Gay Strapon Stories

60 results
Orientation
Length
Source
Infinite Scroll

An Unexpected Pleasure Ch. 01

by whitestream44 on Aug 18, 2017
Gay Male

My girlfriend and I had been dating for a few years, and the sex had gotten a little slow. We were still doing it a lot, but it just wasn't as exciting as it used to be. Then one night, after a few drinks, that topic came up, and it turned out she was feeling bored with our sex life too. Even though I had been thinking the same thing, that is not something a...

House-Sitting with a Homosexual Pt. 05

by GayTripper on Jun 18, 2018
Gay Male

Here it is, the final chapter of House-Sitting With a Homosexual! Yes I know, the actual house-sitting portion of this series ended a long time ago but the name has stuck and what can I say... I enjoy a bit of alliteration in my titles. This was the first series I ever published at Literotica and it's great that I finally get to bring this one to completion....

I Want You to Come with Me

by johnson69 on Sep 10, 2018
Gay Male

As we progressed in the relationship there were certain stages at which we were becoming more intimate that I felt compelled to reveal some of my peccadillos. Since there were some significant ones, I told Judy that she could walk away with no hard feelings. For me it was very liberating to not have to hide parts of me that would certainly come out. It would...

Boat Ho Ch. 19

by rckplsky on Sep 15, 2017
Gay Male

"I hate duty," Alex said as she slipped out of bed. "Why do you say that," he said as he looked at the alarm clock. "It's six on Saturday," she said as she pulled her utilities out of the closet. "Must suck," he replied, "what time is Huff gonna be here?" "Around eight or so," she said as she walked over to her brother, "he's in the duty section before m...

Please Fuck My Ass

by atitagain991 on Sep 15, 2017
Gay Male

Once I hit my late teens I knew I had to try cock at some point. When I was drunk I craved it, especially hung over. I wanted to be dominated and didn't put it together that I was a bottom. There were a few instances where I would watch gay porn and masturbate. This caused some intense cumshot orgasms. My first attempt to play with another guy was organise...

First Time Fucked

by tinywhiteboi on Aug 18, 2017
Gay Male

It's a long story but I had by now been the chastised slave to my former Mistress for over 6 months. Over that time I'd been conditioned to be more and more subservient. She seemed to take particular pleasure in humiliating me in front of others, especially her friends. Most Friday nights she'd have a gathering at her house with 2 or 3 friends. I would serv...

Anal for the First Time

by JohnLeslie on Aug 18, 2017
Gay Male

This is a true story that happened a couple of days ago. Of course I changed the names of the people involved but otherwise this is everything I can remember. My name is Paul. I am 40, tall, athletic, handsome and masculine. I consider myself straight in that I am rarely attracted to guys and can't see ever having an emotional connection with a guy beyond...

Fulfilling a Fantasy

by eagle122999 on Apr 3, 2019
Gay Male

Sex with a man. It's a fantasy some straight guys have but few act on it. For quite a while I have thought about going through with it. I didn't really have a fantasy guy picked out, except for one aspect... his cock. My fantasy guy had a big cock. I figured if I was going to go through with the fantasy I would go big or go home. I would talk to guys online...

My Neighbor the Cop Ch. 02

by tonyl65 on Sep 25, 2017
Gay Male

I found myself walking across the street from my neighbor's house with the taste of cum in my mouth. I walked into my house, not my house, but my wife and I's house. I was married, my wife is out of town for the weekend, and after helping my neighbor with some yard work I end up sucking his cock and being his pussy boy. What got into me, other than my neighb...

Fun Down Under Ch. 01

by watchdwag on Sep 15, 2017
Gay Male

I recently enjoyed a bout with a local bloke that is perhaps worth reading. My name is Ted and I have a small home improvement business in Melbourne. A few months ago I got a call from a woman who inquired about adding onto her house. She said she and her husband were considering adding a deck to their home off the kitchen and inquired about the costs. As we...