My piece of advice.
Btw can I just say I absolutely loveee topics like this! I get so hooked for updates! :P
My friend went out with a friend who she was reallyyy close with but we always knew he was a bit of a player, but didn't work out at all and they broke up within 2 weeks, and they've never been the same before. But that was due to other reasons too e.g. religion etc
In your situation though, you guys both seem totally hooked on each other! He really seems to like you and believe me a guy will always answer 'what do you want me to think of you as..?' when they like you. Otherwise they'd just say your such a great friendd, great personality blahh the usual. When a guy does that, there's a lot more on his mind you don't know about. ;) unless he's a player and is kinda flirty with all girls.
I completely understand your situation about not wanting to ruin youir friendship but do you wanna have that regret in your life that 'what if..' feeling? That would totally eat me up from the inside! True it could leave you worse than you originally started off with and maybe even to the extent of not being friends no more but if it's true friendship, just like love it'll come back after a while. ;) We all fight but when it's true friendship, we always get round the situation eventually.
So my advice to you is seriously just got for it, like don't throw yourself on him. But just drop hints that you're cool with all this and a lil flirting does no harm. ;) and it is bound to get the message across.
His previous experience shouldn't stop him because not everyone is the same and more than saying it again and again, you should prove it to him. :)
I agree about the stubborn bit though, if I was in your situation, i'd be exactly like that, very stubborn and refuse to make the first move! :P
But just saying the fact that he kissed you, you enjoyed it and made out with him in return too clearly shows you both have feelings for each other and let's face it, it's gonna be playing at the back of your minds for some time as to who likes who. So i'd just say go for it. I know..easier said than done but good luck and let us in on the updates!
Best of luck hun! :)