‘lost bet’ stories

Extended description of my wife's most humiliating evening.

My wife's most humiliating experience.

Black cop stops wife while driving nude after losing a bet.

What happens when you WIN a bet with a Futanari.

Gray breaks a bitch realtor.

Alison participated in a game of poker.

Leslie finds losing a bet a little hard to swallow.

Cassie wins a wager and the pets gather for a sex party.

Sarah is always on the losing side of the wager.

A dare leads to a city streak, which leads to more naked fun.

She exposes her naked rear to tennis ball serves.

Coed loses a bet and is forced to streak a football game.

I beat an older dude in bowling and he entertains us.

Naked in the office where you are the only man.

In a park, I change & play tennis with Ryosuke & other guys.

Bitter rivals make a bet with everything on the line.

Ryosuke takes me swimming, then we play squash.

Cocky womanizer & a confident co-ed clash. Winner takes all.

Wade loses a bet, streaks, and runs into complications.

A new law, a lost bet, and public humilation.

Looking for a fight, busty little goth gets in over her head.

Subbie girl completes another highly sexualised task.

Wealthy lady bets all on cards.

Loving wife gets punished after losing game night.

Christine fills promises messes up and decided on her future.

A small change creates humiliating consequences for all.

Bartender at a biker bar gets a side hustle.

Home unexpectedly to find the girls naked.

A group of friends try to get free drinks by posing as girls.

A rude and mean woman loses an ax throwing bet.

A sibling rivalry changes after a lost bet,

Showing up late comes with a punishment...

Mark and Claire up the ante, and show their feelings.

A nice suburban milf has a submissive experience.

Winner gets to use loser for their enjoyment.

I lost a bet to my coworkers and had to do a dildo show.

Sarah begins to understand how powerful the curse is.

Rivalry between two pool hustlers comes to a climax!

Catherine Blanchard discovered in the worst way how bad luck.

Back to School Memories.

Brady loses a bet and becomes Brandi.

A story of a walk I had to take when I lost a bet.

Wife makes a bet and has to pay up.

A sexy wife is introduced to the hotwife life and more!

After being sissified by Ethan, I go back for more...

A lost bet to a friend leads to a humiliating sissification.

New girlfriend loses bowling bet and spends a weekend naked!

You've got to pay up when you lose a bet, right?

Tina gets kicked in the crotch by her roommate.

He didn't think losing a bet would turn him into a play toy.

Short foot story told in 3 different word counts.

Part 2 of the Lost Bet Series.

For years we had talked about expanding our experiences, now.

Ana's dare takes her to unchartered territories.

A sub agrees to be punished only to win bet and become dom.

Mia discovers the joys of big cock.

Susan's stupid bet is getting her in deep trouble.

A winner claims his prize.

I (straight) bet on a blowjob and swallow more than pride.

Oh Susan, the brainy blonde has gotten in over her head.

Stacy lost a bet to a stranger and had to pay up.

How it all worked out and where we go from here.

Holly knowingly bangs the poker guys.

Rob starts to work out his revenge on the doctors.

Four Psychiatrists have their way with my conservative wife.

Should Rob and Holly allow Jim to hypnotize her again?

Rob has to tell Holly what happened to her at Lou's Tavern.

Conservative wife unknowingly pays her bet via hypnosis.

Conservative wife makes a foolish bet and loses.

Depressed, she bets more than she can swallow!

Reserved wife accepts her husband's challenge, and her own.

He joins a pajama party as an honorary girl.

Cariny loses at strip poker, playing 'for keeps.'

Cariny and friends wager on Trivial Pursuit.

Beth loses another bet with Titus.

Amy "studies" with Suzie to win a bet against Samantha.

With higher stakes, she makes a bet she can't fail to lose!

Bored housewife loses bet.

Luna and co. visit the ranger station.

He bets more than she is willing to risk!

Hoping to win his money back, he bets her innocence!

A game of table tennis gets much more interesting.

Avery wins date night bet & takes Hank to the gloryhole.

Traveling musician enslaved to her rival by the king.

The poker club ups the ante.

An unexpected foursome in Tokyo.

Sexy Street Racer Dulce loses far more than just her ride.

College girl loves cards a bit too much and learns a lesson.

Athletic girls bet it all and one comes up short.

Risky bet costs a red head a lot...

A bet is lost.

A girl loses a game of strip poker.

A lost bet goes much worse than Bernie imagined.

Pool playing girl bets more than she should.

Can pain be holistic? Cyd thinks so. Beth does too.

Steve plays strip monopoly with 3 girls during a blizzard.

Handsome Gigolo is enslaved by rich MILF & her niece.

Losing Quaterback made slave to Winning Team's Cheerleaders.

Strip Poker game with stepsisters does not go as planned.

A bet with some sorority girls goes wrong.