Haha! OMG - When I first started breastfeeding I totally could have written this post! Sorry, I haven't read previous peoples posts, so I don't know if this has been said before. Everybody always told me it shouldn't hurt, but it was absolutely excrutiating for me, and nobody could really tell me what I was doing wrong. Latch looked good, baby not tongue tied, etc. I eventually after weeks and weeks of pain, treated for thrush with topical creams which did nothing and finally diflucan. Around the time I took the diflucan, the pain went away. Was it thrush? Probably. Or maybe, just possibly, after nine of the most painful weeks of my life, my nipples finally got with the program and toughened up. At any rate, DS is now 18 months old and still breastfeeding, and painlessly I might add.
I guess my whole take on this. Perhaps your nipples shouldn't hurt, but is it realistic to expect them not to? My whole entire life, my breasts were firmly supported by a nice soft bra, protected from the sun, not chafing against my shirt, washed only with water or the mildest of soaps, and treated gently by my partner. Then along comes my almost 10 pound STARVING newborn boy who would do ANYTHING to get milk out of my pampered girls. And he did. He was a very aggressive little eater, and he ate often (every hour or two when he was brand new and then also when he was having a growth spurt). So my boobies went from being treated like royalty for my entire life, to being completely torn into. I guess I shouldn't have been surprised that my nipples hurt so badly, but they did. Like me panting on the edge of the couch with my fist stuck in my mouth to keep from screaming type of pain - you know what I am talking about. And I kept getting so angry at all the LC's, doctors, nurses, etc. who were telling me that it shouldn't! So many people I know had pain with breastfeeding in the beginning. I hurt for 9 weeks, my sister hurt for 6 weeks, my friend hurt for 8 weeks, another friend hurt for 4 weeks with her first then 2 with her second, you get the point. But just because a lot of people have horrible pain in the beginning doesn't mean that you don't have thrush. But, I would totally treat for thrush, just in case. I think that was a major contributor to my pain, and I let it go so long without being treated (even though my nipples looked totally fine). And if it isn't thrush, just keep gritting your teeth. I think some women have just more sensitive nipples than others and it does take time for your nipples to desensitize. After about 6 months of breastfeeding, I can safely say that my nipples were made of steel, and that almost nothing hurt them - not even when DS would have a mouthfull of bood and decide to look around the room.
So, treat for thrush and just hold on. And keep getting second opinions. You never know when somebody might pick up on something that you have missed. I know this pain seems like it will last forever. Trust me, I have been there. I know. But I promise if you can hold on long enough it won't. Good luck and keep us posted!