I grew up in West L.A. and a bunch of my friends ended up working behind the cameras in Hollywood, so I learned a few tricks here and there (these are from a buddy of mine who moonlights doing makeup for drag queens and drag kings):
1) You can use makeup to add a little five o'clock shadow to your upper lip and chin;
2) You can use contouring makeup on your forehead to emphasize the orbital bones around the eyes and make it look like you have masculine brow bosses;
3) Try to lessen the arch in your eyebrows when in guy mode. Men's eyebrows tend to go straight across and sit lower above the eyes, and they may even be a little higher on the inside than on the outside;
3) Get your accessories right. If you are in an environment where it works (like rave type nightclubs) wear fingerless gloves to make your hands look bigger. Wear a large men's wristwatch, and a dogtag style necklace. And wear a baseball cap to cover your hair. Get one with a logo for a heavy equipment company for authenticity. Wear one earring, rather than two, and make sure it looks masculine. Observe guys who wear an earring to see what they wear.
4) As far as the boobies, you don't have to bind them if it is not comfortable. Find a sports bra that flattens them some and holds them really still, and then wear layers over it -- a loose T shirt with thick fabric, and a Pendleton or button down shirt over that. Lots of guys have moobs, so if they show a little it isn't "game over."
5) Wear Doc Martens or some other kind of shoe that makes your feet look bigger. Guys always have big feet.
