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.
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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...
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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...
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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...
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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...
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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...
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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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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...
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Miscellaneous
100 years ago, a law was passed, making it so that every bet made between individuals would be legally enforced so long as both parties agreed to the terms. The punishment depends on the terms of the bet, but would typically be much worse than the actual loss of the bet. The consequence of losing a bet can be anything so long as it does not result in permane...
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by
HornyHenry
on Sep 11, 2017
Erotic Couplings
A story based of a suggestion from Sirhugs. Thanks for the inspiration.
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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...
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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...
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