What's wrong? sex issues

So my boyfriend and I have been dating for 2 years now. We've not had sex yet partly cause we come from a orthodox background. Within our first 3 months of dating we hit third base. And we used to do this hot thing where I'd be giving him a handjob and he'd finger me at the same time while we make out. We didn't get a chance to go physical for over 6 months and Now, whenever he inserts his finger in me, it hurts. I don't get it. Also, he says that while we do stuff, I get wet only once in the beginning when we hit second base. Which probably explains why fingering hurts cause by the time he gets there, there's not much lube. Recently, I got my first oral and it was wonderful. But I felt my whole body getting numb after sometime. I don't understand. Is all this normal? This is my first time with a man and I really am quite clueless about all this. I really am not sure of what's going on I would really appreciate help

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