Quote Originally Posted by @llli*sanyabee View Post
My question is: if I were to exclusively breastfeed him, even with the lipstick nipple going on (he does transfer a lot of milk!), do you think my nipples would just end up cracked and bloody?
Impossible to answer. Some moms get cracked, some never get beyond soreness. You can't really tell which type of mom you are without trying exclusive nursing and seeing what happens.

Or would they eventually toughen up?
Your nipples will never toughen up. They're not designed to. When a baby is properly latched on, the nipple sits on the back of the tongue underneath the soft palate, and it experiences almost no motion or suction. All the motion and suction is happening at the front of the mouth, on the relatively insensitive and elastic tissue of the areola.

Of course I'd like to get his latched fix, but it seems that might take a lot of time and patience and I'd love to get him nursing exclusively as soon as possible. I've heard a lot of women experience soreness when they first start breastfeeding, so maybe I just need to go through that before it feels better. What do you think?
Quite possible. I actually think you are addressing this in the right way- trying to breastfeed as much as possible, but giving yourself brief breaks when the soreness becomes intolerable. Just keep nursing as much as you can, and things should improve.

Do women successfully nurse with lipstick nipple?
Yes. I nursed on deeply cracked, lipstick-shaped nipples for 4.5 months, which is how long my baby took to grow out of her awful latch. (That was unusually long, BTW.)