I never was able to pump either. It just didn't work for me. I tried everything, but just couldn't work.
I do know that if you start on the side that he has trouble with he is more likely to have a more forceful suck and cause that side to produce more if it really is not producing as much. That is what a lactation consultant told me at least. I'm sure you have a consultant in your area. Most you can call and see what you can do. I wouldn't worry if you can't pump (unless it is a necessity) because pumping might not be giving you an accurate "reading" of what you are producing.
-Amy
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