Lost Bet Girlfriend Stories

201,764 results
Orientation
Length
Source
Infinite Scroll

Becky at the College Reunion

by clarkoverns on Sep 17, 2017
Exhibitionist & Voyeur

I finally broke up with Becky. I had been planning to break up with my her for a while, for cheating on me, but first I wanted to wait until my college reunion. I wanted to show her off to my old college friends, since, to be honest, she was the best thing I had going for me. I didn't have a great career or much money, but at least I could show them my knock...

Suzy's Control

by kong0645 on Sep 15, 2017
Exhibitionist & Voyeur

Suzy's control: So, after reading these stories for years I decided to share some things that I've experienced myself. This is a story that happened when I was in a May-December romance in my mid-twenties. It all started when I was twenty-five. Her name was Suzy and she was in her early fifties but was stunning and very much looked more like a woman in he...

Brand New Girlfriend

by JakeRivers on Sep 17, 2017
Humor & Satire

Author's note: After my last story I wanted something a bit lighter. This is based on Steve Holy's great song. Words and music copyrighted by Shane Minor, Bart Allmand and Jefferey Steele. A bit of fluff - best read with tongue firmly in cheek! Thanks to techsan for his timely edits. This story is a special request from my sister. SAY WHAT? "She...

Always Bet On Black

by Spassmacher5000 on Sep 13, 2017
Interracial Love

I was always so proud of my girlfriend. I guess that's what started this whole mess. I just couldn't stop showing photos of her to my friends, and taping them in my locker at work. She's just so hot, I had to brag. I should have just kept her to myself. Then one day this cocky black guy at work, Darnell, he walked by while I was at my locker. "Damn," he sa...

My Roommate

by ElspethMoans on Sep 19, 2017
Erotic Couplings

Based on a true story... It all started with a bet. Booze, and a little harmless flirting, and a stupid, stupid bet. I had a feeling when I moved in it would be trouble. I like living with roommates, and I like living with guys - no passive aggressive notes, no simmering resentments, if they're pissed they'll just fucking tell you. Sure, I've had a little...

Fire, Fire!

by Angelscuck on Sep 16, 2017
Reviews & Essays

It was August of 1969. I was sleeping on my nine foot by seven foot waterbed when a friend, who had needed a place to crash that night and was staying in the front room, came running into the bedroom yelling, "The house is on fire! The house is on fire!" I quickly jumped out of bed, stark naked, saying, "Well let's put it out!" and ran to the front room wi...

Sports Bar

by andymiami on Aug 19, 2017
Exhibitionist & Voyeur

My wife and I are exhibitionists and we have a repertoire of fantasy situations we enjoy. Of course we are always open to new ideas but it is exciting when she sends me a text that says "Sports Bar" along with a time and the name and location of a bar. The time always coincides with a major sporting event. We always arrive separately and try to sit at the...

Pizza, Baseball, and a Bet

by herfan on Jan 7, 2018
Loving Wives

This is another story about experiences with Jill, my first long term girlfriend and sexual partner. They are based on true events except that they are revised into a much more positive, pleasurable outcome. If we'd known then how to have a relationship good enough to do the things we could have, then maybe things could have turned out better. *** Jill and...

Neighbourhood Terror to Sissy Pt. 16

by Fibaro on Jan 6, 2020
Transgender & Crossdressers

Chapter 18 Marcy had hoped the stop at CC's would have been the last one. She had suffered enough embarrassment for a day. Lisa's claim that they still had a few errands to run made her worry that it wasn't all over after all. Her worries were soon confirmed when they stopped in a rather seedy looking neighbourhood. Getting out of the car Marcy knew better...

Root of the Problem

by MTL17 on Jan 29, 2018
Celebrities & Fan Fiction

Disclaimer: I do not own Person of Interest and have no association with anyone involved in the show. I do not make any money from the writing of this story. Author's note: This story takes place just after alternative Season 5, but no real spoilers. ***** "Let's just get this over with." Shaw grumbled. "Awww, baby. Don't be like that." Root pouted, bef...