He made a cute she. However, altering ones look is easy. What is hard is learning what a woman goes through in a day. I am no expert but I know that girls go through a lot, a boy would find it very surprising.
There's a link to the video, where we do his makeup But really the key is just to enhance the feminine features, without overdoing it: If you do that he'll look like a drag, its important to keep the makeup very natural.