How do I pull off crossdressing?

I recently lost a bet with some friends, and I have to cross dress to the mall >.<. I used to be able to pull it off, but, you know, puberty and everything. I still only look slightly feminine. Any tips? You can check out my pics for reference if you wish. I just don't want to look stupid, and I especially don't want people to know I'm a guy, talk about trashed reputation.


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Most Helpful Girl

  • Wear anything, But just put on some good make-up. Like heavy eye-lashes, and stuff, If you have a sister or a Girlfriend ask her to help you out. Borrow some heels, Braid your hair. wear full sleeves something and do not stuff your chest, just wrap a scarf on your chest which would give it that look. I think that would be enuf. the key is in moderation. if you try too hard to look a girl you mite look something else.

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What Girls Said 4

  • Sure it was a bet, and not a dream come true? Relax, I'm not teasing, but just asking. I happen to have a soft spot in my heart for guys that crossdress, have had a lot of experience with them, so that was why I asked. It's hard for crossdressers, as there's still such a stigma in todays society. I feel bad for them. Guys who crossdress risk facing much scorn and ridicule, and always feel forced back into the closet. Do you have any good friends, especially female ones, that you can confide in, that are willing to help?

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    • It was a bet xD. I will admit, I've been in a dress more time than desired, but it's because I grew up with all girls. It's never been enjoyable for me.

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    • Michelle, you are absolutely amazing... wow.

    • You're sweet, thanks.

  • Maybe puck your eyebrows to get an arch? Good Luck if a guy tries to hit on you though ^.^

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  • Check out a book on Amazon that is at the top of the list right now for feminizing men. It's called, "Feminizing Men - A Guide For Men to Achieve Maximum Feminization. by Barbara Deloto. It will help you to be your most feminine.

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  • aw that sucks dude ahahha. You already have the long hair. So that is a plus. Get but pads, water balloons for boobs, a girdle to cinch you're waist in, and don't forget to where lots of jewelry!

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    • Where can I get a girdle and what type of jewelry? I'm only 17, so I'm not too sure how much a girl my age would wear. And yeah, it does suck.

What Guys Said 4

  • Why not embrace it and go all out? People will just assume you're a guy who's confident in his sexuality and lost a bet (either that or a rugby player). I mean, who hasn't gone out in public, dressed as a hula girl / cheerleader / French maid / Wonder Woman etc, at or time or another?

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  • Is this really a bet, or a fetish, if I may ask so?

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  • Were nothing, you can say its your new female clothes. folks don't approve to bad.

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  • Makeup, wig, semi girlie clothes. Dress a little punk. People will assume you're just a hipster.

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