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Getting raped so hard in jail by a huge black dick that your asshole requires stitches.
Jeff: How was your 5-year sentence?
Adam: Terrible. Bubba gave me a jailhouse C-section everyday.
An anal raping of such severity that surgical sutures would be required for recovery.
The term was coined by NovaWar on November 3, 2012 on the YouTube channel of LifesAGlitchTV's episode "So Close That Kermit Arrived -- Starcraft 2 LAGTV".
Source: youtu.be/u92PA5wmH1U?t=4m13s
Big Bubba with his big black dick took homeboy's buhymen and gave him a jailhouse c-section.
The act of being anally raped by a large black penis in prison. -Adam of LagTV
When Steven went to jail, he got a Jailhouse C-Section from Big Bubba.
Insane and irreparable damage to one's asshole. Mostly likely to occur in jail, from a huge black man named Bubba with his massive black dick.
Bubba: I'm about to give you a Jailhouse C-Section, prepare your asshole.
Max: What are you going to do to me?!
Bubba: Ask Jeff and Adam, they know all about it.
Being raped in jail by another inmate, that causes the tearing of the anus. May also cause a tear that could be considered a new anus.
Bubba is gonna give you a jailhouse C-section when you get there.
When a large inmate from state prison tears his victim a new hole with his enormous penis, but the victim manages to get the hole stitched up with surgery. Credit for this definition go to NovaWar from LAGTV
Big Bubba hulked over his roomate and told him "Imma give you a jailhouse C-section, com'here boi!
Stitched up tear in one's asshole
""I'm about to give you a jailhouse c-section."
And you are instantly terrified."
-Novawar