Jail (19,794)

Nick Jacobs, Kym Wilde and Penny Flame

HD 0:34 / 36:25

Nick Jacobs, Kym Wilde and Penny Flame

Kink 20 years ago

Whipping prisoners in Warsaw Prison

72% 0:23 / 10:42

Whipping prisoners in Warsaw Prison

Clips4sale 2 years ago

The arrest of fighters Meelina and Francesca

61% 0:15 / 19:33

The arrest of fighters Meelina and Francesca

Clips4sale 1 year ago

CUTTING his HAIR, humiliated and WHIPPED in pieces

4K 0:17 / 18:12

CUTTING his HAIR, humiliated and WHIPPED in pieces

Clips4sale 3 weeks ago

Boudoir Caning - The Peeping Mechanic 02

76% 0:14 / 8:18

Boudoir Caning - The Peeping Mechanic 02

Clips4sale 1 year ago

Correctional Officer Gets A Double Blowjob

66% HD 0:10 / 5:40

Correctional Officer Gets A Double Blowjob

LoyalFans 1 month ago

Marked For Our Pleasure

66% 0:18 / 20:33

Marked For Our Pleasure

Clips4sale 4 weeks ago

robbers shalina devine and angela heart get out of jail with a dp orgy gp2299

51% HD 0:31 / 56:21

robbers shalina devine and angela heart get out of jail with a dp orgy gp2299

AnalVids 3 years ago

Femdom Prison - Chastity Prisoner (1080p)

HD 0:29 / 14:55

Femdom Prison - Chastity Prisoner (1080p)

Clips4sale 1 month ago

Lesbians in Jail: BONDAGE is the NEW BLACK! STANDARD DEF

55% 1:00 / 18:28

Lesbians in Jail: BONDAGE is the NEW BLACK! STANDARD DEF

Clips4sale 8 months ago

Cherry English on the One Bar Prison

59% HD 0:11 / 4:13

Cherry English on the One Bar Prison

Clips4sale 2 years ago

tiny inmate must suffer part 3 - mp4 720p

59% HD 0:23 / 29:01

tiny inmate must suffer part 3 - mp4 720p

Clips4sale 4 months ago

A witch gets her pubic hair plucked out before screw clamps are used to secure her slim body on the rack

60% 0:32 / 11:11

A witch gets her pubic hair plucked out before screw clamps are used to secure her slim body on the rack

Clips4sale 1 year ago

Beauty Lady Get Hard Fuck at Prison - 3D Animation Hentai

60% HD 0:39 / 20:26

Beauty Lady Get Hard Fuck at Prison - 3D Animation Hentai

FapHouse 1 month ago

EmilyAddams48h - The ultimate Challenge for the young German Slave Slut - Chapter 16 - Maya and the Strap on - Part 02 (wmv)

56% HD 0:30 / 16:57

EmilyAddams48h - The ultimate Challenge for the young German Slave Slut - Chapter 16 - Maya and the Strap on - Part 02 (wmv)

Clips4sale 1 month ago

Military Whistleblower Amelia Jane Rutherford Spanked, Strapped and Caned by Stern CO (SE0012, 1080p MP4)

64% HD 0:30 / 35:00

Military Whistleblower Amelia Jane Rutherford Spanked, Strapped and Caned by Stern CO (SE0012, 1080p MP4)

Clips4sale 9 months ago

Dissident – electro treatment - Episode 2 of 4

57% 0:11 / 14:14

Dissident – electro treatment - Episode 2 of 4

Clips4sale 2 years ago

Magical anal

66% HD 0:39 / 1:12:26

FapHouse 7 years ago

Mooing Witch – Maid Judith has to suck the monk's cock and gets her tits milked like a dairy cow while she is treated like cattle in the stable

71% 1:00 / 23:05

Mooing Witch – Maid Judith has to suck the monk's cock and gets her tits milked like a dairy cow while she is treated like cattle in the stable

Clips4sale 1 month ago

Zoe The Prison Slut 2 (4K)

63% 4K 0:59 / 41:44

Zoe The Prison Slut 2 (4K)

Clips4sale 2 weeks ago

Tit Slave Eva - 48 hours in Tit Hell Part 1 - splitter 02 - SD (wmv)

53% 0:11 / 9:08

Tit Slave Eva - 48 hours in Tit Hell Part 1 - splitter 02 - SD (wmv)

