r/Sissy • • 4m ago

Discussion I think I’m on the cusp of going too far. Pretending Im the opposite of myself is only negative and escaping reality doesn’t fix my life NSFW

• Upvotes

I feel like this is like a very addictive drug and I know who I actually am and want to be


r/Sissy • • 2h ago

Question Can you turn gay? NSFW

2 Upvotes

​

I was always sure that I was straight. I was genuinely attracted to girls. At 12 or 13 i noticed male friends in my fantasies and dry humped a friend even. It all turned me on then i ignored those feelings. At 19 i got curious and looked up guys online and talked to them too. After prolonged exposure to covk and gay porn Now it seems like guys get me way harder than girls ever did. As well as orgasm. I'm 30 now.


r/Sissy • • 4h ago

Sissy Achievement! Found a glory hole, and fuck it's fun NSFW

38 Upvotes

So over the last few years I have been using Grindr, which honestly has been really shit.

I live in a big city but to be honest I hate having random men come over to my house.

A couple of months ago, I found an adult theater which caters mostly to men.

So I went and tried it. It's grimy, dirt, the lights flicker, it's kinda dangerous but holy shit is it fun.

The best part is there is a stall that has a glory hole which is something I have always wanted to try.

And you can lock it from the inside.

So in I go in with headphones, a butt plug in, cock cage, pink panties.

And I just sit there and suck dick after dick after dick.

I love how I never know who the guy on the other side is, or what your gonna get it makes it really hot and slutty.

It's honestly such a great time, for the record I'm on PReP and careful with regard to looking out for gross stuff before sucking any dick.

Just wanted to say that cos I havnt told anyone else!!!


r/Sissy • • 4h ago

Question Mess NSFW

2 Upvotes

Hey what should I do with my mess, I wanna experiment


r/Sissy • • 6h ago

Discussion Accidentally burned my clitty NSFW

2 Upvotes

So i accidentally spilled some scalding hot coffee on my crotch and while it hurt like crazy I found it made it easier for some backdoor play. When I came recently it felt like buckets. That's one upside the other is that it has made my clitty super sensitive while it grows back the nerve endings. Do I recommend it? ABSOLUTELY NOT!!! THAT SHIT HURT SO MUCH!!!! Would i do it again? NO! Do I think i am going to be cumming from anal play? Maybe but god when I do finally cum again I know I am going to be leaking something crazy.


r/Sissy • • 6h ago

Question Good app NSFW

1 Upvotes

Do you know any good app ecxept grindr for fling or any site i could find périple, im from Québec just so it can help


r/Sissy • • 12h ago

Need Help / Advice Which cage would you choose for long term chastity? NSFW

2 Upvotes

Wanting to perma lock myself I dont know if i should take my flat cage which is perfect in almost every aspect but you gotta unlock to pee and clean so no "true perma lock" possible

or

my cobra nub cage which is less comfortable and less practical or cute but i dont need to unlock theoretically.


r/Sissy • • 13h ago

Sissy Personals Any one down to chat NSFW

8 Upvotes

Looking for friends to chat with me and maybe share their experiences


r/Sissy • • 14h ago

Need Help / Advice New sex life NSFW

1 Upvotes

My girlfriend who I’ve been dating for 3 months just found out she has herpes. Obviously sex for us is going to change very differently and maybe even stop. I was wondering what some things we could still do safely would maybe do. She doesn’t know about this side of me I’ve kind of joked about her pegging me and she didn’t seem the most interested although she did seem to want to finger me and almost did after rimming my hole with her finger. We’re going to take time obviously but I’m wondering if there’s a decent way to introduce the idea of a more domme sub role. Any and all ideas welcome.


r/Sissy • • 15h ago

Question Experience with SissyLover Academy? NSFW

18 Upvotes

So years ago I found this "academy" to help feminize/sissify me and it was to take occur over time to create consistency and long term affirmations while guiding further into sissification and feminization.

I was NOT consistent with it at all, but lately I started thinking about it again and maybe trying again from scratch.

So my question for all is, has anyone done this with consistency? Is it worth it to try again and be actually committed to it? Is there anything out there that is better? What are some of your thoughts or experiences on this?


r/Sissy • • 16h ago

Sissy Story Hard Problem NSFW

16 Upvotes

It's incredibly difficult for me to get hard anymore while getting fucked. I can get hard when I pay with myself but when my partners are using me it does nothing. It's actually nice because it fits well in a cage but it has concerned one or two of my partners before. Usually after I explain it they find it hot.

