Losing Bet Stories

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Superbowl Bet and Payoff

by will4play2 on Apr 22, 2020
BDSM

Randy and I had been playing a lot online but wanted to realize our relationship in real-time. And so it was we agreed to meet face-to-face. Yet every time we would set up an appointment, Randy would cancel last minute. Randy finally admitted, I'm apologizing to you a lot these days. Though we are both switches, I have always considered myself slightly mor...

Losing Your Senses Ch. 02

by schwammi99 on Sep 17, 2017
BDSM

For almost half an hour I had teased my wife depriving her of her senses, all part of a lost bet. She lost but I took the opportunity to turn the tables and cash in on the payout. With her hands tied and her eyes covered with a blindfold, I filled her ears with the sweet sounds of sex listening to the audio of a hot lesbian encounter. At the same time, I...

Fate's Prey

on Dec 27, 2016
Exhibitionist & Voyeur

Their names were Jackie, Alice, Rachel, and Michelle. They were ordinary girls, for the most part. But something strange seemed to follow these girls all of their life. None of the four girls could seem to keep their clothes on for long, leading to all sorts of embarrassment at their seemingly inescapable nudity! It seemed that these girls were Fate's Prey,...

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A Wager Lost Ch. 01

by DungeonKeeper on Jul 13, 2020
Erotic Horror

Krissy sat slumped in the corner of the drafty unfinished and empty bedroom on the carpet of their almost finished house, her head resting against the wall. She languidly watched dust motes travel across the ray of sun that shone forth from the skylight in the ceiling above and sighed tiredly, still fatigued and sore from the sparring session with her husban...

The Last Jar Greg and Sabrina-Rough

by billddrummer on Dec 25, 2019
Erotic Couplings

Greg grabbed Sabrina's arm and quickly led her down the hall. He squeezed it, hard. His touch was brusque, almost rude. To her, it seemed that he was rushing, wanting to get to the bedroom as soon as possible. She followed willingly, but had trouble keeping up with his purposeful strides. Sabrina is 5'3, mixed Asian and Hispanic heritage. The blend created...

Breaking Balls

by balboa_rain on Sep 15, 2017
Loving Wives

"Yeah, I called you a gagger, Ron! You never get a hit when we need it, and that error in the third inning let in three of their runs!" "Give me a fucking break. You're always looking to pin reasons for losing on someone else! Why not try looking in the mirror for a change? Who's got a higher average, huh?" The party was still going on around us as Tony an...

Arm Wrestle with Susan Ch. 01

by Shenthus on Sep 14, 2017
Erotic Couplings

Hi My name is Rob. Now I am not well built, in fact I have always a bit on the side of skinny. No matter what I did when I was a kid I couldn't put on weight and even now I am small. I am 175cm tall and weigh 72Kg soaking wet so, as you can tell, I am not Mr Muscle Man. Having said that I don't back down from a challenge as a rule, I have always had good bal...

The Wager

by thewinesnot on Sep 14, 2017
Exhibitionist & Voyeur

Introduction "Fuck me," Alicia said. Well, not said exactly. She thought it as loud as she could, but she wouldn't be saying anything. Instead she ground her teeth into the rubber cock shaped gag in her mouth. A slight noise escaped her mouth and the man sitting at the desk looked up curiously. He raised an eyebrow as if to ask her a question but then shrug...

The Wolf Wears Fleece

by maninconn on Sep 19, 2017
Loving Wives

My wife was known for her imagination. She was also known for her ability to get what she wants. She was also sneaky as hell. Stir these three facts into a preamble about fantasies and I was instantly on guard. How dare she? Here I was on this sunny Thanksgiving afternoon. I had cooked the turkey for her. I had been polite to her friends and family who came...

Super Blow Bet

by Annebelle on Sep 1, 2017
Humor & Satire

My college roommate, Mary, and I boarded the flight to San Diego on our way to the Super Bowl. Mary had just lost her virginity with my help. As a result of the circumstances surrounding that event we had received two free tickets to the big game. Not only that, but after our double-team on the professor, Stephen Chandler, Ph.D., who donated the tickets,...