Assuming the point is to embarrass him, there are two ways you can go.. you can make him look obscenely hot, like a prostitute with huge breasts, or you can make him look super cute, like a little girl with pink bows everywhere. Whatever you decide, get some super glue for the zipper so he can't back out without help.<br />
Hmm now that I check your profile I'm thinking this question is insincere. But I'll leave my answer anyways.
Shave all the hair from his body, even his pubic hair. Then pluck his eyebrows, shape them very femme. Make him wear fake nails and put makeup on him. For an extra touch, make him wear a bra and pair of panties. You might even want to make him wear pantyhose on his newly shaved legs.
Look in the mirror ducky and copy what you see. (Tsunami3 has your number)
dress him up as a women don't forget the thong and the nylons,Then get a ******* make him suck it like it was ur **** the bend him over and **** him with it
lol Be sure to post a pic
You may rue the day that you won the bet.
Hair falls. Make him a goth girl.
He might like it ! Be sure you're ready for the switch