pain when going deep?

sometimes when i have sex with my boyfriend and he goes in super deep i feel pretty uncomfortable and it even hurts. it’s a weird feeling, like my insides are just being moved around painfully. when he’s just going in normally it feels good and everything’s fine! i usually feel the pain when he goes deep in missionary or doggy. i don’t know why this happens to me, i’d love to know if this is normal/something others have experienced or what i can do to ease the pain?? i’ve also never had an orgasm from him :(