Jester4fun

I’m a passable smooth CD that loves fun! Love to be manhandled:) Just like a lot of femboys I was not into guys at all in high school. Exact opposite actually, I excelled at football and was quite the ladies man. After high school things began to change dramatically. I accidentally found Shemale porn and was blown away how passable and sexy they were. After a long battle with depression and the lose of a close friend of mine I tried things I never have before. I began to buy women’s clothing slowly as I found I was highly attracted to lingerie, mostly stockings and garters. The first time I completely dolled up I knew I’d never come back. My first sexual activity with a man ended with an orgasm that I’ve never come close to getting with a woman. Hope you enjoy my stories and feel free to reach out to me, I love meeting and chatting with new people:). Follow me on kik:Jester4funtime Twitter: AmFemboy

Jester4fun Stories

Below you can find the complete collection of stories by Jester4fun.

My full time journey

18 Apr 2025 comments

The story of how and why I went full time feminine

9.3 (22) 776 Reads 7 Min

CD Hotel sex

3 Oct 2024 comments

Sissy CD takes dick in hotel

9.4 (104) 8359 Reads 8 Min

First time at a gloryhole

26 May 2024 comments

True story of my first time visiting a gloryhole

9.3 (125) 8110 Reads 6 Min

Crossdressers first BBC

26 Feb 2024 comments

My first BBC

9.2 (211) 15700 Reads 8 Min

My Vegas trip

24 Apr 2023 comments

My real Vegas trip:)

9.4 (195) 4079 Reads 10 Min

First time sex as a CD

21 Apr 2023 comments

My dream come true

9.3 (192) 7385 Reads 5 Min