All I will say is make sure it's well planned, you like the girl you're seeing and I wouldn't recommend making this a habit. Paying for sex once or maybe a couple of times is fine, but you don't want to be that guy who's payed for sex 50 or 60 times.

Enjoy the experience and then use it as a positive for getting a GF. You'll no longer have that subconscious " I'm a virgin " thing going on around women. Just don't expect the sex to be mindblowing, and don't expect it to do too much with your confidence around women. It'll help a little, but that's it.