Kaz, try the ABA helpline 1800 mum 2 mum.

This is probably not going to make you feel much better, but the only thing that really worked for us when DD was two and giving me the same troubles, was time. I think it was just a mismatch between size/position/teeth/whatever that we grew out of.

Pawpaw ointment helped my nipple heal. She was only bfing twice a day at this point and you might laugh, but those advanced healing bandaids in between and overnight also sped up the process. Kinda weird to strap them on, but definitely helpful (also stopped the wound scraping on bras/clothing).

He will get through this and so will you, it's just not very nice in the meantime!