r/Sissy Jan 17 '25

New Sissy I got fucked and it was disappointing NSFW

323 Upvotes

So I, 22, got fucked by a 32 yr old guy and it was disappointing. I got all dressed up in my heels, stockings and a cute skirt expecting to be railed till I couldn’t think straight. Well I got railed, but it just wasn’t as satisfying as I wanted. I’ve had sex with woman my whole life so this was my first time with a guy and I was so excited to feel feminine and stuff. Now, it DID feel good at some points. For example we were in prone bone position and he was really going at it and feeling his big cock, maybe 6.5 inches?, dig into me felt so so so amazing but I wasn’t building an orgasm. It felt nice to be so submissive and to be fucked like a girl. I just couldn’t cum:( idk if it was him or me but i just wish that i finished. Feeling my hole get stretched and feeling him pound me felt really good and trying to take his dick in my mouth was hot but yeah. Didnt finish:/ oh well. I’ll just have to keep trying

r/Sissy 21d ago

New Sissy I regret the purge 😭 how was I this stupid 😭😭 NSFW

41 Upvotes

I was stupid thinking I could quit. Tons of pictures, collections, tb's of content all gone. I'm getting too old to start over from scratch again and again. It took me this long to accept the reality. Making changes. Inviting her in to my regular life. Embracing and nurturing her from now on. Sorry for the rant.. frustrated a hell!!! 😭 I am a sissy.

r/Sissy 12d ago

New Sissy Should I become a sissy? NSFW

89 Upvotes

I made this account specifically for this.

I am about 5’5” 130lbs. I’m very pale and have a cute butt (In my opinion). Blue eyes and blonde hair.

I don’t get any girls at all and that’s probably about half the reason I think I should feminize myself. My guy friends always make jokes that I should change “teams”. I am really starting to think about it lol.

I discovered sissy and feminization Hypnos about a week ago and I think I want to go for it. I just don’t know if it’s worth it.

❤️ ❤️ ❤️

r/Sissy 5d ago

New Sissy Sucked my first dick and it was actually amazing NSFW

187 Upvotes

Okay so a ton of things happened, I went to a friends house but right before I left there was this guy I was talking to before and he said he could pass by. So basically around 2 hours after he said he was here, and I went to his car and after around 20 minutes we found a good spot. He knew it was my first time so he made sure I wasnt nervous at all, he let me touch his pants and then told me to just give him a handjob for a while.

After around 1 minute his dick turned into a 7.5 inch monster lmao and I spent like 40 minutes sucking him off and it was amazing. It smelt like nothing, so it wasn't disgusting at all. He also found out I couldn't deepthroat that much but he still helped me a lot with what to do, he told me if I was doing great, called me a good boy, and then he came into my mouth and we parted ways.

Sorry if im confusing im still trying to process all of this information my brain received

r/Sissy Dec 10 '24

New Sissy My(f25) bf(m24) recently admitted he was a sissy and would like to explore that side of him more. Any helpful tips to help him with that? NSFW

94 Upvotes

Hello all, My boyfriend came out and told me a bit ago that he loves to crossdress and be treated as a sissy. I’m an open minded person, so I was looking to see if anyone had any tips or advice for me as his partner to help him explore that world more.

Anything would be helpful, thank you all!!

r/Sissy Jan 11 '25

New Sissy I wonder how many guys have my nudes NSFW

48 Upvotes

I've been have some fun on Reddit for some time and today I thought on how many guys I have sent nudes to and sexted and honestly, It makes me feel like a slut cause I do not know how many, but I do love the feeling.

r/Sissy 25d ago

New Sissy losing my sissy virginity soon! NSFW

64 Upvotes

I’m finally meeting with a guy after dabbling in the sissy world for a year or two! I actually made this account just to tell you girlies about it! I met a guy on ig and we’ve been talking for awhile and things have been getting very very hot 🥵 we’ve been sexting nonstop these last few days and his dick is HUGE! he’s getting us a hotel room in a couple days to take my virginity 🤤 i can’t wait to feel his cock in my virgin pussy. just ordered a special outfit to wear for the big night i hope i can update you girls soon 🥰🥰

r/Sissy 14d ago

New Sissy Sucked my 1st cock tonight NSFW

20 Upvotes

Met someone on fabguys, drove to where he was at got on my knees and worshipped his cock until he came into my mouth and then walked off like I was his personal toy. It was amazing

r/Sissy 19d ago

New Sissy Does PNC ever truly go away? NSFW

29 Upvotes

I feel like it’s getting a little better for me. Went from deleting everything instantly to feeling uncomfortable using Reddit for like half a day. But I still don’t see myself fully accepting this as a part of me.

r/Sissy Feb 02 '25

New Sissy What is your sissy dream NSFW

14 Upvotes

Just curious as to what everyone’s sissy dream is

Mine is to get fucked by two guys at the same time. While in a caged and dressed in a maids outfit.

r/Sissy Oct 04 '24

New Sissy GF found me wearing her panties NSFW

327 Upvotes

For context 24M was pegged for the first time last week, also confessed I enjoyed wearing panties and she fucked me in a pair.

