Inmate

Pages: NEXT ►

Order by: Popular Date Relevance

Supreme Cop - Bad Cop

Officer Abel Archer is doing his rounds, when he..

Added: 2025-02-07 Rating: n/a

Lockup, Box Extraction & Jail Fuckfest - Part Two

The officers of the jail line their booties up..

Added: 2025-02-06 Rating: n/a

BoundGods Lieutenant Wilde's Extraordinary Justice

Lieutenant Religious Wilde loyal this whole week..

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

Jeremy Spreadums: Fresh CO gets wanked by 2 insatiable inmates

Gorgeous corrections officer Jeremy Spreadums..

Added: 2025-01-25 Rating: n/a

Suite703 Studs Hard At Work - Ari Silvio, Trevor Knight & Tucker Scott

Ari is going to pay his debt to society by..

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

Fresh muscled inmate at the grace of Officer Connor Maguire

Seth Santoro waits in his jail cell as Officer..

Added: 2025-01-18 Rating: n/a

Officer DelRay has his Prisoners on Edge

Roped Jail Part 2. Formerly newbie Correctional..

Added: 2025-01-18 Rating: n/a

Edging hot, uncircumcised cock in jail

Sebastian has been locked up for yet another..

Added: 2025-01-17 Rating: n/a

Great Cop - Bad Cop

Officer Abel Archer is doing his rounds, when he..

Added: 2025-01-17 Rating: n/a

Fine Behavior: Inmate Joseph Ox Submits to Officer Micah Martinez

Inmate Joseph Ox is performing his supervised..

Added: 2025-01-17 Rating: n/a

Gang Pulverize Games 720p

An inmate is pleading a youthfull crud for..

Added: 2025-01-13 Rating: n/a

Master Peter's Jail Orgy

A dorm search from Tormentor Peter shortly has..

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

Lockup, Box Extraction & Jail Bang-out - Part 2

The officers of the jail line their butts up as..

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

Hairy weirdo gets taken downtown & group humped by the entire jail mansion

Brandon Atkins is a wild weirdo up to no good,..

Added: 2024-12-31 Rating: n/a

Edging hot, uncut bone in jail

Sebastian has been locked up for yet another..

Added: 2024-12-27 Rating: n/a

Prison Break

Officer Johnny Donovan is overpowered by inmate,..

Added: 2024-12-24 Rating: n/a

Fresh Boy Tony Orlando Stamina Kittling and Teased to Rapture

New encountered and stuttering, scanty inmate..

Added: 2024-12-24 Rating: n/a

Lockup, Box Extraction & Prison Fuck-fest - Part 2

The officers of the jail line their backsides up..

Added: 2024-12-21 Rating: n/a

Fur covered pervert gets taken downtown & group boned by the whole prison building

Brandon Atkins is a naughty weirdo up to no..

Added: 2024-12-20 Rating: n/a

New meat inmate for Officer Maguire

Deep inwards Kink Prison, Officer Maguire brings..

Added: 2024-12-18 Rating: n/a

Fresh bulky inmate at the mercy of Officer Connor Maguire

Seth Santoro waits in his jail cage as Officer..

Added: 2024-12-17 Rating: n/a

Fresh Boy Tony Orlando Stamina Kittling and Taunted to Rapture

Fresh encountered and stuttering, scanty inmate..

Added: 2024-12-16 Rating: n/a

Superb Cop - Bad Cop

Officer Abel Archer is doing his rounds, when he..

Added: 2024-12-16 Rating: n/a

Edging hot, uncircumcised salami in jail

Sebastian has been locked up for yet another..

Added: 2024-12-15 Rating: n/a

Muscle boy Cliff Jensen lays claim to jail tart Tony Orlando

C.O. Sebastian Keys droplets off fresh faced..

Added: 2024-12-14 Rating: n/a

Officer DelRay has his Prisoners on Brink

Precedingly new-comer Correctional Officer..

Added: 2024-12-14 Rating: n/a

Prison Break

Officer Johnny Donovan is overcame by inmate,..

Added: 2024-12-14 Rating: n/a

Bad guy inmate Cliff Jensen violates in fresh guard Michael DelRay

It´s a noiseless day on the box block and bad..

Added: 2024-12-12 Rating: n/a

Lieutenant Wilde's Extraordinary Justice

Lieutenant Christian Wilde devoted this whole..

Added: 2024-12-12 Rating: n/a

Inmate Joseph Ox Submits to Officer Micah Martinez

Inmate Joseph Ox is performing his supervised..

