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I Lost a Bet and Had to

Personal Stories, Advice, and Support 261 People

    About To Lose A Hairy Bet!

    I made a bet with a young female friend of mine. We bet all the time. Nothing sexual, just silly stuff. Things like loser has to change the baby's poopy diaper 10 times, or winner gets to drop 3 eggs down losers pants, and break them, or loser has to wear a diaper for an hour...
    sissyrachel48 sissyrachel48 61-65, M 2 Responses May 2, 2012

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    I Lost A Bet

    One day I was with my friends 1 girl and 2 guys we were playin pool and we made a bet the two guys were a team and me and the other girl were a team if we lost we both had to ***** down and get a hangin wedgie and make out with each other if the guys lost they had to do the same...
    Wedgieismylife Wedgieismylife 18-21, F 5 Responses Apr 20, 2012

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    Lost Bet = Total Embarrassment (and Total Fun!!!)

    I was visiting a friend in Laughlin Nevada last week and we started to argue over some stupid show on television. The argument turned into a bet. The loser had to do whatever the winner said for 24 hours. Long story short...I lost! She ordered me to ***** naked. I figured this...
    deleted deleted 26-30 Jul 1, 2012

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    Win Win All The Way

    I lost a sporting bet, well we had a few.... One i enjoyed most losing was i had to allow her to cuff me, which she did and she gave me a little show just to tease me even more
    charliek75 charliek75 36-40, M 1 Response Oct 9, 2013

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    Gloria's Party

    THIS IS THE STORY--please help if you know anyone in southeast PA or northern MD....please!!! Hi Paul! So you say you don't remember too much about Saturday? Poor you! Let me tell you everything then. I will try to tell all. When I planned to have a few of the girls...
    flpala321 flpala321 36-40, M 1 Response Oct 10, 2013

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    ***** Poker And Dreams

    I would love to lose a bet that would require me to do something naked in front of a group of women. The closest I came was losing ***** Poker. I was in college and it was 3 guys and two girls. I and one other guy were totally naked with one girl topless and the other in her...
    DroopysExpFun DroopysExpFun 36-40, M 1 Response Sep 26, 2012

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    H.O.R.S.E.

    A friend in college and I were very competitive and we made a lot of bets with each other. One of them was with a game of H.O.R.S.E. If he won I'd have to do a cartwheel outside on the main grass area where everyone in college hung out. I can't do cartwheels, and he knew...
    yoyy yoyy 26-30, F 2 Responses Dec 9, 2008

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    Get Dressed By My Girlfriend For One Week.

    Me and my girlfriend had a bet about a local sports game while we had a week off, who would lose had to get dressed by the winner for one week. So my chosen team played really crappy and I lost. I accepted that I lost and tought let's just get this over with. The first day we...
    Tim007 Tim007 18-21, M 1 Response Apr 23, 2013

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    Thong Underwear On The Beach

    If you read my earlier story my sister was still mad at me for wearing her thong. Next week my parents went on vacation. She took me to the beech. She made me come with her into the girls bathroom( what ever) she then took me into a stall. Then she pansted me and ran out of the...
    john4793 john4793 22-25, M 1 Response Apr 1, 2011

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    Crossdressing Bet

    My neighbor is a gorgeous blonde. she has the perfect body and is insanely cute. She loves to gamble so i used that to my advantage and taunted her into a bet i was sure to win. The bet was simple if i could bet her in a game of Chess she would wear something sexy for me and...
    PrincessNikkishia PrincessNikkishia 18-21 1 Response Nov 9, 2013

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    Naked

    As most of you know i am a pretty attractive girls with big breasts and a nice big ***. ONe day i was hanging out with my guy friend at his house. We were playing pool. We decided we would bet on a game. We would do anything the other said if he/she won. So i lost. He made me...
    thonglover90 thonglover90 22-25, F 16 Responses Apr 14, 2011

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    A Game Of Pool

    Where I went to school, in our final year we had a pool table for our year group, and there were set rules that had carried on from year to year. Namely, that if you were whitewashed (beaten without potting a single ball), then you had to run around the table naked. Eventually...
    webdare2 webdare2 18-21, M 2 Responses Feb 26, 2012

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    Don't Bet If You Don't Want To Lose!

    A long, long time ago, my wife and I were watching a hockey game when our team let in a bad goal. I commented that these guys were losers and we were wasting our time watching them. She got pissed and asked if I cared to bet on the outcome of the game. "How much?" I said. She...
    phph phph 61-65, M 2 Responses Apr 4, 2011

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    Wont Bet Again After This

    one night at the club i bet i could see more vodka than billy the other bartender that might, so as the night was close to and end he had wooped my *** hard core so i said what do i have to do, he said you have to find the most unatractuve girl in the place and go home with...
    chrisyoung chrisyoung 22-25, M 2 Responses Apr 19, 2011

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    Hockey Game With A New Crowd

    Oh my god I looove making bets, always nudity-related ones lol. I'm a hockey fan and I love making bets on games. This is the first one I actually LOST. I'd just moved to a new city a month before. I made friends quickly but my circle of friends had known each other for years and...
    deleted deleted 26-30 2 Responses Apr 4, 2013

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    Mommy Knows Best

    I am known for clowning arond and making bets every once in a while with friends and what not. They were never for as high a stakes as this one was. My mom made a bet with me over the stanley cup. I am not a huge hockey fan but, I like to watch it every now and then. Before the...
    natimus007 natimus007 26-30, M 2 Responses Jun 25, 2011

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    Have Sex With A 16 Year-old Girl (best Experience Ever!)

