Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

Life and Time of Lady Vargos Ch. 03

by rik581 on Mar 13, 2019
Transgender & Crossdressers

The Martin Castings Saga" is a work of erotic fantasy/fiction in three distinct pieces and is not based on any beliefs/realities or are any of the characters based on person's alive or dead. This story contains elements of b/d, s/m, forced femininity, and some explicit scenes of gay sexual activity, some non consensual in nature. The story is meant to be a p...

Life and Time of Lady Vargos Ch. 04

by rik581 on Mar 13, 2019
Transgender & Crossdressers

The Martin Hastings Saga" is a work of erotic fantasy/fiction in three distinct pieces and is not based on any beliefs/realities or are any of the characters based on person's alive or dead. This story contains elements of b/d, s/m, forced femininity, and some explicit scenes of gay sexual activity, some non consentual in nature. The story is meant to be a p...

Daddy's Sissy Staircase Ch. 03

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

This is part 3 of a 3-part series, to understand better, go back and read parts 1 and 2. Thanks for everyone's comments, this has been my first story here at Literotica, and I have ideas for many more. Please feel free to contact me with ideas for future submissive sissy slut stories! My visits to Daddy now typically involve more time than just during the...

Lady In The House Ch. 09

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Synopsis: Michele tried to use her feminine charms on the Warden at Chelmsford Prison. He rebuked her and sent her packing back to work in the prison brothel. Now Eddie has introduced her to a powerful friend of his called Davy... Can Michele seduce Dave and persuade him to help her escape the brothel where she works as a transvestite prostitute? From Part...

The Elephant in the Room Ch. 01

by MicheleNylons on Apr 3, 2018
Transsexuals & Crossdressers

Author's disclaimer: I am not a fan of 'Sissy' stories. Some crossdressed bloke dressed in taffeta and crinolines, frilly knickers, with blonde ringleted girly-girl hair being dragged along on a leash by some leather-clad dominatrix Mistress who forces him to be her sissy, spanking him and finally sticking a big plastic cock up his arse is not my forte. Tha...

Queen of Paradise Ch. 03

by ptpl_guy on Nov 2, 2017
Transsexuals & Crossdressers

This is a work of fiction. Names, characters, businesses, places, events, and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. ***** Michele stepped off the elevator and headed down the hall toward his and his wife's suit...

Tranny at the Truck Stop

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

The Perils of Pauline -- Trannie at The Truck Stop Paul sat behind the wheel of his Mustang, the windscreen opaque with heavy rain. It had been raining hard for the last hour and he was hoping it would have stopped before he reached the truck stop. He looked through the windshield as the wipers lazily swept back and forth across the glass. The sodium vapour...

It Started As A Golfing Debt Ch. 03

by StryWrter7 on Sep 12, 2017
Transsexuals & Crossdressers

This is written by me, and can be reproduced for your enjoyment, however not if it is reproduced on an Internet pay site, without compensation for me --- the writer. ________________________________________ This story is fiction. It is meant to be read by adults. Children under the age of 18, please leave. All the characters in this story are of my own ima...

Kasey's Confession Ch. 14

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

Lying in the hospital bed, hooked up to monitors and who knows what else, I just stared out in shock. It was to be expected, they said, as they explained I had been in a coma for a very long time. What they did not know was that the source of my confusion ran much deeper than just waking up disoriented after a long time "away." I had absolutely no idea who...

So You Want to be a Nurse? Ch. 03

by MicheleNylons on Sep 18, 2017
Transsexuals & Crossdressers

Assistance and Corruption Michele and Polly made love three times in total that night including a long session of oral sex. They both stripped down to their lingerie and fell asleep in each other's arms. The stimulating feel of satin and nylon rubbing against each other woke them both during the early morning; Michele had a huge erection tenting her satin p...