Added: 2024-12-09 Rating: n/a

Fresh muscled inmate at the mercy of Officer Connor Maguire

Seth Santoro waits in his jail cage as Officer..

Added: 2024-12-04 Rating: n/a

Fresh meat inmate for Officer Maguire

Deep inwards Kink Prison, Officer Maguire brings..

Added: 2024-12-03 Rating: n/a

Ace In The Hole, Episode 1

It's Ace Stallion's first-ever day in jail and..

Added: 2024-12-03 Rating: n/a

Good Cop - Bad Cop

Officer Abel Archer is doing his rounds, when he..

Added: 2024-11-30 Rating: n/a

Kinkmen - Lieutenant Wilde's Extraordinary Justice

Lieutenant Christian Wilde devoted this entire..

Added: 2024-11-28 Rating: n/a

Bad boy inmate Cliff Jensen cracks in fresh guard Michael DelRay

It´s a tranquil day on the cell block and bad..

Added: 2024-11-28 Rating: n/a

Muscle boy Cliff Jensen lays claim to jail whore Tony Orlando

C.O. Sebastian Keys drops off fresh met inmate..

Added: 2024-11-28 Rating: n/a

Kinkmen - Inmate Joseph Ox Submits to Officer Micah Martinez

Inmate Joseph Ox is performing his supervised..

Added: 2024-11-20 Rating: n/a

Lockup, Cell Extraction & Jail Sex - Part 2

The officers of the prison line their asses up..

Added: 2024-11-18 Rating: n/a

Muscle guy Cliff Jensen lays claim to prison cockslut Tony Orlando

C.O. Sebastian Keys droplets off fresh faced..

Added: 2024-11-17 Rating: n/a

NakedSword x Master Peter - Master Peter's Jail Romp

A dorm search from Tormentor Peter soon has the..

Added: 2024-11-12 Rating: n/a

Naked Conviction

Locked in with super-fucking-hot and kinky..

Added: 2024-11-02 Rating: n/a

Ace In The Hole, Gig 1

It's Ace Stallion's first day in jail and almost..

Added: 2024-10-27 Rating: n/a

Muscle stud Cliff Jensen lays claim to jail bitch Tony Orlando

C.O. Sebastian Keys spurts off fresh faced..

Added: 2024-10-16 Rating: n/a

Favo & Raised

Joel says he'll chill out if Cole deep throats..

Added: 2024-10-11 Rating: n/a

Inmate With A Massive Shaft

Perverse fucky-fucky games with fresh inmate..

Added: 2024-10-02 Rating: n/a

Inmate With A Good-sized Fuckpole

Perverse sex games with fresh inmate Luke...

Added: 2024-10-01 Rating: n/a

Bad boy inmate Cliff Jensen intrudes new guard DelRay

BOUND Jail Part 1: It’s a peaceful day on the..

Added: 2024-09-27 Rating: n/a

Jail Camp- Poked Into Subjugation

A jail camp cut off from all shape of..

Added: 2024-09-27 Rating: n/a

Trussed Jail Pt 2: Officer DelRay has his Prisoners on Brim

Formerly novice Correctional Officer Michael..

Added: 2024-09-23 Rating: n/a

Jeremy Stevens: Lockup, Cage Extraction & Jail Gang Plumb

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

Added: 2024-09-20 Rating: n/a

Superb Cop - Bad Cop

Officer Abel Archer is doing his rounds, when he..

Added: 2024-09-17 Rating: n/a

Trussed Jail Pt 2: Officer DelRay has his Prisoners on Brink

Formerly new-cummer Correctional Officer Michael..

Added: 2024-09-11 Rating: n/a

Prison Break

Officer Johnny Donovan is overpowered by inmate,..

Added: 2024-09-11 Rating: n/a

Sans a condom fuckfests with lippy criminals

From the showers to the warden’s office, no..

Added: 2024-09-08 Rating: n/a

Eurocreme - My Dearest Inmate

Jail guard Gabriel observes his dearest young..

Added: 2024-09-07 Rating: n/a

Good Behavior: Inmate Joseph Ox Submits to Officer Micah Martinez

Inmate Joseph Ox is performing his supervised..

Added: 2024-09-04 Rating: n/a

Slammer

Slammer gives fresh meaning to the term,..

Added: 2024-09-04 Rating: n/a

The Hottest Jail Fuckfests

Slammer gives fresh meaning to the term,..

