My nipples were flat fionas and i did find the first few seconds of a feed would be sore, as she sucked my nipple out longer. I could really feel the ligaments stretching in there! After a few days i used to stretch them out by hand myself before i attached her, really pulling them out long (slowly so it didn't hurt!) then popping her on quick. It was still a little sore and they are now (after 7 months BFing) less flat than they were before BFing, but still pretty flat. Another thing i found helpful is to express off the beginning of a feed if i was very full (first thing in the morning whn she was sleeping longer for instance) as when the breast is very full and firm it's even harder for the nipple to stretch out, and the pump worked dual-action to stretch the nipple out and soften the breast a bit by taking some milk out. I think the main thing is to know that as the baby gets bigger it DOES get easier - the wider they can open their mouths the easier it is for them to get a good mouthful, no matter how flat one's nipples are. There is also a device (nipplette?) one can buy which goes on the nipple and works by suction to draw it out. Some women use them in pregnancy to help stretch their nipples a bit. Worth a look maybe?
I'm in the same boat really - had to wean sooner than i wanted, building a wall of knowledge as defence against the same problems next time.
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