Jizz

Standing up for your beliefs is hardest against those you love...but I spoke out about a prison rape joke my mother posted to FB. (My response in purple, forgive the horrible laptop editing!) [NSFW]

TwoXChromosomes

One tanned girl with a strapon in some sort of prison corridor

Pegging

When I finally escape the war prison I've been in for 10 years but don't have any weapons

shittyreactiongifs

Soviet soldiers who died of hunger and exposure as German prisoners in Stalingrad, found after the battle, 1943. [1200x1756]

HistoryPorn

[SPOILER] I thought that I had heard a familiar voice. TIL that Serena Williams voiced both the first female sage in Beginnings and Ming the prison guard from The Day of Dark Sun: Part 1.

TheLastAirbender

One of the cells of the former abandoned prison in Hasselt, Belgium, now a lawschool [OC] [400x600]

AbandonedPorn

What really happens in women's prisons

stockings

Looks like she's in an Afghani prison. Let's go save her. (via /r/hersheyskisstits)

Puffies, RealGirls, hersheyskisstits

Sat in on interview with older gentleman who recently left his job as a male prison guard. He did not like his female counterparts.

AdviceAnimals

Soviet Major-General Vasily Mikhailovich Blokhin served as the chief executioner of the Stalin's NKVD, is known for executing tens of thousands of prisoners by his own hand, making him the most prolific official executioner in recorded history, executes P

HistoryPorn, NoSillySuffix

For some reason, Sasha asked to do her time for prostitution in the men's prison

anal

Want to be in her prison?

OppaiLove

Chinese prisoners, possibly Boxers, beheaded in front of a group of Chinese and Japanese officials. Boxer Rebellion, 1899-1901 [NSFL] [2699x2135]

HistoryPorn, pics, HistoryFans, NoSillySuffix

Popular Prison in the comic book world

Daredevil, Gotham, Defenders

Sad to say my cousin posted this to FB. He's Facebook friends with all of my super Christian aunts. He's also fresh out of prison...also WHO WOULD SLEEP IN IT!?

trashy

Abandoned prison in France, vandalism lvl: max

urbanexploration

Our favorite prison makes a guest appearance in another show. [Maybe spoilers for people episodes behind]

Gotham

Man's last moments as he's hacked to death - looks to be in a South American prison

watchpeopledie, poamcstwd

I don't think I have the necessary restraint to work in a womens prison

Boobies, BigHolyTits, JustTitsXXX

Rule 34 - There really is porn of everything on the internet: Rover (from The Prisoner - 1967) in a threesome!

NSFWFunny, bestof_gangbangs

Vina in one bar prison

Bondage, OnOffBDSM

Maybe I’ve seen too many prison movies, but I wanted to establish dominance early when moving in with my step family.

gifcest

Pictured before their arrest and incarceration in a sexy lady's prison - The Boob Squad, and their infamous well-oiled guns

GroupOfNudeGirls

My titties are freshly released from their 10 hour stint in bra prison!

GoneWildPlus

My poor girls are bruised up after spending the day in boob prison. Might be time to throw out that particular bra.

BigBoobsGW

Beautiful Prisoner (album in comments)

FantasyGirls

We ran a (legal) patrol through a school before it was torn down. Our bazooka man took out a whole tan squad in dramatic fashion. One survived so we got ourselves a prisoner too!

GreenDawn

Sex in Chains (1928) was a German film that advocated for prison reform, including for allowing inmates to have conjugal visits

silentmoviegifs

Outbreak in Arkham: Catwoman Prison Gangbang (CHOBIxPHO) [Batman]

rule34

Azula loves servicing the guards in the prison yard [Avatar: The Last Airbender] [The Boiling Rock] (MrPotatoParty)

rule34, AvatarPorn, u_azllerkun, u_ifuckedyourboi

A prisoner in the mud...

Nedda_A, MudGirls, u_bryandeanscheibe

6 months in orc prison

Preggo_Shops, preggohentai, u_Ancestralweed

failed to escape prison in time

hentaibondage

Wearing your prison shorts in front of your trailer.

beholdthemasterrace

starting to feel a little more comfortable in this flesh prison

Safe4Trans

Dead Polish prisoners lay in a ditch. After being summarily executed by German soldiers of the Wehrmacht 29th Motorized Infantry Division. Ciepielów massacre, Poland, 9 September 1939. [800 x 812]

HistoryPorn

Dead Polish prisoners lay in a ditch. After being summarily executed by German soldiers of the Wehrmacht 29th Motorized Infantry Division. Ciepielów massacre, Poland, 9 September 1939. [800 x 812]

wwiipics

People of Rostov-on-Don in the courtyard of the prison identify relatives killed by the German army

MorbidReality, Holokauston

Uschi Digard in the 1972 film "Prison Girls"

celebnsfw

Three death row inmates escaped their prison yesterday in Egypt by digging a hole into the wall over 3 months, using a metal pipe.

Crime_Scenes

Coated in Everything [Eliza Perlman - Prison Academia]

rule34pee

it's milking time and nellie is hiding again basking in the sun. she won't be far away tho this farm is enclosed like a prison

futanari