I'm confused - is this a fetish or a kink or do u want her to help u do it as a tutorial for when ur ready to go out into public? Either way u have to find someone u consider close that u can be open with. Tell them u don't want them to freak out but ud like them to apply makeup to urself for whatever the reason is.
You have a girl best friend? If so, ask her if she would put make up on you. if you're uncomfortable about it, just say you're going to a costume party as a woman and need makeup, so she'll help you either way. But honesty is the best policy.
It won't Exactly look right until you get the hang of on which make up goes with your skin and just your features in general. It's going to take time and experimenting. They can show you some things as far as techniques and you can do the rest.
Get together with a girl ffriend for a basic hangout. Try starting a fun conversation about looks. And then say you wanna find out how you will look like if you had all that makeup on. Ask her to put it on you.
You don't. You're male. Women can give you tentative approval at best, but you will always still be male.