Should I go ahead and kiss him?

Don't stress over this! Everyone makes a big deal over the first kiss moment and they try to make the whole thing as magical as possible - kissing in the rain or something - but the magic comes with kissing the right person. Don't force it, like Savage said, and if you two just have this feeling that's felt in the gut and the time is right, just kiss him! As for how - your first kiss will be absolutely terrible. It's not like the movies, believe me. You two will be awkward about it but don't fret, the follow-up kiss is the best one! I'm happy for you and hopefully you'll let us know how it went!

It'll happen when it happens. Don't try to rush it, but don't ignore the urge if you feel like doing it. If suddenly the moment seems right and you want to kiss him, go for it. There really is no "how" you just sort of find your own style and learn your own way to do things. Everyone is different, *shrugs* As per "where" you do it, I suggest you stick to his face as kissing his armpit or shin might be a little strange.

My first kiss was a boy I didn't know running up to me and kissing me, then spitting Gatorade all over me as a prank. That should tell you a little about how much first kisses can stink. They're nothing to stress about, and when you think the time is right, I say you go for it! Do what feels natural, and it will fall into place. Good luck!