Unfortunately the only kind of push I would want to give you can be found on the infamous "got rope" thread with Deb.

As for the girl in question, if you have been agonizing about her for months, do her and you a favor and simply move along and leave her alone. From reading your self absorbed drivel over the last several months, it's my educated guess that nothing good can come from you actually booking a session with a girl you have been obsessing over for months. Fucking hookers is supposed to be "fun", not an obsession over someone in your real life. You mentioned "old feelings" in your OP. There are not supposed to be any feelings at all where it comes to your play dates, you've already crossed a dozen boundaries before even meeting this woman, how do you really think this is going to end?