Jizz

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

NSFWFunny

Send me to jail, cuz i'm naughty [f]

gonewild

Why I never want to go to jail

blackpeoplegifs

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

FacialFun

Good night! Thought I would li[f]t my top just before bed to let my boobs out of boob jail. Enjoy x

gonewild

Four men removed from town jail by angry mob and lynched - Yreka, CA - Aug, 26, 1895 (2048x1240)

HistoryPorn

Just (f)inished at gym, time to release the twins from boobs jail

gonewild

[M/M/M/M] The Jail of the Jade

yiffcomics

Breaking out o(f) booby jail!

gonewild

Hot brunette rides in jail

nsfw_gifs, NSFW_GIF

She escaped from jail, her nipple escaped too

nipslip, accidentalnudity

Hope this man is jailed

badparents

In LA County Jail, you can trade 200 cigarettes for...

cardsagainsthumanity

Jessica was caught stealing. She chose becoming a pet over spending 7 years in jail.

Fretton

Cops jailed

NSFW_GIF, ass

Avoiding going to jail on spring break [bondage]

xxxcaptions

Hot times in the county jail.. Jason Hawke

UniformedMen

(F)inally free from boob jail

gonewild

Link, Marth, Zelda and Lucina make the best out of jail time [Inusen]

smashbros34

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

gonewild

[Selkie] Sure you will probably get sent to jail for beastiality but who else can say they fucked a mythical creature?

Fire_Emblem_R34

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

ladybonersgw

The bastard was blackmailing her but she'd do anything to avoid jail time

frenchmaid

When American police respond to domestic violence, the man is usually hauled off the jail for a night. In the Islamic world, the women is physically punished by the local males.

The_Donald

Free from boob jail

bigboobs

Go to jail, certainly.

handholding

Keepin' it TTD in jail

Ice_Poseidon

If she were my nanny I'd be in jail

JeffMilton

[F]reshly out of jail, brought back a souvenir

gonewild

Breaking: Prince Harry will also soon be sent to jail

ImGoingToHellForThis

Bernice Berinice fucking her way out of jail

anal

Pawjob [MM] by Jail-Bird

yiff

Just home from a year in jail

MenGW

Time to get back in your jail!

ShinyPorn

Little ass in jail

CuteLittleButts, WhatAnASS

Bra are just boob jail.

braless

Welcome to futa jail

futanari, HorsecockFuta

in gay jail for being too horny ?

Safe4Trans

Irene Miracle, Won a Golden Globe for her emotional role in Midnight Express (1978). She went on to have a successful career. (Her topless jail visit scene in the comments)

vgb, WatchItForThePlot

Booty jail

altgonewild

Should be fun back at the jail.

MaleCall_PublicNature, blondmennsfw, dudestuff, Gayexhibitionist, gaynsfw, GaySocksAndSneakers, UniformedMen, GayPlusNudists

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

StuckHentai

Sal Mineo (age 30) and Don Johnson (20) in erotic jail scene in LA production of the play Fortune and Men's Eyes (1969)

CelebrityManAss

Jill avoids real jail by offering Chief Irons her pussy (m1stermorden)

Rule34ResidentEvil

Bootyhole jail. Set her free!

asshole

[Hypnosis/Suiting] Welcome to the Horny Jail by Porniky

Inanimate_TFs

Aunt Becky before jail

MotherDaughter, TrueFMK

Taihou in horny jail

hentaistraitjackets

She was expecting a very active night in jail.

bondagehumor, Bondage, u_SubjectiveCock

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

bonk, goto horny masochist jail

goodanimemes, hentaimemes

*Bonk* you are sentenced to horny jail

ladydimitrescu

Get Out Of Jail Free Card

ElsaJean, nsfw

*bonk* come to my horny jail ?

altgonewild

Going To Horny Jail [Tom Strong's Terrific Tales #3]

ComicPlot

It's me. In horny jail with you all. [F]ree use for all

gonewild

uhh jail time?

LoudHouseRule34

Horny Jail: The new Inmate

hentaistraitjackets

A Khayon bonking gif, for all your horny jail needs (sfw)

u_Vezimira

Pilot jailed for upskirting

Shittyaskflying