r/Sissy • • 4h ago

Sissy Personals Notifications are such a turn on NSFW

21 Upvotes

Whenever I get that notification my heart just instantly flutters for a moment. The attention is intoxicating. Even if its just a comment from someone else like me or a request that might be seen as inappropriate 🫢. Those ones really my šŸ”’ straining. Was just wondering if anyone else felt the same way


r/Sissy • • 14m ago

Sissy Personals Looking to make new friends NSFW

• Upvotes

Hello my beautiful sisters how are yall today. Looking to meet new friends and have good conversation. Looking to.make new friends with the same interest as mine. Hope to hear from you soon


r/Sissy • • 4h ago

Sissy Story Sucked a huge BBC! NSFW

13 Upvotes

Met a guy on sniffies last night with the biggest cock I've personally seen so far. Id say at least 8.5 in and girthy, it got me so horny just looking at it lol. Anyway, he comes to my apt I start slow licking the under side of his cock ,stroking it while sucking his balls, just getting everything nice and wet. He then tells me to get on the bed and lie on my back and he omg he starts to fuck my throat while stroking my dick. He stretches my throat out for probably 10 minutes, pulls out and cums on my face and i suck the head for anything left and it tasted so good!. But I cannot tell you how submissive and turned on it made me feel. Definitely ready for another one


r/Sissy • • 8h ago

Sissy Story Hubby urgently told me she needs to doll up Sunday morning because she "accidentally" made plans for the evening. NSFW

20 Upvotes

I was cleaning the kitchen after breakfast this morning when she came down in a rush and told me she needs help with her makeup before noon. Well turns out she was texting one of her daddies and agreed to let him fuck her without even thinking.

Well, he was going to be picking her up in the early afternoon and they would go to their usual motel to fuck, it only gave us like 3 hours top to prepare. Told her to go shave and prep herself and by this time I prepared the makeup.

We didn't focus on the lingerie because we knew his only plans was to get his cock inside her. A cotton panties and bra set did the trick and on top a blue dress. Her nails were done last week so they were good and we went with simple earrings (yess she got her ear lobe pierced now). I did her hair and her makeup last, simple foundation, blush and red lips. Coco Chanel as perfume. She tells me this makes her feel like a whore wearing it.

Locktober obliges, she's been caged for a while already but I swapped it for her pink one as it was smaller and cuter. Also specially gave her the key incase her daddy wanted to suck her.

We set out at around 12:30 to meet her daddy at a McDonald's parking lot. It was surprisingly desert and she swapped cars heading to her date.

He had her back at our place by 5 pm and she came home exhausted. Hair was a mess but she looked very satisfied. I literally could still see his cum on her hair jfc, and a massive hickey was also present. Had her shower and she helped me prepare dinner.

Kinda envy her Sunday plans lol. I was just busy working all weekend.


r/Sissy • • 1h ago

Discussion In which communities do you think there's the most Sissies in it? NSFW

• Upvotes

Outside our communities, which are the obvious ones of course haha


r/Sissy • • 5h ago

Need Help / Advice NEED ADVICE. Very on an off motivation to become a sissy (I didn’t realise it was this long 😭) NSFW

9 Upvotes

This is more of a rant / vent than anything but I’d absolutely love for any comments or advice from anyone 🫶🫶🫶

So I’ve been following sissy porn for a year or two now, I used to find it rlly hot but never really considered myself as being the sissy I just always found it really hot (saying it because ofc I found the sissies hot but it was also sth about the situation and it’s rlly hard to explain)

Anyways recently I’ve started to get a bunch of urges after watching sissy porn for that long, so I eventually bought lube, grabbed one of my mums thongs and went to have a loooong shower. During the shower I shaved my clitty, my ass, and my chest and back, however I did not shave any parts which would normally be exposed during an everyday basis.

The reason I didn’t shave is because my parents are really old fashioned and religious (not throwing any shade at religious people, in fact I am also extremely religious which is why this was such an odd feeling for me) and would criticise me if they even saw me shaving my legs or arms.

