/r/Sissy
A safe place for sissies and those curious about sissy culture to talk about all things sissy! Ask questions or discuss about anything sissy related :)
18+ Only
r/sissy is a safe place for sissies and those curious about sissy culture to talk about all things sissy!
Ask questions or discuss about anything sissy related :)
Please read the rules before posting!
Rules:
1.18+ only
2.Be kind
We don't allow any insults, hate speech, homo- and transphobia or other signs of intolerance. In short: Just be a decent human being.
Also, no blackmail or lost bets or anything that has any potential to be without consent. General discussions about fantasies that touch such topics are okay, as long as it does not get too graphic and detailed. The mods will have the final ruling over what is okay and what is not.
3.No selling, begging, spam, "upvote if" posts/comments of any kind.
4.No advertising unless mod approved. Read description for how to get approved.
Unless you get an advertisement approved, no advertising is allowed, including directing users to your profile
If you have something that you think is relevant to the sissy community (meaning support, help getting started, resources, etc.) message the mods before posting to request a mod approved advertisement. After reviewing the mods will approve or deny your request. If approved, make your post and the mods will flair it with a special flair indicating it has been approved.
5.Evading Automod or existing bans will lead to a permanent ban
Trying to actively circumvent Automod by for example trying to obscure specific words or using any other action to do so will be punished.
Same goes for trying to evade a ban by using a different or new Reddit account.
6.No personal information of any kind
7.Make your post under the appropriate Flair. Flair guidelines link in this rule's description.
Flairs are pretty straight forward, if you are unsure about what they mean, check out our post flair guidelines wiki page
If you make your post under the wrong flair, it will be removed.
8.If you have a new account use the "New Sissy" Flair. There are limitations, see description
Your account can be just created, but we still require at least 2 comment karma and a verified email to post under this flair
We do not allow Personals or Task/DM Requests under the "New Sissy" flair.
This flair is not for gaining karma, this flair is for new sissies to ask questions to the sissy community
9.Personals of any kind must be flaired with "Sissy Personals" or they will be removed.
Sissy personals both directly and indirectly must be flaired properly under the "Sissy Personals" flair. Its at the mods' discretion whether it requires the flair or not.
You may ask for advice in DMs in the Need Help / Advice flair, but nothing more than that
Also, please keep in mind rules 6, 10 and 15!
10.We do not allow non-sissies to make personals.
11.If you add a user flair, please follow the guidelines linked in this rule's description
12.All interactions have to be in English
13.No photos, videos or other media
14.No off-topic discussions
15.Post requirements/restrictions
We do have the following minimum requirements to post or comment:
Comments: Account age of at least 2 days
Posts using the New Sissy flair: At least 2 comment karma and a verified mail address linked to your profile
Posts using any other flair: Account age of at least 10 days and at least 2 comment karma
We also only allow one Sissy Personals post every 3 days per user. Any failed attempt to post a personal request (e.g. when using the wrong flair) will also count here.
/r/Sissy
I've just recently stepped out into the world of being a caged sissy. Not my first time being caged, but finally found one the actually works and doesn't pinch. (lt's hard with a larger clitty) feel so daring and excited right now. No one at this bar knows l'm caged and would love to be found out by a dom.
I also just started the grind to a sissygasm. l've come VERY close lately, but know it wasn't the true thing. I cheated a couple times and basically denied a normal orgasm with plugs and toys, but I hope to have the real thing one day. It's gotten so crazy that I ache for something in my booty every day!
I want someone to fully feminize me. Are there any subreddits I should be looking on for people in my area?
I really love this fantasy, I have plenty of clothes, caged myself etc, but whenever I fuck or ride my dildo it really hurts inside of me. I have lube etc and make sure to "stretch" the hole first so that's not a problem, however it always hurts too much so I haven't been able to achieve that sissygasm or have a good session yet. Any advice?
I'm new and I what some suggestions for what to get I have a butt plug set, a cage, dildo, and some feminine underwear can anyone help me suggest things to get?