    I was 18 years-old. My first spring break home from college, my parents wanted to take us to Florida to stay with some friends of theirs they hadn't seen in a long time.  My dad's friend was a very successful optometrist who owned and operated a bunch of offices in Florida...
    budrojr budrojr 36-40, M 2 Responses Jul 3, 2013

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    Lost Bet To Mom And Her Friend

    My mom and I have always had a good relationship. We play jokes on each other all the time. We also do bets with some pretty wild forfeits. Once when I was about 25 my mom had her friend Lucy over and we were watching House. My mom asked what the name of the black doctor was...
    susan321 susan321 41-45, F 10 Responses Jan 14, 2012

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    Dodge Someone's Jealous Girlfriend

      Several years ago me and a friend made a bet with two of our guy pals during the Super Bowl. I'm such a fan... I CAN'T tell you who was playing! I picked the underdogs of the year just to crinkle the guys' feathers. If we gals won, the guys had to fix us supper. If...
    emerald emerald 36-40, F 7 Responses Apr 13, 2010

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    My Sisters Thong

    I steal my sisters thong when shes not home. I love them and get hard and **** when there on. I made a bet with my bf who also does this with his sister. we would both wear our sisters thongs everyday. The first one to get caught had to do a couple things. 1. Get a thong...
    john4793 john4793 22-25, M 2 Responses Mar 23, 2011

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    Spend The Evening Naked And Serve Drinks

    Some 30 year ago I was at one of my girlfriend 's friend birthday party and I stupidly entered into a bet with my girl friend. I did bet she could not drink her beer faster than me. She was not a heavy drinker so I thought I would easily win. I suggested that the loser perform a...
    danyweb danyweb 46-50, M Jul 14, 2013

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    Nearly Nude Servant One

    Been trying to get a bet going with my wife for a while and she finally gave in. We had a wager on a WII fit game - one round no arguments and no backing out. If she lost she had to do the housework naked and as she is not good at these games I think she had resigned herself to...
    lazydawg lazydawg 51-55, M 2 Responses Oct 29, 2011

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    Lost Bet

    The craziest thing I had to do on a lost bet was ********** until I came in plain view of my roommates. That was exciting!
    Orlandofun Orlandofun 41-45, M 1 Response Apr 11, 2012

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    My Friend Surprised The Hell Out Of Me

    I had known my friend for almost 4 yrs. We would party together alot laugh and have fun together. Allthough she would often joke about sex and nudity nothing had ever happened between us so far. One day she asked if i wanted to make a bet with her on are local NFL team. The...
    singledadinfinley singledadinfinley 46-50, M 1 Response Dec 17, 2012

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    Should I Lose A Bet It Would Be Like This (TG Captioned Images)

    I would be sooooooo haappy to lose a bet with this ending for me! From http://juliesforcedfemmecaps.blogspot.com/?zx=5e758be6a65d740c  
    Josie06 Josie06 56-60, F 9 Responses Feb 26, 2010

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    I Lost One

    Me and my friend alyssa made a bet on a football game.I lost. she said she didnt take her panties off for 2 weeks. so she took then off and i had to smell then. then she shoved her panties in my mouth pushed me in the corner, took her pants of and rubbed her butt in my face and...
    johntobi12 johntobi12 22-25, M Sep 25, 2011

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    Had To Go To Nude Beach With Wife

    I lost a bet with my wife and was forced to take her to a local nude beach. She is very pretty and has a fantastic figure, complete with perfectly shaped large breasts. I, on the other hand, even though I have a nice firm smooth body, have a very small penis. She forced me to...
    chris1208 chris1208 26-30 2 Responses Jun 29, 2013

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    Do One Embaressing Thing,

    THERE WILL BE MORE STORIES FOR THIS GROUP! So it was a Saturday and my sister, Belle and I were just sitting around. So she said, “How about we drink 4 gallons of water and not use the bathroom for a full 24 hours?” I said yes and we put down some bets. The loser had to pay...
    Wedgiegirl203 Wedgiegirl203 22-25, F 2 Responses Sep 6, 2013

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    Comando

    I lost a bet to Leo one morning and he hid my knickers, so I had to sit through Uni in my jeans and no pants for the whole day. I did try and steal a pair of his boxers but it was too much effort to fight him for them. Hangovers and bets and alcohol don't mix.
    deleted deleted 26-30 2 Responses Dec 12, 2008

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    Naked For the Evening

    I lost a bet to my girlfriend on who would win a soccer game, and it was decided before the game that the winner would be allowed to give the loser instructions for the rest of the evening that they must follow. After the game was over, and once we got back from dinner, we got...
    fun3some1985 fun3some1985 22-25, M 5 Responses Sep 20, 2009

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    Birthday Suit

    i was at my aunt's house with my brothers my sister wasn't born yet. I was 6 and i loved go-fish so i told my aunt i bet i can beat you in go-fish she said what you wanna bet, i thought and said loser gets in their birthday suit, i knew i was going to lose because i saw my aunt...
    deleted deleted 26-30 3 Responses Sep 18, 2011

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    I Lost A Bet And They Made Me Their Slave

    Recently I was contacted by an old friend, I always had a crush on Diane but never told her, so getting back in touch was a great way to maybe be more than just friends, so when she invited me out to her place for a card game, I said "Sure, but I'm not that good at it, in fact I...
    KEYPER KEYPER 51-55, M Jan 20, 2013

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