How to put makeup on a sleeping boy without him knowing?

Try to keep him up for as long as possible so he'll be very tired and likely end up in a deep sleep. Make sure to apply the makeup very softly and carefully, just a little bit at a time. One of the hardest things to do is to keep from giggling while you're making him pretty. Use liquid eyeliner so you don't have to press down hard. It can also be funny to paint his fingernails or to glue on fake fingernails while he's sleeping - you can do this easily without waking him up and it is really hard to take off! If all else fails, just try typing him up while he's sleeping, that way it won't matter if he wakes up because he won't be able to do anything about it anyway.