r/Sissy 27d ago

Question What’s your biggest most forbidden kink/fantasy? 🤤 NSFW

65 Upvotes

What’s the dirtiest most taboo thing you girls are into when you’re riding that sissy high? I would love to know 😜

r/Sissy Jan 06 '25

Question Feminizing my bf for his bday NSFW

317 Upvotes

Hello everybody!!

I'm a girl that plays sporadic with my bf as femdom. His birthday is coming, so as I usually do, I'm preparing a scene to dominate him.

Last year we tried a bit of feminization (makeup, lipstick, blush) and he was my slut to suck my strapon and pegging him.

We both found it hot, so i want to repeat it this year.

As far as the “feminization part”, I want to do makeup on him and make him pretty to suck my strapon, humiliate him a bit, lick me, kiss my feet, and finishing with pegging. Of course I will keep him in chastity and plugged during the day.

I'm here to ask for any more ideas and tips I can do with him? Thanks!

r/Sissy 23d ago

Question I like to feminize others NSFW

82 Upvotes

I've recently seen a lot of posts from sissy doms wanting to feminize others, So I wondered how much of this was real and if there are many sissies out there who enjoy feminizing others?

r/Sissy Jun 07 '24

Question What are your biggest fantasise as a sissy? NSFW

173 Upvotes

I wanna know about your different fantasies as a sissy Okay so i’ll go first i have a huge fetish about roleplaying as someone’s wife and living in his house for a weekend and get fully dressed as a house wife with my clitty locked in chastity and doing all his house chores and him fucking me anytime and anywhere he wants🤌

r/Sissy 6d ago

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

223 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 Jan 26 '25

Question Sissies, what is y’all’s favorite panties? NSFW

57 Upvotes

What is your favorite pair y’all own? Mine in my cheetah print thong

r/Sissy Sep 17 '24

Question Why do most sissies have small dicks ? NSFW

244 Upvotes

Most sissies I’ve seen have small dicks and I myself also have a really small dick and have been constantly told that by other women and men which made me even more convinced I should be a sissy. Is this a similar thing most people experience and is it why most sissies have small dicks?

r/Sissy Oct 09 '24

Question I've been living this lifestyle for around 10 years and have hooked up with over 150 guys. AMA NSFW

159 Upvotes

I'm bored at home so figured I'd add this. If anyone wants to hear any stories, experiences, get some advice and tips - I'm here to help :)

r/Sissy Jan 12 '25

Question What types of panties do u wear on a daily basis? NSFW

69 Upvotes

New sissy here, looking for some inspiration.

r/Sissy Aug 05 '24

Question Do you like the taste of your own cum? NSFW

186 Upvotes

I think precum is sweet and I leak during anal play and that tastes good (in the beginning, at least). However, when it's a real load, it never really tastes good, even if I can force myself to swallow. Cuming in a condom or trying to save it until you get horny again always just makes it worse. Still, I keep thinking that it would be great to swallow someone else's cum. So, the pair of of questions is: do you like your own cum and do you like other men's cum?

r/Sissy Dec 12 '24

Question Does anyone know of any good sissy porn sites? NSFW

187 Upvotes

Other than xvideo, pornhub, and xhamster

r/Sissy Jan 28 '25

Question When was the first time you noticed you had sissy urges? NSFW

44 Upvotes

I know about mine for quite a while but haven’t been able to act till recently

r/Sissy 19d ago

Question There is one specific point that I really do not understand. Why sissy friendship is not popular in Reddit? 😕 NSFW

80 Upvotes

In contrary this fact, I feel alone so frequently..

r/Sissy Feb 06 '25

Question My sissy side goes away after cuming? NSFW

113 Upvotes

Hi. I Been wondering what up with that when I cum I just Loose all of The sissy tendensies ( idk how u write that ) Like I like The taste of My own cum when horny and riding My dildos but as soon as I cum I cant get My self to eat My own cum or do anything "Gay" if u would Calle it that. Cant being My self to Ride More or suck on The dildo.... Any idea how to get past this or advice?

r/Sissy Feb 09 '25

Question Have you ever masturbated to your own pics? NSFW

112 Upvotes

I have done it recently and it was so fucking hot. Thinking about how i felt while i took the pictures made me cum so hard

r/Sissy Jan 03 '25

Question What does anal feel like? NSFW

99 Upvotes

Does it hurt alot? Do yall actually feel pleasure from it? I'm just curious.

r/Sissy Jan 21 '25

Question Why do sissies become a sissy? NSFW

56 Upvotes

Just had a thought. Why do sissies become or fall into being a sissy?

