My Wife With A Shemale Sex Story Stories

361,501 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

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...

How Dicks ended up in My Mouth Ch. 01

by ret123 on Sep 19, 2017
Transsexuals & Crossdressers

My name is Joe. I am a married, successful business man with a pretty wife. I lead the life of an upper middle class guy. I grew up in a small Texas city and had a great childhood. I was a football star in high school and college and dated lots of attractive women. Most people would say my life is ideal. However, I have some secrets. The story begins when m...

Cuckold's Descent

by syncbush on Mar 27, 2020
Cheating Spouses

Thank you to those of you who have liked or taken the time to comment/message me. I really appreciate the feedback. Feel free to add additional chapters, suggest ideas or leave comments. It is great to get ffedback and encourages writers to continue developing the stories. And special thanks to the Admins for making this story of the week! Really appreciated...

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...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

Open in Reader

The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...

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...

'''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,...

Open in Reader

My Wife, the TOP ONLY Malay Shemale

by yarracuda on Sep 19, 2017
Transsexuals & Crossdressers

Hi all, my name is yarra (not my real name perverts!!) and I am a proudly married matured male, now 57 years old. My wife, 52 is a (or was a) biological female technically, been married to me for the past 24 years. Let me tell you my fantastic and totally out of this world story. Flashback to 24 years ago, that is the 1989, when i just reached my 30'ish a...

Father-In-Law Shemale Adventure

by greyhound_guy30 on Sep 16, 2017
Transsexuals & Crossdressers

My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last moment I decided to take the day off. Since the girls were out, I...