Anyways after I shaved I put on a latex glove and put some lube on my fingers and got to fingering. It was really painful at first however it got really enjoyable towards the end, despite it not really making me feel like I wanna cum. After I stopped, I got up and just normally jerked off in which I had a really nice orgasm.

HOWEVER, after I came, post nut clarity set in (as I’m sure it happens to many) and my thoughts started spiralling everywhere. ā€œWhat am I doing right nowā€, ā€œI shouldn’t be doing this at allā€ (mostly because of my religion which I don’t wanna make this a thing based on js religion but if you really wanna know about it I can explain 🫶) and even like ā€œwow I’m such a failure what am I doing with my lifeā€ (obviously no offence to any sissies, it was just a very confusing period

Lately my urges have been getting a lot more after a period of not wanting to do anything. They got to the point where I just couldn’t handle it anymore and I impulsively bought a dildo and butt plug off of an online store, as well as a cage and other sissy clothes from temu. Due to my strict parents (esp my mum which loves to organise everything in the house even my room without notifying anyone) you could imagine how scared I was doing it. But I ordered them to arrive in a parcel locker and not to my home just in case. The toys will be here in approximately three days while the temu clothes will still take a while

I think the point of this whole rant (and if you’ve gotten all the way here god bless your soul 😭🫶) is that I love the feeling of being a sissy it gets me really hard and turned on and I’ve even imagined myself getting fucked by big cocks recently despite homosexuality being a very discouraged part in my upbringing, but every now and then I get this feeling where I regret doing anything to do with being a sissy and I regret buying the toys/clothes.

Is there any way to get over this? Am I just being way too problematic? Does anyone have any advice especially about that feeling to urself where you’re ā€˜disgusted’ or not convinced that what you’re doing is okay because it goes against what you’ve been brought up to believe?

Anyways thank you for reading my super duper long rant about this stupid topic haha 😭

I love all of you I hope you all have the best day ever 🫶🫶🫶


r/Sissy • • 1d ago

Sissy Story Dressing for the maintenance man. Update: I did it! NSFW

266 Upvotes

As an update to my last post, I ended up wearing my leggings for the maintenance appointment!

I'll make a post with pictures so you all can see the look, but I ultimately decided on wearing a black sweatshirt, black leggings, and white socks over the leggings :)

I was so nervous going into it so I decided to just get dressed early on in the day to avoid backing out. The appointment window was from 12-4, but it kept getting delayed and delayed, which meant I just had to sit there with my anxiety for longer and longer lol.

Finally, close to 7 pm I got a text saying they would be arriving shortly. I looked in the mirror to make any final adjustments and as I was doing that I heard a knock on my door. I knew I had to just go for it without giving myself a chance to back out so I went for it. I opened the door and greeted the maintenance worker who was nice and professional. My front door is on the first floor and my unit is on the second, so I walked up the stairs in front of him which definitely gave him the opportunity to catch the view lol. I could tell he was making glances at my legs, but he stayed very polite and professional which honestly put me at ease.

I stood in the bathroom with him explaining the situation and he got to work. I sat in the living room right next to the bathroom where he could see me every time he was going to his tool bag. He called me over a few times to explain things, but also a few times just to talk casually too and make conversation. He fixed the issue (yay) and we chatted for a few minutes standing in the living room. He went on his way and I ended up feeling very relieved.

I'm sure some of you were hoping this would be a story where I wind up on my knees or something, sadly for those of you this is a wholesome story where I was able to express some femininity and be treated totally normal. I really respect him for being so professional and chill, and actually making conversation as well. I got to feel pretty without being judged and that alone was great. I'm definitely tempted to go out today wearing that same outfit since it felt so freeing yesterday.

