I don't have much time, so I'll just touch on the sex thing.
Because it appears that sex is his LL, and just the fact that he is a male, sexual contact with you is most likely essential before discussing things that focus on "feelings". I know that this is a real conflict for you as a woman (we typically come from another direction) and having a different LL all together. Can you find someway to initiate "touch" with him? To let him know what a great lover he is? This may require you to push yourself and act from outside your comfort zone.
Sometimes, depending on the person and the moment, asking the "feeling" questions are best asked soon after he has been sexually involved with you and feeling relaxed and more connected to you. You may want to experiment with this as to how soon after, as to how long the window will be open, and what kind of questions he will be comfortable with. Remember to ask your questions with you DB cap on, and of course, thank him for his answers, even if one or two of them aren't exactly what you wanted to hear.
