1 year ago
7:05

PornHub

New inmate Marica Hase meets prison bully Lily

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Pornstars: Lily Cade

1 year ago
1:19:37

VideoSection

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1 year ago
7:57

BravoTeens

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3 years ago
5:51

Txxx

Haruka Aizawa in Private Investigator Haruka Fucks In Prison - CosplayInJapan

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2 years ago
6:45

JizzBunker

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10 months ago
8:00

HellPorno

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Pornstars: Peaches

3 years ago
1:10:31

TubePornClassic

Special Hostess

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4 months ago
12:00

PornGo

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Pornstars: Aria Alexander, Jasmine Webb

2 years ago
7:00

HotMovs

Darcia Lee & Harmony Reigns & Stirling Cooper in Prison Heat - FakehubOriginals

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Pornstars: Harmony Reigns

3 months ago
34:24

VideoSection

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1 year ago
7:58

BravoTube

Ebony whore Misty Stone blows, rides and gets a facial in prison

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8 months ago
15:10

PornHub

4K! Erica Lauren: MILF Conjugal FJ

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Pornstars: Erica Lauren

5 months ago
14:00

PornHub

ScamAngels - Abella Danger And Zoe Monroe PAWG American Sluts Fuck Prison Guard

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5 years ago
7:00

TubeDupe

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3 years ago
5:00

BravoTube

Three inviting prisoners including Dasha have hot lesbian sex

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Pornstars: Dasha

2 years ago
5:12

PornGem

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1 year ago
5:19

Txxx

Lolly and Taylor Mess Diapers in Prison Cell

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9 months ago
8:12

VideoSection

big knocker Teen Steals From Store Fucks Officer To Avoid prison

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3 years ago
19:55

BravoTube

This inmate needs a full inspection, and Angelika Black is just the CO to do it.

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Pornstars: Black Angelika

3 months ago
9:50

VideoSection

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4 years ago
7:00

SexVid

A blonde hottie is getting fucked really hard in the prison

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Pornstars: Johnny Sins, Nina Elle

2 years ago
9:58

AnyPorn

Busty Romi Rain gets fucked in the jail while her big tits bounce

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2 years ago
7:00

XoZilla

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Pornstars: Katie Morgan

1 year ago
7:30

YourLust

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2 years ago
25:23

JizzBunker

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9 months ago
8:08

HDSex

concerned teen Shoplifter plows Security To Avoid Prison

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5 years ago
38:39

Vivud

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7 years ago
4:00

FlyFlv

Life In The Women Prison

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Pornstars: Brandy Aniston, Chanel Preston, Jynx Maze, Vicki Chase

2 years ago
27:10

JizzBunker

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1 year ago
3:54

PornHub

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2 years ago
3:34

JizzBunker

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10 months ago
8:10

HDSex

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5 years ago
5:59

AnyPorn

Lawyer lady dominates her lesbian client in prison

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4 years ago
7:00

PornID

A brunette that loves anal sex is getting penetrated by a convict

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Pornstars: Danny D

5 months ago
5:02

PornHub

Lesbian In Prison Masturbating And Reaches Orgasm

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1 year ago
8:10

HDSex

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4 years ago
3:03

PornWatchers

Prison Warden Picks A Plaything

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Pornstars: Diamond Jackson

2 years ago
7:39

HDZog

Security Cop Fucks Busted Teen Shoplifter Desperate To Avoid Prison

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2 years ago
13:42

JizzBunker

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2 years ago
4:58

BravoTeens

Busty pornstar in fishnets Carly Parker sprayed with cum at prison

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Pornstars: Carly Parker

1 year ago
20:27

xHamster

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1 year ago
7:59

BravoTube

Perfect slut Audrey Bitoni obeys every sexy command and swallows cum

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Pornstars: Audrey Bitoni

3 years ago
14:24

PornHub

prison break - Scene 2

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11 months ago
37:11

PornTry

Prison Cell Control - New Face Humiliated And Ass Fucked

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3 years ago
6:13

SexVid

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Pornstars: Dana Vespoli

2 years ago
7:00

PornID

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5 months ago
5:37

SunPorno

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5 years ago
7:00

AnyPorn

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2 years ago
5:13

XXXDan

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10 years ago
5:02

PornoXO

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2 years ago
8:02

uiPorn

Uber-Cute Teenage Drills Security To Avoid Prison

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4 months ago
10:55

PornHub

Prison Futa Makes You Her Bitch Again

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1 year ago
10:01

uiPorn

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6 years ago
4:00

TubeDupe

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

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1 year ago
3:55

PornHub

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2 years ago
7:58

BravoTube

Ana Foxxx's amazing body pounded hard by a handsome man

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Pornstars: Ana Foxxx

2 years ago
10:25

SunPorno

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7 years ago
7:00

HellPorno

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Pornstars: Alektra Blue, Manuel Ferrara

