Can a woman answer this?

I lost a bet with a woman at work. I only made the bet because A. I figured she wouldn't make me do it for more than a day, if at all and B. Even if she did I figured my boss wouldn't allow it. Apparently, I was wrong on both counts. Anyway, I have to wear a skirt or dress and heels as long as she wants. How long do you think it will be/should be? What would you do if you were her and being encouraged buy co-workers?


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What Girls Said 3

  • a.) lesson learnt
    b.) why wouldn't you're boss let you wear a dress skirt or heals? that would simply be discrimination
    c.) she's not the boss of you, you don't actually have to do it if you don't want to.
    d.) what's wrong with wearing a skirt or a dress? heels are a pain in the arse/back/legs i wouldn't advise anyone to wear those

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    • Just embarrassing. Besides, she is talking about a month or more of dressing like a woman.

  • I'm sorry but this never happened. You just made this up. Every now and then a transvestite with a fetish comes on and posts this exact question.

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    • Good for them. Not the case here. But thanks for taking the time to call me a liar.

    • No, you did make this up. It's the exact same question. Like 10 times. This scenario has never happened in real life, it only exists in the fantasy world of transvestites, which I'm guessing you are?

  • Walk in with the clothes on but bring a change of clothes

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