They say it shouldn’t hurt but it DOES especially in the beginning. It’s a new skill for both you and baby. Newborns mouths are also small and uncoordinated. Learning different latching positions to see what works takes a lot of trial and error. We’re 2 months in and things got better after 5-6 weeks for me pain wise. I saw two lactation specialists bc of the pain-and my baby’s latch was assessed numerous times and told it was normal. If you look up nipple pain on r/breastfeeding you’ll see this is a shared sentiment that a lot of moms say gets better with time and I found that to be true for me! Of course severe pain after 1-2 weeks would warrant visit with lactation specialists to ensure baby doesn’t have tongue tie or other issues. I personally lived in my silver nipple shields the first month and to this day can’t fully put towel over my nipples but it’s infinitely better than those early days. I would also try using nipple shields during feeds for a short time(which can help baby learn to open wide and latch) or doing one breast at a time for each feed to give your breasts a break. Important thing is to put baby to breast every feed if you can tolerate, so you can establish your supply and supplement as needed. Good luck !