Real Prison (2,251)

Prisoner of Pleasure: Anal Trio

HD 0:10 / 15:01

Prisoner of Pleasure: Anal Trio

LoyalFans 1 year ago

Total Sexual Humiliation of Cucky Slut!

76% HD 1:01 / 23:08

Total Sexual Humiliation of Cucky Slut!

FapHouse 10 months ago

The Prisoner and the Guard: Fucked in the Basement

53% HD 1:01 / 14:41

The Prisoner and the Guard: Fucked in the Basement

FapHouse 1 year ago

Double Imprisonment 1

52% HD 1:01 / 9:22

Double Imprisonment 1

FapHouse 2 years ago

Hentai - Aliens Fuck In Jail - Emiri Momota, Momota Emiri And Real Life

Hentai - Aliens Fuck In Jail - Emiri Momota, Momota Emiri And Real Life

FuJAV 2 months ago

A Hard Caning for Three

57% 1:01 / 14:59

A Hard Caning for Three

FapHouse 3 months ago

Still in Chastity!! Crotchless Pantyhose!

73% HD 1:01 / 18:06

Still in Chastity!! Crotchless Pantyhose!

FapHouse 9 months ago

You are tied prisoner in "Milking Factory"

69% HD 1:01 / 18:45

You are tied prisoner in "Milking Factory"

FapHouse 3 years ago

Josefine Mutzenbacher part 3 duke video

50% 0:39 / 1:14:08

Josefine Mutzenbacher part 3 duke video

FapHouse 5 years ago

The Perverted Prison Guard with Sandy

64% HD 1:01 / 29:02

The Perverted Prison Guard with Sandy

FapHouse 5 years ago

imani seduction prison sex w/ rome major

57% HD 0:30 / 37:02

imani seduction prison sex w/ rome major

PornBox 10 months ago

Cop Fucks Whore at the Police Station - Max Betancur & Shairapsychosex

60% HD 0:39 / 14:22

Cop Fucks Whore at the Police Station - Max Betancur & Shairapsychosex

FapHouse 8 months ago

Real fem dom extreme 2/2

64% HD 1:01 / 10:49

Real fem dom extreme 2/2

FapHouse 4 years ago

cum beard

Fapplr 2 years ago

The Prisoner and the Guard: Fucked in the Basement

The Prisoner and the Guard: Fucked in the Basement

xHamster 4 months ago

Spanked Convict

50% HD 1:01 / 9:17

Spanked Convict

FapHouse 3 months ago

Prisoner at the farm 3

65% HD 1:01 / 9:37

Prisoner at the farm 3

FapHouse 8 years ago

Marie Gets Fucked by Prisoner

Marie Gets Fucked by Prisoner

xHamster 6 months ago

Josefine Mutzenbacher part 3 duke video

43% 1:01 / 1:14:08

Josefine Mutzenbacher part 3 duke video

FapHouse 5 years ago

Total Sexual Humiliation of Cucky Slut!

73% HD 0:39 / 23:08

Total Sexual Humiliation of Cucky Slut!

FapHouse 10 months ago

The Officer

55% HD 1:01 / 11:02

FapHouse 3 months ago

Epic moment from "Beautiful Latina deepthroat blowjob expert"

Epic moment from "Beautiful Latina deepthroat blowjob expert"