So all in all, I hope this story is some encouragement for any others like me who want to do something similar but may be too nervous! I feel like so many posts and comments on here are way off in sissy fantasyland that I think it's good to share the down to Earth stories as well :)


r/Sissy • • 9h ago

Sissy Achievement! I finally went to the gym plugged! NSFW

15 Upvotes

Finishing up my workout rn but I’m so excited I finally got the courage to wear it here! For backstory I’ve been playing with plugs for about a year and just recently got a dildo but I never wore a plug in public.
Up until today! My head feels all fuzzy idk if it’s from a good workout or my ass being so stimulated.
I decided to wear my biggest plug cuz go big or go home yknow, and it makes me feel so full and I can feel it shifting everytime I sit down I love it.
Definitely will be doing this again soon! And the cherry on top… like 5 mins into being here I run into an old friend and we were catching up while he had no idea I was plugged and in panties under my boy clothes


r/Sissy • • 6h ago

Question Are there any site for video/streaming my body? NSFW

7 Upvotes

I just love the feeling, not for money or anything


r/Sissy • • 37m ago

New Sissy Hi cuties šŸ’‹ NSFW

• Upvotes

Finally decided to jump head first into my sissy journey. I’ve been dressing and doing stuff online for a while now but I think it is time to finally embrace it head on. I love dressing but have never done anything in public or had sex as a sissy. I’ve also never been with a male before. My partner is unaware as well. So all this to say any encouragement or advice is much appreciated. I am also open to friendships or chats about anything and everything.

Love,
Kendra šŸ’‹


r/Sissy • • 11h ago

Sissy Story Solo travel sissy time NSFW

14 Upvotes

Hi all! I live in a very conservative place and I don't live alone so it's rare I get to go out and be Alexi. I had some time to travel recently and while I was between cities I really wanted to let her out and have some fun.

I started off in my first place visiting friends and family, so I couldn't do much then, but I had a significant drive on to my next destination so I decided to split it up into 2 days and stay overnight in an in-between city.

When I first arrived at my motel I settled in and got unpacked, then shaved everywhere, cleaned out my ass, showered up and started to get dressed up.

I put on super comfy pink panties (purple depending on who you ask), a bra with B cup breast forms, thigh high pure black stockings, a choker around my neck, and clip on earrings. I did my hair, which is already quite long so I tidied it up and put some nice curls in it. And to top it all off I put on a super short sleeveless minidress that barely covers past my ass and crazy high heels. I'm talking around 7 inch heels that are oh so hard to walk in. I took everything out of my wallet and put it in a small black purse I had.

It wasn't quite dead of night yet but it was already starting to darken by the time I was all ready, which was fine by me because it was hot af out. Nice weather, not so great to crossdress in. Anyway,I had forgotten a few things at home so the first stop I went to was a sex shop right on the main street. I had to parallel park on the main street which I'm almost always nervous about, even more so since I was dressed up and felt like everyone was staring, but I finally did it and got out of my car. I had to walk past a few shops first but made it into the sex shop. I asked the person at the counter for a specific type of butt plug and chastity, and while they didn't have any good cages the plug selection was great and she was incredibly helpful.

Next I drove to Walmart. In the parking lot I lubed up my plug and put it inside me. I was still parked pretty far away from everyone else but doing that in my car still felt crazy nerve wracking! I wanted to go in and get some shopping done but ended up chickening out, so I went to get gas instead. I pulled up and started gassing up my car, and the slight breeze kept lifting my dress up which felt amazing in the heat but I think my nervousness was making me get even more hot. It wasn't empty and there were quite a few guys also getting gas at the same time. After I finished I needed to clean my windows so I'm sure they enjoyed the show.

Next up, I went to an adult video store that had a narrow path to park in the back. I parked and went in, looked around the front store area for a little while but also chickened out going further back so I decided to walk back to my car and go back. When I was walking through that narrow path a car was trying to pull in behind me but they weren't passing me so being the slut I am I "accidentally" had my purse catch on my dress and hike it up showing them my panties. I thought this would be super hot but I turned around and it was a fucking cop car, so I pulled my dress down really quick and stood off to the side so they could pass. Both cops were staring at me as they went in, did a loop in the parking lot and then left. A few guys were also hanging out in the lot, they smiled and waved and I gave them a little smile and wave back but that was it.

