The last two months have been absolute
I examined Lily's latch. I admit we were getting lazy with making sure she was in the proper nursing position because for so many months (months 3-10) we could nurse how we wanted and it never hurt. The only times I would experience pain with breastfeeding was when I would pump and startle my body into making too much milk. Ouch engorgement! Needless to say, I was back to being paranoid about our latch. I tried would compress my breast and hold it in place for her and that seemed to help. I wouldn't do it every time though. I should have, because it seemed to help me. I also would apply lanolin and/or some antibiotic ointment to the sores to try to get them to heal.
Finally, after two months of suffering in silence (well, my husband knew, but no one else) I decided to ask my favorite La Leche Leader for some advice. She reminded me about using a correct latch, gave me ideas on how to make sure that happened and suggested new, more toddler-friendly nursing positions. I am happy to report that her advice is working really well and was just the nudge I needed in the right direction. After two months, one side is now completely healed and the other is nearly there. Today I nursed my baby without cringing, and without dreading the nursing session. I actually enjoyed the experience and fell in love with breastfeeding and with my baby just one more time.