Added: 2024-08-27 Rating: n/a

Bad boy inmate Cliff Jensen cracks in fresh guard Del Ray

It’s a silent day on the box block and bad..

Added: 2024-08-08 Rating: n/a

Jail Break

Officer Johnny Donovan is overcame by inmate,..

Added: 2024-08-06 Rating: n/a

Prison Break

Officer Johnny Donovan is overcame by inmate,..

Added: 2024-08-02 Rating: n/a

Titch Jones, Anthony Thomas & Rio Francisco

Shower Threesome: With a fresh Top Dog, the..

Added: 2024-08-02 Rating: n/a

Iron Cell

Paul Barresi has a fashion that's unique. He is..

Added: 2024-08-01 Rating: n/a

Excellent Behavior: Inmate Joseph Ox Submits to Officer Micah Martinez

Inmate Joseph Ox is performing his supervised..

Added: 2024-07-30 Rating: n/a

Jeremy Stevens: Lockup, Box Extraction & Jail Group Fuck

In this astounding KinkMen Shoot: The cells are..

Added: 2024-07-30 Rating: n/a

Bound Jail Part 2: Officer DelRay has his Prisoners on Edge

Part 2. Precedingly new-comer Correctional..

Added: 2024-07-28 Rating: n/a

Roped Prison Part 2: Officer DelRay has his Prisoners on Edge

Strapped Jail Part 2. Previously newbie..

Added: 2024-07-25 Rating: n/a

Supreme Cop - Bad Cop

Officer Abel Archer is doing his rounds, when he..

Added: 2024-07-22 Rating: n/a

Bad fellow inmate Cliff Jensen violates in fresh guard

Part 1: It’s a quiet day on the box block and..

Added: 2024-07-13 Rating: n/a

Jeremy Stevens: Lockup, Cell Extraction & Jail Group Plow

In this unbelievable KinkMen Shoot: The cells..

Added: 2024-07-13 Rating: n/a

Lockup, Cage Extraction & Jail Hook-up - Part 2

The officers of the jail line their donks up as..

Added: 2024-07-12 Rating: n/a

KinkMen Prison Break

Officer Johnny Donovan is overcame by inmate,..

Added: 2024-07-10 Rating: n/a

Ace In The Hole, Sequence 1

It's Ace Stallion's first-ever day in jail and..

Added: 2024-07-08 Rating: n/a

Ace In The Hole, Episode 1

It's Ace Stallion's very first day in jail and..

Added: 2024-07-07 Rating: n/a

Ace In The Hole, Sequence 2

When Blaze Austin catches sight of fresh..

Added: 2024-07-07 Rating: n/a

Ace In The Hole, Episode 2

When Blaze Austin spots fresh prisoner Ace..

Added: 2024-07-06 Rating: n/a

Ace In The Hole, Scene 1

It's Ace Stallion's first day in jail and nearly..

Added: 2024-07-05 Rating: n/a

Ace In The Hole, Episode 2

When Blaze Austin catches sight of new prisoner..

Added: 2024-07-04 Rating: n/a

Fresh Man Tony Orlando Stamina Kittling and Taunted to Rapture

Fresh encountered and stuttering, poor inmate..

Added: 2024-07-01 Rating: n/a

Prison Break: Carter Collins, Johnny Donovan & Truck Darkholme 1080p

Officer Johnny Donovan is defeated by inmate,..

Added: 2024-06-26 Rating: n/a

Kink Studs - Studs on Edge - Prison Break

Officer Johnny Donovan is overcame by inmate,..

Added: 2024-06-26 Rating: n/a

Prison Break - Carter Collins, Johnny Donovan, Truck Darkhol

Officer Johnny Donovan is overcame by inmate,..

Added: 2024-06-24 Rating: n/a

Fresh Meat Inmate For Officer Maguire

Deep inwards Kink Prison, Officer Maguire brings..

Added: 2024-06-24 Rating: n/a

MisterMale Predominated by lots of jizz-shotguns in jail

This gay, bearded, virile masculine thought he'd..

Added: 2024-06-06 Rating: n/a

Colt Masterstrokes - Gustavo Franco & Lucas Canigia

Masterstrokes - Homo Softcore Art Brought To..

Added: 2024-05-20 Rating: n/a

Subordination Prison, Gig #04

Officer Drew Sebastian can't get enough of..

Added: 2024-04-30 Rating: n/a

Bad man inmate Cliff Jensen violates

It’s a noiseless day on the cell block and bad..

