Shemale Fuck Male Stories

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Mistress Coco School Wayward Boys

by tawnysuede on Sep 14, 2017
Transsexuals & Crossdressers

Where Boys Become Girls, Whether They Like it or Not by Mistress Tawny Suede assisted by slave Holly Introduction In Which We Meet Rich Bitch Kimberly and Domineering Mistress Coco Kimberly Caldwell's head thrashed about on the silk pillows; a cry of ecstatic pain escaped her luscious lips as she cupped her heavy breasts, her crimson fingernails ra...

How I Met My Shemale Pt. 02

by Eroticalover1968 on Sep 25, 2017
Transsexuals & Crossdressers

I sat motionless and stared at her as she swirled her thumb around the end of her glistening member. It was very well lubricated with her sex fluid. "Hey you! Don't you know it's rude to stare?" she shouted, breaking the trance I'd been lost in. "Oh, sorry," I said as I glanced up at her furtively. She was murmuring something to herself while drawing her s...

Jabba's Shemale Slave Pt. 02

by mkh78 on Oct 8, 2019
Celebrities & Fan Fiction

This story is from the imagination of the writer and inspired by Return of the Jedi. I have used Huttese words in some parts. These are not of my own. *** 1:30 am. Tarno and the Twi'lek shemale prostitute he found and subsequently bought from the brothel's owner, were now quickly speeding across the Tatooine desert. He considered spending the night at a...

Dark Life

by Samuelx on Sep 14, 2017
Transsexuals & Crossdressers

Kiara looked at herself in the mirror. She liked what she saw. A tall girl with long black hair and pale blue eyes. Her skin was light bronze. She stood five feet eleven inches tall in her bare feet. She had just stepped out of the shower and finished drying herself up. Kiara was a pretty girl and she could hold her own against most of the other females out...

2016 Literotica Reader's Choice Awards Winners

by Literotica on Sep 16, 2017
BDSM

The stories and authors below were chosen by our readers as the best of 2016, in voting which took place here. Though these are not the only wonderful authors and stories on Literotica, they are worthy of praise and recognition. Thanks to all of the writers for providing us with hours of hot reading, and to all of the readers for your input, support, and a...

The Gym Ch. 4

by Kip Carson on Sep 14, 2017
Group Sex

John arrived at Kate's house at 6:50 pm. She answered the door in a very tight fitting short dress. "Damn, you look good" John told her. "Sorry I'm so early, but I was so excited about tonight" he added. "That's fine, I'm always ready early" she said. "And you look pretty damn good, too" she added. She eyed him up and down. He was wearing black dockers, a ni...

SheMale Sirens Ch. 02

by WhiskeyIsGood on Sep 18, 2017
Transsexuals & Crossdressers

Chapter 1 has received good reviews, so here is part 2. Part 3 is still being written, but it is going to have more back round info on the Siren's, and a few more characters as well. Should be up soon after this one. Whiskey ***** The day I first decided I had to leave my home in New York was the day I turned eighteen years old. I was tired of everything,...

Anal Fuck Toys

by RedragonLite on Jul 12, 2020
Fetish

Join the CHYOA Fan Server and discuss this story and many more with the community: https://discord.gg/DQn3bVH If you want to support me and my work, please check out my Patreon: https://www.patreon.com/redragonlite This is the first and last chapter out of context. Here the premise will be explained, and all characters you may choose from are listed, each...

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College Shemale babysitter

by tomf15 on Sep 15, 2017
Transsexuals & Crossdressers

Disclaimer: All characters are 18 and over. Jessica pulled up in front of a large house at the end of the street. She looked down at the text; 1278 Backstreet. "This is the right place," she thought. Jessica was a fairly normal, attractive college girl. She studied hard, partied on weekends, and liked to work out. There was one thing that separated her f...

'''CHAT'''

by Ssrd33 on May 10, 2019
Transsexual

Hi Jhon!, Hi Mike ... I answered lazily ... like all the days, my life had become very routine and repetitive, at home my wife does not serve me as a man or husband, I think I was dating I sneaked in with another man, but at this point in my life I did not care and the children made a mess everywhere. I wanted to escape this prison from which I felt trapped,...

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