Pain During Sex

I’ve been sleeping with the same guy for the last year and half and I have always felt some sort of pain when we have sex. Eventually it’s normally when he sticks it in and the pain will go away eventually. I can also tell that he has trouble going inside of me and to be honest, he’s not even that large. Why is this happening? I don’t want to speak to a doctor because it’s not that serious, but I realized that I always bleed a little when we always have sex. It gets annoying because I feel like it’s hindering me from completely enjoying it. Is it because I’m not completely turned on? When I get fingered, I don’t bleed and it’s completely fine. But now at this rate it’s gotten out of control.