Gay Transvestite Stories

71 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

My Little Rose Ch. 01

by UndertakerKiryu on Aug 18, 2017
Gay Male

I lay sleeping in a modified coffin, feeling the wonderful silk against my pale aged skin. The cushion beneath me was a fluffy cloud which my head rested on. I enjoyed sleeping in coffins, the dead had it so good. The bell clanged. Someone had entered my alternative store and was in rather a hurry. No customers had appeared as of late, so I was not expecting...

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!...

Just A Lift!

by Scotsdude on Aug 18, 2017
Gay Male

This story is complete fiction…but fun I hope! "Not going mate. Soz." Kevin said. I was well pissed off. "Why the hell not?" I asked. "I can't afford the tickets." Great, so that was that. Creamfields for me was off too! Kevin was the one with the car, I was the one paying the fuel, but now Kevin wasn't going, I couldn't get there! "Mate, you can always...

Malta Intervention

by sr71plt on Sep 14, 2017
Gay Male

It was Giorgio's own fault. Really. Sandy and I were quite happy to do our part. But if Giorgio hadn't been such a snotty little bitch, we would have never done him that way. For three glorious years Sandy and I had thought we'd found paradise on the Mediterranean island of Malta. We'd managed to live well on his stipend from the British Royal Navy and were...

Learning

by billie-asub on Aug 18, 2017
Gay Male

It was hot that day. I was supposed to be at work, of course, but everyone needs to play hooky now and again. It had been a long time since I'd taken a day off, so I didn't feel the least bit guilty about calling in sick...and now I had the whole day to myself. My wife was at her own job, I was on my own. My first thought was just to go for a drive, so, tha...

Rest Stop Slave

by buttcheeks777 on Sep 14, 2017
Gay Male

I'm finding myself becomming dirtier and nastier in my sexual appetite. The dirtier the better lately. This dirty instance happened to me halfway between Sacramento and Yreka, CA four years ago and I still get a hard on thinking about it. My company sends me all over the US on business, and they insist that I drive so I can take my samples with me for clien...

Condo for Sale

by KeithD on Mar 3, 2020
Gay Male

For Sale: $675,000. 1 bed, 1.0 bath, 546 sqft condo at Hill Street, Unit A. Do you want to own a home in a great location in San Francisco? Here is a terrific opportunity on Hill Street in the heart of Noe Valley and the Castro District. In this 1 bedroom, 1 bath Condo in a 4 unit building with your own private deck. Close to transportation, many great shops...

Trying Something New

by Scotsdude on Aug 18, 2017
Gay Male

I was always an avid reader. Now I had broken up with my girlfriend, I had more time to read. I shared a flat with my mate James. He worked for a local software house, whereas I was a student. I was home most of the day and he came home late. Both of us were in the same position however, his girlfriend had left him to go to America not one month ago. About...

The Gay Version Of Sex In The City

by verotika on Aug 18, 2017
Gay Male

My name is Kyle, your typical gay male living in New York City. Although, I haven't always lived in The Big Apple. I'm originally from small town called Marion in Iowa. My family has lived there for generations. I never really thought about moving myself, until my father caught me and my "best friend" fucking like wild animals in the boat house. You have...

Make 'Em Scream Ch. 01

by oreolover13 on Sep 15, 2017
Gay Male

The cab ride from the station to this little suburb was a lot shorter than I expected. Compared to the train ride that is. Spending three nights on two trains was not my ideal way to travel. But this is the life of a broke college kid. Before he graduated my best friend Ryan said for spring break I should come to his house. He was one year older than me and...