• Adult Confessions
    — Embarrassing Moments —
    Playing X-Box with my older step-sister was one of the only things we did together growing up. We never hanged out together otherwise is what I mean. We got along, but things between us were always competetive. We liked to place little bets as we played... loser has to do the dishes alone tonight... loser has to take out the garbage for a week... that sort of thing.

    Pretty soon things escalated, to the point where the loser was doing the chores for the other one all week long. Our parents knew we were making these bets and were okay with it as long as we didn't bet for money.

    But soon things got out of control because we started adding little embarrassing things to the bets that the loser would have to do. One week I lost and had to wear these really embarrassing one piece pajamas while I did the chores. The week after she lost and I made her wear her cheerleading outfit while she did the chores.

    Then one week we decided to up the stakes. The loser would have to wear whatever the winner wanted around the house... for a week. Aside from having to wear our school uniforms when we were at school... the winner would have complete control over the other persons wardrobe... for a week!!

    I thought it was a great idea... until I lost. Totally not seeing it coming, I ended up wearing dresses and skirts all week long whenever I was home. And to make matters worse, I had to wear panties to school under my uniform.

    Point of the story... never make bets with older step-sister(s)!!!
    #1506 — Comments (12) — 10/3/2009 at 1:15 AM — That's Juicy! (1) — That's Lame. (0)
  • 1
    Take solace in the fact that you sometimes won. I never got to make bets, or had an opportunity to get even. My step-sister proved to me real quick that she could kick my butt and took every advantage. She made me do her chores, and would embarrass and humiliate me for her entertainment. I never wore panties or anything like that. But I do remember her grabbing me one time and wrestling me on the floor. The next thing I knew she was pulling my clothes off and I ended up wearing a dress. I was 8 or 9.
    10/5/09
  • 2
    I once lost a bowling bet to some girls I worked with at a grocery store when I was 16. I had to wear a pink tutu in the store on my night off.
    10/7/09
  • 3
    What kinds of dresses and skirts, and did you wear them outside the house?
    10/8/09
  • 4
    LOL That's pretty funny.
    You were 8 or 9, how old was your stepsister?
    What did the dress look like?
    10/8/09
  • 5
    Sounds like a funny bet. What would the girls have had to do if you won?
    Did you wear the tutu over your pants or were you in full ballerina drag with tights?
    10/8/09
  • 6
    She was 10 or 11. The dress was white with pink lace and all poofy and girly. I was mortified at the time.
    10/8/09
  • 7
    Wearing the tutu was the bet, no matter who lost.
    No tights but no pants either. I was bare legged.
    10/8/09
  • 8
    I guess you were but I bet the girl was enjoying it!
    10/9/09
  • 9
    LOL Good for you in being a good sport and going through with it.
    10/9/09
  • 10
    Yes she was. She showed me to her friend as if I were her new toy or doll. It was humiliating.
    10/10/09
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