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1.
when a man ejaculates on the tip of his penis then shaves his pubic hair and sticks in the the jizz on the head of his penis thus looking like a wig for the head of his penis!
i can give you a head wig for 10 dollars
by cove11 November 16, 2010
 
2.
Another word for, condom.
I won't have sex with you until you put a headwig on.
by Moose Tracks April 22, 2009