Losing Bet Stories

101,365 results
Orientation
Length
Source
Infinite Scroll

My Rugby Club Bets Ch. 01

by RiskyGirl on Sep 13, 2017
Exhibitionist & Voyeur

It was just a few weeks into the Rugby season when I went with Carl to a game at his old club. We were stood with the coach and reserves during the game and some of the things I said were not very complimentary. They were not playing well and by half time were down by twelve points. As they walked off the pitch I even offered to play for them in the second h...

Roommate Ch. 01

by WhoAmI99 on Sep 12, 2017
Exhibitionist & Voyeur

1: Strip poker I had just graduated college, and I lived in a nice big house just off campus. After graduation, two of us were planning on sticking around for the summer, but three were going off to jobs. Larry was the other guy that was staying. So, we started asking our friends for suggestions about potential summer sub letters. Ultimately we settled on t...

Older Neighbors Win The Bet Ch. 02

by wildp on Sep 12, 2017
Group Sex

I was sitting on my couch a couple of days after losing the bet with Sarah and Kim. I was still amazed at how great the sex was that night with them. I had never looked at big girls before but had always wanted to be with an older lady. Sarah was fourteen years older than me and Kim was thirteen years older. As I was sitting there thinking that the phone ran...

Cum Addict Pt. 02 Ch. 07.2

by novella_champ on Sep 14, 2020
Novels and Novellas

Chapter seven Part two: Kat's Weekend in Germany This is module two, chapter seven. This is a novella of sorts. The intent is to have 4 modules total covering different times in our main characters life. While it is feasible to read any of these independently, this is a carryover story, so reading them in order is beneficial. In module one, our main ch...

The Advent of the White Mini-Skirt

by LeggoMyEars on Sep 12, 2017
Exhibitionist & Voyeur

Christy knew all too well that her love, Dusty, loved exhibitionism. One day she was shopping for a new skirt when she spotted a semi sheer white cotton skirt that was short enough that if she sat directly across from anyone, they would have a clear view up her skirt. She modeled it for Dusty later that day. He was pleased with her choice naturally! That we...

Side Bet Bluff Ch. 01

by statsultan on Sep 12, 2017
BDSM

*** This story has also been posted on another site under the pen name Hal C. Rex. Hal and Stat are the same person. *** Part. 1 -- The Poker Game "Zack's not coming," I said angrily while putting away my cell phone. Damn all women and their meddling, controlling, and manipulating ways. "His new fiancée has better things for him to do." Our once regular...

The Game Ch. 03

by Psishadow on Sep 25, 2017
Exhibitionist & Voyeur

It had been three weeks since the strip poker game and the wild night that ensued. They were going to play again tonight and Doug had been looking forward to it all day. He showed up at Jenifer's and found out that everyone else had already made it. Jenifer and Lynn were both there as well as Nikki. Tiffany and Paul had made it also, but Michelle wasn't ther...

I Still Wonder

by openeyeddream on Aug 18, 2017
First Time

It is as a matter of fact a true story. The story which turned me into a man from a boy. I was working with a hotel. To be a virgin, shy and reserved boy at an age of 20+ is really surprising. And so were my friends. To them I was suffering from some disorder. But not exactly, it was a complex. I was afraid of the circumstances that one has to face in the...

Humiliated by Boss' Daughter

by radassat on Sep 17, 2017
BDSM

"Come up, I need you upstairs," said Sarah and closed. When you work for rich people you have to do a lot of things to satisfy them. And the children are even more moody. Sarah, who started college just a month earlier, liked to give me a lot of things to do. I was sure that sometimes, she was doing that only to have fun. She was a little bit bitchy, just l...

Should I Share?

by AngusStoryman on Sep 13, 2017
Loving Wives

My wife Tess had been looking forward to this evening for weeks and had taken longer than usual to prepare herself. She must have been in that bathroom for 2 hours, but when she finally made her entrance...I was almost speechless. She was dressed in a very sexy outfit consisting of an almost sheer white blouse that buttoned down the front and she had 3 butto...