As I'm only a trainee BF counsellor I'll help as much as I can but I'm not supposed to give advice (as I'm not insured until I'm qualified) and am only a quarter way through my course. So anything I say is based on my own experience and is not advice - this is my disclaimer!
Cyee - sounds like you might have an inverted nipple? It doesn't always have to be a problem as baby shoudl take a big mouthful of breast, not just the nipple, and should draw your nipple out with the suction. It's amazing how wide they need to open their mouths. There are people who would say try and use a nipple shield and swear by it (you can buy them at boots) - and others who say you should never use a nipple shield as the baby will become addicted to it and may reduce your milk supply. A breast pump can also help draw your nipple out - or you can if it just doesn't work out successfully feed from one breast only.
Here's what babycentre say
Caroline 1852 - completely agree, I strugggled for 6 weeks before cracking it, feeling guilty every day for not managing properly to do the one thing that I thought I could do for DS. Wasn't bothered about my c-section at all but did care about BF (don't know why, just the way my weird hormones were working at the time). I had loads of help and support too - it just took me forever to get it - and get the thrush seen to.
I learnt something useful (well I thought it was useful!) this week - the best indicator of how much milk your bub is getting is number of wet/pooey nappies. You should get 5+ a day. Can be as many as 10 or more (aargh!). So buy yourself some nice soap and handcream as your hands will be sooo dry from non-stop washing.
Please do ask me questions if you like - you're helping me to learn stuff!