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loopholing

The act of drastically exploiting a not-explicitly-forbidden part of a generally well-worded contract; grossly violating the spirit of the law but not the letter. Also, the act of having anal sex and still calling yourself a virgin.
Dick Cheney did some serious loopholing with that whole "it's ok to torture enemy combattants because they're neither soldiers nor civillians" thing.

"I know i'm trying to be celibate, but no one said anything about handjobs...i guess i did a lot of loopholing this weekend."

"I hear Catholic girls do some major loopholing."
by Lais May 31, 2006
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Loopholing

1. (Adjective) Consistently returning to the same destructive behaviour as before with no reason dor doing so.

2. (Verb) For a male, ejaculating inside a woman without using a condom but not getting her pregnant therefore finding a loophole in the biological cycle. Hence loopholing.
Caity: 'I'm really worried about Chris, he's loopholing again and I don't know what do!'

Joe: 'Just tell him to use a condom!'

Caity: 'It's not that.....He's shitting in the sink again!'
by Two Spoon Destroyer December 10, 2020
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Related Words

Loopoling

two naked people do extreme acrobatics while preforming oral sex on the floor with cameras watching every move.
Lindsay Lohan..... ;) Loopoling
by MagicManOfMagicPersonalities September 20, 2013
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loopholish

The act of containing multi-loopholes.
Internet Explorer is so loopholish.
by Joe December 28, 2004
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