I agree to be yourself, make up wouldn't really win a guys heart, its YOU that does. Make up makes you feel pretty, confident, and grown up.
Don't just go and directly ask him out, it might scare him away because your being too strong (if he likes you lots and your really sure, you could just ask him out, but if your nervous its best to take things a bit slower so u get used to talking, and spending time with him). You should get to know him, find out if he has similar interests, maybe an online game, or maybe a sport he likes, or going for walks.
If he likes playing soccer, for example, you could ask him if he would want to verse you 1 on 1 after school or something. Just talk to him and find out what he likes doing best, and ask to join in next time, that way, you will be less nervous and you will get to know him a lot more and you will over come that nervous feeling.
Hope I helped you fooet