CrossDressing Stories

If you have read my other stuff here, you know what to expect; This is more of the same. I’ll leave it at that, as the journey is as much fun as the destination.

When Mike Harris stole two point seven million dollars in cash from his gangster boss, he knew that his life had changed forever. He has to get away and hide; his best disguise was to dress as a woman, but this had some implications that he hadn't though of. Dressed as the transvestite Michele he was sexy & attractive and men wanted to take advantage of her

A sister helps her brother dress up like a woman for a costume party.

The Collector collects girls and takes them to his estate where they become Novices, to be trained in the arts of sexually satisfying their Masters. When they graduate they become Acolytes, living a life of sexual servitude to the Order of the Circle who use them for their sexual gratification. We follow the indoctrination of Mary, a girl from a poor background and Charlotte, who comes from a rich family and who is the first transsexual girl to be indoctrinated in the Order.

A T-girl has her first ever meeting with a man and it opens a whole new world for her. From a public carpark kiss to a full bedroom experience in one afternoon. A day of firsts

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!

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.

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

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

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.