You win

Whilst it would feel so nice to have Bobs cock up your ass, you want to experience his tight hole first. Quickly fisting your cock, you feel your balls start to churn just seconds before the inevitable happens. Your cock sprays cum like a fountain as you let out a puff of air.

A minute after you finish, Bob grunts as he cums. You turn to him smiling and say "Alright Bob, I think I'm gonna make you wear..."