Unable to have sex

So on Saturday and Sunday my boyfriend and I were trying to have sex. Whenever he tried going in me, it would hurt and he wouldn't be able to slide all the way in. Then he tried eating me out. It felt nice but I was unable to orgasm. But when I masturbated, I was able to orgasm. We have no idea what's going on. I'm not a virgin and we have sex frequently and lubrication isn't the problem.