How many times did you have sex til it started feeling good?

So I lost my virginity about a year and half ago, almost 2 years and haven’t had sex since. I’m damn near a virgin again. It wasn’t bad or anything but my relationship with the guy is a long story. Anyways, after that time I bled a lottttt, I bled that entire following week for some reason. I was hella embarrassed because I got it on his sheets but he wasn’t trippin off of it..thankfully. I really want to get back into it because reading all these stories.. mannnnnnn it’s tempting but all I can remember is how much it hurt and how much I bled. Basically my question is how many times til it starts feeling good/stops hurting? And do you usually only bleed the first time, if you even bleed at all? I know every girl is different but I’m an over thinker and I can’t help it lmaooo