In my case my first real kiss (not counting spin the bottle and mucking around with friends and the like) came after a very long and uncomfortable hour or so sitting next to the girl on a wall with me attempting to make conversation about the weather and the like. I was shy, she was even shyer, but we both wanted it so, eventually, I sort of got up, she sort of got up, looking at me out of the corner of her eye (she's ever so cute sometimes) and then I sort of went in.

You won't explode or anything, but after all the that anticipation it was pretty good. You will probably think more than anything "God...this is so soft"...

Ahhh nostalgia... I really miss her sometimes still, it didn't work out for long because of the shyness, we're both better now but at first she didn't want to risk it for fear of me still being pathetic and undecisive and now I live 600km or so away from her.

Advice, if you decide to do something, always do it, confidence is the most important thing a man (or woman) can have, and fear of looking stupid or being rejected, well. It's nothing compared to a lifetime of regret. Trust me. You'll laugh about your rejections with your friends, but you'll suffer alone when you think about your missed oppurtunities for years after.

Sorry for the long post, good luck.