Clips4sale 2 years ago

Obedient Prison Guard 3 - Asteria Jade - 4k

60% 4K 0:29 / 36:23

Obedient Prison Guard 3 - Asteria Jade - 4k

Clips4sale 2 weeks ago

The Rookie

63% HD 0:56 / 50:45

Kink 9 years ago

Chloe Toy: Witch Stripped and Chained (VID0804 1080p MP4)

53% HD 0:29 / 18:32

Chloe Toy: Witch Stripped and Chained (VID0804 1080p MP4)

Clips4sale 2 years ago

Fierce Fairy – the wild natural girl gets stretched and tormented on the rack

72% 0:11 / 16:59

Fierce Fairy – the wild natural girl gets stretched and tormented on the rack

C4S 2 years ago

Brianna Olivia & Rachel Adams; Beauty and The Bitch (Part One)

59% 0:30 / 15:17

Brianna Olivia & Rachel Adams; Beauty and The Bitch (Part One)

Clips4sale 1 week ago

When Cindy is the law the only way for Allie to get out of going to Jail is by giving herself to Cindy

Premium HD 44:10

When Cindy is the law the only way for Allie to get out of going to Jail is by giving herself to Cindy

XVideosRed 1 year ago

807 Blissfully Satisfied

69% 4K 0:25 / 8:30

807 Blissfully Satisfied

Clips4sale 1 year ago

Captive Slut

40% HD 0:32 / 44:09

Kink 17 years ago

A policeman has rough sex with a brunette whore with a huge ass in prison - Max Betancur &amp_ Carla Morelli

Premium HD 21:49

A policeman has rough sex with a brunette whore with a huge ass in prison - Max Betancur &amp_ Carla Morelli

XVideosRed 4 months ago

Private Room Strip By Sophia Has The Guards Tongues Wagging!!!!! - MP4

57% HD 0:11 / 6:30

Private Room Strip By Sophia Has The Guards Tongues Wagging!!!!! - MP4

Clips4sale 3 years ago

STASI Verzückung - eingeschleust, verführt, benutzt - CruelAlice prison play Verhör

58% HD 0:31 / 45:37

STASI Verzückung - eingeschleust, verführt, benutzt - CruelAlice prison play Verhör

Clips4sale 2 years ago

Prisoner of Femdom (1080p)

70% HD 0:30 / 9:56

Prisoner of Femdom (1080p)

Clips4sale 10 months ago

Cherry English – Spring Loaded Deepthroat Predicament

75% 4K 0:10 / 4:26

Cherry English – Spring Loaded Deepthroat Predicament

Clips4sale 8 months ago

48h Prison Extreme Day 2 – Girl gets put on the leash for a walk

56% 0:11 / 6:39

48h Prison Extreme Day 2 – Girl gets put on the leash for a walk

Clips4sale 1 year ago

Luna Lux and Celene Thorne Arrest Roman

52% 0:30 / 21:49

Luna Lux and Celene Thorne Arrest Roman

Clips4sale 3 weeks ago

Prison: Emiri

58% 0:30 / 7:56

Clips4sale 2 weeks ago

Oliver Taken Into Custody By Two Female Officers

63% 0:11 / 25:15

Oliver Taken Into Custody By Two Female Officers

Erica Lauren - MILF Prisoner Conjugal FootJob (4K - UHD 2160p MP4)

69% 4K 0:11 / 15:10

Erica Lauren - MILF Prisoner Conjugal FootJob (4K - UHD 2160p MP4)

Clips4sale 1 year ago

Busty witch gets a special ass treatment

57% 0:11 / 7:53

Busty witch gets a special ass treatment

C4S 2 years ago

Get Naked For Me (4K) - Cadence Lux

70% 4K 0:37 / 7:51

Get Naked For Me (4K) - Cadence Lux

Clips4sale 5 months ago

Alice - Water Torment

56% 0:11 / 18:50

Alice - Water Torment

C4S 2 years ago

Cockboarding

66% 1:00 / 6:25

Clips4sale 1 week ago

prison examination - mp4 1080p

60% HD 0:20 / 11:46

prison examination - mp4 1080p

Clips4sale 1 year ago

Double Officers Pegging | Evilwoman, Mistress Glamorous

Double Officers Pegging | Evilwoman, Mistress Glamorous

Clips4sale 4 days ago

Electro Training for Sophie

51% 0:11 / 6:36

Electro Training for Sophie

C4S 2 years ago

2 Cruel whipping female slave - [720p]

60% HD 0:19 / 4:44

2 Cruel whipping female slave - [720p]

Clips4sale 1 year ago

Wonder Woman: The Doomsday Missile (MP4 1080p) - Jasmine St James featuring Rachel Adams

