Jail Videos - Gay (1,178)

Forty Plus Stud 3

HD 0:30 / 1:22:00

Forty Plus Stud 3

AEBN 17 years ago

PRISON BITCH FOR BIG BLACK COCK

63% 4K 0:30 / 16:01

PRISON BITCH FOR BIG BLACK COCK

Clips4sale 6 months ago

Young Bastards 7: Prison Camp Fucked Into Submission

53% HD 0:30 / 1:30:00

Young Bastards 7: Prison Camp Fucked Into Submission

AEBN 6 years ago

Prison Camp - fucked into acceptance

66% HD 1:20 / 1:30:34

Prison Camp - fucked into acceptance

GayNetwork 9 years ago

Jimmy's Punishment

47% 0:11 / 1:13:40

Jimmy's Punishment

Clips4sale 2 years ago

Gaylocked (SD MP4)

4K 0:30 / 16:12

Gaylocked (SD MP4)

Clips4sale 3 months ago

Gaylocked (4KUHD MP4)

65% HD 0:30 / 16:12

Gaylocked (4KUHD MP4)

Clips4sale 3 months ago

Prisoner Of War 2

HD 0:30 / 1:31:00

Prisoner Of War 2

AEBN 9 years ago

Prison Sex

HD 0:30 / 1:31:00

AEBN 12 years ago

Submission Prison

55% HD 0:30 / 1:03:00

Submission Prison

AEBN 5 years ago

PRISON BITCH

65% HD 0:10 / 14:23

LoyalFans 2 weeks ago

Ride Or Die: Hard Time - Director's Cut

63% HD 0:30 / 1:47:00

Ride Or Die: Hard Time - Director's Cut

AEBN 2 years ago

Boys Behind Bars 3: Naked Justice

61% HD 0:30 / 1:43:00

Boys Behind Bars 3: Naked Justice

AEBN 20 years ago

Sentenced 2: Punished

49% HD 0:30 / 1:51:00

Sentenced 2: Punished

AEBN 10 years ago

Trapped in Prison - Part One

35% HD 0:25 / 27:32

Trapped in Prison - Part One

Clips4sale 10 months ago

The Hard Way Part 2

HD 0:30 / 28:00

The Hard Way Part 2

AEBN 15 years ago

Powertool 2: Breaking Out

71% HD 0:30 / 1:26:00

Powertool 2: Breaking Out

AEBN 16 years ago

Long Arm Of The Law

HD 0:30 / 1:28:00

Long Arm Of The Law

AEBN 11 years ago

Straight guy used by group of gay men

HD 0:41 / 12:36

Straight guy used by group of gay men

DarkCruising 4 years ago

First Time Around

51% HD 0:30 / 1:28:00

First Time Around

AEBN 18 years ago

Rodney Steele Picks Up A Hitchhiker

41% HD 3:32 / 1:30:00

Rodney Steele Picks Up A Hitchhiker

AEBN 8 years ago

Drill My Hole 8

HD 0:30 / 1:48:00

Drill My Hole 8

AEBN 8 years ago

Code Of Conduct 2: Deliverance

HD 0:30 / 1:22:00

Code Of Conduct 2: Deliverance

AEBN 14 years ago

Sentenced 2: Punished

HD 0:30 / 1:51:00

Sentenced 2: Punished

AEBN 10 years ago

My First Time Avoiding Jail

HD 0:30 / 1:41:00

My First Time Avoiding Jail

AEBN 1 year ago

