Thanks both of you, I always thought he had an excellent latch, nice wide mouth, lips turned out, wiggly ears and temples and big big gulps, but it's just this mis-shapen nipple that worries me.
I use a pillow Dee, the only thing I really struggle with is taking him to the breast so to speak, because he is soooo bloody heavy I generally have to get him into the right position and then pop the nipple into his mouth, obviously I don't get to be hands free then because I have to support him where he is and the breast with the other hand to keep everything in the same place!
I've got some gel now for Thrush and I'm gonna try that, maybe it is Thrush that just isn't presenting itself externally yet that is causing the soreness, it doesn't seem likely, since I have visible cracks on the nipple I'm pretty sure it's down to that, I just don't seem to be able to fix his latch properly...