In reply to olddirtydoggy:
Masai are good in cracks and so are lace shoes. If it hurts that much it likely means you are inserting the toe and twisting which is poor technique and forces the knuckles of the toes against the wall of the crack, causing pain.
Instead, insert the foot sideways and then simply drop your heel down. Your foot/toe will jam in the crack without uncomfortably pressing the knuckles against the wall of the crack. Once it jams, straighten your knee to add stability to the jam and load it.
This is all described in Pete's excellent book on crack technique which you can find here.