Somethings not right. For starters you should be in a medium binding with a sz 9 boot and in the 3rd pic (iirc) there's about an inch, inch and a half gap between the back of your boot and the heel cup. I'd start by making the binding as small as possible and going from there.
ahhh....good eye. I wasn't really looking at the binding too much, just the boots. Size 9 boots should have no problem with his board, but the L bindings might be too large for his boots.