Gay Transvestite Stories

87 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

Made to be a Transvestite Pt. 01

by Mechman17 on Apr 3, 2019
Gay Male

The names in this true story have been changed. ***** Steve and I have been friends since our freshman year of high school. We played basketball and tennis together, were part of the same social circle, and after high school became best friends. He was part of my first (failed) wedding and I was for him. Life changed in many ways but through my 28th birthd...

Club Level Cocktails Ch. 3

by Jon69 on Aug 18, 2017
Gay Male

As I entered the patio, I thought I’d feel more trepidation. After all I thought, in the last 12 hours I’d found myself kissing a man, sucking a very large cock, swallowing cum and being fucked in the ass by a beautiful transvestite. But, much to my surprise I didn’t feel at all uncomfortable. I just had, I decided, the most interesting 12 hours of my life!...

Kane & Spencer

by amyredek on Sep 14, 2017
Gay Male

Prologue I wanted to title this book as Marcus and Spencer, but the editor, for obvious reasons, wouldn't let me. My name is Marcus Kane and my partner is Tracey Spencer. I say partner in its fullest sense, as we are both male and we sleep and have sex together. Tracey was and still is a practising homosexual, while I'm just practising at the moment, for I...

Alex in Wonderland

by Johnboy9 on Sep 16, 2017
Gay Male

Thanks in advance for any and all feedback and votes. I welcome all sent me. Please, 18 years old and up only allowed. Characters in this story are at least of that age as well, even if not indicated. I put this in the gay category though I am really not sure. Its a slow developing tale, unlike my other stories. It will again develop into a transvestite/t...

Career Guidance

by sr71plt on Aug 18, 2017
Gay Male

"What is this shit?" Bernie Wasserman grabbed up tabloids in both fists and threw them across his desk at his client, who sat slouched and defiant in a club chair on the other side of the big mahogany desk. "Those stories are exaggerated. I didn't know she was a man." "Good god, Danny," Wasserman continued to bluster. "You are playing parts of a sixteen-ye...

Curious: The Beginning

by sub5000 on Sep 1, 2017
Gay Male

1. Although I was a happily married straight guy, with a nice car and a good job I spent far too many hours looking at pornography on the internet. I don’t know why but I was always attracted to the BDSM type of websites and would download image after image of people helplessly tied up in various different types of bondage. One night, while surfing the net...

Brazil Porno Theater Jacking

by fakename1221 on Aug 17, 2017
Gay Male

A few years ago I had an opportunity to fly to Brazil for work. Once I landed (in a southern town), I had to rent a hotel room in a pretty shady part of town since the conference I was attending had filled up all the good hotels. On my way to and from the conference location every day, I had to walk by an adult theater. One of the conference days, I had a li...

Curious: Second Encounter

by sub5000 on Sep 1, 2017
Gay Male

1. Three weeks had passed since my fateful meeting with Steve, and as yet, despite his threat, I had heard nothing more from him. Since the encounter my sex life with my wife had actually improved and I was fucking her more often than ever before. Although I think this was a vain attempt to regain my heterosexuality my mind kept going back to the events of...

Pony Boy Ch. 10

by ChestersBoi on Sep 14, 2017
Gay Male

The story so far... Ben, when desperate for a little extra cash, discovered that there was good money to be made running in races as a 'ponyboy'. Despite being assured that the worst he would be subjected to would be a 'certain amount of groping' he has found that this led, inexorably, to a life as a prostitute. Moreover, Andy Mason, his pimp, along with Ar...

Pony Boy Ch. 09

by ChestersBoi on Sep 14, 2017
Gay Male

The story so far... Ben, desperate for a little extra cash, discovered that there was good money to be made running in races as a 'ponyboy'. Despite being assured that the worst he would be subjected to would be a 'certain amount of groping' he has found that this led, inexorably, to a life as a prostitute. Moreover, Andy Mason, his pimp, along with Archie,...