Gambling Stories

2,929 results
Orientation
Length
Source
Infinite Scroll

Twist of Fate

by stickivicki on Sep 13, 2017
First Time

The closed heavy draperies helped blanket the room in darkness. Outside the wind howled with its wolf-like voice. Just that sound made the house seem colder than it really was. "Put your head down and rest," he whispered. "You know you want to. Things will be better in the morning, I promise. Everything always looks different in the light of day." He hated...

Jan's Vegas Trip Pt. 01

by cuckold308 on Sep 23, 2019
Interracial Love

Viva Las Vegas, our Red Shoe Diary (Part I) Now finally back in our hotel room, I began to reflect on the evenings events. Jan in the bathroom, showering, washing off the final remnants of all of sex she received. I picked up her thong, it was soaked with the many loads of cum that had drained from her cunt. Realizing that unless rinsed out soon, they would...

Fever

by Comshaw on Sep 17, 2017
Loving Wives

Tom took a deep breath as he picked up the last card. Holding his breath, he slowly turned it so he could see it. His heart pounded as he realized it was a 2 of spades. He slid it into his hand along with the other two deuces and the two nines he held. He tried hard not to grin from excitement. He glanced at the small pile of chips in front of him and almost...

Super Slut Ch. 02

by LordWriter7 on Sep 14, 2017
Sci-Fi & Fantasy

In Allston there were three major gangs. The Crowns, the Aces, and the Blue Devils. The gold Crowns were the most powerful and dealt in extortion and protection, the Blue Devils ran most of the garages and chop shops around town and ran illegal races or courier runs. The red Aces were the most violent, owning the gambling and sex trade. Alisa looked down at...

Shooting The Moon

by SEVERUSMAX on Sep 15, 2017
BDSM

I couldn't have heard that right, of course. Another guy in a game of cards with me, wanted to raise the stakes in a way that I had never even considered. Nor did I really think about it in advance, but the man was a gambling addict. Robert Cullen, sharp as a tack Wall Street stockbroker and relative newlywed, had just offered me his pretty wife Lindsay as c...

A Twist of Fate

by stickivicki on Sep 12, 2017
First Time

The closed heavy draperies helped blanket the room in darkness. Outside the wind howled with its wolf-like voice. Just that sound made the house seem colder than it really was. "Put your head down and rest," he whispered. "You know you want to. Things will be better in the morning, I promise. Everything always looks different in the light of day." He hated...

Welcome to the Neighborhood

by Stormbringer on Sep 25, 2017
Interracial Love

"Here we are," said Fred, turning the moving van on to Washington Avenue. Amber reached over to grab his arm. "I hope this is a good idea." "Everything will be fine," replied her husband. "This is all my fault. If it wasn't for me, we wouldn't need to do this." "Honey, it's alright. Things will work themselves out." "Are they all black?" "As far as I c...

The Fight I Could Never Win Ch. 00

by NarcissusRex on Sep 15, 2017
BDSM

For the first time in a long time, I genuinely felt good after a weigh-in. There was not a shred of doubt in my mind that this was an opponent I could handle. I had seen him fight before, which was far from worrying in and of itself. To top it off, he had clearly overdone his training, trying to cut down his weight too far too fast and paying for it in stren...

A Slave to Socks Ch. 01

by AnimatedSocks on Sep 15, 2017
Fetish

"You got to be kidding me." Ellie shook her head disapprovingly, an index finger and thumb coming up to her face to rub the temples lightly. She had thought spending this Saturday night out with her best friend would have resulted in the usual college activities: Shopping for the latest fashions, clubbing and making the boys jealous, or hell even just a nigh...

A Proper Scottish Wife Ch. 22

by Thors_Fist on Mar 5, 2018
Novels and Novellas

This chapter contains oral, anal and vaginal sex between consenting adults. Thorburn discovers Teárlag's betrayal when she confesses her acts on behalf of Blackthorne. We are approaching the end of this tale. Only a few chapters remain. I am having visitors for the next 12 days, so it may be 3 weeks before the next chapter is ready. Enjoy. ***** Isobel wok...