I got back to my room and relaxed for a little while, downloaded Grindr and wanted to see what was out there. I was messaging with one guy who wanted me to come by his apartments nearby, so I put my heels back on and walked the block to his place, only to have him ghost me which absolutely sucked. So I walked all the way back to my room, passing a few other people also out late. I ended up messaging one guy who wanted a handjob so I invited him over. He was super fun; he started immediately feeling me up and we got straight to it. He sat down, pulled his pants down and told me to kneel and get to work. And so I did! I put some lube on my hands and started jerking him off slowly, until we finally ended up with him on the floor and me straddling him, still jerking him off until he came. After that we took all sorts of pictures together and he got to feel up my ass. It was pretty tame, but overall a fun time. I ended up messaging another one who came over pretty quick, I jerked him off for about 2 minutes then he came and immediately left.

It was about 2 or 3 am at this point so I cleaned up, fucked my ass with my plug for a little but and then also came pretty soon after touching myself. I don't think I did anything too crazy but still it's the most sissy thing I've done and I'm very much looking forward to doing more next time I get the chance!


r/Sissy • • 16h ago

Need Help / Advice Wife wants to buy me clothes but we got a problem. NSFW

32 Upvotes

After opening up to my wife some time ago she agreed on going shopping with me to buy me stuff so in stores so it won't get too awkward. I am really happy about it and we almost did it but we had a problem. She is not dom, has no dom intentions and especially no idea about humiliation.

She accepts this side of me and tries to support me. But once she asked me what stuff i would like to get i told her she can choose anything she wants to see on me as long as she thinks it will humiliate me. At that point her eyes went full blue screen mode.

She still wants to help me out but she has no idea what to do and i have no idea how to explain.

Maybe i should give her some examples?

But then again, it feels very strange to explain somebody how to humiliate me (even if she's my wife). Also i think i would be more ashamed of showing her some examples then from putting on what ever she would choose for me to wear.


r/Sissy • • 1h ago

Need Help / Advice Chicago bars NSFW

• Upvotes

Me and the lady have been wanting to get all dolled up and hit some bars in the city. Best crossdresser friendly bars in Chicago or surrounding areas?


r/Sissy • • 4h ago

Need Help / Advice I want her to be a part of it NSFW

3 Upvotes

Hello, šŸ¤—

I love being feminine, feeling it, embracing it. The thought of it alone turns me on and gets hot and fired up. You know even just the slightest thought of serving someone or something like that.

I love wearing panties and stuff.

But I have to do it all in secret being a husband to a lady from a traditional background and us being poles apart in literally everything.

I'd love for her to be a part of it. Like you know have me wearing panties and dress me up,

Like I'd love to have a marriage where she can be He and I can be she, where we can share the excitement of buying new panties, outfits, toys etc. have all sorts of fun play etc.

How do I, well I don't even know how to say it, but like how do I get her into it. I'd love for her to be part of it in a way that she loves it and craves it too. Is there a way to like maybe start chatting about it on text and like how. (Prefer text honestly)

I'll appreciate your thoughts and advise.

Thank you.

Have a great afternoon

ā¤ļø


r/Sissy • • 10h ago

Discussion It's Sunday Night Ladies lets hear your confessions from this week. NSFW

8 Upvotes

Well I'll start this off I have been edging my wife by refusing to breed her this week as she's not in her fertile window (we are actively trying for another kid). She wants it bad and keeps playing with her pussy begging me but I've been refusing. Anyways I decided to go out on thursday and get my cock throated by some slut in the local glory hole after a pretty good blow, she knocked before I came. They asked me to come into their booth, I entered to find this youngish chubby femboy pawing at my crotch. I wrapped my dick and pulled down her shorts revealing her black lace panties I rubbed my cock on her crack for a good bit teasing her. Needles to say we fucked I called her a good slut and left her to suck more cock before going home.

Edit: fixed a few pronouns and punctuation.


r/Sissy • • 1d ago

Sissy Story Got pumped and dumped last night and I kind of liked it NSFW

130 Upvotes

Hi girlies!