I’m down to just chat and maybe do some dirty stuff. Please dm me if your interested. 🥰
So, I'm (23M) a sissy/femboy sub-lurker for a while now, and I feel like I would like to take action and actually begin the sissification of myself.
As a first step, I would like to feminize myself from the inside, before I would commit to the outside.
I feel like it would be more fun and personal if I could find someone who would help me on this journey. I know it's not necessary, but I would like to give it a try with a "teacher".
I still have a few mental holdbacks, so I think it would be more liberating if I could solve these with someone else's help.
Where do you think I could find someone to help me break these mental chains and make me the sissy I've been dreaming to be?
So I've stopped touching my clitty,even though I don't have a cage yet. But I've also been watching sissy stuff whenever I get the chance. So I'm just super horny and then the other night I ate out my gf and she wouldn't touch my clitty. So I've just been throbbing anytime I think of anything sexual or see sissy stuff
I dress more and more, interact more and more with men online. I can’t stop thinking about taking my first cock, oral or anal. I’m literally on my phone hours each day and night.
Question is, how do I actually go for it, it’s hard to find people to actually meet. And how do I tell my wife how far I’ve gone in this lifestyle. She knows I wear panties daily, and she’s pegged me often.
Who has gone through the same thing? Advice?
Does anyone else struggle to do any work when working from home? I find myself so distracted browsing subreddits such as this fantasising about all the fun I could be having instead of needing to work 😪
Anyone have any tips to get over this?
A week ago i had another experience of getting stretched by the same guy and this time it was really great. Less painful and more fun. This time i gave him deep throat and licked his pre cum. Damn that was really hot. He fucked my mouth even harder than my ass. Another thing which we used was sexy toys which really enhanced our pleasure. Making him cum makes me proud of myself. Thank you for reading it.
I was wondering if there is any difference between real thing and dildo, and if that how would you describe the feeling?
I was having a nice quick session with my favourite dildo and I got into a rhythm and it felt so good. I haven’t had a sissygasm yet but this was a step closer. I started to touch myself has I pumped the dildo in and out and all of a sudden I had a huge orgasm and I stroked and pumped at the same time. So much cum came out it was the most I had in a long time. I had to just sit there for a second to get back control of my legs as they were shaking like crazy in the floor. It was the best feeling ever and what makes it better is I’ve been talking to this guy on grinder and he wants to use my toys on me and I got me thinking I might not be able to control myself and I might just have to make him take me.
Hey!
I've been a lurker on these subs for a while, but I never actually started to act on my desires. When I'm in my horny mood I fantasize a lot about sissification and it resonates my really deeply, but when it would be the time to actually take act (meeting with a guy or buying my first clothing) I just chicken out. I live at my parents' place, so that gives me an extra dose of caution for sure.
My question is, how did you actually commit to this? I both agree with my horny side and my post-nut side at the same time :(
After days of just licking precum off my fingers I finally did it, edged 2 times and finally came in my hands. I first sniffed it, oh the smell was so arousing. And then finally licked it, it was salty and a bit tangy. I enjoyed the thrill.
I'm looking forward to my next adventure just straight up eating it off my hands and licking my hands clean, I'll get there eventually 💕
Attention all dominant alpha Macho Men! I am a 36 year old submissive sissy slut from Germany in desperate need of cruel and merciless alpha macho who clearly shows me who's the boss. I need to be manhandled roughly and exposed mercilessly.
Hi!
So, I've been a lurker on these subs for a while now, but I never actually started my sissy journey myself. I live at my parents' place and I don't really have time when everyone would be away from home. Most of the time, I masturbate in the bathroom, because that's the only room with a proper lock and I can pretend that I'm using the toilet, so it's not super obvious that I'm practicing self-love :) I do it sometimes before sleep, but everyone is a night owl in my family, going ninja at night is quite a challange as well.
Keeping the clothes and toys somewhere hidden is a whole different story.
So, those of you who doesn't live alone, how do you do this? Do you have any tips or tricks?
I would gladly talk about starting this in general as well :)
Hi everyone!
If you’ve read my other posts, you know I’ve been progressing pretty fast 🥰
Tonight, the girl that’s been controlling me over twitter gave me a task - to find another cock to suck!
