hannah Montana, Milly Cires, one of the Olsen twines and if you think of more tell me and tell me how to do it The Ole Classic Man As A Woman Costume - Ideas?::
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Have him become one of the Village People or Boy George
it's impossible...sorry. ;)
shave ALL body hair lol.....get a wig and some make-up....let your girl friends do your make-up and dress you....smile and have fun :) New NWT Carters Girl Boy Halloween Mummy Onesie Top 3 - eBay (item ::
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a wig and dress, and make-up
AMY WINEHOUSE its easy and everyone will know it.
Bee hive wig, thick eyelashes, heavy eyeliner and a black t shirt with jeans. press on nails and cigarettes
Wear a dress, some pearls, lipstick, eye shadow, blush, a blonde wig (that basically works for any of your ideas), a bow in your hair, heels or at least sparkly flats...speak in a high pitched voice. Stockings or tights will hide any leg hair you may have...paint your nails pink (and buy some nail polish remover for the next day...or that could be a little awkward!).
That's just for a general "girl" costume. If you want to be more specific ie Hannah Montana just take a microphone along and wear similar clothes to her. Or you could go as Amy Winehouse...the possibilities are endless, there.
Get a wig at Clarie's cause they sell them there. See if one of your friends that is a girl has clothes that will fit you. And have them put make-up on you.
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How do you turn a boy in to a girl for halloween? 
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