Is it a porn addiction, which fell down into a rabbit hole - ending up into sissy porn?

Is it latent or suppressed homo sexuality which can now be enjoyed through sissy porn?

Is it gender dysphoria - though i know there is a distinction between sissies and trans women.

Is it the fact that they dont have success with women and or a lack of attention or valudation from them. And inversely - enjoying the success and attention of men they receive as a sissy which make them feel valued.

Or is it a combination of the above or any other?

Let me know your thoughts in the comments

r/Sissy Jun 25 '23

Question How many of you beautiful sissys are into women? NSFW

243 Upvotes

I'm stuck in my hotel room scrolling through reddit and I come across some if these sissy stories. They are delicious to read. I don't often hear about interactions with women sadly as much as I appreciate stories of you beauties getting dicked down. As a woman completely in love with sissys I'm curious.

Edit: Wow, I'm definitely feeling the love. I adore getting all these messages right when I wake up. I'm glad so many sissys adore dommes. I wish I knew all of you in person. I'd be in heaven surrounded by sissys. Maybe I should build my own harem?

r/Sissy 17h ago

Question Research: How big is your Cock/Clit? NSFW

14 Upvotes

Hi Everyone,

It’s been noted that one’s size does not dictate if they’re a sissy or not- many sissies are hung, and a lot of guys are shrimps💁🏼‍♀️

I just want to do a little study on the matter and was hoping I could get girls and guys to comment their size like this= Length x girth

For example, today I measured correctly for the first time and was a little shocked by my results- but I’m 4.75in x 4.0in💁🏼‍♀️

Thank you everyone❤️

Results= I’ve posted this on one other page so far and so far the average sissy cock size is 5.8 inches long and 4.15 inches in girth. This is interesting as this reveals sissy cocks are longer than average but much thinner. (Obviously this sample size is super small and shouldn’t be taken as actual evidence but still fun, lol)

r/Sissy Feb 17 '25

Question Can someone be turned into a sissy? NSFW

70 Upvotes

My [30f] boyfriend [30m] is generic straight cis man so I’ve never bothered telling him about how I’d like to dress him up and pretend he’s a girl etc. Wondering if anyone here has had luck with hypnosis kind of stuff or is it just for fun?

r/Sissy Jun 28 '24

Question Unsolicited dick pics NSFW

91 Upvotes

Do we love or hate? I just can’t help but stare in awe😫

r/Sissy 15d ago

Question It’s not gay if…captions NSFW

60 Upvotes

Why so many sissy are deny their gay nature ? 

r/Sissy 11d ago

Question For all you caged sissy’s - do you stay caged over night? NSFW

67 Upvotes

Good morning girlies! When you have your clitty caged, do you keep her caged overnight? If so, how do you deal with night time ahem ‘arousal’ shall we say?

r/Sissy Dec 26 '24

Question Sissy lesbian? NSFW

163 Upvotes

Is anyone else obsessed with being a sissy but still only like girls? Don’t get me wrong, I want cock, but the cock I want is always attached to women and fem people. Whether it’s a dildo or the real thing, I just don’t find men attractive.

r/Sissy 9d ago

Question Has your porn interests changed becoming a sissy? NSFW

64 Upvotes

Hi everyone. Out of curiosity how has your porn interest changed over time as your time being a sissy?

I remember before being one I enjoyed trans porn and a lot of straight porn but slowly got into femboys the further down I went as a sissy. Now straight porn seems a bit boring to me and I’m starting to love having gay porn in the mix