r/Sissy

▲ 15 r/Sissy

Why are men so rude?

Why are men so aggressive and disrespectful? I have been chatting or meeting with men here and there I have had my share of horrible encounters with men that have either been rude and disrespectful or kinda aggressive if I don't do what they want I'm kinda of losing hope that I'll ever find a good guy??

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u/SissyPrincessEmilia — 7 hours ago
▲ 8 r/Sissy

I need to hide my dildo

Hey i bought a big dildo i thought i can hide it inside my chess set but balls part didnt fit. I will live with my mother for 3 months and in this 3 months she is going to do cleanings type of stuff probably. So she might see it im scared of getting caught please help me where should i put my dildo its 30cm long.

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u/MustBeLive — 8 hours ago
▲ 33 r/Sissy

Had my eyes opened to being a sissy

34 males here had the best experience sexually of my life I’ve always considered my self straight and love fucking and eating woman out but the other week I was super horny and my partner( female) has t really been in the mood so I said fuck it and downloaded grinder looking to get some head well I chat with this older gentleman and decided to meet up well needless to say I was nervous he offers me a drink and a blunt to come down I drink and get a buzz going and he gives me amazing head and after I cum he proceeded to suck on my balls huge turn on for me and then he starts to eat my ass and it’s like fireworks going off and before I can stop myself or him I beg to let me feel him inside of me next thing I know he’s got a gag in my mouth and a mini shirt and a thong on me and gas me bent over and proceeds to fuck me for what feels like hours( actually was like 50 minutes) I lost count of how many times I came I want more not just from him but I think this might have awaken my inner whore idk what to do

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u/RopeComfortable8951 — 6 hours ago
▲ 2 r/Sissy

My First Real Sissygasm?

Heyyy, I wanted to ask a question, kinda. I'm currently caged and have been for a few days. I've finally learnt how to take my full 13 inch dildo in my pussy all the way, balls deep, and as I was bounding on it while listening/watching to Bambi Tiktok videos I felt so so good then I noticed that like a creamy liquid was coming from behind my cage. So, did I just have my first actual sissygasm?

I haven't had any other stimulation on my cage just from my pussy with my plug first and then my dildo. I'm pretty sure I just had a sissygasm, but I just want to check before celebrating xx

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u/SissyAlice2001 — 8 hours ago
▲ 39 r/Sissy

Men from Grindr are arseholes

Now I know I’m not saying anything new or that anyone hasn’t already said but my god they are so annoying and time wasters. So I have a free house on Mondays and Tuesdays till 2. Guys drop out last minute. Talk to you like shit expecting for you to enjoy it when you haven’t even properly spoken to them or at least flirted first. you send them slutty pics and then they ask for a face pic and because you tell them they have to first because you’ve sent sexy pics and they haven’t sent you anything they get all pissy. And then when you do and they don’t vibe with your look they just air you. Like at least say that I’m not your type. Also I just had a guy tell me to stick my dildo up my ass and send it to him now. Like bitch pls I need to warm up first. It’s always the blank profiles as well.

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u/Material_Bug7374 — 10 hours ago
▲ 2 r/Sissy

Should I go small

So i been wearing my now chastity cage for 1 year now and I was wondering if i should buy a new one and if I do should I go with a smaller size so stick with the same size girls please help

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u/slutsissy_69 — 6 hours ago
▲ 4 r/Sissy

Trying on my first cage as im writing this!

Hi! Its my first cage and i am on the quite bigger side but bought the largest case available. The biggest ring barely fit but is the ring supposed to fit a bit like a cockring in a way? Not fully tight but like firm? Sorry if its a stupid question but its my very first time

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u/big_john_white8 — 9 hours ago
▲ 11 r/Sissy

Hello other Sissys Lookin for Friends❤️

I would really like other sissies to talk to and share tips and experiences would love to have like a Sissy group

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u/jusforfunnnnnnnnnn — 18 hours ago
▲ 2 r/Sissy

Where do yall buy clothes from?

Referring to undergarments. Like do they make specialized ones for trans people or not? And what are your favourite sites/stores yall purchase them from ?

