Win Money Stories

103,381 results
Orientation
Length
Source
Infinite Scroll

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...

His Promise

by morningjewel11 on Sep 16, 2017
Romance

"I guess it's time for you to go, huh?" she asked. "Yeah, it is...I'll miss you Cassy, I'll come back for you, I promise." he said "I'll miss you too Gabe," tears rolling down her eyes she hugged him with all her might, gave him a kiss on the cheek before running back into her house, up to her room and flopped onto her bed. Gabe stood outside and watched...

Aaah! I Am Nude In Public 3 & 4

by Hellen_S on Sep 26, 2017
Exhibitionist & Voyeur

Hi again! This is the continuation of the story "Aaah! I am nude in public 1 & 2". If you haven't read this one perhaps you must start from there! I surely hope you will love the story and vote for me! I love encouragement! Kisses, Hellen_S *********************************** Session 3: The plan and the lessons Julie was thinking how to get even with Eri...

First Time...Even For Barbara

by andtheend on Aug 17, 2017
First Time

There's a first time for everything, especially for winning, even for Barbara. "Today is my birthday, Sunday, October 31st. Happy birthday to me. Happy Halloween to everyone," said Barbara for no one to hear. Already a little bit drunk, she sat alone again. Alcohol her only friend, she had suddenly taken a liking to Cosmopolitans. The cranberry and lime ju...

Take Me Out...At The Old Ball Game

by RichardHardy on Sep 17, 2017
Text With Audio

* * * * * Click Here to listen: .mp3 format or .ogg format. (9 min/mp3) * * * * * We like to make side bets. "Snide bets" we call them. There's no money involved. Our favorite form of payoff involves sex—usually oral—delivered by the loser to the grinning winner. Snide bets. This one involved Game One of the 2015 World Series. Don't ask how I got the ti...

A Chess Story

by Senna Jawa on Sep 16, 2017
Romance

My name is George, I used to be a single father. My two kids joined a school trip so I in turn was free to join Andy and John in John's mini to a weekend Swiss, my first tournament. All four of us studied at the same department, and the three of us were frequenting a local chess club. The fourth traveler was Cindy herself, the cutest girl ever. Why she volun...

$250,000.00 Secret

by curiousgeorgette on Sep 17, 2017
Mature

On my webcam I watched Bethany scratching the lotto ticket with the penny she found in the parking lot. She squinted to read the year. How ironic. 2001, Canada – 1 Cent. The Maple Leaf waving at her. The copper so shiny and new. Untarnished. Leaning back on the sofa she strokes her clit and feels the moisture leak from her pussy down to the rosebud of her...

The Tiger Within

by MidnightDream on Aug 19, 2017
Exhibitionist & Voyeur

When I was in college, a fraternity on campus held an annual raffle to benefit two local charities. The year before my freshman year, they raised $25,000 selling $5 tickets. The hook was that each ticket entered you into a lottery for a grand prize of $5,000! That was a huge amount of money to a student like me. Needless to say, I scraped together the $5 for...

Transformation and Titillation Ch. 01

by SNEZ_Writing on Sep 24, 2019
Sci-Fi & Fantasy

Beginning in the late 2020s, a strange rumor began to pop up on forum sites. Mysterious posts would appear and then disappear an hour later. They would advertise something called, 'Transformation and Titillation' claiming it was the best game show on the internet followed by a hyperlink and a warning that only those eighteen and older could view the content....

One Night Date Ch. 03

by tighttushy on Jan 23, 2019
Anal

Before we left the place, Satish couldn't decide whether to fuck my pussy, my ass or my mouth, so I ended up deciding for him and began with a blowjob, then I told him to fuck my pussy but with one condition, that he wouldn't rush through it, that he would take it slow, real slow and make me cum twice. Once I had cum twice, I wanted him to fuck my ass so tha...