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1.
Somebody who rides the penis much like a cowboy rides his horse
Wow... look at tim cook... such a penis cowboy.
by TheFridgeMaster November 30, 2009
 
2.
Occurs when one man spreads barbecue sauce (preferably Bull's Eye) on another man's scrotum. The man who spread the sauce then proceeds to lasso the scrotum to the point where the blood stops flowing to the penis, thus forming a tip resembling that of a cowboy's hat.
Hey Johnny, you should really watch out for the penis cowboy. I've heard of some weird things going on at that place.
by JayJayDesaree January 23, 2007