I'm a senior high school student and as of lately I've started to talk to a lot of girls I had been afraid to talk to previously. Anyways, the thing is I've only had a few hookups and those weren't because of excellent gaming, just luck really. I find myself able to easily get girls to like me but I still have no idea where to go from there. I find myself unable to escalate with girls like this. Can someone explain to me how to escalate physically from here?
My verbal escalation and talking are fine just physically I am a little inexperienced.

Another problem I've run into that I could use some help with is one of my friends girlfriends. Background:

This girl used to like me but I passed on her because I was unsure and told my friend to go for it. At the time me and this friend were really good friends but he's become an asshole to me and my other friends. Anyways, me and her hung out one day and she told me about how she didn't want to be with him anymore and I let her tell me all this junk for a little while.
Later that day I told her she needed to find someone she could relate with and was attracted to. She then asked if i wanted to hook up with her (probably just make out, bj at most) and i told her I can't until she breaks up with him. However, he didn't answer his phone at that point so when I wasn't around she gave him a second chance.

Anyways, now that this guy is really being an ass hat I want to get with his girlfriend to get back at him. Firstly, do you think that this is alright?
The second question is how can i "suggest" and persuade her to break up with him? I have an idea as to how to do it but input would be appreciated.

Thanks

PS. Please focus more on the physical escalation question as I have a couple girls that like me and I just don't know how to reach that k-close point.

You need to work on kino. Google "pua kino" and read the articles and watch the videos.

An excellent place to start is with Gambler's "Stealth Attraction" video series: http://www.youtube.com/playlist?list=PL3D0D9763FDD24035

Let us know how this works for you... ~50

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--== I'm just learning this stuff too, so take everything I say with a grain of salt and follow your intuition ==--