u/Shapeless-papercut

How to be brave enough to try a real hookup?

So, I’m a shy sissy. I’ve done a lot of solo stuff, and I started posting online a few weeks ago, but I still haven’t decided to actually try sucking my first dick or getting fucked.

When I’m aroused, there’s nothing I feel like I wouldn’t do, but when I’m not in the mood, I start to hesitate. It’s not like I completely lose interest, I just... don’t really feel like it.

I don’t wear chastity for whatever reasons, but I wonder if it would help me stay in that mindset without giving myself the chance to chicken out at the last minute.

Help, gurls 😩💗

reddit.com
u/Shapeless-papercut — 9 days ago

I just want to get it off my chest, girls.

So I've been crossdressing and playing solo for more than 4 years now. Tried a lot of dildos, small ones, bigger, even the ones with fuck machine. Both mouth and ass. A lot of buttplugs, anal beads. I used to be dirty and naughty, locking myself in the closet, pretending I'm in some sort of dark gloryhole and sucking off dildos, covering my face with fake cum and own spit.

But lately, it all seems to be... not enough. Maybe because I've never reached a sissygasm. I posted my first pictures, start chatting, and lately, I cannot think straight anymore. It feels like the phase had just ended and now I'm about to become a real sissy. I'm thinking about cocks and hookups, checking the hotels and local clubs.

I'm not sure if I have the point in here. I just wanted to write this as I'm both terrified and excited.

kisses 🫦

reddit.com
u/Shapeless-papercut — 20 days ago