Jail Videos - Gay (2,107)

Spartacus

51% HD 0:30 / 2:03:00

AEBN 17 years ago

Powertool

52% HD 0:30 / 1:53:00

AEBN 17 years ago

A Brief Quickie with My Stepson.

56% HD 0:39 / 9:43

A Brief Quickie with My Stepson.

FapHouse 6 months ago

Horny Pervert Takes Some Rough Justice

Premium HD 50:15

Horny Pervert Takes Some Rough Justice

KinkMen 9 years ago

Hot Men Pulling Down Pants

Premium 58% HD 20:28

Hot Men Pulling Down Pants

Mr.Man 5 years ago

Airport Security 24

43% HD 0:30 / 1:04:00

Airport Security 24

AEBN 7 years ago

Joe Gage Sex Files 22: Diary Of A Prison Doctor

55% 0:45 / 24:33

Joe Gage Sex Files 22: Diary Of A Prison Doctor

NakedSword 7 years ago

Falcon Icons: The 1970's

62% HD 0:30 / 2:14:00

Falcon Icons: The 1970's

AEBN 4 years ago

Cops And Robbers

64% HD 0:30 / 1:43:00

Cops And Robbers

AEBN 8 years ago

Prison Mecs 2

HD 0:30 / 1:27:00

AEBN 11 years ago

Big Ass Deeper Anal Make to the Ass with Full Strength

51% 0:39 / 6:05

Big Ass Deeper Anal Make to the Ass with Full Strength

FapHouse 2 months ago

Raw Escape

HD 0:30 / 1:38:00

AEBN 12 years ago

Men-rise of the Prison Bitch Part 3 - Jake Preston, Bruce Jones, Joel Hart

45% HD 0:39 / 23:50

Men-rise of the Prison Bitch Part 3 - Jake Preston, Bruce Jones, Joel Hart

FapHouse 2 months ago

Young Prisoner Inmate in Convict Uniform Jerks off His Thick Cock with Huge Cumshot

Young Prisoner Inmate in Convict Uniform Jerks off His Thick Cock with Huge Cumshot

FapHouse 1 month ago

He Drinks Piss In Jail

47% HD 3:00 / 9:00

He Drinks Piss In Jail

AEBN 7 months ago

Prison Break

HD 0:30 / 1:31:00

AEBN 3 years ago

G.I. Hole

64% HD 0:30 / 1:37:00

AEBN 2 years ago

Youngperps - Bratty Attitude Twink Gets Asshole Pulverized by Hung 2 Security Guards

57% HD 0:39 / 26:44

Youngperps - Bratty Attitude Twink Gets Asshole Pulverized by Hung 2 Security Guards

FapHouse 8 months ago

Hot As Hell : Actors Who Have Played Satan

Premium 57% HD 15:20

Hot As Hell : Actors Who Have Played Satan

Mr.Man 4 years ago

My First Time Avoiding Jail

48% 0:45 / 24:02

My First Time Avoiding Jail

NakedSword 1 year ago

Folsom Prison

72% HD 0:30 / 2:36:00

AEBN 7 years ago

Sex Fanatics in Prison Part #5 - Fully Remastered in HD

HD 0:39 / 17:18

Sex Fanatics in Prison Part #5 - Fully Remastered in HD

FapHouse 1 year ago

Robin Vs Bane

FapHouse 2 weeks ago

Submission Prison

61% 0:45 / 32:48

Submission Prison

NakedSword 5 years ago

The Walking Dad

75% 4K 1:07 / 1:02:21

The Walking Dad

SayUncle 2 years ago

im not gay! (pt2) prison boy slaps and spreads the jailpussy black asshole in slow motion - starring dj buttpussy

HD 0:30 / 29:15

im not gay! (pt2) prison boy slaps and spreads the jailpussy black asshole in slow motion - starring dj buttpussy

