Lost Bet Girlfriend Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Lost Bet on Vacation

by softly_spoken on May 1, 2018
Group Sex

This is my first submission. I welcome feedback. I hope you enjoy! ***** I had first gotten together with Rachel 10 years ago in college. I was a Biology nerd, fit from running cross country in high school. Rachel was a sci-fi geek with a bubbly personality, but somewhat conservative in dress. Rachel revealed that she had not enjoyed the attention her 32 D...

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...

The Lost Bet

by WordWizard55 on Sep 13, 2017
Erotic Couplings

Becky woke up and rolled over to look at the clock. '2:30 a.m. - where's Jim? He should be done with his poker game by now.' Becky's live in boyfriend Jim played a weekly game of poker with his friends- usually at their apartment since they had a pretty nice poker table. Becky didn't mind his weekly gathering as she knew it meant a lot to him to be able to...

Katie's Lost Bet

by Captain_Ron on Sep 26, 2017
Exhibitionist & Voyeur

Note: These events take place after "Katie's Pool Party" ***** It was a grey Sunday morning and Katie rolled over in bed looking out the window apprehensively at the sky. The annual city half-marathon was coming up in a few weeks and she really wanted to get a long training run in this weekend. She picked up her phone and checked the forecast and decided t...

Betting with Beth

by Brookell on Sep 14, 2017
Erotic Couplings

Someday I am going to learn that making a bet with my girlfriend Beth is a lost cause. Not only do I usually lose, but also the stakes never seem to be what I thought they were. Not that she is dishonest; it’s more like she’s unexpected. If she says we are going fishing, I expect to sitting on a lake or river trying to catch lunch. She would be driving m...

Graduate Life Ch. 02

by amandrake on Jul 15, 2020
BDSM

Tom, having lost a bet to his girlfriend, Becky, spent the first couple of days thinking of ways to get out of it. The wager he'd lost was that Becky could persuade his house-mate James to go-down on her, after she and Tom had fucked. Becky won the bet. Tom's forfeit was to have Becky's name tattooed onto his abdomen, just above his cock. The bet was won on...

Bar Bet Weekend

by LiseKLord on Feb 7, 2018
BDSM

Joly and Rina had been friends since elementary school, through high school as well. They had been college roommates and now, five years after graduation, thanks to good jobs, they still chose to share a very nice condo in the heart of downtown. They knew everything about each other, and despite the occasional annoyances any living together relationship migh...

Just Another Lost Angel

by BarracudaSwordfish on Mar 17, 2020
Mature

Prologue Even after all these years, she didn't really know what she was or why she did the things she did. She was like a programmed machine -- programmed to do one thing, and she did it damned well. She knew there were others out there like her, but she had never met them. At least not in a conscious state. Legend had it that succubae and incubi came to...

Booty Shorts

by Jamie753 on Jun 26, 2019
Exhibitionist & Voyeur

Amy lay in bed thinking about how her day had gone. First noteworthy thing that happened that morning was her roommate Cassie telling her it was time to fulfill her obligation for the lost bet Amy had made over the weekend. Along with her declaration Cassie had handed her a pair of shorts and told Amy that she had to wear them all day. Looking over the ga...

Reunion with Annie

by hickmouse on Sep 13, 2017
Erotic Couplings

My phone rang. I didn't recognize the number, but I picked up just the same. It was my old girlfriend Annie, who I had not talked to in years. I've written a few other stories about her. We dated for a couple of intense years when we were in our early twenties right out of school. It was one of the most remarkable periods in my life, and especially my sex li...