Lost Bet Stories

182,389 results
Orientation
Length
Source
Infinite Scroll

The Bet

by nvrbored on Oct 30, 2018
First Time

"How about that guy?" My girlfriend was pointing at a guy walking up to the door of the rest area. I'd lost a bet, and she takes paying off bets very seriously. I'd bet her that she couldn't get me off by giving me a blowjob in less than 10 minutes. I was so sure I'd win. See...she'd given me lots of blowjobs. And don't get me wrong, they all felt great! Bu...

Football Wager

by Azuldrgon on Sep 2, 2017
Erotic Couplings

(another fantasy involving football) As Judy was driving towards Jeff's house, she thought aloud to herself why she still went over there to watch the Bears play. Judy looked again at her favorite football outfit she wore. A white half shirt that scarcely covered her busom with a giant Bears logo on the chest was under her denim jacket that matched the mini...

Dude Looks Like a Lady

by trainman2k on Sep 1, 2017
Humor & Satire

As you read this, please don't believe that this how I think women act. This is just an attempt at some odd humor. ========================= Having lost a so-called 'friendly' bet at the bar one night recently, I was obligated to dress and act as a woman for a day. The only good thing was that I could do it on a day off since it would be unexplainable for...

A Wager Gone Wrong Ch. 02

by CatherineH on Sep 16, 2017
Loving Wives

Thank you for the many positive remarks. Despite the early morning hours which I had snuck down to the system to work on the submission and subsequently left several typos and mistakes the patience that you expressed (for the most part that is ) is much appreciated. A little background for this is as such: The wager is true. I lost a bet for the purpose of a...

I Don't Want to Spoil the Party

by Harddaysknight on Sep 12, 2017
Loving Wives

It was New Year's Eve and I was really enjoying myself. In my entire life, I had made two solid friends and they were standing in the room with me. We were in Tom's basement shooting pool and drinking beer while our wives chatted upstairs. I had moved back to Allentown a year ago, after living and working in Philly for fifteen years. Ray had gone to Stanfor...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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Your Evening

by Jappio on Aug 19, 2017
Exhibitionist & Voyeur

Part 1 You turn your head up towards the hot stream of water coming towards you. You let the shower head rain warmth over your body, desiring the steam may somehow help clear your head. You hoped an extra warm shower may calm your nerves, but no such luck could be found. You heavily sigh, stepping from the shower. To avoid making a mess, you of course wrap...

Louise Submits Ch. 01

by bydasea on May 16, 2018
Exhibitionist & Voyeur

Hello, my name is Louise Baker. I'm a Mathematics' teacher in a very elite high school. All my students are very intelligent seniors and are chosen for my class because of their grades and ages. They must have a 4.0 grade average and be 18 or over. Yes, some students are 18 while still in high school. I am also one that used to be in this type of class and...

Bar Bet Weekend

by LiseKLord on Feb 7, 2018
BDSM

Joly and Rina had been friends since elementary school, through high school as well. They had been college roommates and now, five years after graduation, thanks to good jobs, they still chose to share a very nice condo in the heart of downtown. They knew everything about each other, and despite the occasional annoyances any living together relationship migh...

Bet Gone Wrong

by trev1 on Aug 19, 2017
Exhibitionist & Voyeur

Being a 23 year old female, slim, lovely B cup breast, great body to match and it being such a lovely day, I should have been at the beach in my tiny bikini getting a lovely tan. But my dam car was at the garage getting fix, so I was stuck at home for the day Watching TV on a boring Sunday afternoon was not my idea of fun but what's a girl to do when she is...