Wager Stories

2,436 results
Orientation
Length
Source
Infinite Scroll

The BJ Bet

by Xedmeister on Sep 17, 2017
BDSM

I don't know exactly how it got started, but on one particular Saturday, I found myself in a wager where I bet that my cum-guzzling whore (which she likes to be referred to as) couldn't milk me dry. The wager was pretty humourous - I had bet that she couldn't make me cum three times. If she didn't I forget what the prize was for me, perhaps filling her ass w...

Hot Tub Wager

by jetson9 on Sep 13, 2017
Exhibitionist & Voyeur

This is a true story, not a single embellishment. I love public nudity, and am always trying to figure out how to get my wife and her friends naked. For years this was an uphill battle and usually required enormous amounts of alcohol to accomplish. Even then it was hit or miss, usually miss. But in the last few years she has become much more comfortable get...

The Vixen Chronicles Ch. 08

by Sir Edward on Sep 17, 2017
Loving Wives

I instructed my wonderful submissive hotwife, Vixen, to go off on a sexual adventure with a delightful couple I know. She was required to write about it. This story is the result, and there is not one word of fiction in it, everything is true. Ask her yourself: I was very anxious to meet with the two of them. I had met with them before for sexual encounters...

The Literotica Olympics Day 14

by Rumple Foreskin on Sep 12, 2017
Chain Stories

EXHIBITION CONTEST: USA-STYLE FOOTBALL note: Since the inception of the modern Olympics, a number of new sports have been added such as Judo, Baseball, and something called Rhythmic Dancing. However, many others, including American-style Football and the grand old Scottish sport of Caber Tossing are still excluded. During the Olympics some of these sports...

Pathetic Excuse For A Man

by makofin on Sep 15, 2017
Loving Wives

I know this story is a little long. But the truth be told by Angelique’s husband Kyle. I hope you enjoy the twists, Angelique did. ***** I can’t believe all this has happened to me, or to us I should say. One day I’m climbing up the corporate ladder, riding the crest of the wave it seems, the next thing I know my life is a complete nightmare or worse. I di...

Ultimate Fantasy Football Ch. 01

by erossmantic on Sep 3, 2017
Erotic Couplings

THE DRAFT Sexual tension grew with each passing week between Steve and Jen. The two worked for the same New York marketing firm. Jen was a three-year veteran in the office; Steve was the newbie, stolen from a competitor two months before. Both were good at what they did, competitive in their work and admirers of the other. While the company discouraged inne...

Fair is Fair

by writingdirty on Jan 22, 2018
Erotic Couplings

"It's not fair," Audrey muttered as she unbuttoned her blouse. I tried not to laugh as I continued moving things around my bedroom to give myself the most access. I stripped the pillows off the bed and moved a chair and a folding table next to it. I put a tray with cold glasses of water and snacks on the table. The whole thing was going to take a glorious w...

A Woman's Wager

by andtheend on Sep 13, 2017
Transsexuals & Crossdressers

A man who lost a bet must dress as a woman and discovers he likes it. "Pardon me, Madam," said Ed trying to hustle his shopping cart down the aisle by a very large woman. With her carriage blocking one side of the aisle, she was hunched over a shelf with her big ass blocking the other side of the aisle. When the woman turned to move her carriage out of the...

The Bet Ch. 01 - A Football Game

by Thors_Fist on Jun 19, 2019
Loving Wives

This story is based upon a photo series, "The Bet", by Italian photographer, Andrea James Bramley, who recently signed up on Literotica under user name BramleyAppleTheForbiddenFruit. I write this with the permission of both he and the model featured in "The Bet", and with his collaboration. He especially helps with some of the Italian phrasing, which I don't...

Secret Friends with Benefits Ch. 02

by TabooDreaming on Sep 24, 2018
Erotic Couplings

It was still early when Brad left that morning. He had fallen asleep on the couch, as had Mike, and the discomfort only allowed him to sleep for so long. Seven in the morning was later than he expected, but it was not a restful night. He left then, knowing that staying would only lead to more uncomfortable sleep, and inevitably, Mike may convince him to ab...