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Just ask him! A lot of boys would be willing participants.

If you're not willing to come right out and offer to dress him up, try proposing a bet where you'll do something embarassing if you lose, and he has to dress up as a girl if he loses. If he takes the bet he's probably hoping to lose. Even if he wins, if he took a bet once, he'll take one again. Eventually you'll have him in a pretty dress and lipstick.

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3y ago

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