i think in this situation it would be extremely appropriate to ask him directly each of those questions, and not tip toe around what you are really trying to ask. After all, it seems he has not taken care to be any kind of subtle or vague- I really feel you need to be direct.

I don't know the situation in which you found yourself engaging in these conversations [how you know him initially], but for me discussions of sexuality and sexual behavior fall into two very discrete categories: intellectual/academic and personal/private.

intellectual/academic discussions are ones in which people might present personal experiences, but not in a way to invite others into those experiences, to apply pressure, or to make any kind of personal connection. it is for the sake of discussion, knowledge, debate, etc. Because of this, I might feel more comfortable engaging in such conversation with people i don't know as well- but certainly not one-on-one with someone I am not comfortable with. It would be in a group discussion atmosphere with the purpose of knowledge and discovery.

Personal/private- that would be where one shares experiences and personal beliefs or comfort levels with another, usually on-on-one, in an effort to learn more about the other person, have them know more about them, or to attempt to engage them in some kind of more familiar relationship [sexual, romantic, platonic, any given combination].

It isn't clear to me what the exact nature of hisintention is, as it is unclear to you. But it does seem to make you uncomfortable, and he appears to not pick up on that- which would be a red flag to me, personally.

If you ask the above questions in a direct manner, you will likely then be able to conclude whether you can feel safe around him or not.

if you already feel "unsafe", I would heed that intuitive warning and proceed with caution- its likely more about his behavior and how he is treating you and approaching you rather than the actual content of your discussions [as you seem to be willing to have an open mind].