xHamster 6 months ago

Cop Fucks Whore at the Police Station - Max Betancur & Shairapsychosex

54% HD 1:01 / 14:22

Cop Fucks Whore at the Police Station - Max Betancur & Shairapsychosex

FapHouse 8 months ago

Ex-husband Comes Home From Prison and Fucks Cheating Wife

Ex-husband Comes Home From Prison and Fucks Cheating Wife

xHamster 2 weeks ago

The Guy Escaped From Prison and Punished the Judge's Wife. Dominating a Pet Girl

67% HD 0:39 / 32:19

The Guy Escaped From Prison and Punished the Judge's Wife. Dominating a Pet Girl

FapHouse 2 years ago

Slave Girl Earns a Bed

62% HD 0:39 / 1:18:24

Slave Girl Earns a Bed

FapHouse 6 months ago

The Prisoner and the Guard: Fucked in the Basement

HD 0:39 / 14:41

The Prisoner and the Guard: Fucked in the Basement

FapHouse 1 year ago

Ultimate prison sadism 631

Ultimate prison sadism 631

xHamster 2 months ago

Dominatrix Fucks Her Slave’s Strap-On While His Cock Is Locked

Dominatrix Fucks Her Slave’s Strap-On While His Cock Is Locked

Clips4sale 5 months ago

Blowpipe arrows and merciless single tail french-hungarian sadism - Mistress Zeida and Dame Luciferia

Blowpipe arrows and merciless single tail french-hungarian sadism - Mistress Zeida and Dame Luciferia

xHamster 1 year ago

Dungeon Slaveslut 2

74% HD 0:39 / 10:47

Dungeon Slaveslut 2

FapHouse 3 months ago

Zeida and Mahogany whipping the short slave and the cameraman slave

Zeida and Mahogany whipping the short slave and the cameraman slave

xHamster 10 months ago

Succubus VS Knight

HD 0:43 / 37:18

Succubus VS Knight

Clips4sale 2 days ago

SISSY PRISON - Dental Terror V *wmv*

57% 4K 0:30 / 15:44

SISSY PRISON - Dental Terror V *wmv*

Clips4sale 3 days ago

Caning day

58% HD 0:10 / 11:16

LoyalFans 1 year ago

Zeida and Zara flogging his back to pieces

Zeida and Zara flogging his back to pieces

LoyalFans 1 year ago

Female Prison Guard is fucking this alternative girl in prison/ Divine Eve

Female Prison Guard is fucking this alternative girl in prison/ Divine Eve

Juicexxx 1 month ago

Frontal breast whipping - Extreme LEZDOM - Lesbian Domination NEW slave girl

Frontal breast whipping - Extreme LEZDOM - Lesbian Domination NEW slave girl

xHamster 1 year ago

Big cock sucking petite pussy fucking in the prison

61% HD 0:39 / 24:57

Big cock sucking petite pussy fucking in the prison

FapHouse 3 years ago

cum beard

ClubSweethearts 2 years ago

prison guard and doctor ass fucking an inmate

prison guard and doctor ass fucking an inmate

AnalVids 1 year ago

Night pony training contest at Dracula Femdom Castle

Night pony training contest at Dracula Femdom Castle

LoyalFans 1 month ago

Ultimate prison sadism

63% HD 0:10 / 5:55

Ultimate prison sadism

LoyalFans 2 months ago

MISTRESS XENIA DARK - THE PLEASURE OF THE WHIP - PART 1

54% HD 0:10 / 15:45

MISTRESS XENIA DARK - THE PLEASURE OF THE WHIP - PART 1

LoyalFans 1 year ago

The Prisoner Punishment Caning and Fucking

HD 0:38 / 11:20

The Prisoner Punishment Caning and Fucking

Clips4sale 1 year ago

Lady In Red (HD 720p)

Lady In Red (HD 720p)

Clips4sale 1 week ago

SISSY PRISON - Dental Terror

66% 4K 0:35 / 19:17

SISSY PRISON - Dental Terror

Clips4sale 3 months ago

a busty prisoner to fuck

a busty prisoner to fuck

PornBox 1 year ago

Domestic Servitude - Part 1 **MOV**

4K 0:38 / 10:33

Domestic Servitude - Part 1 **MOV**

Clips4sale 2 years ago

Man Catcher - tease and torment *MOV*

4K 0:30 / 14:05

Man Catcher - tease and torment *MOV*

Clips4sale 2 months ago

threesome with the beautiful prisoner: he fucks her in the ass and she licks her pussy

threesome with the beautiful prisoner: he fucks her in the ass and she licks her pussy

