Pain during breastfeeding above 3 out of 10, creases, cracks, or lipstick-like appearance on nipple most likely mean that your baby's latch is too shallow. There are some general tips to get you started with obtaining a deeper latch that you can find here.
For latch pain that doesn't improve after following those tips, I'm going to urge you to book a visit with a lactation consultant so she can assess your infant's latch and help with strategies to make it more comfortable. If you don't have lactation consultants in your area, try calling the national breastfeeding helpline.
In the meantime, what could you use to make your breasts more comfortable during and between feedings?
Between feedings, silver nursing cups are awesome for their ability to heal sore nipples while holding fabric off and letting them breathe. They don't require any additional products to work, just place them over the nipples inside the bra between feedings. I chose the particular silver cups in my nipple pain essentials kit because they also have rings that help the edges not put too much pressure/indent sensitive and swollen breasts.
Hydrogel pads are, as I mentioned in another post a three-in-one product. They heal sore nipples fast, hold fabric away from the breasts and catch milk leaks. Peel off the backing and use as instructed for 24 hours.
Try one method for 24 hrs and then switch to the other if your nipples are still tender.
For pain during feeding, you can also use a nipple shield. Nipple shields are tricky to use, and once you've met with your lactation consultant and chosen the right size and shape for your baby's mouth, here are my favorite 3 nipple shield tips:
Tip #1 - If your nipple shield has a cutout, it can be placed where your baby's nose will go OR it can be placed where the chin will go to help her get latched with a chin-led deep latch.
(In this pic, the cutout is at the bottom of the shield).
Tip #2 - Apply the nipple shield as if you are turning a sombrero almost inside out, lay it on the nipple and let it pull nipple and areola into it.
Tip #3 - To keep the shield from falling off, avoid the temptation of holding the shield by putting your fingers in a pinch hold around the nipple. Instead, try to avoid touching the shield and hold your breast behind the shield. Think about holding the breast and not the areola/shield area.
There are risks with shields and they are not a permanent solution to latch issues, and should be used under the guidance of a lactation consultant.