Jizz

just in time for halloween

jail_bait

Dolan in jail

dolan

"In most places this guy would be in jail with a sex offense, but in Baltimore this guy could run for city council with this pic (and win in district 9 depending on who his mother is…)." [NSFW]

baltimore, WTF

If you are ever locked in jail without a cup...

NSFWFunny

In jail

Tgirls

One for The Cum Facial Museum (yet another Peter North entry!) - Cindy Hope gets her face creamed in jail. (GIF)

FacialFun

What happens in jail stays in jail!

pokemon

What happens in jail stays in jail!

funny

In Jail Boobs Press

interraciallesbian

Thailand - 2 years in Jail and 20,000B fine if foreigner does not have travel document in his(her) possession.

backpacking

Hot brunette rides in jail

nsfw_gifs, NSFW_GIF

We are talking about her biological brother, who is in jail. NSFW

trashy

In honour of him being arrested, he's a gifof him in jail

TotallyStraight

Daughter visits her father in jail

wincest, 2roundup

[NSFW] My highschool times friend just posted this on FB. He was in jail 2 times since and was last released 1 month ago.

trashy

I wish these batman socks had kept me (f)rom being in jail the past 2 weeks!

gonewild

This is what 45 days in jail does to a body.

ladybonersgw

"has my future stepdad* in jail" FIFY

BlackPeopleTwitter

Throw his ass in jail

ImGoingToHellForThis

Everyone's having fun in Venus, and I'm in jail...

FemdomMatriarchy

Keepin' it TTD in jail

Ice_Poseidon

/pol/ on masturbating in jail

4chan, DankMemeArchive

I wonder why they are in jail. Chanel Santini and Kimber Lee

ShemalesParadise, jobuds

Spending a night in jail

Futadomworld

Just home from a year in jail

MenGW

What would you do to me? (F)uck my pussy raw ??, suck this long clit like that dick in college ?, or eat my ass like your in jail. ?? *had to delete before* so here it is too stay ???

gonewild

Her boyfriend is in jail for stabbing her, she's also 4 months pregnant.

TrashyFacebook

Little ass in jail

CuteLittleButts, WhatAnASS

Jolyne and Ermes killing time in jail by BangDacy[Stone Ocean]

JoJo34

NSFW: Woman allegedly raped, sodomized, beaten, and failed to get medical care in jail by cops/staff. Went into a coma yesterday and died today. Link in comments

TwoXChromosomes

Chapayev in Jail

AzurLewd

I was staring at this chick’s ass when her bf started yelling at me. Right before he got close, I swapped with the chick and watched her bf kick my body’s ass. She’s in my body in the hospital, her bf’s in jail, and I decided to go with the flow in her ho

bodyswap

In Jail

MeganMarxxx

"You know what's gonna happen. They're gonna get caught and thrown in jail. Then I'm gonna have to shake my ass at somebody to get them out!" ??

ThickThighs

Onami tied up in jail [One Piece](Raida)

StuckHentai

Nami in Jail

funpiece, HentaiCity, NamiSwan

Angela White in VR scen "Nailed In Jail"

pornVRbest, AngelaWhite

I present to you: Plugnar, the new and improved Duke of Flanders. All hail Plugnar! (PS he was immediately thrown in jail by the king of France)

CrusaderKings

After six years in jail he's going to be mad when he goes to see what you watch with a broken heart! and since she refuses him nothing ...

HeStoleMyGirl, xxxcaptions, CheatingCaptions, cuckoldcaptions, u_GangbeatsFR, u_pitchardg

Fucked by Chanel Santini in jail

TSKimberlee

Harley Quinn in Jail [Batman]

CamSluts, rule34, superheroporn, u_Lycanthropic_Deviant, u_texashellyea

In jail with Chanel Santini

TSKimberlee, u_Shemale6911