r/Sissy

So I’ve been living with my roommate for about 6 months now. He knows I’m a sissy because I dress publicly, he’s always been curious about my lifestyle and I’ve openly admitted to sleeping with random men and how I’m okay with being used by a complete stranger. He has a girlfriend but he’s always been curious about trying something with a sissy or femme type. So I told him he should try it out, see if he likes it, I didn’t know he was referring to me sleeping with him as him trying it out. So over the course of a couple days after that conversation he slowly starts coming on to me and keeps teasing me, I eventually got the hint and completely gave in to him, he’s a very attractive man and I started making out with him aggressively while humping him, I get on my knees and take his dick out of his jeans and he’s so hard and big I completely melted and started leaking, I gave him the nastiest blowjob and afterwards he wanted to fuck me but I hadn’t prepared that far in advance so I told him next time, to make up for that I let him fuck my face until he nutted because I refused to miss out on tasting his cum. For the last few days we’ve been going crazy, he’s fucked me at least 2 times a day. It’s hard to resist such a convenient and easy breed session, he always tells me my pussy is so much better than his gfs.

So many guys msg me and they have like tiny cocks and are always like send pics or out on this outfit so i can jerk while sending like one sentence messages with bad grammar.

Like ik I’m supposed to serve but I only serve MEN, not wimps with anything below 7 inches who don’t know how to dominate me properly and assume I’m just gonna do my 1 hour makeup routine so they can cum and then delete my profile

Maybe I’m being too bratty or selfish but if you wanna fuck me have a big dick and actually dominate and degrade me with thought out messages.

What do you girls think, am I being a rude bitch or should I just serve everyone like an actual slut?

dont get me wrong, photos/videos help get the imagination Julie's flowing, but they hardly put any effort in and just demand photos and videos.

Where is the intense, naughty word play, like a sissy hypno from a strong man??

hii girly, I was wondering if I'm missing any gooning sissy sites lol there's the classic hypnotube, sissyhypno, porn hub , xtube, etc but I was wondering if there's anything more for sissies lol

I'm curious to know in what moments you feel like being a sissy is worth all the work to get ready and as feminine as possible.

Is it the exposure? The moment you are wearing that new lingerie you just bought? The conversation before a meeting with a new man.... What is it?

He texted me and he’s older than me and omgggg he’s making me call him daddy and his cock is so big and uncut like so so worshipping looking :3 he tells me how it smells and AHHH IM ADDICTED OMGGG

Mine would be with a fuck machine, I had my sissygasm but I was to frozen in place to stop the machine and it continued till I started to squirt

So i had my first time with a guy this weekend and honestly... I felt kinda underwhelmed. The guy was nice and he was clean so I'm not complaining about that but i thought i would have 1 of 2 reactions, 1:absolutely hate it and never want to do anything sissy related again or 2: really enjoy it as I've been building to this for years. But my immediate thoughts afterwards were just underwhelming. He was a bit smaller than me (I'm 7 inches so he was probably 5-6 inches) and I use a dildo thats 8 inches so maybe I'm just used to a bigger size but I'm not sure. It was also very quick, like when girls say that guys only last 2 minutes I didn't realize that some guys really can't last longer than 5 minutes. I was in and out within 15 minutes including cleanup. All in all i still wouldn't call it a bad time but just not what i was expecting. I'm considering trying again but I dont know if should. Does anyone have any advice to make the next experience better or should I just stop being a sissy?

Hey ladies 😊...

A quick question 😉 , what was your first feeling when you were dominated/dominating. Where you overwhelmed ? or did you get absorbed in the pleasure 😆

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So, I decided it was time. Time to show the world my sissy side, to fully embrace it and own it. I dressed uo in a black mini skirt, short cut off top with the phrase "fuck me" printed across it, a sexy lace bra with matching lace panties, and my inverted chastity cage that says slut across it. as soon as I got in and strated putting my things in my locker, I already had attention from multiple men.

Once I was ready, I walked out into the common area, and luckily for me, got immediate attention from a group of hung men. needles to say, I spent 4 hours on my knees, and had many cocks of all shaoes and sizes in my mouth and most importantly, in my bussy!

Tonight is a night I'll never forget, and a reminder of why I became a sissy!

Anyone into it? What are your experiences?

