Brynden - It's all to do with the latching on. You need to try and get as MUCH of the nipple right in his mouth otherwise he'll just be chewing on the ends and that's really sore. Don't be scared to really push it in there, you will feel the difference when he is latched on properly. Try different positions. I always found lying down on my side really good.
This part is really tough, Are you feeling the 'let down reflex' when he's latched on?
Edited to add; lovely pics! what a cutie!