• Borstal Boys Fucking With Guard

    Borstal Boys Fucking With Guard

    Steve is guarding the Borstal boys as they are working on their project. He's got a thing for Bulldog Pit's hot lads and he starts to think how he can abuse his power over them, and get them to fulfil his sexual fantasies. It isn't long before our hairy, muscular guard has the boys sucking each other and himself. Pretty boy Rio Francisco is selected to bottom for Will Jamieson, whilst Steve pounds skinhead lad, Ricky Jackson, but Rio's ass is too hot to resist and Steve takes a shine, giving his hole favorable treatment!

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  • Guard and Two Convicts

    Guard and Two Convicts

    After a hard day's work, big bad tattooed guard Darren takes a couple convicts to a private spot and forces them to suck each others' cocks and do some ass pounding for his pleasure... and for the Bulldog Pit cameras. Watching the two guys service each other makes Darren horny as hell and gets into the action, taking control and shoving his dick deep in prisoner Ashley's hole while Ashley sucks cock in spit roasting madness!

  • Fisting Cops - Hump Day Hotties

    Fisting Cops - Hump Day Hotties

    Officer Dolan Wolf has been doling out his nasty brand of justice in Club Inferno Dungeon's new DVD called Long Arm of the Law. Three weeks ago he had Brandon Moore caged in his jail cell. Every morning this perverted police officer comes by to check on his prisoner and shoves his hard dick through the bars -- forget a morning coffee, a blowjob is how this copper starts his day. After forcing his prisoner to gag on his cock, Officer Wolf shoves his fist up Moore's ass.

    Jordano Santoro is another one of the nasty cops in this San Francisco county lock-up and he's got inmate Brian Bonds in cell 142. When Officer Santoro comes along to check on his prisoner, he catches the bad boy jacking his dick. This muscular hunk orders the inmate to stop, and when he won't Santoro enters the cell and gives him five big reasons to stop.

    This week in the third scene, Officer Dolan Wolf has been watching his prisoner Drew Sebastian having sex with the other inmates. Wolf wants in on the action, so he enters Sebastian's cell and orders the bald prisoner to strip out of his uniform and get his legs in the air. The cop fucks his prisoner with his nightstick, then shoves his fist up Drew's ass. And in an unexpected turn of events, this dirty prison guard lets Sebastian strip off his uniform and gives him a deep cavity search.

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  • Pervert Fucked in Jail

    Pervert Fucked in Jail

    Caleb Colton is a perverted sex offender and he finds himself in the Bound Gods jail. Connor Maguire is the new office on duty who is assigned the task of watching over this nasty prisoner.

    Office Maguire decides to see just how perverted this prisoner is. Caleb has been locked in a chastity belt and blindfolded, so he's of little threat. Maguire enters the jail cell and makes this pervert swallow his big, fat cock. Then the jail guard opens up the prisoner's asshole with his night stick.

    After a severe flogging, Caleb is suspended from the ceiling and the officer fucks his ass good and hard and blows his cum load all over the prisoner's face. Then the prison guard lets Caleb jack off all over his boots, but he's forced to clean up his mess with his tongue. Turns out this sex offender is pretty perverted, indeed.

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  • Jail Sex - Hump Day Hotties

    Jail Sex - Hump Day Hotties

    We do love our men in uniform, so this week GayDemon's Hump Day Hotties Wednesday feature is taking us through the gay porn penal system. In Gag Order from Next Door Buddies, Ray Diaz finds himself pulled over on the highway and he's detained in the back of constable Vinny Castillo's police cruiser, and he's on his way to jail and facing a heap of charges. But officer Castillo is a reasonable cop, so he offers Ray a choice: take his chances in jail or give this policeman a blowjob. Ummm ... look at handsome hunk Castillo and his big cock -- it's a no brainer

    cops-gang-banging-prisoner.jpg

    Had Ray Diaz decided to take his chances in jail, he could have ended up like Jeremy Stevens, a new inmate in the Bound in Public prison. Stevens is ordered to strip for a full body search as a part of his processing into this nasty jail. Stevens is a high-risk sexual offender, so he's locked in solitary confinement. But when he goes on a rampage destroying his cell, they call in the riot squad.

