Lost Bet Stories

182,389 results
Orientation
Length
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Infinite Scroll

The Bet on the Biggest

by dirtyjoe69 on Sep 12, 2017
Toys & Masturbation

I am a big woman; some would call me a SSBBW (super sized big beautiful woman). I weigh, well I am not going to tell you what I weigh but let's just say it is more than the average Joe can lift. I have a massive chest; each boob would cover most people's heads. And I have been cursed with two gaping holes. Both my wide asshole and my gapping cunt can easily...

Losing the Bet

by talkmedown44 on Sep 13, 2017
Loving Wives

"They stink at free throws!" That was the start of this adventure. Kind of unexpected to tell the truth. When our group gets together we often make silly bets with weird payouts. We're all generally too poor and cheap to make bets about cash, so we like to come up with dares or actions or sometimes even chores the loser has to do. One time I had to wash a b...

Wife Loses Poker Bet on Nude Day

by andtheend on Sep 16, 2017
Exhibitionist & Voyeur

Wife must do whatever her husband wants. Husband beats his wife at poker and she must do whatever he wants her to do, whenever he wants her to do it. "Well, that's it. I win and you lose our little Nude Day bet," said Robert to his wife, Donna, with a big ear to ear grin. "Better luck next time, when we make another bet on Labor Day," he said with a laugh....

Fingered in the Bar

by luke_stcy on Sep 24, 2019
Loving Wives

Stacy and I were at a casino in Las Vegas and were going to be taking in one of the shows. When Stacy was getting ready for the night, I noticed she had chosen one of her very short and sexy dresses. This dress had a very low-cut top which meant the bra was going to stay behind. I also noticed that she decided to go without panties also. After the show wa...

Bet Everything?

by Cat5 on Sep 26, 2017
Exhibitionist & Voyeur

"As a point of fact, you three could never be good gamblers," I said in a somewhat flippant manner. "Dave, you are so full of bullshit, it's coming out your ears," responded Amy as she glared at me. I didn't come to their apartment looking for a fight. In fact, I wasn't planning to see them at all, but I had bumped into Janet at the front door; she was str...

Dressed for Success

by Joseki Ko on Sep 16, 2017
Transsexuals & Crossdressers

I’ve been a professional wrestler for about two years now. And no you haven’t seen me on TV I’m not that good yet. I wrestle in the Ohio Valley Training Center. That’s were all of us kids go to train for the big shows. RAW or SMACKDOWN. One of the things I enjoy most about this job is the testosterone level of my fellow workers. Everybody has an attitude an...

Roberta & Patrick's Bet Ch. 01

by BONNIEBREA on Sep 13, 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. * My arms went around Patrick's neck, my nose nuzzling into his cheek. I left a kiss there as I pulled back a bit and s...

Certainties

by oggbashan on Sep 14, 2017
Humor & Satire

************************************************* Copyright Oggbashan March 2016 The author asserts the moral right to be identified as the author of this work. This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. This story in...

Playing Poker

by Adanaliyik on Sep 18, 2017
Group Sex

My wife Elif and I have been friends with the couple next door, Dave and Figen, for about 6 years. Dave and I are both Americans, and work for the same company, and our wives are both Turkish which is how our friendship started. We do the normal friendship things that couples do, that is go out drinking on Saturday, go on picnics when the weather is nice, an...

Charlotte's Bet

by toocold on Sep 26, 2017
Group Sex

Charlotte would admit, in hindsight, that it had been a reckless bet to make, especially when her friends started to escalate the forfeits. She couldn't even use the excuse that she was drunk as she was driving home from the party so hadn't touched a drop. She'd always been pleased with herself – a confident, beautiful 19-year old girl with soft, mostly natu...