I can’t have sex! Helppp (TMI)

So me and this guy have been trying to have sex.

I’m a virgin

He’s not

Every time he tries to go in it won’t go in and penetrate. He’ll get it in once but it kinda hurts so I make him stop. What should I do?

We always do role play too.

He has 3 bodies so it’s not like he’s inexperienced.

I think there something wrong with me.

We tried doing it numerous times same results on both days