation, I wanted to make him a bit more uncomfortable before I left.  I reiterated that these were MY property, and he wasn’t to touch them under any circumstances.  Add a little forbidden fruit suggestion.  And a second before exiting, with a wink and in a swirl of hair, I said “These aren’t for you, obviously.”

And THAT was when I saw it.  It finally clicked.  TWO pieces of the puzzle, and I had previously only had the one.

It wasn’t just that he was obsessed with me.  Virginity!  And in relation to me.

The idea that he was a virgin, and his little sister wasn’t, must be what powered his dreams, erections, fantasies, oh and best of all, his insecurities!

I’d had fun with one virgin, after Bradley.  And unlike Bradley, I didn’t let him get in my pants.  Oh god, was he desperate!  D e s p e r a t e!

But this was my own big brother’s virginity, right there in the palm of my hand.

Wet again!  And this time, I was hardly confused, I was really enjoying it!  It was thrilling!

I had kind of been in a rut with the lockdown, but this really did something for me.  I was seeing something so personal!  Just by seeing it, I was taking something from Kent.  And I knew as long as he didn’t know I’d seen his cage, this would be my new project.

I felt this rush in the moment!  I gave him that wholesome smile people have complimented me for and, after I left the room, whispered, “My big brother...”


r/ChastityStories • • 2d ago

M Chaste,F Keyholder Locktober's End- Chapter 1 NSFW

17 Upvotes

It was Halloween night, so of course we ended up watching a horror movie. A couple, actually.

I wasn't always in the mood for that sort of thing, but I knew Ben was a fan; and of course, it was Halloween.

I had been stroking him softly throughout most of Halloween III- that's the one that gets a bad rap because there's no Michael Myers, but it's actually very fun and creative- although I'm not sure if "stroking" is even the right word. It was more like feather-light touching through his jeans...in keeping with the feather-light quality of most of the kisses and physical contact I'd been giving him throughout the evening. He had started to squirm early in the movie, and had leaned over to tell me how evil I was being.

Well, it was Halloween. I smiled at him. "Do you want me to stop?"

"No, no, no, no, no", he assured me quickly, his eyes widening. I didn't hear any more complaints for the rest of the movie.

Once it was over, I asked him what he thought about the plot, the characters and so on. I even made him give me his opinion on the sound design, all while I had my hand under the blanket we were sharing, rubbing him slowly through his pants- just enough to distract and make him squirm. His answers were impressively coherent, I have to say. I liked that. I liked a challenge.

Finally I asked, managing to suppress a giggle, "Are you ready to cum?"

I couldn't suppress the giggle at his reaction, however. Head thrust back dramatically, eyes closed, an expression of agony that I suspected was at once for my benefit, but also genuine. "Oh god", he whimpered. "Oh god...!"

I paused for a moment, looking around my mostly dark common area- my eyes passing over the bookshelf, the TV, my guitar, the few candles I had lit. We were getting close to my favorite moment, and I wanted to savor it.

I wanted to draw it out. So I pretended not to understand. "Is that a yes?"

A tremor went through him as he pressed a little harder against my hand, his hips leaving the couch. "Yes, god yes, please Miss Jessica, please...!"

I smiled and moved a little closer, kissing him on the cheek and holding his manhood through his pants a little. Not moving my hand anymore, just...holding it. "Are you sure? Isn't this nice, though? Sitting here like this?"

"Y...yes, but..." His eyes were still closed.

"And you told me Daughters of Darkness was really good. Just a few hours ago, you were eager for me to see it. I told you how unlikely it is for me to watch a horror movie once November hits..."

"Th...that's true", he groaned helplessly, his whole body trembling.

"Besides, do you really want this feeling to dissipate so soon?" I'd gone back to stroking, the lightest and most feathery of touches. "Maybe just one more movie?" I glanced at the digital clock in the corner, as I had a particular need to know exactly when it was, but I think time had become an abstraction for him.

"I...I..." He whimpered. "Maybe you're right."

I might have been being a little evil, sure, but he really had hyped up Daughters of Darkness to me. I already respected his taste at this early point in our relationship, and I really did want to see it. And hadn't he said that he wanted to please me, "yield to my desires and whims in all kinds of little ways?" I was only granting his wish.

"Of course I am", I smiled and kissed him one more time on the cheek as he reached for the remote with a shaking hand.

*

I'd met him for the first time only the previous weekend. Our band The Acolytes had been performing at Prince of Tides, a bit of a dive on the other side of the river from where I lived, and we'd just finished our set. I was tired after about 30 minutes of singing and playing lead guitar, and my first instinct was actually to head home- I had a weekend's worth of papers to grade, and a project to work on for my own classes- but our bassist and my longtime friend/creative partner Lee was friends with the headlining band, and I figured it would be more polite to stay and watch them. Supposedly their live show was pretty impressive, and I knew I would get into the groove once they started playing anyway- would be glad I'd stayed.

There was that little pocket of time in-between, though, after I'd helped the guys bring a few amps and pieces of equipment back to Lee's van and while the headlining band was setting up- that relatively quiet pocket of time that I'd always liked. The liminal space. Oh sure, Prince of Tides was no different from most other venues in that they tended to play background music between bands, in this case it sounded to me like something 80s-ish and Cure-adjacent- but it wasn't so loud that it precluded conversation. And in comparison to the way I'd spent the past 30 minutes, up on the small bandstand, it felt like the volume on everything had been turned down very low, like I was swimming underwater.

It was a pleasant but slightly surreal feeling, and somehow I ended up by myself at the uncrowded L-shaped bar, where I asked the pink-haired female bartender for a well-deserved gin & tonic. She told me how much she'd liked the music, and I thanked her. I knew that Lee and our drummer Gunnar (he's Scandinavian) would probably be out smoking pot in Lee's van for at least ten minutes, and the part of myself that wasn't lost in underwater la-la land braced myself for the possibility of being hit on...but then again, it didn't seem all that likely. It was true that, in all humility, I thought I looked pretty good that night- I was wearing a purple sleeveless dress that ended at my knees and not much else, my red hair down around my shoulders (it seems to change colors sometimes, but if you catch it in natural light, you can tell that it's red), a pair of jade-colored dolphins hanging from my ears and a necklace around my neck- but a lot of guys were intimidated by the lead-singer thing, and moreover there just weren't that many people around in general. In fact, the only guy sitting at the bar who appeared to be around my age (he looked mid-30s-ish) was sitting a few chairs away, reading a paperback book. Which struck me as a little odd. Was he really able to read with all the noise around him, or was he just waiting for a woman to ask him what he was reading? He seemed to be drinking a beer that wasn't too dark, maybe something like Blue Moon, and he'd drunk about half of it.

The pink-haired girl came back with my gin & tonic, and we talked for a little while until a 50-something couple showed up on my right side. They started asking about the menu. As I sipped my drink slowly, I had the temptation, as we all do these days, to take out my phone...surely I could find something to occupy myself...but I was still feeling a tremendous rush of adrenaline from the performance, and I found that I didn't want to dilute it in any way. Or that I wanted to dilute it only with slow sips of gin & tonic, not by scrolling through my phone. In any case, for whatever reason, I found myself glancing over at the 30s-ish guy again. He was nice-looking, with brown hair, glasses, and a little bit of stubble on his face, which had a relaxed and kind expression. Maybe an average build. He didn't look like he lifted weights, exactly, but he was slim and maybe went running now and then. He wore a collared forest-green short-sleeve shirt, brown khakis, and sneakers. As far as I could tell, he was genuinely absorbed in his book.

And just like that, against my better judgment (in retrospect, I think the gin helped), I asked, "What are you reading?"

What I remember about his reaction is that for a few seconds he looked (gratifyingly) very shy, but he recovered quickly as he showed me the blue-and-green cover of a substantive paperback book that he appeared to be 2/3 or so of the way through. "Sometimes a Great Notion", he said.

I shook my head. "I've never heard of that one." I squinted at the cover. "Oh, Ken Kesey?"

He nodded. "But you've heard of One Flew Over the Cuckoo's Nest."

"Of course, I read it in high school. It was really good."

"Well, this is Kesey's lesser-read second novel about the downfall of a lumberjack family in Oregon."

"Is it good?"

"It's great, I'm loving it. The only thing that's painful about it, for me..."- he grimaced self-deprecatingly- "...is that he finished it before he turned 30."

The comment sat in the air for a moment; our eyes met in the silence, and we both somehow acknowledged the absurdity of calling to each other like this over empty seats. I had started the conversation, so it seemed only fair that I take the initiative.

Once again, the gin helped. "You can sit closer if you want. I don't bite."

"Oh, okay." He got up from his seat abruptly, dare I say obediently...voice a little shy, no longer as confident as he'd been while describing Ken Kesey's early writing career, happy to let me take the lead. Looking back, I think I knew from that moment. If not before.

"I'm Ben."

"Jessica."

*

The headlining band seemed to be taking a long time, endlessly unspooling a labyrinthine complexity of cords and plugs. Lee and Gunnar were off somewhere, maybe having decided to take a walk to the river while stoned. Prince of Tides was playing what sounded like Siouxsie and the Banshees over the sound system. But the end result of all those circumstances, was that Ben and I had time to talk, for what felt at least like a half-an-hour. I told him that I was in grad school for psychology, and he told me that he taught english at a nearby community college.

That tracked. Music had always been a passion for me, but the truth was that after spending my 20s wanting to pursue that artistic path to the exclusion of all things, I'd become laser-focused on getting my Master's, both because I was interested in the subject and because I was starting to feel the pressure to secure things like a decent salary, healthy insurance, and maybe even a small house of my own someday.

It seemed he had lived a more itinerant life than I had, and had even spent a few years teaching english as a second language in eastern Europe and southeast Asia. I was a little in awe of that; but I also think, in retrospect, that he was a little in awe of the simple fact that I was in a band. Looking back, our meeting seemed to expand the world for both of us, stretch both of our horizons. That happens in some small way whenever we meet anyone new. I was reminded that some people actually do go off and live for years in foreign countries, having all kinds of adventures that those of us who stay in the States will never experience, and he was reminded of an entire world of music and creativity.

Anyway, It turned out that he had seen the show, and liked our blend of shoegaze and doom-metal (he would admit later that he'd been attracted to me from the beginning, that the "ethereal" quality of my vocals contrasted with the heaviness of the music had set his heart a-flutter), which he thought was unique and also very autumnal. Something about it was appropriate for the Halloween season, he said, his book now closed in front of him (he'd remembered to put in his bookmark, which appeared to be a movie stub) as he sat next to me. He liked the season, even if, as he explained, he was not a big Halloween party-goer or costume-wearer.

It was only the 26th, a Saturday, but I explained to him that my Halloween was already pretty much over. "Went to a party at my friend Susan's last night", I explained.

"Oh?" He took another sip of what I believed to be Blue Moon. "What did you go as?"

"Oh, the truth is I wasn't really anything. But I wore this black dress, some fishnets, put on some fake horns and sort of pretended I was a sexy devil. Or maybe just a devil..."

"I'm pretty sure you were a sexy devil." He paused, blushing a little, not looking at me, taking another sip of Blue Moon. "Wish I'd been there."

I couldn't help laughing. "I'll bet you do."

"Did you, um, wear boots?"

"Hmm?"

"With the fishnets, I mean. I sort of picture black, high-heeled..."

"Well aren't you inquisitive. But you said you don't dress up, so you wouldn't have been allowed in anyway. Even if I'd known you yesterday, you wouldn't have been able to join me." I stuck out my tongue. "Sorry, not telling. You'll just have to imagine", I smiled.

"Oh, I would've come up with something to get into the party."

"Like what?"

I observed him thinking hard, trying to come up with a costume idea that would amuse me. I liked that expression. He took a sip of his drink to buy some time.

"Oh, I know", he said as he placed his beer back on the coaster. He nodded slowly, now that he had his idea secure, savoring the moment. "I could've been a writer who sold his soul to you in exchange for success." He grinned, gesturing with the Ken Kesey book. "In exchange for writing a masterpiece like this. Maybe I could even have brought a fake manuscript or something, ostensibly full of the brilliant ideas you'd granted me..."

I smiled. "I like that one."

"Of course, you'd have my soul."

"Oh, of course. We made a deal. You're not backing out of it."

He shrugged. "Well, at least you're a female devil."

I snorted and giggled at the same time. "Oh, that makes it better, huh? You gave away your soul, and it's okay just because I'm a girl? That's your soul, dude!"

"Wellllll, it was probably a foolish decision on my part, I'm just saying it could be worse. You could be some big ugly-looking guy. I'm just trying to look on the bright side."

"No matter how you slice it, or what side you look at it from, I have it and I'm not giving it back."

He nodded with- if I'm not mistaken- pleasure. "A deal's a deal, after all."

"A deal's a deal", I agreed. "Especially when you sign in blood."

"The foolish decisions we make because of a pretty smile..."

He glanced at me shyly as he said that, and I felt myself blushing. I quickly cleared my throat, but I'm not sure what made me say the next words. "Where do you think I'd keep it?"

He looked at me sideways now, still a bit shy, and took another sip of his drink. "My soul? I...I don't know." He shrugged. "That probably wouldn't be for me to know."

"That's the correct answer."

"You probably wouldn't want me to know where you kept it. Because if I did, that would increase the chance, however unlikely, that maybe I could find a way to get it back."

I nodded. "That's logical enough."

"But..."

I looked at him playfully, a little warningly.

"I guess I'd expect you to keep it in some old mahogany chest, somewhere like that. Or whatever that key you're wearing opens."

I'd like to swear that I hadn't been baiting him this whole time, and I really don't think I was. But in retrospect, I'm not so sure. I hadn't even thought about it for most of the month, had just kept wearing it a few weeks before, when things hadn't worked out with Chris. Now I reached down and touched it as casually as possible. I felt the jade dolphins dive underwater as I moved my head, then resurface as I looked back up at Ben. "Oh, this."

"Um, yes. Not that I was staring. But my gaze did, uh, just happen to..."

"Uh-huh. Just happened to...?" I was happy to have the upper hand again, as he struggled to explain. I didn't rescue him, except with a slight smile. For the most part, though, I just let him spend the next minute hanging himself. It also gave me time to think about what I was going to say next. He was cute, and I was tempted to tell him the truth. But after Chris, I thought it best to be prudent. Besides, October was nearly over anyway.

It was best to be prudent. But I wasn't.

NOW

Despite the enjoyment I was getting out of teasing him, I really did become engrossed in Daughters of Darkness. Delphine Seyrig, though a little on the older side, gave a truly hypnotic performance as a woman who may or may not have been the immortal Countess Elizabeth Bathory, and the movie had incredible gothic atmosphere. When it was over, I slid closer to Ben, brushed his waist with my hand, kissed him on the mouth, and told him that I had really liked it. He seemed gratified, and asked if he could get me anything.

"I could use a glass of wine. Fill my cup for me?"

"Your wish is my command."

I stifled a giggle as he stood up. He was rock hard and pressing against his jeans, and it caused him to walk a little awkwardly as he made his way over to the kitchen island. A slight whimper escaped him at my stifled laughter. Don't worry about that aching hard-on, I almost told him, we'll take care of that soon enough. But I was pretty sure that, if I said that, my uncontrollable giggles would give away what I still hoped would be something of a surprise.

Something of a surprise. He knew what was going to happen. But I don't think he really believed it yet. He would, though.

In any case, I managed to be mature, watching him with a smile as he filled our glasses.

"Well", I said when he sat back down next to me, "I bet you're really ready to cum now."

He thrust his head back in a delicious portrait of agony. "Oh my god..."

And just like that, the articulate film aficionado had disappeared again, replaced by a desperately horny guy. He looked even more helpless than he had earlier in the night, tormented by a few hours or stimulation and close contact and perfume and feather-light kisses that never progressed beyond kissing and the dark-blue date-night dress that I thought looked quite pretty, if I do say so myself. My nails matched the dress, and I imagined his balls were already the same color.

Abruptly, and without ceremony, I slid on top of him, straddling him, my dress riding up my thighs, and kissed him deeply. In my peripheral vision, I could see the hand that held his wine shaking.

"Don't spill any on my couch", I smiled. "Wine, that is."

He angled himself to put the glass on the table. I thought about commanding him to keep holding it, but I didn't want to waste good wine.

His dick was still trapped and struggling beneath his jeans, which I knew he wouldn't remove without my suggestion. Without my permission, really. Some guys probably would, but not him. His penis was trapped and struggling, yes; but considering the plans I had for it in the very near future, he would probably look back on these hours as a period of almost inconceivable freedom.

"Oh yes, you're ready for an orgasm. Aren't you?" My hand reached down again, and I rubbed him softly as we kissed, feeling his manhood pulse and throb against his jeans. Throbbing...yet contained. Stymied. It's the way I feel all cocks should be, if I'm being honest.

He nodded, non-verbal, but I wasn't going to let him get away with that.

"Say please."

I sensed his hesitation. He'd probably fantasized about such things; but he'd already told me he didn't have much firsthand experience with kink, and it was different in the moment. He'd never experienced the genuine vulnerability that came from begging...and meaning it. And not knowing if your desire would be granted.

I wouldn't enjoy that, personally, of course. I like being able to have an orgasm whenever I want.

"P...please."

"Please, Miss Jessica."

A shiver went through his whole body, and I was worried for a second that I had pushed him too far, that he was going to explode. But he kept his self-control admirably.

"P...please, Miss Jessica." It seemed to give him almost as much pleasure as it gave me to hear it.

And that was when I pulled my hand away, stopped kissing him, and just...

...stopped. Stopped...everything.

Except of course for looking down at him and smiling as his hips still made little thrusting motions, as his eyes opened wide in surprise and disappointment, as he said the word "please" perhaps more earnestly and pleadingly than he ever had in his life.

"You do seem ready", I smiled, holding my chin in my hand thoughtfully. "There's just one...little...problem."

THEN

It was best to be prudent.

But I wasn't. I couldn't help myself.

"I guess you could say it's like a costume I wear every year", I said, looking up slowly from the key. "Every October, specifically."

"It must open something valuable."

"Mmmm. Not this year, unfortunately."

"Well", he paused. "November's just around the corner. Who says it only has to be for October? Maybe you could still find that valuable thing."

Our eyes met. God bless alcohol, because otherwise I'm quite sure he wouldn't have said anything like that, and I probably wouldn't have, either. I still wasn't totally sure we were talking about the same thing.

I sat up straight, brushed my hair back, turned slightly in my chair to face him. I smiled and rested my hands on my bare thighs. He turned his head towards me, but not his body- almost as if he were a little afraid. The truth was that there were little butterflies in my stomach as well. "It's not really for anyone. At least not this year. I just like wearing it. And sometimes, up on stage..."- I took a deep breath, meeting his blue eyes- "I'll look out at the the people here, and I'll imagine that it belongs to one of the guys, maybe some cute guy sitting at the bar..."

"...reading a book?"

"Could be." It seemed that we both knew what we were talking about now. But I wasn't sure if I was just teasing him (and to some extent myself) with the idea, or seriously contemplating it. He did have a point, though. There was no rule that restricted such things to October; no rule that said you had to follow some niche internet fad to the letter.

"Mmm." I smiled wider, unable to help myself. "A thoughtful, articluate fellow like yourself. I like seeing the contrast that sets in once I..." And then I trailed off, reached for my gin & tonic, and decided it was time to be responsible. I reached over and took one of his hands in mine- his were a bit larger, naturally, while my nails were painted the same lavender as my dress. "Look, Ben, you seem like a nice guy, but there's a reason I went to that party last night as a devil. I can be evil."

I looked into his eyes as I said this, and I could tell that my words did not dissuade him. Maybe I didn't want them to. Maybe holding his hand the way I was was part of the same evil I was talking about, operating within me on only a semi-conscious level. Looking back, I have no recollection of anything else that was happening around us.

He looked back at me earnestly. His face seemed to twitch a little, as if he almost averted his eyes but then forced himself not to. In contrast to how relaxed his posture and speech had been earlier, he now seemed tense, nervous, his words clipped. "I...I like that."

I, on the other hand, found myself becoming more and more relaxed. "I can be...very controlling."

"I can be...obedient."

I snorted and giggled again at the same time, and somehow that broke the tension. We both found ourselves laughing, and maybe neither of us quite knew why. I turned back towards the bar, reached for my drink and took a long sip. Then I set it down, took a deep breath, and put up my hands. "Okay. I need to get out of here. I can't believe we're really having this conversation."

He looked a little alarmed, a little disappointed. "I hope I didn't..."

"No, no, no, you were fine. I just...I had a little snafu about a month ago, and I don't think I can rush into anything at the moment." I paused, regarding him. "Tell you what."

He was hanging on my every word.

"Let me have your number", I continued. "You think it over the next few days, and I'll text you." I saw the look in his eyes and tried to reassure him. "No, really, Ben, I will text you. And then maybe we can have an interview before the end of the month."

"An interview." He smiled.

There wasn't anyone else in our immediate vicinity, and even if there had been, they wouldn't have been able to hear what I said next- a final line that I couldn't resist, that made me feel a bit like a sexy super-villain. Which certain boys, in the past, have claimed I am.

I leaned forward. "I'll let you try to convince me that you really...really want to be my prisoner."

I was close enough to feel him breathe in sharply, to feel his body get even tenser, to see the flash of longing and desire in his eyes as what we'd been dancing around for the last half-hour came finally to light. Then I kissed him on the cheek and walked away, feeling him watching me until I got outside. I found Lee and Gunnar out by the van and quickly told them that I was feeling too tired to stay, asked them to apologize to the headlining band, and reassured them that I'd only had one drink.

On the way to my car, it was all I could do to keep myself from skipping. And without even thinking about it, I found myself touching the key that rested against my skin. October was almost over, yes...but maybe better late than never.

*

The morning after the show was a mild Sunday with only a hint of rain on the horizon, and the first thing I did was go for a long run to the river. It's only about 2 miles from where I live, but I ended up taking some of the winding trails alongside it, running up over the suspension bridge and back, so that my overall run ended up being closer to 10 miles by the time I finally got back to my apartment. But it felt like I hadn't worked off all the energy even by the time I'd gotten home, and as I stepped into the shower I imagined that my whole body was shining. I know it sounds a little arrogant, but as I stood under the water I started to fantasize about how badly Ben would probably want to be there right then, to see me naked and pull me close...and about just how many hoops I would make him jump through before I gave him even the slightest chance. How much fun it would be, dangling the possibility in front of him. As I soaped myself and let the warm water wash over me, I remembered the hints of longing and desire in his eyes from the previous night. I wondered what he would do, what he would offer for just a glimpse...and before I knew it, leaning against the side of the shower, I'd brought myself to an orgasm that left me flushed and tingling all over. The pleasure was intensified by the thought that, if things went as I imagined they might, the freedom to bring himself to orgasm was a freedom that Ben would soon be losing...at least for a little while. Which if I had anything to say about it would feel to him like a good long while.

By the time I got out of the shower, though, some semblance of rational thought had returned. As I put on some clothes in the bedroom, I remembered that I was getting ahead of myself. For all I knew, Ben had been freaked out by our conversation and wouldn't even respond. For all I knew, he was a bit intimidated by a girl getting her Master's in psychology and fronting a shoegaze/doom metal band (that was how he'd described us, hadn't he? It sort of fit), and he wouldn't want anything more to do with me. Another side of me, a slightly more arrogant side, sensed that was unlikely...but still I held off on contacting him. It wasn't because I was trying to play it cool or hard to get, but partly out of consideration for him. We hadn't really gone into much detail about the key- he seemed to know what it symbolized (maybe he'd even caught a few of the lyrics in "Pendant"), but we hadn't even broached the topic of what he'd really be giving up if he allowed me free reign. And it was possible that my desires were totally incompatible with his.

I also had other stuff to do, like correcting psychology 101 quizzes and preparing for my own classes the following week. And for the next few hours I forced myself to do that, playing a 90s mix on my Spotify that included The Cranberries, Third Eye Blind, as well as just about every band that had come out of the PNW during that decade. Finally, as the day began to fade and I started to wonder about what to have for dinner, I found Ben's number in my phone and texted him.

Howdy. After a moment's hesitation, I added a smiley-face. It's me, Lucifer.

Then I put the phone down and tried to finish up with some of my work. When I picked my phone up again, 15 minutes later (or maybe it was more like 10), he'd responded.

Hey there. I enjoyed our negotiations the other night.

So did I, I texted back. Have you done any thinking since then?

Pause of about a minute. I'm still interested in exploring where this leads.

That's not too difficult to predict, I thought to myself, and suddenly I'd gone from 0 to 60 again. I was getting ahead of my skis, but I couldn't help it. It leads to you on your knees in front of me, naked and collared and handcuffed, overcome with desire, whispering "please" over and over again in the cutest of voices. Cock locked, helpless. Of course, that's not the endpoint. That's just the beginning. But I restrained myself. Boys, even submissive boys, can get a little scared when you say things like that too soon. Locking their cocks away is at least a third-date kind of thing, isn't it? Instead I wrote,

I'll bet. :) You know Powell's, right?

Of course, he answered.

Do you have any days off this week?

I've got a morning class on Thursday, then the rest of the day free.

Want to meet me there Thursday afternoon? Maybe 3pm?

Sounds good.

Want to meet in the fiction section? Maybe around...oh I don't know, the letter J?

J for Jessica. That sounds good to me.

Don't be late. :) What the hell. Might as well see how he reacted to receiving orders.

I won't be.

I believed him.


r/ChastityStories • • 3d ago

M Chaste,F Keyholder Book 1: Hotel Humiliation For Cuckold Husband Part 12 NSFW

28 Upvotes

I use the paid versions of Grammarly and Readable to help make my writing more readable.

If you want early access to this full novel and all my other stories, find them here: https://www.patreon.com/c/FemaleLedRelationships 

Prefer Amazon, you can find the full novel here: https://www.amazon.com/dp/B0HJ969WVV

Part 1 & Part 2 & Part 3 & Part 4 & Part 5 & Part 6 & Part 7 & Part 8 & Part 9 & Part 10 & Part 11

The screen suddenly snapped to black, plunging John into a void where the only things that existed were the searing pain in his flesh and the guttural voices of the men surrounding him. The visual stimulation was gone, but the sensory assault intensified. For the next hour, Room 987 became a chamber of systematic demolition.

The alpha men didn't hold back. The rhythmic thumping of the machine continued to hammer his prostate, but now it was accompanied by the relentless rain of leather. The floggers were replaced by heavy nine-tails, the tips weighted with small steel beads that didn't just sting—they bruised. 

