How do you know when a guy is ready to take things beyond cuddling?

This male friend and I have been spending a lot more time together than usual. He invited me to watch a film at his house after we went for a drink so I went and we had fun. We cuddled all night but when I tried to pull him in for a kiss he didn't really reciprocate. I don't think I was being obvious enough but I'm scared to try and then make things awkward between us after if he doesn't want the same thing. He's pretty shy and not very confident in himself but so am I. Do I make a move next time or do I wait for him?

How do you know when a guy is ready to take things beyond cuddling?
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