Shemale Gangbang Stories

5,318 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Commissions

by Rekki on Oct 27, 2020
Miscellaneous

A combined ensemble of all the public commissions I made in 2020. All the mentioned characters are 18 years of age.What's next? Red on White - Asami Sato x Blanca Vasquez Futa-TF Kimono The Spartan Finals Tracy and the Greenhorn Barbaric Love Lordran's loyal whore What's next? Red on White - Asami Sato x Blanca Vasquez Futa-TF Kimono The Spartan Fin...

Open in Reader

Joel Gets Caught by His Wife

by Downforeverything on Sep 18, 2017
Transsexuals & Crossdressers

This is a fictional story written for a fan about their sex life. If anyone else has a story they'd like written for them about fact or fictional events feel free to message me. As always please leave comments or constructive criticism so I can make your pleasure better! * It was Monday afternoon. Joel had taken the day as an opportunity to work from home...

Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...

Lingerie Night at the Sauna

by montrealjane on Sep 16, 2017
Transsexuals & Crossdressers

Montreal is a liberated place, and its sauna (AKA bathhouses south of the border) are no exception. Sauna St Hubert, one of the smaller ones is particularly creative, with theme nights including lingerie night every tuesday. For my first time, I did not take my lingerie, but I liked what I saw. Around 20 gurls dressed, some passable and dressed to the nines...

The Virgin Tranny & the Bride Ch. 08

by yano on Sep 25, 2017
Transsexuals & Crossdressers

My transvestite friend Roberta writes to tell me that recent surrender of her boy pussy to her Master was, sadly, not for love but as a means of gaining embarrassing video footage to use as sexual blackmail. Master John is now teasing Roberta and she is about to embark on a new career as a call girl and prostitute. She writes: With the lining removed and m...

Craving Shemale Cock Ch. 01

by jeritza on Oct 22, 2019
Transgender & Crossdressers

I stood nervously on the dark cobblestone alley street, in front of the unmarked door, running through the possibilities in my head, speaking under my breath. I was thinking of all the events that led me to this moment - the perverted path I had gone down. This is it. This is finally happening. No turning back now. Dear god, no turning back now. *** I was...

Summer Prix198Something

by FerociousFernweh on Sep 15, 2017
Sci-Fi & Fantasy

The following story takes place in an alternative history. All STDs were cured in the 90s and rampant population growth is controlled by year-long birth control for both sexes that's administered every time you renew your ID. Most sexual taboos are no longer a moral battlefront save for bestiality and pedophilia and sex in general is seen more as entertainme...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...

Pam's Shemale Experience Ch. 03

by majicman21 on Sep 12, 2017
Transsexuals & Crossdressers

It was late morning on Saturday. Tanya was sitting at the kitchen table, wearing a satin robe that she had brought from home, left open to reveal her nakedness. The daily newspaper was in her hands, Tanya leisurely reading it as Pam knelt before her, slurping greedily along her balls. They were slick with saliva, gleaming like polished ebony. Her fingers wer...