Whats the border between being funny and crossing the line?

Yes it was quite clear that his intentions were to get you into bed. Guys in general see every girl who is nice to them or "playing" with them as a potential mate, and that alone is already crossing the line from their side, but this doesn't mean you should stop being nice to guys or not play with them. Just stay clear of touching them too much even in a playful manner, that gets their hopes up. A hand shake or 1 or 2 hugs a day would be more than enough. I hope this helps ;)

Well, hate to break it to you, but guys are horny. Yes, he is trying to push the limit and sees how far can he gets.

I would guess that while he may want you sexually, the reason for his joke was that he thought it was funny.

The border between funny and line crossing is when one person involved feels uncomfortable. Then the line is crossed and the "humor" needs to stop.

This guy though, I would think that he does want you. The first joke could have been written off, but the second one seals it. He wants you, and I'd bet that he doesn't just want you sexually, I bet that he would love the chance to spend any time alone with him. It could have been a ploy to get you to leave and spend some serious time in discussion with him. but, ya. He digs you.

Um yes this guy sounds like a creep and you did the right thing by saying no way. I suggest making sure that you're not EVER left alone with him because you may find yourself in a helpless situation, and you definitely don't want that. He also sounds cocky and doesn't sound like the type that would take rejection very well, so I'd be EXTRA careful. Good luck hun.