Dark Deep Fucks

HD 0:30 / 2:04:00

Dark Deep Fucks

AEBN 11 years ago

Feminization project prison pussy

38% HD 0:30 / 7:29

Feminization project prison pussy

Clips4sale 9 months ago

Dungeon Caged Slave Used and Owned

49% HD 3:39 / 1:44:00

Dungeon Caged Slave Used and Owned

AEBN 15 years ago

Criminal Behavior In Cell Block 6

59% HD 0:30 / 1:27:00

Criminal Behavior In Cell Block 6

AEBN 14 years ago

Unleash The Beast

HD 0:30 / 1:35:00

Unleash The Beast

AEBN 14 years ago

Prison Doctor Treats a Painful Groin

72% HD 3:04 / 2:07:00

Prison Doctor Treats a Painful Groin

AEBN 10 years ago

Hapless Teen Fucked And Seeded

43% HD 0:30 / 29:45

Hapless Teen Fucked And Seeded

Clips4sale 6 months ago

My Big Fucking Dick: Shane Rollins

63% HD 0:30 / 2:44:00

My Big Fucking Dick: Shane Rollins

AEBN 7 years ago

Unleash The Beast

HD 0:30 / 1:35:00

Unleash The Beast

AEBN 14 years ago

Secret Sex 3: The Takeover

HD 0:30 / 1:07:00

Secret Sex 3: The Takeover

AEBN 16 years ago

Airport Security 24

44% HD 0:30 / 1:04:00

Airport Security 24

AEBN 7 years ago

A Guide To Sex In Prison

61% HD 0:30 / 1:23:00

A Guide To Sex In Prison

AEBN 8 years ago

Obsessed with this delinquent's ass

40% HD 3:20 / 18:45

Obsessed with this delinquent's ass

HotCast 1 year ago

Giant humiliation VORE | Hanging by a thread - Lalo Cortez

50% 4K 0:30 / 7:32

Giant humiliation VORE | Hanging by a thread - Lalo Cortez

Clips4sale 2 years ago

Officer Daddy

57% HD 0:30 / 1:17:00

AEBN 9 years ago

Prison Fuck with Fox Rifler

Prison Fuck with Fox Rifler

Clips4sale 6 days ago

Lawless

66% HD 0:30 / 1:54:00

AEBN 14 years ago

Cholo Lovers

70% HD 0:30 / 2:15:00

AEBN 11 years ago

L'Elisir D'Amore

HD 0:30 / 1:47:00

L'Elisir D'Amore

AEBN 7 years ago

BOUND 2 SERVE

63% 0:58 / 1:12:45

Clips4sale 3 years ago

Joe Gage Sex Files 22: Diary Of A Prison Doctor

55% HD 0:30 / 1:52:00

Joe Gage Sex Files 22: Diary Of A Prison Doctor

AEBN 7 years ago

SPIT AND PISS COVERED

48% HD 3:41 / 15:04

SPIT AND PISS COVERED

DarkCruising 1 year ago

Inter-Racial Interrogation

HD 0:30 / 1:13:00

Inter-Racial Interrogation

AEBN 15 years ago

Prison Break

68% HD 0:51 / 39:35

DarkCruising 2 years ago

Duncan & Will; Prisoners of The Tickler (Final Part)

55% 0:11 / 10:02

Duncan & Will; Prisoners of The Tickler (Final Part)