PornBox 6 days ago

Raw Piss Prison

55% HD 0:30 / 2:01:00

Raw Piss Prison

AEBN 16 years ago

The New Officer Maguire and The Horny Sex Offender

62% 0:11 / 48:42

The New Officer Maguire and The Horny Sex Offender

Clips4sale 1 year ago

Prepping His Ass for Prison

57% HD 0:39 / 32:22

Prepping His Ass for Prison

FapHouse 2 years ago

I Finally Got Fucked by My Stepbrother Best Friend Part 6

65% HD 0:39 / 6:09

I Finally Got Fucked by My Stepbrother Best Friend Part 6

FapHouse 4 months ago

Airport Security 8

62% HD 0:30 / 1:26:00

Airport Security 8

AEBN 12 years ago

Irredeemable Piece of Ass

55% HD 0:39 / 31:55

Irredeemable Piece of Ass

FapHouse 1 year ago

The Best Of Matthew Rush

HD 0:30 / 3:09:00

The Best Of Matthew Rush

AEBN 15 years ago

Horny Heatwave Part 3

65% 0:39 / 2:00:04

Horny Heatwave Part 3

FapHouse 5 months ago

Duty Bound 46

64% HD 0:30 / 59:00

AEBN 8 years ago

The Mountain Prison 4

55% HD 0:30 / 8:00

The Mountain Prison 4

AEBN 6 months ago

Hungry for Prisoner Cum

64% HD 0:39 / 24:10

Hungry for Prisoner Cum

FapHouse 3 months ago

Bound Prison: Bad Boy Inmate Cliff Jensen Breaks In New Guard DelRay

HD 0:30 / 50:00

Bound Prison: Bad Boy Inmate Cliff Jensen Breaks In New Guard DelRay

AEBN 3 years ago

Duty Bound 36

HD 0:30 / 1:07:00

AEBN 9 years ago

Prisoner Of War

64% HD 0:30 / 1:34:00

Prisoner Of War

AEBN 8 years ago

The Photographer’s New Offense

63% 4K 1:00 / 23:34

The Photographer’s New Offense

YoungPerps 2 years ago

Lock Down

47% HD 0:30 / 1:52:00

AEBN 14 years ago

Who's Using Who?: Ricky Sinz Takes Down Cole Brooks

Premium HD 53:25

Who's Using Who?: Ricky Sinz Takes Down Cole Brooks

KinkMen 5 years ago

Powertool 2: Breaking Out

72% HD 0:30 / 1:26:00

Powertool 2: Breaking Out

AEBN 16 years ago

Hole Patrol

56% HD 0:30 / 2:42:00

AEBN 12 years ago

A Guide To Sex In Prison

47% HD 0:30 / 1:23:00

A Guide To Sex In Prison

AEBN 8 years ago

Uniform Men

54% HD 0:30 / 2:20:00

AEBN 13 years ago

My First Time Avoiding Jail

HD 0:30 / 1:41:00

My First Time Avoiding Jail

AEBN 2 years ago

Sex Maniacs In Prison

HD 0:30 / 1:43:00

Sex Maniacs In Prison

AEBN 1 year ago

Handsome Hippie Hitchhiker Gets Bound And Fucked

Handsome Hippie Hitchhiker Gets Bound And Fucked

Clips4sale 2 months ago

Giants Capture Human For Domination And Humiliation

47% 0:59 / 16:21

Giants Capture Human For Domination And Humiliation

Clips4sale 6 months ago

Beverly Hills 90210 Hotties

Premium 65% HD 24:54

Beverly Hills 90210 Hotties

Mr.Man 6 years ago

Big Bottle in My Anal

Big Bottle in My Anal

FapHouse 1 year ago

SPIT AND PISS COVERED

46% 3:41 / 15:04

SPIT AND PISS COVERED

CazzoFilm 1 year ago

im not gay! (pt2) prison boy slaps and spreads the jailpussy black asshole in slow motion - starring dj buttpussy

HD 0:30 / 29:15

im not gay! (pt2) prison boy slaps and spreads the jailpussy black asshole in slow motion - starring dj buttpussy

AnalVids 1 week ago

prison boy shows off what he larned (anal in a doggystyle) - starring dj buttpussy

prison boy shows off what he larned (anal in a doggystyle) - starring dj buttpussy

AnalVids 2 weeks ago

Ukag-007 Prisoner / Love Me Don't Go

51% HD 0:39 / 32:15

Ukag-007 Prisoner / Love Me Don't Go

FapHouse 2 months ago

Band Of Breeders Part 1

Premium HD 28:51

Band Of Breeders Part 1

Men 2 weeks ago

FAKEhub Originals Bloopers

Premium HD 12:44

FAKEhub Originals Bloopers

Fakehub 6 years ago

Hard Time, Harder Fuck

Premium HD 29:02

Hard Time, Harder Fuck

Men 3 weeks ago

Rocco Steele's Dad Goes To Prison

63% 0:45 / 21:50

Rocco Steele's Dad Goes To Prison

NakedSword 6 years ago

Top Tryout | LOGAN CROSS Vol. 1

47% HD 1:31 / 25:56

Top Tryout | LOGAN CROSS Vol. 1

TwinkTop 3 years ago

Prisoners of Sex

66% HD 0:30 / 1:44:00

Prisoners of Sex

AEBN 18 years ago

Wait...Were Those His Balls?

Premium 42% HD 20:42

Wait...Were Those His Balls?