PornBox 1 year ago

Her Prisoner - Interrogated & Trained FULL movie *MOV*

4K 0:36 / 1:30:41

Her Prisoner - Interrogated & Trained FULL movie *MOV*

Clips4sale 3 weeks ago

Extreme waxing the bald head of the prisoner - flame drips on his head - Mistress Roberta OWK and Mistress Zeida

Extreme waxing the bald head of the prisoner - flame drips on his head - Mistress Roberta OWK and Mistress Zeida

xHamster 1 year ago

female prison guards (full movie)

female prison guards (full movie)

PornBox 1 year ago

Husband and Wife Injoy in Da Village Creem

Husband and Wife Injoy in Da Village Creem

FapHouse 3 weeks ago

Aztec torment device - Restrained in the medieval stock

Aztec torment device - Restrained in the medieval stock

Hotel luxxxuria English SC 02 hot lustful sex

Hotel luxxxuria English SC 02 hot lustful sex

FapHouse 2 years ago

My Policeman Friend Searches Every Hole to Take Me to Prison

65% 0:39 / 20:35

My Policeman Friend Searches Every Hole to Take Me to Prison

FapHouse 10 months ago

Hard flogging trio at the swimingpool

Hard flogging trio at the swimingpool

xHamster 1 year ago

Riding crop bastinado HAREM - Mistresses and Master

HD 0:10 / 10:03

Riding crop bastinado HAREM - Mistresses and Master

LoyalFans 3 days ago

prison sluts cassie young and audrey bitoni get plowed

prison sluts cassie young and audrey bitoni get plowed

PornBox 1 year ago

I Bail My Step Sis Out and She Lets Me Fuck - Serena Sterling

HD 1:01 / 38:23

I Bail My Step Sis Out and She Lets Me Fuck - Serena Sterling

FapHouse 1 year ago

The dangerus inmate Gaia transfered in maximum security jail

The dangerus inmate Gaia transfered in maximum security jail

Clips4sale 2 weeks ago

Hot waxing the bald head of the prisoner - Mistress Zeida DFC and Mistress Roberta OWK - Hot drips like my sadistic mind

Hot waxing the bald head of the prisoner - Mistress Zeida DFC and Mistress Roberta OWK - Hot drips like my sadistic mind

xHamster 1 year ago

Prisoner #28 at the Hidden Turture Farm II - Public Shower in the Cage

62% 0:18 / 12:14

Prisoner #28 at the Hidden Turture Farm II - Public Shower in the Cage

Clips4sale 2 years ago

He Asked To Be A Prisoner - Full, Uncut Edition

65% 0:11 / 2:57:09

He Asked To Be A Prisoner - Full, Uncut Edition

Clips4sale 3 years ago

sluts swallow a cum

HD 0:30 / 1:08:22

sluts swallow a cum

PornBox 2 years ago

Busty Nikki fucked in nature

62% HD 0:12 / 23:15

Busty Nikki fucked in nature

AdultPrime 9 years ago

Extreme Vintage Sex of Real Sluts Ass Fucked Hard and Cum in Mouth

Extreme Vintage Sex of Real Sluts Ass Fucked Hard and Cum in Mouth

xHamster 9 months ago

prison deal

HD 0:30 / 26:55

AnalVids 1 year ago

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

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

Clips4sale 3 years ago

Younger and Stronger (I)

71% 0:30 / 15:17

Younger and Stronger (I)

Clips4sale 1 year ago

”Real Life Hentai - Aliens fuck Emiri Momota in prison”

”Real Life Hentai - Aliens fuck Emiri Momota in prison”

TransHero 1 month ago

Slender Sylph Catherine Sterling is Strung Up, Slapped, Squeezed, & Stimulated for Steel Bound Orgasms Delivered by Ben! HD MP4 File Format

HD 0:30 / 15:48

Slender Sylph Catherine Sterling is Strung Up, Slapped, Squeezed, & Stimulated for Steel Bound Orgasms Delivered by Ben! HD MP4 File Format

