1154 - FETISH FRIDAY: Jack is a Fluid Crossdresser who is Totally Into Prostate Play

Strictly Anonymous Confessions · Jun 27, 2025 · 1h 5m

Jack is a fluid crossdresser who is totally into prostate play and he called in to talk all about it. Tune in to hear him discuss all the details including how and when he realized he was into wearing female clothing and what he enjoyed about it at first, when he got into trans porn and exploring anal play, his first hook-up he had with another crossdresser and exactly what went down, his stash he was accumulating and where he gets everything from, how he told one of his girlfriends that he was into pegging and how she reacted, the first guy he hooked up with and exactly what went down…