Mr.Man 5 years ago

Prison Camp - Fucked into Submission

57% HD 1:20 / 1:30:34

Prison Camp - Fucked into Submission

DarkCruising 10 years ago

Viking Prisoner Roleplay

55% HD 2:00 / 7:20

Viking Prisoner Roleplay

Flirt4Free 2 years ago

Best Frontal Nudity of the 1970's

Premium 48% HD 18:03

Best Frontal Nudity of the 1970's

Mr.Man 6 years ago

PRISON BITCH FOR BBC

4K 0:30 / 15:54

PRISON BITCH FOR BBC

Clips4sale 1 year ago

Take a Peek at the Men's Locker Room, and You'll Get a Cock in Your Ass

59% 4K 1:26 / 26:11

Take a Peek at the Men's Locker Room, and You'll Get a Cock in Your Ass

YoungPerps 1 week ago

SPIT AND PISS COVERED

47% HD 3:41 / 15:04

SPIT AND PISS COVERED

DarkCruising 1 year ago

Thirsty for Jizz Cruising

HD 0:39 / 16:25

Thirsty for Jizz Cruising

FapHouse 2 months ago

Prison Mecs

55% 0:45 / 15:17

NakedSword 11 years ago

Big Black Indian Cock Fuck to Desi Asshole and Cum Inside. Teen Boy Sex with Black Bangla Boy. Twink Gay Sex Xx

59% HD 0:39 / 8:32

Big Black Indian Cock Fuck to Desi Asshole and Cum Inside. Teen Boy Sex with Black Bangla Boy. Twink Gay Sex Xx

FapHouse 6 months ago

Before he gets convicted and becomes &#039_Prison Pussy&#039_, all he has to prove his innocence is the Truth, and his tight ass! Find out if they get his Hole A Parole! Mugshots Scene 4 : Chad Hunt &amp_ Scott Campbell

Premium HD 25:33

Before he gets convicted and becomes &#039_Prison Pussy&#039_, all he has to prove his innocence is the Truth, and his tight ass! Find out if they get his Hole A Parole! Mugshots Scene 4 : Chad Hunt &amp_ Scott Campbell

xnxxGold 3 years ago

Rodney Steele Picks Up A Hitchhiker

40% HD 3:32 / 1:30:00

Rodney Steele Picks Up A Hitchhiker

AEBN 8 years ago

bbc cock smacking finger fucking bitch slapping and stretching the big loose asshole of skinny twink - dj buttpussy

HD 0:30 / 26:55

bbc cock smacking finger fucking bitch slapping and stretching the big loose asshole of skinny twink - dj buttpussy

PornBox 2 years ago

ARRESTED & FIST FUCKED BY BBC

ARRESTED & FIST FUCKED BY BBC

Clips4sale 1 year ago

Weekend Offenders

39% HD 0:30 / 13:00

Weekend Offenders

AEBN 2 years ago

Men On Edge: Edging A Straight Cop

64% HD 0:30 / 56:00

Men On Edge: Edging A Straight Cop

AEBN 11 years ago

Hot Indian TV and Movies!

Premium 40% HD 30:44

Hot Indian TV and Movies!

Mr.Man 2 years ago

Prison Fuck with Fox Rifler

58% 0:30 / 20:30

Prison Fuck with Fox Rifler

Clips4sale 4 months ago

Rise Of The Prison Bitch Part 2

Premium 44% HD 19:38

Rise Of The Prison Bitch Part 2

Young tattooed prisoner chases my dick and then fucks me in the ass! Fuck fuck fuck

Premium HD 15:50

Young tattooed prisoner chases my dick and then fucks me in the ass! Fuck fuck fuck

XVideosRed 5 months ago

James and Alex, barely out of prison, find themselves in an indecent masked position. The big surprise is their big long black cocks penetrating each other for the first time in their first fucking e

Premium HD 19:13

James and Alex, barely out of prison, find themselves in an indecent masked position. The big surprise is their big long black cocks penetrating each other for the first time in their first fucking e

XVideosRed 2 years ago

Horny Police Guy Destroys a Black Prisoner with Hairy Ass

65% 0:39 / 18:24

Horny Police Guy Destroys a Black Prisoner with Hairy Ass

FapHouse 9 months ago

All Rise, Especially Your Cock

67% HD 1:09 / 21:29

All Rise, Especially Your Cock

Men 4 months ago

Mind the Gap; Mummified Orgasm of the Tape Bound Twink

72% 0:30 / 16:05

Mind the Gap; Mummified Orgasm of the Tape Bound Twink

Clips4sale 1 year ago

Bonded Out and Pounded Down

62% HD 0:39 / 30:26

Bonded Out and Pounded Down

FapHouse 1 year ago

The Iron Pa Part 2: Jailhouse Match

4K 1:04 / 34:23

The Iron Pa Part 2: Jailhouse Match

SayUncle 1 year ago

A Story in Prison

59% HD 2:00 / 28:25

A Story in Prison

Flirt4Free 3 years ago

Undressed To Impress

Premium 65% HD 33:14

Undressed To Impress

Mr.Man 3 years ago

Prison Guard Gets Ravaged!