Added: 2024-04-21 Rating: n/a

Corded Prison: Bad dude inmate Cliff Jensen cracks in fresh guard DelRay

Part 1: It’s a calm day on the cage block and..

Added: 2024-04-08 Rating: n/a

Muscle man Cliff Jensen lays claim to jail bitch Tony Orlando

C.O. Sebastian Keys droplets off fresh faced..

Added: 2024-04-07 Rating: n/a

Naked conviction

Locked in with super-steamy and naughty youthful..

Added: 2024-04-05 Rating: n/a

Bad dude inmate Cliff Jensen cracks in fresh guard DelRay

Part 1: It’s a tranquil day on the cage block..

Added: 2024-04-04 Rating: n/a

Scottxxx - Banged Up

In this super hot sequence from Scottxxx,..

Added: 2024-02-28 Rating: n/a

Jail Joeng Turns his cellmate into his feet, rod and ass cockslut and completly

I made the error of staying behind and the..

Added: 2024-01-25 Rating: n/a

Dominate penetrating at the detention center

Incarcerated at the detention center for..

Added: 2023-11-11 Rating: n/a

Slot Patrol

"Out of your camper and down on your knees boy!..

Added: 2023-10-25 Rating: n/a

Inmates no locker

"Felipe Leonel and Erivaldo Ribeiro are in a..

Added: 2023-07-06 Rating: n/a

Prison Camp Fucked Into Conformity

A pri camp cut off from all shape of..

Added: 2023-05-16 Rating: n/a

Axel Kane, Ceasar Camaro, Johnny V., Landon Matthews

Things have gotten pretty active in here. This..

Added: 2023-03-31 Rating: 0%

44 Jail Wc Hellions

The borstal inmates are lined up outside the..

Added: 2023-02-19 Rating: n/a

Making The Guards Glad

Things have gotten pretty engaged in here. This..

Added: 2023-02-17 Rating: n/a

Queer - Nude Conviction

Locked in with steaming and ultra-kinky..

Added: 2023-02-14 Rating: 100%

Rubbish Pick-Up Ass Fuck Realm Trip

Picking up litter is something that most inmates..

Added: 2023-02-13 Rating: n/a

Fetish Collection: Bawdy Encounters

Tony Buff is the fellow in charge and he and his..

Added: 2023-02-01 Rating: n/a

Contraband Cock Check

Life in here isn’t always easy. We must..

Added: 2022-12-14 Rating: n/a

Ferocious Tops - Jail Toilets Hellions

The borstal inmates are lined up outside the..

Added: 2022-11-17 Rating: 100%

Lockdown

Wee to Pine Hearst, a maximum-security pri...

Added: 2022-11-01 Rating: n/a

Jail Bangers

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

Added: 2022-10-24 Rating: n/a

Prison Blues

Ten Eighteen -21 year olds in a youthful..

Added: 2022-10-24 Rating: n/a

Bare Conviction

Locked in with red-hot and horny youthfull..

Added: 2022-08-10 Rating: n/a

Subjugation Prison, Gig #04 (Drew Sebastian, Devin Franco)

Officer Drew Sebastian can't get enough of..

Added: 2022-07-07 Rating: n/a

Russian Jail - Mega Dudes

The guards of this Russian jail are strict,..

Added: 2022-04-30 Rating: n/a

Jail Camp - Plowed Into Submission

A prison camp cut off from all shape of..

Added: 2022-04-18 Rating: n/a

Lengthy Forearm Of The Law Part 1

The cops in charge of this off the hook holding..

Added: 2022-04-10 Rating: n/a

Jail Camp - Buttfuck Onslaught

In this Prison Camp youthful inmates are at the..

Added: 2022-04-07 Rating: n/a

Catalina - Powertool (1986)

Buttplug into this high torque tale of riveting..

Added: 2022-03-24 Rating: n/a

Prison Rest room Hooligans

The borstal inmates are lined up outside the..

Added: 2022-03-04 Rating: n/a

Jail Camp - Boinked Into Subordination

A prison camp cut off from all shape of..

Added: 2022-03-03 Rating: n/a

Garbage Pick-Up Ass Fuck Field Trip - Dante Drackis, Leo Silva

Picking up litter is something that most inmates..

Added: 2022-03-03 Rating: n/a

Jail Camp Screwed Into Obedience

A pri camp cut off from all shape of..

Added: 2022-02-04 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 •