How do I say it?

I've never been one to find myself confused about relationships.
Honestly.

Or even hesitant, for that matter, which is a fairly unusual quirk for me; I'm a fairly hesitant person. On the chart of spiral dynamics, I tend to hang out in the "green" stage (kudos to any random reader who knows what that is.) In most situations, I am nearly has hesitant as Hamlet, without all the angst. But with relationships I tend to throw all caution to the wind and say "What the hell?" Why not? Who knows what psychological yarn balls of entangled delight and intrigue I will find? (Odd analogy, I know. Run with it). I've had some pretty damn good relationships because of it, Z in particular, and some really really really shitty ones.

It makes life interesting, to say the least.

But now I find myself attracted to a friend, and I know he's attracted to me as well, but there is a lot of hesitation there, on both sides. A big reason is due to professional reasons; He is an employee for a company I work for, and while for me this is just a passing job, for him this is his career. And the company has specific rules about inter-company relations, which we are breaking, thus risking his career.
But I'm quitting my job. This is my last week. I decided to quit because my school was falling behind, and my anxiety was raising, severely. But as soon as I've worked my last shift, anything he and I do will be perfectly kosher. It hit me a few days ago: Once I'm done, where does that leave us?

He's an amazing guy with awesome geeky interests. He's still in love with his ex. Ouch, nothing much I can do about that. I prefer someone who is more dominant. But what is cute is that he is actually putting effort into being more dominant. He'll spank and hit and bite and restrain me, knowing I like it. He prefers women who are a little more physically aggressive. And I find myself being a little more aggressive then my usual shy self when I'm around him.

And yet, when I try to talk about what I've been dying to talk about, I get shyer then I have ever found myself. What are we? Why are we hesitating? Does he want anything more, like a relationship, or would he prefer to leave things as is. What would his idea of a relationship entail, anyways? I am just a side trip on his journey to find The One?
Usually I have no problem with communicating like this, but for some reason I am facing difficulty. I really like this guy, and would love to pursue things further, but I don't want to pressure him into anything he is reluctant to go into. I just want him to be happy.

He seems happy enough when we're together. He's very physical, which makes me happy because I am a physical person as well. He's not afraid to cuddle or curl up while we watch movies. He'll kiss me at random times. We laugh and joke a lot.
Why do I hesitate?
We've only been doing this for about two months. I really don't want to fuck up this friendship by pushing for something he may not want.
I wanted to talk about it last time when I visited him last night, but we both fell asleep before I had much of a chance. I'm trying to attack this from a Buddhist standpoint, and just enjoy the moment, regardless of the uncertainty. But it's hard, humans don't like being uncertain.