Sex is so painful for me!

I love my bf with all my heart he’s truly been a blessing to my life. But sex is usually so painful! He’s an average sized guy and we’ve had a lot of sex so I’m not a virgin. It literally hurts to the point where I want to cry. Even when he’s gentle it still hurts. I’m also not “dry” when we have intercourse. Anyone know what could possibly be wrong? When I first started having sex with him I’d bleed afterwards. I don’t anymore but it’s still really painful.. :/