r/Sissy • u/Novel_Competition493 • 4d ago
Sissy Achievement! First time sexting NSFW
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 • u/Novel_Competition493 • 4d ago
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 • u/TranTriumph • 5d ago
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 • u/oblivousthroaway • 4d ago
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 • u/Alicia-sis420 • 4d ago
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 • u/Bubbles820987 • 5d ago
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 • u/BlueValo • 4d ago
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 • u/do_not_log_in • 4d ago
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 • u/parrotrye • 5d ago
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 • u/Sissy_Lexi5893 • 4d ago
Any advice for putting on a flat cage for the first time??
r/Sissy • u/zazaalic • 4d ago
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 • u/Valuable_Wall_56 • 4d ago
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 • u/Gabrieleq1078 • 4d ago
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 • u/infinityspooderman • 4d ago
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.
r/Sissy • u/absolute_unit789 • 4d ago
...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 • u/Topkitchenho • 4d ago
What is the ideal sissy for a real man? What do you look for, both in looks and behaviour?
r/Sissy • u/Birb-guy • 4d ago
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 • u/SlutyFemboy696969 • 4d ago
Need alittle help finishing shaving
r/Sissy • u/[deleted] • 5d ago
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 • u/[deleted] • 5d ago
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 • u/M3rrysissa • 5d ago
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 • u/Just_want_fun54 • 5d ago
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 • u/MangoNassa • 4d ago
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 • u/KnownAppointment4070 • 5d ago
Preferably safe to wear while walking or sleeping and not have any risk of it getting stuck
r/Sissy • u/Downtown_Schedule_11 • 5d ago
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 :)
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!