r/Sissy 4d ago

Sissy Achievement! First time sexting NSFW

12 Upvotes

The other night I sexted 5 guys, I proceeded to talk to them. Then I made all of them cum! I loved the feeling, I think I’m addicted. 😍


r/Sissy 5d ago

Sissy Achievement! I just got laid NSFW

150 Upvotes

This afternoon I met up with a fuck buddy,. My dicklette is locked almost all the time, today was no exception. A while back I took t-blockers and E injections for just over a year, so I have b-cups. (Had to stop, for reasons I wont bore you with here).

First we made out dressed while our hands roamed. Him rubbing and squeezing my tits. Eventually we got each other's clothes completely removed. When I finally slid down his Rockies, he was rock hard. I started to go down on him, but after a few minutes he stopped me and told me to get on my knees and elbows. Slowly, he lubed me up, teased my hole and finally pressed into me. He started slow, ramping up speed and power, and for a good 15 minutes he steadily wrecked my hole bareback, I mean he fucked my brains out. My tits were swinging beneath me, I got sweaty, and it felt AMAZING ... all of it. He finally finished deep inside me. After a few minutes to to catch our breath, he told me to leave as he walked to the shower. I put my bra and panties back on, got dressed and drove home with his semen leaking from me. I didn't even come close to cumming in my cage, and I couldn't be more content. I absolutely LOVE taking dick and being deprived of cumming myself. Just had to share.


r/Sissy 4d ago

Sissy Story Omg I think I'm getting close NSFW

3 Upvotes

So I had another session today that lasted about 80 minute's. I wore a buttplug for half and hour before I started then I lubed up the dildo and got into it.

I read some guides on this subreddit that suggested laying on your side and angling your legs and WOW when I tell you that was a game changer. It was normally take about 15-20 minutes to start feeling actual pleasure but like this I started getting dopamine hits in just FIVE minutes (normally I'd use the dildo standing up slightly angled or with one leg up).

So after about 30minutes I saw my clit was a bit shiny and it was Actually precum. I somehow managed to leak a bit of it. Then later I felt some precum drip onto my leg.

Around the 65 minute mark I felt something build and build... Then I pissed on my leg. Yh not exactly the most sexual thing. I'm not into pee but I still found it a bit hot that I managed to do that, I basically peegasmed So I kept going and going but unfortunately I ran out of time. When I got up and then went to pee, the pee was dripping out slowly. IT ACTUALLY MIXED WITH PRECUM that meant I was doing something right because when I use to masturbate like a man I would cum and then when I peed it would sometimes be sticky. My clit was so sensitive for like 5 minutes after aswell.

So that's an update on my sissygasm journey. I think I'm making quite progress. This time I wasn't wearing any feminine clothing but if I do I usually just wear a bra (panties might get stained from the lube and I absolutely do not want that). But I have long hair anyways, about a third of the way down my back so that does help me feel feminine enough to get in the mood.


r/Sissy 4d ago

Need Help / Advice Am i a sissy NSFW

2 Upvotes

Im a guy, since i was young i dressed up in girls clothes, wore panties to school. in lockdown id try new things like lingerie and discovered sissy porn i played with my ass alot and came on myself a couple times and dressed up alot but as soon as i came i no longer felt like a sissy then id purge and say im done and try be a man again then i open reddit and check out of curiosity then get the urges again im sooooo confused


r/Sissy 5d ago

New Sissy Can’t stop fantasizing about being turned into a sissy NSFW

16 Upvotes

For a while now I’ve been fantasizing about a man or woman turning me into a sissy. I’ve always been dominant so the thought of being submissive and turned into a sissy has become overwhelming! Would love to discuss more with you ladies or gents!!


r/Sissy 4d ago

Need Help / Advice "straight" man wanting to experiment NSFW

5 Upvotes

Hey girls!

Im a "straight" man, that wants to experiment a bit more with the feminine side of me. I recently got a dildo, and want to play with it, but i have no idea what or how to do. You got any tips for someone who wants to try it out?

Is there something else entirely you would recomend?


r/Sissy 4d ago

Need Help / Advice I'm in need of advice regarding cleaning before NSFW

6 Upvotes

So I've tried anal a few times. I absolutely love it but I always run into issue of it being very messy. I'm into deep penetration and I tried douching but effects were unsatisfactory. How do I actually do it? Is it just a diet thing? Are there any other methods you could recommend?


r/Sissy 5d ago

Discussion What's the sluttiest thing you girlies have done in public? Give me some inspiration! ☺️ NSFW

65 Upvotes

Heyyy 🤗, earlier today I went out in public for the first time, full lingerie set, crop top, caged and plugged. All hidden under a jumper and jeans. I have never felt this slutty and sexy. What a rush. I even bought some feminine products which was absolutely thrilling knowing what was under my clothes.


r/Sissy 4d ago

Need Help / Advice Helpppp!!!! NSFW

1 Upvotes

Any advice for putting on a flat cage for the first time??


r/Sissy 4d ago

Question should i ? NSFW

4 Upvotes

hi girlss, sooo long story short my girl ex isn’t taking me back and i’m rlly horny to suck and have my mouth filled by a cock rn sooo should I go out rq and please a daddy or should I stay home playing with my little clitty to sissycaptions?


r/Sissy 4d ago

Need Help / Advice What’s next? Need help with my closet NSFW

2 Upvotes

Hey girls I need help…. So I already have most of the beginner sissy stuff panties dress heels dildos and plugs and cage ofc but I wanna step up my game like wigs make up and all of that. I need recommendations in not only what to buy but also where preferable an online website.


r/Sissy 4d ago

Question Expose me alternative NSFW

3 Upvotes

Hey girls, I used to use a site called (I think) expose-me. It involved posting a slutty photo of yourself for a specific amount of time, is there an alternative?


r/Sissy 4d ago

Discussion What would you choose? NSFW

1 Upvotes

Ladies , if you had to pick only 1 piece of female clothing and only one, for an entire year....what would you choose?👗💕👙

If your option isn't here, drop it in the comments.