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u/Silly_sherry_ — 9 hours ago
▲ 4 r/Sissy

Closeted guy just seeking advice

I used to be closeted and occasionally see sissies and used to date cis women. I got outted and ostracized. I lost all my male friends and dating women got hard. Well I'm a religious black guy from a conservative community. I kinda became a shell of myself since. I used to be the life of the party. Now I'm a shell shocked recluse. I just feel like a broken man. So I started bottoming, shaving, waxing to cope. I used to be a strong dominant man before I got caught. I soon realised I'm still sad so I abstained from sex and got sober off drinking. I gained lots of weight recently. I'm older now so I don't have that early 20s skinny look. I don't bottom anymore or dress and I'm trying to regain my masculine frame, but I have a reputation as a slut and girls in my community don't really want a guy like me and girls accepting enough wouldn't want such a strict traditionalist, conservative, and religious environment. I'm kinda recluse. I do kind of crave sissies but idk.. I just want some people to talk to. I crave the feeling. Its like denying myself this year it's building up the feeling, the pent up relapse and no I won't bottom anymore. I don't look or feel fem anymore but publically I'll always be viewed as a sissy.

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u/Turbulent-Book-6964 — 12 hours ago
▲ 2 r/Sissy

Need help for sissygasm

So today I tried fingering my butt after like 2 years and I didn't feel anything, like it didn't hurt but I also didn't felt good either. What should I do to reach sissygasm.

Is there are any specific points where i have to touch or should I reach deeper.

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u/PuzzleheadedEar2748 — 13 hours ago
▲ 106 r/Sissy+2 crossposts

My first time and how I became a sissy❤️

I was a completely straight guy in my teen years, but around 16 I started watching porn more often then not and for some reason I always watched the guy and the cock instead of the girl, and I always timed my ejaculations to when the guy on screen would cum.

Skip ahead about a year later and I downloaded grindr (I know I was young but who hasn't downloaded a dating site at around that age) anywho I found a guy and talked to him for abit, he sent me some dick pics and he was abit small but hey this was the first guy to give me attention, I wanted to meet up with him but got scared (to young, might be trouble, could be dangerous) so I backed out.

About a year later when I was 18 I decided to try again, this time I wanted to be a top, I was very back and forth on what I liked and at that time I wanted a top, me and the same guy still talked so I told him to go down to the park and I'll meet him.

About 20 mins later I walk down there and he says "you can jump in if you want then you can fuck me" I said "um actually if it's okay I won't jump In your car, for safety" he didn't mind so I pulled my cock out and he sucked my cock through the car window...in pure daylight...midday haha, and there were a bunch of houses who could have seen me.

Edit: it's wrong but I was 18 he was 64

After that first time I liked it, but then the thought of having cock turned me on more, I got more and more adventurous, looking for cocks to suck and take till eventually I found someone who was nearby, I couldn't host and neither could he, we thought we were at a block, then he told me to meet him down the end of my road, I did and he picked me up.

I thought fuck he is hot and started sliding my hand up and down his cock while he drove, we didn't drive far, we found this open but in night private spot at a tree next to the highway, we kissed and made out for abit then he said "drop to your knees slut" fuck I was weak and did as he said, he pulled his cock out and holy FUUUCK, about 7.5 inches and girthy as fuck, I could barely take it but I told him to force it in me, he grabbed the back of my head and rammed his cock down mu throat, eyes went into the back of my head and I was slobbering, I loved the taste I love the sound I loved every inch of it in my mouth.

After about 10 mins (felt like an hour) of throat fucking he told me to stand up and take my pants off, again I did as he said, now I had played with my toy but I had never taken actual cock in my ass so I was tight, he spit on his cock and then rimmed my ass, I came a little on the tree, then he stood back up and I felt the head go in and I screamed, he grabbed my mouth and told me to be quite, as he said that though he pushed his cock in deeper and omg I just melted.

