Can you help readjust his lips after he is latched on? Have you tried the football hold? Also, try squeezing your breast like a sandwich to help him get a better latch. You want him to have a wide mouth and it sounds like his lips being in might preventing that. Also put milk on yourself after nursing and let that dry first before using lanolin. That will help with pain too. Really does sound like his latch needs some adjustment. Try La Leche League if you can. They might even send someone to your house if they have someone available. Hang in there, it will get much easier!