If you see a guy that's having some second thoughts about kissing you then by all means go ahead and do it. He will be glad and you will show that its ok to kiss you when ever he wants. As for the first time. Well you have to make sure that this guy knows how to deal with girls. If he's a shy guy that barely had a girlfriend in high school then no you probably shouldn't kiss him on the first hang out If he's had 3 or 4 girlfriends then go for it.
If you want to make it 100% obvious then get that glitter in your eye and look at him like your completely enthralled with him. Look at him like he's the greatest guy on the planet. Otherwise just tell him "Kiss me"
You won't know until you jump out of the plane, I would not mind if the girl initiated the first kiss, but as far as kissing a girl the first time we hung out hell yeah that's something I would do
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