I see you've already gotten a bunch of great responses but thought I would add my 2 cents as well.
First of all, I absolutely second the recommendation to get some Lansinoh Lanolin nipple cream. That stuff works miracles.
I received the advice when I was pregnant with my first to work on 'prepping' my nipples before my DS was born. So from about 30 weeks I would rub them a little roughly with a wash cloth anytime I took a shower and put a bit of the Lanolin cream on afterwards or whenever they got dry. I don't know if this really helped or not, but when I started bf'ing I never once had pain or cracked/dry/bleeding nipples. I've started doing this prepping already now that I'm pregnant again.
Even though I didn't have any pain, I had a low supply, and really struggled for months to bf (which was really frustrating). It took 5 days for my milk to come in and then the first week seemed to go great, but for no discernible reason my supply dropped and my LO wasn't gaining or was losing weight every week. We tried almost everything (with help of La Leche League, Lactation consultants, midwife, doctor, etc) and couldn't get an increase, so eventually started combi-feeding when LO was about 4 weeks old. It took me about 9 weeks to feel like I was finally starting to 'get the hang of it'. Every day in the first two months was a struggle, and my goal was often just to make it to the end of the week... then the month... then till I went back to work (when LO was 12 weeks old)... then to 6 months... but I was never ready to stop.
We continued combi-feeding until LO was 8 months when my supply dwindled so it wasn't even sufficient for one feed per day. And it took a couple of weeks for me to come to terms with that as I didn't feel ready to stop.
With this new LO I would really love to be able to EBF and my goal is to make it to a year. Keeping my fingers crossed there are no supply issues this time!