CrossDressing Stories

A Adventures in Lifeguarding Story
Brian comes "out of the closet"/"off pool deck" and it changes his life.

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

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

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!

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

The Hitman is a professional assassin and master of disguise. To carry out his next hit he has to dress as a woman to get close to his mark who has a proclivity for transvestites. Feedback and comments are always welcome.

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.

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.