HD 1:00 / 26:28

Wonder Woman: The Doomsday Missile (MP4 1080p) - Jasmine St James featuring Rachel Adams

Clips4sale 1 year ago

Officer Nikki Darling Arrests Sultry

48% 4K 0:30 / 20:31

Officer Nikki Darling Arrests Sultry

Clips4sale 4 months ago

The Kinky Journalist

66% HD 0:39 / 58:57

The Kinky Journalist

Kink 14 years ago

A witch is dangling over small flames

54% 0:11 / 8:51

A witch is dangling over small flames

C4S 2 years ago

The Spain Files - Katarina Blade - Cruel Hogtie Transport for a sexy Prisoner - Part 1 wmv SD

54% HD 0:11 / 15:14

The Spain Files - Katarina Blade - Cruel Hogtie Transport for a sexy Prisoner - Part 1 wmv SD

Clips4sale 2 years ago

Miss Brooke, Lucy Lee and Gallant Reflex

54% 0:11 / 15:09

Miss Brooke, Lucy Lee and Gallant Reflex

A judicial punishment of 3 female prisoners (Shot in 4K)

66% 4K 0:56 / 1:49:41

A judicial punishment of 3 female prisoners (Shot in 4K)

Clips4sale 2 years ago

Reach around handjob with HOM part 7!!

57% HD 0:16 / 6:37

Reach around handjob with HOM part 7!!

Clips4sale 4 months ago

Argentinian Carriage Whip and some more nasty things 02

Argentinian Carriage Whip and some more nasty things 02

Clips4sale 1 year ago

PUNISHMENT BY MISTRESS ANYA

59% 0:10 / 11:06

PUNISHMENT BY MISTRESS ANYA

Clips4sale 3 years ago

MissaX - A Villain on the Loose pt2 854x480

55% HD 0:11 / 45:04

MissaX - A Villain on the Loose pt2 854x480

Clips4sale 4 years ago

Conjugal fantasy gone wild! Cute prison pen-pal taken down by ex-cons.

43% HD 1:22 / 59:42

Conjugal fantasy gone wild! Cute prison pen-pal taken down by ex-cons.

Kink 10 years ago

Falling for Stepmom

55% HD 0:39 / 58:10

Falling for Stepmom

FapHouse 1 year ago

Private Company for transfering inmates - Part 1

60% 0:21 / 16:54

Private Company for transfering inmates - Part 1

Clips4sale 2 years ago

Zlata and her little Fan (noughty Giantess) 4K Version VR360

55% 4K 0:21 / 21:00

Zlata and her little Fan (noughty Giantess) 4K Version VR360

Clips4sale 2 months ago

Pregnant latina shoves big dildo in her swollen pussy

73% HD 0:51 / 13:40

Pregnant latina shoves big dildo in her swollen pussy

Slave Mila’s Prison Interrogation Part 2: The Harrowing Whip (720p)

61% 4K 0:32 / 24:48

Slave Mila’s Prison Interrogation Part 2: The Harrowing Whip (720p)

Clips4sale 7 months ago

Agent’s Kinky Trap Ep 1

Agent’s Kinky Trap Ep 1

Clips4sale 1 week ago

All FOUR Cabin Prisoner clips in ONE! (loser gets URINATED on)!!

79% HD 0:45 / 20:25

All FOUR Cabin Prisoner clips in ONE! (loser gets URINATED on)!!

Clips4sale 5 months ago

Still in Chastity!! Crotchless Pantyhose!

HD 0:39 / 18:06

Still in Chastity!! Crotchless Pantyhose!

FapHouse 1 month ago

Eduarda Leal with Ms VBlack in: Medical Play & CBT in FemDom Prison - Part 3 (1080 EN-sub)

79% HD 0:30 / 11:41

Eduarda Leal with Ms VBlack in: Medical Play & CBT in FemDom Prison - Part 3 (1080 EN-sub)

Clips4sale 4 months ago

pony riding in prison - wmv 720p

56% HD 0:16 / 15:18

pony riding in prison - wmv 720p

Clips4sale 2 years ago

prison dick exam

59% 0:11 / 10:04

prison dick exam

Clips4sale 2 years ago

Crammed in a Cage - BondageFan70 and Elise Graves - Bondage slut bound in leather makes a mess while totally immobilized and electro-fucked in a metal cage

56% HD 0:57 / 32:53

Crammed in a Cage - BondageFan70 and Elise Graves - Bondage slut bound in leather makes a mess while totally immobilized and electro-fucked in a metal cage