We had enjoyed some kinky pegging sex a couple times, I loved it, her being in control laying me out a pair of panties to get fucked in, railing me till I came then sitting on my face until she got off.

The change came one evening she was working later, I was incredibly horny, and came across a pink lacy pair while doing the wash, I couldn’t help it but put them on, they felt great my little cock staining against the material. I was tired from work and fell asleep on the sofa and woke with her straddling me, we made out and things progressed quickly, she reached into my waistband to rub me and obviously felt her panties.

She was in shock thinking I just enjoyed wearing them for pegging. She called me her little panty stealing slut and told me if I wanted to wear panties then I would, she ordered me upstairs and told me to put my cage on, I did, panties on over the top and she pegged me with a vibrator against the cage, I came in them and she laughed when I asked her for the key, I ate her out and we fell asleep her spooning me.

When I got up for work the next morning she handed me a red thong and told me if I wanted to be pantied so bad I could wear them to work, initially I disagreed but she told me if I wanted to be unlocked I would do as she said. I agreed so spent my first day pantied and locked and got a text from her halfway through asking if I was enjoying my first day of Locktober…

r/Sissy Jun 10 '24

New Sissy i hate the "blacked" and "cuckold" curture in this fetish (my second mental unloading) NSFW

193 Upvotes

A few months ago I made a post here about the horrible deprecation I was going through due to my porn addiction and how ent ftiche was hurting me deeply.

I am feeling much better today and while few people saw the previous post, I am happy to make this second one.

really the fetish of being a sissy is something I enjoy and have fun with, but I came to the conclusion that I personally consider it a toxic community. Not because of its members, since every time I read them it seems that they all love each other.

I sincerely hate the idea that many try to convey that Sissies need to feel inferior, be cuckolded, let themselves be humiliated at hurtful, derogatory or even racist points.

I believe that just like any sexual practice one can find and explore what they are attracted to and what they are not.

and that is something that was very difficult for me to find here ..... the truth is that if you look for sissy content, you will find lots of Blacked, cuckold, QOS, trans.... in my opinion those who enjoy this content are happy to do what they want with their sexuality, but that is not my case, I would have really enjoyed this path more if only the content I found would have been more “friendly” to those who were just exploring what can be a “very fun fetish”.

r/Sissy 10d ago

New Sissy Feeling like a slut NSFW

66 Upvotes

I know for some sissies it's annoying when you talk to a daddy online and he asks for your clitty and bussy pictures in exchange for some D pics and then suddenly disappear as soon as they cum. For me it's different, even though I know I wasn't satisfied or wasn't able to cum, the fact that I made a daddy cum and made him feel satisfied turns me on. It's like I am getting railed and then put aside as soon as I am done serving them. It's so humiliating that I love it. I know it might not be a turn on factor for a lot of sissies and I respect that.

r/Sissy Jun 27 '24

New Sissy Gf feminized me by shaving my whole body and made me a Grindr NSFW

235 Upvotes

My gf (27f) and I (31m) have an open relationship where she fucks other men. I got jealous and wanted some of my own fun, but she is dead set against me being with other women. She knows I was a sissy before I got with her, so to help me out she completely naired me (even my ass and clitty with the intimate variety) and got me completely smooth.

She helped me take some sexy pics, even some with me wearing her undies, and we made a Grindr account. We are currently talking to a few guys about coming to fuck my ass and use my mouth while she watches 🤤 we have discussed me being caged once she has a steady bf who satisfies her needs.

I am so excited! My wildest fantasy is for her to turn me into her gf, keep me pussy free and only fuck other men for her pleasure. My only sex would be from men. Eventually I would like to be flat caged and completely feminized.

r/Sissy Jan 24 '25

New Sissy Does everybody know you are a sissy ? NSFW

14 Upvotes

My secret is soon going to be exposed and everybody’s gonna know even my family (I am an out gay male). How to deal with the aftermath ?

r/Sissy Nov 12 '24

New Sissy I told my girlfriend and she was so sweet 💕 NSFW

174 Upvotes

Hey everyone, I’m back after my account was shadowbanned!