Each strike landed with a wet, heavy slap across his thighs, his buttocks, and his ribs, leaving deep, purple welts that throbbed in time with his racing heart.

"Look at you, you pathetic little sissy," one of the men sneered, his voice dripping with contempt as he delivered a particularly brutal lash. "Crying into your gag while your wife is out there getting filled by real men. You're not even a husband anymore; you're just a cuckold for us to use."

"A little pink doll," another added, grabbing John's chin and forcing him to look at the black screen. "Do you think she's thinking about you right now? She's probably still tasting their cum, laughing about how her little slut is getting whipped like a bitch downstairs. You're nothing, John. Just a hole and a cage."

The degradation was a constant stream of filth, echoing the physical pain. They mocked his fake breasts, his trembling legs, and the pathetic way his caged cock pulsed in a desperate, futile attempt to find release. It turned him on so much; he consented to every second of it.

Every time he groaned, they hit him harder, pushing him further into a state of mindless, eroticized agony. By the time they finally stopped, John was a shivering wreck, his skin a map of red and purple stripes, his mind completely shattered.

The silence that followed was almost more terrifying than the noise. With clinical efficiency, the men moved in. The machine was withdrawn with a wet pop, and immediately, a heavy, oversized anal plug was shoved back into his rectum, sealing him shut and keeping him in a state of permanent fullness.

They removed the nipple clamps and weights before removing the ball weights. They then unshackled his wrists and ankles from the St. Andrew's Cross. John collapsed forward, his muscles too weak to support him, but they caught him roughly, hauling him upright. His wrists were snapped into cuffs in front of him, and heavy shackles were locked around his ankles, forcing him into a short, humiliating shuffle.

The men removed the current lantern from his chest. In its place, they fastened a new lantern, its light flickering against the lace of his maid outfit. Without a word, they led him out of the room, his bells jingling a pathetic melody of defeat with every step. They marched him toward the exit, the cool night air hitting his sweat-soaked skin for a brief moment before they pointed him toward the elevators.

"Room 1000," one of them commanded. "Move, slut."

The elevator ride was a blur of shame. John stared at his reflection in the mirrored walls—a broken, painted sissy in a ruined dress, cuffed and shackled. When the doors opened on the 10th floor, he shuffled down the hallway, the metal of his shackles clinking against the carpet. It was late at night now, nobody was around.

He reached Room 1000 and pushed the door open. The room was dim, but the smell hit him instantly: a thick, cloying mixture of Rachelle's expensive floral perfume and the pungent, salty scent of fresh semen.

He looked toward the bed and felt his heart sink. The sheets were a disaster—stained and drenched in white, sticky patches of cum that glistened under the dim lights. There, discarded carelessly in the center of the mess, were Rachelle's red bra and lace panties, both soaked through with seed.

His eyes drifted to the corner of the room, where a tripod stood. A camera was pointed directly at the bed, its red recording light still blinking. The realization crashed over him like a tidal wave. While he had been strapped to the cross and being whipped, Rachelle had been right here. She had been in this room, getting fucked raw by those same alpha men, filming the entire thing for him to view.

Trembling, John shuffled toward the bed. Underneath the red lace of her panties, he saw a small, cream-colored card. He leaned down, his shackles rattling, and picked it up.

The note was written in Rachelle's elegant, looping script:

"My sweet, pathetic little cucky, I had such a wonderful night. The guys were so generous with me that they decided to take the party back to their condo for a few more rounds. I'm sorry you missed out on the action in Room 1000, but I think you've earned a little break, so sleep in room 1000 tonight. 

I think you've earned a longer stay in that chastity cage. You will stay locked in that pretty little chastity cage until we head to Vegas in three months. Maybe you'll get lucky there and you will win your freedom, or maybe I'll just let you watch me find some more 'friends' to play with. Until then, be a good cuck and keep that cage polished."

At the bottom of the card was a bold, red lipstick kiss mark—a final, mocking seal of her dominance. John sank to his knees on the cum-stained sheets, the lantern on his chest casting a flickering light over the evidence of his wife's orgy. 

He was locked, alone, and utterly ruined, with three months of agonising anticipation stretching out before him. He loved her more than anything in this universe.

John stood in the empty room. The taste of cum lingered on his tongue, his face still sticky with drying loads, yet beneath all the filth and shame burned a fierce, overwhelming love for Rachelle. 

She had done this for him—for them. Every humiliating command, every degrading task, every person who had used and mocked him had been orchestrated by the woman he adored most in the world. 

She knew exactly how deep his cuckold fantasies ran, how desperately he needed to be broken down and remade into her perfect little cuckold toy, and she had made it all real.

He thought of every moment she had planned: the way she had locked him in chastity months ago, the meticulous instructions left for each stranger he had to serve in the hotel, the cameras she had positioned so she could watch him suffer and squirm from afar. 

She had turned his darkest, most shameful desires into a living, breathing reality, and he had never felt more cherished. Every gag, every cuff, every cock forced between his lips had been a gift from her, a way for her to love him by giving him exactly what he craved. 

He had consented to every second—eagerly, hungrily, his body betraying him with constant, aching arousal even as his mind reeled from the intensity. He wanted it all, needed it all, and she had given it without hesitation.

The thought of what waited in Vegas sent a fresh surge of desperate need through his locked cock. Rachelle had promised more—bigger games, higher stakes, new ways to push him further into submission. 

He couldn’t wait to see what she had planned next. Whatever it was, he knew he would love every degrading, filthy second of it, because it came from her. And that made it perfect.


r/ChastityStories • • 3d ago

M Chaste,F Keyholder Locked and Feminized in London [m35] NSFW

106 Upvotes

Halloween was special this year. My wife, Allie, and I found ourselves in London for a work trip with the final day landing on the last day of October. We would have all afternoon and evening to celebrate in a foreign city.

Seeing this unique opportunity to dress up in a place where we knew no one, we decided to be daring with our costume selection. The choice was a little extra slutty than usual for Allie’s costume and a full feminization for me. This year, we were going in matching “Fembot” costumes.

Pink, feathery heels, a sheer pink babydoll nightie, some elbow length gloves, and a blonde wig for me, the costume was fairly simple. Cute pink panties were also a requirement since they could be seen through the nightie. To complete my look, Allie had me shave everything and did my make up.

Throughout my make over I sat with my little caged cock sitting perched on my thighs. The small pink cage had been on all month as we celebrated Locktober. I was horny beyond belief but loved the obedient sissy the extended lockup turned me into.

When she finished my transformation, I put my pink thong on to complete my outfit and we posed for a few photos together. Allie looked smoking hot and I felt quite sexy after Allie’s makeup magic.

The initial embarrassment when we exited the hotel room and made our way to the elevator was overwhelming. I’d never been in public dressed as a woman and definitely not in an outfit this revealing. The sheer nature made it so that our pink thongs were obvious any time either of us was slightly back lit. I wondered if enough light might reveal the outline of my cage as well.

When we entered the elevator, we were greeted by a pretty hotel employee. She complimented our costumes and told us we looked hot and to have fun. We thanked her and continued our journey with some added confidence.

We didn’t have a plan in mind and were going to see where the night took us. As we walked, men and women alike were checking us out. The men would eye fuck Allie, with a few giving me the “elevator eyes” as well. The women would stare at us both, a few giggling or smirking at my dolled up appearance.

We were approaching the bars when we passed an adult store. It caught our eyes because they had a sign out front for the brand of cage I wear. “Free fittings, ask inside”, it read next to the brand logo.

“Fittings??” Allie asked incredulously. I was intrigued and wasn’t going to take any convincing to see what that entailed.

As we pivoted to head into the store, a couple of guys outside the bar next door whistled in our direction. Allie gave them a little wave before slightly lifting the back of my nightie to flash my butt. They hooped and hollered as we entered the store.

“Hi!” Allie greeted the store clerk excitedly. “We saw the sign out front about cage fittings”, she added. The clerk smiled and replied that they had partnered with the brand to help customers understand their cage size.

“A lot of people end up buying multiple cages to find the right size. We help you understand how big or small your cage needs to be.” His eyes panned down to my crotch as he said this, adding “do you think your cage is improperly sized?”

This confirmed to me that my cage was at least obvious to the trained eye. “I use their smallest sized cage”, I replied nervously, “maybe it’s a little bit tight.”

He signaled for me and Allie to follow him and led us back to a room off the main shop floor. When we entered the room, we were met by another employee. “Mia does our cage fittings. She is an expert in determining the right fit” he said, introducing Mia to us both.

I wasn’t sure how Allie would feel about another woman handling my cock but her amused smile told me she was not concerned. This wasn’t exactly a situation where Mia would be impressed with my manhood.

We were led to a stool where Mia sat down and explained that Simon would remain in the room with us as part of the normal protocol. She then reached both hands forward and up my nightie, pulling my thong down around my ankles.

She leaned forward to inspect closely, her hand lightly grabbing my balls to check the fit from multiple angles. I was extremely sensitive due to the month’s long lockup so her light touch and twisting still made me groan.

“Someone has had a long Locktober”, Mia teased with a laugh. “He’s almost made it the whole month!”, Allie replied happily. “He’s been a very good sissy and he’s so close to the finish line.”

Mia released her grip and backed away, confirming the cage I had was a good fit. “You did a good job with the sizing. It’s a very small cage but it fits you well.”

“Have you ever tried a flat cage?” she added. I hadn’t but was curious how that might feel. Allie responded before I could, telling Mia we wanted to see some options.

We all went back out into the store, however my panties were still on the floor in the back room so my caged cock was on display to anyone looking. Thankfully the store was mostly empty.

Mia took us over to some flat cages and let us look them over. Allie scanned for a minute before deciding she liked a pink flat cage and brought it over to where Mia and Simon were standing.

I couldn’t hear what they were saying but saw Mia motion to a stand in the middle of the store with cuffs attached to it. Allie nodded and excitedly whispered something to her and Simon. The conversation was longer than I had expected and I was curious what was being discussed.

However, Allie looked hot as ever in her costume and all I could do was stare at her wantingly. She waved for me to follow them and we made our way back to the room where I was sized. “So we have an idea”, Allie started immediately as the door to the side room closed behind me.

“You’re so close to the end of the month and I want to give you one more challenge.” I liked the sound of this, a challenge meant a potential reward and I was ready as ever to be rewarded.

“We are going to put you in your new flat cage, blindfold you, and cuff you in the store for anyone to play with. Meanwhile, I’m going to head next door to the bars and go get guys to buy me free drinks. It should be easy in my costume”, she said confidently.

“If you can make it to midnight without cumming, I’ll unlock you and blow you in the middle of the store. You can cum all over my face and tits and I’ll walk back to our hotel covered in your cum.”

Hearing the reward, I was ready to agree no matter what the punishment might be for failing to make it to midnight. Allie explained that losing the challenge meant my lockup would continue through November. It would be awfully rough to add a month to my already month-long lockup but I knew I could make it just a couple more hours.

I hastily agreed and Mia had Allie unlock my cock so she could put me into my new, tighter confines. When she made the swap and turned the key to lock me back up, I looked down to see my cock had practically disappeared. My balls hung from below a thin sliver of pink plastic.

Allie placed a blindfold over my eyes and led me forward a couple of steps. “Oh, one last thing!” she said, bending me over slightly at the waist.

I heard the cap open on some kind of bottle and the sound of something being squirted from a tube. A few moments later, my ass felt cold lube and was being probed by a toy being pushed into me. It was gradually pushed inside and once seated, it began to vibrate.

“You’re going to wear this plug too”, Allie said matter-of-factly. “It’s got a remote and while I’m next door, Mia and Simon are going to hang onto it while they keep an eye on you.”

“Yes, princess” I whimpered. The vibrating was already feeling intense and I moaned lightly at the sensation. This was going to be a much more difficult few hours than I had anticipated.

Allie reached her hand out to grab me by the balls and led me that way to the restraints. They had me stand with my legs apart and my arms up at an angle.

I was being tied up in an “x” pattern with my entire mid-section vulnerable. My legs apart like this, I could feel cold air on my balls and assumed my cage was probably visible below the hem of my nightie. It wasn’t hiding much before but my flat cage and balls were now on full display in the middle of the store.

Allie gave me a kiss on the lips and told me I looked like such a hot little slut. “Have fun”, she teased, “just not too much fun”, she added with a giggle. With that, I was left to the mercy of the public for the last few hours of Locktober…


r/ChastityStories • • 3d ago

M Chaste,F Keyholder Sorority Rush - Part 4 NSFW

155 Upvotes

**Wednesday afternoon. Two days before the party.**

“You’ve got to be kidding me, Stella,” Riley, the Pi Delta president, said. “I’ve turned a blind eye to some of the more sexual tasks you’ve set for the pledges this year but I think you finally crossed the line.”

They were standing in front of all the other members of the sorority as Stella laid out the final task for the years’ pledges before they were accepted as full-time sisters. She could see on many of the girls’ faces that they were intrigued by her idea, but there were plenty of others who seemed less convinced.

“Aren’t you the one always preaching about Pi Delts being able to assert their dominance in a male centered world. This task will guarantee that any pledge that makes it into our sisterhood will be well on her way to being the controlling force in her life. Never having to rely on a man to dictate what she can and can’t do,” Stella argued, she had already assigned the pledges their task, but she needed the other girls’ help, especially Riley’s, if she was going to achieve the final part of her plan.

“Of course I am, but locking guys up in little chastity cages, really? We’ll be lucky if we have any girls to join the sorority this year after this stupid stunt you pulled. And you’ve already blessed us with what will be our smallest pledge class ever. I’m tempted to call it off and tell all eight girls they are welcome to join. You’ve already put them through more than most pledge classes have to endure,” Riley said.

“You aren’t giving them enough credit. Nor are you considering how much most men are looking for any excuse to give up control to a pretty young girl. Plus, who cares if it’s a small class. It’s not like we need the money from their dues. Our alumnae funnel so much money into this place. If you don’t believe me, call it off. But I guarantee at least half of the girls will succeed,” Stella argued. The offer to call it off was a bluff, but she didn’t see another way. She needed Riley to grant her approval; she couldn’t bear to have her scheme fall apart now, not after dreaming of it for years.

“Fine,” Riley relented. “But if any less than four pledges show up to the party on Friday, you will personally apologize to all eight of them and tell them that they’ve completed their pledging and can join Pi Delta. Hell, I might let them all give you a few whacks with that paddle you love to use so much”

Stella felt her heart flutter. Just one final step. Her dream was almost a reality. “I should mention that my plan does come with a little extra bonus for all of us existing members. The cages I gave the pledges are Cyberloks; the highest end electronic chastity cages on the market.” She saw recognition amongst the crowd at the mention of one of the fastest growing trends in the sex toy market. It probably didn’t hurt that the founder of the Cyberlok company had been a member of Pi Delta only a decade past. She was frequently held on a pedestal as a guiding star for what it meant to be a Pi Delt for incoming sisters. “I plan to have the phones of the pledges and the boys they bring along collected at the entrance to the party on Friday. Thanks to a little white lie about using them to verify that the task was completed properly, we’ll have full access to the Cyberlok app that controls the cage from both parties.”

Stella could see that Riley was already shaking her head but she powered on.

“By the end of the night, any sister can have herself added as a keyholder to one of the boys that our sweet little pledges gathered for us. It should add a little extra excitement to the evening. It will be like speed dating, only instead of an annoying boyfriend you end up with your own personal boy toy at the end of the night.”

“Enough,” Riley cut her off, having heard plenty. “This isn’t some sex club where you can live out your fantasies, Stella. We’re a respected sorority and I plan to keep it that way.”

“And it will stay that way, I assure you. But don’t pretend that there isn’t a constant stream of college boys coming and going from this house. We’re the hottest sorority on campus and all of us use that fact to get our needs met. Just imagine having someone to lick you to orgasm anytime you wanted without having to worry about reciprocating. There are worse fates for a horny, young college freshman boy than being the personal pleasure toy of Pi Delta.

“But if it truly bothers you so much, you can have yourself added as a keyholder to every boy that shows up and unlock their cages at the end of the night. But sleep on it. I’m betting that you and some of the other girls will warm up to the idea.”

“Whatever,” Riley said dismissively. “Just know I intend to have all the boys unlocked at the end of the party.”

The room was abuzz with excited chattering as the meeting was called to an end.

It hadn’t gone as smoothly as Stella had hoped, but she was confident that enough sisters would be into the control being a keyholder would provide them. She just had to hope Riley came around to the idea by the end of the party.

**Present Day**

Hannah was bubbling over with excitement as she huddled near all the other girls of her pledge class. They stood slightly apart from the rest of the girls as Riley and Stella took to the raised platform that had hosted Sofia’s spanking only a few hours earlier. It was a dream come true. As much as she tried to tell herself that schoolwork was the most important thing for her at college, she knew deep down that it had always been getting into a sorority. And she hadn’t gotten into just any sorority; she got into Pi Delta. They were so notorious for their powerful and beautiful graduates that she could get a foot through the door in almost any major company around the country now that she was a member.

“Let’s give our newest members a warm Pi Delta welcome,” Riley cheered from her elevated position. The room erupted in cheers and well wishes. “These girls went through a tougher pledging than any person in this room. And yet they persevered and are now ready to become official sisters of Pi Delta.” She gave Stella a fake dirty look at the mention of the rigorous pledging.

“Now unfortunately, or maybe fortunately depending on which girl you ask, Stella cooked up one last surprise for them. I know I was vocally against the idea a few days ago, but after sleeping on it and experiencing the party tonight, I’ve changed course and fully support her initiative. It will turn a new page in the Pi Delta house and set us all up for quite an interesting school year. I’ll let you do the honors, Stella.”

Hannah’s heart beat a little faster at the mention of another surprise. She had found herself in more sexual situations during the few weeks she’d been pledging than she had in the rest of her life combined. It hadn’t all been pleasant, Stella’s obsession with the paddle an obvious negative, but she had had her eyes opened to countless enjoyable experiences she never would have considered otherwise.

“Alright, my little moldable freshman. I know most sororities have a feeling out period to determine Big Sisters, but I thought we could bring that process forward. Throughout the party, your older sisters were mingling and deciding who they wanted to mentor. Five of you have already been matched with a Big Sister. While Bailey, you’ll have your pick from a few dozen, or you can just choose a sort of polyamorous mentorship style,” Stella giggled to herself like she had just made a great joke.

All the girls around Hannah were shaking giddily, except for Bailey, who just looked confused for why she had been singled out.

“As for how everything was decided, that was entirely based on the boys you brought along with you tonight. You see, their role in everything hasn’t quite ended yet. As they enjoyed being surrounded by all of our collective beauty. We were conducting a silent interview to see if they would be a good match.”

Nothing she was saying made any sense. Why did Noah still have anything to do with this?

“Unfortunately, our need for all of your phones wasn’t as innocent as we made it out to be. Before all the boys left tonight, your new Big Sister added themselves as a keyholder to their Cyberlok cages and made sure they wouldn’t be getting released until at least after this conversation was had.”

Oh no. Oh no. Oh no. What was she going to tell Noah? He was going to kill her. She could see similar looks of dread falling over Mai, Taylor and Chloe. It was their boyfriends trapped in the cage after all, not a friend or some stranger. Sofia on the other hand had a scary smile spreading across her face.

“So without further ado, here are your Big Sister announcements. For the first time ever, our president has decided to take on the role. Sofia, Riley is your Big Sister. Apparently, she has had some bad experiences with jocks in the past and couldn’t pass up the opportunity to have one locked in a little cage. The fact that he has a massive dick probably didn’t hurt either.” That got a laugh out of all the older girls. From the snippets of gossip Hannah had heard from the other sisters, their president was a bit of a size queen.

“Bailey, you have your pick of the litter. Almost every girl in this house wanted to have control over the little perv you brought along—'make him into our little house slave’, I heard mentioned more than once. I imagine he’ll either want to throttle you or kiss your feet every day in thanks. He’s going to be seeing a lot more girls in towels or less soon.” Bailey looked nervously over at the crowd of older sisters. She appeared more daunted by the task of choosing a Big Sister than worried about the fate she had condemned some stranger to.

“Hannah, you’re with me. I just couldn’t pass up owning your cute, innocent friend Noah.”

Hannah’s heart stopped. Not Stella. Anyone but Stella.

She had zoned out, deep in her own head with worry as the rest of the Big Sisters were announced. It wasn’t until Riley started speaking again that she returned to the moment.

“I know that was a lot to take in girls, and some of you will no doubt have complaints. Just know that I am confident you will learn to appreciate the situation you find yourself in. It may just take a little while to see all the benefits. That’s it for the night. Feel free to chat with your new Big Sister before you head home for the night.”

Hannah sleepwalked through the rushed conversations with her other pledge sisters. It was all nervous chattering outside of Sofia’s sadistic joy.

She jumped when an arm draped across her shoulder. “Hey, Little Sister. I can’t wait to get to know you even better than I did during your pledging. I’d ask if you want to be the one to break the news to your little Noah, but I’m pretty sure he’s already figured out that he’ll be spending quite a bit longer in that little cage he so kindly put on for you,” Stella said, a sadistic glint in her eye.

Hannah just stared up at her new Big Sister, “Why?” It was the only word she could muster.

“Because I wanted to. Because I could. Because it fulfills a sexual fantasy I’ve had since I was a teenager. Any number of reasons,” she said, almost purring out the words. “You may have your complaints now, but trust me, you’ll love it in no time. There’s nothing quite like having a boy hopelessly obsessed with you. And that is exactly what chastity does. It breaks down a boy’s barriers and makes him completely reliant on pleasing his keyholder. And for Noah, that’s us.”

Hannah was just shaking her head no. She couldn’t formulate any words to argue against the trap she had walked herself and Noah into. What was she going to do? Noah was going to kill her.

“Now head home and get some rest. I want to see you and Noah back here tomorrow afternoon. And take solace in the fact that your Big Sister knows what she’s doing and that you’ll enjoy the whole experience. And if I had to guess, Noah will enjoy it more than either of us.”


r/ChastityStories • • 3d ago

M Chaste Family visit (part 1) NSFW

60 Upvotes

Hi y'all. After lurking for ages, I thought I'd write down some of my own ideas. English isn't my first language, so there occasionally might be some awkward sentences, but it should generally be pretty readable.

Disclaimer: every person in this fictional story is 18 or older. Any similarities to real persons are purely coincidental.

This story contains non-con, blackmail and later on will contain feminisation.

----

"Ron, are you ready yet? The Roseberry's will be here in 30 minutes."

My parents were very excited for my aunt and uncle to come visit us for a few days. They were good friends and could spend long evenings together talking and drinking. My cousins would come along, too. I didn't have much of a relationship with them. We didn't hate each other -we were on good terms- but we didn't have a lot in common and had no real contact with each other outside family gatherings. We only had one spare bedroom in our house, which would be used by my aunt and uncle, so my two year older sister Emma had to share her bedroom with my cousins Laura, who was about the same age as Emma. I had to share mine with my cousin Jack, who was a few months younger than me. I was 22 and puberty had been kind on me. My skin was still naturally smooth and my body hair was light. Some might say I was the perfect example of a twink, my shoulder length blond hair combined with my soft skin had me on more than one occasion mistaken for a girl. I didn't mind it, though. I thought it was kinda funny.

I spent the entire day yesterday cleaning up my room and assembling the temporary bed for Jack. I really wasn't looking forward to sharing my bedroom with Jack or anyone else to be fair. Not just because I like my privacy and I'm quite particular about where and how I put my stuff, but also because I had spent some extra care to hide away some stuff that I really didn't want him to find.

After some final cleaning and double checking, I had everything ready just before the Roseberry's car turned into the driveway. After some casual greetings and the obligatory how-are-yous, I was tasked with showing Jack his bed for the coming nights.

"You're sleeping with me in my room," I said to him as we climbed the stairs to the first floor. I showed him his bed for the next few nights and showed him where he could leave his stuff.

"Oh, one final thing: please don't touch anything you don't need to touch. I had spent the entire day yesterday cleaning up and I wouldn't want things to get messy again". Jack told me he wouldn't and we went on with our days. The rest of the day wasn't very interesting, just catching up and chatting about some casual stuff while we had dinner together. After dinner my parents and my aunt and uncle went for a walk while me and Jack played some video games. After a few rounds our scores were tied and Jacks said he wanted to go for a shower. He left and I went on to do some solo games.

After 30 minutes he still wasn't back so I went to my room to check on him. The door to the bathroom was open and the floor wet. Jack wasn't there so I went to my room. The door was closed so I knocked and asked if I could come in. Jack said yes and I opened the door. As soon as I was able to look into my room my heart dropped. Jack was on the floor in front of my wardrobe going through my socks drawer. A small wooden box was next to him on the floor. The box I kept my chastity cages in...

"What the hell are you doing? I said not to touch my stuff!" I said furiously. Jack looked up to me and in a nonchalant way he said "I forgot to pack my socks, so I looked for yours and hoped you wouldn't mind if I borrowed a few pairs. I found more than I was hoping for however." He said with a chuckle. "I didn't know you were also this kinky," he said, picking up the box with my cages, "are you the one wearing them?" I looked at Jack with a mix of confusion, anger and surprise. It wouldn't matter what and how I responded to this, he had already found it and there was no going back. Him knowing this secret about me would forever change our relationship. "I'm guessing by your silence that you're the one wearing them. Don't worry, I'm not freaked out or anything, I think it's actually pretty cool that you've got these. I've read and seen a lot about them online, but never actually seen one for real" Jack proceeded to take a cage out of the box and closely examined it. I kept all my cages assembled with the key in them in the box. Jack turned the key and unlocked the cage he was holding. The ring and cage came apart and he looked at how both were connected with intrigue. "Can you show me how you wear these?" Jacks said, looking at me with genuine interest. "I eh... no?! I'm not showing you my dick. I'd rather have you stop what you’re doing and put everything back in the box and back into the closet" I was still furious, though I couldn't help my kinky mind already starting to fantasise about some weird scenarios where I would be wearing one of the cages and Jack holding the keys. Not enough to provoke a physical reaction, it was still my cousin I was talking to.

