I can relate a lot to what you're going through. I'm 25 now and even still I get really nervous in a situation where I want to kiss a girl, but I do it anyway. I can tell you that its been the right choice every time because if a girl didn't want you to kiss her, she wouldnt put herself in those situations. Even if it ends up awkward, so what. If you're surrounding yourself with nice girls they might at least feel flattered. Hang in there, my first kiss wasn't til I was about 17 and the girl practically did all the work for me, but don't wait around for that. Next time don't hesitate and do it anyway.
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