Losing Bet Stories

101,365 results
Orientation
Length
Source
Infinite Scroll

A Bet's A Bet Ch. 01

by Naked1 on Sep 26, 2017
Exhibitionist & Voyeur

The old saying that you should never bet on anything less than a sure thing is an old saying for a reason. At least that's what Jamie thought as she eyed the small, thin, gold chain dangling from her fingers in the light. He couldn't be serious. Two months earlier, Tom and Jamie had made a wager; they'd bet on the outcome of a stupid baseball game. Truthf...

My Big Mouth

by mikeyt3 on Sep 12, 2017
Loving Wives

I learned a valuable lesson about knowing when to keep my big mouth shut last week. I was watching television with my wife Kim, when the doorbell rang. Kim went to the door to see who it was. It was Zach, a guy in the neighborhood that played video games with me. Hard to believe at 30 I play video games, but I do and they get pretty heated. I am a pretty bi...

Dressing to Please Ch. 01

by HeatherMaureen on Sep 15, 2017
Transsexuals & Crossdressers

I was at a friend's party dressed in a short, tight skirt with a low cut blouse and four inch heels overtop a light green lace garter belt, bra and sheer panty set with sheer black nylons. No one minded as there were a lot of other transvestites there as well! About an hour after I got there a man came in that caught my eye. I don't know what it was about hi...

The Change Pt. 06

by Miah_H on Sep 25, 2017
Transsexuals & Crossdressers

Jerry and Lita got home, and Jerry had one thing on his mind: the big game. Game 7 of the World Series... it all comes down to this. As an Indians fan, Jerry was a little disappointed with the rousing comeback that the Cubs had made, but he still believed they could pull the win. Lita sat down with Jerry for the first part of the game while she ate. Lita was...

The BJ Olympics

by tango0919 on Sep 1, 2017
Humor & Satire

Once a year there is a Food Truck Festival in Newport that I attend with the BF. To some, it's just another early Autumn event. However, to BF and me, it is so much more. The first time we attended, last year, we were amazed by the variety of foods available: fried dough, gourmet grilled cheese sandwiches, fish tacos... However, the truck that we both soug...

The Bet

by Master_Vassago on Sep 12, 2017
Erotic Couplings

It all started innocently enough, a bet, a simple bet between the two of us that would change our relationship forever. Gone would be the simple days of flirting and teasing to the next level of moaning and orgasms and sex. I had been flirting a while with Jennifer, this cute girl that I played against in some pool tournaments with me. Well one night while...

Spence The Pornstar Ch. 01

by DickThePimp on Dec 3, 2018
Celebrities & Fan Fiction

This is a perverted sleazy fucktastic parody series... It ain't real Stars Of This Story : James (Me) Kim Kardashian (Herself) Beyonce (Herself) Spence (Spence Ulchin Of The Sitcom King Of Queens) Professor Gaia (Herself) Christy Canyon (Herself) "Babe, will you and Beyonce please go to the Adult Convention in San Diego with Spence and try to help...

Ten Dates

by Dyrtytailz on Sep 12, 2017
Loving Wives

My wife and I are happily married. We share all our fantasies together. She's hot, and I'm comfortable with myself. Anyway lately we've been busy. We've shared a couple of fantasies and had some good sex, but not like we used to. We agree with one point. We don't want to be single, but we do miss the newness. While discussing our point with a single male fri...

The Bet

by ukresearcher on Sep 13, 2017
Loving Wives

You must all have heard about the gambler who having lost all of his money in a card game then stakes his car in an effort to recover all that he has lost. He loses and, unable to imagine life without a car throws the deeds to his house into the pot. The losing run continues. The gambler is wondering how to tell his nubile young wife that they have nowhere t...

Golf Bet

by Jamie753 on Dec 25, 2018
Exhibitionist & Voyeur

Editor's note: this story contains scenes of incest or incest content. *** I have an aunt who is a stone fox. She's 5'7", dark brown hair, works out daily, and could literally be a photographer's model. She also has a magnificent pair of ta-tas with gorgeous, well-defined, dark pink nipples. Now you're probably wondering how I know about my aunt's nipples...