I need advice from SHY guys. Please help!?

I've been dating this REALLY shy guy for 2 months. 5 alone dates plus other hanging out with mutual friends. he asked me out first but ever since then i've been doing 80% of the asking. He always comes to anything i invite him to provided that I initiate it. i'm fine putting in the effort to initiate dates and all that, but i'm not sure if i will ever have the courage to kiss him first. we have not had any physical contact at all. i know he really likes me. he pays for me 75% of the time when we go out and is always asking how i am and shows a lot of interest in me. my question is: will he ever be comfortable enough around me to kiss me? i have a lot of balls but i'm not sure if i'm ballsy enough to kiss him first. he's also a foot taller than me so that also makes it a lot harder for me. i can't just jump up you know? so shy guys, how can i make it obvious that i want a kiss?
I need advice from SHY guys. Please help!?
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