Win Money Stories

103,381 results
Orientation
Length
Source
Infinite Scroll

Naked on the Internet

by Hellen_S on Aug 19, 2017
Exhibitionist & Voyeur

I love feedback on my stories. Please vote for me and please remember: It is hard to write in a foreign language! * I used to spend some time in the Internet playing games online. I mostly do this on lazy afternoons just after the midday relax and before the night clubbing. My favorite game is backgammon, since is simple and based on luck. I am quite good...

Side Bet

by Drackman on Sep 17, 2017
Loving Wives

It's not my fault. I didn't even want to come to fucking Vegas! But somehow Charlie talked me into it, and then our "romantic" honeymoon turned into just him playing cards all the time and leaving me to my own devices. I guess I should have seen it coming. I should have listened to my friends when they told me not to marry a man 10 years older than me, tha...

Rachel and Me Pt. 07

by schmoe90 on Dec 23, 2019
Exhibitionist & Voyeur

I was playing poker online against a couple of friends. We were playing for real money, and were down to just me and Steve, as Jason had gone bust. We were teleconferencing so we could trash talk each other while we played, so when there was a knock at the door, I told them I'd just be a minute. I opened the door, and it was Rachel. She was wearing a baseba...

How To Win Playing Blackjack

by BOSTONFICTIONWRITER on Sep 11, 2017
How To

Are you feeling lucky? Are you hoping to win big at the casino? Well, of course, if you are naturally lucky, then there is no need to even read this story. If I had your luck, I'd run to the nearest casino and sit at a Blackjack table and say the magic words. "Hit me." Now, if you are like the rest of us and lose money when gambling, then this story is for...

Chess Game Ch. 02

by urbanslut on Sep 13, 2017
Loving Wives

Chapter 2 - The Middlegame When I left the colonel's house, I was elated. I now had 3200 rupees. I could finally buy my beloved summer dress. I decided to go to Bandra right away, in case someone else bought the dress before me. As I got ready to go to Bandra, I paused awhile. There was going to be a rematch. And what if I lost? Maybe I should wait till the...

Strip Poker, Reimagined

by lionshell on Sep 1, 2017
How To

Strip poker is a classic game, and for good reason. It can be a slightly risqué party game (try playing a round of old-fashioned Spin the Bottle after every winning hand) or the perfect way to set up a long night of affection between, or among, consenting adults. Watching someone else take off a piece of clothing every few minutes can be a great tension-buil...

A Gamble Too Far

by jujou2006 on Nov 27, 2017
Fetish

Friday night is poker night at the Salon. The Salon's owner, Giorgio, runs the poker games for the money and deals the cards for guys most of who fancy themselves to be professional poker players. In reality, they are just guys that are gambling addicts in the making. If they ever showed up in Vegas, Atlantic City, or New Orleans, they would lose the kid's t...

Poker Night

by KevinandNina on Sep 13, 2017
Exhibitionist & Voyeur

After all these years, I was looking forward to my class reunion. I had moved out of town about 6 weeks after graduation and never looked back. After a stint in the service, I started doing construction and within a few years started my own business out in the suburbs. In addition to the guys that work on the construction side, my small construction/real e...

Montana Jake

by western_tales on Sep 13, 2017
Romance

Today seems like a good day for some pool. I have returned to my home town, after being gone for 4 years going to college. I was at a local pool hall, bar, and restaurant combination like you will have in these small Nevada towns. It even has a casino in it. I have just beat 2 college boys, that thought they would be better at playing 8 ball than I was. I wa...

Prices and Risks

by Jappio on Jul 30, 2019
Exhibitionist & Voyeur

Prices and Risks Part 1 By Jappio Patrons sat in chairs and stools lining the bar and tables. Drinks and food were served to many there, but none had been to the most popular table for some time. Merriment and banter had first been exchanged, but started to turn to discourse over time. A sharp dagger cut into the table, wedged in the wooden boards, a met...