Top Definition
The act when one person (male) inserts their penis into a second parties (male or females) anus during which the second party makes flatulent's into the wiener hole of the first party thus creating a balloon animal effect called "Whistling Dicksy". While this practice may seem harmless it has taken many lives.
Dan was whistling dicksy all night, and now the room smells like a sweaty penis fart.

If you are whisltling dicksy tonight I need you to take a shit right now, cause nobody likes a shit filled wiener hole.

Jim tried Whistling dicksy last night but there was so much compression in his penis hole that he died.
by Omega Sigma Tau March 22, 2013

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