Huge underwear fetish here. I have over 200 jocks (havent counted in a couple years so it may be over 300 by now) And I stopped counting afree I reached 1000 prs of regular underwear. I think there are a few pics of my collection in my gallery.
I’d suggest he get a dr recommendation / Rx, and then submit for a FSA reimbursement from his FSA with a receipt for buying the jocks. Personally, I could see them being used for sports or a suspensory type jock after a medical proceduere. That said, if I could get my annual jockstrap spend...