Clips4sale 2 months ago

Italian - Hungarian Prison Guards in the Castle

Italian - Hungarian Prison Guards in the Castle

LoyalFans 1 week ago

Captivating moment from "Dominatrix Mistress Aprils Game Show"

Captivating moment from "Dominatrix Mistress Aprils Game Show"

xHamster 6 months ago

Nici Dee ass whipping - 1606

61% 0:11 / 4:31

Nici Dee ass whipping - 1606

Clips4sale 3 years ago

Slave Girl Earns a Bed

65% HD 0:39 / 1:18:24

Slave Girl Earns a Bed

FapHouse 6 months ago

busty bdsm cop alisha martinika lets stud loose for anal destruction gp2525

62% HD 1:06 / 1:03:50

busty bdsm cop alisha martinika lets stud loose for anal destruction gp2525

PornBox 3 years ago

brunettes with big boobs fuck and cum swallow

52% HD 0:30 / 1:03:08

brunettes with big boobs fuck and cum swallow

AnalVids 2 years ago

Kapri Styles African American Goddess

65% HD 0:39 / 16:13

Kapri Styles African American Goddess

FapHouse 3 weeks ago

dp dick ramming gets busty slut zlata shine out of jail for free gp2436

dp dick ramming gets busty slut zlata shine out of jail for free gp2436

SukaPorn 2 years ago

SISSY PRISON Punishment Table 3

57% 4K 0:45 / 14:54

SISSY PRISON Punishment Table 3

Clips4sale 1 month ago

WIFE TERROR - PRISONER CONDITIONING 1

4K 0:37 / 15:40

WIFE TERROR - PRISONER CONDITIONING 1

Clips4sale 23 hours ago

Hotel LuXXXuria Italian SC 02 very hot scene

57% HD 1:01 / 11:22

Hotel LuXXXuria Italian SC 02 very hot scene

FapHouse 2 years ago

two perfect sluts, jenny hard and mademoiselle justine share a good military cock

two perfect sluts, jenny hard and mademoiselle justine share a good military cock

SukaPorn 1 year ago

Chained by the Neck - Elise Graves and Heavy - Inmate Elise is locked into a heavy metal collar suspended by chains inside a prison cell with a creepy sheriff looking after her

65% HD 0:58 / 23:45

Chained by the Neck - Elise Graves and Heavy - Inmate Elise is locked into a heavy metal collar suspended by chains inside a prison cell with a creepy sheriff looking after her

Clips4sale 1 year ago

Ballbusting initialization - head in the toilet box - Zeida BDSM Queen of Transylvania

Ballbusting initialization - head in the toilet box - Zeida BDSM Queen of Transylvania

xHamster 9 months ago

Man Catcher Part 3 *wmv*

4K 0:27 / 11:04

Man Catcher Part 3 *wmv*

Clips4sale 2 months ago

Succubus VS Knight

HD 0:10 / 37:19

Succubus VS Knight

LoyalFans 2 days ago

The Feminatrix Files: Useful As My Food - Starring Mistress An Li

HD 0:10 / 12:22

The Feminatrix Files: Useful As My Food - Starring Mistress An Li

LoyalFans 3 years ago

my dream was to give it to a prisoner in handcuffs at the police. finally done it - carol fenix and oscar luz

HD 0:30 / 1:00:24

my dream was to give it to a prisoner in handcuffs at the police. finally done it - carol fenix and oscar luz

PornBox 3 years ago

Caprice paddle - 2112

Caprice paddle - 2112

Clips4sale 4 years ago

Have My Pussy For Being Goodie

Have My Pussy For Being Goodie

MilfFox 11 years ago

Ultimate prison sadism 631

Ultimate prison sadism 631

Amateur8 2 months ago

big tits milf fuck by huge cock

60% HD 0:30 / 1:14:21

big tits milf fuck by huge cock

PornBox 1 year ago

Restrained CBT - Needles in his balls and tongue

Restrained CBT - Needles in his balls and tongue

Hill Street Blacks 2 9/4/2014

50% 0:12 / 1:36:09

Hill Street Blacks 2 9/4/2014

AdultPrime 10 years ago

Extreme single tail and flogging distruction

58% HD 0:10 / 9:31

Extreme single tail and flogging distruction

LoyalFans 1 year ago

Sexy Cuffed Girl in Restraints with Big Natural Tits Massages Her Pussy and Ass with a Huge Black Cock

