Prison

Pages: NEXT ►

Order by: Popular Date Relevance

RawFuckClub Violating The Muffle

A captured prisoner is under military..

Added: 2025-09-09 Rating: n/a

Steaming Army Fucksluts

The cops in charge of this special holding unit..

Added: 2025-09-07 Rating: n/a

BoysHalwfayHouse Incident #420 - When It Rains, It Pours

He left our care a year or so ago with some..

Added: 2025-09-05 Rating: n/a

Prison - Instructing of Folks 360p Part 2

本だけが友達だった真面目な幼顔の..

Added: 2025-09-04 Rating: n/a

Walter Uwe - Smacking

Tom breaks into the buttmacineboys building to..

Added: 2025-09-02 Rating: n/a

Brutal Ajax 2 - Just Outta Prison

Greek gay-for-pay hunk Ajax had just conformed..

Added: 2025-09-02 Rating: n/a

Tono Milos - Slapping

With the jail guards finally gone, Tono Milos is..

Added: 2025-09-02 Rating: n/a

Insatiable Weirdo Takes Some Raunchy Justice

Creepy voyeur Griffin is toughly dragged into..

Added: 2025-08-30 Rating: n/a

Fresh St8 Acting Authentic Scally Dual Cherry Popping Jism Stupidly

Fresh st8 acting authentic scally dual virgin..

Added: 2025-08-29 Rating: n/a

Igor Lucios Scn. 32

Igor Lucios have gotten pretty busy in here...

Added: 2025-08-29 Rating: n/a

Prison Break

Officer Johnny Donovan is defeated by inmate,..

Added: 2025-08-29 Rating: n/a

Rock Candy Jail Studs Episode 4 - Masochistic Guard

In prison, rigid guys scratch their itches by..

Added: 2025-08-29 Rating: n/a

Officer DelRay has his Prisoners on Brink

Precedingly new-comer Correctional Officer..

Added: 2025-08-28 Rating: n/a

The Climax - Managed Prison 480p Scn. 1

から2を制作し始めて2年、..

Added: 2025-08-27 Rating: n/a

Derek - Audit - Devin Trez and Derek Cline - 1080p

Derek Audit have gotten pretty engaged in here...

Added: 2025-08-26 Rating: n/a

BoyNapped Using Desperate Serg - Part 3

Serg has been needing to cum since the highly..

Added: 2025-08-24 Rating: n/a

Casey Everett Abducted and Smashed by Logan Stevens

Logan Stevens brings his big, meaty spunk-pump..

Added: 2025-08-24 Rating: n/a

Jail Plowers

The prison guards at this prison may be tough,..

Added: 2025-08-24 Rating: n/a

Deceptive Detainee

All hell violates liberate when deceptive..

Added: 2025-08-23 Rating: n/a

Kevin Texas and Michael Mission Moist 1080p

Kevin texas and michael mission raw, Zack..

Added: 2025-08-23 Rating: n/a

Using Desperate Serg, Part 3 720p

Serg has been needing to jizz since the highly..

Added: 2025-08-22 Rating: n/a

Stolen Valor

Johnny Ford is attempting to get his life..

Added: 2025-08-22 Rating: n/a

Kinkmen - Hetero Hate-Monger Gets His Backside

Max Cameron has just completed painting..

Added: 2025-08-21 Rating: n/a

Michael DelRay Captures, Binds Up, & Humps Nic Sahara Wet

Locked in a clock tower, tied up with cord to a..

Added: 2025-08-20 Rating: n/a

Paying The Piper

Officer Michael DelRay waits eagerly in an open,..

Added: 2025-08-20 Rating: n/a

Muscle guy Cliff Jensen lays claim to jail mega-bitch Tony Orlando

C.O. Sebastian Keys drops off fresh encountered..

Added: 2025-08-20 Rating: n/a

Kinkmen - Lieutenant Wilde's Extraordinary Justice

Lieutenant Christian Wilde devoted this whole..

Added: 2025-08-19 Rating: n/a

Kinkmen - Officer Chief Is The Boss!

Kinkmen fave Jordan Chief makes his mansion Dom..

Added: 2025-08-19 Rating: n/a

Bad boy inmate Cliff Jensen cracks in fresh guard Michael DelRay

It´s a calm day on the cage block and bad..

Added: 2025-08-18 Rating: n/a

DreamBoyBondage Violating Diego - Chapter 6

Despite hours of non-stop torment and..

