Bad Bet Stories

179,314 results
Orientation
Length
Source
Infinite Scroll

Losing the Bet

by talkmedown44 on Sep 13, 2017
Loving Wives

"They stink at free throws!" That was the start of this adventure. Kind of unexpected to tell the truth. When our group gets together we often make silly bets with weird payouts. We're all generally too poor and cheap to make bets about cash, so we like to come up with dares or actions or sometimes even chores the loser has to do. One time I had to wash a b...

Dark Angel Comes to Town...Again #03

by SusanJillParker on Sep 16, 2017
NonHuman

Witches and wizards never die. They are here now and are here to stay. ...And so is Satan. Warlocks, Wizards, and Sorcerers #1, 2, and 3 Taking this naming of witches a step further, in the way that woman can be witches, men can be warlocks, wizards, and sorcerers. How else can one explain the explosive success of Simon Cowell, Ryan Seacrest, and Randy Ja...

Lose the Bet, Lose Your Clothes!

by B3AUTY_BEAST on Sep 11, 2017
Exhibitionist & Voyeur

It was a cold winter evening in East Tennessee and we had been trapped indoors for far too long. What we needed was a little excitement, a little fun, a little naughty time. I asked if you were up for some excitement. I knew I didn't need to ask. You were the type of girl that would try anything at least once if I just asked. You are one of the most stunnin...

Slut: Suzi the Sun Lounge Slut

by NeilMc123 on May 15, 2018
Exhibitionist & Voyeur

This all started out as a drunken dare. Suzi and I had been drinking at the hotel bar as a particularly poor cabaret act tried to entertain the hotel residents. It was a sub par performance from the act, which was surprising as most of the acts on Tenerife are usually very entertaining. Now I was fully aware of how bad the entertainment was, and although th...

He Was The Best Man

by oralguy82 on Sep 13, 2017
Erotic Couplings

My wife's first lover was my best buddy and best man at our wedding. He was my neighbor and the one I started sucking back when we got out of high school and were working a job running power lines across some desolate parts of Canada. Gary was smaller than me in every way, shorter and leaner, except he had a 7 inch cock to my 4 incher. Even though he was...

Roomate's Girlfriend

by bronston22 on Sep 3, 2017
Erotic Couplings

This is a true story although I have changed the names to protect the guilty. I am not proud of cheating with the girlfriend of a brother in arms but in the end, no harm was done. * I served as a Lieutenant in the Army in the late 1980s and early 1990s as an infantry officer at Fort Bragg. I lived with a fellow officer and friend in a two story apartment o...

Southern Sounds

by angienator3 on Sep 14, 2017
Erotic Couplings

Angela carefully put down the lap top as soon as he had signed on. The last words struck her as odd though. She had been used to the regular instant messenger banter but not usually from Louis. She still remembered him as a young cocky 20 year old boy to her own self-conscious and easy to please 19, standing in uniform at the front of her house as he got rea...

Just a Poker Chip

by Sean Renaud on Sep 14, 2017
Anal

"Where are we going?" Karen asked staring out the window. She'd been sitting quietly in the passenger seat of her Toyota RAV4 for the last hour. She hated the outfit she was wearing, it made her feel. . .dirty. The fishnet skirt came down to the middle of her thighs but it was meant to be worn over another skirt, not alone. Alone it didn't conceal her flesh...

Betting on Darts

by BlackManWins on Jan 14, 2019
Interracial Love

My name is Zack, and this is a true story about how I lost my ex-girlfriend to my ex-best friend. It all started when I got in a bar room conversation with my, at the time best friend, James. James was a tall athletic black guy, I roomed with in college. He's a big talker about his exploits with women, especially white women. He claimed they were all hot for...

Strip For Your Love

by hrshie40 on Sep 13, 2017
Group Sex

Tonight my plan, no my fantasy would come true. I had been working on it for months and the day had finally arrived. The strip club owner had been bribed and the dancers primed. 5 of our friends would be there to watch. Tonight I would see you dance on stage. The thought or seeing you dance at a Titty bar had come to my mind early in our relationship. The t...