Clips4sale 1 year ago

Straight As They Cum

HD 0:30 / 1:39:00

Straight As They Cum

AEBN 12 years ago

Raw Piss Prison

HD 0:30 / 2:01:00

Raw Piss Prison

AEBN 15 years ago

Prison Fuck with Excel Hung

55% 0:30 / 17:43

Prison Fuck with Excel Hung

Clips4sale 2 weeks ago

Fresh Meat Inmate for Officer Maguire

49% 0:11 / 44:09

Fresh Meat Inmate for Officer Maguire

Clips4sale 1 year ago

He Drinks Piss In Jail

49% HD 3:00 / 9:00

He Drinks Piss In Jail

AEBN 2 months ago

Enhanced Interrogation: Detained Stud Faces a Horny, Sadistic Agent

64% 0:30 / 49:19

Enhanced Interrogation: Detained Stud Faces a Horny, Sadistic Agent

Clips4sale 1 year ago

SPIT AND PISS COVERED

47% HD 3:41 / 15:04

SPIT AND PISS COVERED

CazzoFilm 1 year ago

Prisoner Of War

61% HD 0:30 / 1:34:00

Prisoner Of War

AEBN 8 years ago

Black Brigade

66% HD 0:30 / 1:20:00

AEBN 12 years ago

young straight inmate is fed with dick while handcuffed

HD 0:30 / 20:10

young straight inmate is fed with dick while handcuffed

Clips4sale 1 year ago

Prisoner Of War

HD 0:30 / 1:34:00

Prisoner Of War

AEBN 8 years ago

TIny explores giant police officer - Lalo Cortez

TIny explores giant police officer - Lalo Cortez

Clips4sale 1 year ago

Mind the Gap; Mummified Orgasm of the Tape Bound Twink

66% 0:30 / 16:05

Mind the Gap; Mummified Orgasm of the Tape Bound Twink

Clips4sale 9 months ago

Decisions Are Based On Value

49% HD 0:30 / 23:59

Decisions Are Based On Value

Clips4sale 7 months ago

Dominated Plus Degraded

HD 0:30 / 1:19:00

Dominated Plus Degraded

AEBN 2 years ago

Prison Fuck with Tony Genius

65% 0:30 / 29:39

Prison Fuck with Tony Genius

Clips4sale 2 weeks ago

Prison Fuck with Hairy Otter

Prison Fuck with Hairy Otter

Clips4sale 2 weeks ago

TRAINING MY SLAVE

65% 0:55 / 1:02:50

TRAINING MY SLAVE

Clips4sale 3 years ago

Muscle Stud Uses Human Weights- Bax and Frank Fun Size

68% 0:30 / 11:20

Muscle Stud Uses Human Weights- Bax and Frank Fun Size

Clips4sale 4 months ago

Man Cif lifer handcuffed Arrest in Jail

63% HD 0:11 / 3:13

Man Cif lifer handcuffed Arrest in Jail

Clips4sale 3 years ago

Shrunk and mindfucked straight to gay for giants pleasure - Lalo Cortez

HD 0:24 / 14:39

Shrunk and mindfucked straight to gay for giants pleasure - Lalo Cortez

Clips4sale 4 months ago

New Muscled Inmate at the Mercy of Officer Connor Maguire

New Muscled Inmate at the Mercy of Officer Connor Maguire

Clips4sale 1 year ago

Officer Maguire Beats and Fucks a Stud for Littering

Officer Maguire Beats and Fucks a Stud for Littering

Clips4sale 1 year ago

Carlos Baxter And Shane Rage

HD 0:30 / 2:04:00

Carlos Baxter And Shane Rage

AEBN 18 years ago

Ride Or Die: The Gangs All Here - Director's Cut

47% HD 0:30 / 23:00

Ride Or Die: The Gangs All Here - Director's Cut

AEBN 3 years ago

Destroy Your Ass For Inmates - Anal Masturbation Instructions From Prison

47% HD 0:10 / 32:16

Destroy Your Ass For Inmates - Anal Masturbation Instructions From Prison

LoyalFans 8 months ago

Winter is Cumming - Hard!

Winter is Cumming - Hard!

Clips4sale 4 weeks ago

Prison Bitch Cellblock 13

56% HD 0:30 / 1:25:00

Prison Bitch Cellblock 13

AEBN 8 years ago

From law to labor | Mpreg labor - Lalo Cortez

65% HD 0:17 / 10:58

From law to labor | Mpreg labor - Lalo Cortez

Clips4sale 1 year ago

Luke - The Thief *Old Content*

Luke - The Thief *Old Content*

Clips4sale 10 months ago

Lyle Boyce Is Ass Banged by a Prison Guard

71% HD 3:42 / 1:17:00

Lyle Boyce Is Ass Banged by a Prison Guard

AEBN 9 years ago

* 854x480p * Sissy Closet Queer Caught Thieving Pantyhose - Mp4

53% 0:09 / 14:20

* 854x480p * Sissy Closet Queer Caught Thieving Pantyhose - Mp4

Clips4sale 10 months ago

Prisoner - Part 2 (720p) Gay Bondage - Male Domination - Gay Armipts - Gay Domination - Handcuffs - Spanking

50% HD 0:30 / 12:45

Prisoner - Part 2 (720p) Gay Bondage - Male Domination - Gay Armipts - Gay Domination - Handcuffs - Spanking

Clips4sale 4 weeks ago

Prisoner - Part 1 (720p) Gay Bondage - Male Domination - Gay Armipts - Gay Domination - Handcuffs - Spanking

HD 0:30 / 13:09

Prisoner - Part 1 (720p) Gay Bondage - Male Domination - Gay Armipts - Gay Domination - Handcuffs - Spanking

Clips4sale 4 weeks ago

Correctional Officer Tied Up and Fucked by an Inmate

57% HD 0:30 / 43:00

Correctional Officer Tied Up and Fucked by an Inmate

AEBN 6 years ago

Correctional Officer Tied Up and Fucked by an Inmate

52% HD 0:30 / 43:00

Correctional Officer Tied Up and Fucked by an Inmate

AEBN 6 years ago

PRISON SISSY PANTY BITCH

66% 4K 0:38 / 11:29

PRISON SISSY PANTY BITCH

Clips4sale 6 months ago

Interrogation On Cell Block B Part 2 (720p)

