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Prison Passions: Paddy O Breaks Guard Caio Prison Passions: Paddy O Breaks Guard Caio Paddy O'BrianCaio Rodrigues BY: MEN.com Dec 01, 2025 4.8k 58%
Prison Privileges are Hard To Cum By! Prison Privileges are Hard To Cum By! Armando de ArmasRiley Mitchel BY: MenOver30 Jul 10, 2021 2.6k 67%
Prison Guard Rikk Worshiped Prison Guard Rikk Worshiped Rikk York BY: MyFriendsFeet.com Oct 13, 2020 4.6k 33%
Prison-boy takes every raw inch that his buff guard has to offer! HD Prison-boy takes every raw inch that his buff guard has to offer! HD Rudy Black BY: Staxus Nov 20, 2019 5k 0%
Prisoner Of War, Scene #04 Prisoner Of War, Scene #04 Brandon WildeRob Yaeger BY: Icon Male Oct 21, 2019 9.2k 79%
Prison Shower (Rafael Alencar and Johnny Rapid ) Prison Shower (Rafael Alencar and Johnny Rapid ) Rafael AlencarJohnny Rapid BY: MEN.com Oct 10, 2019 135.7k 75%
Prison Shower 3 Prison Shower 3 Jimmy JohnsonJohnny RapidColby JansenCharlie Harding BY: MEN.com Oct 10, 2019 44.1k 59%
Prison Shower 2 (Johnny Rapid, Sebastian Young & Jack King) Prison Shower 2 (Johnny Rapid, Sebastian Young & Jack King) Jack KingSebastian YoungJohnny Rapid BY: MEN.com Oct 10, 2019 50.8k 87%
Prison Shower 4 (Cooper Reed, Johnny Rapid & Landon Conrad) Prison Shower 4 (Cooper Reed, Johnny Rapid & Landon Conrad) Landon TerryJohnny RapidCooper Reed BY: MEN.com Oct 10, 2019 29.3k 53%
Prison Bitch Ain't So Tough! (Bareback) Prison Bitch Ain't So Tough! (Bareback) Mark YatesClay BY: Boys Halfway House Oct 09, 2019 10.5k 64%
Rise Of The Prison Bitch Part 3 Rise Of The Prison Bitch Part 3 Jake PrestonBruce JonesJoel Hart BY: MEN.com Oct 11, 2024 13.1k 36%
Rise Of The Prison Bitch Part 2 Rise Of The Prison Bitch Part 2 Cole ConnorJoel Hart BY: MEN.com Oct 06, 2024 8k 28%
Rise Of The Prison Bitch Part 1 Rise Of The Prison Bitch Part 1 Jake PrestonBrody Meyer BY: MEN.com Sep 30, 2024 13.2k 46%
Finding His Prison Bitch Finding His Prison Bitch Enzo MüllerChuck Conrad BY: MEN.com Dec 12, 2023 12.8k 52%
Valdemar Santana Fucks The Prison Guard Valdemar Santana Fucks The Prison Guard Valdemar Santana BY: Raw Fuck Club Nov 25, 2023 2.9k 0%
Big-Dicked Prison Buddy Big-Dicked Prison Buddy Joe ParkerJohnny Hunter BY: Extra Big Dicks Nov 12, 2020 2.9k 100%
Submission Prison Submission Prison Drew SebastianDevin Franco BY: Fisting Central Mar 13, 2020 5.6k 100%
Submission Prison, Scene 3 Submission Prison, Scene 3 Drew SebastianDevin Franco BY: Fisting Central Feb 04, 2020 5.3k 100%
Submission Prison Submission Prison Nate GrimesMyles LandonDrew Dixon BY: Fisting Central Jan 27, 2020 4.8k 86%
Submission Prison, Scene #01 Submission Prison, Scene #01 Nate GrimesMyles LandonDrew Dixon BY: Fisting Central Jan 02, 2020 5.4k 80%
Double-Penetration Cowboy-Style Ride For Prison Bitch Kevin Ateah! HD Double-Penetration Cowboy-Style Ride For Prison Bitch Kevin Ateah! HD BY: Staxus Nov 20, 2019 8k 100%
Meathead Muscle Man Brad Ranger FUCKS Savannah Camon Like He's Fresh Out Of Prison Meathead Muscle Man Brad Ranger FUCKS Savannah Camon Like He's Fresh Out Of Prison Brad Ranger BY: Hot Guys Fuck Oct 14, 2019 2.1k 0%
Barebacked in Prison (Sebastian Young, Eli Hunter, Zane Anders, Donny Forza & Rocko South) (Part 4) Barebacked in Prison (Sebastian Young, Eli Hunter, Zane Anders, Donny Forza & Rocko South) (Part 4) Eli HunterSebastian YoungZane AndersDonny Forza BY: Bromo Oct 09, 2019 11.5k 89%
Barebacked in Prison (Sebastian Young Fucks Rocko South) (Part 3) Barebacked in Prison (Sebastian Young Fucks Rocko South) (Part 3) Sebastian Young BY: Bromo Oct 09, 2019 8.8k 93%
A Guide To Sex In Prison (Tony Paradise Fucks Dimitri Kane) (Part 3) A Guide To Sex In Prison (Tony Paradise Fucks Dimitri Kane) (Part 3) Tony ParadiseDimitri Kane BY: MEN.com Oct 09, 2019 9.5k 93%
A Guide To Sex In Prison (Adam Bryant Fucks Josh Peters) (Part 2) A Guide To Sex In Prison (Adam Bryant Fucks Josh Peters) (Part 2) Josh PetersAdam Bryant BY: MEN.com Oct 09, 2019 13.2k 58%
A Guide To Sex In Prison (Sebastian Young Flip-Fucks With Landon Mycles) (Part 1) A Guide To Sex In Prison (Sebastian Young Flip-Fucks With Landon Mycles) (Part 1) Marcus MojoSebastian Young BY: MEN.com Oct 09, 2019 13.6k 70%
Tatted hung aryan prison thug breed fat bitch Tatted hung aryan prison thug breed fat bitch BY: evilpiercer Oct 01, 2018 1.6k 100%
2 tatted prison tops breed horny bitch 2 tatted prison tops breed horny bitch BY: crispyslayer Jun 21, 2017 2.2k 100%
Luis Blava - Bareback sex in Prison Luis Blava - Bareback sex in Prison BY: East Boys Jan 27, 2020 1.1k 0%
RIDE Or DIE: Slippery When Wet RIDE Or DIE: Slippery When Wet Drew SebastianAlpha Wolfe BY: Falcon Studios Mar 23, 2026 1.5k 100%
RIDE Or DIE: The Gang's All Here RIDE Or DIE: The Gang's All Here Bennett AnthonyChris DamnedAlpha WolfeReignDrew Valentino BY: Falcon Studios Mar 16, 2026 1.8k 50%
Deep Dreams, Part 1 Deep Dreams, Part 1 Killian KnoxJosh Cannon BY: Family Creep Dec 24, 2023 3.1k 100%
Dickdown In Lockdown Dickdown In Lockdown Leo BacchusChuck Conrad BY: MEN.com Oct 17, 2023 12.2k 32%
Where's My Phone Call Where's My Phone Call Roman ToddMasyn Thorne BY: Next Door Studios Oct 05, 2023 6.1k 57%
Creampied Cuties: Compilation Creampied Cuties: Compilation Hans BerlinJustin MatthewsMax SargentCarter WoodsLeeroy JonesJesse StoneLiam SkyeAndrew MillerLucca MazziGrant DucatiDerek KageBrody FoxColton Scott BY: ASG Max Sep 04, 2023 8.8k 53%