Gay Shemales Stories

28 results
Orientation
Length
Source
Infinite Scroll

The Barber

by balbrash on Aug 21, 2018
Gay Male

During my junior year in college, I lived alone in a small city apartment. My entire social life consisted of short, random conversations with students in my classes, or coworkers at my warehouse night job. I didn't mind. I was lonely, but not that lonely. I wanted a girlfriend. Someone to love. I played video games. I jerked off 2 or 3 times a day. It had...

The Myth about Big Black Cock

by BBC_Envy on Aug 18, 2017
Gay Male

***Warning*** This story contains content of a homosexual interracial nature about my first but not last time with a man. Particularly a black man, and while the rumors are mostly true, this is not one of those times. If homosexual and/or interracial content offends you, please feel free to back out now and search for other stories that suit your fancy. If t...

Not So Boring Afternoon

by agpatch2 on Aug 30, 2017
Gay Male

This is a story about one day while I was home from college on Spring Break. All my college friends had gone away for the break, but I didn't have enough money so I just went home. The problem was that none of my friends were on break for the same week, so I was bored out of my mind. I spent most of my days lying out in the back trying to get a tan or sittin...

Amsterdam Weekend Ch. 02: Tom's Story

by Sean943 on Nov 18, 2019
Gay Male

My name is Tom and this is my story, of my first visit to Amsterdam; it all started at our usual Friday night pub meet in the centre of Manchester. I always looked forward to it as the guys there treated me as an equal. The usual heated discussion had started. This time was what we would do if we could get away together for a weekend. I said; let's all go...

First Cock Came From Old Friend

by Trinni69 on Aug 31, 2017
Gay Male

It was Saturday and I had nothing to do so I decided to go for a drive. I got into my car and headed out of the city in no particular direction. After driving for a while I realized I was close to Jim's house. We have been great friends for years but have not seen each other for a long time. I decided to surprise him by dropping by unannounced and see if he...

I Turned Myself Out

by drmweaver705 on Jan 29, 2020
Gay Male

All characters are 18 or over. ***** My journey must have begun with my discovery of porn. When I was eighteen, I discovered a trove of porn magazines hidden out in the abandoned shed of a derelict and condemned house near my childhood home. This was the first time in my sheltered life I had ever seen anything like it. The magazines varied from soft nudit...

A Night to Remember

by IrishJamesHot on Aug 18, 2017
Gay Male

A fair number of years ago, I was about 19 or so. I had recently finished school and got myself a handy job. Making money and being young, I of course began heading into town (Dublin) on the weekends for some very enjoyable nights out. This night, was one to remember. I had been drinking with some friends in a pub. Last orders were called at bout 2:00a.m....

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...

An Executive Learns His Place

by Luctari on Sep 14, 2017
Gay Male

My phone dinged, an email from Tim, guy in our IT department. What the hell was he doing sending something to my personal address? How'd he even get it? I opened the message. Luke, I have an important matter to discuss with you that I don't think you'd want to talk about in the office. Meet me at the Motel 6 near the airport tonight at 7pm. Tim Who the...

Big Bot, Sex Hot, Breeder Gets Laid

by danielblue on Aug 18, 2017
Gay Male

Tyler was really glad to find a new job, after being unemployed for a couple of months, but disappointed that he had to work with two macho, homophobic guys. Trouble was, the only work he could get was in a factory and the office he shared with the two guys was way out in the sheds, away from the main buildings so the badass breeders were the only people he...