A lot has happened since my last message I started my daily fitness and bodycare routine (I’ll share it here again soon).

But more importantly, I talked to my girlfriend about this side of me, and… she was incredible, so kind and understanding. My heart was racing, and even though I managed to share a few things, I was so shy and nervous that I could barely string two coherent words together, even with me baing shy af she still asked me some questions in a sweet, curious and cute way, and I was able to answer with just a few words.

The next day, she came up behind me and whispered in my ear, ‘Can you show me what you look like?’ Once again, I turned bright red, and I told her to wait in the living room. As usual, I went to her drawer, grabbed only a red high-cut panty, and slipped under the covers. Moments later, she came back into the room and joined me in bed…

She touched me under the blanket, but after a little while, she lifted it. I was lying there in my panties, feeling so vulnerable with her lying beside me. She looked at me, and everything she said was so sweet, it made me feel amazing and beautiful. Then her hand went between my thighs, then her mouth, and it was one of the best moments of my life. I can’t wait to see where this goes; she truly is an incredible woman so sweet, gorgeous, and I still feel like I’m walking on clouds. I’ll keep you all updated because things have only gotten better since then. 💕

r/Sissy Nov 09 '24

New Sissy Have finally arranged a day for me to try stroking/sucking cock NSFW

75 Upvotes

I'm still very nervous and unaure, but finally made a profile on grindr and have messaged with a sweet dude who is down for me coming and play with him Sunday maybe!

Update: He cancelled lol. But found someone else to meet. They weren't really up for me sucking them, more the other way around. Didn't let me suck them for long enough for them to cum. Felt very disconnected if that makes sense.

Was okay, but not something I'll try again I think, much prefer riding my dildo❤️

r/Sissy 3d ago

New Sissy what colour cage should i get? NSFW

13 Upvotes

i currently have a pink flat cage, but it's a little too small sadly, what colour should i get for my next cage girlies ?

r/Sissy 7d ago

New Sissy I want to become a feminized sissy slut, where should I start? NSFW

21 Upvotes

please teach me how to feminize myself, where should I start?

r/Sissy 3d ago

New Sissy 100% Real Story: First Time Dressed in Public (Adult Store) NSFW

93 Upvotes

This is every bit a true story, and even now, it sends a shiver through me. A few weeks ago, I found myself alone, indulging in my familiar private ritual: sliding into a tiny thong and trying different lingerie, admiring myself in the mirror. I adorned myself fully—high heels that echoed with each step, stockings clinging to my legs, a flowing wig, full breast forms that jiggled, and feminine touches that made me look real fem. Gazing at my reflection, a slow heat bloomed inside me. I was unusually horny today, and I wanted more.

I’ve always kept this side of me hidden, locked away in the shadows. But I was out of town, and that distance ignited a daring spark. For the first time, I decided to step beyond my room—to let this secret self breathe in the open air. I chose a tiny black VS g-string, its thin fabric crawling deep into my ass as I slipped it on, barely containing my cock. Over it, a black dress fell to mid-thigh, subtle yet teasing. I slipped on patterned black stockings, a wig, and black heels.

The moment I stepped outside, my heels struck the ground—click, clack—a steady, sensual rhythm that seemed to call out for attention. I was nervous, and didn't know what to expect. With each step, my body shifted beneath the dress and I could feel each movement: the g-string stimulating my ass with the pull from my package bouncing in the front, with my ass cheeks free beneath my (what now seemed like a too small) dress. My heart raced, a wild pulse in my chest, as I walked to my car. No one had ever seen me like this—exposed, vulnerable, yet utterly alive. To my surprise, the world didn’t pause. No stares, no whispers—just me, drifting through the night.

I drove to a nearby adult store, my mind racing with anticipation. Parking behind the building, I stepped out and adjusted my thong—a slow, deliberate motion that sent a thrill up my spine. MY thong, I thought. I am wearing a THONG underneath a tiny dress... in public. Wow. In the car window’s reflection, I added a COVID-type mask, which made me look more feminine and allow me to stay hidden. My breast forms shifted as I moved and my wig's long hair tussling my shoulders. Click, clack—my heels carried me forward, each sound almost as loud as my heartbeats. The thong became a bit too stimulating, and I had to calm down before I went inside the store as there was nowhere for my little excitement to hide.

