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A penetration test, where one “tests” penetration just to see how it feels
“Nate tried a pentest and I guess he’s actually gay.”
Pentest by WugWUG January 9, 2026

pentesting 

A penetration test, or pen test, is an attempt to evaluate the security of an IT infrastructure by safely trying to exploit vulnerabilities. These vulnerabilities may exist in operating systems, service and application flaws, improper configurations, or risky end-user behavior.
I'm pentesting Microsoft's website to see if they're vulnerable for XSS.
pentesting by SevnDev May 25, 2016
She has pengest hair!
pengest by MissBelloChan December 15, 2010

Penestration 

To become frustrated from the inability to penetrate or be penetrated sexually.
Despite copius amounts of lubricant, Carl's fat, girthy cock was simply to big to cram into Dana's tight bung hole. After an hour of trying, they both gave up feeling nothing but penestration.
Penestration by Eaton Holgoode November 18, 2015

pentastic 

Holding back a build up of emotion and then just going forward and leaping into the unknown. The euphoria that creates a pentasm, like many feelings at once hitting you in the face .

The spark in the moment right before you do something for the first time.

Awesomeness.
"Although I haven't said anything to her about it, I think Jules might be the light of my life; It'll definitely be pentastic if I try to tell her though."

"I never tried painting before, but as soon as I grabbed the brush it was pentastic ."
pentastic by sanderjules@gmail.com January 15, 2017

pentester 

A penetration tester, or "pentester", is a security specialist tasked with penetrating an organisation's most attractive assets and confidentially revealing all to management. They carry a bag of exciting devices, and tend to enjoy testing the human element of security the most.
Despite the inexplicable innuendo of his industry accepted job title, Bobby the pentester spends his days being tested by uncooperative staff, poor procedures, and red tape. Nobody likes the bearer of bad news.
pentester by mountedandloaded November 28, 2019
Word of the Day on January 8, 2026
More from Urban Dictionary
anyone who succeeds in disgracing/over indulging themselves in the throws of clubland
28 hours and 4 clubs later, gurning for england but still refusing to go home - a total wrongun!!
wrongun by bevvers March 21, 2007
Word of the Day on October 8, 2026

square grouper

Nickname given to bales of marijuana thrown overboard or out of airplanes. Origin is reportedly from members of the US Coast Guard in the area of Southern Florida.
"Base we've got some square groupers floating outside of Miami harbor."
square grouper by slipsheet November 6, 2004
Word of the Day on October 7, 2026
A girl who does ballet and only talks about ballet. Her schedule is filled with dance classes which does not allow her to do any other activity.
"Hey, do you know that girl Sally?"

"Yeah, she's kind of annoying. All she ever talks about it ballet."

"Wow, what a Bunhead."

"Hey Sally, you want to hang out this weekend?"
"I can't, I have dance."
"You're such a Bunhead."

"Yeah... I know."
Bunhead by Jen00 October 24, 2014
Word of the Day on October 6, 2026

trucker's tan 

A sunburn or suntan focused on the left arm. It is caused by the left side of the body being the only half that gets exposed to sunlight while driving. Presumably, it would be located on the right side of the body in countries where they drive on the left side of the road.
I had a trucker's tan after driving for 10 straight hours on a sunny day.
Word of the Day on October 5, 2026
The phenomenon where adults salivate at children's toys
Every time I walk into the toy aisle, I catch myself kidulting over the latest action figures and LEGO sets!
kidulting by Emotional Cruiser October 12, 2025
Word of the Day on October 4, 2026
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