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 :)

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 ‘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 🙃

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

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.

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 “I hope I see you later” 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 “Of course.” 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 people❤️

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

This might be a bit longer so I have provided TLDR at the end.

So I have been crossdressing since I was a child and my dream was always to go out fully dressed in public. I have done this partially like wearing lingerie underneath my boy clothes, or just wearing women's jeans - but that's about it. A few months back I connected with a CD from reddit and after chatting for sometime we decided to meet in person. Now she has gone out in public fully dressed multiple time before and I wanted to do this too.

So on the day, we decided to meet at a cockbar bar in the evening. And for the full day I decided to feminize myself. I shaved my whole body (including my clitty and boi pussy), applied scented moisturizer and did my makeup. The makeup took like sooo long, almost an hour. I'm a total amateur and wasn't too happy with the result but I went ahead anyway. Then I tucked my clitty and wore the tightest tiniest panty that I have to keep my clitty in place. Wore hip enhancing panties that gave my butt a juicy shape and women's skinny jeans. For boobs I have B cups stick on silicon breast that I used and then wore a black padded bra and finally a full sleeve black top. Finally I wore a wig with shoulder length hair and tied that into a ponytail. My look was completed and overall I looked quite feminine. Hehe. Oh also I painted my toes and wore a pair of high heels.

I called a cab and went to her hotel and was waiting outside on the footpath. And that was the mosttttt humiliation I have ever felt. There was an alcohol shop nearby and all the guys were just staring at me and I just couldn't take it. I was keeping my head down and staring at my phone the whole time and texting her to quickly come. After about 10 mins of excruciating nervousness and humiliation she finally arrived. And oh man. She was stunning. She was wearing flaired jeans, a red crop top and red hot lipstick. Sooo hottt. I was so glad she came cuz I just couldn't take the stares from the guys any longer. We quickly booked another cab and went to the cocktail bar.

Over there, the waitresses were all smiling looking at both of us. I don't know what they were thinking but they remained professional throughout. Inside the atmosphere was dimly lit and the crowd wasn't so much but I was still nervous. We ordered our drinks and once I had a few I started to feel relaxed and finally started enjoying. I even shifted to her side of the table and was laying my head on her chest while talking to her. It was like we both were two girly besties just enjoying a nice evening. I was crossing my legs like a girl, taking smaller sips and overall my mannerism was very feminine.

We spent like 2-3 hours there and finally decided to leave. I dropped her off at her hotel and went back to my house. Overall the whole experience was so so so good. This was like a dream for me to go out as a girl and I did finally. The beginning part was full of nervousness and stressful, but the ending was full of enjoyment, satisfaction and happiness. So yeah this was my sissy achievement. I know other's over here have done so much more, but for me this was a very big step that I conquered.

TLDR

Went out fully dressed as a girl for the first time and met with another CD at a cocktail bar. At first I was really nervous and anxious but later I started to feel relaxed and enjoyed the experience.

Heyy girlies! For some background info, I got my first cage as of the end of September. I hadn't had it long enough to be able to wear it comfortably for the entirety of locktober, but I'm trying to wear it as much as I can. A couple weeks ago, very early on, I got realllly turned on listening to some erotic audio while scrolling my Reddit feed and chatting with someone, and I tried adjusting my cage, which somehow only turned me on more. After a couple minutes, I started basically jiggling my cage back and forth with two fingers by pinching the spot where the lock is, and it got me really hard in my cage. Finally, after only a couple minutes, I splurted out a caged orgasm for the first time.

I want to know if you've done anything like this before? Do you think it was naughty of me to cum this way?

Leading on from my recent post, and as much as I wish otherwise, receiving anal is likely something I’ll never manage. From the group’s experience of men who enjoy sissies, would they be okay with a sissy who is oral only? Although it’s been a while, I love sucking cock and using my mouth to give pleasure wherever I’m told. Or, am I likely to be constantly under pressure to be fucked?

I need some sissy education hehe

Instead of talking about what you sissies want in a Dom, I thought it would be fun to hear which fictional characters you think would make a great Dom, Soft Dom, etc., and why. What would you imagine being with them would be like?

P.S.
For those curious, I actually try to channel a little Deadpool, Rocket Raccoon, Peter Quill (Star-Lord), and Loki (after the first Thor movie) in my approach to being a Soft Dom, rather than Homelander, Voldemort, or King Joffrey.

Reversed the classic NSFW Straight Relationship into having the Woman being the Alpha Male role and the Man being her Sissy Slut as a relationship for me sounds incredible for me, it's my goal kinda

My girlfriend is aware of my crossdressing kink, but we’ve never explored it together. We want to go into it slowly, and start with underwear. What type would people recommend for the first time? I have a decent collection, but am unsure what is too much/too little

I consider myself straight, but I’ve developed a strong sissy/crossdressing kink, especially the humiliation side of it. The biggest rush comes from imagining being seen by strangers and knowing they might judge me.

I keep going through the same cycle: I get intense urges, buy sissy clothes and chastity gear, feel excited, then get hit with guilt and throw everything away and say never again to only to buy everything again weeks later.

Nobody in my real life knows about this side of me.

Recently i once again bought sissy stuff and I’ve been planning a public sissy walk.

I’m thinking of wearing a

skirt

shirt

stockings

wig

face mask

bra

nub chastity device.

I’ve also been considering wearing a butt plug during the walk. (What do you think)

The thought of being seen by strangers is incredibly exciting but also terrifying

I love fingering my hole like a pussy. It started few months back when my girlfriend pegged me. Now I can't cum without thinking about cock. This is so addictive. I think she knows it now. I asked her to call my ass a pussy and she just thinks I'm so open but now I watch gay porn to cum faster.