Clips4sale 9 months ago

A beautiful prisoner is punished (Shot in 4K)

64% 4K 0:58 / 29:22

A beautiful prisoner is punished (Shot in 4K)

Clips4sale 1 year ago

Ruined orgasms and ticklish torment: Matriarch Ezada Sinn, Mistress Lexy Noir, and Goddess Samariel's ultimate punishment

65% 1:00 / 1:01:54

Ruined orgasms and ticklish torment: Matriarch Ezada Sinn, Mistress Lexy Noir, and Goddess Samariel's ultimate punishment

Clips4sale 5 months ago

Yasmeena caning 2310

61% HD 0:11 / 7:28

Yasmeena caning 2310

Clips4sale 2 years ago

Your Only Option (2K) - Cadence Lux

51% 4K 0:52 / 13:18

Your Only Option (2K) - Cadence Lux

Clips4sale 1 month ago

Anna Luna’s Secret Fantasy - Ticklish Prisoner Roleplay (FULL HD MP4)

59% 4K 0:16 / 24:02

Anna Luna’s Secret Fantasy - Ticklish Prisoner Roleplay (FULL HD MP4)

Clips4sale 2 weeks ago

August Special 22 - Titslave Eva - 48 Hours in Tit Hell - Episode 10 - FULL CLIP - HD (mp4)

52% HD 0:11 / 41:57

August Special 22 - Titslave Eva - 48 Hours in Tit Hell - Episode 10 - FULL CLIP - HD (mp4)

Clips4sale 2 years ago

A new One Bar Prison friend!

54% 4K 0:11 / 6:41

A new One Bar Prison friend!

Clips4sale 2 years ago

Alyssa - Prison Transfer Footworship

58% 0:15 / 15:47

Alyssa - Prison Transfer Footworship

Clips4sale 8 months ago

Prima Donna (2K) - Jasmine St James

54% 4K 0:54 / 15:09

Prima Donna (2K) - Jasmine St James

Clips4sale 3 months ago

Anal Slut Prison Whores

71% HD 0:43 / 1:17:13

Anal Slut Prison Whores

Kink 11 years ago

Emiri's Adventure

55% 0:12 / 31:16

Emiri's Adventure

A bad cop for Meelina (part2)

66% HD 0:25 / 17:09

A bad cop for Meelina (part2)

Clips4sale 3 years ago

interrogate the spy - wmv 1080p

63% HD 0:27 / 16:43

interrogate the spy - wmv 1080p

Clips4sale 5 months ago

FOLSOM PRISON RED

58% HD 0:11 / 13:53

FOLSOM PRISON RED

Clips4sale 3 years ago

Jailbreak

71% 0:11 / 20:46

Clips4sale 3 years ago

prison examination - wmv 720p

55% HD 0:20 / 11:46

prison examination - wmv 720p

Clips4sale 1 year ago

Plants vs Cunts Vol 12

64% 0:30 / 12:22

Plants vs Cunts Vol 12

C4S 1 month ago

Demi the corrupted police woman

Demi the corrupted police woman

Clips4sale 1 year ago

Cuffed and Fucked

56% 0:29 / 21:11

Cuffed and Fucked

Clips4sale 8 months ago

Double discounted clip of Bella's severe whipping and converse punishment and Bella strapped caned and buttplugged (Shot in 4K)

59% 4K 0:59 / 58:37

Double discounted clip of Bella's severe whipping and converse punishment and Bella strapped caned and buttplugged (Shot in 4K)

Clips4sale 5 months ago

Kate ass whipping 2825

Kate ass whipping 2825

Clips4sale 2 weeks ago

Hunger

57% HD 0:29 / 42:37

Clips4sale 10 months ago

The Fate Of The Forger & Stripping A Cop (4K) - Lydia Lael

57% 4K 1:00 / 12:54

The Fate Of The Forger & Stripping A Cop (4K) - Lydia Lael

Clips4sale 1 year ago

Lady Lyne on the One Bar Prison

Lady Lyne on the One Bar Prison

Clips4sale 5 months ago

Lotus e Ju: le prigioniere (Prima parte) - Lotus and Ju: the prisoners (Part one) (LESBIAN DOMINATION)

61% 0:47 / 33:15

Lotus e Ju: le prigioniere (Prima parte) - Lotus and Ju: the prisoners (Part one) (LESBIAN DOMINATION)

