First Time Crossdressing For A Man [TM]

Hello everyone,

This is a crosspost r/gaystoriesgonewild. I’ve been a lurker here and have a few stories of my own that I could share but never have. I got a pretty good response on the above sub so I figured I would post here too! ? what follows is copied from the original post:

Now I know that the whole sissy fetish isn’t for everyone in this sub, or even really that accepted in the gay community at times. That being said, for me, the appeal to the sissy fetish is much more about the humiliation aspect of the kink than anything else. As this story will explain, I never knew how much I really enjoyed being so submissive.

What follows is entirely true, and I will never forget it:

A little about myself. I was 20 years old in college at the time. I was about 165 lbs and 5’9. I had always enjoyed dressing up from an early age. When I was much younger, I vividly remember stumbling upon transsexual porn and becoming instantly infatuated. I found myself wanting to dress up and wear sexy lingerie. When I finally moved out of my parent’s house at 18, all bets were off. I had roommates, but would almost instinctively close the doors to my room every night and slip into some sexy clothes and play with myself. I went to local sex shops and bought tons of outfits over time, dildos, heels, pink chastity, the whole gambit.