r/Sissy • • Aug 14 '26

Mod Post Our stance on intolerant behavior and dealing with delicate topics NSFW

21 Upvotes

Hi everyone,

Due to some incidents in recent months, we'd like to clarify our Rule 2 and our stance on intolerant behavior in this community. We'd also like to take this opportunity to clarify our stance on edgeplay topics and how they are handled in a safe and consensual way.

We're a kink community, and a lot of what happens here is intentionally edgy, provocative, and rooted in power dynamics. Humiliation, degradation, and strong language can be part of consensual roleplay and fantasy, and that's not going to change.

At the same time, we need to be clear about where kink rhetoric ends and real-world intolerance begins.

What is allowed

Within the bounds of our rules and when clearly framed as fantasy / roleplay:

  • Kink-typical language around power, submission, and degradation (e.g. "worthless sissy", "owned", etc.)
  • Discussions about kink dynamics, including those that involve race, gender, or sexuality as kink themes, as long as they:
    • don't target real people or groups outside the scene,
    • don't present stereotypes as truth,
    • and stay within the realm of consensual fantasy.
  • General discussions about kink, identity, and experiences, even when they touch on difficult topics, with some limitations to edgeplay (i.e. CNC, blackmail, exposure, extreme violence, etc.; see additional notes below).

What is not allowed

We do not allow content that crosses the line from kink into real-world discrimination or harm. This includes, but is not limited to:

  • Denying or pathologizing identities
    • Statements that devalue or deny other people's identities, orientation, heritage, etc.
    • Framing real identities (trans, nonbinary, etc.) as "just a kink" or "mental illness".
  • Dehumanizing real groups
    • Racist, transphobic, homophobic, misogynistic, or other discriminatory statements presented as fact, not as part of a consensual scene.
    • Using stereotypes about race, gender, or sexuality as if they were true descriptions of real people.
  • Harassment and targeted attacks
    • Insults, threats, or demeaning language directed at specific users or groups outside of a clear roleplay context.
  • Blurring the line between kink and reality
    • When it becomes clear that someone is not engaging in roleplay or fantasy, but is expressing genuine discriminatory beliefs about real-world groups, that content has no place here.

Additional notes: Edgeplay (CNC, blackmail, exposure, extreme violence, etc.)

We allow meta-discussions about edgeplay kinks, including:

  • Sharing experiences ("I have this kink, does anyone else?"),
  • Asking questions and discussing risks / boundaries,
  • Safety tips on how to explore these kinks more safely.

When discussing these topics, descriptive language is ok, but graphic / erotic detail is not. If your post/comment reads more like a story than a discussion or safety guide, it probably crosses the line.

Not allowed:

  • Content that glorifies or romanticizes these kinks (e.g. framing them as "what everyone really wants", "the purest form of kink", etc.).
  • Posts / comments that actively seek partners to act out these kinks in real life (e.g. "Looking for someone to expose me", "Who wants to blackmail me?").

Why this matters

Many of our users are trans, queer, or exploring their gender and sexuality through this kink, and while we are primarily a kink subreddit, we still want to be a place where all of our users feel safe and at home. Content that denies their identities or frames their existence as negative is not just "edgy kink talk", but it actively harms people in this community.

We will remove content that crosses these lines and take action against users who repeatedly engage in this kind of behavior. Our goal is not to police fantasy, but to make sure that fantasy stays fantasy and doesn't become a cover for real-world intolerance.

Quick self-check

If you're unsure whether something crosses the line, ask yourself:

  • Is this clearly framed as fantasy / roleplay?
  • Does this target real people or groups outside of a consensual scene?
  • Would this make someone feel unsafe or unwelcome here because of who they are?

If the answer to any of these points raises concerns, it probably doesn't belong here.

Thank you for understanding. If you have questions, feel free to comment below or contact us directly through modmail.

 


r/Sissy • • Jan 30 '25

Mod Post Political posts NSFW

39 Upvotes

There have been quite a few posts in the past few weeks and months, that were discussing political topics, especially surrounding the US Presidential elections.

While we understand that this has a major impact on the lifes of many members here, it also sparks a lot of passionate and heated discussion. And while we certainly welcome any form of discussion, it still has to be done so in a constructive and civil way, no matter how different other people's views may be from your own.

Since in those posts and in a few posts in the past things have derived from being exactly that, we have come to the conclusion to ask you to stop posting any political posts on /r/sissy. We understand that politics have a major influence on the LGBTQ+ community and therefore by extend on sissies all over the globe, but we feel like this is not the right place to discuss this, as it can become too controversial. We may allow discussing those things again at some point in the future, when we can ensure that it can be done in a way that works for everyone, but for now we feel like it is best to keep those sort of discussions outside.

