Lost Bet Girlfriend Stories

201,764 results
Orientation
Length
Source
Infinite Scroll

Ann: A Love Story Ch. 13

by mimaster on Sep 14, 2017
Erotic Couplings

Over the previous week, my life had unexpectedly become a paradox. No longer lovelorn, or more accurately, sex-lorn, I found myself in a position I wasn't prepared to deal with. It was Friday, and I couldn't help but reflect on the changes I had experienced since the last one, when I was driving to Michigan to begin an adventure that would change my outloo...

Prepare To Be Boarded

by ~calypso~ on Aug 18, 2017
Exhibitionist & Voyeur

Jack was the first one to get naked. Jack was always the first one to get naked. Jack was the first one to get drunk, the first one to get stoned, the first one out the door, and always, always, the first one to get naked. He was a leader that way. We were all sailors, hikers, campers - people who loved the outdoors. But Jack was a true outdoorsman, a snow...

From Terror to Pleasure

by soncurious on Sep 2, 2017
Erotic Couplings

I love the summer, everything seems to slow down and I can relax a bit. It also means that I can get a late evening walk in after my kids go to bed without it being cool enough to need a jacket. I usually have a set route I take so I know how far I'm walking. When I can walk it in a faster time, I add a couple of blocks. I've been trying to get myself back i...

The Wager

by quinnwilson45 on Jan 12, 2021
Cheating Spouses

"I am positive I could get her in the sack. I think you’re just afraid to make this bet." That was Justin, my Best friend talking. We’re both in our early twenties now and for nearly ten years we’ve known each other our relationship has been intensely competitive. When we were boys we constantly competed against each other in everything from school...

Open in Reader

Breaking Balls

by balboa_rain on Sep 15, 2017
Loving Wives

"Yeah, I called you a gagger, Ron! You never get a hit when we need it, and that error in the third inning let in three of their runs!" "Give me a fucking break. You're always looking to pin reasons for losing on someone else! Why not try looking in the mirror for a change? Who's got a higher average, huh?" The party was still going on around us as Tony an...

Grow Your Own Girlfriend!

by Carnevil9 on Sep 13, 2017
Sci-Fi & Fantasy

"Go out with YOU? Are you crazy? I wouldn't go out with you if you were the last creature -- and I do mean creature -- on the face of the Earth! Get a life, loser!" With that, Gloria Van Arsdale turned on her heel and strutted off. Harold watched as her pert blond ponytail and sweatpants-clad butt wiggled down the quad and out of his sight. "So much for the...

Super Bowl Sluts...

by SlutProblems on Feb 4, 2020
Group Sex

It was the 4th quarter of the biggest football game of the year; the Super Bowl! The snacks were long abandoned and the tension was extreme. I could feel the excitement in the air as I sent up a prayer to let the Philadelphia Sharks win over the Glendale Fireballs. I had made quite the bet on this game, probably because I'd had too much to drink even before...

Cheryl and Mike

by tnx4nuthin on Oct 5, 2020
Loving Wives

This fantasy occurred to me as my GF Cheryl and I were lying in bed one morning, and I was fingering her pussy, trying to make her come. She was still sleepy and though she kept getting close again and again, we had trouble getting her over the top. Eventually we did, and her orgasm lasted nearly a minute. In the meantime (almost an hour) I alternated betwee...

Winning Answer

by BrettJ on Sep 16, 2017
Anal

Hello readers. This is a sequel, of sorts, to "With Two You Get ... ". I am trying some new ideas these days, and hope you enjoy them. As always, feedback is appreciated. Lauren stormed into the living, stamping her heel-clad foot and tossing back her long, jet-black hair. "This sucks !" she scowled. Lauren was a loving partner, a good friend and a wonder...

Spying on My Girlfriend

by DarkrSide on Mar 27, 2019
Exhibitionist & Voyeur

EVERY CHARACTER IS OVER 18 YEARS OLD "Which bathing suit should I pack?" my girlfriend Lori asked. I stuck my head out of the bathroom. In one hand she held a modest one piece bathing suit and in the other she had what could only be described as a bikini. I couldn't help but laugh. "I'm sure your students would love that one," I said as I pointed to the b...