Pain during sex

Okay so I’ve had sex like 4 times (all with the same person) and it still really hurts when he first slips inside of me. We do lots of foreplay and I get really wet but it still hurts and he said that I’m really tight. What do y’all suggest to reduce pain? After a while, I loosen up and it feels more pleasurable but it takes a while. Also, I can’t for the life of me seem to orgasm during sex. I’ve tried clitoral stimulation and all the different positions and it’s not working.