I wasn't successful with my first because he never latched but I plan to try nipple shields just something to look into
Your nipples cracked because the latch was bad. I had the same problem with my first. Once i got the latch down my nipples almost instantly healed. Find your local LLL or maybe your hospital has a BF support group. The best way to succeed is to find support and be determined. I went in telling myself of I couldn't BF my baby would starve and that helped my resolve to keep at it.
I'd say possibly a bad latch last time. Always ask advice. There should be someone who knows about breastfeeding you can talk to before you even leave hospital. Then they home check to make sure your still doing ok.
Thanks ladies! I have a lot to look into!
You should google tongue ties and lip ties so you know what to look for.
You might check to see if your oldest has a tongue tie, there are all types of variations from really severe to almost unnoticeable. My son had a mid range tongue tie plus a lip tie and it caused a really painful latch until we had it corrected. The reason I ask you to check your oldest is because it is genetic and if they have it then odds are new baby will too. It is something I will check right away when my second is born because I had 5 months of painful nursing with my first. I just didn't want to give up so I dealt with the pain.
You can also express some milk and rub it on your nipples. Let it air dry. Check with a lactation consultant to make sure baby has a good latch
Make sure you put nipple cream on straight after each feed so it can absorb fully into your skin. I also found if I was having a painful day passing a couple of warm flannels on my boobs would just help hydrate the skin and the warmth alleviated the pain. At the baby clinic where I got my son weighed they a la leche team who were great a checking your latch, giving advice to increase supply etc so depending on where you are it might be worth seeing what breastfeeding support groups are local to you.