- They don’t tell you how bad it hurts. From the moment your little one latches on for the first time until around the second month it will hurt. I’m not saying it should be completely unbearable but it will hurt. It takes your nipples a little while to “toughen up”. My first baby was tongue-tied and had a horrible painful latch at first (before surgery) but my second had a great latch (yes, it was still painful at first). Nipple cream and refrigerated pads will be your best friends! Engorgement also hurts. I discovered engorgement when my little ones started sleeping all night. One early morning I woke up to engorgement. I pumped around 10 ounces and still had enough left to breastfeed, seriously I was that “backed up”! If you don’t have good posture while breastfeeding then your back may hurt. This momma recommends the side lying position, trust me!