Losing Bet Stories

101,365 results
Orientation
Length
Source
Infinite Scroll

Working Out

by Adanaliyik on Oct 15, 2017
Erotic Couplings

A couple of months ago, my wife convinced me to join a fitness club because I needed to get rid of my middle aged spread. I wasn't in bad shape to be honest, since I've never been fat. But I'd had a slight gut since before my wife and I even met. A couple years back, she and I had started working out together at the base, and bringing our son with us. But wh...

Before The Date

by Ashson on Sep 12, 2017
Erotic Couplings

Mary had a date lined up. It wasn't a hot date, more of a get better acquainted date to see where things were going. Seeing she was out of work well before him, Mary had agreed to drop by his flat rather than have him pick her up. Mary came skipping up to the door, anticipating a friendly date, to be greeted by Ron. Not Travis, but Ron, his housemate. Ron...

Texas Hold 'Em

by Charles Petersunn on Sep 14, 2017
Group Sex

I have not submitted any stories in quite some time. I do apologize for that. Life doesn't always proceed as you would prefer. This story was written on the suggestion of a Literotica writer and award winner, Sack. I hope you enjoy my Texas Hold 'Em variation on the card game theme. Some understanding of the rules of Texas Hold 'Em would help, but it's not r...

What's Behind Door Number 2

by pacifist91w on Sep 18, 2017
Anal

(Please don't read this story if you're under 18. Any resemblance of these characters and any actual people is coincidental. Explicit lesbian sex, brief drug references, and profane language within!) *^*^* Three weeks into my first year of college, I saw someone I had hoped I'd never see again, except at reunions to gloat about how great my life was and ho...

Rita & Rhiannon's Bet Ch. 04

by BONNIEBREA on Sep 14, 2017
Exhibitionist & Voyeur

Here is the other version of Rita's Bet that I had mentioned I was working on. When I had first though about the premise for Rita's Bet I was undecided about where to take the story. There were two possibilities that appealed to me. While writing the first idea (published as Rita's Bet) I decided to write the second premise too when I finished, and this is t...

Kelly's Date

by arlene548 on Sep 12, 2017
First Time

I was feeling on top of the world, ready to take my prize. Kelly had been worth all the effort to get her to the edge. It started with a bet, a simple wager and progressed from there. Only five weeks earlier I had bet my best friend Brad $250 that I could nail Kelly before he could nail Sheila. The rules of our game were simple. We had a code we needed to...

The Billionaire's Bet

by texashorror on Sep 2, 2017
Erotic Horror

Conventional rules probably would have suggested that Mojo stand on seventeen. But Mojo was a man who had always gone against conventional rules. Yes, gambling was serious business, but the last hand of Blackjack Mojo would ever play was a win-win, because win or lose, he and Scarlett were going to be half a million dollars richer. The only thing he stood to...

The Boss vs. The Man Ep. 01

by wrestlingisreallycool on Jan 15, 2019
Celebrities & Fan Fiction

Hello there, I hope you enjoy this, this is the first series in what I hope will be a collection of wrestling-focused erotic literature. I have seven different series in mind to start which hopefully will all be unique and interesting. Also, admittedly, this is my first time writing a full-length piece of fanfiction/erotica, so I hope it's not too bad. Anywa...

Logan and Lauren Ch. 14

by Bizzy_Bish on Sep 25, 2017
Interracial Love

"Lauren," I can't fucking take this anymore!" Logan shouted, his wide eyes probing mine, "What the fuck is your problem?" "Nothing," I said with a sigh. In reality, it had been almost a month and I was still feeling all fucked up about dating a future college football player with NFL potential at a football-oriented school like OU. There was absolutely no w...

Roberta & Patrick's Bet Ch. 03

by BONNIEBREA on Sep 17, 2017
Loving Wives

This story is presented in five parts. The story is finished and all chapters have been submitted, so hopefully you should be able to get into the story and enjoy a chapter every day. As always, your comments and observations are welcome. * Patrick, as the winner of the previous game, dealt first. I would have to win two games in a row to pull this out; to...