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Let It Be Known
Simple rule: If you want him to kiss you, let him know. If you're shy, let your body language, coquettish smile and playful touches do the talking for you. The more obvious the better, though, so even if you are shy, take a chance and just literally tell him you want him to kiss you. Why be embarrassed? You'll relax your partner and give him the confidence to treat you to his best moves, bettering your chances of having a weak-at-the-knees, all-in-a-tizzy, oh-my-I-have-the-vapors first kiss.
Ignore the Stigma
There is no reason why a woman should feel like she can't or shouldn't be the one to lean in the first time. Don't be afraid to take your date by surprise if you think that the moment is right. It's very memorable and sexy to be the daring girl who confidently initiates romance and doesn't let (a kind of boring) tradition dictate the first kiss.
Give Him the Opportunity
If you are dead-set on having him be the one to start the necking, make sure you give him the opportunity to gracefully make the switch from casual to intimate. Keep the conversation going, but don't talk a mile a minute and keep it breezy. Nobody feels comfortable making a move when you're in the middle of telling him about how many baby otters are literally covered in nuclear waste right at this very second or how despicably the nation fat-shamed Kim Kardashian just because she gained some pregnancy weight.
It's Not That Serious
Bottom line: Kissing is supposed to be fun. Yes, it can be powerful, erotic and exciting, but all of it is supposed to be fun. Don't clam up or get angry when your perfect first kiss gets bungled because he accidently kissed your teeth. If you want him to go for it a second time, help salvage the moment by laughing it off and pulling him close again. Show him that despite any awkwardness, you still have a good attitude!
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