CrossDressing Stories

A casual comment made in a young man's past about his sister comes back to him in so many delightful ways.

Four sailors are marooned on a Pacific island hoping against hope to be rescued. When they are joined by the survivor of an airplane crash their hopes soar expecting that a search and rescue mission will find them. Will Bobbie Bingham be their lucky charm? As it turns out Bobbie as a secret. He is a she.

How I came to give my first blow job.

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

Shaun is called through to his sister's room to help his sister and best (female) friend in a phone app challenge. No sex, just touching.

Alex lives with his mother Julie and refuses to get a job or to help Julie pay the rent and household bills. When Julie sees pictures of Alex dressed as a girl she sees that Alex has potential for meaningful employment, even though Alex might not want the job.

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

Sometimes, things bear repeating

Mothers can be maternal, or infernal and despicable. Here, a good mother earns a life of love, lust, and happiness, while older children of bad mothers escape—including sisters whose parents wanted to traffic them overseas. Through blood and marriage ties and many twists and turns, these nine characters have the happy endings (in every sense) they deserve. Contains hydrotherapy and transvestism (a woman in hiding, who adopts a temporary male identity and clothing).

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.