I've put makeup on guys a couple of times, sometimes because I've had to, sometimes just because!
My school recently put on the play Cats, which is possibly the most insane musical the world has yet seen. Andrew Llloyd Weber had some mental issues, but I still adore the musical for all the memories it gave me. Besides guys in spandex (which was akward beyond belief, especially when we had to make sure they all had jock straps once!) I, along with some other girls, had to help them with their elaborate face makeup. Most guys fail miserably at putting makeup on, especially stage makeup, so I ended up doing a lot of it for some of the less fortunate. Like mascara and eye liner. It's difficult putting it on someone else, I was afraid I was going to gouge their eyes out! They also seem to not know how to take it off, because at school the next days, there would always be guys from the play wandering around with traces of eye makeup still on. Very funny!
And once, we had a surprise birthday party for my friend and as a surprise, we tackled him in his room, tied him to a chair with a jump rope, and put makeup on him. He looked nice! He was pretty willing too, so we didn't feel all that bad for surprising him. I have some great pictures!