Jizz

Pony Prison Petting (art by The_Weaver)

mlpmature

Ebensee, Germany: The body of an S.S. guard lies in a ditch. He had been beaten and stoned to death by liberated prisoners. ca. 1945 [500x286]

HistoryPorn

Five SS soldiers being led past the corpses of their former prisoners to their execution, near Nammering, Germany, May 6, 1945. They changed into civilian clothes in an attempt to evade capture.

WW2Photographs

South Central Los Angeles prison where inmates are treated with serious love has the lowest reoffending rate in California

Cholojerk

Two prisoners against a wall. They know what's about to happen to them, and they can't wait, the little sluts.

Cuffs

You have 100 points to spend to improve your stay in The Sissy Prison

Sissies

This guy thought he had the best tattoo ever, until he went to prison. [NSFW]

funny

Not all feminists were immediately enslaved upon arrest. Political prisoners were often bought up to inhabit ranches where wealthy businessmen would pay top dollar to go on "cuntmeat safaris" and take ownership of whatever they captured. To the left is a

breakfeminazis

Looks like the makers of Prison Architect are excited for Season 2, too!

HouseOfCards

NSFW; Graphic: New photos of the detainees in Syria-an secret police Mukhabarat prison branch 215 from Zaman Al-Wasl (1/5) (others in comments)

syriancivilwar

(F)ree at last! Feels good to have the girls out of their prison.

gonewild

Paying the death penalty for crime - garroting a criminal at Bilibid Prison, Manila, P.I. 1901 [1423x1536]

HistoryPorn

Shot from the Italian film "Love in a Women's Prison" - just added this to my must-see list.

ass

This has to be the worst use of a glass prison I've ever seen (Batman Eternal #35)

comicbooks

Victoria Vetri: American actress, model and would-be murderess, on TV and in B-movies from 1962 – 1975, Playboy’s Miss September 1967 and Playmate of the Year 1968 (as Angela Dorian), sentenced to 9 years in prison in 2011 for shooting her husband.

Playboy

We have the safest prison system. Guns, bullets and what?!

funny

Should've stayed at the fucking prison

treatemright

She works in a prison. Could you imagine what the inmates would do to her if there was a riot??

WouldYouFuckMyWife

Don't drop the soap [Prison School]

animenocontext

TIL the Bible predicts that during Armageddon Bernie Sanders and John Cena will team up to seal Trump away on a prison on Neptune

circlejerk

[Request] Sarah Wayne Callies of Prison Break and The Walking Dead

doppelbangher

3D CG: Harley Quinn in Some Prison Love with the Dark Knight

nsfw_3D_porn, AnimatedGIF

Ustaše militia execute prisoners near the Jasenovac concentration camp, between 1942-3 [2045 × 1073]

HistoryPorn, HistoryFans, NoSillySuffix

[H/M] Prisoner of the Tribe [Rokemi][OC][Slavery]

yiffcaptions

Bodies of three Soviet prisoners of war near the fence of an unidentified PoW camp. 1941-1945 [3500x2482]

HistoryPorn, NoSillySuffix

This is your new prisoner for the day

funpiece

As soon as I returned from visiting the Empire, I decided to visit my vip prisoner

FemdomMatriarchy

[/r/the_best_nsfw_gifs] guilty women, prisoner

porn, HDPornGif

Interrogating the Dark Eldar Prisoner by misterjer

Warhammer_Smut

I am begging the new Queen to please show me mercy and release me from my eternal prison sentence.

FemdomMatriarchy

After the sudden and unexpected outburst from prisoner RNS0021, I feel that it's important to increase her medication dosage until she becomes more docile and cooperative.

FemdomMatriarchy

Zombycandy vs the 1Bar prison

Bondage

Heiress Patty Hearst leaves the Federal building in San Francisco on April 12, 1976, hours after she was sentenced to 7 years in prison for bank robbery. Later President Jimmy Carter commuted her sentence to 22 months - [2048x1343]

Cuffs, girlsinhandcuffs

If your sister remembers this in the morning, you're going to prison. [Rape] [Drunk] [Incest]

xxxcaptions

When Trump gets elected because "We're gonna trigger those libruhls" but actually the whole Republican party becomes a joke when he goes to prison.

u_kenpitt

This is what you all came to see. Gwynne is going to Prison folks. Second DUI, Overdosed, felony murder by vehicle, lying to police about who she is saying she's Jessa, and no license. The full fuck up, she's gone.

FurchesTwins

Sauce help. Looks like from Prison School but can't find the chapter.

HentaiSource

After the shower. They don't like being held prisoner for long

tits, BigBoobsGonewild, AllAboutBoobs, BoobsAndTities, boobs, Nipples, u_BOOBSBIBI, BigBoobsGW, Titties, HugeHangers, hangers, u_sush58, smallboobs, hugeboobs, u_ItsClyde96

Aryan Circle, the lite beer of white supremacist prison gangs.

beholdthemasterrace

I am a prisoner of my immoral desires ... who has the cock key that I need to free myself? ???[Sext][pic][cam][vid][rate]

Sexsells, nsfwbuys

Hanna is taken prisoner during a failed Weatherlight incursion of the Stronghold

mtg_nsfw, GameOverGirls, DeformationHentai, u_SniperBravo7, Hentai_warehouse

NOO Stop it! People shouldn’t be allowed to do this. You shouldn’t make money from a prison. Because then, you’ll try to convict people so you’ll make more money! The law is supposed to be fair and not biased for financial gain.

u_bhexca

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]

GermanWW2photos

After a life of crime, I was about to end it in prison... when suddenly I found myself surrounded by photographers. Completely naked and... with breasts? "Well... Holly ? Are your OK ? Can we proceed with the photo shoot?"

OldAgeRegression

Who said prison YouTube is dead? Larry with 43k views . The only dead thing is aps with 10k views

AfterPrisonShow

Continuing the trend of Prison Pekora's lewd conducts

Hololewd

Posting WW2 stuff on a semi-regular basis until I forget I started doing it | part 583: Italian POWs are marched into a prisoner camp following the decisive British victory at Sidi Barrani, Egypt, 10-11 December 1940.

worldpolitics

Trapped by the One Bar Prison

LittleCaprice