The first time I had sex, I did not experience bleeding or pain, and haven't since. I have used a condom every time. Recently my boyfriend and I decided to lose the condom and go bare. Right afterwards there was pain and bleeding for a bit. Could it be that my hymen is just now tearing? And will it heal and tear again or heal torn, and never tear again?
Condoms generally have a very smooth surface, and they're slippery when wet, not to mention lubed, so sex with condoms doesn't involve much friction. That's one of the reasons it doesn't feel quite the same. If your hymen had been just politely getting out of the way before, it may have gotten torn this last time, but that's just a guess. Perhaps you can order your First Mate to go below and survey the damage before your next voyage. ;-)