I pushed back on his cock like I automatically knew what I was doing, he grabbed my waist and pounded my asshole till I couldn't take it anymore, which was about 45 mins of straight doggystyle, I whimpered and groaned, but I loved every minute of it, he grabbed my throat and said he was about to cum, with a raspy voice I said "cum in me daddy, cum in your little slut" and boom I felt every rope of cum full my insides, he pulled out and ahoved 2 fingers in me pulled them out and showed me his cum covered finger "oh wow daddy that was a big load" I said as I licked it off

He dropped me back home and said "see you in a few weeks baby" now whenever I can I try to take his cock and be his slut, but nothing will ever beat that first time at the tree with him and that's when I decided to become a sissy

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u/sissyslave_07 — 20 hours ago
▲ 61 r/Sissy

I was deceived, so I bought a new dildo

Few days days ago, a man contacted me about a previous post I made, he was treating me the way I like to be treated when I’m in my cage. He said he would love to train me to become his slave. He had put a lot of emphasis on the fact my penis should always be locked up and from now on I should make sure to keep it locked up at all times, except for a shower.

I could not believe what was happening, it was turning me on so much. And the fact he lived no too far away from where I live was a big plus. We talked for a few days, sometime for few texts, sometimes for hours.

One day, he convinced me I should have a dildo to train my ass before I go see him irl (since I’ve never done anything with a man before). I looked online to buy one to please him, I showed him the choices I’ve had and we choose one together. I ordered it, and it finally came today. But between the time I ordered it and the time my new toy was delivered, we kinda stopped chatting… the exanges were getting really short from his side, he didn’t even bothered to reply my last text massage…

I’m kinda sad it stopped when I was really enthousiast to obey him and explore more of my sissy side with him… but the good thing is, now I have a beautiful 7 inches dildo to play with while caged ☺️

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u/DenseCellist2357 — 22 hours ago
▲ 6 r/Sissy

Got my first thong too

I recently order my first cheap thong in online and it just arrived. Very happy to have my own piece of clothing.

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u/hanuman_shaa — 16 hours ago
▲ 3 r/Sissy+1 crossposts

Hey girls <3

Hey girlies, if any of you have any question you wanna ask me to be afraid to message me okie, or even just chat about your stories if you don't wanna post them on here and just wanna tell me about them that's fine <3

*And moderator if this violates anything I'm sorry I didn't mean to I read the rules and I don't think I saw anything about getting others asking for advice, if I did miss it I'm sorry)

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u/sissyslave_07 — 14 hours ago
▲ 16 r/Sissy

(22F) Just got with a sissy boyfriend and it's turning out to be one of the best decisions I have ever made.

I'm a pretty feminine straight girl and I've always been most attracted to more masculine men that can keep me safe, physically turn me on and take charge. The problem with those relationship dynamics though is that the woman typically ends up doing more favours for the man than vice versa because my submissive nature combined with their big egos makes them a bit selfish and view acts of service that aren't the classic "lead, provide and protect" as beneath them(and although have the physique and the hot dominant demeanour, are usually selfish in bed). It's frustrating for me because I can't stand simpy guys that put me on a pedestal and do everything for my approval so I never thought I'd be in an FLR. But despite that, I liked the idea of being served without it being from an intimate partner I'm supposed to have a normal sexual relationship with because it's way too much of a turn-off.

Last year I had a very upsetting breakup with a toxic boyfriend of over a year that I tolerated shitty behaviour from and did way too much for only to find out he was cheating on me with my close friend for months. I was completely disinterested in dating ever since then but still had needs to take care of. Which being freshly single left me with home-alone porn & bong nights with my vibrator.

I noticed an over-abundance of what was called "sissy" porn and intrigued, I checked some of it out. Much of it was solo-style porn(clearly directed at sex-starved single men) featuring lengthy-ish brain-rotting captions with stacked, dramatic short references to what I've learned is associated features to this sexual conduct like chastity cages, erection & orgasm denial, homosexuality feminine attire and anal. Much of it felt like dopamine pixel vomit that was sexually repulsive and made me cringe yet was simultaneously hilarious due to the sheer ridiculousness of the depictions. I couldn't help myself but keep exploring it a few particular nights and surprisingly ended up taking a liking to some of it that featured a big, strong masculine man dominating weak little twinks and those that involved women such as cucking and FLR/femdom depictions. I still found it very amusing but found myself getting off to the thought of having a whimpy little simp boyfriend that let's me fuck big burly hunks and potentially even watching him be fucked by them.

