Tough one. You said you needed to initiate everything. He's awkward but seems to like it when you make a move while he cant himself. Depending on your and his age, which you havent disclosed yet, I think he's a virgin: he's scared and clueless.
So if you want to escalate, you need to do it yourself. Dont do it victorian style, be bold.
I lost my virginity with a very bold girl. She was touching me sexually after the second date and made no question about what her intentions were. If she wouldnt have been obvious nothing would have happened, I was such a chicken. I still have fond memories of her.
I hope you like virgins. Good luck.