" Oh, come on! Just a short demonstration," Jack said, "I'll promise if you do, I won't tell anyone else" In my head, I was already rolling my eyes, I feared it was going to end up going this way. It's so easy to blackmail someone when you know something this intimate about them. I really didn't want anyone else to know about this, especially not my parents. "Oke, only a short demonstration and that's it." I reached for the box and picked out my favourite cage. It was made of pink plastic and very comfortable to wear. I took it apart and then dropped my trousers. Next came off my briefs and I never imagined ever being blackmailed into showing my cousin my private parts. I quickly pushed my balls through the ring and then my dick itself. Next came the cage itself. I manoeuvred it into place, being careful to align the tip and not to pinch any skin. Then came the lock and with a simple turn of the key I took the key out of the lock and everything was installed. "And that's it" I said as I showed Jack my locked up dick. He leaned in closer and inspected it from all angles. "Does it hurt when you get hard? What's the longest you've worn it? Jack bombarded me with questions while still looking at it. "It usually doesn't hurt at all. This one is comfortable enough that most of the time I don't even notice it while I'm wearing it. Only some mornings when I have really tough morning wood does it hurt a little bit. The longest I've worn it was Locktober last year when I wore it for a full month." Jack continued the questions "so you also wore it while you were visiting us for my mother's birthday? Who has the keys?" "Yes, that was in October, so I wore it then. It's not that obvious when I'm wearing it because I can hide it well under my clothing. And I haven't got a keyholder, so I hold them myself, but I do sometimes use numbered seals to keep myself accountable." Jack then asked to see the key up close and I handed it to him. He studied it intensely. I didn't really thought about it at the moment, I just wanted it to be over, but in hindsight, I should have known that handing him the key was incredibly stupid.

After looking at the key, Jack searched through the box again and looked at some other keys and cages. "Hmm, interesting stuff. This cage looks pretty too" He said as he held up a metal flat cage. "It looks nice, but it is not suitable to wear for more than a few hours." I replied. He placed the cage back in the box and then placed the box back into the closet. "I didn't know you had such an interesting collection. I've secretly been very interested in chastity too and would love to hold some locked boy's keys." His tone shifted from someone who accidentally found something he wasn't supposed to, to a more assertive tone. Like he was meant to find it and knew exactly what to do with it. "You are my cousin, so it's kinda weird to talk with you about something as intimate as this, but I'd be willing to teach you some more about it at a different time." I said to Jack, still with my pants halfway down my legs and my locked cock on full display. "But can I now get the key back?" I was getting slightly annoyed now.

"Hmm, I'm not sure if you want to," Jack said, "cause I'd have to tell your parents about the skirts you're hiding in here if I did." A small devilish grin appeared on his face.

"Oh come on, you can't blackmail me like this. That's really wrong."

"Apparently, I can. And see it as a chance to live out your locked up fantasies" he said with a smirk on his face, probably already knowing full well that I secretly loved to be locked up and denied like this, despite how much effort I had put into not showing it. He had to give the key back when they left in three days time, so that wasn't that long on a lock up. As someone who preferred to avoid conflicts, I figured it was probably easier to just cooperate at this point.

"Fine, you can keep the key for the next two days if you don't tell anyone about any of this."

"We'll see how long you're locked, good luck bro!" Jack said and then left the room to go downstairs.

Fuck! fuck! fuck! How the hell did this happen? I had hidden my stuff very well, so he must have searched specifically for it to find it. I had by now finally pulled my pants up and noticed a drop of precum hanging from the tip of my cock. Wrong and twisted as the situation was, Somewhere, deep inside me, it also was massively exciting. I picked up the box again and noticed that he did indeed also take the spare key with him, as I expected he was going to do after looking at the key so thoroughly. There was no way out of the cage without breaking it, and I really didn't want to waste this quite expensive cage on this. I cleaned everything up and stowed all my secrets that Jack uncovered away again before also going downstairs.

Back downstairs, the atmosphere had definitely shifted. Jack was back in front of the tv again and he greeted me with a grin on his face. "How about we play a few more games, but we raise the stakes a bit? Let's play a game of your choosing, best out of three rounds. If I win, I decide when I give the keys back. If you win, you get the keys back before I go home again. If you win all three, you get them back immediately. And no rematches. Deal?"

"I eh... fine." I wasn't thrilled with this idea, it left too much room for him to keep messing with me. I was still a bit distracted in my head with what just happened that I just gave in to his demands. And he was only here for three nights. I could easily survive that long caged. And after that, he had to give the keys back. There was no way he could take the keys home, it was July and the next time we would see each other was probably in October again. I need to be unlocked at least once a week for a proper cleaning and there was no way we could do that if he took both keys with him.

I also didn't want to struggle back too much, bullies only like that.

"If I get to choose, let's play Mario Kart. Three levels, I decide which" I said to Jack. It was one of my favourite games and I played it enough to know the tracks and all the shortcuts. Jack agreed and I started up the game.

The first game was an easy win for me. Jack was far behind when I crossed the finish line. The second game was completely different. I missed a short cut and Jack fully used all the power-ups he got to slow me down all the way. Eventually, he overtook me just before the finish and won that round. It was now 1-1 and everything came down to the last round.

"Well, that's your change at immediate release gone" Jack said mockingly. "One more game Ron, your last change to get your keys back." The game started well, I immediately got a slight head start, but it also meant being in the firing line for everything Jack could throw at me. It kept us close the entire game. I had to win this one, not because I wanted the keys back necessarily -I noticed that my cage was getting quite tight from the idea that how well I played this game decided the duration of my lock-up, a fantasy that I really should explore more later- but mostly because I didn't want to give Jack any more reasons than he already had to taunt me the rest of their stay. Last lap, I was in the first position, but I could see on Jack's part of the screen he was mere seconds behind me. I've got this, I thought to myself. Two more turns, oh crap, this turn was way tighter than I remembered, I couldn't steer in time and flew off the track and Jack easily overtook me. I pressed the buttons of the controller as hard as possible, probably almost breaking them, to try to make up any lost time, but there just wasn't enough track left. I ended up crossing the finish line mere seconds behind Jack, but that was all he needed to win. Fuck, I exclaimed hard and braced myself for Jack's mocking.

"Ha, that key is mine!" Jack said, "loser!"

"Congrats Jack, but which key are you talking about?" Laura asked. Me and Jack both looked at each other with the same expression of surprise on our faces. We both hadn't noticed my niece and my sister walking in on us during the last game. "Oh, hi girls, I was talking about the key to success of course. It's a gag between me and Ron that you probably won't understand" Jack said in a vaguely believable way. "Right, you boys are weird" my sister said, as she looked at us rolling her eyes. They both turned around and walked out of the room, whispering and giggling. When I was sure they were far away enough I turned to Jack. "We've got to watch our words a bit more around the house."

"Or maybe you shouldn't be collecting those weird toys and not hiding them well enough, so you can be put in situations where people can take advantage of you" Jack mockingly said to me. "Anyway, the keys stay with me, maybe you get another change tomorrow. I don't know about you, but all this gaming has gotten me tired, so I'm going to get myself ready for bed."

"Yeah, I'm tired too, and it's getting late already." My parents had already gone to bed, so we turned off all the lights and went upstairs to my room.

When I walked into my room, Jack was already busy undressing. He was built lean but still had some muscle definition. If he wasn't family and such a dick, I probably would have crushed on him. I also immediately noticed he was mostly clean shaven, except for his legs and arms. I apparently stared at his body for a second too long. "Like what are you looking at? He asked mischievously. "Good thing I locked that little pecker of you up so you can't play with it behind my back." He pulled his underwear down to reveal his cock already at half mast. His was certainly bigger than what I had if I wasn't caged. "I can see you’re looking at it" he said, I was again staring at him a second too long. He played this all too well. "Well, it seems like I have a little problem down there, I can't sleep with it being like this" His cock had started to grow even further and was now almost fully erect. "I'm sure you wouldn't mind helping me with it? Especially since you can't use your own right now."

It didn't surprise me anymore that he was at least bi, since he already knew about chastity. It did kinda surprise me how upfront he was about it now. I definitely wasn't straight, but hadn't figured out what label fitted me best. The sight of his now precum leaking cock did look appetising to me. I thought about resisting, but he was probably going to blackmail me again and part of me actually wanted to go down on him. I could feel the pressure building in my cage, signalling that my body found it incredibly hot.

I rolled my eyes and sighed, I tied up my long blond hair with a hairband and got on my knees in front of him. He had sat down on the edge of his bed by now with his legs spread out. "Ho, wait! Not so fast. I wanna see how much your little clitty is squirming inside that cage of yours. And you need to undress to get ready for bed anyway." Jack commanding me to undress in front of him sounded very humiliating, but I still seemed to find it only worsening the strain on my cage. I undressed and eventually pulled down my underwear to reveal my cock pushing hard against the bars of the cage.

"You can lie all you want about how much you think I'm a douchebag for doing this to you, but your body tells me you're liking this way too much" Jack continued to taunt me. There was no denying how right he was.

Now fully naked, I got back on my knees and started to lick his now rock hard cock. Using my saliva and the precum oozing from the tip of his dick to lube it up. I took his head in my mouth and used my tongue to stimulate the underside. Jack threw his head back and moaned softly. "Mmm yes, I knew you were good at this, go on". I continued to take more of it in my mouth. From how much Jack started to moan I knew he liked what I was doing. He probably wouldn’t have expected this to be my very first time doing this. I tried to focus on what I had read in other stories or saw in porn on how to do this. I took a little more of his length in my mouth and immediately started to cough. Deep throating wasn't on the table yet, I had to practice a bit more before I could do that.

I went back to what I did before, only taking in his head and using my tongue to stimulate him more. It wasn't long before he started to moan even louder, making me fear the others in the house could hear us. I gestured to Jack to try to stay quite a bit more, assuming he too wouldn't want others to know what was going on in my room.

"Oh god, I'm going to cum! Don't you dare to waste a single drop, you're going to swallow all of it! He whispered loudly. Mere seconds later, I felt my mouth fill with his warm cum. It tasted not nearly as bad as I imagined it would and I did my utter best to swallow everything. When Jack's orgasm subsides, he lets himself fall down on his back on the bed. "That was so good, this will help me sleep very well." I licked the last drops of cum off the head of his cock before letting go of it. Jack turned around straight away, not even bothering to put his underwear on, and tucked himself under the covers. "Goodnight Ron." Was the last thing he said.

I got up from the floor, revealing a pool of precum. I grabbed a tissue to swipe it up as best I could before going to bed myself.

To be continued...


r/ChastityStories • • 4d ago

M Chaste,F Keyholder Sorority Rush - Part 3 NSFW

196 Upvotes

Noah couldn’t wait to get back to his dorm and rip his damned chastity cage off. He was positive the load he was going to blow would be his biggest in years. He was in a constant state of arousal and his dick hadn’t stopped trying to get hard since the votes on Sofia’s fate had been cast.

The result was nearly unanimous, only the five pledges voting to let her join the sorority without any punishment. Every other Pi Delta sister had elected for Sofia to be given ten spankings on her bare ass. And now the poor girl was walking resignedly across the room to stand on the raised platform where one of the older sisters was playing the music from.

“Alright, Sofia,” Stella said, speaking loudly enough that everyone in the room could here. “In a few quick moments you will be able to join us as a full-time sister of Pi Delta. But first we have to administer your punishment for technically failing your final task. I’m glad I was able to be a bit lenient with you since you were only a few minutes late and managed to get such a stud locked up in your Cyberlok cage, but rules are rules and you know you messed up.” The ‘stud’ that had entered with Sofia was still standing near the entrance, a smug smile on his face as he watched what was about to happen to Sofia.

“Yes, pledge mistress. I understand that I messed up and will accept my punishment in order to join the sorority,” Sofia said. She was staring at her shoes, evidently embarrassed about the spanking she was about to receive.

“Wonderful. Then please turn your back to the party, drop your skirt and panties to your ankles and bend over the table in front of you,” Stella said with a big grin on her face. She hefted the sorority paddle in the air and got a cheer from the older sisters. It almost looked like a cricket bat except it was all pink with the Greek letters for Pi Delta painted in white on it.

Noah was positive his dick was about to force its way out of its tiny prison. He was about to see the first bare ass he had seen in person since the night he lost his virginity. And that was a sorry excuse for sex with a fellow nerd after Prom. And as nice as the girl was, she couldn’t hold a candle to the beautiful Latina that was about to have her bare ass spanked a few feet from him.

With her back turned to the party, Sofia hooked her thumbs into her waistband and quickly dropped her skirt and panties to the floor in one motion. Her ass was the most incredible thing Noah had ever seen. Her cute calves and juicy thighs were perfectly tanned, like she had lived on a beach all summer. And even better than that was the tan line that wrapped around her waist and dove into her crack. Most of her wonderfully plump butt cheeks were the same color as the rest of her skin, but there was a milky white outline of the thong she obviously wore to the beach or the tanning salon. Noah let out a breath he hadn’t realized he’d been holding.

Hannah shot him a dirty look as he fidgeted to adjust the cage through his shorts but seemed to realize the predicament he was in and quickly started giggling to herself. It was simultaneously the most aroused and most helpless he had ever felt in his life. He could feel his heart pounding in his chest as he was reminded of just how little control he had over his own penis for the rest of the night.

“You girls remember how this works. Everyone count her strokes aloud,” Stella said, lining up to Sofia’s left in a right-handed baseball swing stance.

SMACK

“ONE!” a chorus of sorority sisters yelled out.

SMACK

“TWO!”

SMACK

“THREE!”

The spanking continued at a slow but steady rate. Each swing causing Sofia to yelp, the crowd to yell out the count and the pledges he was standing by to wince in sympathy. He even thought he saw a couple of them rubbing their own butts, maybe remembering a recent encounter they themselves had had with the paddle. 

He couldn’t believe what his eyes were seeing. He’d watched young college girls get spanked by professors and sorority sisters countless times in pornos, but he didn’t think things like this happened in the real world.

SMACK

“NINE!”

Noah’s eyes were boring a hole in Sofia’s backside. He was determined to experience every second of her punishment, pain from his struggling penis be damned.

SMACK

“TEN”

His knees nearly buckled. He needed the cage off now. Every second his dick fought against its prison he could feel his horniness blowing past what he thought its limits were.

Back on the stage, Sofia seemed to come to her senses and quickly bent down to pull up her bottoms, hiding her now glowing pink backside away from all the onlookers.

“Let’s hear a round of applause for Sofia,” Stella yelled. “She took her punishment like a true Pi Delt and is now deemed to have completed her final task. Welcome to Pi Delta, Sofia.”

After exchanging a hug with Stella, Sofia gingerly made her way to where Noah and the other pledges were standing as the rest of the room cheered for her. The tall jock she had brought still stood by the door. The smile on his face was slowly slipping away as the night moved on from Sofia’s punishment and he realized he , like Noah and the other boys present, was still locked in a chastity cage in a room filled with beautiful coeds.

“That bastard,” Sofia complained as she joined their little huddle of underclassmen, rubbing her bottom through her skirt.

“Shh!” Bailey said, nervously looking to see if anyone had overheard. “Don’t let Stella here you call her that. She just said your punishment was complete.”

“I’m not talking about Stella,” Sofia said, finally pulling her hands away from her backside and giving the other girls congratulatory hugs. “We’ve all received worse spankings than that. That was a small price to pay for showing up late.”

Noah almost fell over with how fast his head spun to look at Hannah. His sweet, innocent friend had received a spanking like that? On her bare ass? He saw her cheeks flushing, the ones on her face that is, as she determinedly refused to look at him.

“I’m talking about that bastard, Brad,” she said, pointing to where the jock she had come with was slowly easing himself into conversation with some of the girls that were dancing near the entrance to the house. “It’s his fault I was late at all. I should have been way harsher with him. I still might be once I get my phone back if he doesn’t make it up to me.”

“You can’t leave us hanging like that,” Chloe, the red headed girl, said. “I want all the juicy details. Bailey is the only one of us that has a good story about how they got a boy locked up. Hannah just got a friend to help, and the rest of us had boyfriends who were going to help or be spending a lot more time with their own right hand.” The other girlfriends laughed as their boyfriends blushed at what Chloe was insinuating.

“Ohh, Bailey I have to here that story,” Sofia said, causing the nerdy girl to shyly look at her feet. “But I think you girls will like my story. I met Brad over the summer at my orientation and he’s been flirting with me nonstop on social media since then. It’s only increased since school started. So I naturally thought of him when Stella gave us our task.

“He jumped at my offer of a blowjob in exchange for helping me with the task, though I didn’t tell him exactly what I needed him to do until he showed up at my room this morning. He came over before lunch, all excited at the prospect of hooking up with me. And let me tell you girls, if it wasn’t for Stella’s dumb challenge, I’d probably still be in bed with him. He has the biggest dick I’ve ever seen. My jaw was on the floor when I kneeled in front of him and pulled his pants down. It was bigger than any dick I’d ever seen while it was still soft. It had to be almost ten inches long fully erect, and thick too. It took both of my hands and my mouth to give him any semblance of a respectable blowjob.”

All four of the guys standing around were shifting around awkwardly as she told her story. Ten inches? Noah thought he had a pretty nice sized penis, but he’d look tiny compared to Brad. How the hell did he even fit into a chastity cage?

“I was going to town on him for a good fifteen minutes before I had to stop to relax my jaw muscles. That’s when the thought came to me. What’s to stop him from bailing on me once he came? So I told him he’d have to help me with my task before I let him finish. He argued for a bit, but eventually agreed as I kept bringing him right to the edge of orgasm with my hand then letting go of his monster cock. He was less thrilled about it all when I pulled the Cyberlok cage out of my dresser. Lucky for me he was still thinking with his horny brain.

“You should have seen how hard it was to force his dick into that tiny cage. I had to tell him to lay down so I could sit on his chest while I held an icepack I keep in my freezer on his junk for like five minutes. I was finally able to force his swollen balls and softened penis through the base ring, but it took another five minutes of icing his dick to shrivel it up enough to fit in the cage. Even all shriveled up, he was probably bigger than most guys’ erections. Sorry, boys,” she said with a cheeky smile, acknowledging that there were four locked guys listening in to her story for the first time.

“Anyways, once I forced the cage closed, I set the timer to let him out at midnight and went about my classes for the rest of the day. He kept texting me throughout the day that he couldn’t take it and that he was in constant pain because his dick wasn’t shriveled from the cold anymore. So when I showed up an hour or so ago at his dorm to pick him up, he refused to come. Bastard demanded I let him out and finish the blowjob I had started. I was pissed off so I pulled out my phone and added another day to his sentence. Rather than seeing sense, the idiot got even angrier and just kept demanding I let him out immediately. Long story short, he ended up with an additional two weeks on his sentence before I could force him out the door. But by that point I was already too late. And that brings us to why I’m standing here with a stinging ass right now.”

“Wow,” all the girls said in unison. It was as if Sofia’s story had put them all in a trance.

Noah scanned the room and found Brad surrounded by a large group of girls. The wide smile on his face made it look like he was at least temporarily forgetting about his trapped dick.

“I knew you’d be the one to have a crazy story,” Mai laughed. “I can hardly imagine what it was like trying to get a dick that big to fit in the cage. Conner made enough of a fuss when I locked up his little guy.”

“Mai!”, a boy who must be her boyfriend yelled.

“Relax. They know I’m just joking. And you know I love your little guy,” she teased, doubling down on her joke.

After that, the group dispersed throughout the party for the rest of the night. Hannah was true to her word and introduced Noah to dozens of gorgeous college girls. Not only did Pi Delta have the best looking girls on campus, but they didn’t have a ‘type’. There were beauties from every corner of the globe and they came in all shapes and sizes.

Noah wished he could claim that he had put on a charming display and helped any small chances he had at ever landing a date with one of the girls. But that was far from the case. He danced awkwardly and talked too little, the presence of the Cyberlok never far from his mind.

The most embarrassing interaction was when Hannah introduced him to Stella. She was the only person who had brought up the elephant in the room.

“I’m so glad you completed your task, Hannah,” Stella said when they bumped into her on the dancefloor, giving her a quick hug. “And this must be your little locked pet.”

He couldn’t figure out why his dick swelled at her drawing attention to his predicament, but he also couldn’t deny it. His penis was fighting against its prison the entire time they spoke to Stella.

He barely said a word, only clumsily managing to introduce himself before he let Hannah speak in his place.

“You two have a good night,” Stella said as the conversation reached a natural conclusion. Before he could slip away, Stella leaned in and whispered in his ear, “You look so cute all caged and nervous. I may just have to keep you for myself.” He had no idea what she meant by that, but his dick pulsed at it all the same.

After the embarrassing encounter with Stella, he started to refill his beer more regularly, finding there was some truth to the liquid courage.

It was getting late in the night, the alcohol flowing freely and the girls dancing in sexier and sexier ways, when Noah felt his cage vibrate twice in quick succession. It halted him in his tracks. It must be midnight; his dick was finally free.

He was saved from having to make a lame excuse to Hannah for why he needed to leave(he needed to blow his load immediately, the night had been torture by way of too much pleasure) by Stella making an announcement.

“Attention everyone,” she yelled over the music. “It’s officially after midnight and so we have to say goodbye to our six little locked friends for the night, though I’m sure we’ll see them all again soon. It’s time to officially welcome our new pledges into Pi Delta.”

Hannah wrapped him in a tight embrace as he made his way towards the exit, thanking him over and over again for helping her get into the sorority.

He collected his phone from the same busty brunette he had handed it to when he showed up. He noticed that the screen didn’t light up when he picked his phone up.

“We turned all the phones off after verifying that the task had been complete. We didn’t want to be stuck listening to any notification noises all night,” she said in response to his questioning look.

Fair enough, he guessed. Though he didn’t know any college student who didn’t keep their phone silenced. Holding the button to power it back on, he tossed it in his pocket and all but sprinted back to his dorm.

Once he was drunkenly able to fit his key into the lock, he threw the door open, kicked off his shoes and rushed to his bed. He grabbed his tissue box and lotion on his way. He kept them separated from each other to try to mask what their true use was.

He pulled out his phone as he shed his clothes and lounged on his made bed, ready to pull off his cage and take care of himself. This time his phone lit up when he held it up to his face and he was met with two notifications from the Cyberlok app. His heartrate spiked as anxiety rushed through his body.

SneakyStella added as a keyholder

SneakyStella added 30 days to BestieNoah’s sentence

Remaining time: 29 days 23 hours 35 minutes 27 seconds


r/ChastityStories • • 4d ago

M Chaste,F Keyholder Reviving the Dead Bedroom - Part 4 NSFW

65 Upvotes

That night was the most sleepless of my life. Not just because my backside burned every time I rolled on my back or my balls would ache the second I rolled on my front or the fact my cock had been straining in its cage since I saw the new latex clothed version of the love of my life but because my mind wouldn’t rest for a second wonder if she was capable of tonight, what else was she capable of?! My mind was spinning in circles. My cock was throbbing at the possibilities and every time my cock flinched out of honey desire, I would be brought right back to be tied to the bench and my nuts being used as my wife’s favourite punching bag. 

Over the weekend we went about our lives. The family all came home and when anyone mentioned me walking funny, my wife would make a joke about me being old or having fallen down the stairs in the middle of the night. Monday and Tuesday at work were challenging. The office HR manager asked me if I needed to go home or see the company nurse. I brushed it all off blaming my old athletic injuries from my youth flaring up. However, because of my current state, I hadn’t started the workout routine I had promised my wife and myself when we started this journey. 

As I left for work on Wednesday my wife passed a brand new gym bag to me. “You have a training session with Liz at 5:30. You have everything you need in the bag. New workout clothes and shoes. Don’t be late and make sure to work hard. I’ll be asking for progression reports so you better not disappoint…” saying as she stepped up to me and whispered in my ear “Or there will be consequences Mr.” I obviously didn’t doubt that for a second after Friday night. 

My day went by smoothly and I got to the gym with just enough time to change. When I got to the desk a short pixie of a young woman was there. She looked at me with a knowing glare “You my 5:30?” I responded with “you must be Liz.” She was stunning. Fit in all the right places and good sized and well toned ass. She came out from behind the desk and she was in a sports bra and very tight spandex shorts. I was definitely in trouble as I felt my cock twitch and start to fill my cage. She started to walk out to the gym floor and I was gawking at her perfectly round ass when she turned back around and caught me staring and scoffed “Let’s go Subby. From what your wife told me about you, you couldn’t even do anything to me if you could get me.” My face burned instantly with embarrassment. I couldn’t believe my wife would have said something but at the same time, I had to wonder if she would have called me out if she hadn’t caught me perving on her. 

We got to some open space where she explained we would start with a bit of a stretching routine she likes me to do before starting any workout, here at the gym or at home. As we were in a more public area she leaned in, similar to how my wife had earlier that morning and said “Do to the current condition your wife left your ass in, we will skip the floor portion. But next week we will get you there!” Ahhh again! My face was burning red. I couldn’t believe my wife had shared so much about me. About us?!  But before I could let the blood drain from my face she gave my ass a playful tap and told me to follow. “I guess your wife really did a number on you!” She said with a chuckle as I noticeably whimpered upon her hand making contact with my sensitive backside. 

The rest of the training session was uneventful. I tried to work as hard as I could in the hope I didn’t inflict any more punishment from my wife. Liz told me to hit the shower which instantly made my dick swell in its cage while I had a quick fantasy image of Liz shower flash before my eyes. I thanked her for the session and told her I looked forward to our next session. She smiled back and said “well same time, same channel next week. And hopefully your wife won’t crack your ass so hard so we can really get into it. Until then, Subby!” Again, my wife went crimson red and I died a little inside knowing she knew so much about my intimate life, although my cock was bulging out of the bars of my cage. 

Wednesday night after the gym was uneventful. Thursday I finally got up early to get a small workout in. Friday morning a little bit more intensive workout. It was still so new that I couldn’t tell if my body hurt from my new workouts or still from my wife laying a beating on my back side. 

Around lunchtime on Friday, I was in my office when my phone lit up with a text message from my wife. It read:

‘Hey Subby,

The kids are going over to their friends for the night. I’m heading to dinner with some girlfriends after work. I’ll be home by 9pm. You will NOT drink and you will make sure the house is spotless. After my inspection, I will inform you about what the rest of the night has in store. Do not disappoint. 

Love you,

Your beautiful Keyholding Wife’

My heart skipped a beat. Here we were after spending months/years living together without any passion or real intimacy. Now, one text message from her had my locked dick leaking like a broken faucet. 

After work I sped home. I didn’t know what she wanted but I knew the usual complaints she had when it came to my cleaning so I figured I would focus on those areas while doing my weekly chores. By 8pm I had flipped the laundry twice and folded and put everything away. I had cleaned the kitchen floor to ceiling including vacuuming and then mopping the entire kitchen floor. I had also tackled all three of our bathrooms, master, kids and powder room. I made sure there was not a single thing left unwiped and spotless. Just as I was going to sit down my phone buzzed with a message from my wife.

