Losing Bet Stories

101,365 results
Orientation
Length
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Infinite Scroll

Game Bet

by BuckAustin on Sep 14, 2017
Fetish

It all started when our head Cheerleader, Carol, got a mysterious note in the mail. The Turkey River Jr. College Cheerleaders, wanted to make an unusual bet on the football game with Charleston Tech. It sounded like a sure thing that would be exciting, especially since our team had been on a winning streak this year. Winning streak was an understatement, no...

The Bet Ch. 01

by MivannaRai on Mar 6, 2018
Humor & Satire

"Shut up with yo little dick." God, why am I doing this? Somethings I really do hate my big mouth. This is all my friends fault though. One random day in Chemistry Katy told me that she thinks Ethan has a big dick. I immediately disagreed because of the simple fact that he's a show-off, a cocky prick and usually guys like that are all talk. So we started d...

You Lose. Now... Ch. 01

by glendale22 on Sep 11, 2017
Exhibitionist & Voyeur

"You lose. Now take off all of your clothes." Although I had heard this command several times, I never got used to the uneasy feeling it caused. At first, the consequences were actually kind of fun, but what began with my tendency to bet on my old college team eventually led to more and more embarrassing situations. It started when I was dating Karen, the...

Losing the Bet

by talkmedown44 on Sep 13, 2017
Loving Wives

"They stink at free throws!" That was the start of this adventure. Kind of unexpected to tell the truth. When our group gets together we often make silly bets with weird payouts. We're all generally too poor and cheap to make bets about cash, so we like to come up with dares or actions or sometimes even chores the loser has to do. One time I had to wash a b...

Prices and Risks

by Jappio on Jul 30, 2019
Exhibitionist & Voyeur

Prices and Risks Part 1 By Jappio Patrons sat in chairs and stools lining the bar and tables. Drinks and food were served to many there, but none had been to the most popular table for some time. Merriment and banter had first been exchanged, but started to turn to discourse over time. A sharp dagger cut into the table, wedged in the wooden boards, a met...

Dressing Up For My Wife

by dirtyjoe69 on Sep 13, 2017
Transsexuals & Crossdressers

My wife and I had a bet on the football game that pitted our two rival teams against each other. It was a horrendous day for my team and hers slaughtered mine 31-0. It was the same bet we always have with each other. It is a bet where no one really loses because it ends up with us having wild kinky sex. On earlier bets we have had, she has had to let me fuc...

Same As Us

by Ashson on Aug 19, 2017
Exhibitionist & Voyeur

Bob and I were waiting by the change rooms for the cheerleaders when they finished their practice. I nailed the captain as she walked past. "Excuse me, Marie, but could I have a quick word with the team before they get changed. Preferably in the change room." "Why?" "I have a proposition to put to them And I think it's only fair that they all hear it. It'...

Fun in the Rain

by Dawns on Sep 13, 2017
Group Sex

On a warm Sunday afternoon in mid July about 3 o'clock twenty of us who had been playing softball regularly gathered for our weekly game. We were a mixed crowd ranging in age from say 20 to 35. The field was located near the town high school. It was well maintained as it was also used for league baseball games. A few at a time the cars began arriving and...

Loss of a Bet

by VeladrielShipper on Oct 15, 2017
Celebrities & Fan Fiction

>**Title:** Loss of a Bet >***Rating: Explicit*** >**Summary:** After losing a bet with Woosa, Chiwu has to be his pet for a month; doing anything that he wanted him to. As it turns out, Woosa wanted to know just how far he could go one day when both he and Chiwu are in heat. >**Ships: Chiwoosa** >**Status:** Complete >**Chapter(s)**:...

Rachel and Me Pt. 07

by schmoe90 on Dec 23, 2019
Exhibitionist & Voyeur

I was playing poker online against a couple of friends. We were playing for real money, and were down to just me and Steve, as Jason had gone bust. We were teleconferencing so we could trash talk each other while we played, so when there was a knock at the door, I told them I'd just be a minute. I opened the door, and it was Rachel. She was wearing a baseba...