66% HD 0:30 / 13:36

Interrogation On Cell Block B Part 2 (720p)

Clips4sale 1 month ago

Drive It Deeper

45% HD 0:30 / 1:05:00

Drive It Deeper

AEBN 17 years ago

Prison Fuck with Dallas Steele

66% 0:30 / 20:45

Prison Fuck with Dallas Steele

Clips4sale 2 weeks ago

Nasty Cop and The Sex Offender

Nasty Cop and The Sex Offender

Clips4sale 1 year ago

Prison Shower

57% HD 0:30 / 1:34:00

AEBN 8 years ago

Spartacus

56% HD 0:30 / 2:03:00

AEBN 17 years ago

College Bound

56% HD 0:11 / 1:40:31

Clips4sale 2 years ago

Hot Uncut Sailor Is Tied Up and Edged During Fleet Week!

55% 0:11 / 31:12

Hot Uncut Sailor Is Tied Up and Edged During Fleet Week!

Clips4sale 1 year ago

Breaking and Entering

Breaking and Entering

Clips4sale 2 years ago

Bound Gods: Tyler And Vince

HD 0:30 / 58:00

Bound Gods: Tyler And Vince

AEBN 12 years ago

Airport Security 14

55% HD 0:30 / 1:13:00

Airport Security 14

AEBN 9 years ago

Joe Gage Sex Files 22 - 24

HD 0:30 / 4:00:00+

Joe Gage Sex Files 22 - 24

AEBN 2 months ago

Sex Inferno

HD 0:30 / 1:17:00

AEBN 12 years ago

Guard Makes Inmates Put on Sex Show

63% HD 3:35 / 1:54:00

Guard Makes Inmates Put on Sex Show

AEBN 8 years ago

In The Prison Of Huge Cocks

61% HD 3:39 / 1:17:00

In The Prison Of Huge Cocks

AEBN 8 years ago

Edging Hot, Uncut Cock in Prison

47% 0:11 / 36:25

Edging Hot, Uncut Cock in Prison

Clips4sale 1 year ago

Duty Bound 46

HD 0:30 / 59:00

AEBN 8 years ago

Stiff Sentence

HD 0:30 / 1:47:00

AEBN 8 years ago

The Mountain Prison 4

55% HD 0:30 / 8:00

The Mountain Prison 4

AEBN 2 months ago

Prisoner Of War

63% HD 0:30 / 1:34:00

Prisoner Of War

AEBN 8 years ago

Giant police officer makes you suck his massive cock - Lalo Cortez

54% 4K 0:29 / 6:52

Giant police officer makes you suck his massive cock - Lalo Cortez

Clips4sale 2 years ago

Correctional Officer Tied Up and Fucked by an Inmate

HD 0:30 / 43:00

Correctional Officer Tied Up and Fucked by an Inmate

AEBN 6 years ago

Airport Security 7

58% HD 0:30 / 1:33:00

Airport Security 7

AEBN 12 years ago

Raw Justice

HD 0:30 / 1:38:00

AEBN 6 years ago

Alrik's Crazy Captor Pt 1 (CUSTOM ORDER)

65% HD 0:25 / 12:07

Alrik's Crazy Captor Pt 1 (CUSTOM ORDER)

Clips4sale 3 years ago

Porn Prison

55% HD 0:30 / 1:35:00

AEBN 6 years ago

The Best Of Jeff Stryker

66% HD 0:30 / 1:13:00

The Best Of Jeff Stryker

AEBN 16 years ago

KingMarti: Escape the Cage: Make Your Break Before It's Too Late!

42% HD 0:30 / 11:11

KingMarti: Escape the Cage: Make Your Break Before It's Too Late!

Clips4sale 3 months ago

The Terrorist's Ransom

48% 0:11 / 55:13

The Terrorist's Ransom

Clips4sale 1 year ago

Macrophilia - you and your boyfriend vore

Macrophilia - you and your boyfriend vore

Clips4sale 2 years ago

Obsessed with this delinquent's ass

59% HD 3:20 / 18:45

Obsessed with this delinquent's ass

DarkCruising 1 year ago

Bound In Public: Lockup, Cell Extraction And Prison Gang Fuck

65% HD 0:30 / 48:00

Bound In Public: Lockup, Cell Extraction And Prison Gang Fuck

AEBN 11 years ago

Matt Hughes: Monster

55% HD 0:30 / 3:25:00

Matt Hughes: Monster

AEBN 10 years ago

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