I lost my virginity quite young (16), so I can't fully relate to being an older guy who hasn't gotten tail. Trying to put myself into the situation, if I had gone many years of wanting pussy but unable to get any, there would be a lingering feeling every waking moment. I'd pay for it just to prove to myself that I am capable of physically having sex and perhaps even able to please a woman. That would probably help get rid of some of the 'approach anxiety' or the fear of not performing well in the bedroom. Because you are slightly older than the average virgin, I can imagine 'closing the deal' would be filled with a lot of nervousness and apprehension, which the girl will pick up on.
I have a good friend who is in a similar position to you, i don't think there is anything wrong with paying for your first time, which I have told him, as long as it is not made a habit. You won't get any less pussy for doing it, no one will find out, and at that stage I'd say it can only help.
Once you are getting with your 4th or 5th chick, I highly doubt you will look in the mirror and see a failure who "had to pay for his first time". In 5 years time you will barely remember your first time and it will just be one of the 1000 times you've had sex.
I have a good friend who is in a similar position to you, i don't think there is anything wrong with paying for your first time, which I have told him, as long as it is not made a habit. You won't get any less pussy for doing it, no one will find out, and at that stage I'd say it can only help.
Once you are getting with your 4th or 5th chick, I highly doubt you will look in the mirror and see a failure who "had to pay for his first time". In 5 years time you will barely remember your first time and it will just be one of the 1000 times you've had sex.