CrossDressing Stories

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!

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.

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.

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

Paul is a closet tranny who meets regularly with other transvestites for platonic get-togethers. He usually stops to change in a seldom-used rest room at a remote truck stop so that she can arrive at the get-together already transformed into Pauline. Tonight however, the restroom is a convenient place for some bikers to take a leak before they go over to the truck stop bar to drink beer. What will the bikers do when they find a foxy tranny hiding in one of the stalls?

Femdom in the Victorian era. A male in a male dominated society finds thar Women are really in charge.

Jack has been working vice for nearly a year as a prostitute named "Holly", much to the amusement of the other cops. When things unexpectedly heat up with a rookie, however, it begs the question...Who's really undercover?

A mildly exaggerated true story on how I moved my wife from repressed religious girl to a confident BDSM switch.