He bleeds and is in pain.

Hello, my boyfriend and I️ have been dating for about 5 months now. We recently started doing the dirty.I’m top and he’s bottom. My penis is not the biggest by any stretch of the imagination but it isn’t small either. During our sessions in bed he bleeds when I️ insert and thrusts. I️ can tell he is pain and I️ offer to stop but he wants to keep going. This has happened the last three times. He is new to this “in the ass” thing.Is this normal, will it go away? What should I️ do?