What is the most logical next event?

How to dress up a boy like a girl
Shave his legs, armpits, and face.
For a boy to dress like a girl, he needs to have no leg, facial, or armpit hair. Have him take a shower and shave his legs, armpits, and face.
If he doesn't want to do it himself, have him sit on a chair while you gently shave him. Spread shaving cream onto his legs, dip a razor in a bucket of water, and then save the hair off of his legs.