Lost Bet Stories

182,389 results
Orientation
Length
Source
Infinite Scroll

Mastering the Game

by devilinusall on Sep 17, 2017
Non-Erotic

"You lost the bet," he reminded her. Still, she felt oddly numb. She just knew she was going to beat him; he had never been much of a pool player. Big surprises come in small packages, and when you least expect them, he had once told her. He had said that months ago when they first met, and had repeated himself earlier today, just before the games began. But...

You're My Bitch Now Ch. 04

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

For what seemed to him to be the umpteenth time over the past few days, Rick blushed scarlet and thought he would faint. 'But I'm not wearing panties,' he said, looking anxiously over his shoulder to see if Steve was in earshot. 'Don't worry about him, he's tied up on a call. Look, I know you are, Rick. You were helping the moron from hell over there with...

Dear Prudence

by Harddaysknight on Sep 11, 2017
Loving Wives

"I'll take care of your coat for you, Prudence," I offered as I helped her remove her fur jacket. "Thanks, Mike," she smiled. "I'll see you at the bar after you've finished that little chore." That was when I noticed Steve Watkins and Barry Reynolds standing between me and the coat room. I could barely conceal my distaste as I attempted to walk around them...

A Lost Bet Ch. 01

by amarasfantasy on Sep 12, 2017
Transsexuals & Crossdressers

I was afraid. I knew I'd lost a bet with some guys I didn't really know and I had no idea what they had planned. It was stupid of me to have made the bet, but I just knew I'd win. We'd been sitting around playing poker and I was almost out of chips. I was biding my time though, watching my stack dwindle as I waited for my hand. Then it came, a straight flush...

Clothing Bank: Relationship Evolves

by kimberau on Apr 24, 2018
Exhibitionist & Voyeur

As I read each vote out loud, my voice rose in pitch - "4-3-4-5" "Oh my fucking god!" Sarah shrieked when I finished. "You guys all voted... oh my god!" Her face was red, but she was clearly excited at the realization that her vote for nudity was the lowest one. I took pleasure in the idea that my husband would get to see her naked, well - it was quite lik...

A High School Bet

by sexy_jessie on Sep 12, 2017
First Time

Jesse and Jessie Sinclair were two of the most popular kids in their senior year at high school. Twin brother and sister both were eighteen, tall and thin with shoulder length blond curls and bright blue eyes. Unbeknown to the rest of the school they were also two of the kinkiest people in the whole town. One day Jessie lay, lounging, on a sofa at their hou...

The Yes Girl Ch. 02

by sin138 on Sep 14, 2017
Exhibitionist & Voyeur

Please be warned that this story is quite dark and mean-spirited. While no pain or torture will be depicted, this story contains sadistic characters that have no respect for the protagonist. This continuing story will not end well for the main character. I do not condone the actions shown in this story, fetishes aside. If these don't bother you, then I hope...

Cruel Liaisons, Dangerous Intentions

by TheDarkCloud on Sep 17, 2017
Celebrities & Fan Fiction

Ryan stood at the large window of the student residence living room he shared with his sister and adjusted the binoculars he held to his eyes. He looked out onto the beautiful sunny day and the scattered groups of students on the lawns and benches sunbathing, chatting or just fooling around. These really were the beautiful people, especially the young women...

Blow Job Bet

by BigGuy33 on Oct 30, 2017
Loving Wives

This is a short one. Flash length. Yeah, I know I just did a poker-themed story. What can I say? They both came to me while I was playing online poker. Disclaimer: As you read this story, keep in mind that I try to include something for everyone, and some people are always looking for mistakes. So, if you find any errors, please remember that they are there...

Hikers Lost in a Snowstorm Pt. 01

by nogagog on Sep 14, 2017
Erotic Couplings

- 1 - "Thank you, George Lee," said Eli under his breath as he pulled what was undoubtedly an extremely expensive bottle of scotch from the pantry chest. It had been tucked unassumingly between a big tin of olive oil and a bottle of ketchup. The scotch had not been on the provisions list, but he wasn't all that surprised to see it; George was a generous sor...