Size Bet Stories

142,710 results
Orientation
Length
Source
Infinite Scroll

The Skater

by SizeQueenSupreme on Sep 12, 2017
Fetish

Yes the sizes in this story are extreme and absurd. It was a fan request that made them as such. If you want to join my new fan club, write me via the CONTACT page on my profile. * I hated it when they first built the thing. It came up almost over night, and when the construction noises faded I thought I'd have peace. No such luck. The sounds of jackhammer...

A Wife Agrees Ch. 01

by Amavoyeur on Feb 13, 2018
Loving Wives

Author's note: These chapters reveal some of the exploits of an expert card-player, Greg, who uses his skills to get his way with married women. He never discloses that he has played poker at competitions in Las Vegas and, as such, has an overwhelming advantage over amateur players. Each chapter features a different female, written from her point of view. A...

A Lost Bet Ch. 01

by amarasfantasy on Sep 12, 2017
Transsexuals & Crossdressers

I was afraid. I knew I'd lost a bet with some guys I didn't really know and I had no idea what they had planned. It was stupid of me to have made the bet, but I just knew I'd win. We'd been sitting around playing poker and I was almost out of chips. I was biding my time though, watching my stack dwindle as I waited for my hand. Then it came, a straight flush...

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...

The Misogynist Ch. 06

by carvohi on Sep 16, 2017
Romance

Cheryl hadn't been able to suck that awful of man's penis. She'd thrown up, and fled to the room Turner had designated as hers. Then just as she was slipping into her clothes to escape this terrible place she heard the door slam behind her. Turning she saw Turner. He was just standing there, smiling. He had a belt in his hand. He slowly, almost solemnly loc...

Trapping Samantha

by wifetrapper on Jul 14, 2020
Loving Wives

Sometimes life's greatest adventures start out in a bar. This probably isn't one of them. I have gotten the reputation of being one to bring out the worst in wives. Including my own apparently. I had a failed marriage after finding my wife was sleeping around. I managed to keep my cool and laid my plans to wreck her life and move on with mine. Since then I...

The New Church Roof Pt. 02 Ch. 03

by WillingWolf on Sep 15, 2017
Novels and Novellas

Jane eventually arrived down to the breakfast table in a long t-shirt looking like she had imbibed one or two too many the night before. I provided her with coffee and a Danish plus half a gallon of orange juice and waited for the post mortem. I thought that the best defence of the fact that she had probably caught me being sucked by a host of girls and fu...

Naked Embarrassed Tom Ch. 02 - Exposing Tom, All Inclusive

by tosoaronhigh on Dec 31, 2017
Exhibitionist & Voyeur

Tom, Kevin, and John climbed off the plane into the humid heat of the Dominican Republic for their week long all inclusive vacation. The boys had always talked about taking a trip like this, but until now, there was always something that stopped them from going. An hour later the boys made their way from check-in to the suite they'd be calling home. Kevin...

Costume Party Switch

by jackie_em on Oct 24, 2018
Transgender & Crossdressers

I should know better than to bet on football games, even when there's no money on the line. I am Mike, 25 years old and a guy. My girlfriend is Michelle, the same age as me. We had been dating for some time, and had moved in together, after sleeping together pretty regularly. There was a Halloween party coming up that we planned to go to. I am 5'6" and 135...

My Fantasy Weekend Ch. 02

by Pro_Ball_Player on Sep 15, 2017
Fetish

This is the second chapter of "My Fantasy Weekend". You might find it beneficial to read chapter 1 because all these chapters will lead into the next. Unfortunately, the first time I tried to post this chapter it was rejected as being garbled. So, that means chapter 3 and maybe chapter 4 would be posted after this chapter, which is too bad because this cha...