Try putting on Lansinoh before AND after each feeding. It will help lubricate, rehydrate and protect the delicate skin from damage.
Be very diligent when you are latching him on that he is correctly positioned... go back to the basics of when he was a newborn: wait for the wide-open mouth, bring him to breast and not the breast to him, ensure that his chin in touching the breast, etc.
When you remove the nipple from his mouth, is it distorted, like pulled to one side, or pulled to a point on one edge? If so, that's a good indicator of a latch that needs correcting. Also, have you tried other nursing positions, i.e. side-lying instead of cradle hold, or football hold instead of side-lying?
