So far as I can see, the jock-strap questions are a come-on and he's hitting on you. And the whole thing seems so narcissistic and shallow; he's not interested in you as a person at all, all he sees is an athletic body. He sounds like bad news and I would stay well away from him.

Much love,

Nobody living can ever stop me
As I go walking my freedom highway.
Nobody living can make me turn back:
This land was made for you and me.
(Woody Guthrie)