Love with caution. Remember that it is not in your power to change him, nor is it right to try. All you can do is control yourself.

I have to advise you against the booze part, because it means that you are already breaking the law, and then your friend in under the influence of a mind altering substance when you are interacting with him. And that's just not good. If it really is the only better choice vs. boozing and drugging with other friends well, then, that would be the first point in this discussion that I have not envied the choices you have to make: rock vs. hard place is never easy.

On the sex part, I think I have something more to offer though. He has to know... no, you can't read his mind nor control it... you have to know that he knows where he wants to take your friendship. And if he is, as you say, unsure then suggest that you "just stay here, at this point, just cuddling and lving each other physically without sex, until you know what you want. That way you won't regret anything we do together like you regret being sexual with some of those girls. I don't want that to happen to us, I care to much about you."

That would bring you two to roughly where my bf and I were for most of our relationship. We took it a bit further, but not "all the way" or whatever. But we knew what we both wanted, and were content to wait on more.

Just always remember to hold him in your heart like you would a bird in your hand: if you hold too tight, you will crush it.

~CSL