‘lost bet’ stories

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lost bet 

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A Bets a Bet

What happens when you WIN a bet with a Futanari.

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Alison's Adventures in Marriage Ch. 04

Alison participated in a game of poker.

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The Bet

Leslie finds losing a bet a little hard to swallow.

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A Different Kind of Sex Toy Ch. 47

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

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Sarah - After Playing Pool

Sarah is always on the losing side of the wager.

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Barcelona Dare

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

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Naked Tennis Ball Target

She exposes her naked rear to tennis ball serves.

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Marti Ch. 02: The Mother of All Streaks

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

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My Older Naked Entertainment

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

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Naked at All Female Office: Day 00

Naked in the office where you are the only man.

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Tennis in the Park

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

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The Bet - Rivalry and Humiliation

Bitter rivals make a bet with everything on the line.

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My First Time Playing Squash

Ryosuke takes me swimming, then we play squash.

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A Tale of Surrender and Humiliation

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

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Wrong Turn, Right Hallway Pt. 01

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

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Femdom Policy

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

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Thicc Big Titty Goth Girl Loses Bet

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

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Lost Bet

Subbie girl completes another highly sexualised task.

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Lady Gambler

Wealthy lady bets all on cards.

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Audrey's Game Night Pt. 01

Loving wife gets punished after losing game night.

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Girl on the Golf Course Ch. 08

Christine fills promises messes up and decided on her future.

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The Ripple Effect Pt. 01

A small change creates humiliating consequences for all.

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Above It All

Bartender at a biker bar gets a side hustle.

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My Naked Guests

Home unexpectedly to find the girls naked.

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Ladies Night

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

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Ax Mountain

A rude and mean woman loses an ax throwing bet.

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Sister's Lost Bet

A sibling rivalry changes after a lost bet,

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I Was Not Late

Showing up late comes with a punishment...

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The Bet Ch. 02: Double or Nothing

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

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Suburban Milf's Transformation

A nice suburban milf has a submissive experience.

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Stay!

Winner gets to use loser for their enjoyment.

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The Stupidest Bet

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

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Sarah and the Gypsie's Curse Ch. 03

Sarah begins to understand how powerful the curse is.

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Right on Cue

Rivalry between two pool hustlers comes to a climax!

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Catherine Blanchard at The Casino R

Catherine Blanchard discovered in the worst way how bad luck.

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Regression Therapy

Back to School Memories.

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A Game of HORSE Pt. 01

Brady loses a bet and becomes Brandi.

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A Walk of Shame

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

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Her First Gang Bang Ch. 06

Wife makes a bet and has to pay up.

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Mandys Introduction

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

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A Lost Bet Leads To Sissification Ch. 02

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

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A Lost Bet Leads To Sissification

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

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Bowlarama! Ch. 01

New girlfriend loses bowling bet and spends a weekend naked!

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BJ Bet

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

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Tina Lost The Bet

Tina gets kicked in the crotch by her roommate.

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Paying Off a Bet to my Wife Ch. 01

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

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Lost Race: A Story in 3 Lengths

Short foot story told in 3 different word counts.

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Lost Bet Pt. 02 - First Step

Part 2 of the Lost Bet Series.

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Lost Bet - Tentative Steps

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

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Ana's Toll Booth Dare

Ana's dare takes her to unchartered territories.

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Superbowl Bet and Payoff

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

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Happy New Years

Mia discovers the joys of big cock.

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Stupid History Bet Pt. 02

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

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The Wager

A winner claims his prize.

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Straight to the Bottom Pt. 01

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

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Stupid History Bet Pt. 01

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

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Fingered in the Bar

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

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The Psychiatrist Ch. 08: Epilog

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

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The Psychiatrist Ch. 07: Poker Night

Holly knowingly bangs the poker guys.

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The Psychiatrist Ch. 06: The Aftermath

Rob starts to work out his revenge on the doctors.

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The Psychiatrist Ch. 05: The Deed

Four Psychiatrists have their way with my conservative wife.

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The Psychiatrist Ch. 04: Proposition

Should Rob and Holly allow Jim to hypnotize her again?

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The Psychiatrist Ch. 03: The Next Day

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

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The Psychiatrist Ch. 02: The Payoff

Conservative wife unknowingly pays her bet via hypnosis.

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The Psychiatrist Ch. 01: The Bet

Conservative wife makes a foolish bet and loses.

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Isle of Seduction

Depressed, she bets more than she can swallow!

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Kristen Tests Her Boundaries

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

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Sissy Sidney and Sister

He joins a pajama party as an honorary girl.

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Cariny Ch. 02: Cariny's Best Client

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

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Cariny Ch. 01: New Category

Cariny and friends wager on Trivial Pursuit.

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The Unwanted Houseguest Rebooted 03

Beth loses another bet with Titus.

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Strip Game Addicts Ch. 11

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

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A Bet is a Bet Ch. 03

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

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Mother Trucking Forfeit

Bored housewife loses bet.

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Luna vs. The Camp Ch. 02

Luna and co. visit the ranger station.

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A Bet is a Bet Ch. 02

He bets more than she is willing to risk!

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A Bet is a Bet

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

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Ping Pong Paddling

A game of table tennis gets much more interesting.

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Avery Dirty Date Night 01 - Friday

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

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KR: Hannah on the Kingsroad - Ch. 01

Traveling musician enslaved to her rival by the king.

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Friendly Rape Poker

The poker club ups the ante.

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Sophie Takes Tokyo

An unexpected foursome in Tokyo.

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Downfall of a Street Racing Vixen

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

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A Gamble Too Far

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

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Race to the Bottom

Athletic girls bet it all and one comes up short.

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A Game of Chance

Risky bet costs a red head a lot...

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Checkmate

A bet is lost.

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Jennifer: Strip Poker

A girl loses a game of strip poker.

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A Naked Short - The Water Slide

A lost bet goes much worse than Bernie imagined.

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She Should Have Quit When Ahead

Pool playing girl bets more than she should.

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A Separate Life

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

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Snowed In

Steve plays strip monopoly with 3 girls during a blizzard.

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The Trapped Boytoy

Handsome Gigolo is enslaved by rich MILF & her niece.

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The Big Game

Losing Quaterback made slave to Winning Team's Cheerleaders.

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Strip Poker

Strip Poker game with stepsisters does not go as planned.

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The Big Bet

A bet with some sorority girls goes wrong.

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Kicking the Habit

A bet over quitting drinking leads to a summer of nudity.

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One Pump Chump

Enslaved to the strippers.

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Pool Shark

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

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