Added: 2025-08-17 Rating: n/a

Prison Wc Bullies

At very first light kiss, then jacking and..

Added: 2025-08-17 Rating: n/a

Naughty Cop and The Sex Offender

Sex offender Caleb Colton is locked up in..

Added: 2025-08-17 Rating: n/a

Officer Maguire hammers and penetrates a boy for littering

German hunk Alexander Gustavo is brought in by..

Added: 2025-08-17 Rating: n/a

Arrogant Cop Tantalized by His Prisoner

Officer Eli brings in rock-hard criminal Cub..

Added: 2025-08-16 Rating: n/a

Detained Man Faces a Horny, Masochistic Agent

It´s dark, and Tommy Regan can´t move. Heavy..

Added: 2025-08-16 Rating: n/a

Kinkmen - Cage

No escape. No exit. Seamus O´Reilly paces his..

Added: 2025-08-16 Rating: n/a

Boy, it's not a costume... it's leather!

Leather dom Adam Herst ambles into the shower to..

Added: 2025-08-15 Rating: n/a

Officer Maguire and his fresh jail hoe

Kip Johnson has been brought in for questioning..

Added: 2025-08-15 Rating: n/a

The Fresh Officer Maguire and The Mischievous Orgy Offender

Fresh officer on duty, Officer Connor Maguire..

Added: 2025-08-15 Rating: n/a

New meat inmate for Officer Maguire

Deep inwards Kink Prison, Officer Maguire brings..

Added: 2025-08-14 Rating: n/a

Fresh muscular inmate at the grace of Officer Connor Maguire

Seth Santoro waits in his jail box as Officer..

Added: 2025-08-14 Rating: n/a

Super-steamy Fresh Marionette Drake Temple

Drake Temple is in distress in Major Josh..

Added: 2025-08-13 Rating: n/a

The POW

Park Wiley is a strong-willed POW being limited..

Added: 2025-08-12 Rating: n/a

BaptistBoys Adam Kylan Vol.1 Altar Call

When Fruits of Life opened down the street all..

Added: 2025-08-10 Rating: n/a

Sprung fuckfests with muscular guys

Addison Scott and Caesar have been arrested and..

Added: 2025-08-06 Rating: n/a

Plow prisoners in the arse

Jaxton Wheeler showcases Hunk Bryce and John..

Added: 2025-08-01 Rating: n/a

Subjugation Prison, Scene #01 (Nate Grimes, Drew Dixon, Myles Landon)

For some boys hooking up with another man isn't..

Added: 2025-07-30 Rating: n/a

Conformity Prison, Episode #04 (Drew Sebastian, Devin Franco)

This was a long and bland day at work. I was so..

Added: 2025-07-30 Rating: n/a

Row Cum Burst

Repeat offender and energy bottom Jake Morgan..

Added: 2025-07-29 Rating: n/a

Dragon Media - Row Spunk Bust

Repeat offender and power bottom Jake Morgan..

Added: 2025-07-28 Rating: n/a

Subjugation Prison, Gig 04 Drew Sebastian, Devin Franco

Officer Drew Sebastian can't get enough of..

Added: 2025-07-12 Rating: n/a

Catalina Otter Trap

Bear Trap is a Fresh Release Feature from..

Added: 2025-07-11 Rating: n/a

Subordination Prison, Scene 03 Drew Sebastian, Devin Franco

Prisoner Devin Franco is cleaning up a deliver..

Added: 2025-07-10 Rating: n/a

Corey Law

- His name is Corey Law - Him 25 - At a youthful..

Added: 2025-07-09 Rating: n/a

Robber Andrei in Slavery

During the existence of our torment center, we..

Added: 2025-07-08 Rating: n/a

WilliamHiggins Daniel and Cecil - Rough Fucky-fucky - Kink

Daniel Sebesta has Cecil Stok caged, shackled..

Added: 2025-06-27 Rating: n/a

Fetish - Obedience Jail Episode 4

Officer Drew Sebastian can't get enough of..

Added: 2025-06-26 Rating: n/a

Conformity Jail Vignette 4 1080p

Officer Drew Sebastian can't get enough of..

Added: 2025-06-22 Rating: n/a

MenoBoy Eden Omas & Enzo Rimenez - Zoro's Way of Combatting Misdeed

Zorro is haunting after a Brazilian terrorist in..

Added: 2025-06-06 Rating: n/a

MilitaryClassified Ezekiel2 - Anal-Feet

Ezekiel is back and this boy with a gf is ready..

