From a strictly sexual standpoint, almost any "losing my virginity" experience has the theme of not knowing what you were doing or even how to go about doing it. So, if you remember feeling that way yourself, then why in the world you would think that a plus when it comes to a sex partner? Sex is like anything, the more you do it, the better you are at it.
And hell no on the paying for it.
I've known people to who the whole "she gave her virginity to me" thing seemed like a very important part of their relationship, but I don't really get that either. To those who seemed to still consider it a big deal years later, there always seemed like some darker undercurrent of control or possessiveness or something there that just made me cringe a little. Certainly nothing wrong with a couple being each others first, or one of them being the first, but I don't think it is any predictor of future relationship health or stability.