Sometimes, the pain just does go, as the baby grows, but I would explain that as a result of the baby being able to open wider and get more breast in!
This seemed to be the case for me with DD. Feeding her was painful in the 1-2 weeks and Iwas told she had a small mouth. Pain went away magically, without any changing of position or anything. I guess her mouth got bigger. Even when it was painful, I had good breast drainage and she was satisfied from the feeds, so I knew it wasnt' a latch problem. We are still going strong at nearly 16 months!
I failed miserably to BF my DS, now 3yrs. He wouldn't latch on whatever we did, and I god poor advice from the HVs and midwifes. They scared me into giving him formula as he was close to dropping 10% of his birth weight. But I started to express, soon got rid of the formula and went on to give him just breastmilk till I went back to work at 10 months (ofcourse with food after 6 months!).
I was totally unprepared for anythign going wrong with breastfeeding and that it could not come naturally to both of us. I attended an NCT class, but the intructor never went over any breastfeeding problems that might arise, never said to get help if it's painful or what to do if we have problems with latching on etc. Only just told us the benefits of BF, which everybody already knew anyway.
Out of 6 of us in the NCT group, all of us when on to breastfeed till 6 months though (I ofcourse was feeding expressed milk). But bang on 6 months, 3 of them stopped, I carried on till 10 months, 2 other girls till 1yr. Pretty good going I think.
When I took DD for her jabs at about 4 months, the nurser asked me if I was BFing. I said yes, and she asked totally? Said yes and she said "wow lucky baby!".