‘Subby,

Hope you’ve finished your chores. Change of plans. I’ll be home by 8:30. I need you to get out a chair from our old dining room set that should be in the storage room in the basement. I want you to place the chair in the middle of the room where I had the bench set up last week. Then I need you to strip naked and fold your clothes and leave them in a pile on the stairs. When I get home I will inspect the house then meet you downstairs. Do not disappoint me. 

Love,

Your Keyholding Gorgeous Wife’

I took one final wrap around the house to make sure everything was right and then ran downstairs to get the chair out of the storage closet. After stripping down to my cage, I folded my clothes and knelt beside the chair to wait for my wife. At exactly 8:30 I heard her come in the front down and wander around clearly completing her inspection. Finally I heard her coming down the stairs and I tried to sit up straight on my knees to show my best posture. 

“Nicely done sweetheart. Everything looks great!” I smiled and assumed the basement had become our sexy fun time place and I was about to be rewarded. She was carrying a bag from presumably the same novelty adult store where she had procured the paddle and humbler the week before. She walked behind me without showing me what was in the bag and quickly blindfolded me so I was again blind to see what was coming. “Stand my lovely subby!” She commanded and I quickly jumped to my feet to have her help shuffle me over to the chair. Suddenly I felt her secure my ankles to the legs of the chair and then cuffed my hands behind my back. She told me to shift back and to bend my knees so my thighs were at a 45 degree angle. She then took my hands and tied the cuffs to the chair and began to pull down forcing me into a half squat position. She told me to hold it and then I heard an odd sound of a suction cup securing to something. 

“Ok subby here is how tonight is going to go. My girlfriends are all on their way here for a night cap. I told them to be here for 9 so I had a chance to tidy. I told them you were out of town for work. I was going to come home at 9 and play with your locked cock to say sorry for spanking you so hard. But then I heard from Ms.Liz about you gawking at her ass, I felt like a night of correction was in order. I didn’t think spanking you again would be a fair punishment so I came up with a new idea while I was out shopping after work.” I was still unsure how bad this was going to be but ultimately relieved that I wouldn’t be spanked again. And honestly all I did was get lost with the sight of a spectacular ass. 

“So here’s the punishment, you will stay in the position until the ladies and I are done with our nightcap. If at any point you make any noise and the ladies ask ‘What was that?’ I will bring them down here to show them. If you stay completely silent, then after I’m done I will come release you.” This was going to suck but she gave me a chair so if I failed at least I was only sitting down a few inches, so I wouldn’t make much noise. Surely not enough to have the ladies upstairs hear me. She started to walk around the back of the chair when she pulled down aggressively on the rope that tied my arms to the back of the chair and finally I understood her evil plan. I opened my mouth and was silent. 

“Get it now Subby?!? That’s a very large butt plug your asshole is now resting on. If (/when) your legs give out you will be sitting down on a XXXL cone plug that I can tell will stretch you to a new level. And because it’s suctioned to the chair, once you’re down on it, I don’t think you have the ab strength to get back up. Especially if you go all the way down on it and your tight little hole closes around the base. That big boy is in there until I untie you. So I hope you’re ready fella for a challenging evening because you either have to stay quiet while fighting to stay off of it or you will have to stay quiet as it enters into you. Either way, I hope you will have learned your lesson about gawking at a young ladies behind.”

She laughed as the doorbell rang. “There’s my friends. So better be quiet, love or we’re all going to get to watch the show!” My legs were already starting to ache so I knew it was going to be a matter of time before I was going to be impaled by the giant plug below me. I heard a number of footsteps above me and walked to the kitchen. As they walked by the door I heard a number of them clear as day; my wife hadn’t closed the door to the basement stairs. I hoped she would move into the family room to help give me some space and a wall or two to muff any noise but they were setting up in the kitchen. I even heard one of the ladies say “oh the door to the basement is open, want me to shut that” before my wife quickly answered “oh no, the cat's litter is down there, we always keep it open.”

I listened to them talk about everything you assume ladies drinking talk about. Husbands, boyfriends, work, kids, husbands, boyfriends, politics, husbands, boyfriends , so on and so forth. After 20 minutes my legs finally gave. I had no choice but to rest my weight back on the plug. As soon as I felt an inch enter me I realized my devilish wife had applied a significant amount of lube on the tip and it allowed an inch to directly enter my back door. As I sat down I realized she had been kidding about the size as it ballooned out quickly. I tried doing mini squats to try and get used to the impalement while giving my legs a break but all it did was expedite the fatigue my legs were feeling. Finally my knees gave out and I sat back with full weight and had two then quickly three inches of the plug stretching my hole to a new level. At the three inch mark it must have been at least 2”-3” in circumference and continued to grow. 

I tried to stand back up but my wife had called it. Without being able to use my hands and push myself up I was slowly becoming a victim of gravity. My asshole continued to stretch but now without being able to bounce I was just gradually sliding down on it and beginning to feel the uncomfortable burn of a stretched sphincter. The ladies were getting louder and presumably drunker as I continued to slide deeper onto the plug. As I felt like it was going to split me in half, I finally fell the last 2 inches and my asshole closed around the base as my asscheeks hit the chair. As much as I was feeling incredibly full and very uncomfortable, my cock began to leak and drip from its cage. I tried fruitlessly to stand up and instantly was unable but as I leaned forward the plug hit my prostate and a wave of euphoria rocked through my body. After so much pain and inability to cum, suddenly my body felt like it could erupt. 

I rocked back and forth a few times feeling the full weight and size of the plug in my ass pressing on my prostate. Suddenly I was lost in the moment. My body was now accustomed to the invader in my asshole. As I shimmied back and forth on the chair, I could feel my caged cock leak more. Finally the ladies began to pack up and leave and one by one filed out. I heard the door close and I figured my wife would come down and retrieve me but she didn’t. After feeling pleasure like this for the first time and feeling like I had an opportunity I began to really rock back and forth. After only a few seconds my cock began to shoot through my cage a hot thick load of cum on the floor in front of me. Still blinded and unable to see I continued to rock and suddenly I became acutely aware of how loud I was moaning out in pleasure. I stopped suddenly when I heard my wife at the top of the stairs say “I don’t know what that was Liz. Would you mind coming down to investigate?” 

To be continued….


r/ChastityStories • • 4d ago

M Chaste,F Keyholder Marie & Thomas - Chapt. 1 NSFW

48 Upvotes

Chapter 1 – The Contract

Thomas was heading to the shop, restless. His cage was ready after several days of meticulous craftsmanship. He knew this evening would mark a definitive turning point in his life. He had thought about it at length. Marie’s warnings and tests had been perfectly clear: there would be no going back, and she would show no mercy. She was going to push his limits hard. But she was also finally going to let him live out the fantasies he had carried inside him for so long.

Thomas had been successful in life. The company he had founded was now thriving almost without him, thanks to a solid team. He went to the office less and less, which allowed him to travel often. His absence was barely noticed anymore. He had no children. He had invested most of his time and energy into his work. Recently, he had built a large modern house in the countryside, isolated from any neighbors, deep in the forest. A quiet, luxurious place designed for silence. He was used to bringing conquests there, but those stories always remained fleeting.

In all his previous relationships, Thomas had already explored BDSM play. Never, however, with the intensity he truly desired. He had slept with Marie a few times. Her self-assurance, her natural confidence attracted him deeply. Yet he had never dared reveal his darkest secrets to her… until the evening she invited him to her place. That night, she had clearly seen the submissive side in him that she had been looking for ever since she learned about her friend Sophie, who had locked her own husband in a cage. Marie had then started testing Thomas, discreetly at first, then more and more directly. Very quickly, she had realized he was the ideal candidate to become her submissive.

Since then, Marie had spent most of her time crafting her plan. She wanted to train Thomas methodically in order to satisfy this new, urgent need for domination that had taken hold of her. She couldn’t wait to discover how far she could take him. Her plan began tonight.

Thomas opened the door of the shop. The interior was very quiet, filled with the smell of leather. He walked in and headed nervously toward the counter. The owner approached him calmly, her heels clicking on the floor. She looked at Thomas with an amused expression, studying him, knowing full well what he was getting into.

“Hello Thomas,” she said. “I’ve been expecting you.”

She continued in a calm, professional voice:

“I’m going to give you a few basic reminders, just as a precaution. The cage that was made for you is designed first and foremost to make it impossible to access your cock while it’s locked. It remains comfortable even for long-term wear, including very long-term. There is no physical key that can open it—only the app that your Mistress has full control over. Once the setup is complete, only she can release you. No one else. The cage is equipped with small electrodes that allow your Mistress to send shocks of varying intensity. Are you comfortable with all of that, Thomas?”

He already knew all of this, but hearing the woman state these details gave him a deliciously humiliating sensation. Thomas thanked her for the warning and confirmed that he accepted everything.

“Perfect. I’ll give you your cage then, and you can go put it on in the fitting room to make sure it’s comfortable.”

Thomas walked to the back of the shop with the small box. He tried to distract himself along the way, because the scene and all the objects displayed around him were already giving him an erection that would make putting the cage on more difficult. He stepped into the fitting room and awkwardly removed his pants. Once naked, he opened the box and discovered the magnificent metal cage. It was gleaming, solid without being too heavy, a little shorter than he had imagined. It was a true work of art. He first slipped on the ring, which fit perfectly, then the cage, which compressed his cock slightly. As soon as the cage met the ring, he felt a solid, definitive click: it had locked automatically on contact.

That was it. His cock was imprisoned. There was no longer any doubt about the seriousness and security of the cage. Completely aroused by the situation, Thomas tried to get hard… and immediately understood that there was absolutely no room for that. He put his pants back on and returned to the woman, heart pounding, already transformed.

Thomas came back to the counter, his face still a little flushed, the cage already securely in place under his pants. The owner greeted him with a slightly more pointed smile than usual, looking at him a few seconds too long. He lowered his eyes slightly.

“So… are you happy with your new cage? Is it comfortable?”

Thomas nodded briefly, his gaze still a little downcast.

“Yes… it is. Thank you very much.”

She seemed satisfied with the answer. Then she handed him several heavy black bags, carefully sealed.

“Here are the items Marie ordered. You’re not allowed to look inside. You pay the bill, and you hand them to her in person. Nothing else.”

Thomas took the bags without protest. The bill was steep—much higher than he had imagined. He paid without a word, heart racing, then left the shop with his new invisible chains.

He drove to Marie’s apartment. She was already waiting on the doorstep, a large suitcase at her feet. She greeted him with a simple look followed by a wide smile, then opened the trunk of her car and put the suitcase in herself before getting into the driver’s seat.

“Hi Thomas… There are some nice bags in the trunk.

I’m going to live at your place for the next few weeks,” she said in a calm, composed voice.

“Starting tonight, your house becomes my territory.”

“Perfect, Marie… We’ll be very comfortable. At least you will, for sure.”

Once they arrived at the large isolated house deep in the forest, Marie immediately showed who was in charge. While Thomas prepared dinner, she went upstairs to the master bedroom and settled her things. Her clothes filled the closets. Her toiletries took over the bathroom. When she came back downstairs, the table was set.

“Show me your cage.”

Thomas lowered his pants.

Marie approached slowly, her eyes already fixed on the cage. She knelt in front of him, took the cold, shiny metal between her fingers and turned it under the light to admire it better.

“Oh… look at that. A beautiful quality cage. Heavy, perfectly fitted, impeccable. You must already feel how well it holds you…”

She tilted her head, pressed her lips against the polished metal and licked it slowly, thoroughly, as if savoring both the taste and the humiliation. Her tongue slid along the bars, then over the base where Thomas’s flesh was swelling uselessly against the metal.

She stood up, took out her phone and opened the app. A first light shock ran through his locked cock. Thomas jumped.

A second, stronger one made him grimace.

Then a third, precise and cruel, while she stared straight into his eyes, made him contract violently inside the cage.

Marie smiled, her eyes shining with satisfaction. “Perfect. Everything works.”

During the meal, she placed a document in front of him.

“Here’s the contract.”

Thomas read it while Marie calmly observed his reactions, eating quietly.

The document clearly stated: it lasts a full month and Thomas will have no way out before the end of the term. By signing it, he renounces all his rights, simply becomes Marie’s slave, obeys without discussion, accepts being punished and humiliated without reason, more often restrained than free, and possibly remains permanently locked in his cage. Marie will live in his house, control him completely, and may, if she wishes, invite other men to fuck her in front of him if her desire for a real cock becomes too strong.

While he was reading, she took out of the bag and placed on the table a thick metal collar fitted with an integrated lock connected to the same app. A metal ring was attached to it.

Thomas finished reading, then said:

“I’ve been in charge of people my whole life. The first time you gave me orders, you woke up the deepest desires in me. I’ve never felt like this before. I want to go as far as possible, and I trust you to take me there.”

He signed the document and pushed it toward Marie.

More than satisfied, Marie stood up without a word. She placed the collar around his neck and locked it with a sharp click.

“On your knees. Under the table.”

Thomas obeyed. Marie sat down, spread her thighs and lifted her skirt. She wasn’t wearing any panties. Her pussy was already completely wet. She firmly grabbed Thomas’s hair and pulled his face against her.

“Put your hands behind your back, stick out your tongue, and lick your Mistress while I finish my plate.”

He obeyed. His tongue slid over the warm, slick folds. Marie, for her part, continued eating calmly, barely paying attention, as if the service he was providing was simply normal.

A few minutes passed like that. Then, little by little, her breathing changed. She let out a first discreet moan, put down her fork and began to slowly roll her hips, grinding more firmly against Thomas’s mouth.

Marie, one hand now resting casually on the back of Thomas’s head and the other holding her glass of wine, said in a calm voice:

“Your house is really magnificent… our house now. But I have to admit I was disappointed when I went down to the basement. A rich little submissive like you—I expected a real dungeon that would have made my life easier. I had to buy a few items at the shop… and sorry if it was a bit expensive.”

“I’ve done some research, and I know someone who’s very good at setting up ‘playrooms.’ We’re going to have to do some work to make the whole space useful.”

It had already been about fifteen minutes that Marie was being licked by Thomas, on his knees, focused to the maximum to give her as much pleasure as possible, while she explained part of her plans for the coming days. He could tell she was on her phone. Suddenly, an electric shock jolted his cock, which was turning red from straining against the cage.

“Thomas, you’re going to have to improve with your tongue. I should already have had at least one orgasm.”

“Sorry, Marie…”

A new, stronger shock rang out.

“I’m no longer Marie to you. I am your Mistress. You never call me Marie again, understood, my little sub?”

“Yes, Mistress.”

She stood up, gave him one last cold, satisfied look, then walked away while dialing a phone number and pouring herself more wine. Thomas remained on his knees, hands still crossed behind his back, chin resting on the seat of the chair she had just left. Under the table, the heavy collar around his neck, the tight cage, the taste of his Mistress still on his tongue.

“Hello, we spoke this week about the plans for a basement. Are you still available to come by tomorrow evening? … Perfect. Looking forward to meeting you.”

Marie came back and sat down. She lifted her skirt again just before settling in. Thomas was still perfectly positioned. Without a word from either of them, he picked up exactly where he had left off.

After a few more minutes of diligent licking, he finally managed to give her a first orgasm. Marie closed her eyes, caressed her breasts and sprawled completely on her chair, pressing down heavily on Thomas’s face. She was thinking about her plan, which so far was unfolding exactly as expected.

“Thank you, that was already much better. 1-0 for me in the orgasm chapter. I can’t wait to see how this score evolves… it might not end up very evenly distributed.”

She stood up, briefly adjusted her skirt and ordered:

“Follow me to my bedroom.”

Once upstairs, Thomas saw a thin mattress on the floor next to the large bed, as well as a heavy chain fixed to the base of the frame. He didn’t dare ask any questions, but quickly understood that he would very likely be sleeping there.

On the bed, a large dildo was already mounted on a harness. Marie pointed to it.

“Since your cock is useless now, you’re going to fuck me with this. Much bigger than anything you’ve ever had between your legs.”

Thomas complied without a word. He put on the harness and simulated the movements he had made only a few weeks earlier, but this time without any sensation. For Marie, on the other hand, it was even better: total control, pure domination, and the pleasure of being fucked by an object she had chosen, mounted on a body that no longer had any rights.

After several positions that she imposed one after another, she finally had enough for the evening. She pushed him onto his back and firmly squatted on his face. His mouth was immediately filled with the heat and scent of her still-soaked pussy. Thomas struggled to move his tongue under the weight of his Mistress. Marie squeezed his balls hard in her hand and explained in a calm, authoritative voice:

“This is how we’re going to fuck from now on. Understood?”

“Yes, Mistress.”

“Now go take a shower and come back. You have five minutes. Not one more.”

He hurried. When he returned, Marie was already waiting near the mattress.

“Your new bed is there, on the floor. If you’re a good submissive, you might sometimes be allowed to sleep next to me… but for the first few days, I’m going to have to train you properly. We’ll see after that.”

She took the chain, passed it through the ring of his collar and locked it with a sharp click. He had a little play, just enough to lie down, but not enough to move away, and absolutely no way for Thomas to escape.

“Good night. Sleep well… your training continues tomorrow.”


r/ChastityStories • • 4d ago

M Chaste,M Keyholder Car Collateral - Turn 5 NSFW

28 Upvotes

For all my other stories and other parts of this one:

https://www.reddit.com/user/Chastity_Wannabe/comments/1k9n4xt/story_index_file/

Thanks for all the love, everyone!

I created a Patreon and it already has a few exclusive stories that will only be here in a month: Maybe give it a look??? It would help to be able to keep writing stories!

******************************************************************

When Saturday morning came, Dean REALLY wanted to sleep a little longer, but since Colin had work, he stood up with his friend and rushed to prepare breakfast. After they both ate, Dean drove his friend to work, promising he'd be there to pick him up at 1 pm, and Colin promised to return home with lunch for both of them!

As the Dean returned home, he jumped in bed and turned the TV on, putting some videos on gardening so he might learn something through osmosis. As he adjusted in bed for some comfort, his hand instinctively going inside his shorts and boxers and finding his trapped balls to play for a little while. He was about 10 minutes in when his phone ringed with a WhatsApp message:

Robbie: Guess what i found?
Dean: Hey Robbie, good morning!
Dean: How are you?
Robbie: Good good, fine
Robbie: WBU?
Robbie: Take a guess!
Dean: Also good
Dean: And idk
Dean: Your will to live?
Robbie: Smartass!
Robbie: No! ;-)
Robbie: Found your OF!
Dean: Ohh, man, no!
Dean: I shouldn’t have told you about it!
Dean: Please, don’t look it!
Robbie: Too late! I already purchased everything you posted EVER!
Dean: Come on, man! Don't look at my noodle!
Robbie: Helped A LOT with my self-esteem! 
Dean: I HATE you!
Robbie: Who's hand was that?
Robbie: It's a man's hand, i mean
Robbie: The guy jerking you off and shaving you!
Dean: I don't feel comfortable talking about it!
Robbie: Okay, but… Does that mean's you're bi?
Robbie: I'd love to talk to someone that is!
Dean: I REALLY don't know what i am! 
Dean: But i enjoyed… What we did!
Robbie: Me too!
Robbie: Listen, can we see each other some place without my family?
Robbie: Or your work?
Dean: You make jokes about my dick and now you want to see me?
Robbie: I don't care much about your dick size…
Robbie: Hope it's not offensive
Dean: I have my afternoon free tomorrow, what do you want?
Robbie: Wanna go with me in the boat? Cruise the lake?
Dean: I'd feel safer in a public place, honestly
Dean: And please, don't think i'll show up to be fucked!
Robbie: Now who's judging who?
Dean: Yeah, that wasn't nice
Dean: I'm sorry
Dean: I just feel really vulnerable around you
Dean: Most of my problems can be fixed by 
Dean: You know!
Robbie: Tomorrow, 2pm, park
Robbie: I'll text you the deets
Robbie: Now i'm gonna jerk off to your tiny dick
Dean: Happy i'm helping with your bisexual crisis!

Dean wished he could ask the other boy for some pictures or videos, but he didn't want to force the rich boy to tell him no! He was curious enough to open his OF and check. It was easy to find out Robbie's user, and soon enough he learned the boy actually bought every single picture and video he sold for the past 2 years and now Dean had made an extra 80 dollars.

For the rest of the morning, Dean was watching TV and contemplating the fact that Robbie already knew about his second biggest insecurity in the world. When it was finally time for him to go pick Colin up, he was thankful to have something else to fill his mind. Even so, he didn't feel like telling Colin about meeting with Robbie on the next day… It was a conversation that would bring too many questions he didn't even knew the answer himself.

And so, after lunch, it was time for both of the boys to go out and do something for the first time: Mown some lawn for the first time in their lives. It was for an old lady and they were only making 20 dollars total for that, but it was good for them to learn, plus, it was a church lady, so they could get some good word from the old lady! Plus, it was just about 10 minutes of driving, so it was cheap on the gas… They'd be able to have dinner on those 20 dollars and that was it! It took the boys longer than expected to finish their work, but as they were done, their job was GREAT, and they were proud of it. More than that, For those few hours, Dean didn't think about his caged dick ONCE!

Back at home, once again, Colin put on some sexy reality show, and, from the top bunk, Dean could listen to his friend jerking off on the botton bunk. The hand trying to grab his feet only made Dean laugh, but there was no much explanation about why he was trying to get hard inside his tiny cage! And so, listening to his friend jerk off, Dean put his hands inside his underwear and started squeezing his trapped balls!

Sunday morning meant the boys took care of the trailer chores and went out to do laundry and buy some stuff at costco. They once again had hot dogs and pizza for lunch and, after Dean left his friend to work, and with some spare time, he went to Planet Fitness, the only thing "extra" he was paying for himself every month! It was a learning curve to find out what he could do and what was hurtful to his body now that a cage with a metal strap surrounded his waist. Running on the treadmill and using the stationary bicycle was out of question, as most of cardio was, Plus, there were some leg exercises that just made his balls hurt!

Eventually, time was running out, and Dean decided on showering at the gym. And then Dean learned something about himself… There was a risk, only a curtain separated anyone from seeing his locked dick, and the boy was getting horny from it, the risk of being exposed EXCITED him! Even so, no surprises, soon, the cold water calmed him down, the boy got dressed in his best clothes and off he went to meet Robbie. It took him about half an hour to get to the park where they agreed to meet , but they arrived almost together, so that was just great.

— Hey, man! — Dean said, looking at the boy's Range Rover SV. — That's such a nice car!
— Ohh, thanks! — Robbie said, giving zero attention to his car, only looking at Dean. — You look great!
— Thanks, man! — Dean said, blushing. Looking at Robbie, he could see the boy looked like money. For sure Robbie “produced himself” for him. — You look great too!
— Thank you! — Robbie said, also blushing. — Hey… How about we go grab some coffee and find some place to sit?
— That sounds great! — Dean agreed.

As the boys walked side by side, Dean could feel a little spark as his arm brushed Robbie's arm, and, for some reason he had no idea why, he felt his little noodle trying its best to surge to life in that metalic tube! It was failing horribly, and for once, Dean was happy for it. Even a small erection would be visible and make him want to die!

Dean and Robbie got their coffees together, and Dean was kinda happy the other boy jumped in to pay. Yeah, he had the 8 dollars, but that was almost everything he made from his lawn mowing job from the day before and he was hurting from it. As he sipped his Flat White, they found a picnic table in an empty area under some trees and just sat down facing each other.

— Hey, thanks for coming to me! — Dean said, smiling. — I hope it wasn't a problem with your family!
— Ohh, i'm free to just be myself around! — Robbie said, smiling. — Well, i mean, i hope so!
— You're afraid of how they'd react to you coming out? — Dean said.
— I'm NOT ready for this kind of conversation, man! — Robbie replied. — But huh… I need to tell you i'm sorry about Julie! I swear i'll never hit on her again, i didn't knew you liked her!
— She's not my girl, you're allowed to do anything you want! — Dean replied. — You don't owe me anything, seriously.
— Yeah, but like… I don't want to make you sad for someone who doesn't mean anything to me! — Robbie said.
— Thank you… And like… Just thank you! — Dean said, glitching out. — But don't stop being happy because of me!
— You made me feel more than she did, honestly! — Robbie said, feeling embarrassed.
— Was i really your first dude? — Dean asked, confused about everything.
— Yeah… — Robbie admitted. — Honestly, i don't even know where the courage came from, how i was brave enough to ask you for it! But i was already there in that situation with my dick out and… It sounded perfect! Was i your first guy?
— I can't say so… — Dean replied, blushing.
— And you say you're straight. — Robbie teased him, but it sounded like he was a bit jealous.
— Dude, when you're as broke as i am, there's no space in life to be straight… — Dean replied, shrugging. — I took your 150 for doing what you liked, i once jerked a guy off for a tank of gas… And there were many times when I sold jerking-off videos on OF to pay for my shared trailer rent or feet pics for lunch money!
— When you say it like that i feel like i took advantage of your situation! — Robbie said, actually feeling guilty.
— Don't worry, man! You took advantage of me, and i took advantage of you! — Dean said, shrugging.
— Yeah, but i felt something! — Robbie admitted.
— Do you thing i'm going to park meetings with the guy i jerked off for gas? — Dean asked with a smile.
— That makes me really happy! — Robbie replied. — Man… I wanna learn more about you!
— What do you wanna learn? — Dean asked.
— I don't know… You know my deepest secret and i barelly know you! — Robbie replied.
— You've seen my deepest secret! — Dean replied, blushing once more!
— You're embarrassed by your size? — Robbie asked, actually taking interest in the subject.
— Man… I'm still a virgin because of it! — Dean said, and then he got SO upset he just turned around, unable to face Robbie. — Please, ignore what i just said!
— Dean, it's all good! — Robbie said, passing an arm over Dean's shoulders.

Dean went straight for a hug, embracing the other boy who thankfully returned the favor from a few days before. Thankfully, Robbie didn't push on the subject of Dean's manhood size, so the conversation wasn't awkward. For about one hour, both boys sat down, drank their coffees and Dean told the other boy all about his life, about the trailer, about Colin and his job… All he held back was his size predicament and about the whole car ordeal.