Any advice would be greatly appreciated.

yesterday i was asked to go out to hang with some friends and have a few drinks at the park. at that point i was at home fully clothed in my pink panties, lace bra and cage and thougt to myself i just put clothes over and wear it outside as i never did that before. the whole time i was there drinking with them i got hornier and at some point i was more focused on the feeling of my panties and cage and how good wearing it out felt without someone knowing then the conversations. i kinda hope they suspect something but at the same time dont. as i got home i took a vibrator and massaged my dick through the panties and cage till i came so hard from it i loved every second of it

might do it again today as i go out again

I had a wonderful idea while working out this morning. IMAGINE a rave where it's just a bunch of sissies and they all have vibrating chastity's on that vibrate to the beat. Hung dudes and mistresses with straps will be there too. You dance until the pleasure starts to become to much and you fall to the ground on your knees and start pleasuring cock with your mouth or ass. Fuck I have a new fantasy. Bunch of sissy rave sluts going wild <3

I finally took that extra step and bought poppers last night, figuring that they wouldn’t do a whole lot and wouldn’t be super effective.

I was so wrong.

I got in a horny sissy mood with my clitty locked up and hypno playing, and took a big hit. Oh my gosh. The instant I took a big sniff, my head went foggy and I couldn’t think straight. I just needed more. I pulled out my dildo and started riding it nonstop for two hours. I just needed cock. Didn’t care where it came from or what it did to me.

Needless to say, I’m now hooked. That empty headed feeling of bliss and cock is something I never knew I needed in my life.

so I have this monster dildo right, as I'm sure many of you may or may not know by now lol

one issue with it as great as it is, it's suction cup don't work for shit lol, like it's too heavy for its own suction cup, no matter where I put it it doesn't stick and if somehow it does stay it falls the second I try put it in, even the floor doesn't work, I have to like awkwardly hold it on the floor or wall with one hand, which kinda limits the enjoyment, positions and how aggressive I can make use of it 😅.

anyways I just wanna know if there's ways to stick it better or fix it to a surface so I don't have to gold it anymore and can more or less get the full use out of it

I was on Grindr and started chatting with a daddy who’s in his 60s. I love older men, something about them just makes me so wet. His dick was so nice and he shared a couple of videos of him jerking off, I just had to meet up with him. I put on my naughtiest clothes, I have this little lingerie one piece skirt and top set that’s super revealing. When I walk you can see my ass jiggle and if I’m not wearing panties you can almost see my dick. I combined that with my high heel boots and made my way to his house.

Walking in broad daylight like that just turns me on so much I was already leaking while walking up to his door, I knock and he opens and he’s standing there completely naked already hard, he’s just as much of a exhibitionist as I am.

I come inside and he slowly starts rubbing my soft silky legs and starts teasing my caged little clit. I started kissing him and he tells me to get on my knees, so I do and he calls me a good little bitch boy and tells me I’m not allowed to use my hands, he feeds me his hard throbbing cock and as I’m throating him he tells me that I belong to him now. Daddy took me to his couch and slowly started licking my pussy before he put his dick inside of me, I already came once during my feeding session so I was super sensitive to him penetrating me and started leaking loads of cum, he made me shake and moan like a little bitch would.

Once he finished breeding me he told me I could stay and recover for a bit before I left but I wanted to stay and recover so I could get fucked by him again lol, he said he was too tired to go a second round but that I could give him another blowjob, so I did. He covered me in cum and his moans were so hot I couldn’t help but cum myself. He thanked me and told me that this wouldn’t be the last time I see him, I walked back to my car covered in cum and spit and I felt so slutty, I hope one of his neighbors saw me walking back all degraded and filthy in my slut outfit.

I’m still very new to all of this but absolutely LOVE the type of men I am getting now regularly!! Now I’d like to arrange a gang bang and be totally slutted, used and degraded by 4 or more men at once. I live in a small city (Wilmington, NC) in the south. While Wilmington is more progressive than many other parts of the South thanks largely to a massive influx of transplants, it’s still pretty closeted. Of course, I would have to meet all of the men in person to get their “vibe” and determine if I am into them and they are the right type to dominate me and bring all of the sissy slut out of me. Any advice on how to go about arranging such a thing?

Hi all..

So, I don't know how to say this, but I have lately been very interested into feminine men , sissy , trans and ladyboys. I don't like masculine men or ripped men , I like the feminine side . I know i am straight , I'm just a bit curious about this side 😊.

The first time I saw sissy po*n , that just got me hooked in a strange way.. I don't know how to explain the feeling.

Sometimes, I just want to do it with a beautiful sissy , sometimes i want to dress up and want to be handled by a confident mistress/sissy. I genuinely like girls so , i don't know how to feel. So, if anybody have had the same problem, please tell me how you figured it out..

The only other acceptable way to cum? Plapping.

As a sissy, is Plapping acceptable?

Hitting/tapping your clitty balls with your hand or dildo.

Ideally a BBC dildo, needs must.

I personally have a cum a few times from doing it, best way to do it:

1. comfortable cage. Not to tight by sufficiently locked away

2. don’t rush, cumming is a bonus but not the goal. The goal is to enjoy the Plapping and humiliation.

3. Porn is a must, BBC porn or BWNO ideally

4. BBC dildo to Plapp your clitty with.