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Anyhoo, we continue chatting I kiss her some more but she has to hang out with her out of town friend tonight and I need to get back home as I needed a lift. She drops me back to the original jazz bar where I'm getting picked up from but my friends take 20min to get there in which time A full makeout session ensues and I get some boob action however we were in a parking lot and she didn't want to be 'trashy' I turned her on as much as I could but she was hesitant on me touching the vajayjay.
As a guideline, if I can't realistically be banging the girl that same night, I don't try for it. It might get the girl excited, but when she leaves you thats the kinda thing that alot of girls are going to feel trashy or bad about afterwards and it will leave your date on a bad note. If you left on just a makeout, and you are the one who ended it (when possible always be the person that ends it, so that it seems you are in control) then you leave her wanting more. In your situation, a good move would have been to, towards the end of the make out, grab her inner thigh firmly with a nice large grip, and give it a squeeze. Do this while looking in her eyes and tell her that stop this cause she's driving you crazy. It sounds dumb to most guys but that grab is going to get her wet and wanting more. I can't fully expain it, it's just a good move. It doesn't make her feel like shes done anything dirty, but it makes her nether regions feel good.
If you had the whole night with her and bringing her home was a real possibility, then by all means, push the limits. Get her comfortable. But if you don't, I advise against it. You want her thinking "oh that's that guy that turned me on so much" not "that's the guy that fingered me in the parking lot. If I meet up with him he might bring that up and it's hard to talk about."