Everyone is different. But I don't touch until the woman touches me first, then you can touch her. I know some guys have success by touching first, but I'm really not interested in making something happen with any particular woman... if she isn't interested, I move on. It's so much easier with gals that are open to you.
As far as kissing them the first time.... I just know. I think you just get this from experience and it's really hard to explain when a women is open to you kissing her. It's her body language, facial expressions, what she says, it's a combination of things where you just get this message from her, "Kiss me already!" The only advice I can give you is that women are VERY intuitive. If you want to kiss her, and you are thinking about it, she will know and if she is open to it, you should be able to pick up on it. BE WARNED, if you want to kiss her, and you don't she will KNOW IT and you will be weak in her eyes. So go ahead and try, if she's not open she'll turn her head and you will know where you stand.