Gay Lost Bet Stories

11,538 results
Orientation
Length
Source
Infinite Scroll

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...

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...

Bachelor Party Mishap

by vikkihawe000 on Jul 14, 2020
Gay Male

Arthur had just returned to his Las Vegas hotel room after a night at the blackjack table. His friends had organized the whole trip for his bachelor party as one last hurrah before marriage. He asked his friends for a tame weekend, just some drinks and some cards in Vegas. So far, his friends had cooperated. He loved Jessica and she made him promise that the...

Center Stage Ch. 06

by Gryffindor on Aug 30, 2017
Gay Male

I’ve always heard the expression ‘like a deer caught in headlights’ but I never truly understood the meaning of it until this exact moment. Time seemed to slow down. I could feel myself stop breathing. There is no way this is fucking possible. It is supposed to be Lucas. He’s supposed to be the crazy nut job that’s been harassing me. I could practically hear...

Workout Buddies Ch. 03

by 60031Guy on Dec 10, 2018
Gay Male

Workout Buddies: Day 2 of Paying Off the Bet (c) 2018. All rights reserved. _____ Author's note Hi there, thanks for taking the time to read this story. Please let me know what you think. This is my second story submitted anywhere, and is a continuation of, Workout Buddies, Chapter 1, The Bet. Folks seemed interested in the first chapter, so this is the...

Samaritan

by MrCain on Aug 22, 2018
Gay Male

I had a stroke. How severe it was, would depend on your point of view. My speech is slurred, my body is weak and my balance and coordination are way off and I now need a cane to walk. Couple that with the fact that I'd torn my rotator cuff few months prior to the stroke. Needless to say, I was not in great shape. On the bright side, there was no pain, and as...

Norwegian Stallion

by sr71plt on Aug 18, 2017
Gay Male

One of the saddest—and most ironic—casualties of the internecine Greek-Turkish war on Cyprus that divided the island into warring camps three decades ago was the once-famous and elegant Ledra Palace Hotel. The Treaty Room of the Ledra Palace, a hulking stone edifice in the Moorish style, had been the venue where the British secretly committed the crime of sl...

Andy Wins the Bet

by cyravance on Aug 18, 2017
Gay Male

He had just gotten out of the shower when the doorbell rang. "Shit!" he said, quickly toweling dry and wrapping the wet towel around his waist. He wasn't expecting his brother to arrive until noon, it was only 10 am. The stupid son of a bitch could have at least called to say he would be early! He walked to the door, intending to give his brother an earful....

My Hot Uni Roommate Ch. 10

by CreamStuffedTwink on Jun 8, 2020
Gay Male

Previously in chapter 09: "Down boy, down!" I joked. "Do you want to get dressed and play some games or something?" It turned out that he did. We played together until midnight and then we ended up sleeping in the same bed again, this time his. As we fell asleep, he kept slowly rubbing my smooth legs which felt even better than when I felt them myself. Th...

Cheating Ch. 02

by bi_nympho_scorpio on Sep 15, 2017
Gay Male

Part 2 (Derrick's Point Of View)... Fucking my roommate's boyfriend, Lance, was some hot shit. J is my boy, but I didn't really feel any remorse for what I did. What can I say? I'm a dog. I knew that bitch, Lance, was a hoe from the beginning. I have a high sex drive, so it really didn't matter who I fucked, as long as I fucked. One of my many fantasies i...