Abysshole 

It’s beyond the word “asshole”. For the asshole who’s a bigger asshole than any assholes you have met, where the hole in the word asshole becomes bigger, deeper, darker. Shit gets deep.

“You abysshole.”

Abysshole by Alan Pugach Barker April 25, 2019

Ripped him a second asshole 

This is not solely applicable to blokes, females can also get a second asshole, so feminists eat your fucking hearts out. The phrase originated in the UK where it was usually “ripped him a second arsehole” but over time the spelling changed. The original meaning was to attack someone, usually unexpectedly, brutally and viciously so that they were completely overwhelmed and unable to defend themselves. It can also mean to criticise someone’s thoughts, ideas or lifestyle either with or without cause or justification. The usually accepted definition is that which is applied to the workplace where it means to reprimand someone so totally and effectively, that the person on th receiving end wishes they could crawl under the carpet and die. So if you have ripped him/her a second asshole you have delivered a rebuke of epic proportions.

That WOFS Malcolm has fucked up once too often so the boss called him in and ripped him a second asshole. He practically crawled out afterwards looking like he’d pissed himself and cleared his desk.

Ripped him a second asshole by AKACroatalin December 6, 2016

Reverse Thornton Asshole Dickfuck 

The sexual act of acquiring an erect penis, and falling face-first, so that ones penis bursts out of the anus. The female then proceeds to straddle the now raw penis.

"Yo Chev, I just saw someone doing the reverse Thornton asshole dickfuck"

"Damn, he alright?"

Reverse Thornton Asshole Dickfuck by Jerome Momas December 24, 2013

assholeitis 

A disease in which a teenager regresses in a fit of narcissism, self-centeredness, and egocentrism, refusing to be accountable to own behavior, projecting anger, rage, and immaturity throughout the world, with a sprinkling of ass-holeishness.

A person with assholeitis may display: Screaming in parents' face, in a high pitched, screeching, nonsensical grandiose way, in an attempt to be re-breastfed. A person with assholeitis will also display pervasive denial. (Seek attention from perturbed, tired, teenage peers.)

assholeitis by RESCU May 13, 2009

Mike Pompous Asshole 

An already widely popular nickname for the Trumpster’s third Secretary of State, Mike Pompeo.

Well that’s a big surprise, Mike Pompous Asshole is a proud member of the Impeachment Posse for the role he’s played in the recent intercontinental extortion attempt!

Mike Pompous Asshole by Dr Bunnygirl September 30, 2019

Shy/Asshole Confusion 

Coined by Larry David in the "The Acupuncturist" episode of HBO's "Curb Your Enthusiasm", Shy/Asshole Confusion is when one mistakes a shy person's quiet demeanor for that of an asshole.

Larry: I don't know why you call him an asshole. He's not an asshole, he's just shy.

Cheryl: No, he's not shy. He thinks he's smarter than everbody else and he sits there and he judges and he-

Larry: No, he doesn't, he's just shy! You've got shy/asshole confusion, my friend.

Shy/Asshole Confusion by Meeyort Snurn May 22, 2008

Poopy Asshole Nigga Fart Phobia 

The fear of having an unclean asshole after pooping, often causing you to wipe more than usual.

Robby - "Why did you take so long in the bathroom"
Todd - "Sorry my Poopy Asshole Nigga Fart Phobia makes me stay in the bathroom for a long time"

Poopy Asshole Nigga Fart Phobia by SimpCity December 15, 2019