Don't be embarassed to read this. Whether you've never kissed someone at all or it's just been too long since you've been with someone or even if you're with somebody now, you can really benefit from the tips I'm going to offer you. You might notice I have not made this hub gender-specific as actually most signals for kissing are universal-- with a few exceptions of course.
The only truly important context for kissing is whether or not this person likes you, as in likes you likes you. The moment before the kiss you don't have to be incredibly funny, serious, charming, or romantic. In fact, hold off on being romantic if this is going to be the first kiss you are to share with this person. In can create a lot of awkward pressure that too often foils chances to kiss or be kissed.
In fact, awkward pressure is inevitable for most kisses (assuming the kissers are NOT lecherous, intoxicated, or have not kissed before). The trick is to channel the right signals through the awkward pressure of the moment. Many advise to maintain eye contact, but I say this is very unsubstantial. The most powerful signal to send is to look at the person's eyes and then the lips and towards the entire facial expression. A little smile or smirk after this well show the person you're thinking about kissing them. You have a chance to interpret whether or not they're open to kissing you based on whether they keep they body language "open" or even mimic what you do. By this time, one of three things will happen. First, should they initiate some kind of subtle touch like touching your elbow lightly or stroke your hair-- you're golden. Obviously, if they go for an embrace they REALLY want you to kiss them. But perhaps say the person doesn't have an obvious reaction. They just stand there doing nothing and their feelings are indiscernable. Initiate a touch like one previously mentioned. If the person doesn't pull back and doesn't "retaliate" you can go for the kiss. If they do, you know quite well this person doesn't want to kiss you! Nonetheless, it is substantially less embarassing to get shut out of touching an elbow or hair than it is for someone to literally duck from you or push against you. Finally, if the person has turned away, crossed their arms, or otherwise "closed" their body language it is quite easy to say this person doesn't want to kiss you.
Don't worry too greatly about how to posture your lips. You only need to pucker a little if at all. Don't sweat over dipping your head to the left or to the right. Just don't get dizzy! If anything, going to far the left or right may strike the person as really weird. Two people who like eachother and are kissing don't have a problem with how long a kiss is. If one is taking too long, the other might just pull away. Don't take this the wrong way-- take it as a tease. Let it be funny, let it be sweet, and just let it go. Be wary of the tongue kiss. It is truly one of the weirdest and most wonderful ones out there. Save it for another time when you get to kiss more-- or if you're kissing a lot already on this first time... hell, why not? If it doesn't work, let it go. Rememeber you have to give in order to receive and vice versa. You or the other person may find yourself shifting your boundaries outward. This means you're sharing a very good kiss. From thereon, I will not say anything further. Will you have sex? Maybe you can, maybe can't. Should you have sex? Maybe you should, maybe you shouldn't. Judge your individual situation correctly. Know yourself and know the person you're kissing.
This is what many people have the greatest difficulty. You're ready, and perhaps they're ready, but the atmosphere is not right. Typically, it's easiest to share a kiss in a dark or dimly lit i.e. private place. Kissing is an intimate moment that few people like having voyeurs around. That said, there are some darkly or dimly lit places that DO NOT work. They are actually two of the most stereotypical places to get a kiss. First, the movie theater seldom works out as it is a public place. People come and go as they like and they won't ignore you if you're sitting near or in front of them. It's pricey and uncomfortable as the seats are segmented off from eachother and you might even have to juggle a whole tub of popcorn. If you really started to go off, you don't have adequate space to make out so freely. The second place not to kiss is at the front door. Though it seems appropriate to start or end the date with a kiss at times, you're likely dealing with someone who is coming and going from a place other people also call home. If they live alone it does work fine. But if there are family members or roomates around, they can easily snoop around to see you, even if it may be difficult to see outside into the dark.
What places do work? The most comfortable place to kiss is at home on or near a couch or bed. However, be careful about busting a move near a bed. Your kissing partner may take it as a seriously sexually aggressive move and may be turned off--- or turned on :D. Generally gauge how comfortable they feel in your bedroom when it's just the two of you there, door shut. If in doubt, start with the couch if you can. If the bedroom is the only private place you have access to, start standing up or even from lying on the floor. The next best place to kiss is actually a park. Indeed, a park is also a public place, but it's also much easier to foster some kind of anonymity there. There are many parks that are scarcely used and most parks have some place where you can hide away from the public eye. Guys, just "going for a walk" happens to work really well. Just choose to arrive at a destination where you know you can spend some time alone.
I hope you feel much more confident about your future kissing endeavors. That really is what it comes to: confidence. If you can carry on without feeling totally embarassed, you're doing just fine.
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