r/Sissy • • 16h 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 • • 5h 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 • • 14h ago

Question Experience with SissyLover Academy? NSFW

19 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 • • 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 • • 15h ago

Sissy Story Hard Problem NSFW

14 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 • • 15h ago

Question All-natural sissy community? NSFW

6 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 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 • • 17h 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

8 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 • • 1h ago

Question Can you turn gay? NSFW

• 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 • • 20h 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 • • 3h ago

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

37 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

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.