With my first baby I remember going to my Ob and complaining that my boobs were sore. He (being such a sympathetic male!) said it will be worse once I am feeding and that I need to toughen them up now! He suggested rolling the nipples and trying to express some of the colostrum out. Did that and it still hurt for the first couple of days. A tip: find a good nipple cream - you're going to need it! Lansinoh was given to me in hospital and it was great.
And as for early leakage, apparently you get more the more kids youhave. I have been getting some leaking since about 20 weeks, and now I find that I can get quite a bit - probably not enough for an icecube though!
So toughen those boobies ladies. My DH seems to enjoy "helping"!