It quietly made it's way from my horny, THC-fuelled imagination to my resting, daily thoughts and I pondered what that would be like in real life. I know porn glorifies everything but the thought of having an obedient and humbled servant that will do everything I say and fill my life with leisure without expecting any sexual favours, acts of service or the typical affirmation of masculinity guys usually expect sounded great. I also knew that in this day and age, plenty of single men would tolerate being spoken down to, humiliated and sexually repressed just to have a young woman's attention & affection. So I was feeling somewhat optimistic.

Eventually when I was having cones at a friend's house, a guy 2 years younger that I'd met through her a few ties before and thought was sweet was there. As it does, after enough cones we were all being very open & honest about our dating lives and I still wasn't done with bad-mouthing my asshole ex. He was the only guy there with 4 stoned, giggling girls grilling him about what he's managed to get himself in to in the world of girls. He said that he's never managed to get more than a first date but would really like to have a relationship. My friend said deliberately said "Tell them about your femdom fantasy!" at the top of her lungs to embarrass him and we all absolutely lost it.

I was so glad that happened because I was dying to tell somebody about my own curiosities and I knew this was my opportunity. I ended up discussing it with him for a while and agreed that we would meet for breakfast that weekend.

I kind of felt pity for him because I knew I was not attracted to him at all and felt like I was taking advantage of his desperation but we're all adults and relationships are about compromise. I felt like if I was getting what I wanted and everything was agreed upon & consensual then I could let myself go to enjoy it. We discussed the dynamic and he said he would agree to being ordered around to serve my desires, be kept in a chastity cage I would keep the keys to and I had the final say in relationship matters. When the discussion moved to sex I said outright he would not be having any sex with me and that he would never get to see me naked which felt cruel but made him thinly smirk and widen his eyes so I realised part of him was hoping to hear that. He asked if I would get him to eat me out to which I said no to. I love the feeling of it but I have to be aroused to which I couldn't see happening with him.

At the end of it I discovered he was nice, passive, gentle and warm-hearted, just kind of spineless and timid. Which I thought was suitable for what we were getting in to. I told him he was able to come over to mine the next night to start exploring what our time together would look like and he agreed eagerly. So we agreed on a to-do list for his visit that would put his skills at serving me and handling emasculation to the test.

First was to go to the adult store to buy a French maid outfit, which I checked they had and choose a chastity cage. The worker approached us to ask if we needed any help so I took the opportunity to test his tolerance and loudly said "Oh I'm looking for a nice frilly maid outfit for my sissy-boy so he looks pretty while he cooks and cleans tonight! And for a nice little chastity cage to make sure he behaves!". He was gently grabbing at me trying to quieten me down as soon as I started but the worker just laughed with me while he nervously smiled and turned away. We left with a nice pink maid outfit that came with long white stockings and what was called a bird-cage steel cage that was 1.5 " long and dome shaped.

When we got home I told him to have a shower and to come out in his maid outfit and locked in the cage and hand me the key. He made us a stir-fry for dinner that we ate on the couch cuddled up together and damn he is a good cook. I then told him to clean up as I started hitting the bong. When he was done I told him to give me a foot massage and dayum he was good at that too.

I felt bad getting high and enjoying him slave away for me even though he seemed happy too but I let him smoke some cones and my intention was to send him home in an Uber still in the maid outfit for a laugh but we were so baked that I let get back in his clothes and sleep in bed with me.