Clips4sale 1 year ago

Police asses fucked in xxx orgy

Police asses fucked in xxx orgy

FapHouse 2 years ago

Aubrey – steel prisoner

66% 4K 0:10 / 4:34

Aubrey – steel prisoner

Clips4sale 7 months ago

Liz Rainbow impaled

73% HD 0:11 / 5:05

Liz Rainbow impaled

Clips4sale 3 years ago

Unicorn Riah Meets Dirty Ol' Man

67% 0:11 / 17:30

Unicorn Riah Meets Dirty Ol' Man

Clips4sale 2 years ago

A Payment Made with Pain - MP4 720x480

79% 4K 0:55 / 15:20

A Payment Made with Pain - MP4 720x480

Clips4sale 7 months ago

Last Mile Lesbians (Mobile)

Last Mile Lesbians (Mobile)

Clips4sale 1 year ago

LCT224h Pantyhose feet Glass Table Trample cock Ejaculation Female Officer XG Boots Humiliation Trampled slaves Face

63% 1:00 / 34:44

LCT224h Pantyhose feet Glass Table Trample cock Ejaculation Female Officer XG Boots Humiliation Trampled slaves Face

Clips4sale 1 year ago

tiny inmate must suffer part 4 - mp4 720p

65% HD 0:24 / 27:45

tiny inmate must suffer part 4 - mp4 720p

Clips4sale 4 months ago

Blowjob Under the Watch of the Prison Guards

65% HD 0:39 / 6:01

Blowjob Under the Watch of the Prison Guards

FapHouse 1 year ago

Tickling torment with handjob and CBT

66% HD 0:25 / 20:04

Tickling torment with handjob and CBT

Clips4sale 3 years ago

When daring reporter Paris Kennedy followed a hot tip, she was grabbed, then bound, gagged and locked in a jail cell!

When daring reporter Paris Kennedy followed a hot tip, she was grabbed, then bound, gagged and locked in a jail cell!

Clips4sale 2 years ago

Cherokee and Damien

59% HD 0:23 / 37:43

Cherokee and Damien

Kink 20 years ago

Sadistic Prison Guard: Interrogation

58% HD 1:00 / 11:48

Sadistic Prison Guard: Interrogation

Clips4sale 1 year ago

Lil Missy & Latina: Rope and Tape Justice for the Negligent (4K)

61% 4K 0:30 / 17:37

Lil Missy & Latina: Rope and Tape Justice for the Negligent (4K)

Clips4sale 3 weeks ago

Full Prison Sissy Transformation (1080p)

HD 0:19 / 14:12

Full Prison Sissy Transformation (1080p)

Clips4sale 1 week ago

Officer Mia Trains Larz and Amber Stark

63% 4K 0:11 / 40:25

Officer Mia Trains Larz and Amber Stark

Clips4sale 1 year ago

[1000] Teamwork Makes The Dreamwork 1000 Holes

74% HD 1:00 / 1:55:47

[1000] Teamwork Makes The Dreamwork 1000 Holes

Clips4sale 1 month ago

Slaves made to be human ashtrays for Goddesses | Black Nymphe

47% 0:26 / 7:04

Slaves made to be human ashtrays for Goddesses | Black Nymphe

Clips4sale 5 months ago

Misty captive handcuffed and chained perils - chained outside Part 2 *wmv*

73% HD 0:29 / 10:58

Misty captive handcuffed and chained perils - chained outside Part 2 *wmv*

Clips4sale 1 year ago

Mooin Witch - Maid Judith writhes on the spiky medieval witch's chair while her udders are treated with ice water melted hot wax clamps and tickling

61% 1:00 / 27:24

Mooin Witch - Maid Judith writhes on the spiky medieval witch's chair while her udders are treated with ice water melted hot wax clamps and tickling

Clips4sale 1 month ago

imprisoned in chastity

70% 0:31 / 6:32

imprisoned in chastity

Clips4sale 5 months ago

Captured Cumming Cop is Bound and Humiliated (MP4 Format)

61% 0:31 / 39:45

Captured Cumming Cop is Bound and Humiliated (MP4 Format)

Clips4sale 2 weeks ago

A court ordered judicial (Shot in 4K) Got to number 1 in the caning section in 22 hours!

66% 4K 0:56 / 33:20

A court ordered judicial (Shot in 4K) Got to number 1 in the caning section in 22 hours!

Clips4sale 2 weeks ago

Titslave Eva - 48 Hours in Tit Hell - Episode 11 - Full Clip - HD (mp4)

61% HD 0:11 / 39:36

Titslave Eva - 48 Hours in Tit Hell - Episode 11 - Full Clip - HD (mp4)

Clips4sale 2 years ago

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19,794 results found

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