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Right after Sam was born we did just fine. Then my milk came in. My breasts were rock hard and painfully full, and he just couldn't get latched on. I was lucky - I knew that it would get easier quickly, so I maintained a sense of humor about the whole thing. That said, it was painful and I was not happy about my inability to feed my baby.
I tried expressing milk in the shower. I tried applying heat, ice, whatever I could think of. I had help from my midwife. I had advice from the pediatrician.
I joked that the learning curve was that leaf you try to hit when you're a kid walking down the street, smacking every branch over your head; that one leaf that you miss, and you break your stride to turn around and jump a little higher to get it, but all you succeed in doing is breaking your stride because the branch is too high. So there Sam and I were, trying to nurse and just too short to manage it.
We used a nipple shield for a few days on the fuller, more sore side, and on both sides at night. Sam learned to draw enough of the nipple into his mouth. I became less full and my nipples eventually stopped being so raw and sore. And then it clicked and we suddenly are like old pros.