About a week ago, I sucked one in a park and felt so slutty! Tonight, after searching for HOURS on grindr and sniffies, I finally found someone willing to drop a quick load to me. He wanted it to be anonymous, so I left the door unlocked, dressed in my girl clothes (plugged and caged ofc), put on a cold weather mask that can cover my whole face except my mouth, and began kneeling kneeling in front of my door. He came in, pulled down his pants, let me suck his cock (a BBC, I might add!! Bonus!!!) for a while, then came all in my mouth! He said thank you and walked out 🥰 the whole ordeal took less than 10 minutes, which I was glad abt because I need to go to sleep!
My package still has yet to arrive but hopefully will sometime this week. I’m so happy I’m turning into such a cum addictied sissy slut!!!🥰😵💫
I want to buy a dildo, but how would I hide or slash use it? I live with three roommates and it is a shared shower room. Do I hide it in my stuff when I go to the showers?
Is wearing chastity enough to shrink my clitty or is there something else I can do to keep it small and limp? I know by not playing or touching it is a good thing and I am glad I managed to do that! I am also wearing chastity as much as possible! I have managed to cum by only using my mind and no touching! Is there anything else I can do to make it shrink more and faster?
I am finishing locktober strong this year, it’s my second day I am wearing my chastity to work! Yesterday was so fun and exciting being caged the whole day! It also made me super excited for getting dressed at home! Thinking about outfits and looking at shein the whole day! Am I supposed to be a woman?🙈 This is what excites me and gives me energy through the day as my job is very manly!
Do you do those dildo hero's you see on sites such as hypnotube?
If so, which is your favourite, which is the best dildo hero?
Personally, I am quite partial to "Ass to Pussy Hero 1 poppers edit" by Last2know on hypnotube, mostly because it's short and sweet and it's made me cum a couple of times during it's quick 3rd round.
I'm in desperate need of advice...
I've been dressing up in secret for years and can't stop fantasizing about being used by older men (like 50+). I don't really know how or when it started, but it's become an overwhelming desire that just gets more and more intense every day and I've finally admitted to myself that it's something I need to experience in real life so I can decide if it's really what I want and not just a fantasy. The problem is I'm starting to wonder if I'll ever be able to go thru with it and so I'm looking for advice to help me take the next step and meet in person for sex with an older man.
A little background for context... I'm a secret sissy. Although I've been doing it for years, none of my friends or family know about this side of me. I'm totally uncomfortable with the idea of going out in public dressed up, probably mostly out of fear that someone I know will see me and recognize me.
I'm not interested in transitioning. For me, it feels purely sexual. In my day to day life, I don't feel like a woman. But when it comes to sex, I totally relate to the female role. When I watch porn, I always imagine myself as the girl. I didn't realize it until somewhat recently, but even before I ever saw sissy or trans porn, I subconsciously put myself in the female role.
I'm an attention whore. I absolutely love knowing that men want to fuck me. I love when they compliment my body and tell me how they can't believe I'm not a real girl. I have accounts on multiple "personals" sites/apps and I just love having men lining up to be with me. It's addicting.
I'm a virtual slut. I've done pretty much everything when it comes to online sex. Chatting with older men, trading pics, broadcasting on my webcam for a room of random men, posted sissy selfies and videos online, phone sex, and 1-on-1 video chatting. Sometimes it's totally random like Chat Roulette but I've also had online "relationships" with real men in my area with mutual interest/intentions to meet in person for the real thing but it never ends up happening...usually because I chicken out at the last minute.
I've put a LOT of thought into why I always back out and I think there are a few main reasons...
Guilt/shame. After I cum when dressed up or fantasizing about getting fucked like a girl by a real man, I usually feel guilty/ashamed and wonder wtf am I doing? It doesn't take long before I'm over it and right back at it again, but the immediate regret is pretty intense and I'm afraid it might be a lot worse after I cross the line from fantasy to really having sex with a man.