    Five officers wrestle this pervert into restraints, then they force him to suck dick -- lots of dick, five cocks to be exact. Then the officers pin this sex offender down and let one of the other inmates fuck his ass. With his ass thoroughly pumped, it ain't over for Stevens; the five riot squadies line up with their hard cocks and they each take a crack at his fuck hole.

    parole-officer-fucking-ass.jpg

    But even after a prisoner has done his time in jail, he's still not completely free. All he can hope for is that he doesn't end up under some nasty parole officer's charge like this poor bastard over at Parole Him. Muscle dude Darius Soli has shown up for his weekly appointment with his parole officer and he's bent over the desk for a cavity search. When the parole officer whips out his hard cock and sticks it into Darius' beefy ass, there's nothing the ex-prisoner can do but take it. If he wants to stay out of jail so he can keep fucking his girlfriend, he'll shut up and take it up the ass.

  • Cellmates Andy Robindale & Andrew Markus

    Cellmates Andy Robindale & Andrew Markus

    Andy Robindale and Andrew Markus are playing cellmates in this new scene from Next Door Twink. And the site is giving you a hot opportunity to check out the horny twinks over there, from now until March 18 you can grab yourself a 50% discount, and with access to 12 other gay porn sites, you won't find a sweeter deal right now!

    Andy and Andrew have been out partying hard all night, and when they wake up the next morning they find themselves in jail. Since there's nothing else to do, these hot horny boys continue the party and get into some hot sucking and fucking in their jail cell.

    It takes a bit of doing, but finally Andrew's throat loosens up enough to swallow Andy's fat cock. Then Andy lies back on the bed and Andrew climbs on top to ride his big stick. Bouncing up and down on Andy's cock, he begins to realize that maybe things in the big house won't be so bad after all.

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  • Please Go Easy On My Ass, Sir

    prisoner fucked by his parole officer

    Liam Grant is only 21 years old, but he's already been in a heap of trouble, and he thinks he's a real tough guy. In the beginning, Grant wasn't taking things very seriously. His parole office decided this thug needed an attitude adjustment.

    It's been several months since Grant's first meeting with his two parole officers at Parole Him and he knows the drill by now; if he wants to stay in their good graces and keep his ass out of jail, he'll service their cocks and bend over when he's told to.

    After a brief check-up on how things have been going, the parole officer starts rubbing his crotch. Grant doesn't even flinch, he just drops to his knees, unbuttons the officer's pants, and starts giving him head. And when the officer's dick is rock hard, Grant stands, Grant pulls down his jeans and gets down on all fours. "Please go easy on my ass, Sir." Easy? He should have thought about that before he thought assaulting people was fun.

  • Tender Twink Ass-Fucked by Prison Guards

    Tender Twink Ass-Fucked by Prison Guards

    This twink's got double trouble on Men.com. First off, he was busted and thrown in jail... And in case that wasn't bad enough, these two big, strong and horny guards have decided that they want some of that sweet ass of his, so they tag team him and give his hole a serious jail house pounding!

  • Nasty Parole Office and the Immigrant

    cop fucks parolee

    Rafael Mendoza just finished a 5-day stint in jail for a minor possession charge. He was released and assigned to Officer Thompson. This 25-year-old parolee's troubles have just begun. He met with parole officer Thompson and his sidekick Johnson for his first interview.

    Mendoza managed to avoid getting his pretty Latin butt fucked in jail, but he's not going to be so lucky today. Thompson and Johnson put the screws to Mendoza and give him one option: get on his knees and start sucking dick or they'll report is undocumented family to the immigration authorities. What's a guy to do?

    Officer Thompson sits back in his chair while Mendoza sucks his big cock. But this parole meeting isn't going to end with a blowjob. Mendoza is stripped naked, forced to lie back on the desk where Thompson fingers then fucks his tight butt hole before he takes the bald officer's cum load. If Mendoza wants to keep himself out of jail and his family in the country, he can look forward to servicing his parole officer every couple of weeks.

  • My Hunk Prison Cell Mate

    View full video at Scary Fuckers

    Being stuck in a prison cell with Bubba, or some massive man named Brick or Big Luigi, is most guys' worst nightmare. But this cock-hungry bottom doesn't seem to mind having his prison cell mate fucking his ass. In this Scary Fuckers video, the prisoner bends over the cell sink, hikes his foot up on the bars and gets his ass drilled good.

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