I was told breastfeeding shouldn’t hurt-- but it does! What am I doing wrong?
You aren’t doing anything wrong! You are trying to breastfeed and that is something to be proud of. It is true that breastfeeding your baby should not be painful. Some mothers feel tenderness during the first few seconds of baby latching, and it lessens during the feeding. This is common and usually goes away after the first week or two.
Some mothers may have cramping, tightening, or tingling in the breast when their milk lets down and starts to flow. This is also normal. Massaging the breast and using a warm compress while breastfeeding can lessen letdown pain. If breastfeeding is excruciatingly painful during the entire feeding, there are causes for this which can be easily fixed with some extra attention.
The most common cause for pain is when your baby is not latched on properly to the breast. Focus on getting your whole nipple and a lot of your areola (dark skin around nipple) into your baby's mouth. This will help the nipple to go back farther into your baby’s throat rather than rubbing on the roof of the mouth. Some babies have mouth issues that make it harder to latch on properly. This can be uncomfortable or painful for mom.
If your nipple is cracked, bleeding, bruised, flattened or creased after feeding your baby, it is time to pay closer attention to your baby’s latch. (Cool packs, nipple cream, or gently rubbing breast milk on your nipples are all soothing options.) If your nipple is white after breastfeeding or pumping this can be a sign that not enough blood flow has reached the nipple or can be a sign of thrush. Thrush is a yeast overgrowth on your nipple and can also be visible in your baby’s mouth. It is always helpful to have a Certified Lactation Consultant check your baby's latch. They can see if your baby has any mouth issues that affect breastfeeding, and make sure breastfeeding is comfortable for both you and your baby. If she suspects thrush or other problems, she can have you talk to your doctor about treatments that can help.
SOURCE: https://www.llli.org/breastfeeding-info/breastfeeding-sore-nipples/