So, basically, there's a lot of information out there in books, online, and in magazines. There are cosmetologists who are trained in this kind of thing that you can go to (Ulta does free evaluations and consultations in store) and they're a nice help for those who need it.
Ultimately, you need to at least know a little about color before going out and playing but, really, the only thing that will serve you well is *practice* and lots of it. Your first few attempts will take forever and generally look like hell but really look at other girls out in the world who are around your age range and see what they're wearing. I'd recommend that you try emulation before innovation (mimic current trends before trying stuff yourself) and take your face into account.
If you're on HRT, things will go a lot easier as estrogenized skin has a translucency that can't be emulated with any amount of cosmetics.
General tips:
- The moisturize/water thing? Yeah, that.
- LESS IS MORE
- Choose a tone that has complimentary coloration (you're red faced so choose the 'warm' powders/concealers/foundations.
- Be careful with eye shadows, generally they're a problem for a masculinized face due to the lower brow.
- No, seriously. Less is more.
- Day to day best friend combo: Eyeliner, mascara, translucent powder.
- The sooner you can start electro/laser, the better. Beard shadows and the indentations that the hairs leave are the #1 giveaway and also just can't be completely removed with cosmetics.
- Use blush only at night and even then only sparingly.
- Have fun with it at home but, again, less is more out in the world.
My final bit of advice is twofold: First, get a friend who you trust, knows your secret, and has good taste and have
her* look at you every time you can talk her into it. She'll call you down for looking silly and that's worth her weight in gold. Second, practice every day. HRT will change your face. Electro/Laser will change your face. You'll want the practice at getting in and out of makeup because speed is key if you want to have a life. Everyone here who wears the stuff went through an "OMG THIS TAKES FOREVER" phase but most girls can get their face on in about five minutes after practice.
*Sorry, gay boys are great for glam as a rule but generally like a bit more over the top looks than is likely to be what you're looking for.
P.S. - Regarding the facial hair: try to look past it until you can get it gone. You'll still want the practice but I remember that it can be very disheartening when all you see is the marks where the hair comes in. It'll go away in time and, provided that you keep your face healthy, your skin will look smooth and flawless with maintenance and care.
P.P.S. - In case you missed it earlier: Less = More