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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."
loopholing by Lais May 31, 2006

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!'
Loopholing by Two Spoon Destroyer December 10, 2020

LoopHolsX 

Possibly the most gayest man alive. So gay in fact that he sucks hard dick every Thursday and rumor has it that hes a absolute semen demon.
WHY THE FUCK IS LOOPHOLSX SO GAY
LoopHolsX by CrexTheMan February 9, 2023

Gödel's Legal Loopholes

An extension and improvement of the original "Gödel's Loophole" (the logician's discovery of a potential contradiction in the U.S. Constitution that could legally enable dictatorship), expanded to explain similar phenomena globally. Gödel's Legal Loopholes theory identifies systemic vulnerabilities in legal and constitutional frameworks that, while appearing democratic on paper, contain hidden mechanisms that allow for authoritarian capture, democratic backsliding, and oligarchic control. The theory explains how formally democratic institutions can produce undemocratic outcomes—how constitutions designed to prevent tyranny can contain the seeds of their own subversion. It illuminates phenomena such as: democratic backsliding (gradual erosion of democratic norms), competitive authoritarianism (democratic institutions exist but are systematically unfair), Western authoritarianism (authoritarian practices in Western democracies), crony democracy (democracy captured by elites), oligarchical democracies (rule by the few within democratic forms), liberal oligarchies (oligarchic control masked by liberal institutions), democratic oligarchies (oligarchy operating through democratic procedures), Western oligarchies (oligarchic capture in Western states), and the Iron Law of Oligarchy (the tendency of organizations to devolve into oligarchic control). Gödel's Legal Loopholes are not bugs but features—structural openings where democratic forms become authoritarian substance.
"The constitution guarantees elections, but gerrymandering, voter suppression, and campaign finance mean those elections don't reflect the people's will. That's Gödel's Legal Loopholes: democratic forms producing authoritarian outcomes. The system isn't broken; it's working exactly as its loopholes allow. Gödel saw it in the Constitution; we see it everywhere—loopholes that turn democracy into oligarchy while keeping the democratic mask."