Gay Lost Bet Stories

11,538 results
Orientation
Length
Source
Infinite Scroll

Summer Sausages Ch. 01

by rae121452 on Nov 27, 2017
Gay Male

Bill and Lee were bored. The lifelong best friends, next door neighbors and occasional fuck buddies had just completed their first year of college and today was the first day of summer break. The two 19 year olds had spent the morning swimming in the pool behind Bill's house and now they were lying in the sun, working on their tans, dressed only in matchin...

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...

Job Evaluation -The Christmas Party

by VeryCuriousIan on Mar 18, 2020
Gay Male

It was now over a month since Ian's last disciplinary problem and he had at long last got his act together. He was now one of the best employees in the office. Even Carol, his hated line manager, had to admit he had turned over a new leaf. Although she still loved to call him a little cocksucker anytime she could to cause him maximum embarrassment. Ian's...

Calluses Pt. 05: Scab

by MrMister23 on Jan 7, 2019
Gay Male

The buzz of my secret orgasm faded, and the last remaining dribbles of my sticky cum globbed up against the clumps of black pubic hair, mine and his, clinging stubbornly to the metal ring of the drain. I poked at the mess with my big toe until the lazy spiral took it down into the pipes below, and then it was done. I sighed and relaxed my muscles, my mind......

My Very Gay Weekend Ch. 01

by Daulton_Trumbo on Aug 18, 2017
Gay Male

I couldn’t believe that this was happening. It all started as an innocent bet. Of course, I had lost. Because of a stupid tipped ball in the endzone, I, Cliff Bartum, Mrs. Bartum’s baby boy, was on my hands and knees between my roommate’s, Aaron’s, legs. Because I lost the bet, I was supposed to be Aaron’s slave for the week. (I know it was stupid, but I w...

Poker with Mr. Harris Pt. 02

by matanda on Aug 24, 2020
Gay Male

After beating me yet again, Tony grinned wide and gave me a hard time as he gathered my money. "Cold streak, Chris?" I just rolled my eyes. The last four or five weeks had been miserable. I really was on a cold streak. I hadn't won once but, honestly, that was the least of my concerns. I felt uncomfortable every time we got together for our weekly poker ni...

My Hot Uni Roommate Ch. 09

by CreamStuffedTwink on Jun 8, 2020
Gay Male

Previously in Chapter 08: Were we going to fuck soon? Was he going to fuck me tonight? Maybe the plug was intended to help ensure I was super stretched by the time we got home. That made sense. My mind was racing with possibilities. I finally snapped out of it when the waitress returned with the credit card and Michael scrawled a tip amount onto the receip...

John Joins The Boys

by TUCSON RED on Aug 31, 2017
Gay Male

This is a continuation of my loosing a bet series so if you haven’t read them yet please do. I am married to a twin who is the sister of my twin sister’s husband. In other words my sister is married to my wife’s brother. ***** The girls had taken Mona my mother in law to Los Vegas for a week of fun. They were visiting a collage friend of my wife and me. Sh...

Choices

by fadedgiant on Aug 18, 2017
Gay Male

What I was not expecting, what I could not have imagined, is being physically overcome by my lust filled desire. He stood there, as he has daily, with the same smile and same swagger he always displays. Why am I suddenly willing to bare myself naked for him? Why do I feel this need for him? Why do I want him to fuck me like a whore? I have to stop asking w...

Thomas and Niko Ch. 08

by kidboise on Jan 8, 2019
Gay Male

Thomas and Niko in the City of Trees - Chapter 8 — So word gets around and about twenty-five people show up. Owen's cousin works at Urban Brewing and supplied a keg, which is a pretty big windfall in case you didn't know. We all chipped in and Thomas and I went down the hill to Garden City to pick it up. Anyway, it's getting close to ten now, and everybody...