CrossDressing Stories

Ben and his sister are running from the law after robbing a bank in Pittsburgh, Pennsylvania. They go west by train to Kansas City, Kansas where their money runs out. They start walking, sleeping under bridges as they travel slowly toward Wichita. A fancy carriage stops next to them and the man driving asked them if they would drive for him. They end up taking the man’s name and pretend to be man and wife. Ben now Henry, becomes a well to do lawyer in Lawrence, Kansas. Read to find out how!

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.

Where does a guy go to find another guy interested in some "MAN" sex? A short discussion of where and how. Informative but no real sex. Just some instruction. (Not for homophobes)

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.

Dennis becomes infatuated with the girl in the blue denim skirt who sits on the low brick wall running along the path inside Aston Park. He knows that his infatuation with her is troublesome and that he should just ignore her but he just can't resist her allure.

Sometimes, things bear repeating

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?