So, there's this guy who I don't know what do think about

I have a guy friend who confuses me too much and I don't know what to do with him. He's one of those lonely "I've never been truly in love" guys who like to be alone but really wants an S.O. He likes to exaggerate boobs but whenever somebody teases him with a girl, he gets very "meh", but when somebody messes with him with a guy, he gets super nervous and says "noooo, no". I also know that he once had a girlfriend, who once masturbated him and for what I know, he didn't enjoy it and was a little awkward. Ever since I came out to him, he's been asking me weird questions about sex, if I ever get some, what I do to masturbate, etc. I've been told that he's generally quiet and very shy and doesn't talk about sex much, but with me, he always talks to me about sex and looks at me with a face that I just don't know what to do about (which is something I've been told he doesn't do with ANYBODY ELSE).With a group of friends, we sometimes tease him about his sexuality because it's just too funny to do it to him, but he recently started getting too nervous.Back in 2014 I had a huge crush on a guy, and I remember my friend telling me "he'll never be with you, even if he was gay" almost every single day for like a month.I remember once we were with a group of friends outside and he asked me "are you still a virgin?", to which I replied that I'm not, and he then proceeded to stretch his arm and put it around my shoulder, and then took it out immediately right after I noticed. That day he also looked at me very closely and I was getting a bit uncomfortable.The other night, we were out also with a group of friends and he asked me if he could go sleep at my apartment because he couldn't go to his house for some reasons that I don't even understand, and he told me "I'd sleep with you in your bed, but don't touch me too much" WITH THAT FACE that is pretty much like the sexy face emoji. I got sort of uncomfortable and started thinking of excuses to tell him not to go to my house, and he went sleep with another friend.I generally feel comfortable with him, and I can see myself being with him but I promised myself thay I won't try anything with him unless he is comfortable enough to talk to me about his sexuality.What can I do, how do I talk him into opening and speaking out what he feels, because I can SEE that he is enclosing himself.I don't know if there's any detail I missed, but anything I'm willing to EDIT and update this if I missed any information.