After that, Robbie finally felt good enough to open up about how he felt about his sexuality, how he always liked girls, and even telling Dean all about his first time with one, but how he also had to watch gay porn while he jerked off because a muscular guy taking a pounding did more for him than any pair of boobies shuffling around. By the time Robbie stopped with his story, both boys were feeling horny and, every single time their knees would touch under the table, they’d both feel a spark… Eventually, it was time for them to go.

— Hey, listen… I’m always in desperate need of money, so if you have any friends who need their grass cut or… — Dean broke mid-sentence. — You know…
— Ohh, i’m not offering your intimate services or OF to anyone! — Robbie said, but it wasn’t a joke, he just didn’t want to share Dean with anyone. — But… I do have some money on me and my car windows are completely black!
— Ohh… I wasn’t expecting it to be THIS fast! — Dean said, confused. — Listen, i’m game to repeat what we did, but… Not anything new, okay?
— Ohh, deal! — Robbie replied, looking like a boy that just saw santa!

As the boys walked to Robbie’s over 200K car, Dean inspected the vehicle to make sure it really was impossible to see the inside from the outside. When he was sure, the boy waited for Robbie to open the door and they both got into the front seat. The central console was HUGE, but it was flat and padded, so it would be actually comfortable.

— Okay, take your pants down! — Dean said, even if feeling uncomfortable. He heard the doors locking.
— Ohh, okay! — Robbie replied, panicking. — That’s so awkward… Can we do things in reverse this time?
— You wanna start by kissing? — Dean asked and Robbie was so nervous he could only reply by nodding.

So… Dean just leaned forward, he was using his left arm for support, but his other hand went behind Robbie’s neck and pulled the boy in. Soon, their lips touched and after that, it was an easy sequence for them to be fully making out. As Dean’s dick started taking the whole space of the cage, the boy started really enjoying the whole tongue-up-his-mouth thing…

Dean could feel how horny he was, but most impressively, he could feel how the OTHER boy was horny. That’s why, while Robbie was lost playing inside his mouth, Dean took his right hand from Robbie’s head and moved down to the boy’s suit pants. Even over those pants, Dean could feel the boy’s giant erection.

After grabbing that massive twitching dick over those pants a few times, Dean opened the boy’s leather belt and just a second later, he found the button of those pants, opening it single-handedly. Dean could just force the zipper open, but he decided it would be more sexy just to slowly pull it down. 

After that, Robbie forced his butt up a little, and Dean just forced the boy’s pants down. Dean looked down without moving his mouth, but he could see the boy was wearing black Calvin Klein boxer briefs, and that cotton just couldn’t hold such a massive erection. That dick was just stretching the underwear, pointing up, twitching inside that underwear and leaking a bit!

And then, Dean couldn’t hold it any longer, he just pulled the the elastic band down and watched Robbie’s dick flop up and slap the boy’s shirt. When Dean grabbed that thick dick, it was warm, a bit wet and throbbing. Dean pressed it inside his hand and, with his first thrust, not only did he made Robbie moan a little, but the boy also gave his lips a little bite!

Never breaking that kiss, Dean sped up on the boy’s dick, firmly jerking the boy off, using his own constant ooze of pre-cum to lube the boy’s shaft. Dean was jerking that dick for about 2 minutes when he noticed Robbie getting his balls out of his underwear and start to play with them. A movement from Robbie’s other hand going towards Dean’s crotch got the boy alarmed and he used his support arm to block the boy. Robbie wanted to protest, but the fear of Dean stoping the whole thing made him pause!

Still alarmed, still feeling defensive, Dean kept on kissing the other boy, kept on jerking that massive shaft he DESPERATELY wanted to be looking at. In the end, the will to keep on kissing while his dick cried inside that metalic tube was greater. Soon, Robbie’s breath started getting erratic and dean knew the boy was getting closer to an orgasm. Then, Robbie moaned inside his mouth and Dean was quick on moving his left hand to cover the boy’s tip, collecting all the boy’s cum on his palm.

— Ohh my God, that was SO GREAT! — Robbie finally said after the tenth rope of cum rushed out of his tip and landed on Dean’s palm, filling it up! — Thank you so much!
— Where can i clean my hand? — Dean asked, nervous.
— Ohh, fuck! — Robbie replied, looking everywhere desperate. — Fuck… Man, just use my underwear! I don’t mind riding in my filth for a while!
— Okay! — Dean said but then decided on using the INSIDE of the boy’s underwear just to be a little cleaner. — I hope it was at least as good as the last time!
— Ohh, it was better since you done it from start to end! — Robbie replied. — Thank you, seriously!
— It was my pleasure! — Dean said, then decided to add. — Now pay me!
— Okay, business boy! — Robbie said, giving Dean another $150.00. — I’ll give you another $50.00 if you let me see your dick!
— Ohh man, today i’m not THAT desperate! — Dean replied.
— You really feel THAT bad about your dick? — Robbie asked.
— Yeah… I’m sorry! — Dean replied. — I just can’t! Maybe one day i’ll be desperate enough!
— I hope not, but i hope i can convince you one of this days! — Robbie replied. — So… That’s all that’s ever going to happen?
— I have no idea, man! — Dean replied. — I’m pretty new to this! Like, it’s not a denial, but i can’t promise you anymore!
— I’m sorry if i made you feel uncomfortable! — Robbie said, feeling guilty.
— No, it’s all good, man! — Dean replied, giving the boy a smile. — I met you today knowing this was a possibility and entered your car knowing what was going to happen! Hey, how about you drive me around the block and drive me to my car, i don’t want to look too suspicious!
— Bet you just want to ride in my car! — Robbie replied, teasing Dean and putting his soft dick away inside his wet underwear and closing his pants.
— Ride a dick, faggot! — Dean replied, making Robbie laugh.
— I like you, Dean! — Robbie said, smiling at him.
— I like you too, Robbie! — Dean said, laughing and shaking his head.

And so, Robbie turned the car on and drove off. Dean kept staring at the other boy, smiling at him, learning his facial expressions, and noticing how Robbie was nervous, still going through learning about a whole new aspect of his life. Dean showed the boy his way car and, upon arriving there, he went straight for a “free goodbye kiss” that got Robbie horny all over again.

Dean jumped to his car and watched as Robbie drove away, he didn't know that the boy had already opened his pants and was jerking himself off once again, too excited from the kiss. Dean, on the other hand, Had to calm himself down a little and finish the bottle of water on his door before he'd even start the car. He went straight back home after that, and the second he opened the door, he saw Colin sitting there, watching his reality shows, playing with his own feet.

— Just the guy i needed! — Dean said, still horny and desperate.
— What do you need, buddy? — Colin asked, curious. He could see how on the edge his best friend was.
— You said there was a way you'd be able to make me cum! — Dean replied, desperate.


r/ChastityStories • • 5d ago

M Chaste,F Keyholder Book 1: The Therapists Sissy Maid: Becoming Her Locked Sissy Maid: Part 9 NSFW

29 Upvotes

I use the paid versions of Grammarly and Readable to help make my writing more readable.

If you want early access to the next chapters of this novel and all my other stories, find them here: https://www.patreon.com/c/FemaleLedRelationships 

Prefer Amazon, you can find the full novel here: https://www.amazon.com/dp/B0HJZZX52D

The full story will be posted here.

Part 1 & Part 2 & Part 3 & Part 4 & Part 5 & Part 6 & Part 7 & Part 8

--------------------------------------------------------------------------------------------

Alexandra settled into her leather chair with deliberate grace, the glossy black latex of her pants creaking as she crossed one leg over the other. Her fingers toyed with the silver keys dangling from the necklace between her heavy breasts, rolling them slowly between her fingertips while David's eyes remained glued to the motion. 

His cock strained inside the flat steel chastity cage, the metal biting into his swollen flesh as it tried desperately to harden. A fresh bead of precum pushed through the front slot and dripped onto the floor between his feet.

She reached for the pair of black latex gloves on her desk, pulling them on with slow, deliberate movements. Each finger slid into place with a soft snap, the material stretching tight over her hands. David watched every motion, his breathing shallow and rapid.

“If you consent, I need to inspect the chastity cage as part of your treatment," she said, her tone professional and matter-of-fact. "It's best if you remove all your clothes."

David's face burned crimson. "All... all my clothes?"

"Yes," she replied firmly, her eyes never leaving his face. "I need to ensure everything is functioning properly as part of your treatment."

David's voice cracked as he forced the words out, "O-okay... I-I c-consent..."

His hands trembled as he bent down to untie his shoes, pulling them off along with his socks. He stood on shaky legs and began unbuttoning his black shirt with fumbling fingers, each button revealing more of his flushed chest. 

The shirt slipped from his shoulders and landed on the table beside him. His fingers worked at his belt next, the metal buckle clinking as he unfastened it and pushed his trousers down his legs. They pooled around his ankles before he stepped out of them.

His boxers came last. He hooked his thumbs into the waistband, hesitating for a moment before tugging them down so embarrassed and turned on. His locked cock and balls came into view, the flat steel chastity cage gleaming under the office lights. His face was scarlet as he placed the boxers on the table with the rest of his clothes.

"Take a seat," Alexandra instructed.

David lowered himself onto the leather couch, completely naked except for the steel device locked around his genitals. His small cock remained trapped inside the chastity cage, the metal pressing against his swollen flesh. Precum continued to leak steadily from the front slot, running down the cage and dripping onto his thighs. He sat with his knees pressed together, hands clenched in his lap, his entire body trembling with humiliation and desperate arousal.

Alexandra walked forward and approached him, her gloved hands reaching toward the chastity cage.

Alexandra's gloved fingers closed around the steel cage and the swollen balls beneath it. The latex stretched tight over her knuckles as she lifted the trapped package, weighing it in her palm. David's breath hitched. Her thumb traced the underside of his scrotum, rolling each testicle slowly between her fingers while the cage remained locked in place.

"These testicles are reaching maximum capacity already," she observed, her voice clinical yet laced with something darker. "You're leaking steadily. The cage is coated in a constant layer of precum."

Her grip tightened slightly, massaging the sensitive flesh. David's hips twitched involuntarily. The steel ring bit into the base of his cock as his body tried to respond. More clear fluid pushed through the front slot of the cage, coating her latex-covered fingers.

She held him there, one hand cupping his balls while the other traced the edges of the cage. The contrast between them was stark—her mid-thirties, tall and commanding in her black latex outfit, leather corset cinching her waist, long strict ponytail pulled tight, deep red lips curved in a knowing smile. Black boots planted firmly on the floor. Every inch of her radiated control.

David sat naked and trembling on the leather couch, twenty-one years old, short and petite, his face burning crimson. His small cock remained trapped inside the flat steel chastity cage, his balls heavy and tender in her gloved hand. He couldn't stop staring at her—the way her breasts strained against the latex, the keys nestled between them, the casual authority in every movement.

"The subject is ready for further therapy," Alexandra stated, giving his balls one final squeeze before releasing them. "Your body is responding exactly as intended."

She stepped back, removing the gloves. David remained seated, his cock throbbing uselessly inside the cage, his entire body flushed with humiliation and desperate need. The keys on her necklace swayed gently with her breathing.

Alexandra walked over and sat down in her leather chair, crossing her legs with deliberate slowness. The latex stretched across her thighs as she settled into the seat, her posture radiating complete authority. 

David's eyes followed every movement—her deep red lips parting slightly as she breathed, the way her breasts rose and fell within the glossy black material, the leather corset cinching her waist, and most of all, the silver keys nestled between her cleavage on their thin chain.

He sat completely naked on the couch across from her, his small body trembling. The flat steel chastity cage locked around his cock felt heavier than ever, the metal cold against his skin. 

His balls hung swollen and tender beneath the device, and he could feel the constant trickle of precum leaking from the front slot, dripping onto the leather beneath him. The humiliation burned through him—he was exposed, vulnerable, locked, while she remained fully dressed in her dominant attire.

She picked up her clipboard, pen poised above the paper. "How have you found the last week in the chastity cage?"

David's face flushed crimson. His mouth opened but no words came out at first. He stared at her lips, then her legs, then the keys between her breasts, his thoughts spinning wildly. "I... I... it's... it's on my mind every second," he finally managed, his voice cracking. "Every... every single second of the day. I can't... I can't stop thinking about it."

Alexandra nodded, writing something down. "Keep going."

His breathing grew heavier. The cage felt tighter as his body tried desperately to respond. "I'm... I'm used to cumming twice a day," he admitted, the words tumbling out in a rush. "Sometimes... sometimes three times. And now it's... it's zero. Nothing. I can't... I haven't been able to..."

She made another note on her clipboard, her expression calm and professional. "Masturbating won't help you achieve anything," she said matter-of-factly. "The chastity cage is going to help you not only embrace your submissive tendencies but focus on other people's needs as well."

David's cock throbbed uselessly inside the steel prison, another bead of precum pushing through the slot and sliding down his balls. He couldn't look away from her—from the confident way she sat, from the power she held over him, from those keys that represented his complete surrender.

Alexandra watched him with steady eyes, her pen poised above the clipboard. "David, do you consent to continuing this treatment?" she asked, her voice calm and professional.

"Yes," he blurted out immediately, his face burning red. "Anything for you."

Her panties grew instantly wetter between her thighs. The words hit her like a physical rush of arousal. She smiled slowly, deliberately, letting the silence stretch as she watched his reaction.

"Good boy, David," she said softly.

His balls visibly tightened beneath the steel cage. A thick bead of precum pushed through the slot at the front and dripped down onto the leather couch. His cock strained uselessly inside the metal prison, twitching and leaking in response to her praise. The humiliation made his entire body flush deeper.

Alexandra crossed her legs again, feeling the slick warmth between her thighs as she studied him. He looked so small and vulnerable sitting there completely naked, his petite frame trembling, his locked cock dripping steadily. 

The contrast was intoxicating—her body encased in powerful, glossy black latex that hugged every curve, the leather corset cinching her waist, the keys dangling between her breasts. She felt completely in control while he sat exposed and desperate before her.

She made another note on her clipboard, her eyes never leaving his leaking cage. “Now that you have consented to continuing the treatment, it’s time to get started."

Alexandra's lips curved into that knowing smile as she leaned forward, her latex creaking softly. "We're going to do the pictures exercise again with different pictures, David. Please place on the heart rate monitor”.

She reached across with deliberate slowness, her fingers wrapping around the edge of a fresh stack of photographs. Her eyes locked onto his, dark and commanding, never breaking contact as she lifted the stack.

David sat naked on the leather couch, his skin flushed deep crimson from his face down to his chest as his hands shook trying to attach the monitor. The steel chastity cage gleamed between his spread thighs, his cock straining uselessly against the flat cover. Clear precum leaked steadily from the tip, dripping down to form a small puddle on the leather beneath him. 

His hands trembled where they rested on his knees, his breathing shallow and rapid. 

She held the stack up between them, her gaze never wavering from his embarrassed, desperate expression. The first photograph slid free from her fingers and turned toward him.


r/ChastityStories • • 5d ago

M Chaste,F Keyholder Sorority Rush - Part 2 NSFW

175 Upvotes

The walk to the Pi Delta house felt like he was marching himself to the gallows. He cursed himself for not thinking enough about what he was getting himself into. He was truly happy that he had been able to help Hannah out, but he wasn’t sure it was worth what he was about to endure. The dangling carrot that was the promise of being introduced to the other sisters of Pi Delta by Hannah had distracted him from the fact that all the gorgeous girls he was about to meet would know his dick was trapped in a tiny remote-controlled chastity cage.

And his dick had been straining against that cage ever since he met Hannah outside of her dorm building. She came out in a white tennis skirt that ended just past the curve of her pert little bubble butt and a pink Pi Delta cropped t-shirt, her smooth stomach peeking out with every movement. The sight of her made his heart beat faster and blood rush to his groin. He had been forced to turn away from her to hide the grimace on his face as his penis swelled against the tight confines of its prison.

The hug that she wrapped him up in didn’t help his predicament at all.

“Thank you again for doing this for me,” she said as she bounced away from him, starting their short journey to the sorority house. “I promise I’ll make it up to you. Once my new sisters get to know you, I bet you’ll have to fend them off with a baseball bat. They’ll all see what a catch you are.”

If only she could see what she claimed her sorority sisters would. Her words were kind, but all they did was kick him farther into the friendzone. At least her unintentionally cruel words had the added bonus of throwing a bucket of cold water over his arousal. He raced to keep up with her shorter but fast strides as he was finally able to walk comfortably, his dick no longer fighting to grow erect.

“How many people do you think managed to complete their task?” Noah asked, determined to fill the awkward silence that had been growing and act as if nothing was different between them. Even though everything was different, even if it was just for a night. Hannah held complete control over his most prized body part. He was completely at her mercy. Regardless of how much he trusted her, the thought was still enough to set his heart to racing.

“I don’t know,” she said morosely. Clearly the idea of a bunch of her newfound friends failing to join the sorority was a sad topic. “Mai, Taylor and Chloe have boyfriends so they’ll probably be fine. Although Mai didn’t meet hers until she got to campus so the guy might decide to run for the hills instead. And I’d never bet against Sofia in a challenge like this. I think I blush every time she speaks. But including me, that only gets to five out of the eight of us. And I’m not sure if all those I named are locks. I doubt every guy is as cool with this as you’ve been.”

Was he cool with it? Or was he just too weak to tell Hannah no? The longer his penis was trapped in the cage, the more he leaned towards the latter. Maybe if he were in a relationship with Hannah it would have been no big deal, but instead he was engaging in a highly sexual kink with a girl who thought of him more as a brother than a person she could be attracted to. And as much as he tried to deny it, he felt a perverse sense of arousal about the whole thing. He hadn’t noticed it until he was back in her presence, but when his dick strained against the cage it was almost like it was actually Hannah who was squeezing it into submission.

“Maybe they’ll surprise you,” he said. Trying to cheer her up about the potential of being separated from her new friends. “If they’re all as beautiful as you, I bet they were all able to find someone to help them out.”

“Stop that,” she laughed, punching him in the shoulder. “They’re all way prettier than me. But maybe you’re right. I bet there are plenty of guys that would agree to wear a chastity cage for a few hours just for the chance to talk with them.” The thought that the task might have been easier than she initially thought put a pep in her step and they were soon walking up the front path of the Pi Delta sorority house.

Hannah led the way up the dozen or so steps to the massive porch that stretched the entirety of the front of the house. Large stone columns lined the front of it, succeeding in giving off the Greek vibe that the architect had clearly been going for.

Standing on the porch and guarding the entrance were two of the hottest girls Noah had ever seen, a small box with a handful of phones in it sat on a table beside them. They were both wearing the same shirt as Hannah, but the taller brunette’s was visibly struggling to contain her large chest. They both wore tight, little jean shorts that showed off their long, tanned legs.

“Hannah! You actually made it,” the blonde said, sounding pleasantly surprised. “Some of us were worried that you wouldn’t have what it takes to see this last task through. Stella really whipped up a doozy for you girls this year.

“I couldn’t have done it without Noah’s help. He’s been so understanding about the whole thing,” Hannah said, blushing and looking at her feet. “Have many of the other pledges showed up yet?”

“You’re the fifth so far,” the busty brunette said, indicating the box of phones sitting next to her. “If you two would unlock your phones and hand them over, you’ll be good to go and enjoy the party.”

“What? Why do you need our phones to be unlocked?” Noah blurted out, speaking for the first time since they had arrived. It sounded like just one more invasion of his privacy.

“To confirm that you are actually wearing the chastity cage and that it is linked to Hannah’s account,” the brunette responded, clearly not too interested in hearing his complaints. “I guess you could technically just drop your pants right here on the porch but Stella said this would be easier and less intrusive.”

“It will be fine, Noah,” Hannah said, already unlocking her phone and handing it over. “You can trust them. They’re super nice.”

In for a penny, he thought. He handed his unlocked phone over, glad that all his porn viewing was done in a private browser that deleted his history immediately upon his exiting out of the app.

With the phones collected, the two older sisters broke out into giant grins. “Welcome to Pi Delta, sister!” they both cheered, offering Hannah a hug each.

With a beaming smile on her face, Hannah took his hand and led him past the sisters and into the party. The interior was like something out of a movie. There was loud music, flashing lights, red solo cups everywhere, and a room full of college girls that would make Victoria’s Secret supermodels nervous about their job security. What wasn’t like any college movie he had ever seen, other than in a few enjoyable porn films he’d come across, was that there were almost no men in sight. He could only see two of what should have been the other four men in the house.

“Come on,” Hannah said, tugging him along behind her. “I’ll introduce you to some of the other girls. And I want to find the other pledges. I want to know who is gonna become a full sister with me.”

Noah felt like he was an exhibit in a zoo as he was dragged through the press of gorgeous sorority girls, every eye in the room on him. He could feel color rising to his face at all the cheeky smiles and whispered comments he saw as he followed Hannah towards where the red solo cups were being served from.

“I figured you could use a little liquid encouragement,” Hannah said, passing him a cup she had just collected that was nearly foaming over with beer. He wasn’t much of a drinker but Hannah was definitely right that a little alcohol would help calm his nerves. Taking a long sip, he allowed the frothy beer to settle him. He was one of five guys at a party with the hottest girls on campus he told himself. He could handle another three hours in a chastity cage and enjoy the experience. And when it was over, he’d have plenty of new material to add to his mental spank bank. 

“I see some of the others,” Hannah squealed, leading the way into the center of an impromptu dance floor. His penis started to swell painfully again as they jostled their way through the throng of partying sorority girls. He was bumping shoulders with the most beautiful girls on campus and he could swear that some of them were shooting him suggestive smiles.

When Hannah pulled him to a stop, he saw that they were standing next to four young women and three guys. The awkward eye contact that passed between him and the other boys confirmed that they weren’t any more comfortable than himself with the circumstances that led to them being invited to the party.

“I’m so glad you guys made it,” Hannah yelled over the music, jumping up and down with excitement. “I was so worried that no one else would be able to convince a guy to help them out.”

“You’re one to talk,” a skinny Asian woman with silky black hair laughed. “Three of us had boyfriends to drag along. The only person I thought was less likely to succeed than you was Bailey, but here she is.” She nodded towards a shorter blonde girl with glasses. She had the picture-perfect cute nerd look going for her. “You two are just so nice and innocent.”

Noah could see Hannah blushing even in the poorly lit room. “I really didn’t think I stood a chance either,” she said. “Luckily my bestie Noah here agreed to help me out. Oh, right, this is Noah everyone. And Noah, this is Mai, Taylor, Chloe and Bailey.” She pointed to the Asian woman, a stunning black woman stacked with curves, a gorgeous redhead with the cutest freckles dotting her nose and the cute, nerdy girl in turn.

“It’s, uhh, nice to meet you all,” Noah said awkwardly. His predicament felt more real than ever now. Four gorgeous women now knew his name and would always associate him with having been locked in a tiny chastity cage when they first met.

“So how did you pull it off Bailey? I hoped the others would manage because of their boyfriends, but I only did it because Noah is such a great friend?”

“I sort of took Stella’s advice,” she said with such a quiet voice that it could barely be heard above the music.

“What?” Hannah screamed. “You offered someone sex so they’d let you lock them in a chastity cage?”

“No. No. No,” Bailey quickly said, waving her arms around and looking even more embarrassed than she sounded. “I meant her other advice. I sort of blackmailed someone into helping me complete the task.”

“You what? Is that why your boy isn’t hanging out with you?” Hannah said.

This cute little nerdy girl blackmailed someone? It didn’t seem possible. He couldn’t imagine being locked in the damned Cyberlok cage by someone that blackmailed him into putting it on. He was even more thankful that he trusted Hannah so much and knew that he’d be taking his off right when he got back to his dorm room.

“I know, I feel terrible. I just didn’t know what else to do. I was positive I was going to fail the challenge until an opportunity fell in my lap last night. I was walking down my dorm hallway when I happened to see a guy taking a pervy photo of a girl that lives on my floor. She was walking back to her room from the showers in just her towel and it was so short that like half her ass was hanging out the bottom of it. I don’t know what came over me but when I saw some random guy enter the hall before me and quickly fish his phone out to take a photo, I did the same thing and took one of him doing it. He was so scared that he’d get expelled that he practically begged to do anything for me if I deleted the evidence.

“So I got him locked in the Cyberlok cage that Stella gave us and told him he had to come to the party tonight. I also may have added an extra day to his chastity sentence as punishment for being a perv,” she finished, looking at the floor and blushing.

Oh man, that sounded brutal. The poor guy just wanted a picture to remind him of his good luck that some college coed had decided to walk down a public hallway with her ass hanging out of a towel. Noah felt his cock pressing against his cage at the thought of the careless girl and her towel. It was every guys dream to accidently stumble across a partially naked girl at college, just like in the movies.

“Oh. My. God,” Hannah squealed. “You are so bad. No wonder he doesn’t want to hang out with you.”

“That’s what I said,” Taylor chimed in for the first time. “The poor guy was probably about to race back to his room and jerk off, but instead Bailey has his dick trapped until tomorrow night. He must be so horny.”

Noah groaned in sympathy with the poor guy. He couldn’t imagine having to put the cage on if he was super turned on. Let alone having it locked for multiple days. He didn’t think he’d be able to handle more than the couple hours he was going to have to wear it for.

“Wait. Where’s Sofia? It’s gotta be past the 9 o’clock deadline. I was almost positive that she’d pull it off,” Hannah said, standing on her tiptoes and trying to look around the crowded room.

As if she had been summoned, the front door to the house opened and a very scared looking Latina slowly trudged in, followed by a man who stood at least a foot taller than her. He looked like your stereotypical jock. The blonde girl who had been guarding the door outside slipped past the two newcomers and disappeared into the crowd.

“Oh no. She missed the deadline by ten minutes,” Chloe said. She was the only one among them wearing a watch. “I wonder what Stella is going to do.”

Most of the conversation in the room had died down, leaving just the blaring music pumping in the background, as everyone stared at the two nervous looking people standing just inside the door.

An older looking sister marched through the crowd, trailed by the blonde girl who had rushed away, and came to stand before the girl that he assumed was Sofia. After a quick conversation with the cowering girl, Hannah informed him that the older girl was their pledge mistress Stella, she signaled for the music to be turned down.

“Listen up, ladies…and a few fine young men,” she said, getting a round of laughter at the mention of the five men who were mixed into the crowd, their dicks all locked into small remote-controlled chastity cages. “We have a decision to make. Unfortunately, our wonderful pledge Sofia missed her deadline by 10 minutes. I’ll leave her fate up to a vote of the whole sorority, including our five newest members who managed to complete their final task on time. I’ll give you three options and we’ll decide with a show of hands.