I can still cum. More than once sometimes and it's still sensitive. It's like it knows it's not going into anything more than a fleshlight or a mouth ever again.

Shout out to the partner I had that made himself cum because he loved sucking my limp clitty so much.


r/Sissy • • 16h ago

Question All-natural sissy community? NSFW

7 Upvotes

For me being a sissy is purely a sexual kink/preference. I have no interest in making permanent changes to my body, like surgeries or taking hrt, over this. I just like to dress up girly and do anal play on some nights. Maybe some day I could try it with someone together but that’s a question for the future. Currently it’s basically a form of masturbation. That is also why I will keep my sissy side to myself and not tell about it to anyone close to me.

Does a community for likeminded sissies exist? Most of the subreddits are full with transgender content and hrt advocating which is fine if you are looking to transform yourself but for me it’s not something that I can take inspiration from. What I’m looking for is pretty much like r/femboys4real but for sissies. Something where I could take realistic inspiration from and set achievable goals.


r/Sissy • • 17h ago

Need Help / Advice How do i encourage my gf to letting me play? NSFW

0 Upvotes

What do i even do?

A bit of story time incoming because i need a honest opinion and there is background needed.

So I (M19) have introduced my gf (F19) to chastity a couple months ago from now and after some honest chats she started getting more playful with it and a better keyholder overtime, i hope it is not going to stop like that. As currently it is locktober i’m ofc locked but she likes to play with my cock so i will probably get unlocked for her to play. I’m not really aroused by penetrative sex or getting blown although i enjoy it slightly I can’t cum like this, i can only cum while masturbating with my hand.

I was sharing with her lately about my state of mind and the fact that i like the whole crossdressing thing and also i feel great pleasure from playing with my ass. Basically through the chat about it (mainly the crossdressing thing because she thought that the ass thing was not a big deal) she was being very negatively affected bc she immediately started associating it with the fact that i want to be a woman. I don’t, i just like to crossdress bc i feel very submissive and pretty and i like to play with my ass bc it gives me straight pleasure and i also am bi but that’s another level of it that i’m not trying to introduce as i don’t think that she is ready to talk about it. She was clearly mad about it and encouraged me to throw out my outfits and toys. Even tho i tried to explain to her that i absolutely do not want to be a woman she still stayed worried about it.

So my question basically is, how do i encourage her to accept the things i do like to do sexually or maybe even introduce them to our mutual sex life? i really enjoy being in chastity with her, she even lately started teasing me by sitting on my cage and humping it or kissing it and sending me much more spicy pics than normally. I enjoy it but am definitely not even close to fulfill my sissy desires or feel pleasure from this side of me. What do i even do to get those things to be real?


r/Sissy • • 18h ago

Need Help / Advice Caged, horny and home alone looking for advice on what to do NSFW

2 Upvotes

As the title says, stuck at home caged and horny today. Looking to go deeper as a sissy and explore more but not sure what that would look like. Just looking for some ideas :)


r/Sissy • • 18h ago

Question Sex Machine recommendations for my birthday NSFW

4 Upvotes

It's my birthday and I would love to finally have one! Looking for recommendations (in EU)
Are there any good reasonably prices machines? I would like a hismith but the average one ends up costing around 500e
I saw some recommend FREDORCH but those with the right attachments can go for nearly 400 which isnt much less than the hismith, maybe im looking in the wrong places?


r/Sissy • • 18h ago

Question where can I get captioned? NSFW

9 Upvotes

I have tons of hot vids of me fucking my dildos and I’d love it so much if I was captioned and saw myself featured in a random hypno video. Any suggestions? Are the subreddits for that? or websites? ppl who enjoy making them?


r/Sissy • • 21h ago

Need Help / Advice Fuck machine advice NSFW

3 Upvotes

Maybe a bit know topic already but what are your ideas or advice on buying right thrusting sex/fuck machine? I would like to get something sturdy or proper that has power. Noise is not a problem. Also might be interested in something that be controlled online/over distance or over calls/streams. Not extremely expencive but can spend. Right now have looked into Hismith Pro Mini or Pro 1, also looking at Lovesense Sex Machine and Mini version. So what are your experiences and reccomendation on that front?


r/Sissy • • 1d ago

Sissy Story Someone told me I looked very pretty at the mall today. NSFW

41 Upvotes

OMG! OMG! OMG! I walked around in my pink dress for about an hour today, and at one point in time a little old lady told me I looked very pretty. I instinctively thanked her in my normal, deep masculine voice and instantly wanted to die.

