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Thread: He Crossdressed for Halloween and Looked Really Good

  1. #1
    New Member
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    Dec 2022
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    He Crossdressed for Halloween and Looked Really Good

    Has anyone had a friend or relative that dressed as a female for Halloween and looked really good? Not only were you surprised they dressed up, but that they could pass?

    Do you remember what they wore? Did you wish you were them that day?

    I?ll never forget a friend in jr. high. I walked in to class that morning (I think it was first period) and he was sitting in the first or second row dressed as a girl. While he didn?t have a wig, his short brown hair was styled like a girl, makeup, earrings, bracelets, a stuffed strapless bra under a woman?s T-shirt, a denim skirt that went to above the knees of his bare legs, girls white socks and his sneakers.

    He looked amazing and I told him that he looked good. He thanked me with a shy smile.

    When asked, he told the teacher that it was both his mother and sister?s idea and they dressed him up. I knew the bra was strapless because I patted him on the shoulder before I said hello and didn?t feel a bra strap. I think it was his mother?s bra but everything else probably came from his sister.

    To make a long story short, he got a lot of compliments (especially from the girls) and I don?t think anybody was mean to him (at least I hope nobody was mean). I think the attention became too much for my shy friend and he was completely out of drag at lunch time.

    Did you know someone that looked really good on Halloween? Do you remember what they looked like?

  2. #2
    Hot Geezer Girl docrobbysherry's Avatar
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    Sep 2007
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    Orange County, Calif.
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    Me!|

    Halloween is the only time I can go out with a mask. And, as such I've passed a number times.

    Unfortunately, as soon as I speak the cats out of the bag!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

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