Hey everyone!!! Let’s play a game. Every sissy that regularly posts here(you know who you are) say hi and share a short story of things you’ve done to explore being a sissy!

I’ll go first:

When I was younger, I met an online dom. Tbh I don’t remember much about them now, they claimed to be a woman and I remember receiving some nudes but tbh, I didn’t care. They were into me sending them videos of me using dildos, and they were the one that first asked me to do anal training. I’d have to send a different training video every day, and sometimes they’d give further instructions on how they wanted me to use my hole.

I have… no idea who this person is. None. I’ve degraded myself in so many filthy ways, for this complete stranger all because I wanted to feel validated in using my ass and feeling like a girl.

Anyways, that’s all behind me now, but it definitely instilled a love of instructions/tasks as well as sending videos of myself. So I’m sure it’s had some ramifications.

  • 3hrtd@lemmynsfw.comEnglish
    3·
    1 year ago

    Not sure if I count as a regular poster, but what the heck :)

    I actually haven’t done much… yet. I’ve kind of always been obsessed with the idea of being feminine, but only recently started to take action on it. At first it was just because as a guy, I was always told I had a decent ass, so I tried wearing women’s leggings to see if they were different to compression tights that guys sometimes wear to the gym. And I was quite surprised to see that my ass looked significantly larger and better in women’s leggings. Maybe it’s something different on how it holds the shape up and rounds it off.

    Then I ordered some g string panties online and tried wearing them under the leggings, pulling the string up and above my hips so that you could tell how slutty it looked.

    Since then, I’ve experimented with things here and there. Being able to see the bulge of a chastity cage under skin tight leggings is hot, and I’ve even managed to stain the front of the leggings a few times because I just dripped so much. I’ve tried playing with my ass a few times, but haven’t been able to have the best experience yet.

    I’ve always imagined/dreamt of having massive tits, and I’ve tried a few breastplates, but haven’t been able to find any that are a right fit for me yet.

    Guess I’m only just getting started! :)

  • chloespanked@lemmynsfw.comEnglish
    3·
    1 year ago

    Hi all ☺️! I started exploring anal play and chastity around the time I discovered how to masturbate with my penis (ie, puberty). I’ve never really had a sissy experience with another person - I’m working my way towards that. It’s taken me a long time to understand and accept my sissy urges. I identified as bi when I was around college age and fooled around with a couple guys. I remember getting fucked by one - it wasn’t great sex - but afterwards we were in a takeout pizza joint having a late night meal, and I felt his come leaking out my ass. That really turned me on. I remember a guy calling me pretty and buying me a flower once - that made me blush. It took me a while to realize that having sex with a guy would be 10x hotter for me if I could present femme as opposed to as a guy. Relationships with women haven’t been great. Both me and my partners expected me to have typical heterosexual kinks, which I don’t, and I’ve been in places where I’ve used my sissy fantasies to help me finish during vanilla sex with a girlfriend. I’ve enjoyed being 1 of 2 male couples sharing a room for hookup sex. And I remember the first time I put a plug in my butt (right after buying it from a sex shop) and walking around with it. I think I’m slowly figuring things out and learning the ropes. I’m hoping I can start hooking up as a sissy this winter 🥰

  • stockings_n_summer@lemmynsfw.com
    2·
    1 year ago

    Hi! This sounds like a great idea 🩷

    I don’t really have a sissy name but feel free to call me summer on account of my username. Summer is present teehee.

    I got into cross-dressing pretty young and started anal play about the same time too. When I got old enough I started buying myself toys, sucking cock & occasionally bottoming 😁

    I’m lucky enough to have a girlfriend that doesn’t mind me wearing makeup and stockings and plugs. I really enjoy complimenting other people’s outfits and helping other girls on their journey.

    In the future I want to dress more fem and also get more buttplugs hehe. My dress collection is sorely lacking and that must be fixed.

    Also, WallsToTheBalls is a hilarious username 🤭