Bf’s penis pain + 4 hours of trying

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My bf (19 m ) and i ( 19 f ) have been debating asking this question on here. We tried googling these things… we are just drawing a blank though. About a month ago we tried having sex. My bf is the first person I’ve (attempted?) to be with intimately. It is not his first. We did foreplay, and it was all good. But we attempted to have sex for 4 hours straight. Switching positions, doing things to stay horny. For some reason, it just wouldn’t go in. I’m not sure if this is the appropriate place on reddit to ask. But i have two questions
1. His penis has been hurting for a month straight after this- do we go to medical help/ has anyone experienced this before?
2. In future preparation to try again (once his penis feels well) is there any tips/ other people who have experienced similar problems when trying to do it the first time?

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