When I first had ds, I was also under the impression that "if it hurts, you're not doing it right" - not sure where that came from. As ds was prem and in SCBU for 3 weeks, we didn't have an ideal start, so was pretty much prepared for it not to be easy. Once he was allowed to try to latch on around 5 days after birth, I realised pretty quickly that his tiny little mouth would make it difficult as he kept slipping off and ended up right on the nipple, but fortunately, I had been shown how to detach and try again. I think it was because of the non-standard situation that I was prepared for some negative feeding experiences, so I was able to persevere through difficulties. (he self-weaned at 18mths).
A week or so out of hospital, bf was going ok, but was still a bit sore (no-one had advised Lansinoh - was unbelievably brilliant second time round). Due to being on AB's ds got thrush in his mouth and latching on felt like needles going through my nipples - I used to sing at the top of my voice with the pain. I pointed out the white spots on his tongue to my HV, and mentioned the abnormal pain, asking if it could be thrush, and she said "I'm not sure, might not be, you need to check with the GP" [hmm} - at the time I put it down to her being too cautious and scared of misdiagnosing. Obviously it was thrush, and the treatment worked within a couple of days. A bit worrying that she didn't have the skills to confidently diagnose it though. I felt that if I hadn't mentioned thrush, she would have just suggested that the latch was poor. I'm sure others have plenty of stories about how HV's are unconfident when giving bf advice.
Breastfeeding is like embarking upon a new exercise regime - your body is doing something it's not used to, sometimes it feels weird because you've not used your body in that way before, but that's ok, it's normal. Sometimes you might feel a little sore at first as your getting used to it, but as you go on, it should get easier and easier and more rewarding. Some people just don't get to that 'rewarding' stage with their exercise regime - they neither enjoy nor really hate it - they feel it's just something they need to do. The same could be said of breastfeeding. It's always best to get a good trainer to advise you and show you how to do your exercises in the best way - same with breastfeeding. If you get pains while exercising, you seek advice, find out why, if there's anything you can change. Sometimes, it might be best if you stop...I won't go on, I think you get the drift.