Here's my advice to you. I've posted it elsewhere. Pretend you are in a play. Really like psyche yourself up about it. I know it's crappy to lie but in this case it will make it easier for everyone. Then go to a department store and pay for someone to do your makeup. Tell them that you want them to do it lightly but that you will do it darker for stage.
Do not buy cheap make up. It is a waste of money and it reads horribly. So if you go to a counter in a mall you can just print out a character that you are supposed to play. One of the easiest plays you can say you are doing is "Hair Spray" And just get them to help.
I personally do not agree with most of the make up jobs that I see on this site. I am a cisgender woman and part of what looks very "clocking" in the pix I see are tons of makeup when cisgender women hardly ever wear make up.
To start what you really need is your eyebrows professionally done. You can do that easily in a salon. You can use the Hair Spray excuse again. Take a picture one of the characters if you need to back yourself up.
Next. You should invest in good quality lipstick and you can get away with cheaper mascara for a while. Do not use eye liner. It is very dated looking. If you want eyeliner only apply it to the outer corners of your eyes. Do not ring the entire eye.
Next you should try to figure out how to put makeup on your face by the kind of SKIN you have. If you have oily skin it is different from dry skin. I have very dry skin so I don't tend to break out. I rarely wear foundation. If you have good skin, dry skin then Visuelle by Loreal is the foundation I have used for years. It's application is nearly flawless. It stays on very well and applies well. Do not use sponges to apply foundation. Put the foundation on your face by dotting it on. Then use the sponge to wipe it around. If you use the sponge you waste it. It gets sucked right into the sponge.
Tip: the color of your foundation should match the inside of your wrist. Do not attempt to match it to your face. You will be wrong. It will be too dark when you actually use it.
arg! I found up my foundation was discontinued. That ought to tell you how much I wear. Damn this was good make up.
http://www.makeupalley.com/product/showreview.asp/ItemId=43686/Visuelle_Liquid_Makeup_]_[DISCONTINUED]/LOreal/Liquid
If you have oily skin, one cheap and easy tip I've used over the years is to put Dove moisturizing DEODORANT on your face before you apply foundation. It sets it on your skin and prevents your face from sweating it off. When I used to go to clubs I'd put it on this way and dance the whole night and it would still be perfect when I left. Don't be gross. Keep a separate tube just for your face. ONLY use Dove, the others are too strong and will damage your skin.
I would really advise you to buy make up at a make up counter. Usually you can get a really cool gift if you spend about $50. So you buy the foundation and get free lipstick and mascara. This is awesome.
In my experience boys tend to have longer eyelashes than girls. This is because boys tend to be hairier. So you might be lucky. If not there are mascaras that lengthen the lashes. Check out mascaras here.
http://beauty.about.com/od/mascara/tp/best_mascaras.htmYou will need to reapply foundation or undereye circle coverage AFTER you put on mascara. Tiny flecks of it drop down on your under eye area. it will give you a "raccoon look" that is not too attractive. Also hemmorhoid cream can be used under the eyes to tighten the skin there. Yes I mean like Preparation H. It's very very cheap and works like a charm. Models have used it forever.
Lipsticks you ought to try a color. If you have nice teeth and pretty smile go for bold. So for example if you have big lips and perfect straight white teeth you can wear any shade you like. If you don't stay away from bold reds and look for more pale coral shades.
Your age is vital. If you are younger you can get away with anything so play around.