Lost Bet Stories

182,389 results
Orientation
Length
Source
Infinite Scroll

Scott Lost The Bet Ch. 01

by Selena Down on Sep 13, 2017
BDSM

The Pittsburgh Steelers, his favorite football team, lost the big game to the Philadelphia Eagles. Scott, being a Pittsburgh boy, always rooted for his Steelers, no matter how bleak the odds were. Deidre, on the other hand, grew up in Philly, so she had to cheer for HER hometown team. The husband and wife feuded for weeks leading up to the big game. Sunday...

Our Team Spirit

by wrestlerotica on Sep 18, 2017
Celebrities & Fan Fiction

"Good lord – when the hell is this game going to start? I thought the kickoff was going to be at 6:30... and it's already 6:35." - Charlotte began to complain. "Relax, Charlotte – it's only been a few minutes... it's getting ready to start. After all, they just finished the coin toss. See? Your team has elected to kick off." - Alicia responded, already doin...

Texas Hold 'Em

by Charles Petersunn on Sep 14, 2017
Group Sex

I have not submitted any stories in quite some time. I do apologize for that. Life doesn't always proceed as you would prefer. This story was written on the suggestion of a Literotica writer and award winner, Sack. I hope you enjoy my Texas Hold 'Em variation on the card game theme. Some understanding of the rules of Texas Hold 'Em would help, but it's not r...

A Weighty Bet Ch. 02

by wishfulthinker on Sep 12, 2017
Loving Wives

I awoke the next morning feeling well satisfied after the best night's sex I had ever had. Jackie was more turned on and adventurous than I could ever remember. We tried things that I had only fantasised of before. The only thing she wouldn't allow me to do was take her anal virginity, but who's complaining we had sex for the first time for months and it was...

Bet Your Bottom

by RejectReality on Sep 12, 2017
Anal

"I can't believe you're making me do this," Natalie said as she stood on the hotel balcony at three a.m. with the wind blowing through her strawberry-blonde hair. Her eyes scanned the parking lot, and though she didn't see any signs of life, someone down in the darkness would be a lot harder to see than she would be on the balcony — dimly lit as it was...

Side Bet

by Drackman on Sep 17, 2017
Loving Wives

It's not my fault. I didn't even want to come to fucking Vegas! But somehow Charlie talked me into it, and then our "romantic" honeymoon turned into just him playing cards all the time and leaving me to my own devices. I guess I should have seen it coming. I should have listened to my friends when they told me not to marry a man 10 years older than me, tha...

Our First Thanksgiving Together

by Migtydep1 on Aug 31, 2017
Exhibitionist & Voyeur

A couple of winters ago my girlfriend and I got into making cute little bets, usually of a sexual nature but sometimes they were for pride or for control of each other. This was one of those times that she displayed her love of controlling a man. Susie, my girlfriend in my mid-twenties, was my May December romance. We'd met through a working relationship w...

A Weekend in a Cabin

by tascalun on Sep 17, 2017
BDSM

I met Angel through a friend but only got to see her three or four times before I was invited to a cabin with her and a mutual friend. The cabin belonged to Angel's family, John and Katie wanted to go up to get away from the city and Angel offered to let them come up with her for the weekend. I was invited so John and Katie wouldn't feel like they were leavi...

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...

Tinkle Bell Ch. 02

by Many Feathers on Sep 13, 2017
Fetish

Leading me into her room, and then towards the bed, I saw she had left the door open after entering. "You ah...might want to close that. As long as the doors to our rooms are closed, Doreen knows not to enter." And though it was early yet, not even eight in the morning, Doreen usually began making her rounds, cleaning rooms and changing sheets on the beds w...