Kaz, i think i had something similar to you. When DS was around 8/9 months, he seemed to aggrivated a part of the nipple, which over weeks developed in to what i can only describe as hole! it was about 1cm x 1cm rounded, and i would cry while feeding it hurt so much. I tried various healing creams and eventually went to the ABA clinic. They had actually never seen a wound so bad they took photos of it for research purposes. At that age he was still a frequent feeder, at least 8-12 feeds, comfort sucker too. Weaning wasn't an option because i'd tried to wean him at an earlier stage and it was too stressful for both of us, plus i really wanted to make it to 2 years.
What they told me was that the repeated "trauma" to the wound was making it not heal, as in every time he fed it would re-open. They suggested placing a type of medical tape over the wound to protect it while i fed (i can't remember what it was called, but it was water proof, like a band aid but safe for him to have mouth contact with). I didn't use this all the time because he didn't like it and would pull off and re-attach which killed! They checked my attachment and all that was fine... we could only guess that his mouth alignment was slightly out and he was a powerful sucker. I only used the tape when the hole bled, but apart from that, this will sound strange but i would try to meditate while feeding to cope with the pain. Just using visualisations and gritting my teeth.
I fed like this for 4 months!!!
Then strangely enough, we went on holiday, just a very relaxing beachside retreat. And within those 2 weeks the hole suddenly healed! The only thing we can make of it is that my own exhaustion and stress was delaying healing, the rest did me wonders, and that maybe his mouth/bite finally grew and he no longer put as much pressure on the area. It was definately a relief, and i'm proud i stuck through it because i continued to BF him until 2 years & 8 months old.
Oh, and the other thing i would do was after each feed, smear lots of breastmilk on the hole...healing properties there too
I'm not saying you should suffer through this, just that it can be done, and that i don't believe this will be a permanent issue for you! If you just think of it as temporary maybe that will get you through?
I was reading the other day about some tips for babies who's top teeth are causing damage. Apparently a few mums have had success with tilting the baby's head back so that the teeth can't touch the breast. Another way to do this is to hold your baby near the top of his back, and pull his body away from you. Feeding while lying down can help also.
It was also suggested that washing the breast after a feed helps the wound to heal so that the baby's saliva doesn't continue to irritate it after a feed.
I just came back to this thread to re-read the suggestions because my nipples haven't healed yet
We're down to one feed a day in the early morning. It still hurts a bit but usually is not as bad as it was before - I think that's because I've had some sleep (often not much!) and so has he so we're both relatively relaxed. He won't let me change his position at all without protesting, pulling my nipple, pulling off and crying etc etc.
Healing bandaids haven't worked but I'm going to try paw paw ointment and breastmilk as I forgot those ones before.
Just thought I'd re-post in this very old thread to celebrate that FINALLY, breastfeeding has stopped hurting
It has only been in the last few days, so it took about 4 months My nipples are not quite healed but definitely nearly there and it is such a relief to just feed again without pain. I think they have healed in time for DS to wean but that's ok. If he weans now it will be his choice, not mine for short term selfish reasons (my feelings about weaning due to my pain, not comment on what others might do in a similar situation).
I thought I would come back and re-post so anyone else coming along and reading this later would know how it ended and possibly be encouraged that although it might take a while, your nipples will heal again.
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My nipples are not quite healed but definitely nearly there and it is such a relief to just feed again without pain. I think they have healed in time for DS to wean 
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