It is often said that if breastfeeding hurts, you are doing it wrong. Do not let this common saying discourage you. In the beginning, breastfeeding is uncomfortable or painful for most women with each baby they have. But, there are ways to reduce the pain and make breastfeeding enjoyable for mother and baby. Proper Latch If your baby is not latching properly, this can lead to pain and sometimes sores or blisters on the nipple.