Gay Shemale Interactive Stories

101 results
Orientation
Length
Source
Infinite Scroll

I Thought I Wanted It Rough...

by LonelyVirgin on Sep 14, 2017
Gay Male

Let me start off by saying I'm straight. I'm very attracted to women, but feel absolutely no attraction to men. When I was younger, I always had a fascination with anal sex. I don't know why, but from when I first started looking at porn on the internet, I was always looking for anal sex. The odd thing was, I wasn't so focused in on the penetration of all...

Delivery Man Gets A Tip

by jayce421 on Aug 18, 2017
Gay Male

Working for a local liquor distributorship you don't get to choose your routes or accounts, and being the lowest man on the Totem Pole you get even fewer options. So when I was told that my new delivery route was in the gay section of the city, I had to go. After a few weeks of getting the hang of where each place was and what times they wanted me to show u...

Thomas's Long Hard Night Ch. 01

by wanderinjoekidd on Aug 18, 2017
Gay Male

He should have never gone to the bookstore in the first place, he should have just went on home to his wife, and listened to her bitch and whine about ... whatever. But, he went, and was he ever sorry now. He had cum in his hair, on his face, in his ass, and he wasn't sure where his underwear or his socks were. And the taste in his mouth was awful! The man...

The Graduate

by kappapride08 on Mar 6, 2018
Gay Male

*My first story on this site. It's heavily inspired by the subplot between Rhys Ifans and Emily Blunt in The Five Year Engagement, with a few changes. Hope you like it!* ***** It was the second day of grad school and I still had a couple of new classes to take. The first class was CIS 505 and it was taught by an Asian professor, Bai Fan. It seemed there wa...

The Pet Ch. 01

by Gman26 on Aug 18, 2017
Gay Male

Here I am, a thirty two year old slave kneeling on the floor next to my Master in the coffee shop. Sure, I used to get strange stares, comments of all sorts, and asked to leave on a few occasions. But those were years ago. I am as common here as I am in the grocery store, the park, the post office, Master's work, and anywhere else really. I am my master's p...

The Tutor gets a Lesson

by mrsensual01 on Jun 9, 2020
Gay Male

It was September, 1972 and I was beginning my sophomore year in college. Academically I was in excellent standing and decided I could handle a few more challenging courses especially when it came to elective subjects. So, I enrolled in a Modern European History class. The class was rather small and after the first session I understood why. The professor app...

My First Gloryhole Visit

by Gregjm on Sep 14, 2017
Gay Male

I visited a gloryhole for the first time last week. I was not very experienced as I have only sucked off a few shemale escorts before, and they usually don't cum because of hormonal treatments. But I was quite curious after reading about them on the web. I chose 11:30 on a holiday Friday in a sex shop. When I got there, there were a number of cars in the lot...

It Was So Exciting

by sindyxdresser on Aug 18, 2017
Gay Male

It was about 230 am Friday night when I walked into the Crypt adult book store on 30th Street in San Diego Calif. The Crypt's usual clientele was mostly gay men, and tonight was no exception. I felt my face burning as I walked back into the peek booth part of the store. These booths had no doors or curtains so offered no privacy of any sort. There were sever...

Cum on Panties

by jakladd on Aug 30, 2017
Gay Male

Cum on Panties - Our phone sex is always so hot, you egg me on in so many ways. My wife has no idea how much I wear her panties not to mention her lingerie, stockings and dresses. We talk about what I'd wear when we get together as I suck your cock. You always have me send you pictures of me dressed in panties, stockings & high heels, telling me how perfectl...

Husband Anon Chance

by Open4Husband on Mar 9, 2020
Gay Male

There I was with a cock in my mouth for the first time ever. I was in a stall at Denver International while my wife was likely at our gate waiting for me so we could board the plane. None of that mattered much to me at that moment. I was given this chance. I was given a chance to live out a fantasy. I was given a chance to earn the approval of the owner of t...