I cant have sex because it hurts me and him?

Im 16 years old, hes 18 years old. he wasn't a virgin, i was up until a few days ago. We tried to have sex a few days ago, but we had to stop. i understand the reason it hurt me was because i was virgin, and being broken is pain full. however we find it so difficult to have sex, im very tight and he has a very sensitive downstairs area, and often has trouble 'pulling back'. Is there any easier way for us to enjoy sex without having to stop, because we're both in pain. We've tried this 4 times or something now, its still as tight for us both.
 
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