So the pain can only be helped if you have a lot of foreplay to help get her ready. Honestly even after that, you simply may just be too thick for her specific body shape.
If you're hurting her, she isn't going to have an orgasm. Not everyone's brain is wired to be able to feel pleasure in pain. And honestly, as a woman who can't take super thick girth, it literally feels like a burning tearing sensation when there's too much stretch and I'm not ready. It's incredibly uncomfortable and not at all fun.
What is "everything" that you do? Specifically what do you do to get her ready for you?