This happened about 20 minutes into the excursion; so I powered through the embarrassment. Other highlights of the trip include walking through 2 stores in the mall and trying on a dress in a department store. All while caged with my attached vibrating plug that I would occasionally turn on, including leaving it on the whole drive home.

Overall, an amazing experience which proved to me I can successfully pass when dressed en femme. This mall is a dying mall with very few people. I may have to go to a busy one next.


r/Sissy • • 1d ago

Discussion What’s your “yeah… that was a bit much” post-orgasm regret moment? NSFW

114 Upvotes

Alright, post-nut clarity is properly wrecking me at the minute. The second I finish I just want to chuck everything in the bin and pretend none of it happened.

Trying to lean into it so it stops hitting so hard every time 😂

We’ve all got one of those moments where it felt unreal while it was happening… then the second you came your brain went “what the hell was that?”

Mine was the night I decided to spit-roast myself with two dildos. Got completely carried away, moaning and talking dirty to myself like I was putting on a show. Came hard… then the silence hit and I realised my flatmate was in her room and had probably heard every single word.

Wanted the floor to swallow me.

What’s yours? The one that still makes you cringe a bit when you think about it?


r/Sissy • • 1d ago

Sissy Personals I need hypno or other content NSFW

1 Upvotes

Fewl free to dm me for that or to degrade me


r/Sissy • • 1d ago

Question Would coconut oil be an alternative to use with my toys? NSFW

5 Upvotes

I've heard that many people use coconut oil as a lubricant and as a good emergency alternative, even for use in water. Could you tell me if that's true or what other emergency alternatives are available?


r/Sissy • • 1d ago

New Sissy Looking for first time NSFW

2 Upvotes

Good evening girls!

I’m looking to have my first encounter with a man.

I sucked when I was younger but I haven’t done anything since being an adult.

What should I do to get ready?

Any tips on where to meet guys?

Where can I get sexy clothes for a 33 man?

Thank you all for any help you can provide.


r/Sissy • • 1d ago

Sissy Personals Looking to chat- married? NSFW

13 Upvotes

I’ll chat with anyone but am particularly interested in talking to sissies trying to navigate married life. 31 here


r/Sissy • • 1d ago

Sissy Story The Desperation is Real Part 2 NSFW

2 Upvotes

Hi everyone. This is part two.

As you know, I am a caged sissy. I’ve been locked four weeks now.

I have gone longer periods caged, and each time I stay caged it stops feeling like a restriction and starts feeling like the truth. Like my clitty doesn’t belong to me anymore. Like my orgasms don’t either. Everything I used to chase for myself has been slowly rewritten into one simple purpose: to feel someone else’s pleasure instead of my own.

To recap: I met this guy on a dating app. We were supposed to meet at the changing room at Kohl’s. Me dressed, blindfolded, and facing the wall with my ass out. He was gonna come in to feel me up… That was the plan, anyway.

But he flaked. Leaving me there cold. Basically naked. Horny and grabbing my own ass. The disappointment hit harder than it should have. It wasn’t just missed sex. It felt like being denied the only kind of pleasure I’m still allowed.

He messaged later. Apologized. Said he works nights and fell asleep, and like a stupid horny slut I forgave him. Of course he wanted to try again. I obviously said yes, and was already dripping just thinking about the possibilities.

Same plan. Except this time he wants to try the restrooms instead. Says the changing rooms have cameras when you walk in and out. I’m like… there’s cameras everywhere. But whatever. At this point I am like, just fuck me already. I want to be touched. Used. Something. So I say fine.

Wednesday at 9:00 a.m. I’m already ready. Black lace bodysuit clinging to every curve. Cage locked tight against my little clitty, balls heavy with everything I can’t release. Glass plug nestled deep, pressing against that spot, and every time I move I get a constant, cruel reminder that I’m full and still completely empty. Thong between my cheeks. Wig in a bag. Sweats over it all. Sitting in the parking lot already wet, already leaking into the lace thong. We’ve been messaging all morning. My heart’s racing, but it’s not just nerves. It’s the particular hunger that only shows up after weeks of denial — the kind that makes risk feel exciting.

