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When a multi-millionaire celebrity pro-sportsman who can all but walk on water, has the world at his feet, has the most stunning Scandinavian swimsuit model wife that not even the teenage serial-masturbators from "Weird Science" could begin to create, and has dream product endorsement deals shooting out of his wazoo, decides to play "hide-the-cocktail-wiener" with a dumb blonde nightclub waitress, thereby jepordizing his unbelievable good fortune for the sake of a "3-pumps-and-a-squirt" hook-up. The man forgoes Grade-A steak to feast upon a Wendy's patty...
Tiger Woods: "My darling wife, please forgive my transgressions, I have let you down..."

Mrs. Hot Woods: "Hmm... I know, why don't I repeatedly forgive your transgressions with this nine-iron in your face you cheating burger-girl fucker??!!"
by QuinnyT December 03, 2009
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Sep 6 Word of the Day
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Damn that was a steezy ass kickflip son!
by niggaliciouszor April 29, 2007
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The act of comitting a vile act or transgressing against another person.

A wrong doing unto another.

Hurting another for no appearent reason.
Walking upto someone in the street and giving them the finger or slandering their name.
by Alex Pipe May 19, 2004
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1. (social) breaking any rules or boundaries

2. (art) creative endeavors that break as many rules as the artist sees fit to break.

Transgressive artists have sometimes disagreed with their being called "artists", as the term has become quite overinflated, cliched, and pretentious.

Detractors of "transgressives" have leveled the same charges at them.

My personal opinion added:
Transgression is not enough, but it's a real fuckin' good place to start. It should be done any way you want it, but I like mine with a side of fun.
1. Kyle grabbed his crotch and looked her up and down as an act of transgression, as if to say, "Fuck you, bitch."

2. Kyle videotaped this escapade as a work of transgression, as if to say "Fuck art and fuck you" via his art movie.
by VyleKyle August 23, 2008
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A group of whores who like to ride one-quarter Chinese, one-quarter Thai, one-quarter African American, one-eighth Native American, and one-eighth Dutch married dick.

These whores generally hang out in Las Vegas and will travel with said dick to exotic places in the world for a ride; Australia etc. Sometimes these whores appear on shitty reality tv shows; ie Tool Academy.

This word is usually used by Stanford graduates and other well spoken people to confuse the semi-retarded general population.
Sorry for my transgressions, but I had a rough day on the golf course and my model wife's vag isn't good enough.
by December 04, 2009
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When a celebrity, while traveling, gets all sorts of road sex with many many different partners, behind their spouse's back. Almost always leading to being caught by their spouse, and forcing them to make vague, cheesy apologies to the media.
Golfer Tiger Woods said today that he regrets "transgressions" that "let his family down."
by MRpolite December 02, 2009
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