“First, we deem her task completed and allow her to join Pi Delta, she was only 10 minutes late after all. Second, we send her on her way and declare that having failed her final task she is unworthy of becoming a Pi Delt. Or lastly, we allow her to join our sisterhood after enduring a slight punishment. One spanking with the house paddle on her bare, juicy ass for every minute she was late.”

Conversation blossomed all across the room. Debate over how to handle Sofia being had. Noah winced as his dick tried the hardest it had since he put the cage on to force its way out. And based on the looks of the other three guys standing near him, they were struggling with the same thing.

He didn’t know where the vote would land. But he knew what fate he hoped the gorgeous Latina would face.


r/ChastityStories • • 4d ago

M Chaste,F Keyholder Voyeurism West: Chapter Eight & Nine. NSFW

6 Upvotes

Chapter Eight

 

After a toast and some quick small talk, my wife and Channel were immediately giddy and off down the beach engaged in girl talk leaving me and Andre sat together alone. “So…happy anniversary I guess?” I awkwardly break the tension. “I don’t know how you do it man, I feel like everyone is staring at me, judging me. It is humiliating.” He kept trying to strategically hold his beer in a manner to block the view, obviously forgetting that it was glistening in the sun and wrapped around his waist as well. “You get used to it. Where the hell did Channel get one of those here anyways? That is a serious piece of kit. Secure and expensive too no doubt. For what it’s worth it looks great on you though. Definitely accentuates your ridiculously toned abs.” “Thanks I guess…” “Some advice, just let go of your ego and let go of your inhibitions. It’s a kink friendly resort, and besides you will likely never see any of these people again anyway. So just own it with confidence and people stop looking so much.” He nodded in timid agreement and slowly moved his hands away from his crotch and tried to look calm and causal. “Thanks, and yeah it was not cheap at all and I am still not sure I made the right choice, but Channel convinced me. I guess she has been really struggling with our relationship lately and was unsure what the future held for us, but she assured me that changes would absolutely be necessary for us to continue happily. I don’t want to lose her, she is the love of my life. I told her I realized my shortcomings and was willing to do anything to stay with her and make her happy, so here I am.” I just nodded in acknowledgment not wanting to interrupt his venting flow. “Also, they have a very well stocked store on the island full of kinky goods. She dragged me there yesterday to get me sized and fitted into this damn thing. Picked up some additional ‘accessories’ for it too, whatever the fuck that means.” I opened two more beers from the ice bucket handing him one. We sat silently draining half our bottles before I decide it may be best to change the subject, directing it away from what I from experience could certainly guess was a tight and increasingly uncomfortable situation down below. We chatted away as normal as possible bouncing from sports, to the cars, and any other macho manly subject we could think of; if for no other reason than to help him keep distracted from his new predicament and attire. This seemed to help for a time and was working a treat until our wives returned, glistening bronzed skin oiled up and shining like a beacon against the soft white sand. With them some refreshed drinks and some new companions.

 

With them was a towering porcelain goddess of a woman, simply excreting power and authority, a red leather leash wrapped around her hand. The other end was connected to a massive and heavy looking steel collar which was locked around the neck of an absolute behemoth of a man. He simply must have been a body builder as every part of him was inhumanly massive. His muscles were impressive enough, but that is not what was drawing the attention of nearly every single beach goer as they passed. Andre was fairly jacked, especially in comparison to me, but this man was on a whole other level. That said, it was hard to tell if it was his toned body drawing the attention of others or the rest of the scene before me. I suspected the attention was more to do with the  leash, collar and tight black leather deprivation hood that was securely locked on his head with several padlocks. As they neared, I realized this was accompanied by a woven mess of rope pulled taut at the back which boosted the definition of his muscle tone. Another thicker rope was secured to the back of his collar via a D-ring at one end and tethered at the other to what appeared to be a steel hook being pulled deeply into his ass forcing his head to be held uncomfortably high as he crawled along on all fours besides his ‘handler.’ His eyes were covered in a blindfold which looked to have minuscule holes poked in it allowing some level of visibility though I could scarcely imagine it allotted much.  His mouth was covered in what I suspected to be some sort of locking gag. As they arrived in front of us a sharp tug came to first the leash halting him and then to the chord running down his back causing a muffled grown abruptly followed by the muscle toned slave rising to his knees, hands straight to the back of his head, exposing in full the massively oversized physic contrasted heavily by a shiny metal cage roughly the size of my own nestled between the rippled thighs. His muscles flexed and shifted with each breath, the glistening skin pulled tight over the god like definition. “Hello again Andre, subby, meet our new friends. Goddess Sophia here runs the femdom clinic on this island and has kindly invited us to attend this evening as her guests of honor. How lucky are we to have run into her taking her slave for a long hot walk on the beach? Well, aren’t one of you going to offer her a drink?”

 

I shakily reached for the ice bucket and offered her a beer, unable to take my eyes from her piercing gaze and her slave’s situation beside her. She took it with a faint smirk, and downed the whole bottle handing it back to me. It was about this time I realize that I too had instinctually risen to my knees and remained there before this woman, as it just seemed proper somehow. Andre however was frozen, legs spread sitting on a towel jaw dropped, eyes wide with a mix of fear and lingering regret now radiating from them as he looked pleadingly at Channel for some sign of reassurance that this was not their path ahead. With a simple snap in front of his face, the hooded, barely seeing eyes immediately met hers, she gestured some signals with her hands and he returned to his hands and knees making his way in a slow crawl towards the bar further up the beach. “Well one of you two better accompany him, he will find it hard to give a drink order with that gag fully inflated in his sad little mouth.” My wife followed suit snapping to gain my own attention, sending me on my way with their drink orders, Andre sat still frozen in fear. I walked in shock as well, slowly gaining on the crawling behemoth, I realized from behind his balls were also held taut in a humbler. Letting the humbled giant lead the way, I knew at once we were in for trouble tonight and I had better be extra attentive and caring until then to better my chances at whatever was to come. I truly hoped for his sake that Andre could check his ego at the door as well and quick. Goddess Sophia’s slave remained on his knees never once shifting his gaze towards me as I ordered drinks which came on a silver tray, this time with leather straps attached. I was instructed by the bartender to strap the tray down to the giant’s back, as per usual it seemed, and then place the drinks carefully on there so as they would not spill. Apparently, this was just common and expected so I did as told without further question. It was at this time I noticed the ankle and wrist cuffs he was wearing.

 

They were stainless or titanium to match the heavy duty collar. More shockingly they had no visible seems or locks and instead all appeared to be welded in place! My hair stood on end as a jolt of total terror washed over me, this was no game they were playing, no front or show they were putting on, this was real. This muscle toned behemoth truly was her slave and plaything and this completely docile and unwavering obedience was just the expectation for him at all times. This was all too much and I too, like Andre, found myself regretting and wondering if I fucked up, was it too late for me? Was this to be my fate as well? As I watched the giant before me crawling slowly across the screaming hot sand slower than ever, his hands, feet and knees surely burning in pain. His focus remained unwaveringly on nothing more than what was immediately in front of him and not spilling the cocktails upon his back. I ordered two tall shots of rum, downed them both and made my way back just in time for the crawling drink delivery to arrive. Andre was now on his knees at Channels feet giving her a vigorous foot rub as if his life depended on it and I was now starting to wonder as well if perhaps to a degree, it did? As Goddess Sophia handed out the drinks from her slaves back ending on her own brimmed daiquiri, she unfastened the tray holding it up before her slaves obscured vision to show one faintly, barely discernible drop slowly running down its surface. With a look of displeasure and not so much as a word, she pointed to the palm beside us where a hammock had been anchored off and with a muffled whimper, he obediently crawled towards it. Taking a sip, she excused herself, explaining that her slave had failed this simple task and must be punished accordingly and we all looked on with intrigue as to what this would mean. Andre and I with a sense of impending terror and doom, our wives with an alarming look of excitement and inspiration. The hammock was unhooked and a small padlock swiftly secured his hands behind his head to the tree anchor. His legs were spread wide and ankles tied off with rope behind the tree causing him to fall what looked to be painfully forward. His back was arched sharply backwards and his wrists and collar seemed to awkwardly be supporting the majority of his weight. His abs now appearing more chiseled and cut than ever;  the skin of his abdomen was drawn over the flexed and strained muscles like a drum, a brand clearly visible burnt into his chest long ago. Goddess Sophia then walked towards the bar, where she quickly borrowed the chalkboard cocktail sign stuck in the sand behind. She wiped it clean and wrote something else in its place before returning with it under one arm. She stuck it in the sand beside her helplessly exposed and uncomfortably bound muscle slave and made an inhumanly loud announcement to anyone within earshot. “Ladies and gentlemen, this is my slave. He has failed me. He deserves punishment but frankly I cannot be bothered to give him the privilege of my divine attention if he cannot obey a simple task. So, I have with me one-hundred coupons for 15% off at our island sexual superstore by the main entrance. If you would like to have one of these coupons the price is simple. Make your way over and complete this one easy task. Help me punish this useless bitch and claim your reward. Step right up folks! Come and get ‘em while they last!” As a few interested bodies began to come our way, goddess Sophia returned to her drink and my heart nearly stopped beating. What she had written on the sign was quite devious but effective, I would never displease her no matter what! Coupons for kicks! Destroy my slave’s worthless balls! 5 kicks=1coupon, 15kicks=2coupons, 25kicks=3coupons, 50+=50%off. Holy fuck! Me and Andre exchange and look of shared terror, her slaves chest was now heaving with the anticipation of the impending torment. Helplessly bound and forced to look straight ahead by the hook still tugging deeply at his ass, his wrists and collar padlocked to the tree, there was no way of budging at all. With that the humbler was removed and for the first time his caged cock and balls swayed freely between his widespread tree trunk sized thighs.  

 

My stomach was flipping as I massaged Mistress’ full body, Andre doing the same to Channel. Both of us tried to ignore the agonizing and brutal punishment being continually dished out just feet from us as our ladies made unbelievably normal small talk with Goddess Sophia about shoes, outfits and their favorite restaurants back home. Goddess Sophie causally turning on occasion to hand out coupons as they were earned. This had been going on near an hour at this point and there was still a sizeable stack of coupons left. The muscle toned giant of a man had slumped into a heaping pile of defeat and agony; his will clearly residing to his fate. I was certain at this point the only thing keeping him upright, masked head looking forward, exposed and on his knees was the hook deeply seated in his ass and the steel cuffs on his wrists and neck which now took his full weight as he hung there almost lifelessly heavily breathing. I had lost count of the hard kicks he had endured long ago as I was now trying to drown out the sound of the hard slapping thuds and guttural groans from deep within the helplessly anguished being before us. As the sun began to sink low, Anna and Channel both decided they were hungry, but first that they would like a discount as well and decided to take their turn working over his now deeply bruised and purple balls, both opting for the 50% option thanking Goddess Sophia and saying they would see her after dinner for her seminar. Andre and I were ordered to thank her for the show and motivation and follow our wives back towards the restaurant for a meal, my appetite thoroughly now gone.

 

As I wasn’t eating anyways, Mistress ordered me to kneel besides her throughout the dinner to massage her feet as they were sore from kicking earlier. Andre sat still, almost silent and staring into space until he was asked to do the same. I suspected that ‘asking’ would soon shift towards instructing for them as well. As our wives finished their meals, we were dragged along the path in complete and utter terror towards the seminar building the image of Goddess Sophia’s beaten and defeated slave still fresh in our minds. His balls were still enduring the punishment even as we had left for supper. Would he be here as well? Hell, would he even be in a conscious enough state to get here or had she just left him there still anchored, kneeling to that tree? The answer came suddenly as we entered the conference room, to find him horizontally suspended in a full body cage on full display, about two feet off the floor. The steel cage had been painstakingly fitted tightly to every inch of his body disallowing even the slightest movement of any kind. His green eyes were now visible. Bloodshot, puffy, and deeply entranced with a residual sense of hopelessness no doubt from recent substantial and severe fate. He was completely hairless, no body hair, shaved head, not even eyebrows. Attached to his mouth a funnel gag with a small sign hanging from the cage welcoming the use as toilet and disposal of any other liquids desired. His balls swollen and bruised now looked twice the size, and dark. This women was truly insane. My heart dropped further as we came to the stage, riddled with everything you could possibly imagine the kinkiest and wildest of sex dungeons and a big sign off to the side, volunteers required. My fate was literally written on the walls, I could sense it.   

 

Mistress had immediately signed us up, Channel did not do so just yet, still timid in her new role, to Andres great relief I am sure. I however, was told to get on my knees on stage and wait but not to worry. It was a light entry level instructional talk tonight. I did as instructed, a muzzle was swiftly fitted to my mouth which was tightly latched into place with a series of straps running around my head and nearly over my eyes. My hands were then cuffed and locked behind my back leaving my cage on full display to all in the crowed and nothing for me to do but sit their silently and look pleadingly at my Mistress in hopes she would change her mind. I was met only with a gaze of intense lustful excitement. I was fucked. As the lesson began, I sat obediently on my heels at Goddess Sophia’s side listening intently just as her own slave had done fearing anything even closely resembling his fate should I fail. She welcomed all and told them to enjoy her slave behind them for the evening as he was free for use and introduced me by name and as a brave, helpful and willing volunteer. I burned with blushing red embarrassment, a rope of nervous precum leaking slowly towards the stage. She continued on with her lesson, all of which seemed purely academic and not requiring me. This was a great relief, though I scarcely heard a word of it in my current state of completely mortified humility. Then I felt a hand lightly slap my face and snapped too. “I said up slave, on your feet now!” I obeyed faster than I even knew possible and looked pleadingly with apology at my having zoned out. I was led to what I knew from many years of selfish porn consumption to be a saint Andrews cross and my ankles and wrists were secured, my ass now on full display to the crowd behind. “Now we will begin our lesson on impact play, punishments, the various instruments that can be used and where on the body is safe to use each.” I swallowed hard as I prepared for the pain to come.

 

Fortunately, Goddess Sophia went somewhat gentle on me only using each implement a few times, some hurting far worse than others. I almost leapt out of my skin the first time the whip made contact with my shoulder blades. As the whole of the back half my body lightly burned in various shades of red, I was spun around and resecured, this time facing the crowd, with light tears in my eyes more from humiliation than anything else. She demonstrated everything once more on my front half, when done I was swiftly flipped backwards so I was now looking nearly straight up at the roof as she moved onto cbt, ball busting and the soles of my feet. I was stood back up and told with a gentle whisper that the worst was over and I had done splendidly, so now time for some pleasure. I was let free and led to what seemed to be a makeshift shower with a long hose that was swiftly stuffed up my tight ass as I was used to show how to properly clean out for anal play. This was the most humiliating moment of my life as I was hosed out on stage by a Goddess, muzzled and cuffed before a crowd looking at me like an instructional dummy in health class. When the water ran clear, it was shut off and I was lead to a bench like piece of furniture, bent over it face down and secured tightly with ankle, wrist, thigh and back straps. “Now to conclude todays lessons. Prostate health, milking and pegging. As a bonus we have another volunteer showing off one of our retail toys growing in popularity. Andre come on up!” I was mortified to see him bashfully join me on stage, muzzled and caged same as I, but this time with a massive fake dick attached to the front of his chastity belt. He was shown off, his full belt device discussed as well and then attention turned to the helpful attachments which could be purchased with it. He was then instructed to kneel in front of me and look into my eyes while my ass was prepared for him. He did so, sharing a mutually apologetic and embarrassed look deep in each other’s souls, our faces just inches apart. Odd sensations washed over me as various toys were inserted, various methods were shown to milk me for prostate health and before long a clear cup was help up to the crowd with an impressive amount of cum in it. I had come to realize it was all mine despite the fact I felt almost nothing, it had been dribbling out the whole time. My pent up hyper full balls were now empty, yet I felt little to no relief. Andre was then led around behind me and instructed to fuck me long and hard while Goddess Sophia wrapped up her seminar which he did so with a vigor as if he were fucking me with his real cock. I felt like I was about to be split in half, but as the initial discomfort faded into immense pleasure I slipped into submissive bliss. To my complete shock before she concluded her lecture I had a full body shaking, trembling, dry orgasm as my newly cage friend fucked my ass with a strap on in front of a sizeable crowd. They all applauded our efforts, and then Goddess Sophia’s as she concluded and told all to have a wonderful evening and go pick up some toys for their own pleasure at the store on their way back.

 

I must have effectively blacked out as I came to slumped over Andre’s shoulder just as we entered one of our villas. I was laid out still groggy on the lounge by the pool handed a beer and hit in the face with droplets of water from the splash back as he dove into the pool beside. A while later the world came back to me, my ass felt hollow and my full body ached a deep muscular ache. He apologized profusely for the evening as he had no choice and handed me another beer. I took it and told him no apologies necessary, thanked him for the lift back with a little chuckle. We sipped our drinks and we just chatted and reflected about the day’s insanity and our prospective futures within our own relationships. I later learned that our wives had went for drinks with Goddess Sophia and then were off to the super store to use those 50% off coupons. I suspected that we should both expect some serious changes and fun not just for our last few days, but when we got home as well. Surely this could not be good news, or could it?

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Chapter Nine

 

That fateful vacation for my wife and I was six months ago. Our dynamic had absolutely been permanently changed for the better I soon found out, but it was a hard transition. Our life was now far more kink oriented, we were in a full female dominated relationship and I had not had a full orgasm since before we left for the trip. Hell, I had not even been allowed so much as an erection. My cock cage was permanent at this point and had not once been removed for anything. Andre and Channel stayed in touch, we had even managed to get together a few times since then as fortunately it turned out that they lived just a few hours from us. He too was now locked nearly all the time, though Channel still loved to use his massive cock from time to time. So he was at least lucky enough to get released for sex whenever she wanted it, which was roughly once every month or two from what we had gathered. Mistress Anna, as I was now to referred to my lovely wife, was now my owner and stepping into her role quite comfortably. I have been collared, it was a thick heavy collar, though not so much as seen on the island though. Mine as well however was pretty much never to be removed again with the matching set of ankle and wrist cuffs nearly permanently installed as well.

 

Miss had drawn up a slave contract based on one Goddess Sophia had provided her with. This was gifted to me a few months after our return when she asked if I would make it official and become her lawful and true property to which I agreed. We had it legally finalized with Channel and Andre there to bear witness. I am now fully hers to do with as she pleases. I never wear clothes unless in public and have also been told my days of orgasming like a man are over. I obediently serve her and all of her new kinky friends every wish and desire at all times. I have most recently been marked with a few tattoos of her choosing showing that I am now her property. It was a hard transition, but I truthfully find that I am happy and content in my new role. My life has become far less complicated and in many ways more fulfilling. My sole purpose now is to obey and please my loving wife and Mistress, nothing more and nothing less. All else is irrelevant and does not matter. She has orgasms as she pleases, frequently takes lovers with my full support. I am even lucky enough to quite often be included in their love making. I am regularly face fucked, pegged or having my ass used by her and her lovers, which I too have found greatly pleasurable. My ass and balls are regularly beaten for maintenance or for punishments on the rare occasion I fail to submit to Mistress’ satisfaction. We are scheduled to return to Voyeurism West in one month’s time for a final audition for a permanent position I am told. Goddess Sophia recommended us for full-time employment, as entertainment and educators, which of course Mistress eagerly accepted. If all goes well, we will be packing up here for good and moving there indefinitely. I am told that I could potentially be made available for rent by guests as well should Mistress choose. At the very least we would be required to give regular lessons and demonstrations, but the rest of our time we could simply enjoy the island as our home in one of the private villas on the outer edge of the resort reserved for the full-time employees. If our application was accepted however, all my hair would be required to be lasered off over several sessions, a new cage would be welded on with no chance of removal and my clothes would all be discarded as they would no longer be required. I would live out my days a permanently denied show pony and slave for hire, should she chose, at the resort. Either way I would spend the rest of my days serving Mistress Anna and whomever paid to loan me in a tropical and kinky paradise. How did I ever get so lucky? Would they accept our application and recommendation? Fuck me I hoped so! Our house went on the market this morning and all our stuff is on marketplace. Our destiny awaits, one way or another we are headed back to the island that made us who we are now.

 

Our house had sold, my possessions were sold off, my last scraps of clothing were thrown into a donation bin and soon the tiny boat awaited. We were greeted once more by a smartly dressed man in white linen, this time my wife was addressed as Mistress Anna and I her slave was told to get the bags and follow behind. I did as instructed, wrestling the three large suitcases of all we had left towards the welcome center. This time we did not enter, we went left in the opposite direction of the resort to a much larger and far nicer waterfront villa than we had been shown to last time and were welcomed in. Upon the table sat a stack of papers and a single golden fountain pen. “Welcome to your new home Mistress Anna. If you would go through and sign these documents, I will escort your slave husband to the dungeon quarters and secure him properly for his final preparations. We will mark him with our official brand on his chest, give him his slave numbers on the back of his head and his new cage, cuffs and collar will all be permanently sealed in place just as soon as you sign.” With a quick thumbing over, Mistress picked up the elegant pen, signed several times and handed it all to the man while I knelt off to the side in silence. “Very good madam. Now, would you like your slave to be returned to live here with you in your home full time? Or would you prefer we prepare a cell in the servants housing quarters?” My cock had sprung to life with more vigor than it had in months. We had gotten the position, but nothing was mentioned about slave quarters! Was my once sweet and vanilla wife really considering living here without me and confining me to a life of service and solitude as a kinky island slave for hire? “I think I’ll keep him close by with me, I still have many needs of my own that he caters to. But maybe I could reserve one of those rooms for if he should ever disappoint me? Afterall, all things fade, I may wish to use it more indefinitely one day.” I sighed notably with relief. “Since you were so kind as to offer it however, I feel inclined to accept your generosity, so yes. If you could be so kind as to prepare a cell for subby here, I shall get settled in for a time on my own and he can get a glimpse of motivation to strive for perfection in his service. Shall we say a week in his cell to kick things off? No, we had better make it at least two while his markers heal.” With a smiling nod from the man, I was led away wide eyed in disbelief at my ears towards the back room of our home.

 

As we left the house out the back door, I looked back with pleading eyes towards mistress, she returned a sadistic wink and endearing grin. I found myself led some ways away and into a sterile and soundproofed room with heavy chain restraints hanging from the white tiled ceiling and walls. I was tightly secured to restraints and a button was pushed. My arms and legs were all drawn apart until the chains painfully tugged at my joints and my feet were lifted and inched off the ground until the very tips of my toes just scarcely touched. An inflatable gag was placed in my mouth and pumped up to what felt like far too full and what appeared to be a welding cart was rolled in by a heavily tattooed woman. “Shall we begin lovey? Not that you have much choice anyways, your Mistress and owner just finished signing your life away, so you are all mine now I am afraid. Anyways, this may hurt a bit, better get used to it.” She disappeared around the back of me and I felt needles carving into the back of my head as a gentle hum vibrated my skull. As she did this, several others entered with hair removal lasers and zapped every inch of my body. When they had finished, the tattooed woman removed my cage, for the first time in more than half a year, my dick had been freed. This was short lived however as from her cart she picked up a shorter and far more secure looking model. As she held it up to my still flaccid penis, she shook her head and picked up another. She did this several times before her lightbulb moment seemed to trigger. Standing up she left the room through the door behind me. I heard footsteps approaching down what sounded like a narrow hallway and soon felt the cold touch of metal once more. This time not on my crotch though but my hips and ass first. She had returned with a full belt design. I felt my heart skip a beat as something similar to a metal pair briefs was a snuggly sized and secured on me. My entire crotch was fully encased, as was my ass apart from a small panel at the front and hole in the rear. A curved metal tube roughly four inches in length was then fed into my urethra, a threaded pin securing it in place via my Pa piercing. This was then secured rigidly by a short snug tube that was welded into the belts front panel. The woman popped the front into place and flipped down her welding mask. Within seconds my poor cock was engulfed in immense heat. Moments later I had nearly blacked out, only to come to felling the still hot metal on my crotch, neck, wrist and ankles.

 

These were accompanied by the familiar sting of a fresh wrapped tattoo on my skull and a painful brand on my chest. As my eyes slowly lift and adjust to the now dark, I am met with the sad look of a ridiculous and truly hopeless being before me. Nothing but mindless servitude, horny desperation and defeat in the now blank stare. It was the same look I had seen those months ago in the muscle toned slave through his mesh hooded eyes. A mix of deep despair and odd contentment in ‘its’ lot for ‘it’ was a man no longer. No, ‘it’ was a mindless, obedient slave. ‘It’ had no goals, no dreams, no aspirations. No, ‘it’ simply had one purpose and was well aware of that purpose. Mindless servitude to any and all who sought it. This was ‘its’ last remaining purpose in life. Those sad pleading eyes he saw all those months ago that stared back at him, now suddenly seemed less sad, just hollow. There was not a thought left behind them, just a burning desire, no a calling, to obey and serve without thought or hesitation. The only difference is that those eyes were a different color now and the body they belonged to was not that of the behemoth muscle toned slave from their last visit. No, this body was more slender and weak. With a hint of familiarity and a shining steel full belt securely welded in place. This body was that of my own, or at least it used to be. As I stare into my own empty slave eyes, suspended spread eagle still unable to reach the ground fully, it is as if my soul has been replace. I blink once long and hard and my former life is forgotten to me, a thing of the past. Max was no more, this body, this mind was now that of slave 274 or slave M., to my once loving wife turned sadistically kind Mistress. ‘It’s’ former lustful desires and hopes were gone, replaced only with an overwhelming need to selflessly obey, serve and please as a good slave should. The lights flip on quickly and the soft but stern voice follows. “Good morning slave, ready for the first day of the rest of you docile, subservient life?” I nod frantically unable to see or speak with tears of happiness and excitement welling in my eyes. The chains rattling and tugging at my joints in my desperation to begin. “Good boy, I’m going for drinks with Goddess Sophia, I’ll be back tonight. I had better not let you get too comfortable though. She disappears behind me and a massive dildo is pressed deeply and swiftly into my ass through the rear access hole. She returns to the door turning and blowing a kiss as she flips the lights off and a heavy bolt slams shut on the other side of the steel door. I was in complete blackness now as I began accepting my situation and getting familiar with the girthy fullness of my ass. That is when the mechanical hum began. A spurt of lube flowed from the tip of the massive cock which then began to move upwards stretching me even further and deeper.