Added: 2025-06-01 Rating: n/a

SayUncle - Hardened Criminal

Apollo is a troublemaker, but his antics come to..

Added: 2025-05-31 Rating: n/a

Kory Part 1

Kory is 100% dude – lean, naturally trimmed..

Added: 2025-05-28 Rating: n/a

Total Knuckle Interrogation, Vignette 5

Nate Grimes is being interrogated for a code..

Added: 2025-05-22 Rating: n/a

Thomas Part Ten

We just can’t get enough of Thomas. We wire..

Added: 2025-05-20 Rating: n/a

MilitaryClassified Montana6 - Blowjob-Rim

What can be said about Montana? This muscle..

Added: 2025-05-18 Rating: n/a

Marshall Mandatory & Severe – Chapter 7

Unclothed naked, every inch of his body shaven..

Added: 2025-05-14 Rating: n/a

Wade Russell Three Days of Agony – Chapter 6

Wade is spread to his cracking point, yelling in..

Added: 2025-05-13 Rating: n/a

Wade Russell Three Days of Anguish – Chapter 9

Wade’s sentence included a severe lashing with..

Added: 2025-05-13 Rating: n/a

Soldierboy

Individual James Grant is a Brit squaddie. A..

Added: 2025-05-13 Rating: n/a

David Webb & Tomas De Rico Sanity’s Threshold – Chapter 3

Sexy blonde David Webb is opened up on his back..

Added: 2025-05-12 Rating: n/a

GayWarGames Blondes Have More Joy - Part 2

The soldier wants his towheaded prisoner to..

Added: 2025-05-09 Rating: n/a

Anal invasion Abyss

Somewhere in the city is a public toilet, run by..

Added: 2025-05-05 Rating: n/a

Penalty for Unsubmissive Prisoner II

A lil warning are: their clothespins..

Added: 2025-05-02 Rating: n/a

Pee Jail

Berlin has got a grubby secret right within the..

Added: 2025-04-20 Rating: n/a

Griffin Barrows

Creepy voyeur Griffin is roughly dragged into..

Added: 2025-04-20 Rating: n/a

Long Forearm Of The Law

The crooked handball activity proceeds in..

Added: 2025-04-17 Rating: n/a

Leo Silva and Alex Meyer

Clients report a brutish incident on the sales..

Added: 2025-04-15 Rating: n/a

Andrew Justice ,Dirk Caber

Andrew Justice has kept his prisoner of war,..

Added: 2025-04-06 Rating: n/a

No condom youngster jail innocents

Young David Contreras discovers the rock hard..

Added: 2025-04-03 Rating: n/a

Menoboy derapages

In Nimes, Inspector Enzo Rimenez is supposedly..

Added: 2025-04-01 Rating: n/a

GayWarGames An Sudden Visitor - Part 3

Tied to the table the youthfull prisoner is..

Added: 2025-03-27 Rating: n/a

GayWarGames An Unexpected Visitor - Part 1

Standa was imprisoned for stealing a military..

Added: 2025-03-26 Rating: n/a

Young Soldiers Humped Firm

Hot, strung up Yankee soldiers John (Ty..

Added: 2025-03-24 Rating: n/a

RusCapturedBoys - Grabbed Paratrooper. Part I

Yet another prisoner of war was delivered to our..

Added: 2025-03-23 Rating: n/a

Tom Deven

Tom cracks into the buttmacineboys palace to..

Added: 2025-03-20 Rating: n/a

Mason Lear ,Max Cameron

Max Cameron has just ended painting straight..

Added: 2025-03-20 Rating: n/a

Jeremy Stevens ,Hayden Richards ,Connor Maguire

In this epic KinkMen Shoot: The cells are utter..

Added: 2025-03-18 Rating: n/a

No condom Gang-fuck At Russian Jail

The guards of this Russian jail are strict,..

Added: 2025-03-16 Rating: n/a

BoLatino Ultimately banged like a tart

This young poon fellow always dreamed to be..

Added: 2025-03-15 Rating: n/a

Connor Maguire ,Alexander Gustavo

German hunk Alexander Gustavo is brought in by..

Added: 2025-03-13 Rating: n/a

Jeremy Stevens ,Caleb Colton

Sex offender Caleb Colton is locked up in..

Added: 2025-03-11 Rating: n/a

Mason Lear ,Max Cameron

Max Cameron has just ended painting heterosexual..

