This phrase is a reference from the Spongebob SquarePants episode "The Great Snail Race" where after fighting from Squidward and Spongebob happens for a while, the winner ends up being Patrick and his rock, "Rocky".
This term can be used when two people are focused on doing something before the other, and the person who ends up doing it wasn't in focus as the ones bringing attention.
(Someone knocks on door)
Tyler: I will get it first!
Sarah: I am faster!
(Tyler trips Sarah and bolts off. Only to find Jerry already opening the door)
Jerry: Oof. I guess the winner is Rocky
That time of night (historically past midnight) when the mind starts to stray, often resulting in much more suggestive messaging between two individuals. Said messages will often end with a "winky face".
I'm starting to feel a tingle, we must be approaching Real Winky Hours babe
Its what you have to do to train your girl to become a anal master, you gotta finger her with 2 in the pink and one in the stink and that one is the be the pinky.
Ana:Last night Darrel did the pinkywinky on me and I think I ready for his whole 2 inches!