 

The speed and depth increased gradually with each thrust, before long what must have been a twelve inch dildo was ramming its way home into my ass with savage verbosity alternating thrust, depths and speeds periodically. I trembled and shook as my prostate and balls drained out onto the floor time and time again. I gave into my fate. A sense of satisfaction and contentment washed over me, mind and body. I was home, I had found my calling, my purpose in this life. I was to suffer and serve for the amusement of others. Especially for that of Mistress Anna. I was a lowly slave kept here to be used and abused by those superior to me. My brain was to erase and be filled with but one thought at all times, and from this day forward, I was happy to oblige. My thoughts and worries all faded away, the discomfort in my ass faded into an indifferent dull sensation. One word repeated itself in a soft cooing hypnotic voice within my brain as my body became a slave to itself as well. “Obey. Obey. Obey. Obey.” This was my divine truth, my sole purpose from this day forth. I would be a good boy and obey no matter what, I had to. It is who I was, it was all I knew now and all I desired. As I stare into the dark abyss, my ass being pounded mercilessly and my joints burning under my own hanging weight I felt nothing. I must endure. I must obey. Perhaps if I did good, Mistress anna would allow me to live in with her as her personal servant in a couple weeks time. Or perhaps this was to be my new home?

 


r/ChastityStories • • 5d ago

M Chaste,F Keyholder The Full Experience: Part 2 Jaden's First Day NSFW

65 Upvotes

Hi, I'm Jaden.

I was just given my first chastity cage -- a flat metal one. A woman in the next apartment building who made me call her Goddess put it on me.
https://www.reddit.com/r/ChastityStories/s/SqpQxOcFgV

When I got home, I went straight to the bathroom and tried to get it off. I was still hard in my flat metal cage.... well "hard"... somehow. It feels like a lump above where my cock used to be, but it's really uncomfortable. I tried my worst idea first -- I tried to slip my balls through the ring. That hurt. My nuts aren't exactly big, but I could barely breathe for, like, 10 minutes after straining to try to pop my left nut through the ring. Maybe this is why my last girlfriend called me a "dumb blonde". Shit. That somehow made me "hard" again. I swear this world has it out for my balls.

Next, I tried lotion, which failed. Guess I wouldn't be using that tonight for leisure.

I had an unpleasant time trying to take a piss. That sprayed all over my bathroom. I ended up dropping to my knees to keep it close to the toilet bowl that first time. Had to cleanup the floor and take a shower. I took extra care to make sure it was completely dry. I'm a lifeguard, and the last thing I want is a wet crotch. Even used my blow dryer. And no... soap and shampoo didn't help get the cage off either.

Sleep was hard to get. I couldn't lie face down because of the pressure of the cage, and I kept getting hard. I'd usually jerk in bed, but all I could do was move my balls around a little. It was quite frustrating. I must have gotten to sleep around 2am, though I kept waking up from the pressure of the trapped erection. Shit. I didn't realize how hard I was all the time. The "morning wood" wasn't any better.

I almost called off work, but I need the money. I can barely afford my apartment and college. I really should quit the Lifeguard gig, but I like it. I get to look at the ladies at the beach, and no one can tell because of the sunglasses. That proved to be a double edged sword today, as I could look all I wanted, but it would just make my cock beg to be released.

As always, the world seemed to be targeting my balls. My average day finds ways to bring me to my knees, and I soon found out the cage makes this worse. First, it sucks to run in. Big waves today, which could knock over a grown adult. I saw someone needing help in the shallows, so I jumped off the lifeguard tower and sprinted toward them. That sucked. She was panicked from near drowning and managed to kick me in the nuts as soon as I got to her. Then she grabbed onto me and pulled my hair and drove her knee into my nuts. The cage left my balls no where to go, so each hit slammed my nuts into the metal cage. She's lucky I'm a damn good swimming and can hold my breath because I couldn't breathe. Then a wave knocked us over when I almost had her out. She went under and grabbed. My.... fucking... balls. Clutched them like they would save her life. Then then grabbed the cage and yanked as the water tried pulling her back out. I literally battled her to release her death grip on them before finally getting her out.

She didn't need any extra help, just needed to breathe and calm down. She thanked me and then looked at me like she knew. She knew I had a cage on but couldn't say anything since I just saved her life. The look she gave me. God that was embarrassing.

There was this kid, there every Tuesday this summer. I swear he picks my lifeguard station. Then he tries to get me to play soccer with him, but, like, I'm working. I recognize him every week, and every week he gets mad that I won't play and throws the ball at me in protest. I stupidly forgot this because I was distract by my cage. I'll be damned if that ball didn't connect directly with my cage and my nuts. Got in trouble with my supervisor again when she found my writhing on the ground. She said I was sleeping on the job. Tomorrow, she wants to have a talk with me.

My shifted ended, finally. I had a slight sunburn, but it was okay.

It was 5pm, and Goddess was expecting me in an hour. I thought about not going, but I couldn't get this cage off. She had the key. Maybe if I marched up to her and demanded it. No... god no. She'd keep me locked up longer. Maybe... if I gave my best sad eyes, just... made my blue eyes big, she'd have pity. That used to work with my old girlfriend. That's it. That's the play.

At 5:59pm, no one was in the hallway. I knocked.

She answered. Topless. I lost all train of thought. She grabbed me by my cage through my shorts and pulled me inside.

"Welcome back, Jaden. Have you been a good boy?"

"Yes, Goddess." I had never been harder, so to speak.

"Let's get you ready for the evening," she said as she lifted my shirt off. Why did I just comply? She grabbed the waistbands to my shorts and briefs and pulled them down both at once. I looked down, disappointed that there was just a flat cage and my balls. My cock strained with nowhere to go.

"Are you ready to see what I have in store for you tonight?"

Any ideas I had of rebelling, of telling her off, demanding freedom, disappeared as she brushed against me with her perfect breasts. They were so soft. So smooth...

"Yes Goddess."

"Good, come with me." She led me by the hand to the couch. She sat down and placed me standing in front of her.

"Let's get you ready."

She pulled out a masssage gun and turned it on. It hummed quietly. Then she place the vibrating end on my bulge just above the cage. Oh my god that was amazing. All I could do was show this stupid smile. I just wanted to cum so badly. I wasn't hard though, just enjoying it. I never imagined in my wildest dreams I'd enjoy an orgasm this way. I'm sooo close. She moved it to the cage and vibrated it, and rotated between the two every so many seconds. I might actually cum like this!

Then she stopped and shut if off. Instinctively, I grabbed her wrist.

"Wait! I'm almost done."

Shit. I knew was in trouble by the look in her eyes let go immediately.

"I'm s-sorry, Goddess."

"That's strike one, Jaden. Good boys don't get strikes. Good boys, don't touch me unless I tell them to."

I had always just cummed when I wanted to, whether by my own hand or when having sex with my old girlfriends. Now, I felt guilty for wanting it, but god, I was so desperate to cum.

"W-what does a strike mean?"

"That depends on if you make it up to me."

She sat forward so she was on the edge of the couch and leaned back

"Eat."

I knew how to eat a woman out well. This was my chance to get back in her good graces! I knelt and worked, using my tongue like a pro. When she came, she was panting. I was so proud. Maybe my turn was coming.

"Good boy, Jaden. You've earned a washing."

She stood up and led me to the bathroom. There was a standing shower. She turned it on and pulled me in, turned my back to the water so it hit my back. Then knelt and cupped my balls in one hand, reached between my legs, and placed her finger in my ass. I had never had anything placed there before, but I was so horny that I surprisingly came with little effort. I looked down as it happened. My cum shot out of the little hole with one strong shot, then cum dribbled out of the holes and down my balls. It was a bit anticlimactic, but I was relieved. She stood up, washed her hands.

"I wash you."

I nodded, "Yes, Goddess."

She washed me more thoroughly than I had ever washed myself, and I watched as she washed herself. I was almost hard in my cage again as she washed her breasts and hips. She even bent forward low to wash her legs. When we exited, she dried off. Then she produced a key.

"This is only to dry you off. Nothing more."

With the turn of the key, the flat part of the cage came free, and she popped the ring off of my balls. My cock was pathetic. She dried it quickly. I tried in vain to thrust my hips forward to try to enjoy being touched. It didn't matter. It didn't get hard. She put the ring back on, and then the flat part, and I was locked again. All I could do was sigh in frustration. She left the bathroom for a moment.

There. On the sink! The key! If I grabbed it and tried to unlock the cage. if I could unlock it, I could pull out the little bronze locking mechanism later and be free between visits, and she'd never know. But.... the key didn't work.

I heard her clear her throat and looked up to see her standing in the doorway. She had on a strap-on cock that was partially inserted into her vagina.

"That was a fake key, Jaden. It's not for your cage. That's strike 2."

"No..." I whispered. I had fallen for the bait!

"I'll show you what I do to bad boys."

"Please, I'm not a bad boy."

She led me to her bedroom. She held my balls and made me lie on the bed face down and tie my hands to the posts.

"I'm good, but I'm fair. Aren't I Jaden? Say it."

"You're good but fair, Goddess." I said as she mounted me. "You'll learn what fair really is."

She inserted it into my ass and rode me until she was content. It kinda felt like having a reverse poop. She moaned behind me. Then she untied one arm and turned me over, tying it again to the bed post.

She produce another cage, which looked nearly identical with one major difference. There appeared to be a little cone tucked inside the flat cage.

"Do you know what 'inverted chastity' is, Jaden? No? Let's get you fitted and on your way."

This was worse. Far worse. My tiny little cock was stuff up inside even tighter.

"I have a business trip tomorrow. I'll be gone a week. I'll see you next Tuesday at 6pm?"

One week?!

"Y-yes Goddess," I whimpered.

"Now promise me you'll be a good boy, Jaden?"

"I'll be good, Goddess."

"Good."

She dressed me again. Briefs first, then shorts. Then she placed my shirt on me and sent me out the door.

In the hallway, I sighed.

"One week..." I whispered.


r/ChastityStories • • 5d ago

M Chaste,F Keyholder Snowed In (Part 2) NSFW

40 Upvotes

Read Part 1 here!

The wind whipped snowflakes into Tanner’s face as he trudged toward the library. The storm hadn’t abated since Monday and lake effect snow was piling up all over campus. The whirling winds he struggled to lug his backpack through to go study were nothing compared to the whirlwind romance he had experienced just 4 days ago, however. From meeting the new girl on his dorm floor to falling asleep with her, naked and entwined in her bed, in just one day. And that was to say nothing of what had happened with her in his own dorm. He could still imagine it, and he had been playing it over and over in his head. Watching her dangle the tiny keys off her finger. Laying the full weight of his body against hers. Seeing the blush spread across her face as she came underneath him, hard. And the horrifying realization that he had cum in his chastity cage as he pounded her to orgasm with that strap on belted to his waist.

He focused on the muffled crunch of snow under each step, the jumble of textbooks in his backpack weighing him down, anything to try and ignore the hard plastic cage imprisoning his cock. Shivering, teeth chattering as he walked, his cock threatened to shrink back into his body in the cold. It wasn’t the most uncomfortable the cage had ever been. But this was the first time he had ever been locked for more than a day, and he couldn’t even unlock himself if he wanted. Veronica had hidden the keys somewhere in her pink-plastered dorm, and he hadn’t seen her since he headed out for classes on Tuesday morning. He must have checked himself in the mirror 20 times before he left the dorm, trying to notice if the cage was obvious from any angle. It was, in the gym shorts he wore to sleep, but he risked it on his dash down to the bathroom to brush his teeth at night. For this trip to the library, he’d slid into a pair of thick black jeans, protection against both the biting wind and embarrassment. He looked down one last time before he climbed the stairs to the entrance, just to be sure.
Warm air and the smell of books blasted Tanner as he pulled the heavy door open. He strode past the cafe and circulation desk and climbed the large circular central staircase, set on finding a table in the quiet side of the building. With each stair he felt his locked cock shift and sway in his jeans. Reaching the top, he hiked up his backpack and set out for the stacks. His hand was wrapped around the door handle to the quiet side when he caught movement out of the corner of his eye.

“Pssst! Tanner!”

He froze at the sound of the loud whisper. Veronica was twisting her body over the black puffer jacket on the back of her chair toward him, motioning him toward her. 

“Over here!”

Tanner felt his heartbeats quicken. He was conflicted. He imagined walking over, her dropping those light metal keys into his hand. If he had them, he’d speedwalk to the bathroom and unlock his cage immediately. But just as much of himself wanted her to hold his keys. He craved giving up control. It made him feel exposed and alive in equal measure. Of course, he couldn’t ignore her, he hadn’t seen her in nearly a week. And it was bad form to brush off someone you’d just had sex with, even if technically his dick had never been inside her. 

Veronica smiled up at him as he made his way over to her table. Her backpack was open and papers spilled out, and the table was a tableau of printouts of paintings, notes, and flashcards. He doffed his backpack and sat across from her. “Good to see you’re not snowed in anymore,” he said, awkwardly. She put her elbows on the table and propped her head up, waiting for his next sentence. “Big test coming up?”

“Tell me about it. Have to name 75 paintings, their artists and years. And I haven’t even started studying for the long response questions.”

“Makes my test on Tuesday look like a cakewalk. I’ve just gotta do some math.”

“Okay, well, I’d rather do this than math.” She picked up a pile of flash cards, shuffled it, and dealt one. “Hell, Bosch, 1490.” Veronica flipped it over with a flourish. “See? Easy. If it’s fucked up, its Bosch.” Tanner leaned back in the hard wooden chair and admired her. Her dark brown hair was done up in a high, tight ponytail. The bright light from above made it shine. She was wearing a tight black Lululemon jacket, zipped up over her chest. He could see just a hint of white above the zipper, and he had to wonder if she was wearing the same white sports bra he had seen her drop his chastity keys into before she turned and led him out of his dorm. Shuffling the stack and drawing again, Veronica furrowed her brow. He watched her glacier blue eyes dart over the card. “Damn it. I can never get this one.” She flipped it. “Van Eyck, van der Weyen, how the hell am I supposed to tell the difference!” she said, a little too loud. 

“Was I not a good enough study buddy?” Tanner looked up at the new voice coming from above him. He saw a short girl with blonde hair looking at him intently. He looked back down at the table and realized half the notes were facing him. 

“Oh my gosh, I didn’t realize someone was sitting here,” he blurted out.

“It’s cool. You wanna take the test for me?”

Tanner tried to get out of her chair and kicked his bag over. Veronica stifled a laugh. “Paige, meet Tanner. He’s the guy from my dorm I told you about.”

Told you about? Tanner thought. His mind raced. What else was there to tell her about other than that they fucked, that he was locked in a chastity cage. Would Veronica brag to her friend about taking his keys? Hey Paige, here’s the guy whose dick I’ve got locked up!

“Oh, cool,” Paige said. “Thanks for keeping my girl fed. I told her she had to go to the grocery store before the storm hit, but *someone* didn’t listen.” Tanner stood up from the table and watched Paige slide into her seat. She was petite, and wearing a black and yellow Crow Mountain Football sweatshirt. On her tiny frame it was nearly down to her knees. Probably her boyfriend’s, he thought. He looked at Veronica, and she looked up at him and rolled her eyes. Paige reshuffled her notes absentmindedly.

“I’m lucky Tanner here is such a great cook. Or at least he tells me he is. Makes a good mac and cheese though.” Tanner mock bowed, Paige smiled. “Hey, don’t pull an all nighter in the lib. Paige’s sorority is throwing tonight, and I need a plus one.”

“Oh no, I was really hoping to spend all night here.” He felt his heartbeat again. Was he her date? 

“You’ve got a suit right? This is a formal affair. You won’t want to miss it.”

“Yeah, I’ve got one. Tie too?”

“Duh. Am I gonna have to list your whole outfit for you?” she teased. “Let’s see, shoes, socks, belt-”

“Okay okay, I get it. Pregame, or should I just meet you there?”

“225 West Street, 10 o’clock sharp, or fashionably late. Your choice.”

“I’ll be there.” He grabbed his back and turned to walk away.

“Hey,” Veronica said, before he had taken a step. She kicked her left leg out toward him. His eyes traced down her long black leggings. He caught a glint right above her furry Ugg slippers. Something dangled off the pale skin of her ankles. An anklet, with a letter V charm. Next to it, his little silver key. His eyes darted back toward hers. “It’ll be fun.”

Tanner couldn’t focus on his study materials at all, even in the quiet of the library. Veronica was wearing his key. No one would know what it went to, he kept reassuring himself, they would just think it was a cute little charm. He looked over the open pages of the textbook in his lap, sighed, shut it and tossed it onto the table with a resounding thud. “Shhhhhhhh,” someone whispered from a few rows over. Whatever, he thought, and gathered up his notebooks. He stuffed it all into his backpack and walked through the building, steeling himself for the cold slog back to his dorm. He was walking at speed and raised his arm to brush the door open when a loud beep pierced the quiet of the space. What the, he thought, and froze.

“Come back,” a voice called out, and he took two careful steps backward. A library volunteer was walking quickly toward him. “You’ve gotta check that book out.” 

“But I don’t have a book.”

The student volunteer looked at him through huge bookish glasses. “Then what set it off?”

No way, he thought. My cage is plastic, it shouldn’t set it off. It couldn’t, right? He took in the volunteer. Her breasts pushed out from underneath her tight white sweater. Tanner could feel his cock growing in his tight cage, and feel his face flush with embarrassment. “I didn’t check anything out, I swear,” he said and slid his backpack off his shoulder. “Look, just my textbook.” He stood back up. The volunteer bent down to inspect it. Tanner was staring down the top of her sweater. The middle of her nude bra was visible, and his cock was getting painfully hard inside its cage. She looked up at him and squinted. 

“Okay,” she said and nodded toward the door.

“Could it be my belt?”

“Yeah, it’s probably something metal you’re wearing. It’s really sensitive. Whatever, you’re good to go.” She stood all the way up. The student reached up with both hands and pulled her sweater up further over her chest and leered at him. He realized just how much he must be blushing. Tanner turned and busted out of the library into the cold. 

The tie dimple was perfect. He reached up and wiggled the knot tight one more time, taking in his handsome reflection in the mirror. Damn I look good, he thought, then reached down and tugged on the cage between his legs, making sure it’s snug before setting out. Turning back to his desk, he pulled his suit sleeves down tight and polished off the beer he’d been working on while getting dressed. He was giddy with anticipation. What was the party gonna be like? He didn’t know Paige, let alone anyone in her sorority, but the strict dress code made him feel like it was going to be a can’t-miss affair. He crushed the cheap lager can in his hands and threw on his jacket, dress shoe heels clacking on the floor as he trundled down the steps and out of his dorm. 

His broad shoulders and purposeful stride instantly contracted as he stepped outside into the blowing wind. This must be below freezing he thought, pulling out his phone to check his directions one last time. The blue Google Maps arrow spun lazily as it ascertained his heading, then he set out toward his destination, stepping carefully over the snow in his slick leather soles. 5 fucking blocks. He put his head down and powered through, headlights from the sparse traffic illuminating the flurry of snow falling in front of him.

Two freshmen boys loitered outside the big brownstone apartment. This was once a rich town, of railroad owners and coal mine investors, but their grand high society homes, the ones that still remained, were now owned by the fraternities and sororities of the town’s university. This one was no different, and Tanner could see a yellow glow creeping out of the windows around downed shades. He trudged up the steps and the freshmen flanking the doors looked at him.

“Who do you know here?”

“Are we really doing this,” Tanner sighed. “Veronica. And I know Paige.”

“Ah, we’re just fucking with you.” The freshman lazily punched his shoulder. “They only told us don’t let in anyone not wearing a tie. Have a good night bro.”

“Thanks, stay warm.” One of the doormen turned the knob and shoved the heavy door open. Tanner stepped into the warmth of the house. The lights were dim and it was packed tight. Students milled about in their finest clothes, suggesting a formal affair, but an EDM track boomed from deeper within the house. 

“Your coat?” a pledge said from behind him. He turned around and took it off. The pledge hustled up the steep staircase with it folded over his arm, running his hand along the thick wood banister as he went. Tanner scanned the swaying crowd for Veronica. He picked his way through groups in deep conversation, guys high fiving, girls with phones and keys and vapes and red solo cups in their clawlike grip. A guy he’d never seen before thrust a beer dripping with condensation into his hand and slapped him on the back as he went past. Tanner stopped in his tracks to crack it open. He focused his gaze over the rim of the can on the plunging neckline of a girl a few feet away from him, her soft tits squeezed together. His cock twitched in his cage. Can’t be doing that, he thought, and chugged down a second, then third sip of his beer. Veronica was nowhere in sight. He decided to check the kitchen. 

Holding his beer close to his chest as he weaved through the crowd, he stepped through the high doorway into the dimly lit kitchen. He saw a circle of three people, and instantly knew he was looking at the back of Veronica’s head. He stepped closer, taking in her outfit. The tantalizing shape of her tanned, toned shoulders and upper back were only broken by the vertical lines of two spaghetti straps. At her mid back began a deep dark dress, nearly black, but sparkling purple as his angle changed walking towards her. Her hair was neatly done half up and half down. In an instant, Tanner decided to be bold and plopped his hand down on her left shoulder as he broke into their circle. 

“Look who made it!” She said as her gaze came to rest on his face. “Tanner can follow directions!”

“Nice to see you too!” Tanner shot back, smiling. Veronica’s face was prettier than he had ever seen, whatever makeup she had put on for tonight perfectly defined her face. A thin twinkle of purple winked at the edge of each eyelid. 

“Paige and I were just talking about our test, but you already heard about all that! What’s new with you?” Veronica was nearly shouting over the din of the party.

“I don’t know, I just got here,” he said. It was quieter in the kitchen, but not by much. “Why the fancy clothes if we’re all just gonna party like we do every weekend?”

“Don’t you feel hotter all dressed up?” Paige interjected. “I certainly do!” She was in a pale baby blue dress that revealed every contour of her body the sweatshirt Tanner had seen her in at the library concealed. Her tits were pushed up high in her very flattering dress and her blonde hair cascaded over her shoulders. A massive tan hand at the end of a suit jacket sleeve extended toward him, and Tanner dapped it up purely on instinct.

“What’s up bro?”

“Yo.” Tanner looked up to the massive man on the other end of their greeting. “Don’t think we’ve met.”

“Andres. Nice to meet you bro.” He had a thick lisp, the end of his name coming out as a ‘th’. Paige was pressed hard against his side, even in the thick crowd it was obvious they were more than friends. The mop of curly black hair shifted as he tilted his head back to take a huge swig of his drink.

“Tanner.” He looked back to Andres and tried to shake the thought of how a naked Paige would look under his bulk. “What are you majoring in?”

“Don’t know yet. Just a freshman, yeah yeah, I know.” He flexed an arm and laughed to himself. He was nearly a head taller than Tanner. “But I’m on the football team. My parents don’t even know the rules!” Another hearty laugh, and Paige looked up at him and giggled.

“How’d you get on our team if you didn’t grow up playing?” Tanner was truly curious.

“Oh I got recruited, just as a goalkeeper. Scholarship and all. As a kid from outside Madrid, I always wanted to visit America. I applied to so many schools. And I got in here! It’s like a study abroad for me, as you guys say.”

“Goalkeeper, like soccer? Not football?”

“Well, when the football coach saw me he asked me to come over to their field after practice. He had their guy throw me a football, and what do you know, I catch it. Manos de oro! Coach wanted me to play for them, and brought me back to their locker room, introduced me to everyone, and explained what a tight end was.” Andres placed his massive paw on Tanner’s shoulder and leaned in. “The quarterback told me, ‘the girls don’t know the names of the soccer players.’” He winked as he returned to his spot in their tight cluster. “And that decided it! Now every Friday night I’m under the lights with the whole town watching! Crow Mountain CAW CAW!” he bellowed. His chant was returned, four ‘CAW CAW’s echoing back from around the party.

Tanner cringed at the football team’s stupid call and response and took another drink. Usually when the football team started making bird noises, it was time to leave the party. Two friends of Paige introduced themselves, and the topic changed. Almost imperceptibly, Veronica leaned in. “You liked my anklet, didn’t you?” just audible over the music and the din of conversation.

After a gulp, Tanner answered honestly. “I did.” He kept his eyes straight forward, nodding along to a conversation he had lost all interest in. “I was wondering where they were.”

“You know Paige already asked about it, right?” she whispered in his ear.

“No way.” He locked eyes with her and shivered, suddenly aware of the weight of the cage on his cock.

“Oh relax.” Her bright eyes were all Tanner could focus on. She punched him lightly, a drip from the beer in her hand sliding down the front of his suit. “I just told her it was another charm. She thought it was cute.” 

“Well don’t mess with me like that. You’re killing me.” A pause. “I mean, more than you already are.”

“What?” She pouted. “I thought you’d like it!” 

“I do. It’s hot. Let’s just, y’know,” Tanner looked out at the circle of strangers, “keep it between us.” 

“I just thought of something else we can keep between us,” Veronica said, eyes narrowing.

“Which is…?” Tanner felt the smile creep up his face.

“Oh just you wait. I’ve just been so busy studying I haven’t had any time to myself.”

A nervous glance confirmed everyone else in the circle was so occupied in conversation they hadn’t heard the words that made Tanner’s heart pace. 

“And what does that mean?”

Veronica shoved her hand into his. Her thin fingers laced between his own, and she squeezed hard. And with that, she was leading him back into the heart of the party, brushing aside dancing girls and drinking guys, threatening to pull his arm out of its socket, Tanner just along for the ride. When they reached the stairs, Tanner looked over his shoulder. Would anyone notice them heading upstairs? This wasn’t her house. Where was that pledge taking their coats? The butterflies got to him.

“Uh, where are we going?”

“Paige’s room!” Veronica shouted back.

“Your friend Paige? The one we just bailed on?”

“Wow, you figured that out on your own?” Veronica laughed at her own joke, dropped his hand, and took off. Tanner watched the muscles of her thigh flex through her tight dress as she bounded up the steps. At the top, she put a single finger to her lips and turned down the dark hall. One door was wide open to the room beyond, lights on and bed piled high with coats. Veronica went to the next door and slowly pushed it open. She leaned against the doorframe, took his hand, and with a smile pulled him inside.

Tanner’s hand instinctively swept up the wall adjacent to the door and flicked on the harsh overhead light. “Whoa!” Veronica shouted. “Way too bright!” She hustled over to the desk and flicked on a little lamp. “You can turn that off now.” The room seemed far smaller and more intimate illuminated by the bent over lamp.

“Why are we up here? Isn’t Paige gonna come up any minute?”

