Bad Bet Stories

179,314 results
Orientation
Length
Source
Infinite Scroll

The Bet

by Captain Steve on Sep 17, 2017
Loving Wives

"Want to make a more, uh, interesting bet?" I stared across the table into the steel gray eyes. They blazed with the fire of competition that characterized our relationship over the years. I too felt combative juices rising. Nothing short of an unequivocal answer would do. "Yes." "Since we started our business fifteen years ago, we've met the third Thur...

Bar Bet Weekend

by LiseKLord on Feb 7, 2018
BDSM

Joly and Rina had been friends since elementary school, through high school as well. They had been college roommates and now, five years after graduation, thanks to good jobs, they still chose to share a very nice condo in the heart of downtown. They knew everything about each other, and despite the occasional annoyances any living together relationship migh...

A Bet Is a Bet

by mollycactus on Sep 19, 2017
Group Sex

"We're gonna beat you so bad!" Pepper laughed. She was feeling quite cocky. Her college football team, the Golden Tigers, had mauled their opponents for the last 6 games. As head cheerleader, she had screamed herself almost hoarse by the end of each game. She'd run into the head cheerleader of their traditional rivals, the Silver Mustangs, quite by chance. B...

The Humiliation Of Jen Ch. 01

by Alfamann on Sep 16, 2017
BDSM

Author's note: This story has been written at the request of Jen. She does exist, lives in Louisiana, and Uncle Jimmy also really exists. However his shenanigans are purely the figment of Jen's very fertile imagination and the author's wayward sexual deviancy. Jen wants a slow build up in the story, so what Jen wants, she gets. I need to point out that thi...

A Friendly Game of Cards Ch. 1

by English Bob on Sep 19, 2017
Loving Wives

"Oh, come on Mike. I promise I won't get in the way." Mike looked at his wife. They had just got out of bed and were dressing, preparing for another long day at work. "Look, Kate sweetheart, it's a poker night. That means no girls! Anyway, I though you usually went to a movie or something with your friend Ruth?" "Ruth's on vacation and I've nothing else t...

Susie Loves Football

by motbitro on Nov 2, 2020
Exhibitionist & Voyeur

It was a normal Saturday during football season. I was in my apartment with Susie, my very cute and very sexy girlfriend, who simply loves being a playful cock-teaser. We were drinking Bloody Mary's watching the early games, getting "fired up" for the 5:00 game when our favorite team was playing. I began dating Susie in high school. As time went on and we...

Forty Hours: A Josh Hartnett Story

by cedar127 on Sep 17, 2017
Celebrities & Fan Fiction

Josh stepped out of the shower, water were dripping all around him. He was whistling to himself as he looked at himself in the mirror. The bathroom door suddenly opened and Shannyn Sossamon stepped in carefully observing his perfect body. “Good morning.” He said. “Tired?” Shannyn looked at him and smiled. “It was very hard keeping up with you last night.”...

Winning The Bet

by TahoeCat on Dec 12, 2018
Erotic Couplings

MMMmmm, if I had a better seat in the house I'd be able to lick the boots of the lead singer. And oh what pleasure that would be. He was tall and buff, just enough to make the mouth water. His eyes, a steely grey that shined down as he looked at me. His bright blue shirt was open just enough to show that his chest sported a healthy amount of hair, matching t...

Photo Studio Ch. 03

by m_storyman_x on Sep 13, 2017
Erotic Couplings

Authors Note: This is part of a series and is built on characters and settings from previous chapters. * The previous day was incredibly busy with an out of town photo job. I barely had time to dump my gear at the studio before heading home to flop into bed, so I didn't feel too bad not getting to the shop before nine. Part of me wondered if hiring someon...

The Bridge Club Ch. 08

by AspernEssling on Sep 12, 2017
Romance

Massimo had told Christina about the bet. I couldn't for the life of me figure out why he would do that. To fuck me over, sure. But he was forfeiting the bet by revealing our secret. Did he hate me that much? I had to know. So I called him, and set up a meeting at the fitness club. I didn't mention squash or tennis. He knew why I wanted to meet. Massim...