Penitentiary Chances 

Engaging in a highly risky act (usually illegal) that has the high possibility of landing one in jail or prison.

Bitch please. I'm not smoking weed in public. I don't believe in taking Penitentiary Chances.

Penitentiary Chances by menoenglish April 20, 2017

punitentiary 

An emotional experience describing how incarcerated a person feels when they can’t escape the company of a constant punner.

I’ve been stuck in this punitentiary since the day I married him!

punitentiary by Dr Bunnygirl June 6, 2021

penitentiary 

actually it means jail. penitentiary is a big cage, where people are being changed in a good way.

Heeey! I see the penitentiary, one day
And runnin from the police.....

tupac shakur(dear mama)

penitentiary by don_makaveli April 23, 2006

penitentiary style 

when you have violent anal sex with a someone as though you were in jail. this is usually done without consent and without a condom. it often involves the transmission of STDS especially HIV

once Ndu walked into cell block D, he knew he was going to get it penitentiary style -- now he has AIDS;

at the rape party, everyone was getting it penitentiary style

penitentiary style by evillestdude May 6, 2009

penitentiary 

penitentiary - to qualify as a penitentiary, it must be a large, maximum security prison. the word, penitentiary is from the latin, penitent, which means to repent, be sorry for, or pay for one's mistakes. Its Latin root is: paenitent - repentent. prison jail hoosegow the big house deadlock lockdown the block the slammer stoney lonesome con college club fed calaboose the hole the joint the clink jailhouse

Yuhto was wrongly convicted of murder in the first degree and sentenced to fifteen years in Schelgar Penitentiary of the State of California, an enormous, poorly maintained maximum security prison. (paraphrased - from the novel, Deadlock, by Aida Saki and Takashina Yuu)

penitentiary by raindragon June 2, 2017

Peenitentiary

Locked into an unhealthy relationship for a good sex life.

"He treats me terrible, but the sex is good, I feel as though I'm locked in a peenitentiary"

Peenitentiary by Lesismas August 17, 2017

penitentiary 

jail

"Ever since a nigga was a seed only thing promised to me was the penitentiary..."

penitentiary by pwnz0r September 19, 2003