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 2, 2009
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A classy way to say you were cheating on your wife or husband.
Adulteror: Yes, I am guilty of a Marital transgression but I would like the public to know I reget it.

Average person: :| you mean you cheated on your wife.
by problemo_official February 1, 2011
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When a female has a tatoo on the lower back, almost like a target. Also known as a tramp stamp.
That dancer has a nice transgression stamp, I believe it is says "Tiger".
by MikeyMikey7 December 11, 2009
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The practice of doing a second wrong deed after being caught doing a first wrong deed, with the hope that you'll probably just be punished once.
Larry: Oh man! The Double Transgression Theory! It's like when a dog is sent outside because he pee'd on the rug, so knowing he's already in trouble he takes a hotdog off the table on his way out. Brilliant.
by Craigers McCraigers August 16, 2008
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a sexual encounter with someone whose politics you vehemently oppose, but whose body you can't get enough of.
Sarah, an anti-war hippie, was ashamed of her poli-sexual transgression with Lieutenant Adam Smith last night, but damn if his army six pack didn't make her want to make love, not war!
by champalace March 9, 2009
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Having a fear of the water sports so paralyzing that you turn gay.
Why didn’t Tremmel go whitewater rafting this year?
“Oh last time he went he end up with Transgressive Homo-Aquatic Terror. Now he just spends all his time trolling for dick at rest stops on the interstate.”
by Sarsaparilla Titty Fuck June 9, 2022
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