Gay Lost Bet Stories

11,538 results
Orientation
Length
Source
Infinite Scroll

The Bookie Ch. 01

by tmh10 on Sep 19, 2017
Gay Male

When I was in high school, I learned of a guy who was acting as a local bookie, taking bets on sports games. Money was not easy for me to come by back then, so when I heard of the great odds he was giving on my favorite football team, I couldn't pass up the chance to place a large bet on such a sure thing. My plan was to score a good sum on the win, which wo...

Hypnosis Ch. 01

by velokev on Sep 16, 2017
Gay Male

I sat in my apartment on my couch trying to make sense of what I was doing. Only months earlier I had been snooping around a male-for-male message board out of pure curiosity when he started the conversation. His name was Todd. He began pleasantly and we developed a rapport about sports and other mundane things. I wasn't looking for a hook up, and was on my...

Two Married Guys Ch. 03-04

by Soshameless11 on Nov 4, 2019
Gay Male

Chapter 3 Tom had rolled over and slept the sleep of the dead shortly after blowing his load. He felt a little bad that he'd cut the guy off so quickly. But when he realized that he was thinking about taking Mark's cock in his hand when he exploded, he felt a mix of guilt and confusion that he couldn't understand. His phone went off at 7:30, and he lay the...

My First M2M Experience Pt. 02

by mikurt on Mar 16, 2020
Gay Male

...continued from my first submission This is still a very true story of how I was slowly seduced by an older man when I was a bi curious college student. * After that night in his apartment when he spit on his hard cock while we watched porn, I couldn't get my mind off of that image and what could have been. I also couldn't wait to get back there alone...

Caught, Blackmailed and Loving It! 001

by CSK on Sep 14, 2017
Gay Male

This story involves gay sex, group sex, semi-incest, but since the main theme of the story is gay sex, I decided to put it here. If this bother's you, please do not read any farther. Thank you and have a happy cum!!! -------------------------------------------- I loved it. I might have been doing these extra jobs to get some extra spending cash while in co...

How It All Begun

by BiGringo on Apr 21, 2020
Gay Male

The writings I submit are true experiences from over the past twenty-five years. Though they are not all of my experiences, they are my most memorable ones. Names have been changed to protect their identities. Also i would like to Thank HotandHollow for helping with the editing. ***** It was 1994. My brother, cousin and myself all lived together in a thre...

Dorm Showers Ep. 01

by renthead29 on Aug 18, 2017
Gay Male

"Pssst! Paul!" I heard the hiss above the roar of my little shower cubicle in the dorms. I paused from one of the near constant adjustments I was making to the temperature of the water and opened the curtain just enough to peek out. I could only see Jason's face peeking from his own shower across from mine. "What?" "Do you see anybody?" He half whispered,...

The New Gym Member

by exaucer on Sep 14, 2017
Gay Male

Wanting to get in to better shape I decided to join a nearby gym. Moreover I was feeling the need to look at other men naked. With your experience you will know the type of young man I am. I am the one who spends longer than is necessary in the shower, stealing looks at other men's cocks. I am the young man who is slow to get changed, sitting there pretendin...

You Bet Your Ass

by kudzu41999 on Aug 31, 2017
Gay Male

There's nothing worse than two divorced guys sitting around watching television on a Saturday night. Lamar lost everything when his wife took everything he owned. All he had left after he got home from work that day was the car and the clothes he had on his back. I wasn't much better off. The only difference seemed to be in the bills that were left behind. I...

The Collection

by thatkiwiguy on Sep 14, 2017
Gay Male

PLEASE NOTE: This is not really a romantic read. It's more a smutty tale touching slightly on themes of submission and control. It is a collection of scenes from a novel I'm working on and have pieced them together to be a shorter erotic tale. I hope you like it. ***** Callum Bradshaw carried a box of beer under his arm as he pressed the doorbell to his be...