‘lost bet’ stories

A sibling rivalry changes after a lost bet,

After dirty handjob, straight guy becomes gay hottub fantasy.

She plays a strip game in public - she wants to lose.

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

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

He joins a pajama party as an honorary girl.

Brady loses a bet and becomes Brandi.

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

A girl loses a game of strip poker.

Frank enters a high-stakes tournament.

Strip Poker game with stepsisters does not go as planned.

Beth loses another bet with Titus.

She loses the bet and loses again.

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

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

Loving wife gets punished after losing game night.

Wife loses bet and becomes a slut.

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

Bartender at a biker bar gets a side hustle.

Conservative wife makes a foolish bet and loses.

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

Steve plays strip monopoly with 3 girls during a blizzard.

Wife must follow hubby's ever command.

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

Bitter rivals make a bet with everything on the line.

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

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

What happens when you WIN a bet with a Futanari.

The poker club ups the ante.

Losing Quaterback made slave to Winning Team's Cheerleaders.

Enslaved to the strippers.

A misplaced bet leads to public humiliation.

Gambler takes a bet to win his wife.

A rude and mean woman loses an ax throwing bet.

A nice suburban milf has a submissive experience.

Naked in the office where you are the only man.

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

Continued exploits of guy who loses a bet.

Handsome Gigolo is enslaved by rich MILF & her niece.

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

Bored housewife loses bet.

A Bet is a Bet - make your bet, lose your bet, pay your debt.

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

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

A Xmas board game leads to unexpected sexual delights.

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

A bet with some sorority girls goes wrong.

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

Depressed, she bets more than she can swallow!

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

Winner gets to use loser for their enjoyment.

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

A lost pool game leads to slavery to a sorority house.

Andy loses a fixed game and is forced to dress as Mandy.

New girlfriend loses bowling bet and spends a weekend naked!

A young woman learns not to bet on the Super Bowl.

If you are going to bet, be prepared to pay.

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

A small change creates humiliating consequences for all.

A bet is lost.

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

An unexpected foursome in Tokyo.

A lost bet goes much worse than Bernie imagined.

Part 2 of the Lost Bet Series.

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

Home unexpectedly to find the girls naked.

Leslie finds losing a bet a little hard to swallow.

Tina gets kicked in the crotch by her roommate.

Ana's dare takes her to unchartered territories.

Conservative wife unknowingly pays her bet via hypnosis.

Pool playing girl bets more than she should.

Mia discovers the joys of big cock.

Sarah begins to understand how powerful the curse is.

Sandrine and Danielle have a disagreement.

Four Psychiatrists have their way with my conservative wife.

Athletic girls bet it all and one comes up short.

A game of table tennis gets much more interesting.

Wife makes a bet and has to pay up.

You make a stupid bet, you live with the consequences.

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

Roberta risks anal to try to explore her dominant side.

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

He bets more than she is willing to risk!

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

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

Christine fills promises messes up and decided on her future.

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

A woman loses a bet to her cousin, and has to pay in public.

Sarah made to work as a French maid.

Two coeds are taken home by a strange man.

Should Rob and Holly allow Jim to hypnotize her again?

Risky bet costs a red head a lot...

A bet on pool leads to a long week of servitude.

Cariny and friends wager on Trivial Pursuit.

My wife's most humiliating experience.

A winner claims his prize.

Extended description of my wife's most humiliating evening.

It's Sara's turn to get her kit off.

Luna and co. visit the ranger station.

It starts with a lost bet that results in CFNM and more.