“Paige, as much as I love her, is head over heels for Andrethhh.” She dragged it out, exaggerating his lisp. “Nice guy, and jacked, but not all that. She’s basically been living in his dorm. Just look.” Her hand swept across the desk devoid of papers, then pointed to the too-perfectly made bed and empty hamper. She hopped up onto the bed, and her hair bounced around her neck and came to settle on her shoulders. “Now lock that door and get over here.”

The lock turned over with a satisfying click, as it should in an old building like this, and Tanner took a big swig from his beer. Placing it on Paige’s desk, he wiped his mouth with the back of his hand as he walked over to Veronica with authority. She grinned watching him get closer. He placed the webs of his thumbs in the crease between her hips and thighs and their foreheads touched. They reveled in the bliss of the quiet moment. Veronica brought her hands up to his cheeks and pulled him into a kiss. Her warm wet lips were as soft as the first time they had been together under the white light of that snowlashed window. Their tongues danced slowly at first, then as Veronica ran her hands through his hair and Tanner placed his around her lower back, they kissed with a passionate intensity. So passionate that Tanner could no longer ignore his cock growing rock hard in his cage, and pulled back to breathe.

“Aw, I bet I know what’s wrong,” Veronica teased, leaning back on her elbows. “Getting hard in that little cage?”

Tanner felt the blood rush to his cheeks. “Maybe.” 

“I think you are, don’t lie to me.” Veronica raised a foot and pressed it softly into his crotch. “Oh wow, I can totally feel it.”

“Yeah yeah. I can feel it too, believe me.”

“Aw, poor boy. So hard, and nothing you can do about it.” She pushed herself up off the bed and touched her forehead to his. “Nothing you can do about it, except with this.” His key dangled off her anklet in the light. “Do you want it?”

Tanner looked right into her eyes. Breathlessly, he answered. “Yes.” 

“Gonna have to do better than that.” She ran her fingers along the hem of her dress, and she shifted her hips side to side as she pulled it up along her legs. Inch by inch, her black lace panties appeared to Tanner. Without a word, he hooked his fingertips under the waistband and pulled them down, fast, along her thighs, over the bend in her knees, down her taut calves until she kicked them off emphatically from where they rested on her kitten heels. She smiled at him but he didn’t see it, eyes locked onto her glistening slit. He neatly pulled the straps down over her shoulders, slid the dress down until it bunched under her bust, and with a hand against her bare chest pushed her back onto the bed. 

The first lick between her warm folds erased the stale taste of beer from his mouth and he dove in, buoyed by her snatching breath. A few circles of her clit and Veronica had one hand in his hair pulling him in and another on his shoulder pushing him away. He brought his finger up between her spread legs and teased his middle finger against her before he gently slid it in. Curling it up against the roof of her opening, he tried to concentrate on the unique, soft, wet texture against his fingertip rather than the way his cock was threatening to snap the hard plastic enclosing it. He pulled his eyes up from the rippling, sparkling fabric directly in front of him, hoping to see the look on her face, but all he could see was the way her tits were heaving as her pleasure rapidly grew. Tanner stroked his finger in and out and mashed his tongue against the nub of her clit when all at once her soft thighs smashed into his face and she released her grip from the back of his head and instead grabbed the bedsheets. Her ankles locked into eachother behind his back, he couldn’t pull away, and her wet slit buckled up and down from his chin to his nose until, with a sigh, she relented. 

Tanner smiled, and stood up from the awkward position he had assumed against Paige’s too-high dorm bed. He rested his middle finger against Veronica’s lips, that finger still sopping with her juices, and, eyes still closed, she sucked it in. She smiled in perfect bliss. Tanner admired her, smiling at what he had accomplished and grimacing at his own predicament in equal measure. The thundering music from downstairs faded back into focus. “We should probably go,” Veronica sighed.

“I thought Paige wasn’t coming here.”

“I’d rather sleep in your bed tonight.”

“I’d like it if you did.”

Veronica pushed herself up off the bed, stumbled, and caught herself.

“I did good?” Tanner asked.

“You did very good,” Veronica answered, eyes blazing, and crossed her arms over herself to pull up the dress’s straps. She dove her hands, right after left, down into the neckline of her dress, adjusting her tits until they sat perfectly under the glistening fabric. “We can’t just leave that there,” she said, staring down to her panties resting on the hardwood floor. 

“Here,” Tanner said, taking them in his hands and holding them out open for her to step into.

“No, I’m not wearing those.” Tanner looked up at her quizzically. “They’re soaked. I was waiting for you all day, you know.” He wasn’t ready for that, and his cock throbbed once more in his cage. “Give them to me.” He balled them up and placed them in her outstretched hand. She took them, then closed her eyes and leaned into him for a kiss. Tanner closed his eyes, parted his lips slightly and leaned in.

His eyes snapped open when he tasted the fabric on his tongue. Veronica looked back at him with a teasing smile, pressing her panties against his chin and into his open mouth. “What?” Tanner opened his mouth to answer but she only pressed them in further. “I’m not wearing them out of here, so someone will have to take them. And that someone is you.” Her other hand lifted up from adjusting her dress to tousle his hair. He started to mumble, and she pulled them out.

“Fuck, Veronica.” He rolled his eyes. “Give me those.” She stuffed them into his hand. He held them up between himself and her. “Do you see how big these are?”

“Are you saying I wear granny panties?”

“No, I swear,” Tanner retreated.

“You should see how good my ass looks in those.”

“I didn’t really have the chance!”

“Maybe next time.”

“I mean if it were a thong, then maybe I could fit it in my mouth.”

“I think you should try, if you ever want to see your key again, that is!”

“Oh, so that’s how this is gonna go? You’re just gonna hold that over my head?”

“Do you want me to unlock you when we get back? I bet you were pretty hard in that cage when you made me cum! Do you even remember what cumming feels like?”

“Uh, yeah?”

“Spoke too soon. I mean it’s only been a couple days, but I was really hoping you’d forgotten. Guess I’ve gotta keep you locked up for a lot longer then.”

“Wait now, hang on.”

“Nope.” Veronica planted a kiss on his lips. “Are you gonna take those home for me or what?”

“Fine,” Tanner said, and, taking her panties from her hand, carefully folded them into his mouth. He could feel his cheeks bulging around them as the inside of his cheeks processed the lace fabric. A faint, familiar salty flavor registered on his tongue.

Veronica clicked off the light and took his hand to lead him out of the room. He ducked out of her grip into the coatroom, donned his jacket, and rejoined her at the top of the stairs. The music, softly thumping, seemed much less energetic than it had when he first entered the brownstone. Carefully breathing through his nose, mouth stuffed with her panties, Tanner surveyed the sparse students that remained at the party as he trudged down the stairs. Paige and Andres, the only people he knew, had vanished, thankfully. As Veronica pushed open the door, Tanner heard an unwelcome voice shout.

“VEEEEEE!” Paige shouted. “We thought we lost you!” Andres relinquished his grip on her shoulder as she launched to hug Veronica. “And Tanner! How areeeee you!” The drunk voice was grating, but he instinctively opened his mouth to answer her. Immediately, he gagged on the panties in his mouth, and his eyes bulged as his mouth snapped closed.

“He’s not feeling to well,” Veronica interjected, and, grabbing his shoulders, pushed him away from her. “I think he’s gonna yak.”

“Yak?” Andres asked.

“Throw up.” Paige answered patiently.

“Vomitar.” Andres laughed heartily. “Buenas noches!”

“Buenas noches!” Veronica answered for the two of them.

Tanner gagged, hard, and spat her panties out into his hands. They were coated in spit. Veronica tucked her arm around him. “You won’t get out of this that easily!” She gently placed her hand under his and pushed the wet bundle up towards his mouth.

“Seriously?”

“I thought you’d be happy to taste me,” she said, streetlight glinting in the purple makeup on the corner of her eyes. The snow was coming down slower now. One perfect flake glimmered, caught on her eyelid.

“I’d be happy to fuck you.”

“Then you should be happy to taste me.” Veronica took the panties out of his hands and gently crammed them into his mouth. “Shhhhh.”

Hand in hand, they walked back to his room.


r/ChastityStories • • 6d ago

M Chaste,F Keyholder My girlfriend cucks me with her uni bestie Samantha, the second night. [M25/ F25/F25 NSFW

117 Upvotes

Part 1

I was late getting out of work on the Second night of Samantha's stay, so I picked up take out on the way home. As soon as I opened the front door I could hear the sounds that I first heard last night, those sexual sounds Samantha had pulled out of my girlfriend Anna. I walked towards the moaning to find the pair of them in the kitchen.

The sight I was greeted with was my girlfriend naked between Samantha's legs, licking her pussy, all the while sliding up and down on a suction dildo that was stuck to the floor which had a pool of her juices collecting around the base of the dildo.

"Quiet slut," Samantha commanded and Anna's moans which filled the kitchen were gone. "Evening cuck, we got bored waiting for you, after we caught up," she pointed to the empty mugs and the half eaten packet of biscuits. So I got my slut to entertain me"

My eyes flicked down to Anna who was still licking Samantha's pussy as she slid up and down the dildo, just silently now. I cleared my throat, "I have take out," I said holding up the warm bag of food. "Great, we have left out your outfit for tonight on the bed in the spare bedroom, go get changed then we'll eat" Samantha told me in a tone that I knew not to protest about.

On the bed I found a pink silk camisole and matching french knickers. I stood and looked at them for the longest moment; had things really moved this fast? Could I call a stop to this? Could I refuse? Did I really want it to stop? Anna and I had done some crazy stuff together and ticked off a lot of our fantasies. But after the events of last night and despite any insecurities I had, there was no denying that last night had been a big turn on for me, I felt there was no other choice, so I got changed and went back to the kitchen.

Samantha and Anna were exactly where I had left them, the difference was there was a bigger pool of Anna's juices on the kitchen floor now. Dinner was a little surreal. I sat opposite Samantha and Anna separated by different pots of Thai food and rice.

Anna was naked except for a collar around her neck and she would only speak when Samantha asked her something directly, I had never seen Anna this submissive. Otherwise Samantha and I talked about our day, she talked about the different break out sessions she had attended and I talked about the project I was working on. All the while I wore this pink silk lingerie and Samantha's hand never left Anna's thigh like it was the most normal thing.

I suddenly got brave and asked Samantha a question that I needed to know the answer to, "Were you two this serious into this dynamic at University?" Samantha didn't answer straight away like she was considering how much she was going to disclose. Finally she answered, "It was mainly a bedroom Dom, sub thing, because we both lived in shared accommodation. But here it is different."

"What do you mean 'mainly'? And how is it different here?" Part of me didn't want to know the answers but my curiosity had gotten the better of me. Anna looked at Samantha and a slew of emotions crossed Anna's face for the briefest moment.

"Mainly, because we went to a couple of dungeons but otherwise it was just in each other's room, while we were at university," in a tone which was somewhere between nonchalant and dismissive. "As for here, (she paused) well it's just us three, there is no need to hide anything and keep it in the bedroom. Plus now I get two subs to play with," although she was stating facts there was a definite smirk to her tone.

Is that what I am to you, a sub? I ask.

"Well, you are more of a cuck, aren't you, but let me see how you perform and behave this week, and I will review your position before I leave." Samantha told me.

I felt myself blush as I felt a mixture of shame, embarrassment and arousal washing over my face and then my body followed. Samantha didn't say anything she didn't need to, her expression said everything, which said I already have the measure of you. Anna looked at me for the longest moment then she looked at Samantha as if she was asking permission to speak. Samantha nodded. "Ryan, I know this is a lot to take in but I think it will be good for both of us, I just ask for you to trust us, Cucky," Anna said before she slipped back into being Samantha's submissive slut.

"Cuck, clean this up then join us in the bedroom," Samantha gestured at the table. As I finished cleaning up I started to hear Anna's muffled moans coming from the bedroom and I hoped that I would be joining in tonight's fun as I walked towards the bedroom.

I entered the bedroom to find Anna gagged, blindfolded, her ankles separated and tied to the bottom of the bed and her wrists tied together. She was rocking back and forth on the same dildo as last night that was strapped to Samantha. Samantha just stood there and watched with great delight as Anna fucked herself on the dildo.

"Cuck, come kneel by my slut," Samantha instructed me. I knelt by Anna's feet, which gave me a good position to see and hear how wet she was.

"As I have the biggest cock in this apartment, it doesn't seem right that either of you should call me Mistress. Isn't that right slut?" Samantha said.

"Mmhhgghoo," said Anna which I took meant that she agreed.

"Good, from now on you both can call me Daddy," Samantha told us

"Geess Gagggee," Anna responded immediately.

"Well Cuck?" Enquired Samantha.

I was going to protest, going to say no but I could feel my cock straining against its cage as I knelt there by Anna's knees and that's when any defiance left my body, "Yes, Daddy."

"Good cuck," as the words left Samantha's mouth she began to brutally fuck Anna. It doesn't take many thrusts before Anna is begging through the gag. With practice ease, Samantha unbuckles the gag with one hand.

"Please Daddy can I cum?" Begs Anna as soon as the gag is out of her mouth.

"Yes, my slut," Samantha granted. Samantha didn't stop, she kept thrusting through Anna's orgasm, kept pounding until Anna's next orgasm had her begging Daddy for her next release.

Samantha looked down at me, when she saw the evidence of my submission and arousal, she ordered me up on to the bed and kneel in front of my girlfriend. As I got in position, I saw what Samantha had seen, that dark wet patch on the front of my french knickers. The evidence of my arousal, my body had shown Daddy how aroused I was as I leaked precum into the knickers.

"Slut look at your cuck, he is so aroused," Daddy gloated.

Anna raised her head and giggled. "Is my little walnut leaking because my Cucky loves to watch Daddy wreck her slut?" Anna teased me. I felt the guilt, the shame and submission twisted into a big knot inside me but what was even stronger was the arousal.

As the wet filthy sounds of Anna's pussy became louder and dirtier, I couldn't look away, I was paralysed by my own arousal. I just stared at her beautiful face as orgasm after orgasm crashed over her body. I saw so many different emotions cross her face, hunger, desperation, joy, pleasure, desire, lust, and even love for me but never guilt.

Just before her last orgasm Anna grabbed my caged cock and said, "Thank you so much for trusting me and for this week. I love you so much but Daddy's cock does things you never can." In that moment I felt the contradiction hit me hard, on the one hand the love between us was stronger but at the same time Samantha had wrecked Anna in ways I had never achieved.

Anna's last orgasm hit hard and it pulled me out of my head as she collapsed on to me. She clung to me like I was her rock and she needed me to ground her. Barely above a whisper she repeated thank you, I love you over and over.

Samantha untied Anna and between us we helped her up on to our bed. It was then Daddy turned her attention to me. "Clean Daddy's cock," she said as she positioned it in front of my face. Sucking cock had never been a fantasy of mine and honestly that huge dildo looked intimidating. But I had seen enough porn to give it my best shot at cleaning it, I kissed, licked and sucked the way I thought Daddy wanted to see. I managed to get half of it down my throat before gagging.

I had a new found respect for Anna how she had swallowed it so easily the night before and I think Samantha was impressed with my effort if not my technique. "Good cuck," she purred close to my ear. "You did such a good job, I have an extra treat for you." She looked in the direction of the kitchen and with a smirk she said, "That dildo is still on the floor, clean it with that tongue of yours and don't forget the floor. Then you can get some sleep in the spare bedroom."

As I knelt on the floor licking and sucking the dildo clean, voices, giggles, and moans started to come from our bedroom. From what I could make out Anna was now pleasing Samantha and it was her moans I could hear. As I cleaned up Anna's juices I started to think about the past two days, I realised I still hadn't seen Samantha orgasm and I had barely seen her in any type of intimate way and that made my cock strain against my cage. Although there hadn't been any talk about orgasm control or denial, I was starting to feel pretty pent up.

Which led me on to the question; where was the key to my cage, The last time I saw it was when Anna locked me up before Samantha's arrival, had Anna put it away somewhere safe? She wasn't wearing it, I could barely think about the other possibility, had she given it to Samantha? If that was the case would I ever be unlocked again? Would I ever get to cum again?

The past two days had surpassed any porn I had watched and I couldn't even imagine what the rest of the week had in store for the three of us.


r/ChastityStories • • 5d ago

M Chaste,F Keyholder Reviving the Dead Bedroom - Part 3 NSFW

52 Upvotes

I got out of the shower and dressed quickly hitting the road just before 7am. I drove back straight to the office and received a number of strange looks and comments about being back in the office after winning such a huge deal.  I just brushed it off saying a winners job is never done or some other winner cliche and went about my day. Even after everyone had left, I stayed for a bit too afraid to go home and be early. At 6:30 I packed up and made my way home. I rolled into the driveway with 5 minutes to spare and spent the extra time getting my wits about myself before I entered the unknown. 

7pm turned over on my car’s clock and I abruptly jumped out of my car and with a few quick steps made my way through the front door of the house. I entered a quiet house. I did a quick 360 trying to find the instructions that my wife had told me to follow.  As I spun on my heel trying to find out what I was to do to ensure no more further punishment, I finally saw a sealed envelope propped up on the third stair leading to the second story of our house. ‘Hubby’ was written on the outside of the envelope and I ripped it open now, wasting time to see what kind of night I was in for. Inside was a hand written note unmistakably from my wife. It read:

‘Dear hubby. 

By now I hope you understand what deep shit you find yourself in. You wrote the rules and couldn’t even live up to them on day 1 or 2. I read our contract over again and I think I will take one of the punishments you suggested. As you did not ask permission to consume alcohol, going forward regardless of how or where you cum, you will be required to consume every last drop of cum to my liking. If I say there is more to clean up, you will keep going until I am satisfied. 

As for your punishment for drinking in general, you are required to strip naked and make your way to the basement. There you will find a bench with four straps and cuffs, one strap for each leg. Line done on your chest and cuff your legs and one hand to the bench. Once secure, I will know and come down and complete the final strap. Do not dilly dally. You’re own the clock. Don’t make me madder than I already am, I don’t think you will like me mad.

Love, 

Your Keyholding Wife’

All I could do is strip as fast as I could, leaving my clothes in a pile at the front door and running down the stairs to my unfinished basement. As I turned on the lights, I found a single bench with with aforementioned straps and cuffs. I secured myself and not wanting to upset her, I tightened them as much as I could. By the time I was secured except for my last hand, I was completely immobilized except for my free hand. I put my head down and stared at the floor waiting for my wife to come punish me. I had no idea what i was in for but from the tone of her note, fear had taken over my senses. My caged cock dangled between my secured legs that were spread about a foot and half apart or the exact width of the bench I was now cuffed to. 

Suddenly from behind me I could hear the sound of high heels coming down the stairs. I tried to twist to see but clearly she had set everything up with precision to add to my fear factor. Suddenly I could feel her mount my back sitting on top of my back’s midsection like I was her pony. As I opened my mouth to ask what was about to happen she made quick work of shoving a ball gag in and securing it with a buckle behind my head. I giggled thinking she was being very mysterious while still being my wife and partner of 20 years. Obviously this was for show but before I could even blink, I blindfold completely blacked out my vision. I was suddenly mute and blind and as I tried to struggle my way out of the blindfold she jumped off me and secured my last free arm before walking around and tightening each appendage to the bench. 

She finally spoke, but not with her usual disinterested tone, but with confidence and mischief that I hadn’t heard since we were playful teens. “Not giggling now are we Mr. Well let me tell you how this is going to go tonight. You put me in quite a position the other night but I decided after signing the contract you wanted to go all in so guess what?!  You got your wish. I am still your loving, caring wife. But now I’ve spent the last few nights researching what it means to have a female led relationship and to be your Keyholding Dominant Wife.” She paused as she slowly walked around my naked cuffed body dragging a single fingertip along my cold skin as she did. 

“So throughout my research, there were two very key points that all the authors really laid on thick. 1) You are not in charge. You wanted this but whatever game you thought this would be, it is not YOUR game. It’s now mine and whatever your fantasy was, this isn’t that. This will be what I want it to be so that we can both get what we want out of it. You, not drinking and losing weight. And I get to find out how far you’re willing to go to please me and live out this fantasy. And 2) any infractions cannot go unpunished or corrected. Especially early on in the agreement. Direct infractions that go against either of our goals will not be acceptable and must be severely punished to reinforce and serve as a warning that further infractions will result in similar or even more severe consequences.”

I was now shaking. I wasn’t sure if it was because it was near freezing in our dark cold unfinished basement and I was stark naked or if I was shaking out of pure fear for what she might have in mind as a punishment. She continued “with all that said, after reading countless hours of examples of what a first infraction should be corrected with, I posted on a doms/keyholder forum a poll and I have selected the top two choices to be your punishment. So first up, because you drank 10 alcoholic beverages without permission, it is decided that you will receive 10 spanks per drink.” Pausing again, she circled me but now I felt a leather corp being dragged along my naked skin. “Today I went out and bought a few things. First was this riding corp and second was this wooden paddle!” She punctuated the sentence with the first of my 100 spanks. “One, ah ah ah!” She called out like the Count from Sesame Street. She was clearly having fun with this. 

“I hope you enjoyed those beverages because you’re going to be reliving the consequences of them every time you sit for the next week. One post said anything over 50 would leave you with serious bruising that you will want to avoid public changerooms.” She landed another hard spank with the paddle “Two!! So I signed you up for a gym membership yesterday and some personal training sessions next week with a cute little twenty something I met while I was filling out your membership application.” My ass was already burning red and I was starting to worry I wasn’t going to be able to make it. “But enough talk…if I want to really make this a memorable punishment I need to focus. I bet you would hate it if I lost count! So ready or not, here we go!”

She was mercilessly. She was not pulling her punches. She was letting me have it with all her might. At 25 I had tears pouring down my cheeks. At 50 I was a full on sobbing mess. At 75 she stopped and finally spoke to me again “Alright there subby?” All I could do was nod and hope she would just get it over with it “Well sweetie, I can tell by the colour of purple your ass has already changed, you’ve probably had enough.” I took a belaboured breath through my gag thinking her barrage was over. I was wrong. “But what kind of keyholder would I be? I couldn’t call myself a Dom if I didn’t fulfill the punishment I gave you. But I will give you a choice. I will continue spanking you to 100 or you can trade the last 25 for 5 hits with my hand to your balls.”

In my bubbling state I just started nodding. “I take it you want to stop the paddle and trade the 25 for 5 hits to your balls?” I started nodding furiously. “So be it. I want you to remember this moment. I want you to think about all your decisions that led to this moment. I want you to have this moment seated into your memory….that way we will never have to relive this. I want you to ask yourself, is breaking one of your promises worth all this?!” I was shaking my head no but the question was rhetorical. 

“Well, we will see in a few minutes if you made the right choice!” She said while I heard her fumbling around with something in a bag. Then suddenly she grabbed my balls and began tugging and maneuvering them between what felt like two planks. My head shot up “Oh you figured out what other toy I got today. This should help punctuate the lesson and ensure you never forget this important first lesson.” I felt it tight and locked behind my legs. “When the nice young woman at the story asked if I needed a humbler after I had picked up the paddle and crop and didn’t know what she was talking about. But when she explained it I knew it would come in handy. And now having you in it, I feel the name is very accurate. Just know, I have always wanted to punch a man in the balls without guilt and consequences, so I want to thank you so much for giving me this opportunity sweetheart. I would apologize for what I’m about to do, but you asked for this so I hope you enjoy it as much as I’m about to!” 

I tried to tell her to wait but all that came out was nibbles and she landed her first direct punch. I was instantly sent into another realm of existence. The pain shot through me and I couldn’t tell at this point if my balls or beaten ass hurt more. Again she didn’t hold back and landed a second punch. “Oh my God love. I think I just unlocked my own new kink. I’m going to ask to do this for every birthday or Christmas here on out. I don’t know how you’re liking it but I don’t know if I’ve ever had this much fun.” I groaned into the ball gag while my tears flowed constantly. Then two more in quick succession like she was in a TiBow class. “Ok lover one last punch and you’re all done with this part of your punishment. Thank you for this opportunity and trusting me to help you better yourself.” As she let one more fist fly she grunted as she made contact and finally I was done, completely throbbing in pain from the waste down. 

I could hear her walking around and stopped in front of me. “I’m sure you will never forget this experience and as we continue with your agreement, I want you to always remember this night. Again as I chatted with the lovely young lady at the novelty store she had one suggestion on how to finish the night that I would have never thought of in a million years. Before I release you she said I should just add one layer of humiliation to your punishment so when you reminisce about this night, your face burns as red as your ass does right now with the pure shame you are about to experience. Are you ready to wrap up this night subby?”

I slowly nodded just wanting the night to end and to go find some ice to sit on. “Well then,” she continued “Let’s get this over with!” Suddenly the blindfold was ripped off my eyes and I was greeted with a vision of a true Dominatrix. My wife had been transformed from an everyday soccer mom of sorts to a high end Vegas style Dom. She was wearing a latex corset with latex gloves that were fingerless and went all the way past her elbows. Scanning down I saw she had on a pair of black lace panties and then had knee high latex boots with a very high heel. I stared wondering how much she had spent and then cursing her for keeping this hidden all night. I’m sure it would have hurt more being spanked with my caged cock straining but it would have been worth it. “Ok, here goes nothing!” 

This was the first time she seemed unsure of herself all night. I could tell as I stared up at her from my confined vantage point that she clearly was forcing herself to do this as it was part of some master plan that she was now checking boxes. She had enjoyed spanking and beating my balls into next week, but now I felt some apprehension. Then she slowly moved her lace panties to the side and took a step closer to me. I could now see her perfectly trimmed landing strip that she hadn’t had in years. My cock began to push against the bars of my steel cage. And then without a word of warning she let go. Suddenly a stream of her warm yellow piss hit me directly in my face. The stream was strong and as she moved it all over my face, she hit both my eyes with enough force to open my eyes. It felt like diving into a chlorinated pool from a high dive but with a smell I wouldn’t ever forget. As she finished she unclipped my arms and the humbler before leaving and said “I’m sure you never had this on any list but now you know I am capable of everything and anything. I’m sure now every time you hear your own piss hit the toilet water, you will be brought back to this moment. I hope it has been burned into your memory. Now I need you to mop up and then go shower. We can talk about next steps in the morning.  And God help you if I come down here tomorrow and it still smells like this.” And with that she turned and left me alone to finish my chore. 

I don’t think this was the spark I was hoping to ignite in her when I made the proposal to lock me up, and even though I was going to have a hard time sitting for a bit I was still happy to have taken my shot. I just hoped I wasn’t going to have too many more of these correction sessions. 

To be continued…