Pain during? Too tight?

It might be tmi, but does everyone else experience is really tight and experience pain everytime they have sex? Like really intense pain every time. Even if I'm really aroused, and we use lots of lube or my boyfriend goes down onme (sorry haha). I'm not a virgin, i'm 20, but I'm mostly concerned because it happens every time. It's not just that i'm more tight during my period, it's all the time. It takes a huge amount of time to " get it in" and for the pain to go away. And it's a bit always sore after.

Anyway, anyone else experience this or have advice about that?