He has confidence issues - he's afraid that being heavy handed and dominant will push you away from him. The track record of being friend-zoned by other women reinforces this, because every time he's rejected and dropped he has less reason to believe in himself, and therefore being more nervous with everyone he meets.

If you think he has potential to be a great long term partner, then tell that to him - but also make it your personal mission to train him into being a good sexual partner. It sounds like he really likes you, and all he's doing is avoiding situations that he's afraid of messing up (being on top, making arrangements himself, etc) and he's never going to learn if he doesn't have an opportunity to fail a few times in a safe environment. Train him to pleasure you and let him fail a few times. If he's talented, like an artist, or musician or something, then you can draw parallels between getting better at his work and getting better at sex. Once he can pleasure you he'll become more confident and that'll drill away the awkwardness around others and childish issues. But you will have to show some faith in him to begin with to avoid tanking his self-esteem by coming out and saying he's not good enough.... yet.

Anyway. That's what I'd ask for if I was in his position. No pun intended. Hope I helped.