Gay Bet Stories

4,201 results
Orientation
Length
Source
Infinite Scroll

The Changing Room

by velokev on Sep 14, 2017
Gay Male

In 1991 I was just barely 21 and working one of my first jobs as an assistant manager at a slightly trendy clothing store in the local mall. I wasn't paid well for it, but it was a little to put in my pocket, and I didn't have many expenses, so it all worked out. I was more frequently given the job close up, so I'd work the afternoon-to-closing shift, which...

My Angry Tenants Ch. 15

by rae121452 on Mar 6, 2018
Gay Male

It was a hot August night with a full moon. Ron and Gary had been working since sunup to finish a remodeling job in a un-air conditioned building and it had been in the 90's all day. Even now, at 10pm it was still in the 80's and they had 20 miles of country road to cover to get home. Gary was in his favorite summer work outfit; a tight pair of 501's cut of...

If Motel Rooms Could Talk

by timmywells on Aug 18, 2017
Gay Male

The dingy and dated decor of The Skylane Motel on Central Avenue just outside the state's capital city hadn't been updated since Gerald Ford was President, but most of the people who stayed there didn't care. That was the case on the night of May 25th, when a nondescript 53 year old married man named Melvin Stark paid the $33.50 to rent room 108. The man ha...

Stallion Station Ch. 02

by sr71plt on Aug 28, 2017
Gay Male

"It sounds too complicated for you, Matt," Jason had said. "Getting a list would be the hardest part—impossible, I think. This is a small potatoes town. I think you should just keep it to the street and be happy when it works out. And get a job." I'll admit that getting a job was what got the plan rolling. Then getting a list turned out to be one of the eas...

Workout Buddies Ch. 04

by 60031Guy on Jan 1, 2019
Gay Male

Author's note Hi there, thanks for taking the time to read this story. Please let me know what you think. This is the fourth chapter in my Workout Buddies story. This story contains scenes of M/M, M/F, MMF, oral, anal, dominant/submissive sex, cock sucking, butt plug, and cum eating. If that offends you, please don't read. Support The site you are readi...

The Poker Master

by MixMasterFlex on May 1, 2018
Gay Male

So I had a friend named Reshawn in college who also had a serious obsession with poker. We played obsessively, convincing our friends to join us for a game in our dorm whenever we could. When we couldn't get a game in person, we would play online, share stories over IM, and sometimes trade money on the various sites. One day Reshawn had asked to play on my...

Old Jack Ch. 02

by exaucer on Sep 14, 2017
Gay Male

My Working Day: I didn't get to work until after 9.30 and when I entered the office my boss called me over to inform me that I would be going out with Jack for the best part of the day to visit claimants who could not make it in for interviews on account of their physical difficulties. Part of me was delighted and part of me was quite apprehensive. However,...

Dick Out!

by peebudy on Sep 15, 2017
Gay Male

"This dollar says you miss that putt," John said, waving a crinkled dollar bill as George stands over a 6-footer. George glared at John for breaking his concentration, then re-focused and drilled the putt into the back of the cup. "Pay up bitch!" George said with a grin, snatching the dollar from John as the walked toward the 15th tee. John thought all the...

Sports Massage from Friend's Dad Ch. 02

by SluttyBisexualGuy on Feb 13, 2018
Gay Male

Braden couldn't believe he was actually going to the Fourth of July party. He was in his car on his way back over to his friend Nathan's house—the same house where only a day prior he had taken his first fucking from his father's sizable cock. He had fucked him in the ass on the massage table. And then he had cum in his mouth—even as Braden could taste h...

Lost Bet 07: Next Year

by dmoney4114 on Nov 8, 2017
Gay Male

Lost Bet Part 7: Next Year I was walking on a treadmill as a jiggly ass cycled in front of me. I had a perfect view of every movement and ripple which allowed my thoughts to wander to last year. My string of sexual experiences starting with a bet on a childhood game that I had made up, and culminating in, a bill for a destroyed dressing room, and the strang...