He made us breakfast and we talked about what the foreseeable future of the relationship would look like since I had a great night and was getting really comfy with him and he was thrilled at everything that was happening. I told him if he wants to stay with me then he will only be unlocked if he needs to clean in there under my supervision but he would be locked and orgasm-free 24/7 outside of that. He was shocked and hesitant, tried to plea with me but I said he can take some time to think about if it's worth continuing seeing me, which I knew would get him to agree. We agreed next time he visited we would go get a mani-pedi and get our nails painted bright red and then go shopping for some heels in his size. He looked horrified for that but knew I meant business and understood he was prepared for humiliation and embarrassment.

He also asked if he would be involved in any way with the men I'll be seeing including if he can watch me fuck them which I gave him a maybe on. But we discussed his sexuality more and hinted he wouldn't mind "forced bi" which sounded really weird but he basically wanted to be ordered to give sexual favours to men which I connected with being forced to do other emasculating things he would quietly enjoy.

That was just over a week ago and I haven't been this happy in years! He's had a visit similar to the week prior last weekend, our friend circle knows about it(which they were very supportive, albeit amused about) and things are progressing very well. We are talking now about kinky play like ball-busting, internet and public humiliation and going to kink groups to meet willing male partners and show everyone what a good sissygirl I have.

What I love about this is that my pleasure and comfort is prioritized while all he expects in return is my attention and approval. Meanwhile I can get my sexual needs and masculine energy from any man I choose. I love seeing him tolerate having his male ego destroyed for my amusement, give unmatched subservience for my happiness, and knowing that over time he is enduring increasingly intense sexual frustration all because I'm enough of a prize. Really feels good.

I wanted to give some love to sissies around the world and please know that if you aspire to find a gal that's happy to be your Mistress, put yourself out there and you can get what you want! You might just show yourself and her a whole new world of fun. Anyway, sissies are the best!

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u/ManDestroyingBratt — 14 hours ago
▲ 231 r/Sissy

A Reality Check for New Sissies 💗 Please Stay Safe

I have been seeing more and more posts lately that feel very rooted in fantasy and not in reality. I get it. The pink fog is powerful. The excitement is real. The validation can feel intoxicating.

But if you are new, there are some things you really need to remember.

You still have self-worth.

There is a difference between self-respect and submissiveness. You can absolutely be submissive and still have strong self-respect. Submission does not mean you are disposable. It does not mean strangers get to degrade you or use you in ways that harm you. Do not let anyone convince you otherwise.

You can say no.
And you should say no if you are not comfortable.

It is your body. Anything that happens to it can have lasting emotional and physical effects. A fantasy moment is never worth the long-term consequences you are not prepared for.

STDs are a real risk when hooking up with strangers. This is not fear-mongering. It is reality. Some infections have lifelong consequences. Protect yourself. Get tested. Do not throw caution to the wind because someone gave you attention online.

Hormones and permanent feminization might sound amazing in the heat of the moment. But these are serious medical decisions. They impact fertility, sexual function, mental health, and overall health. Doing anything without medical supervision is dangerous. Please talk to a doctor before making permanent changes to your body.

Do not let the pink fog blind you from reality.

Fantasy can be fun. Exploration can be beautiful. But you have to stay grounded. Stay smart. Stay safe.

You are allowed to explore. Just do it in a way that protects your future self. 💕

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u/Sissykrystina — 1 day ago
▲ 4 r/Sissy

I ordered more sissy clothes

On Friday I ordered a skirt and thigh highs and a new flat cage and they are coming in the next couple days!! I really hope I feel more like a girl. I got new lube and a douche too so I'm gonna dress up like a girl and fuck my boy pussy so hard. I'm so excitedddd!

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u/StartingLandslides — 18 hours ago
▲ 1 r/Sissy

Going out

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Usually I like to dress up as a femboy/sissy at home but I decided that Saturday I'm going to go out to a gay bar, I'm not confident enough to go out dressed up yet but I'll probably wear my thigh highs under my pants or something, I'm kinda hoping that there will be guys at the bar that would be interested in me and maybe take me home for the night

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u/WillingTip6597 — 17 hours ago
▲ 2 r/Sissy

Looking for friends ^_^

I’m looking for more friends that I can chat with share experiences and whatever else dm me!

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u/Ok_Hair3346 — 15 hours ago