CrossDressing Stories

My mother, who abandoned my father and me, returns. This is how I broke her into being my pussy slave.

The story of my first gay sex as a mature man with a mature man.

Arthur is the gardener at a girls school, and spies on the girls until he is caught by Sylvia, the delicious PE teacher. This story is about how Sylvia turns Arthur into Angela, and makes Angela wear girl clothing, sleep in the girls'dormitory, and pleasure all those needy girls. Sylvia uses a strap and a cane on her girls, and Angela experiences those also.

A young male college student notices that a coffee shop is only employing pretty young women. He disguises himself as a girl to get a job in the establishment but soon discovers that the girl he has become must surrender her virtue to remain employed.

I am a transvestite and it has taken me years to become adept transforming into a woman. It amazes me when I read so-called autobiographical stories about some guy who suddenly decides to and suddenly transforms from hairy man into a sexy stunning woman. I have written this story as a tongue in cheek dig at these stories. To read the story, just select any of the options a, through d, to put together your very own autobiographical "Grab Bag" story.

A man awakes from a coma only to find he has selective amnesia. He doesn't know that he has a secret life. He is a closet transvestite. At first repulsed by the idea, he can't help exploring his secret life. What is it like to dress as a woman? What is it like to feel feminine? What is it like to suck a man's cock!

14 year old Billy is home alone with Quinn, his dad's 16 year old boyfriend. While Dad's away, Quinn has a fun idea to share with Billy and they boys begin a hot relationship of their own.

In 1957 Michael Nyland is one of the few male nurses working at Chelmsford Memorial Hospital. Matron Amanda Holliday and Doctor Lovejoy have uncovered his secret fetish for lingerie. One day he wakes up in one of the private wards tied to the bed dressed in silky full-slip, satin cami-knickers, sheer hose, high-heels; and makeup professionally applied and hair coiffured. Nurse Nyland has no choice but to satisfy the Doctor but is totally unprepared for life as a transvestite prostitute.