How do you put make-up on a boy?

you don't, it's just that simple. If you're trying to dress him as a girl, you just work on him like he's a girl. If he's got facial hair, you need to get rid of it first--shaving, waxing, whatever--but other than that, just pretend he's a girl. If this is for stagework or television, he needs foundation, a little bit of contour on his cheekbones, powder all over his face, and a lipstick maybe a shade darker than his natural lip color--Maybelline makes a Nude Blush shade that's great for this. If it's a big theatre, he'll need eyeliner too. Do a makeup test; make him up, put him on stage with the lights set as they'll be for the show, sit in the 10th row and look at him close. If he's got good facial features and you can see his eyes and mouth, you're fine; if his face looks like a beige blob and his eyes disappear, he needs more makeup. If he's just going out in public as a guy with makeup on...he better know how to fight, because someone will start one with him.