Something weird is going on... My first time I was 20 something too and this never happened. I mean that first day yeah, but after that, not really. Of course, that first day we did it several times because he was a virgin too and was coming much too fast. Maybe that's what happened...
What I do know, however, is that it shouldn't be raw or bleeding that much. Unless you have a particularly hard Hymen, which can occur. Maybe you should see a doctor. If the hymen is hard and still there, that could be the issue. The hymen is a body tissue and does bleed. Some women need to have it surgically cut, ie. by a doctor because for whatever reason a penis won't cut it. (no pun intended)
Try using more lubricant. Condoms can dry you out sometimes too (even lubricated ones.) Try using a lot and see if that helps you. Sometimes natural just isnt enough and even though you say it you are relaxed, pain usually makes us tense. How long are you guys going for? I mean, if it's an hour you'll be drier by then. If it's ten minutes, not so much. Condoms tend to dry me out faster so I have to use extra lubricant. But I like long sessions. This may not be your problem.
I am also allergic to latex so I can't use those condoms, that could be an issue with you too. More and more women are becoming aware that they're allergic to latex. See if you get the same 'results' if you use a different type of condom. As far as lubes go, I find water based ones don't do anything for me, so I went for Silicon based. Much smoother. But you can't use it with silicone condoms. Check the label or ask the pharmacist (or store person) if you go that route.
Your vagina is made to stretch enough for a 6 lb baby so his penis can't be THAT huge. There is something else going on.