59% 1:05 / 34:29

Prison Guard Gets Ravaged!

RawDads 3 years ago

Black Breeders 111

58% 0:39 / 5:08

Black Breeders 111

FapHouse 4 months ago

Rocco Reed: Straight To Gay

49% HD 0:30 / 2:26:00

Rocco Reed: Straight To Gay

AEBN 9 years ago

His imprisonment

47% HD 0:39 / 2:26

His imprisonment

FapHouse 4 years ago

Milk Express Machine

Milk Express Machine

FapHouse 1 year ago

FUCKING THE PRISON BREAK ACTOR IN SEARCH OF THE TRUTH

Premium HD 27:08

FUCKING THE PRISON BREAK ACTOR IN SEARCH OF THE TRUTH

xnxxGold 1 year ago

Bad Boys 2

HD 0:30 / 1:21:00

AEBN 18 years ago

james and alex, barely out of prison, find themselves in an indecent masked position. the big surprise is their big long black cocks penetrating each other for the first time in their first fucking e

58% HD 0:30 / 19:12

james and alex, barely out of prison, find themselves in an indecent masked position. the big surprise is their big long black cocks penetrating each other for the first time in their first fucking e

PornBox 2 years ago

Prison Shower

59% HD 0:30 / 1:34:00

AEBN 9 years ago

All Night Without Getting Down with My Bed Makes Nothing.

46% HD 0:39 / 8:28

All Night Without Getting Down with My Bed Makes Nothing.

FapHouse 3 months ago

Prison Baes

Premium 35% HD 23:16

Mr.Man 2 years ago

My 1000 Set of Photos

My 1000 Set of Photos

FapHouse 2 weeks ago

Alpha Stud Returns Part 3

50% HD 0:12 / 9:10

Alpha Stud Returns Part 3

AdultPrime 6 years ago

Prisoner Role Play

Prisoner Role Play

Flirt4Free 2 years ago

Sounding The Inmate While Bound In A Straitjacket (4K)

4K 0:24 / 20:42

Sounding The Inmate While Bound In A Straitjacket (4K)

Clips4sale 2 months ago

Destroy Your Ass For Inmates - Anal Masturbation Instructions From Prison

44% HD 0:10 / 32:16

Destroy Your Ass For Inmates - Anal Masturbation Instructions From Prison

LoyalFans 1 year ago

Giant Eats Your Friends and You 1080p - Toms Fetish Store

Giant Eats Your Friends and You 1080p - Toms Fetish Store

Clips4sale 1 month ago

Breaking and Entering

Breaking and Entering

Clips4sale 2 years ago

BBC Prison - Mind Fuck MindScape - The Goddess Of Destruction

45% HD 0:25 / 18:08

BBC Prison - Mind Fuck MindScape - The Goddess Of Destruction

Clips4sale 1 year ago

Ride Or Die: Hard Time - Director's Cut

64% HD 0:30 / 1:47:00

Ride Or Die: Hard Time - Director's Cut

AEBN 3 years ago

Will Justice; Dungeon of Doom

34% 0:11 / 14:22

Will Justice; Dungeon of Doom

Clips4sale 1 year ago

Tattooed Men Scene-4_face-to-face in Prison Between the Guard and Tattooed Colleague

HD 0:39 / 18:59

Tattooed Men Scene-4_face-to-face in Prison Between the Guard and Tattooed Colleague

FapHouse 1 year ago

Retro Hotness: Pre-1980 Nudity

Premium 55% HD 31:44

Retro Hotness: Pre-1980 Nudity

Mr.Man 6 years ago

Hairy perv gets taken downtown & gang fucked by the whole jail house

Premium 49% HD 41:10

Hairy perv gets taken downtown & gang fucked by the whole jail house

KinkMen 11 years ago

Arrogant Cop Tormented by His Prisoner

Premium 59% HD 58:21

Arrogant Cop Tormented by His Prisoner

KinkMen 10 years ago

Convict Series - "In Prison, You'd be my Bitch!"

Premium 72% HD 49:04

Convict Series - "In Prison, You'd be my Bitch!"

KinkMen 9 years ago

Fight For My Hole

Premium HD 24:42

Fight For My Hole

Men 14 years ago

Lockup, Cell Extraction & Prison Sex - Part Two

Premium 66% HD 54:53

Lockup, Cell Extraction & Prison Sex - Part Two

KinkMen 12 years ago

Shameless Nudity Throughout the Years

Premium 55% HD 15:23

Shameless Nudity Throughout the Years

Mr.Man 4 years ago

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