Size Bet Stories

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Dude Looks Like a Lady

by trainman2k on Sep 1, 2017
Humor & Satire

As you read this, please don't believe that this how I think women act. This is just an attempt at some odd humor. ========================= Having lost a so-called 'friendly' bet at the bar one night recently, I was obligated to dress and act as a woman for a day. The only good thing was that I could do it on a day off since it would be unexplainable for...

The Bet

by KittyandBear on May 20, 2019
Transgender & Crossdressers

Chapter 1 What on earth was Charles thinking? I was only giving him some good-hearted teasing, and then he challenged me with this bet. And the result seems to be pretty obvious. No offense to Charles, but there is no way he could win. There had to be some trick, and Charles was always the clever one. And the worst part is, there is no walking back from thi...

Sexy Golf Wager Ch. 02

by Tall_Stranger on Sep 1, 2017
Group Sex

Chapter 2: The Next Hole Jack and Allison smiled as Brent and Robin made their way to the next tee from their trip to the woods. Jack and the dark tanned Allison could see the flushed faces and tiny beads of sweat on the pair as they approached. "Have a good time?" asked Jack. "A man has to pay off his bets." is all Brent replied and winked at well-endowe...

True Blue

by Stiffness on Sep 16, 2017
Interracial Love

This friend of mine named Rocky was always first in line to look at my private photo album. My wife is a knockout and on occasions I have managed to gather some very hot pictures of her in surprising situations. Rocky would sit there with a hard on bulging in his pants gawking at her pictures. He would shake his head and comment how he wished he could get...

A Woman's Wager

by andtheend on Sep 13, 2017
Transsexuals & Crossdressers

A man who lost a bet must dress as a woman and discovers he likes it. "Pardon me, Madam," said Ed trying to hustle his shopping cart down the aisle by a very large woman. With her carriage blocking one side of the aisle, she was hunched over a shelf with her big ass blocking the other side of the aisle. When the woman turned to move her carriage out of the...

Anal Bet: My Ass For A Car

by dirtyjoe69 on Sep 12, 2017
Anal

I should have known it was going to happen sooner or later. I had been attending the local college for three years and made quite the reputation for myself. My name is Jenny and I am the college slut. I am not a skinny girl; as a matter of fact most would probably consider me fat. I am 5'6 and weigh 230lbs. That is 230lbs of sex machine though. I found out i...

Betting On A Sure Thing

by pullmepushyou on Sep 25, 2017
Mature

I had just finished my freshman year of college, having somehow existed through months of frustration. My grades were excellent but my sex life was a failure. With hormones pumping throughout my body at breakneck speed, and a goodly amount of attractive girls running around campus suffering with the same condition, one would have thought that I would have co...

Lynn Buys New Shoes

by LynnGK on Sep 18, 2017
Exhibitionist & Voyeur

My husband is a bastard. And I love him. He calls me a bitch. And he loves me. Our marriage and our sex are both perfect. We often make bets on football and basketball games. Not for money -- but for sex. Sometimes I win and sometimes I lose. When I win, I make the bastard pay. Last week I teased and tormented him an entire evening before I finally let him j...

Everybody Wins

by ShyHottie on Sep 1, 2017
Group Sex

There I was, a 35 year old 'Mrs. Robinson' sitting amidst a table full of young 20-somethings. They were all men, except for the friend who had invited me, Tabitha. We had been invited to join their table at Ernie's Pub. So, far off into the corner we trotted with our drinks. The conversations were plentiful though uninteresting. At one end of the table, a...

Big vs. Biggest

by HornyHenry on Sep 11, 2017
Erotic Couplings

A story based of a suggestion from Sirhugs. Thanks for the inspiration. * It was early Friday morning. Sean was lying on the couch in his girlfriend's college dorm apartment watching TV in only his boxers, when her roommate, Janelle came in, wearing only a sexy little baby blue nightie. "Hi, Sean? How's it going?" Janelle greeted him with a smile. "Hi, J...