Last night I was on Grindr late, just browsing and seeing what’s out there. I wasn’t even dressed up, but I was kind of hoping someone could convince me to.

After a bit I got a message from a guy that piqued my interest. He said he was straight but a long dry spell was making him curious about having sex with a sissy. We started talking and he said all the right things, so I told him if he could wait an hour or so for me to get ready I could help him with his curiosity. He agreed and said he was ready any time and could come over whenever I was wanted.

I started getting into girl mode and sent him my address and buzzer code when I was almost ready. He replied and said that he lived nearby and wouldn’t be too long. While waiting I was half expecting him to ghost as ā€˜curious’ guys tend to, but about 20 minutes later I got the buzzer notification on my phone. I took a second to verify that it was the right guy (my building has a camera in the buzzer you can look at, great amenity for people who like hookups!), it was, so I let him in the building and waited until he made his way up and knocked on my door.

I opened the door and led him to my bedroom. I was wearing a simple bra and panty set underneath a lacy lingerie robe. We made a bit of small talk while I sat him down on the bed. I told him to get comfortable as I let my robe drop to the floor. In a flash his pants were off and I was on my knees giving him a blowjob. His dick wasn’t huge or anything but it looked nice and he was very clean and hygienic.

After a bit I asked if he still wanted to have sex and he enthusiastically said yes. I got a condom from my bedside table and told him to put it on while I got my hole lubed for him. I rode him reverse cowgirl on the side of the bed for a bit, then we both got on the bed and switched to doggy. He gave me a good pounding and finished in the condom. I didn’t cum but I rarely do my first time with a guy.

He got cleaned up in the bathroom, thanked me, and left. I went to message him again this morning and saw that he deleted his account. Maybe he’ll be back, but either way I’m not torn up about it. I find it kind of hot that he just needed me for one night of relief. I also kind of like that there’s a guy out there whose only memory of me is my ass bouncing on his cock. I’m realizing now as I write this that we don’t even know each others names, and it’s making me horny all over again šŸ™ƒ

Anyway, just wanted to share! Hopefully you can enjoy or relate.


r/Sissy • • 3h ago

Discussion I need help finding a good all day sex toy NSFW

2 Upvotes

So hunting season is in full swing I am looking for toys. what will be good for me to get? It’s got a last all day too.
That won’t make too much noise.

Mind you it’s getting colder by me and I will have to start to layer up


r/Sissy • • 11h ago

Sissy Story Losing the key NSFW

7 Upvotes

Hello girlies! Little story time. I got all dressed up tonight and was really feeling myself so I went to my backyard and tossed my key out there all dressed up and locked in chastity. Also little side note but that was my first time going outside all dressed up! After I had my fun I went back out to try to find it and I can’t! Guess I’ll either have to stay locked for the night and find it in the morning or use my spare to unlock myself then lock myself back up and look for it in the morning. What do yall think I should do? Just to be clear I’ve got a backup key so I’m in no trouble but I am a little worried about what I might do the next time I dress up. Anyways thanks!


r/Sissy • • 10h ago

Need Help / Advice Curious bout it NSFW

6 Upvotes

So I have been edging myself since like almost a week now and I was thinking about some fun and pleasurable ways to cum but can't seem to find anything to my match.

Can y'all suggest some ways like ass play, nipple play blah blah. My boyfriend can't seem to make me cum handsfree till now.


r/Sissy • • 6h ago

Question Conflicted perspective towards CNC NSFW

2 Upvotes

Tw: SA, Nymphomania

Not sure if this would be the right place to post this, but my daddy/hubby advised me to post on here to get abit more perspective.

So first things first, when i was a preteen, i was SAed awake repeatedly by a male relative many mornings till i became a teen. It was quite traumatic and it definitely was a contributing factor to what lead me down this lifestyle, which I assume it was some sort of coping mechanism for me. I dont have much problems with it nowadays as i am in a stable wholesome relationship with my daddy/hubby.