Added: 2025-03-11 Rating: n/a

BulldogXXX Officer Submits

Fresh officer Riley Tess is sent to produce some..

Added: 2025-03-11 Rating: n/a

The POW

Park Wiley is a strong-willed POW being..

Added: 2025-03-09 Rating: n/a

GayWarGames Poker Face - Part 3 - 1080p

Trussed with leather chains Randy is incapable..

Added: 2025-03-07 Rating: n/a

Nacho Vidal's The Cell

Steamy from the ominous and twisted mind of..

Added: 2025-03-02 Rating: n/a

Hunter Marx with Leo Forte and Jayden Grey - Inmates - Scene 2

In the showers, shaved-headed prisoner Leo Forte..

Added: 2025-02-23 Rating: n/a

BoyNapped Str8 Boy Harry Uses Mitch - Part 3

Hetero jock boy Harry is eventually ready to..

Added: 2025-02-22 Rating: n/a

Straight Hate-Monger Gets His Ass

Max Cameron has just concluded painting hetero..

Added: 2025-02-21 Rating: n/a

Wild Cop and The Hook-up Offender

Romp offender Caleb Colton is locked up in..

Added: 2025-02-21 Rating: n/a

Muscle fellow Cliff Jensen lays claim to prison bi-atch Tony Orlando

C.O. Sebastian Keys spurts off new met inmate..

Added: 2025-02-16 Rating: n/a

Gay-for-pay Hate-Monger Gets His Backside

Max Cameron has just completed painting..

Added: 2025-02-15 Rating: n/a

Mischievous Cop and The Hump Offender

Intercourse offender Caleb Colton is locked up..

Added: 2025-02-10 Rating: n/a

Naughty Cop and The Sex Offender - Jeremy Stevens ,Caleb Colton

Orgy offender Caleb Colton is locked up in..

Added: 2025-02-08 Rating: n/a

Nacho Vidal's The Box

Red-hot from the ominous and twisted mind of..

Added: 2025-02-04 Rating: n/a

CMNM Exploited captive part 1

Judge Drinks has seen dudes like Robert enter..

Added: 2025-02-03 Rating: n/a

Nacho Vidal's The Box

Super-fucking-hot from the evil and distorted..

Added: 2025-02-03 Rating: n/a

The Pow

Park Wiley is a strong-willed POW being limited..

Added: 2025-02-03 Rating: n/a

RusCapturedBoys - Trap for Ran away Captives Ten

When we torment our caught fugitives we do not..

Added: 2025-02-01 Rating: n/a

Locked Up

During an strenuous firefight battle, Dollar..

Added: 2025-02-01 Rating: n/a

Dragon Media - Jail Cherries

Prison Cherries features almost 2 hours of..

Added: 2025-01-31 Rating: n/a

Suite703 Studs Stiff At Work - Jake Steel & Scott Campbell (Nicoli)

What nicer way to pass the time in prison than a..

Added: 2025-01-29 Rating: n/a

Nasty Crank Takes Some Raunchy Justice

Creepy voyeur Griffin is harshly dragged into..

Added: 2025-01-27 Rating: n/a

Deceptive Detainee

All hell violates liberate when deceptive..

Added: 2025-01-27 Rating: n/a

MilitaryClassified - Montana2 - Anal invasion

Everyone is conversing about Montana and his..

Added: 2025-01-25 Rating: 100%

YoungPerps - Hardened Criminal

Apollo is a troublemaker, but his antics come to..

Added: 2025-01-24 Rating: n/a

Caught Off Guard: Dante Colle Pulverizes Jail Guard, Derek Kage

New-comer jail guard Derek Kage is already bored..

Added: 2025-01-24 Rating: n/a

Deceptive Detainee

All hell cracks liberate when deceptive detainee..

Added: 2025-01-24 Rating: n/a

Gay-for-pay Hate-Monger Gets His Bum

Max Cameron has just completed painting..

Added: 2025-01-22 Rating: n/a

Trussed Jail Part 3: Paying The Piper

Officer Michael DelRay waits eagerly in an open,..

Added: 2025-01-20 Rating: n/a

Categories

Disclaimer: All models on this adult site are 18 years or older. Our site has a zero-tolerance policy against illegal pornography. All videos and links are provided by 3rd parties. We have no control over the content of these pages. We take no responsibility for the content on any website which we link to, please use your own discretion while surfing the porn links. This website uses cookies to ensure you get the best experience on our website.

© Gay.FilesMonster.TV • DMCA Policy • Privacy Statement •