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The Gates of Hell 

The Gates of Hell is male chastity devise.

It is 3-7 rings from 2" diameter, down to 1" diameter.
The steel rings are connected by a 1/2" leather strap
It limits an erect penis to a confined space, making it extremely difficult to ejaculate.
The Gates of Hell is male chastity devise.

Bob wore "the Gates of Hell" to pleasure his woman.
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The Gates of Hell 

the big JC and his blast beats that rain down into the gates of hell. its a very scary and loud place located near the junction in middletown,nj. its nothing but sweat, catpiss, blast beats, and random jizz stains all of the bed. many scene bitches hang out here.
" dude its about to jim chesek out.."

"yeah The Gates of Hell man"

The Gates of Hell 

During anal intercourse in the doggy style position - the male quickly pulls out of the female's anus, then moves towards the vagina. Before entering, the male pulls apart the labia, imitating gates to hell and thrusts inside, all whilst laughing maniacally like the Devil. In the confusion, pleasure, and potential pain, the female will likely turn round and hit the male, most commonly on the erect penis, thus with the pain imitating the fiery chasms of Hell.
Man 1: "Bro I did The Gates of Hell on her last night!"
Man 2: "WTF no way! Did your dick burn afterwards?"
Man 1: "Yeah, after the turned around and slapped the fuck out of it."

I would rather walk briskly through the gates of hell than

A phrase which is used to emphasise how much the speaker wishes not to do or take part in some activity, used as a response to a suggestion or request.

Comedic value is gained from the over emphasis of how much the person would not like to do said activity.

May have origins in a quote from the popular computer game "The Curse of Monkey Island" released on Windows 9x

Murray: You may call me ‘Murray’! I am a powerful demonic force! I am the harbinger of your doom! And the forces of darkness will applaud me as I stride through the Gates of Hell – carrying your head on a pike!
I would rather walk briskly through the gates of hell than attend a Justin Bieber concert.