I Lost A Bet And Had To Wear Girls Clothes

Personal Stories, Advice, and Support 150 People

    Makeup Bet

    I made a bet with my sister that I could beat her in a race around my block the if I lost she got to put makeup all over my face everyday for a month if she lost I got to shave her head I lost so the first day she did the my makeup then she said you look like a girl why not...
    Flash123456 Flash123456
    18-21, T
    2 Responses Oct 15, 2013

    I Recently Lost A Bet And Have To Dress Totally As A Woman...For Over A Year!

    Back during Basketball Season My Sister and I made a bet on which team would win. I was so sure that the Oklahoma Thunder would win that I got into a bet with Sis that stated the loser of the bet had to do whatever the winner said for a whole month. As the series began Sis and I...
    1trj 1trj
    41-45, M
    20 Responses Jan 4, 2013

    LOL Sometimes it's hard to fold a royal flush

    just so you'll be the one having to dress up. In the end you wind up being the winner anyway and depending on the bet and the people involved it can be a lot of fun and a safe way to test how others will react to your desire to dress and appear feminine.
    amandatrane1 amandatrane1
    51-55, T
    2 Responses Oct 29, 2015

    The Betting Dress

    My name is Patrick and I am going on a trip to visit my cousins for the week. I woke up in the morning has my mom was yellinng for me. I looked at the time and we were suppose to be leaving, so I jump out of bed and got dressed. I didn't care about going because I had only girl...
    Jacklyn13 Jacklyn13
    61-65, M
    7 Responses May 1, 2012

    Lost A Bet To My Older Sister

    Alright one day me and my sister were really bored and my sister asked me if I wanted to do a bet so I said yeah and asked what do u want to bet then she says who ever can hold their breath longer under water so we got our bathing suits on and went into our pool then I thought I...
    deleted deleted
    26-30
    2 Responses Aug 27, 2012

    I recently lost a bet on playing fifa with my

    older brother... His girlfriend is allowed to apply makeup on me now, and I have to dress as a girl for 2 weeks now ... I have to wear: A bra, panties, shorts, pink top, and makeup.... We're also going to the supermarket one day .... But we need some more punishment ideas! We...
    deleted deleted
    26-30
    Mar 16

    When I was around 11 I would make a bet with my

    cousin on a game of darts and loss on purpose so she would dress me up. Completely make-up, bra, panties, pantyhose, slip, dress, and high heels. She would then put curlers in my hair and even paint my nails. I had to stay in caricature for the rest of the day I loved it.
    RJMC65 RJMC65
    46-50, M
    Mar 4
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