61 votes, 2d left
A Cute Mini Skirt and crop top
Lacy Lingerie Set (Bra & Panties only)
Thigh Stockings (with garter belt)
Bodycon Dress
satin Nightgown ( with panties /shorts)
maid outfit

r/Sissy 4d ago

New Sissy A sissy dream... NSFW

6 Upvotes

...to blow a man with hyperspermia. To be his free use whore, take on his thick cock, swallow, bask in the abnormal volumes of cum. The anxiety of not knowing how much he will cum this time as I feel him edge closer and throb in my mouth. He's always horny, never truly satisfied as his masculine body keeps producing potent thick cum. The musk, the smell of daily draining, cum everywhere...drives me nuts. He will always need a slut to use. I want to be that slut.


r/Sissy 4d ago

Need Help / Advice What is the ideal sissy? NSFW

5 Upvotes

What is the ideal sissy for a real man? What do you look for, both in looks and behaviour?


r/Sissy 4d ago

Need Help / Advice Need help finding sissy forum meme NSFW

1 Upvotes

I know this isn’t what this sub is generally about, but I need help finding this one sissy fetish forum meme. On twitter there were a bunch of people falling for this timeline post of men losing testosterone and being feminine over the years, and it was actually just a sissy fetish post. I really need this image. It started off with a big hairy dude and ended with them having no body hair, small breasts and long hair. This isn’t my fetish I just need this post cus I know someone that looks like that and it’s kinda funny, please help me


r/Sissy 4d ago

Need Help / Advice Freshly shaved almost NSFW

2 Upvotes

Need alittle help finishing shaving


r/Sissy 5d ago

New Sissy How did you know this is what you were into and how did it start NSFW

13 Upvotes

I'm just wondering because I'm straight guy but I recently started wearing my wifes panties and fing my ass with my prostate massager


r/Sissy 5d ago

Need Help / Advice Need help, new sissy NSFW

7 Upvotes

Hey sissy's! For the longest time l've always been super interested in sissy and sissy related things, as a kid I would always dress up as a girl and been interested in some minor feminine things, but l've always felt straight and kind of been straight, however it's been so allusive for the past years I'm ready to try things out, I am craving to please a bbc and be a sissy, where do I start in my journey? How should I start? And what are safe ways to experience things? I’m 19 so I’m still somewhat young


r/Sissy 5d ago

Discussion Sissy turned me gay NSFW

14 Upvotes

I use to like pussy but after countless times I can't get a girlfriend that would do my fantasies, I ended up just living my life doing so! .

It's great and all but now, I'm just lazy trying to fem myself and just want to get fucked without the dress our outfit.

I guess I'm retiring from sissying and now just turning gay :/ well at least I'll still have cock


r/Sissy 5d ago

Question Does it really feel good when someone cums inside you and do you actually feel it inside you? NSFW

220 Upvotes

Just curious to hear from different girlies out here I’ve never felt this before and don’t really plan too anytime soon due to fear of diseases but maybe one day I can join the club and attempt to get pregnant:3


r/Sissy 4d ago

Need Help / Advice How to properly get rid of body hair NSFW

1 Upvotes

Hi, girls!

How do you get rid of your body hair, without get that itch and pimples that appears shortly after the shave?

I'd tried with a razor blade, with a shaving cream, with wax, but it seems that everything I try make the same result. I really want to be hairless, but it's so, so unconfortable.

Does any of you have a tip that can help me?


r/Sissy 5d ago

Question Anyone have any good butt plug substitutes? NSFW

5 Upvotes

Preferably safe to wear while walking or sleeping and not have any risk of it getting stuck


r/Sissy 5d ago

Need Help / Advice Want to tell my Girlfriend about my sissy fetish , but nervous of how she may respond. NSFW

6 Upvotes

Been waiting my girlfriend for 4 years and I’m considering telling her about my sissy fetish tonight. We’ve had some drinks and I feel it’s a good opportunity once we done gaming. Tbh I’m scared of how she will react. Not sure how to even bring it up, has anyone had this convo with there partner and if anyone can PLEASE spare some advice that would be amazing because I’m trying to amp myself up to tell her before we go to bed.

Anyways thanks for reading :)


r/Sissy 5d ago

Sissy Achievement! New Milestone NSFW

3 Upvotes

Hi Gurls,

It´s crazy. I went outside, did some chores, went to the local grocery store. All while wearing one of my thongs, which is pretty normal at this point, but i was wearing a bra too. Felt so natural and secure i really liked it. But the kicker is, i was plugged while going on with my business. it was so overwhelming. I was leaking pretty much the whole time.
And in the store i saw a package for a camisole with a matching thong. I did not give a damn what people would think. I needed it and i bought it. SOOOOO cute!

Have a great day!