Recently, hubby had been assigned to onboard the overseas team via online zoom calls. Meaning that he will he awake much earlier than i would normally wake up. Normally i would be the one to wake up first to make him breakfast and wake him up with either head or sex. But since he will be up before i am, i gave him permission to have sex with me while i was still asleep as long as i was wearing the pink buttplug (cleaned out the night before). Theoretically, i was already free use before this point, but free use is not really evident when im the one that is more intimate than hubby. So this was the first time he will actually be using the free use card. I honestly thought nothing of it.

So i was indeed quite surprised to wake up the next morning at 4am with my legs over my head and tied to the headboard and my hubby balls deep in me. My initial reaction was actually abject horror and i experienced a momentary terror. But as the wakefulness crept back into me and i made more sense of the situation, seeing my hubby there, giving me cheek kisses and patting my head, seems to place a kind of peace into me. This feeling only seemed to grow as i started to experience the pleasure of his thrusts into me.

But this situation, combined with the pleasure i started to feel, seemed to remind me of the same pleasure i used to feel when my aggressor was SAing me (yes i did eventually learn to feel pleasure from being SAed, i think its another coping mechanism). I felt a tinge of disgust towards myself, but that didn't last long and was soon replaced by a feeling i can only describe as "Victory"? The feeling was a mixture of pride and triumph that i cant really explain where it comes from. I just felt weirdly very happy and empowered in that moment, i just smiled and gave him a kiss and said "good morning"

Me: Why are my legs tired up?

Hubby: It was hard to keep them away while you were asleep, are they bothering you or making you uncomfortable my love? If they are, im sorry and i wont do it again. I had my reservations about doing this at all.

Me: No its alright. Its strangely kind of very hot. Im not sure why.

Hubby: Im glad, my meeting will start soon, may i finish inside you?

Me(smiling): Please *don't ever* ask me for permission to put your babies in me, i exist to carry your children, and you needing my consent or permission is silly.

(Both hubby and I *LOVE* baby making talk)

Hubby(confused smile): why the sudden focus on consent? Regardless, i think it polite to ask for consent even from my spouse.

Me(slightly annoyed): i dont want you to.

Hubby(Understanding smile): Im cumming inside you.

This feeling of "Victory" got really intense as he came inside me. I have always felt proud as a wifey to carry my hubby's cum inside me all day. But this was different, i felt triumphant, like i won over someone, felt cocky even. My hubby went for his call after that and i went back to sleep after plugging myself back up.

(I had several chats with hubby recently so ill try my best to explain my perspective as to how i think i got this feeling/idea).

When i was getting SAed, my aggressor never finished inside, he always wore a condom and pulled out when finishing, he has mentioned many times about how he wanted to finish inside me, but never did. I assume it was because it would have left more evidence if he ever got caught. So he never did so, inspite of repeatedly stating how much he wanted to. So when i made the decision to allow my hubby to penetrate me and finish inside regardless of my consent, it sort of felt like i was sticking it to that man like:

"Look at you, having to force me, coerce me, pressure me, beg me and lie to me just so you can SA me and get away with it.

And here i am, willingly giving up my dignity, my safety and my autonomy to this man, giving him blanket permission to SA me *and* finish inside me *and* i will still happily carry it around with me all day. Compared to him you were pathetic"

Its weird, but im not sure how else i can put it. Its sort of like, getting SAed by someone i love and trust, on my terms, was somehow making that other man pathetic, like i was cucking him, like: "look what i am doing for this man that you always wanted but will never get".

I hope that makes sense?

Now this is great and all, but like, after that point, i just craved more and more of that feeling. I kept egging my hubby for more and more "realistic" roleplay. He was happy to oblige at first, but i guess i got more and more explicit in my expectations that he is now slightly concerned that this might not actually be healthy for me mentally.

And honestly, now that he mentioned it, im not too sure myself. So what i sorta want to ask is; is this alright? Is this healthy? Do i need to go back to a therapist? As of this moment i do feel safe, secure and happy. But could i be making things worse for myself in the long run? What are your thoughts?