We have always gone by the rule of "Don't be a dick!" and that is a rule we stand by and it is a rule that is free of politics, religion, gender, sexuality, race or other factors other than just being a decent human being who is open to other people's views and way of lifes and who doesn't shame, insult or threat others, even if they do not represent what they stand for. So as long as you follow that simple rule, everyone is welcome in this community.

Therefore keep in mind that ultimately we are one community and there is already a lot of separation going in in the world, so let's not add to it here.

That being said, we have closed the recent three politics posts from the last hours and will keep them closed. We will also investigate to thoroughly check for any rule violations which there are plenty of on both sides of the fence. This will probably take a day or two, so expect that this will be dealt with in accordance to our rules.


r/Sissy • • 1h ago

Question Are the sissygasms worth it? NSFW

• Upvotes

On the brink of rebuying a cage, dildo, butt plugs, and panties and before I drop money on this again. Can an experienced sissy tell me if a sissygasm or whichever strategy I can do once I have a cage is really worth it and better than just beating my meat?

Thank you cuuuuuuties 😘😘😘


r/Sissy • • 9h ago

Question Should I keep going? NSFW

18 Upvotes

I’ve been on and off watching sissy hypno and porn for a while now. I’ll create accounts and delete them just to create more.

Recently I got really into it and started posting myself on a whim. I didn’t originally plan on posting much but my posts seem to be doing pretty well.

Is it too late for me to go back now and should I keep going?


r/Sissy • • 11h ago

Tips for Sissies Act as gay and fem as you can for daddy!!! NSFW

24 Upvotes

I’m telling you girls that men go crazy for the cute dumb girl act!!!

Walk with a prance!!! Tons of hand motions!!! Sassy mannerisms as much as possible!!!

When you talk to him try and act as fem as you can something like “OMG!!! Ughh!!! Daddy you’ll like never believe this, I was totally shopping for lingerie and like couldn’t decide which one is better what do you think??? (Show him/wait for his response) “OMG!!! Yasssss!!! That is like soooooo cute daddy!!!”

Act cute, talk cute, be cute and your daddy will actually adore you!!! 💞💞💞


r/Sissy • • 8h ago

Sissy Achievement! wore my first plug to the gym NSFW

11 Upvotes

I finally built up the confidence to wear my plug to the gym 😖 i felt so slutty feeling it press up against my p-spot during my sets, watching all the men walk around me I wish one of them would catch me in the locker room and just fuck my sissy hole senseless~

My underwear had a huge wet spot from all of the precum leaking from my clitty... I can't wait to go back with a bigger plug next time 🤭


r/Sissy • • 2h ago

Need Help / Advice Fellow sissies, I need some advice! Being horny comes with consequences!!!! NSFW

4 Upvotes

Heyyy everyone! 💕

So, I'm dealing with a bit of a dilemma right now. I'm extremely horny and want to cum sooo badly, but there are two things holding me back.

First, there's PNC (post-nut clarity). Every time I cum, my mindset changes afterward, and the things I'm excited about beforehand can suddenly feel completely different.

Second, I've noticed that I seem to get new pimples or skin breakouts after I cum. I don't know if there's an actual connection, but it's frustrating either way!

Now I'm stuck here, really wanting to cum but worrying about dealing with both afterward.

So, fellow sissies, have any of you experienced either of these things? How do you deal with PNC, and have you noticed any skin changes after cumming?

I'm open to any advice, suggestions, or personal experiences you have to share. I'd love to hear what works for you! 💗


r/Sissy • • 3h ago

Sissy Achievement! I just ordered my first set of panties and thongs NSFW

5 Upvotes

I'm so excited but nervous 😖 I bought some lace panties and thongs and I can't wait to try them on, I'm scared I don't look as feminine in them as some of the other sissies I see on here 🥲 but they're so sexy and I can't wait 😮‍💨


r/Sissy • • 4m ago

Discussion Honest question from someone who’s been there: Do you ever feel regret, or feel like this lifestyle is just what you've become? NSFW

• Upvotes

Hey everyone. I’m writing this because I want to have a genuine, deep, and respectful conversation about the psychological side of this lifestyle. I’m asking this with absolutely no judgment, but rather as someone who understands the feeling.

I’ve been in this world myself. I’ve bought the clothes, the toys, and I’ve even been tempted to take things a step further into the real world. However, I’ve managed to maintain control over it so that it doesn't become the main focus or identity of my life. But it's hard, and I often find myself thinking about what it would be like to just give in and fully adopt that lifestyle. Because of that, I want to ask you guys about your experience.