My girlfriend also makes me suck and deap throat on her dildo. She tells me it's not gay since it's covered in her cum. I realised that I can take bigger dildo inside me compared to her. She just likes making me like this

Recently found out my friend is also a secret sissy and was wondering if anyone else has come across this situation. He doesn’t know I know and idk if I should tell him. I do think it would be fun to have a sissy friend but I think it might just be weird too. Any suggestions?

When I was alone, I would only wear girls clothes, I’d sleep in girls pajamas, lounge around in girls' loungewear. Whenever I was in public though, I’d have to wear boring boy clothes. Outside of my house usually wear boy jeans and boys' T-shirts with panties underneath. Over the years I started wearing girl clothes that could pass for boys clothes. Girl socks, girl sneakers, girls belts etc. Over the past year I started wearing baggy girl clothes in public. Baggy girl jeans and girls tee shirts and hoodies. It’s been over a year since I had to wear boring any boring boy clothes. Now I only wear girls clothes. So far, no one has noticed.

After years of being shy about my sissy side I've finally opened up to my wife and she's really taking to it well. She spent the last hour making me a custom sissy outfit. Apparently if im supposed to be a slut I might as well look like a proper girl. Next on the list high heel lessons a proper clean out. What have I gotten myself into?

Have dressed before but always quit and it's hard to make me relapse but I guess I'm looking for advice on clothing, heels, how to go even deeper.

Maybe someone could even explain why I crave it not even being my choice but the choice of another sissy or Dommy girl

I have taken about 3 straight guy's virginity and all of them ended pretty disappointingly because they all nutted within a minute lol

Were your experiences similar?

Things are not going great with women and I was considering trying something new. I already crossdress so I am like halfway there anyways. How do I know if I fit here or if I should just continue pursuing women and hope it works out?

I’m a straight married guy from the UK. I have a fantasy which goes like this - the mrs is away and I’m at home alone. I invite a dominant man to the house. He tells me I must answer the door naked except for a pair of her panties and a collar and chain. He turns up, walks past me up the stairs and sits down at my computer. Pictures of my wife are playing in the screen. He tells me to get on my knees between his legs and take his cock out. It’s already hard and in my hands as he looks through the pics. Suck it sissy he says. I put my lips around his hard cock … my first ever.

Hey lovelies 😊

I've tried several times to add achieve a sissygasm but do not get there. I have been trying for a totally hands free and maybe that's where I'm wrong. Doggy, riding etc. also I was usually trying without porn hypno etc.

I maybe having the afternoon to myself and would like to have a go.

I have a dildo and my fingers.

I'd appreciate any advice coming from you. Maybe what to watch, what to do any specific hypno or porn whatever as I try get my first sissygasm. Thanks in advance

EDIT I tried having a go at it, followed most of your suggestions that I could, thank you, watched some hypno, some porn laying on my side, taking it slow and nice, but then it got to a point I started touching my clitty. Well one hand was on my phone while I was using the other one to fuck my bussy and touch my clitty. My clitty was hard again after touching and slightly rubbing and holding. However, just as I was about to cum, I stopped touching, my ass was clenching round the dildo I was using, and I used my hand to help kinda grind on it. Damnn did it feel good 😊 😊 😊 I was actually using a bigger thicker medium dildo but then switched to the smaller slimmer one which was a bit more comfortable There was some ejaculate but thin don't think it was sperms exactly. I know I'm not there yet but I guess I will slowly get there. With the help of all my fellow babes 😘😘 Thank you, I love you all ❤️❤️❤️

So I am 19 and in university now studying away from my home country so I have so much freedom do whatever I want. That’s why I decided to be a slut on grindr and try sucking every different type of cock. I met multiple men and sucked white, indian and latino cock but i had never tried a BBC. Just when i was a craving a thick, long one I got a message from this black bull who wanted me to go down on him in his car. He assured me it was safe so he picked me up from my dorm and we headed to an abandoned parking lot in the open on a deserted street. He was really nice and friendly and we were making convo on the way to the parking lot. We went into the back and he whipped out his huge bbc. It was huge and looked delicious. The cockhead was big and his cock was so long and thick. I got so horny touching its smooth, beautiful texture and then as i took it into my mouth i could taste his salty precum. He was very dominant as he held the back of my head and pushed me down on his cock. I could barely breathe as his dick filled up my throat but i held my breath for as long as i could. As i looked down with his dick down my throat i saw that so much of his cock was still remaining outside my mouth which shocked me. I thought that I had throated his entire dick but i hadn’t which became a challenge for me so i forced myself down on the rest of his cock. His cock went deeper down my throat and wind pipe which eventually caused me to gag quite a bit but i was so happy and fulfilled that i could swallow his entire dick. It felt very different compared to all the other cocks i have deepthroated. While i did this he recorded a video of me which i found so hot. I just wish he continued as he came because this sent him over the edge. He started fucking my face and throat as i choked and gagged. My face, his cock and thighs were drenched in my spit as i could barely breathe. Then he exclaimed and grunted while he exploded so much cum down my throat. He held me down for the entire duration of him cumming and told me to swallow his nut like his good bitch. I felt so fulfilled and happy as he dominated me into efficiently extracting all his nut. I gave him a good bye kiss on his beautiful bbc and he dropped me home. ONCE U GO BLACK U CAN NEVER GO BACK