CrossDressing Stories

Molly Brown was a futanari with a problem. When she and her best friend Billy had decided to experiment with being sex-friends, things got a little weird. Although his dick was little, it still did the job! Billy went ahead and knocked her up, even while she was begging him to pull out. Now Molly had come up with a plan to get even. She would work him up to it slowly, and then show him exactly what it was like when someone refused to pull out!

A Mommy's Boy Story
Willy tries to maintain his sexual relationship with his mother as he tries to dominate others into doing his bidding. Betty likes to be dominant also. Cindy and Barry cum to play. Willy's grandfather shows up. Is Mommy in trouble now?

Cross-dressing comes in all varieties.

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.

A man is sent to prison. Surprisingly, he finds his true self.

Partly true story about the life journey of an ordinary straight guy from a small provincial town — a path as crooked as the walk of a drunk transvestite. Genre: homoerotic thriller. Setting: Moscow, present day. Reading time: about two hours.

Out of work actor Nicholas Cooper takes a job working as an assistant to a department store Santa. The only catch is that he must present femme for the role. No stranger to performing in drag, 'Nikki' arrives at Santa's Workshop to find that the store Santa is a lecherous misogynist and a lush. Desperate to keep her job Nikki has to decide if she is willing to put up with Santa's foibles and inappropriate advances. A naughty Christmas romp (in every denotation of the word) with a happy ending.

Bored with their sex life and seeking to supplement their income a husband and wife decide to enter the world of prostitution. This is a vignette in the day of a life of a high-class prostitute and explains how a married couple can live happily together while they each have sex with strangers for money.

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