Gay Lost Bet Stories

11,538 results
Orientation
Length
Source
Infinite Scroll

A Sure Thing

by PhillyPen on Aug 18, 2017
Gay Male

It was a sure thing. Almost. The Cowboys and the Eagles. At Dallas. On a Monday night. There was no way the Eagles were going to pull this off. The Eagles were about to get crushed. Yet there we were, two Cowboys fans sitting in Eagles territory on a couch watching the game. And while we watching the pre-game show, a playful bet arose with our girlfriend...

Straight Musician Turned Gay Whore

by GGandG on Sep 14, 2017
Gay Male

Something weird happened last night and I am very conflicted about it. I've been traveling across the country with my band and we've been crashing in people's houses along the way. They're small shows, we're barely breaking even financially and if we can keep that up it will be a huge success. Our fan base is growing so that's cool. Sadly there are not a lot...

The Bet

by LetsHaveFun on Sep 14, 2017
Gay Male

It's not every day that I get a call from a woman, asking me to fuck her heterosexual husband. So as you can imagine, this call was a surprise. My co-worker's husband Dave, desperately wanted to see her have sex with another woman. Suzie wasn't going to go along with it that easily, so she made him a bet. It ended up being decided with a simple coin toss. If...

Daddy, The Devil, and Me: Day 02

by DarkBroski on Mar 6, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. * Day 2 - Morning Location: Hospital Drake wakes, at first not sure where he is. Then flashes of last night. The car. Fire. The chest. The strange man. He looked at both of his hands. "That chest better have something wonderful inside of it." His hands were wrapped up in medicine tape...

The Roommate Ch. 03

by CalLorenson on Sep 16, 2017
Gay Male

This is a continuation of the story about my adventures with my girlfriend, Kara, and her roommate, Joyce. It takes place, once upon a time, when we were college students. Time-wise, this chapter occurs shortly after chapter 1. If you haven't read the first parts, I recommend that you do. However, if you want to plunge into this story, let me recap. Chapter...

The Post Season Ch. 01

by Rheese on Aug 17, 2017
Gay Male

"Dude, I can't fucking believe the Ravens are gonna win this." "No fucking way, man." I replied. "Brady is gonna march them down the field and win in the last minute." "Ha, bullshit!" Jason yelled as he stood up. "Want another beer?" "Sure. What's one more at this point?" I replied as he walked towards the kitchen. My eyes followed him. His large muscular...

A Bet's A Bet

by Trudes on Sep 14, 2017
Gay Male

"It's time to wake up now." With just those six words, I regained the ability to open my eyes. Regained? I guess that's not the right word. I'd only just dozed off—nothing more. "Well, how do you feel?" The hypnotist grinned at me. I didn't see why he was grinning, though. He was a friend of mine. His name was Kyle and he liked to think he was a master whe...

My Boss and Master Ch. 02

by MitchCapslock on Sep 14, 2017
Gay Male

All comments or criticism welcome. New rules, new life The message light was already blinking when I got to my desk Tuesday morning. "Mitch, this is Wendy. Mr. Compton asked that I remind you of your 4 p.m. meeting this afternoon in his office." Forget? It was all I had thought of since I left his office, the taste of his cum coating my throat. It was...

My Hot Uni Roommate Ch. 11

by CreamStuffedTwink on Jun 8, 2020
Gay Male

Previously in Chapter 10: "You just need to train until your butt is as hard as diamonds then. You've got... What? Two weeks left? Totally doable." "Speaking of which. I should go do some more homework. You can concoct more ideas for me to seduce my professors on your own." "Fair. I'll draft up some proposals and bring the best three for your consideratio...

When Opportunity Knocks

by NymphWriter on Aug 18, 2017
Gay Male

Ben and Lacy arrived at the small, hole-in-the-wall bar on the east side of town. Neither had been there before and were only there because Lacy had won tickets for a show in a raffle at work. Lacy wore a short leather skirt, white green blouse showing lots of cleavage, and her best heels. Ben wore his best jeans that hugged his ass and a maroon silk shirt....