Girlfriend Bet Stories

104,405 results
Orientation
Length
Source
Infinite Scroll

Back-alley Sissy Boy

by Travel_by_day on Sep 12, 2017
Fetish

I saw you while I was walking through the grocery store. You were bent over, picking up something off the bottom shelf. At first, I thought you were a girl, because of your nicely shaped ass and the fact that your low rider jeans were riding down, exposing a lacy white thong. I was so turned on, my cock started to get rigid right away. If I had been wearin...

Last Week of School Pt. 01

by andrewmoocow on Apr 3, 2019
Exhibitionist & Voyeur

My name is Amber Martinez, a freshman student at J. Oscar University and a member of the nudist sorority Alpha Zeta Zeta. Well, this was it. The final week of school before summer vacation begins for the students of J. Oscar University. For the past few weeks since late-May, my sorority sisters and I were finally allowed to go around the entire university...

My Math Grade

by feelmore on Sep 17, 2017
Mature

I attended a small college in S. Carolina on a football scholarship. I was never much of a student, but managed to impress the football scouts and coaches enough to get on the team. I decided to major in business instead of physical education like many of the other players. I wasn't good enough for the pros, so I figured I better get a degree in something t...

Winning an Unexpected Bet

by madmartigan37 on Sep 26, 2017
First Time

I was twenty five when this story happened, but still working on an undergraduate degree at university. I'd made some bad decisions right after high school, flunked out, taken a few years off to get my shit together and finally gone back. I was living with my girlfriend and she was working full time to support me, but I had a part time job at a bookstore in...

I Lost a Bet to My Friend

by Norwayadventure on Sep 14, 2017
Group Sex

My eyes went a bit wide with excitement as the buzzer indicated the game was over. I looked to my side to see my Girlfriend Kiara, wearing only a T shirt and a thong that left little of her to the imagination. Kiara has a perfect body; she stands at 5'4 with long and strong legs that came from wide hips and an amazing firm ass from a lifetime of exercise in...

Older Neighbors Win The Bet

by wildp on Sep 17, 2017
Group Sex

I was 24 and in great shape. That is why I could not figure out why my girlfriend dumped me. I wondered this as I got out of my apartment complex pool. It was bothering me and my neighbors could tell. So they tried to cheer me up. They were two ladies in their late 30's and both a little overweight but were both good neighbors. They always flirted with me an...

Anything for Lindsay Ch. 05

by allaboutcontrol on Sep 26, 2017
Fetish

"Oh god, oh my....," Jason said, in pure pleasure, trying with every ounce of his body to hold back from cuming. Lindsay was sitting next to Jason, slowly stroking his penis. Jason was completely naked laying on Lindsay's bed. Lindsay was fully clothed in a tank top and a pair of jeans. "Its only been 50 seconds Jay, hold on, you still got a little over tw...

An Untypcial Thursday Night

by dirkdiggler2008 on Sep 17, 2017
Loving Wives

It was a typical Thursday night, poker night with the guys. We were all still in college, and tried to get together every Thursday to play no limit hold'em. We all lived together, four of us in all, so it was pretty easy to schedule. This time my girlfriend, Megan, was up, she had come up from her college since it was a long weekend due to a holiday. We ha...

Seducing Sheila

by Lion24655 on Sep 14, 2017
Erotic Couplings

Chapter 1: Ungentlemanly Conduct... The office was probably quite typical of many offices. Not quite open plan - it had six desks in the middle of the room in a sort of hexagonal shape, all separated by screens, so that we all felt we were working in booths. The solid screens were quite high - perhaps six feet high - high enough to hide each of us from each...

I Lost a Bet

by sarahsmith1989 on Sep 14, 2017
Erotic Couplings

It was the kind of warm August night where you don't even want to move. My friend and I were just lying on the couches in my living room playing a baseball video game. We had just started a new game and it was still scoreless. My phone buzzed soon after we began play so I paused the game to fish it out of my pocket. It was rather late and I was wondering wh...