He says he’s ten minutes away. So I walk in. Not as nervous as last time… but my hole is already clenching tight around the plug and my cage feels tighter with every step, like it’s reminding me what I’m here for.

Then he says he’s in the parking lot and pure heat floods me. I feel my plug shift inside me. I’m soaked. The anticipation alone is almost enough to make me dizzy.

I walk my desperate horny little ass to the bathroom. Last stall. Plan is he whistles. I unlock and assume the position, and he can do whatever he wants to my locked, plugged body… I don’t care anymore. I just really need someone to use me like the sissy I’ve been slowly turning into.

Forgot to say — I brought a cute red bandana to cover my face.

He texts me he’s inside the store. I’m already peeling the sweats off, exposing my lace-covered body to the cold air of the restroom. The cage feels heavier in the open air. The plug feels deeper. Then the restroom door suddenly swings open and two or three guys walk in. Very loud. They break the silence hard; it startles me. One goes into the stall next to me. I can hear them pissing, changing, laughing, and I’m basically naked in the next stall holding my wig. Sitting on the toilet with my plug pressed hard against that sensitive spot and my cage already shiny with precum. Praying they don’t look through the crack or under the stall to see my lace-covered legs in my Chucks… or worse, look over the top and see this stupid little sissy half-naked, clutching her wig, looking like a deer in headlights.

The panic is real and sharp.

But these weeks of denial have done something to me, and a part of me is terrified they’ll see me.

The other part — the part that has spent weeks and months learning that my pleasure only exists through someone else — starts inventing the worst or maybe the best version of being caught.

What if they do look over?

What if they find me locked, leaking, sitting here shaking?

I can almost feel them pulling the door open. Surrounding me. Grabbing me. Pushing their cocks past my lips one after another until each of them finishes in my mouth. Then bending me over the toilet or sink and pulling my plug out, and using my hole that’s been aching for exactly this… Filling me. Breeding me. Giving me orgasm after orgasm that aren’t mine, but feel more real than anything I’ve had in weeks… Every pulse of their release feeding the hunger the cage keeps locked away. Making me crave more. More cock. More cum. More proof that this is what I’m for.

The fantasy is so vivid my pussy clenches hard around the glass plug that I almost moan! I’m dripping and having a panic attack at the same time!

I text him there’s people in here! That this is a stupid idea! We should’ve used the changing room! He asks if I can get out. I say no! I am already basically naked! I am already here! We’ll just have to wait! I’ll text you when they’re gone! He says okay.

They finally leave.

I stand up. Text him everyone’s gone, put the phone down. Put my wig on and tie the red bandana over my eyes and face. Everything goes dark and hot and terrifying… and strangely calm.

Silence fills the bathroom once again, and I realize that I’m half-naked in a Kohl’s restroom stall, shaking, leaking, heart hammering, pussy steadily clenched around my plug. Every squeeze, every breath reminds me why I’m here.

A door suddenly swings open and startles me, but no whistle. Just someone pissing. Door swings open again… Nothing… the sound of water… hands washing… A flush… More water. I stand in darkness listening, hole twitching, clit throbbing in her cage.

Then someone leaves.

Then the whistle.

Oh my fucking god!

I unlock the stall door so fast my hands shake. I scramble to the wall. Hands planted against the cold tile wall. My ass out. Back arched deep. Presenting myself like the locked-up slut this cage has turned me into. Offering everything to a man I can’t even see.

Door opens. Closes. Locks. Footsteps. Then big, warm hands land on my waist and I almost come out of my skin. A stranger is touching me! Holding me. Owning me. I can’t move! A broken gasp slips out.

His hands slide up my chest, rough over the lace, finding my nipples and pinching just hard enough to make me whimper. Crotch presses hard into my ass. I feel the heat of his thick, already half-hard cock pushing against the base of my plug, shifting it deeper. I moan. His fingers dig between my thighs, stroke over my clit through the flat cage, then cup my little balls heavy with denial and squeeze. Firmly. Possessively, and I moan louder. I push back, grind on him like the desperate slut I’ve become. He’s getting harder! Hands everywhere — grabbing, spreading, squeezing, rolling my balls like they belong to him. Pumping against me slow and deliberate. I’m moaning, wet, open-mouthed, not caring who hears. Breathing hard while this man decides how much of me he wants to take…

Then he leans in and whispers against my ear, voice low:

“That’s enough for today.”

The words hit like a slap.

My whole body goes cold.

For a second I can’t breathe.

