Crossdressing Bet Stories

66,523 results
Orientation
Length
Source
Infinite Scroll

The Bet Ch. 01

by RandyCross on Nov 6, 2018
Erotic Couplings

** My first attempt at a longer piece - do let me know what you think! ** ***** I was always a patsy for being sent to conferences at short notice, the price I paid for being single, childless and pet-less. This particular conference, my boss reasoned I could drop everything and head to Liverpool at short notice, with a couple of hundred quid as a sweetene...

Mom & Me Ch. 35

by Yechesem on Apr 15, 2020
Romance

Billy's First Date With Rachel Nicholson As I was walking down Broad Street I remembered I needed to go by the florist shop to pick up Rachel's corsage. I turned on Wright Avenue and made my way down to Main Street where I turned west and walked another three blocks before entering Marybeth's Flower Shop. A sales lady approached and asked me if she could...

Timid Neighbor

by shutterpsb on Mar 9, 2020
Mature

This story is a revision of a story I posted to Literotica several years ago. This story is a work of fiction and contains no references to any real persons or events. *** Tapping on the patio door caught my attention. I shouted for Rick to come in. I looked up at his footfalls and smiled at the teenager. The boy had a parcel in his arms. "It came, John....

The Bad Boys Club - Half Time

by JimAner on Oct 6, 2020
Fetish

This bondage and discipline story is a CFNM tale about women spanking their husbands. It is also a story that celebrates domestic discipline where the female, NOT the male, is the disciplinarian. If the thought of a woman using a paddle on her husband's behind upsets you, or if a story about men having to act as sex objects and sex toys offends you, do not r...

Unlocking Tally Ch. 03

by NerdyNymph on Sep 14, 2017
Erotic Couplings

"So here's the plan, Tally," Rei said. "After the show, you can run interference with the boy while I try to get my mack on with the ginger hottie." At least she had a plan. All I had was an objective. When Rei had invited me out to this concert, I'd thought for sure that it would be the next stage of my whole "broaden my sexual horizons" initiative. What...

My Girlfriend and the Quarterback

by clarkoverns on Sep 12, 2017
Exhibitionist & Voyeur

Everyone in this story is eighteen or older. I was a nerdy kid back in high school, awkward and shy and too book smart. Needless to say, I wasn't very popular, especially with girls. I spent most of my time hanging out with my few friends and trying not to get bullied. The most popular kid was the football team's quarterback, Todd Brooks, who was cruel...

Ripe Fruits Ch. 03a

by kamal12345 on Sep 18, 2017
Mature

I would like to suggest please read before this ripe fruit ....03 * "Now, Zeshan, I trust, you won't tell anyone." I shook my head slowly and replied. "I can't believe it myself. Who could I tell?" "We'd better get dressed now. My daughter might be waiting for me," Mahal said as she got up, kissed me on the cheek, then frantically got dressed and hurried...

Seducing Coach Ch. 01

by greaterimp on Sep 26, 2017
Group Sex

Chapter 1: Dee and Bobbi Bobbi and Dee were sitting around in Dee's house, bored on a summer afternoon, unable to think of anything fun to do. They had graduated a month earlier, and while they were happy to be rid of the drudgery of school, they missed the structure it had given them. They had both been athletes the entire time, and the absence of the phys...

Who Needs Humiliation Ch. 07

by K.K. on Sep 19, 2017
Loving Wives

Chapter 7: The Games Continue On Monday Carla was no more friendly or unfriendly then she had been since the first day of class. She would talk to me about work but nothing else. I had noticed one thing that day. During the lecture portion of class that morning anytime I answered a question or made a comment in class I could see that it bothered Carla. She...

Alice's Ass

by JoeDreamer on Sep 25, 2017
Anal

'I am going to kill Carl!' I thought for the hundredth time. I wanted to jump up and run screaming from the restaurant, but I remained seated and kept a smile plastered on my face. It wasn't easy. I probably didn't need to bother. I doubt the girl across from me would have noticed if I let my true emotions show. She was too busy telling me her life story t...