A lot of people seem to start down this path through a very specific cycle: it begins with consuming porn and sissy content, which slowly shifts your mindset. Over time, it evolves from a fantasy into reality—buying clothes, toys, and adopting a mindset of wanting to be a submissive or a "girl/slut." For many, it starts during a time of being antisocial, lonely, or lacking a solid friend group, and this lifestyle provides a quick sense of validation and community. It feels like the only place where you truly feel like you belong.

But eventually, it can completely alter your identity, making you question your sexuality or gender. Looking at it from the outside, it can look like an addiction that slowly changes how a person thinks until they lose control over their original path and completely transform who they are.

Whether you are just starting out or have already fully committed to this lifestyle and let it become your identity, I really want to hear your honest thoughts on the psychological impact of this journey:

  • Do you ever feel the same internal struggle I do, or did you just let go?
  • Deep down, do you feel like this was just the only way you found to feel like you belonged to something, but in the end, it feels too superficial?
  • Even if you say you love and enjoy it today, do you ever feel lonely, useless, or regretful about how much it changed your mindset?
  • Do you wish you had maintained more mental control in the beginning before it became your main identity, or do you feel genuinely fulfilled by where you are now?
  • Even if you deny it to others, do you secretly feel or think differently inside? Do you just continue with this lifestyle because it’s who you’ve become now, and you feel like turning back is no longer worth it or even possible?

I really want to understand the balance between the pleasure/validation of this lifestyle and the deeper feeling of isolation it might bring. Thank you for reading, and I’d love to hear your honest thoughts.


r/Sissy • • 3h ago

Sissy Achievement! Anal makes me feel complete NSFW

3 Upvotes

I just started fucking playing with myself after a long time. The moment my dildo went inside me I just realised that I only feel complete this way. The discomfort in the beginning. The adaption. The feeling of fullness and the sudden rush of endorphins I get by hitting my sissy button. I always feel so dirty fucking myself but it is sooo worth it and just shows me my real worth. Would a real man would talk like that? Of course not! Anal is like the ultimate sissy maker and I just love to be a sissy for a cock💕


r/Sissy • • 7h ago

Question how do you guys explain sissy to your partner who haven't heard of it? NSFW

5 Upvotes

i remember when i first got brave enough to explore my sissyhood in real life, I met an older guy on a gay subreddit. When I entered his bedroom, I was so nervous that I asked if I can watch some porn on his laptop.

He looked up gay porn for me and I told him those aren't for me, and proceed to look up sissy hypno. He was so confused because he thought i was just gay but I explained that I am not actually gay, and I could see his cock going soft haha, I tried to save it by explaining sissy to him but I don't think i did a good job, i was new to the whole concept myself after all.

Anyway, I ended up showing him a few of my favorite sissy hypno and we watched for 15 min to calm my nerves before I started sucking him off like the video told me to do. He liked it so much that he asked me to pause so he doesn't cum too early, and asked me why am I watching seemingly straight porn (to him it was just video of girls sucking cocks), if I am into guys. I didn't want think at the moment so I just played the anal training sissy hypno and asked him if he wants to chat or if he wants to fuck my hole.

Overall a great experience, but afterward I did wonder how I could've better explained it myself, like an elevator pitch that explains sissy to him. But nowadays i probably won't find a gay hookup that don't know what sissy is anyway.


r/Sissy • • 22h ago

Discussion Dressing for the maintenance man NSFW

60 Upvotes

Has anyone ever dressed up for a maintenance appointment?

I have a maintenance worker coming to my apartment this weekend and I'm really tempted to dress a little. Nothing inappropriate, I'm not talking about opening the door in a full lingerie set lol. I've been considering wearing leggings for the appointment or if I don't have the courage for that then wearing something sexy under my boy clothes.

I don't pass facially, but I have a girly butt that looks really good in leggings. I also have some really tight panties that would smooth out any bulge in the front. I like the leggings idea because they are normal items of clothing that wouldn't be inappropriate, but they definitely show off my ass and make me look feminine. Idk though I get so nervous thinking about it.

Anyone have any experience with this?


r/Sissy • • 19h ago

Question What’s one thing you’ve always been too scared to try… that you secretly hope a Mistress will just make you do? NSFW

25 Upvotes

Is it sucking your first cock?...swallowing your first mouthful of cum?...or making you wear chastity and pink butt plug when you have a big presentation to do at the office? I want to hear all of them! 😌✨


r/Sissy • • 2h ago

Sissy Personals Corrupting a straight white boi NSFW

1 Upvotes

I’ve been watching sissy hypno and porn for a bit now and think it’s time to start my sissy training. Looking for some to show me the way weather it’s me getting dick down rough or a gentle start DMs open I’m 19 M


r/Sissy • • 6h ago

Discussion Does only wanting to do oral make you more or less of a sissy? NSFW

2 Upvotes

Hey gurls! Recently I bought my first dildo and had a great time with it overall, but I much preferred the oral side of it to the anal side.

