Lost Bet Stories

182,389 results
Orientation
Length
Source
Infinite Scroll

Hubby Losses a Bet

by Sexybeast8899 on Oct 19, 2020
First Time

A friend of mine is a New England Patriots fan. So is his neighbor Todd. Last season they had a party for the Patriots game versus the Chiefs. I'm a Chiefs fan. They invited me over for their party. The Patriots were the home team, but the Chiefs were having a good season. "Good to see you, please come in in!" Todd said as he greeted me at the door. "You...

Losing Your Senses

by schwammi99 on Sep 13, 2017
BDSM

It all started with an innocent bet over dinner one evening. With nothing more than a quick check of the internet I had won the bet, but I was not ready to collect. That would wait for another time and place. We did not even decide what the reward was. All she knew is that she lost. Weeks later, I decided it was time to collect. The kids were gone for the...

Bill's Slutty Girlfriend

by hottie morgan on May 6, 2011
Romance

Bill watched Morgan pack her things. "I can't believe I lost that bet," she shook her head. He watched his gorgeous girlfriend prepare for the weekend away. It was all part of the bet. They bet on who could go the longest without sex, not even masturbation. Morgan had made the bet as a joke. If Bill won, she would do whatever he wanted for a whole...

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Julie Loves An Audience Ch. 1

by Clayton on Sep 16, 2017
Exhibitionist & Voyeur

Julie was always a lot of fun. She lived with me for several months after my divorce so she could save enough money to go back to college. Like most 22 year old girls she had a flat stomach and a tight butt. She was brunette, 5'4" with long legs, a 23 inch waist and 34B tits. Julie would usually serve drinks and snacks when my buddies came over for poker on...

The Bet Ch. 01

by sadkins116 on Dec 25, 2018
Exhibitionist & Voyeur

This is a story about a young college co-ed who learns the hard way gambling isn't for everyone. . It was requested by a young lady who has enjoyed some of my other stories. Chapter one sets everything up and has the bet. Subsequent chapter's deal with her trying to pay off the bet and end her torment. This story has lots of exhibitionism and eventually non-...

Big vs. Biggest

by HornyHenry on Sep 11, 2017
Erotic Couplings

A story based of a suggestion from Sirhugs. Thanks for the inspiration. * It was early Friday morning. Sean was lying on the couch in his girlfriend's college dorm apartment watching TV in only his boxers, when her roommate, Janelle came in, wearing only a sexy little baby blue nightie. "Hi, Sean? How's it going?" Janelle greeted him with a smile. "Hi, J...

ENM Intertwined - Rorke Pt. 06

by SpecialtyM3 on Oct 7, 2019
Exhibitionist & Voyeur

I will have to worry about the bet later. Right now, I had another sport that I can look great in: the swimming competition. This time I was up against my buddy Santiago. Being the former captain of his high school swim team, he was going to be tough to beat. "Hey Sage," I spoke to my crush as we walked out of the station to the beach side. "I won't forget...

Nar Shaddaa Rules

by evil_kitten on Sep 13, 2017
Celebrities & Fan Fiction

Atton stalked restlessly through the corridors of the Ebon Hawk. A certain Jedi Exile was driving him out of his mind. Raia seemed to be everywhere he looked lately, and on the rare occasions when she was out of sight he couldn't stop thinking about her. It wasn't that he didn't like her, far from it; the problem was that he liked her way too much and couldn...

Partner's Best

by swappingpartners on Sep 17, 2017
Loving Wives

This past weekend was one to remember that I just had to post. My wife and I along with another couple decided to spend the weekend at Metropolis, a small community in southern Illinois. The gambling on the boat was just the beginning of bets for the evening. We picked them up on the way and spent the next couple hours discussing how much money we were goin...

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...