How did you discover you were a sissy?
I started pretty standard with liking women and watching regular porn. Then at around age 17 I was talking with some guys while changing after gym class and for some reason the topic changed to homosexuality, and one guy mentioned that everyone will have at least one gay dream in their life. Weird and probably fake statistic but when I went home and jerked off I was suddenly thinking about his muscular body, his lips, how it would feel to touch his chest and his penis, and I came.
Fast forward and I am now regularly having sessions thinking about men. But I know they are all straight, so I struggle to imagine them wanting me as a boy. At this point I have been to a lot of parties and have seen how the girls dress, short dresses, skirts, sometimes with a visible thong or push up bra. I start imagining myself wearing this when I'm dreaming about guys.
Then eventually when I'm looking for porn I basically stumble upon caption porn, and eventually sissy captions. The fap roulettes inspire me to go futher, as they often tell you to wear specific clothes, use toys and where to cum. I start fingering myself, then use carrots and cucumbers. I also try tasting my own cum and giving myself facials.
Eventually I muster up the courage to buy a multipack of colorful thongs online. I end up wearing them basically any time I'm alone. I then finally buy a real dildo, every orgasm I've had up until that point pales in comparison. This is how I am meant to be satisfied.
Eventually I get my own place, and due to covid I get to spend all day in lingerie, with a cute dress or my maid uniform over it, I buy multiple more dildos that can vibrate, squirt and with suction cups so they can be floor or wall mounted.
And thats how I became a sissy. Don't really want to take it further with a real guy, but might eventually buy a sex machine.
How about you?