Would he be open to wearing a device 24/7? There is a sheaf-type device that acts like a foreskin called a senslip http://www.viafin-atlas.com/senslip

It works to dekeratinize the head of the penis that happens with circumcision, to lessen the rubbing on clothes and underware, and resensitize the head. Kind of like the change your hands would undergo if you were a gardener/carpenter/hands on laborer who never wore gloves and had dry and heavily calloused hands to suddenly going to wearing gloves all the time. The dry skin would moisten and the callouses would lessen over time and your hands would become softer, smoother and more sensitive.

something to think about...