Gay Shemale Fucks Guy Stories

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Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

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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...

To Serve You. Pt. 02

by mkh78 on Feb 10, 2020
Gay Male

This is a just a fun fictional story from the mind of the author. All characters are over 18. Enjoy. It is now fifteen months since we met and I am still my boyfriends "slave". Our first date brought us to this odd master and slave relationship. Although you may think it's "sick" for a 34 year old man to "own" a 27 year old man, we are both consenting adult...

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...

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...

My First Cock in Years

by Bostonsnowball on Aug 18, 2017
Gay Male

As I was driving home after a weekend away, I started thinking about going to the Paris Theater. I was feeling very aroused since I hadn't jacked off in several days, I needed to feel a pair of lips on my cock. I had been there before and always had some guy slobbering on my cock within 15 minutes of walking through the door. I parked as close as I could, t...

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...

The Long Trip

by TheBlackStallion on Mar 6, 2018
Gay Male

Editor's note: this story contains scenes of non-consentual or reluctant sex. This is my first story, please give me some feedback. Parts of this story of true, some of it isn't. I'll leave you to decide * I've been a young sailor for almost two years now. We've been at sea for almost 75 days. Tomorrow we will be pulling into Thailand. It's been a long ri...

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...

Drunk at College

by johndovinski on Sep 19, 2017
Gay Male

*** Author's Warning: I've never written anything that's published anywhere before. I've read A LOT of Literotica stories and it took a lot of nerve to just write something on here. This story is a bit of an extended fantasy about what I wanted to happen at a very specific time in my life, but names and details have been changed to protect the innocent. Than...