When does sex stop hurting?

Hi girls, I've had sex 6 times since losing my virginity and it still feels uncomfortable it's not really painful but it does hurt, we are doing the position missionary with him on top, roughly when should it start to feel good? We communicate and hes very respectful when it hurts and hates carrying on when I'm not enjoying it. I never finger myself so I think my vagina did a lot of stretching