Lost Bet Stories

182,389 results
Orientation
Length
Source
Infinite Scroll

The Bet

by ukresearcher on Sep 13, 2017
Loving Wives

You must all have heard about the gambler who having lost all of his money in a card game then stakes his car in an effort to recover all that he has lost. He loses and, unable to imagine life without a car throws the deeds to his house into the pot. The losing run continues. The gambler is wondering how to tell his nubile young wife that they have nowhere t...

The Game

by Psishadow on Sep 25, 2017
Exhibitionist & Voyeur

Doug showed up for the game not sure what to expect. They had played strip poker several times before, but Jenifer promised this time would take the game to another level. He was greeted by Jenifer who introduced him to Lynn, Michelle, and Nikki. Jenifer said that they were still waiting on Paul and Tiffany then everyone would talk over the rules of the nigh...

Marti Ch. 01: The Streak

by PericulumFabula17 on Jan 22, 2019
Exhibitionist & Voyeur

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** This is a prequel to my Repo'd series (which I promise that I will update soon). It gives backstory to Marti, a mailgirl in the Repo'd story whose character, although currently minor, will become more important in coming chapters. However, as this story is set in 2025, six...

The Bet

by latexcd69 on Sep 12, 2017
Transsexuals & Crossdressers

My friend Cristina and I were just sitting around watching porn. It's something we do for fun now and then. Believe it or not, it has never led to anything. A scene came on where a guy was put in a wig and satin nightgown and fucked by a beautiful blond dominatrix with a strap on. We laughed at what an ugly girl he made and somehow it came up that I had a gi...

Betting at Pool

by drsalt on Sep 16, 2017
Fetish

We went to the Eagles Club for a drink and some pool. Brandy had driven us there because I had already had a few beers. When we got there drank coffee because she knew I would probably have several more. Chad was tending bar that night and there were only two other people sitting on the stools. We said hello to everybody and Brandy bought some pull-tabs. Ou...

Strip For Your Love

by hrshie40 on Sep 13, 2017
Group Sex

Tonight my plan, no my fantasy would come true. I had been working on it for months and the day had finally arrived. The strip club owner had been bribed and the dancers primed. 5 of our friends would be there to watch. Tonight I would see you dance on stage. The thought or seeing you dance at a Titty bar had come to my mind early in our relationship. The t...

Nerd and the Jock Ch. 02

by godeep123 on Aug 31, 2020
First Time

Before I could take another breath, his lips were on mine. I froze but at the same time was surprised by how just the mere touch of lips have created sparks all over my body. My entire body tingled from top to toe. I tried to unfreeze my body and move away from him, but my traitor body already started giving in. After what felt like an hour, realization hi...

Drinking Could Get You In Trouble Ch. 01

by HeathRowinOhio on Sep 2, 2017
Exhibitionist & Voyeur

I had been grinding away at the divestiture document for nearly ten days. There had been numerous conference calls between the States and the UK and I was nearing completion but I still had a ways to go. I was wearing out but the work needed to be completed. My wife Sue was a bit upset with my lack of attention on her. Since it was a Saturday and I continue...

Letter To Tommy Ch. 3

by Linda Jean on Sep 16, 2017
Group Sex

Then Josh said "you know I have an idea, I'll bet you right now that your cunt is not just wet, but you are sloppy wet, I bet you cunt is open and ready for a cock." I asked "What happens if I win the bet?" He said "Well mom first off I know you can't win this bet, you are just a natural hot blooded bitch that can't get enough cock, you have been settling...

You Bet Your Ass!

by RedMonika on Aug 14, 2011
Erotic Couplings

“Hello, I am Guy Goldstein and welcome to ‘You Bet Your Ass’, the game show the pits four sexy constants willing to risk sexual humiliation on television for the chance to win cash prizes. Today’s show is Jocks vs. Geeks, and we certainly have a ‘stacked’ show for you tonight, if you know what I mean.” Samantha takes a deep breath as the stage director gives...

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