I don't think he's thinking of cuddling as "friendship territory." Guys most often do not cuddle unless they are sexually attracted, or want a relationship. That's the problem with young relationships. Neither party knows how to act. It's like a blind person feeling around in the dark. If you ask him indirectly, there could be a misunderstanding. It's hard enough as it is to communicate with guys, because most of them think differently than we do. So if you ask him, ask directly. Don't send mixed messages either. He is likely just as confused and lost as you are.