I am pretty sure that this is a caddy used by meter maids to empty parking meters. The coins in a parking meter are deposited into a container which only opens when it is placed into the square hole so the meter maids can't skim some change off the top.

Yea, these are actually called PeePee TeePees. The premise is that when you are changing your infant son's diaper. You place these TeePees on their member to keep them from peeing on you. I guess when cold air gets on their...area, it tends to make them pee.