This experience may contain mature content, as flagged by the community.
Please click away if you do not want to see this content.
To report inappropriate content, please email us.

I Lost a Bet and Had to

Personal Stories, Advice, and Support 280 People


    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
    13 Responses Apr 14, 2011

    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

    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...
    51-55, M
    Jan 20, 2013

    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
    Jul 1, 2012

    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
    1 Response Apr 4, 2013

    Whale Tail Lost Bet Pt.

    1. I recently made a bet a friend and the loser had to do what ever the winner wanted them to for a day. To make a long story short, I lost. She didn't do anything at first. But, about three days later, she said we were going to go shopping. Once we got to the store, she told me...
    hiiiia hiiiia
    18-21, F
    2 Responses Dec 26, 2014

    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
    1 Response Sep 18, 2011

    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...
    BeautysHerName BeautysHerName
    22-25, F
    6 Responses Apr 20, 2012

    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

    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
    8 Responses Jan 14, 2012

    ***** 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
    Sep 26, 2012


    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
    3 Responses Dec 9, 2008

    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

    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

    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

    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

    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
    2 Responses Nov 9, 2013

    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...
    deleted deleted
    1 Response Apr 19, 2011

    Lost a bet to my brother

    when we were kids and I had to *****, run out the front door and shake my junk at the neighbors across the street. I was so scared but I did it cuz I had to, the beatings and endless ridicule I would have faced from my brother and my friends for reneging on a bet would have far...
    Joeychestnuts4 Joeychestnuts4
    31-35, M
    1 Response Mar 8, 2016


    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
    1 Response Dec 12, 2008

    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

    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  
    Josie06 Josie06
    56-60, F
    8 Responses Feb 26, 2010

    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
    41-45, M
    Oct 10, 2013

    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

    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
    41-45, M
    2 Responses Oct 9, 2013

    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

    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
    66-70, M
    1 Response Apr 4, 2011

    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

    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
    Dec 17, 2012

    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
    22-25, M
    1 Response Apr 23, 2013

    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
    1 Response Jun 29, 2013
More Stories