Most Helpful Guy
In the past I've been given 'blatant signals' and they'd go right over my head from my nerves or apprehension from the things ingrained into me from child birth. I was raised to be reserved, pure, not out-of-line, abstinent but not religiously. I literally feared expressing sexuality. It was hard, really hard for me to break through the feeling that what I was doing was wrong. He probably gets this feeling. It took reassuring, someone saying the words that it's okay to act the way he's never felt. I know it kills the romance mindset having to sit down and talk/explain things but it clears the air for both of you; rather than hinting and never going forward.
I'd want to have sex, I wanted to be passionate, but I was just... held back by myself. It was who I was, not every guy is the same, nor every girl. In fact I'm going through this with a girl in a similar way, and it's difficult looking at it from the perspective of having some experience.
It may seem difficult to you, wrong, or negative that he can't push to where you want. But he's just that way. If he's with you and you're with him and you and him care about each other; nothing should be allowed to ruin that.
Forgoing the sit-down approach. You could have each other together(like how you took off your shirt) and ask for his hand and press it over your bare body. To literally show him it's okay, like "see? it's okay." Think of it like teaching someone to dance, you show where the feet and hands go. He's new, doesn't know what to do, what to think, there's nothing wrong with that.
This is all from what you've told us, he might not be exactly like this, but it's good to have the perspective. Good luck to the both of you.