It takes less prep time, less cleanup, and I honestly love giving head, even if it's just on a dildo for now. So would only giving head make me more or less of a sissy?

Genuinely curious what other people's thoughts are on this because I feel like it makes me more of a sissy? Simply because I feel like it's disregarding my own pleasure (even though it feels sooooo good giving head) which is a major point of being a sissy, to please the cock not urself.

Curious to hear your thoughts!!


r/Sissy • • 9h ago

Sissy Personals Looking for an online dom to slowly corrupt and permanently change me from a normal guy to his closeted sissy slut NSFW

3 Upvotes

35m in Australia, developing interest in gay and sissy content. I want an online dom who basically slowly corrupts and hypnotises me until I progressively become a secret sissy slut - make it so I can only get off to gay or sissy porn, I’m regularly playing with my ass, showing off for you doing tasks, crossdressing and maybe even one day servicing strangers for you. Make it so my “real life” becomes just a cover for my real sissy self

Open to how we do it but I think edging and JOI will be best way to start you make me edge to the porn you choose regularly until you rewire my brain, tell me how to pleasure myself, give me tasks etc and we go from there


r/Sissy • • 7h ago

New Sissy Your first time trying on panties everr!! NSFW

2 Upvotes

dont get embarrassed we all started like that<3

what was your first experience with panties? whose were them and how old were you when it happened for the first time? what triggered the need to wear them? do you remember the first pair u tried on or your favorite pair growing up? have u ever been caught (or almost) in them??


r/Sissy • • 8h ago

Question How Many Time Can I Cum to BBC Before It's Stupid Not to Suck One? NSFW

2 Upvotes

It's been a few thousand...

I think about it a lot but lose the urge completely after I finish.


r/Sissy • • 21h ago

Tips for Sissies Interesting "hack" for Sniffies... NSFW

23 Upvotes

Not really a hack per se, just don't know what else to call it.

The other night I was browsing through sniffies. Not because I was able to actually meet up...I was just bored. At about 11pm I called it quits and went to sleep...buy my computer was left on. It was plugged in and my settings are set to keep it on and awake always. I was so tired that day I didn't even notice, not even the light from the screen kept me up.

When I woke the next morning I had a TON of messages that accumulated overnight. I guess it's obvious, but the bulk of cruising is happening late, late at night. Most of them were picture-less with nothing in their profile. Their message was the always sexy "hey". 😂

But a few were interesting enough that I might have followed up if I were actually able to play.

Next time a chance to play comes around I'm gonna do this on purpose the night before. Hopefully I'll get a stack of would-be suitors that I can browse through the next day...and if I'm lucky...set up a hook up for later that night.


r/Sissy • • 13h ago

Discussion Leaky Locktober NSFW

5 Upvotes

Any other sissies leaking non stop? This is not sissie’s first locktober but sissy has possibly never been this horny, so close to finally achieving a sissygasm!


r/Sissy • • 7h ago

Discussion Back in college, I was known as the community mouth. I started transitioning from mtf at 18. NSFW

0 Upvotes

I always knew I was a sucker for cock. Back in college I blew almost every guy I knew. I was on so much estrogen and oxytocin it made me horny all the time


r/Sissy • • 7h ago

Need Help / Advice How to prepare for my first date NSFW

1 Upvotes

Hi babes,
Long story short, I have my first date next week with a daddy I have been chatting with. I’m aleeady kinda stressing about it and would like to get your insights to go through with it and how best to prepare for the date. I will be changing at his place, as I’m not confident yet to go out as a sissy.
All tips and tricks are welcome! ❤️


r/Sissy • • 1d ago

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

140 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 • • 12h ago

Discussion I think this would be fun NSFW

2 Upvotes

Sometimes I think about how fun/sexy it would be if I got in a relationship or had a dommy mommy who would lock me up and randomly make me wear a strap-on and while i am restrained on the bed ride the strapped dildo until she came. I know this is probably pretty common however I just also wouldn't mind if if was a guy fucking my brains out then having his wife ride the dildo or something like that.


r/Sissy • • 1d ago

Discussion What was your sissy awakening moment? NSFW

23 Upvotes

You know the one, that moment where something just *clicked* and you thought "oh... OH." 😳

For me it was the first time I saw myself in a thong and bra and I thought "she's been in there the whole time." I never looked back 🥰

What was yours? I want to hear everyone's origin story 💕