Gay Accidental Penetration Stories

1,847 results
Orientation
Length
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Infinite Scroll

My First Time

by ScotishGuy on Aug 18, 2017
Gay Male

I had led a sheltered and naive childhood and leaving home at eighteen was a bold move for me. I wanted to start my journey in the world, leave my childhood behind me and get a life. I got a job as a Commis Chef in an Italian restaurant in Edinburgh. Only downside was I didn't have anywhere to stay. My boss suggested the long seat at the back of the restau...

When The Cat's Away

by ScotishGuy on Aug 18, 2017
Gay Male

I sipped my beer as I sat at a table in the bar, casually looking out over Loch Lomond. I had some documents in front of me, on the table, but I was rapidly getting bored. I knew what I was going to talk about when I met my clients in the morning. I had my power point presentation ready and I was confident I could deliver it. I put a paper down and looked ou...

Cock-Sucker: 'Psycho-Sexual'

by tristantrotsky on Sep 14, 2017
Gay Male

Sometimes, going home with the wrong guy can be a mistake, a terrible mistake... * It started out a lousy day. And it just keeps getting worse. I meet him in a bar for the poor, the stupid and the stinky. I'm sat there drinking, thinking, sinking, feeling low, hungry, depressed and far from home, wondering what I'm going to be doing once tonight is through...

Not Just Anyone Ch. 03

by Cleanphil on Apr 1, 2020
Gay Male

This is a work of fiction, and any resemblance to real persons or events is unintended and purely accidental. Intended for mature (50+) audiences. All characters are over 55. This story contains scenes of incest. This story is part 3 of a series. If you haven't already done so, it is best to read Chapters 1 and 2 first to familiarize yourself with the char...

Sweet Asian Zing!

by rodneysteele41 on Aug 18, 2017
Gay Male

After graduating, I took on a position as an instructor's aid during my graduate studies year. I was amazed at how many young students not only sought out my assistance, but several even sought out my bed. One of these young men was Japanese-born Kyoshi Yuzuki. Kyo, as he liked to be called, was a very flamboyant young gay man and flaunted it quite openly. I...

On the Subway

by CyanideT on Feb 6, 2018
Gay Male

It was rush hour when Takeshi boarded the subway. The commuters, himself included, moved as a single pack to enter the already crammed car, pushing their way inside, trying to find one of the ideal positions to grab on to something. There were so many people inside it didn't really matter, he would have been hard pressed to even touch the ground with his han...

Stunned

by dkmywife on Jan 7, 2019
Gay Male

I was stunned. The divorce was final and my now ex-wife was moving out of our home and into a mansion somewhere in Pebble Beach. Luckily my finances were left alone. My wife had been seeing a guy on the side. Not that I minded that, she and I had an understanding that she could date so long as I was kept in the loop, it wasn't quite an open marriage nor were...

The Evan Fantasy

by SilkyDave on Oct 15, 2017
Gay Male

Years of Private Messages and e-mails where I always back down out of fear. My fantasies of a male to male encounter were often over powering. I finally worked up the courage to climb off the fence and take control of my fantasy. I contacted Evan and told him I would be at the mall in Braintree at noon, wearing jeans, flip flops, and a white button down shi...

Romeo, Where Art Thou Going in Life?

by walterio on Sep 14, 2017
Gay Male

Romeo had just turned 18 years old and he was still struggling with his sexuality. He was a very pretty boy who looked more like a girl than a young man. Because of his physical attributes many of his classmates assumed he was gay. As such girls were not attracted to him and many of the boys mocked him. Romeo was striking in his own way with dark curly hair...

Bathhouse Observations Ch. 02

by glory_first on Jun 9, 2020
Gay Male

Bathhouses are places with thousands of years of history, yet are extremely easy not to notice, unless someone is looking. That such places have existed is common enough knowledge, whether awareness of Roman decadence or when reading about certain Middle Eastern baths intended for men only. When there is a place where naked men can enjoy having anonymous sex...