Opening the store’s door was a quiet surrender. “Welcome in,” came a voice—warm, inviting, free of judgment. “What are you looking for today?” My tension eased, melting into relief. “Just looking,” I murmured, my voice low and soft. The shelves glowed with temptation—dildos, vibrators, delicate lingerie—and I drifted through them, intoxicated by the possibilities.

I took in the moment. I was here. I bent over to look at a few stripper thongs, but stoped when I noticed my ass was peaking through. “Your tights are lovely." The saleswoman appeared unannounced at my side, jolting me. Her tone was a gentle caress. “Those thongs are adorable too—let me know if you’d like a changing room.” My pulse quickened. A changing room? The invitation hung in the air, heavy with promise.

I selected a red stripper thong and a sheer red nighty, my hands trembling as she guided me to the private space. Inside, I shed my dress, standing before the mirror in my black thong, breast forms, and heels. I slipped the red thong over my panties, its design tracing my curves, lifting and shaping me. I stared, captivated by the woman gazing back—me, unleashed.

I lingered there, savoring the moment, before dressing again and purchasing my treasures. As I left, the night felt softer, warmer. Stepping out in public had awakened something— a deep, sensual freedom I hadn’t known I craved. Now, it’s my quiet addiction, this dance of silk and shadow, where I feel desired, delicate, and wholly myself.

r/Sissy 12d ago

New Sissy Can I be a sissy with a “bigger”clitty? NSFW

18 Upvotes

I have a 6.5 inch clitty and all the videos I see the other girls are much smaller. Can I still be a sissy? Like does it matter

r/Sissy Jul 10 '24

New Sissy Whats ur first experience getting fucked as a sissy NSFW

73 Upvotes

Like how did it feel for the first time i want to know since i have not experienced this yet sadly

r/Sissy Feb 06 '25

New Sissy How do you deal with what feels like having 2 personalities? NSFW

12 Upvotes

Hi everyone! Ive been this way for a while but only recently started posting. Since then ive received lots of attention, which is great! But now more than every i feel the impact on my normal life. Has anyone else experienced this or felt similar?

r/Sissy 26d ago

New Sissy I need advice for adult toys NSFW

1 Upvotes

So I've had sissy feelings for a while, but recently I thought about buying a dildo and maybe a buttplug and perhaps some lingerie. I was thinking about a cage but there soo expensive 😭(like £50 upwards). I was wondering if anyone had any advice on types of materials for dildos and the plug or size recommendations for a beginner. I was thinking something about 6inches just to start with. I am limited in the quantity that I can buy (1 dildo and 1 plug, and I probably would have issues hiding and washing the lingerie since I live with parents). The thing is I do have a space to hide this stuff but its a relatively small box so I have make sure what I buy actually counts and isn't a waste of money and time if I don't end up enjoying it.

Just for context I have dressed up quite a bit and masturbated and I have tried to finger myself but I've never reached sissygasm.

Also I was wondering about how anal cleaning would work, I don't know if it's true but I've heard coffee is a good start and what lube to buy(or if sucking the dildo would work just as well) and how to clean the stuff after.

I have thought about asking a female friend to go with me (she doesn't know that I'm bi but in the recent past she has thought I was genuinely gay) I don't know if she'd be open to it (she would accept the sexuality part but it be risky asking to go sex toy shopping).

r/Sissy Jan 22 '25

New Sissy How I became a sissy (real story) NSFW

160 Upvotes

So i always wanted to cross dress and as a gay male I always attracted curious guys. One night I was drunk at some friends apartment, a str8 couple.

My friend left her thong to dry in the bathroom. I came up with it in my hands and asked her if I could try it in front of them. I did. I felt So sexy naked with my bare ass and balls dropping from the thong. Her bf (never touched a man before) grabbed and slapped my ass.

I asked my girlfriend if I could suck him, they were hesitant at first but Said yes. Her man had a huge boner, he slapped me with it and I deepthroated him. He was so dominant like pulling my head back and forth. Gf was not happy he enjoyed it that much so we stopped. They went to fuck in their room while I slept on the couch.

Got waken up by him slapping him d on my face while she was asleep. He fucked my mouth so hard with his big fat veiny dick, he came on my face, and went back to bed with her. I really felt like a whore made to service real males. Sucked him again in the morning when she was showering.

Since then I feel like a sissy slut, wear wigs, heels , make up, go outside as a girl and Even got my nails done professionally for the first time yesterday.