I'm 16 and my boyfriend knew i was masturbating and like 20 minutes later (It's a school night and 5am) he said it was worth it to stay up and i said "why" and he said "cuz i got you to cum i assume". I played it off saying maybe but i dont know, is it weird that i havent? I have always wanted to cum but i figured since i havent then maybe it was just a sex thing. i am a virgin too and so is he. i dont like to lie to him but i didnt want to say no.
Masturbating is what you do to figure out how to make it work, since you haven't, it appears you need to keep practicing. There is plenty of information about that on this site and elsewhere so get busy. Maybe he can help you if he knows anything but don't expect him to say he doesn't know even if he doesn't. Teenage boys are great pretenders and so are teenage girls as you know.