55% HD 0:39 / 11:23

Sexy Cuffed Girl in Restraints with Big Natural Tits Massages Her Pussy and Ass with a Huge Black Cock

FapHouse 2 years ago

The Perverted Prison Guard

HD 1:01 / 20:24

The Perverted Prison Guard

FapHouse 5 years ago

Real FemDom Extreme 2/2

HD 0:10 / 10:49

Real FemDom Extreme 2/2

LoyalFans 3 years ago

Collared and Caged *wmv*

60% 4K 0:20 / 11:54

Collared and Caged *wmv*

Clips4sale 2 weeks ago

Prisoner #27 returns for imprisonment - ENTIRE

HD 0:10 / 51:30

Prisoner #27 returns for imprisonment - ENTIRE

LoyalFans 5 months ago

VR girlfriend body swap

59% HD 0:59 / 23:15

VR girlfriend body swap

Clips4sale 1 year ago

brunettes with big boobs fuck and cum swallow

51% HD 0:30 / 1:03:08

brunettes with big boobs fuck and cum swallow

PornBox 2 years ago

The secretaries Gaia and Luna arrested in a parking - Part 1

The secretaries Gaia and Luna arrested in a parking - Part 1

Clips4sale 1 month ago

Retribution Part 35 *MOV*

4K 0:20 / 17:12

Retribution Part 35 *MOV*

Clips4sale 1 week ago

Gym Pervs Punishment Giantess Fetish

HD 0:39 / 25:31

Gym Pervs Punishment Giantess Fetish

FapHouse 1 month ago

Real Imprisonment 02 - 24h - Chapter TWO B - HDmp4

Real Imprisonment 02 - 24h - Chapter TWO B - HDmp4

Clips4sale 3 years ago

Busty Nikki fucked in nature

65% HD 0:12 / 23:15

Busty Nikki fucked in nature

ClubSweethearts 9 years ago

Retribution Part 19 *MOV*

4K 0:24 / 15:23

Retribution Part 19 *MOV*

Clips4sale 1 month ago

prison break - anal plugged escapee

HD 0:30 / 27:51

prison break - anal plugged escapee

AnalVids 1 year ago

Behind the scenes

57% HD 0:12 / 3:19

Behind the scenes

AdultPrime 9 years ago

SISSY PRISON - Dental Terror II *MOV*

65% 4K 0:54 / 15:06

SISSY PRISON - Dental Terror II *MOV*

Clips4sale 3 months ago

SISSY PRISON - SURGERY Part 1 *wmv*

4K 0:45 / 15:14

SISSY PRISON - SURGERY Part 1 *wmv*

Clips4sale 1 day ago

MISS CHEYENNE - SADISTIC PUNISHMENT OF AN EMASCIATED PRISONER

53% HD 0:10 / 17:30

MISS CHEYENNE - SADISTIC PUNISHMENT OF AN EMASCIATED PRISONER

LoyalFans 4 years ago

asia d argento: a warder fucks her in the ass while the other watches

65% HD 0:30 / 10:48

asia d argento: a warder fucks her in the ass while the other watches

AnalVids 1 year ago

Whiteboi Shrink Training

62% HD 0:10 / 7:51

Whiteboi Shrink Training

LoyalFans 9 months ago

big tits milf fuck by huge cock

59% HD 0:30 / 1:14:21

big tits milf fuck by huge cock

AnalVids 1 year ago

1 2 3 4 5

2,251 results found

Narrow your search

real prison guard

Categories Pornstars

Categories Pornstars

Legal

Terms of Service Privacy Statement Statement of Responsibility Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

Parents

Shortporn.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Shortporn.com. All rights reserved.