*Do let me know if there are any parts that are confusing! This was edited many times in an attempt to make it easier to read (this is draft 3 already). So please let me know if i got confusing at any point. Or if you have anything you want to clarify or ask as well!*


r/Sissy • • 10h ago

Discussion What sexy lingerie outfits do you have or what ideas do you have in mind for such? NSFW

5 Upvotes

Having a nice lingerie set that feels quality and looks sexy really elevates the experience. Although I do have some options currently, I’m always obsessing over new ideas, something to make me feel sexier than what I already have. Outside of being a sissy, I do like having a nice suit and honestly I’ve always liked the idea of having nice lingerie underneath to complement a nice suit. What does everyone’s favorite lingerie set consist of or what would you ideally want? I want to hear some ideas.


r/Sissy • • 19h ago

Sissy Achievement! First experience with another guy at kink event! NSFW

21 Upvotes

Yesterday I went to my first ever kink event for Locktober, it was amazing! I was unsure about going but I’m so glad I did. At first I was pretty nervous and anxious but I quickly felt more comfortable as people came up to say hi and were super approachable.

I got complimented and called cute by a few different guys. I was afraid my outfit wasn’t attractive but having tops and bottoms compliment was insanely hot.

Last night was also my first playing and kissing with another guy!!! He was also in chastity and was soooo cute. After we first talked he said ā€œI hope I see you laterā€ and my heart was racing from excitement.

When we met up later on we talked for a bit before he started playing with my balls, a first for me. Then after feeling his for a bit he asked if he could kiss me and without second thought I said ā€œOf course.ā€ It only lasted for a minute or two but making out with eachother while feeling each others cages and balls was an experience I will never forget. I wish I saw him again that night so I could’ve kissed his balls and cage:(.

I’m so glad I ending up going to this event, it’s given me so much more confidence in myself. I think this was the push I need to finally have the courage to meet up with someone!!!

Also shoutout KINK3D, they have the best cages and peopleā¤ļø


r/Sissy • • 10h ago

Question Can wearing a chastity cage cause trouble getting hard afterward??? NSFW

3 Upvotes

I’m a little worried and wanted to ask those with more experience. 🄺

I wore my chastity cage for about a week, and now that I’ve taken it off, I’m having trouble getting hard again.

Has anyone else experienced this after wearing a cage? Did things go back to normal for you? How long did it take?

I’m a little nervous, so any advice or personal experiences would be appreciated. šŸ’—


r/Sissy • • 8h ago

Need Help / Advice First time breeding booked... advice from those who've been there. NSFW

2 Upvotes

The short story:
TLDR; Sissy with a lot of toys/solo experience has a confirmed dom willing to breed next month, need advice ITO expectations of the experience vs my ref point of (fairly big) toy play.

The (w)hole story:
I've been a closet sissy for a looong time and not to brag but I'm pretty experienced with large toys, chastity etc. I've been on the fence ITO finding a human to consummate my sissyhood but it seems like I have a guy who's keen to commit to a fairly faceless breeding session (likely more of a pump and dump, waiting doggy style on a bed etc than a long drawn out session).
For those of you who've done/do this I'm wanting to know what to expect. The physical size doesn't stress me out as I think I've taken bigger than the average cock regularly but I appreciate none of my toys have ever been attached to another human being.
My plan so far is to have a really good clean prep and probably play with something small before he arrives but then again I don't want to be too loose? Is that even a thing? Has anyone reacted badly to their first cock? Will I even be 'satisfied'?

Any first hand advice or tips would be great TIA.


r/Sissy • • 22h ago

Need Help / Advice What's the best audio hypnosis to achieve a no hands orgasm ? NSFW

22 Upvotes

I have listened to some of shibbydex audios in the past and have gone quite close to cumming certain times where I had to pinch my nipples to make myself cum to take the cummies Outta my tip Would be glad if you cuties can share some other options or stuff you listened to achieve a orgasm in audio to concentrate further and help this premature ejaculator squirt