Transsexuals & Crossdressers Stories

15,868 results
Orientation
Length
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Infinite Scroll

Casey's Submissive Journey Pt. 15

by corduroysissy on Aug 28, 2018
Transsexuals & Crossdressers

When he walked into the playroom he saw Robin sitting in one of the chairs drinking a beer. Sonya turned around and pointed to the other chair. "Sit puto." Debbie did as told and his boner made a very obvious tent out of his skirt, it didn't bother him though because it matched Robin's pants. Sonya left without a word and Debbie picked up the drink on the...

The Role Players Pt. 08 Ch. 01

by hollygurl29 on Aug 13, 2018
Transsexuals & Crossdressers

DISCLAIMER: This is a work of fiction and all characters represented here and in any additional parts of this story are all over the age of 21. This tale involved crossdressing, bdsm & role playing. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. The main characters in this tale are as...

AliExpress and Sissy Downfall Pt. 07

by His_fag_wife on Apr 9, 2018
Transsexuals & Crossdressers

Please for goodness sake don't read this story if extreme use of submissive males by dominant males and dominant females offends you. This is pure fantasy and at the darker end of the spectrum of stories on Literotica, please do not read if this is not your sort of thing. Otherwise I hope you enjoy the spiral of depravity. ***** Charlie was alone in the ro...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

Forbidden Fruit

by notbreckenridge on Apr 16, 2018
Transsexuals & Crossdressers

Author's Note: Got another one here for you folks. All the people involved are eighteen or older. This in no way reflects any real people or groups. Any inaccuracies or errors are my own. It's a fantasy in a slightly more realistic world than I sometimes write in so there are no elves. I know sheesha is another word for the hookah, but I've always heard peop...

The Elephant in the Room Ch. 02

by MicheleNylons on Apr 17, 2018
Transsexuals & Crossdressers

Chapter Two: Elizabeth Elizabeth's first memories were of being poor; that is to say her mother was poor and alone having been abandoned by her husband, Elizabeth's father. Her mom cursed her ex-husband and men in general but she schemed and connived and using her good looks, her intelligence and her considerable sex appeal she landed another man, a better...

The Streamer

by neoview on Mar 21, 2018
Transsexuals & Crossdressers

This story will take a different turn from my usual sci-fi road. A little modern world view on what is happening on the other side of your screens. As usual everything is fictional. ***** Wednesday, 21 December 2017, 21:59 "Alright, time for my evening stream. Gee, I can't wait." The clock turns 22:00 and a beautiful figure appears in front of a camera....

Man Disciplines Sissy Ch. 04

by LanaBehave on Sep 25, 2018
Transsexuals & Crossdressers

The fitness-center shower area had three separate tiled shower stalls, with another plank-type bench stretching across their front. I stood between the bench and the middle shower, waiting for him. For Ray. For Daddy. I looked down at myself, and my little cock was hard. I was waiting for Daddy, and he was going to wash me, and show me something. Until t...

The Perfumer

by JonThomas_ on Jan 7, 2018
Transsexuals & Crossdressers

Hello all, this is your ever so humble, nearly omniscient narrator. I'm back with the somewhat unusual story of Pierre "Pepe" Le Pew. He's a self made man. For the last ten years of his life, he's built a small but profitable perfume company. He's been somewhat of a mad scientist, single minded in his pursuit of the perfect fragrance. It would smell great...

Seduced and Hoodwinked Ch. 04

by walterio on Jan 7, 2018
Transsexuals & Crossdressers

SHOPPING, MASSAGES AND SEX On Tuesday morning Darin and the ladyboys passed on sex and after breakfast they went shopping. They picked up supplies first and then went to a boutique and picked up some new clothes and accessories. They stopped for lunch afterward and at the restaurant many eyes were on the three beauties. Darin was sure that people were wonde...