Kind of an awkward question (and a bit premature maybe) but here goes....

Recently started texting with this guy I met on POF. He seems promising enough, but I'm really worried about if we get to the point of having sex. I've only ever had one partner, and I recall my first time (which was with him, of course), hurt a lot. It was like forcing a jumbo jet into a too small hanger, and he couldn't penetrate the whole way in. Somehow we managed. The second time wasn't too much more pleasurable, as he still couldn't fit all the way inside of me, but he got further, and we managed again. I remember being so damn sore by that time that I declined to have it again for a few days to let myself rest. By the third time though, we managed full penetration and from there on we were good to go.

Long story short is, this all happened a few years ago and we broke up after dating for 6-7 months. I haven't had sex since then.

Since then I've met this new guy on an online dating site. He and I are probably going to have a first date soon, and I was wondering...if it leads to possibly more dates and eventually sex, will sex hurt me again? Does a vagina tighten up again after not having sex for several years? Or does it boil down to the size of this new guy being bigger or smaller than my ex?