No. No. No! Not yet! Please! Not like this! I need more!

Panic floods me — not just sexual panic, but the deeper kind that comes from having your only purpose suddenly taken away. Please! I need more! I need him to pull this plug out of my aching pussy and fuck me! I need to feel him stretch me open and push into me. I need him to fill my aching pussy! I want to feel him cum! If I can’t have my own orgasm, I want his! I’m desperate for it. He’s about to walk away after just groping me and leaving me like this, unused, incomplete. No!

Without thinking I reach back and grab his cock through his pants. Thick. Hot. Hard. I squeeze it like I’m begging. A broken moan comes out of me.

He asks, “Do you want to suck my cock?”

I whisper “Yes.” It comes out cracked. Needy. Broken... Anything... Just don’t leave me yet. Let me be useful.

I turn around, breathing hard, and drop to my knees on the freezing tile. He pops it out. I flip the bandana up and take him into my mouth! The second his cock hits my tongue I almost black out. The taste of him — warm, clean, slightly salty — floods me. Weeks of denial and it feels so fucking good. Not huge. Just perfect. Thick enough to stretch my lips and make me feel owned. My cage tight against my body heavier than ever between my legs, completely useless, while I finally get to do what I was locked for.

I suck like I need it to live. Hands on the back of his thighs pulling him deeper, offering my throat. Then stroking the base, working the head with my tongue, drooling, lost in this moment. Then he grabs the back of my head and starts trying to fuck my face. I let him. I drop my hands and start touching myself. I can’t help it — I squeeze my lace-covered tits, I rub the cold flat cage feeling how wet I am, rolling my aching little balls, reaching back to push and twist the plug while he uses my mouth like it belongs to him. Wishing he would pull it out and shove his cock inside my throbbing pussy instead.

He’s face-fucking me while I'm playing with my own plugged hole! He pushes deep, pops past my tongue and into my throat. I gag, my eyes water, spit running down my chin, and he just goes harder, holding me there, using me. I am moaning around him. Then he growls that he’s about to cum. I grab his cock with both hands and jerk him into my mouth as he explodes. Thick, hot pulses flooding my tongue.

God!

I feel like I came with him.

That denied orgasm rips through my locked body while he’s shooting down my throat. Pulse after pulse of his release feels like waves and waves of pleasure. I suck and swallow every drop, moaning around him, still stroking, lost, but still trying to be a good slut for him. His load is warm and heavy in my stomach and I feel high. Complete. Claimed. The closest thing to an orgasm I’ve had in weeks — and it came from him, not me, and it feels amazing! Exactly how it’s supposed to be now.

He pulls out, shiny and spent. I drop from my knees to the floor, legs shaking, spit and cum on my lips. He pats my head, breathing hard, and says “Good slut.”

Then he walks out. Leaves me there. Just like that.

My hands on my chest and lips, I’m tasting him, savoring what’s left. Riding the high. Running my hands over my lace body, still sensitive. Reaching down to my cage — soaked, dripping with everything I leaked while he used me. The plug is still deep, still pressing, still a reminder of what I wanted him to take, wanting more. Then I realize the stall door is open! I jump up, close it, lock it and sit back down on the cold tile, thighs wet, pussy clenched tight around my plug, cage heavy… but a deep, quiet satisfaction settling over me.

I can’t believe what just happened. I’m swimming in it. I completely forget where I am. I’m not sitting on a restroom floor. I’m floating in the afterglow of what just happened. My heart is racing but calm. My skin hypersensitive. Everything is fuzzy and glowing. Satisfied in the only way a caged sissy can be — not from my own release, but from his. Completely pleased with myself for taking it. Happy he came and I got to feel every pulse of it. Sitting in the aftershock of his orgasm, still locked, still plugged, still his good little slut for a few more minutes.

Thank you for reading.

Also… I’m no longer counting how long I’ve been caged.

I’m counting how long it’s been since I’ve been used to make you cum.


r/Sissy • • 1d ago

Need Help / Advice Trouble at a party NSFW

2 Upvotes

Hello! I recently had a rough time with my girlfriend pegging me and a guy topping me. I am not new to things but this time our smaller dildo that we usually use for warmup was a lot for me. I kind of pushed past it to have a guy that we have played with a couple of times top me but I couldn’t handle him.

Anyone run into this or have advice? We warmed up normally and used plenty of lube. But I got a sharp pain deeper in me this time.