My first thought was to make sure you both don't have thrush. I experienced cracked, bleeding nipples when my second baby was only 3 weeks old and on top of all that we had thrush. It was extremely painful and there were many times I wanted to quit. I would cry and swear silently when I nursed I was in so much pain. Using Lansinoh and taking baths and walking around with no shirt helped a lot to aid the healing and then obviously using thrush medicine, which you can get over the counter. We made it through that though and we are going on 7 months. I know it's hard but I also found it helpful to try and limit nursing to about 10 minutes, just so my breast was getting emptied or at least partly but still allowing it some healing time. Fortunately for me my baby tends to eat quickly so it didn't seem to be too much of problem. hang in there. I thought my nipples would never heal, but they did.