Awkwardness. Since I don't feel comfortable dressing up in public, I'm not sure how to avoid the awkward arrival and departure when I'm not in "girl mode". Once I'm dressed up and alone in a hotel room with him, I think I'll be so turned on my sissy instincts will take over and I can just give in and let it happen. But the before and after moments make me feel so anxious and I don't know how to handle it.
Disappointment. I've fantasized a LOT about dressing up, sucking an old man's cock and letting him fuck me and use me and I can't get enough of it. I have a plug, vibrator, and realistic 8" dildo with a suction cup that I can deepthroat and take balls deep in my tight sissy hole, and I love how it feels. But what if the real thing isn't what I thought it would be? What if I'm all dressed up like a total sissy slut and the guy I'm with turns out to be a horrible person and treats me like shit and humiliates me? What if he's super aggressive and just shoves his big cock in me without starting slow and just pounds me as hard as he can? What if he starts to record video of me on his phone?
Am I totally overthinking it or are these legit concerns? Has anyone else had these fears? I feel trapped because I know these thoughts/fantasies aren't going to stop until I've at least tried it once in real life, but I get so nervous and worried that I eventually chicken out and don't go thru with it. How can I overcome my fears and finally give in to what I've wanted for so long?? Please help!!
-Nikki
Hey girls, i love BBC and was wondering what subreddits do you y’all use to get attention from them. Please help a sissy out.
I CAME OUT TO MY MOM AND SHE WAS FINE WITH IT!!!💖
Im still really new to all this but a little while ago I made a really big step and got my first cage and a few pairs of panties. Idk why but shortly after I put them away and never got them back out. Idk if I was scared or embarrassed but I pushed the sissy inside me down and didn’t let her out. Until now I guess. I’m not sure what’s driving me to open back up and make this post, maybe it’s true desire, maybe it’s just a relapse. But either way I’m hoping to find someone to take me in as their sub and train me.
Also, here’s a little bit about how I got into all of this:
I imagine it started for me like many others with porn and hypnos. I always loved vids with really hot girls pleasing big thick cocks, but slowly I realized how my attitude towards the vids started changing. Where before I jealous of the guy with the massive dick being pleased by the most beautiful women, I began to find myself being more and more jealous of the women. I began to wish that I could look as stunning as them, that I could wear the sexy lingerie they had, and eventually just wished that I was them and was in their place, and not the man’s. The more and more I watched the more I could feel the inner sissy trying to get out, so I guess here I am again. Letting the desperate sissy take control until someone else takes control of her/me.
I respect all of you ladies for guiding sisses through the process. I just wonder how to or if I can go through with it. Ive been watching sissy hypno aboout a month now and when im horny im secretly horny for cock. When I eventualy cum, which doesnt take too long,I feel shame. Like I let someone down. I know its something I desire but the flip after nutting is sad and im just a bit confused as you might tell. Anyone relate or got advice?
What three wishes could be twisted around to make someone into a sissy unintentionally?
Hi again ladies,
I’ve obviously seen this in porn flicks etc, but have any of you ever collected cum from guys and kept it to drink?
Particularly this comes up in gangbangs but would love to hear your stories
Xx
i was hanging out at home when daddy texted me. he had a very long day and needed some stress relief. i was free and figured why not, and im sure glad i did. i had been so worked up all day being in my chastity cage.
i met up with him at a local park and hopped into the front of his pickup truck. we chatted for a moment, but he couldn’t wait and immediately pulled out his cock. i knew what i had to do, and got to work. i slurped his cock, and gagged on it repeatedly. moaning with excitement to taste him. he then pulled down my pants and started teasing my hole. i was so horny and my clitty strained against my cage. he had me lay down across the seats and spanked me like a good sissy. and the best part came when he said he wanted to come on my ass.
we both got out of the truck and i bent over on the bed for him to cum all over me. he had other plans and started to put his cock inside me. i was shaking in excitement and eagerly pushed back. he started thrusting inside me and quickly came in my hole. i think it’s safe to say i’m daddy’s girl now.
I went into a local porn theater… met a black guy who asked if he could join me in the booth. I was super nervous not really having experience but wanting to give my best effort… and he exploded all over my face. Very very happy sissy tonight 🤤