Excellent question.This is one of lifes greatest turning points. The day the boy becomes the man, he is now equal to his elders in every way. Other than to get his own ride with two or more 18" subs in the trunk.
Serioisly to experience the greatest thing about being a guy is worth every year of the 14, 15, 16 or more for some that you have to wait. Well if your paying for it you have waited to long.
With that said I say hold out no matter what!! By all means don't cheapen this glorious moment by having to pay for it!!
Do as you will, but I hope all virgins would even just find a so-so looking chick once for free. I guarantee when you look back you will cringe with disgust. Fucking is fucking, there is no "i'm still a virgin cause I didn't love her" Once your p-p is wet there is no un-do button.