CrossDressing Stories

When I woke up and eventually dragged myself out of bed on this New Year 's Day, I hadn't planned on writing a short story. But that's what happened, and here we are. A young man in his early twenty's, desperate for companionship, unexpectedly finds some company when he goes swimming. The meeting leads to the young man finding out more about himself and his desires.

In a highly sexually charged tale, Jesse, a diminutive Asian teenager who is discovering his sexuality, gets help from his BFF from middle school, Sara, to dress as a woman. As Jesse's true calling emerges, a spontaneous blowjob sets the stage for him to become the woman of his dreams. As more characters weave their way into the story, they both have a night they will never forget.

A virginal young guy is rebuffed during his first experiences with a girlfriend. Then he gets involved with an unusual older neighbor. This is set in 1981.

The fourteen-year-old Filipino towel boy at a New Orleans French Quarter male brothel, Mama Rosa's, gets initiated with the rubber hand-tipped scepter of a former Mardi Gras king.

A guy and gal meet each other at a club, and sparks fly between the two of them. But each of them has a secret they are keeping from the other.

I was inspired by the opening premise of Oliver Twist’s excellent “My double life as a whore,” where a surprise meeting in a hotel bar leads to many other things, to recount my own true story of my recent hotel bar adventure.

Desperate to own a wedding dress, Craig decides to buy one second hand from the local classifieds. Things don't quite go as he envisioned they would.

Young Meg is certain she has found the ideal way for both she and her father to pay their way in the world. Unfortunately, it involves robbery on the King's highway and that is a "Hanging" offense.

Cross-dressing comes in all varieties.