3 years ago
8:00

AnyPorn

Dominica Phoenix and Christina Shine crave to be fucked by hot men

Categories: group sex, hardcore, orgy, pornstar, prison, uniform

1 year ago
18:45

FetishPapa

Lez chastity belted Slave in Prison

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2 years ago
31:12

PornHub

Taboo, Bro just got out prison

Categories: amateur, creampie, female orgasm, fetish, prison, taboo

4 years ago
1:20

xHamster

Mistress lets put slave in prison, to lick pussy

Categories: bdsm, japanese, licking, mistress, prison, pussy, slave

2 years ago
6:58

BravoTeens

Akane Aoi makes out with a neighbor while he fucks her hard

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Pornstars: Aoi

9 years ago
8:00

HellPorno

Cop busts him and gets fucked

Categories: anal, big cock, blowjob, brunette, cop, prison, pussy, shaved, titty fuck, uniform

8 years ago
10:01

Ah Me

Redhead Girl On Her Knees Sucking Jailers Cock Swallowing Behind The Bars

Categories: asian, blowjob, cum swallowing, dick, knees, prison, redhead, sucking

2 years ago
5:56

ZedPorn

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Categories: babe, big ass, big tits, brunette, couple, fake tits, high heels, licking, pussy, redhead

10 years ago
5:58

YourLust

Jessica visits the boys in prison

Categories: 3some, anal, backstage, big tits, blonde, boy, double penetration, prison, uniform

3 years ago
7:58

BravoTube

Splendid reverse cowgirl cock exlpoiting with his babe Isis Love

Categories: babe, couple, cowgirl, dick, milf, pornstar, prison, uniform

Pornstars: Isis Love

3 years ago
38:07

XXXDan

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Categories: big ass, casting, granny, milf, pov, prison

3 years ago
7:30

YourLust

Gorgeous cop Angelica Black fucks a convict in the prison cell

Categories: beauty, brunette, cop, cowgirl, cute, gorgeous, hardcore, pornstar, riding, slut

Pornstars: Angelica Black

3 years ago
7:32

PornoMovies

Milf Amber Lynn Bach Riding Black Cock In Prison

Categories: big cock, big tits, black, blonde, blowjob, dick, milf, oral, pornstar, riding

Pornstars: Amber Lynn Bach

4 years ago
7:00

AnySex

Sex-starved lesbian babe Stella Cox fucks arrested chick and makes her orgasm

Categories: babe, big tits, brunette, fingering, licking, lingerie, pornstar, pussy, striptease, uniform

Pornstars: Stella Cox

3 years ago
5:36

XXXDan

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Categories: bbw, big cock, big tits, hardcore, interracial, milf, prison, reality, uniform

7 years ago
4:56

Ah Me

Horny Amy Brooke Sucks On This T...

Categories: 69, babe, big tits, pornstar, prison, sucking

Pornstars: Amy Brooke

10 years ago
5:03

PornoXO

Cock jerking in a prison

Categories: cumshot, dick, handjob, japanese, jerking, prison

7 years ago
8:47

Ah Me

Jail Lesbian Domination

Categories: domination, jail, lesbian, lezdom, prison, teen (18+)

2 years ago
6:19

PornHub

Christina Carter brought to prison 2

Categories: ass, babe, bdsm, big tits, bondage, brunette, nude, pornstar, prison, pussy

Pornstars: Christina Carter

2 years ago
8:00

PornID

Bald masseur makes sure stunning inmate is in good mood

Categories: big tits, brunette, hairless, latina, massage, pornstar, pussy, slut, smoking, squirt

Pornstars: Johnny Sins

4 years ago
6:00

HellPorno

Aletta Ocean sucks and fucks heavy cock while imprisoned

Categories: big tits, blowjob, brunette, dick, doggystyle, hd, milf, moaning, pornstar, sucking

Pornstars: Aletta Ocean

3 years ago
7:58

FlyFlv

Big Tits Behind Bars

Categories: big cock, big tits, blowjob, latina, milf, pornstar, prison, rimjob, sucking, tattoo

Pornstars: Isis Love

5 years ago
1:08

AnySex

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Categories: big tits, brunette, erotic, flashing, funny, kinky, panties, shaved, tanned, teen (18+)

14 years ago
6:05

PornHub

Prison Sex

Categories: big black cock, big tits, blonde, blowjob, interracial, monster cock, pornstar, prison, skinny

Pornstars: Brooke Banner

5 years ago
6:52

FlyFlv

Busty Nina Visits Friend In Jail

Categories: babe, big tits, blonde, friend, from behind, jail, pornstar, prison, standing, undressing

Pornstars: Nina Elle

4 years ago
7:00

GotPorn

Shyla stylez anal police xxx BreakIn Attempt Suspect has to plumb his way out of prison

Categories: 3some, anal, blonde, cop, interracial, pornstar, prison, riding, teen (18+), white

Pornstars: Shyla Stylez

4 years ago
6:58

BravoTeens

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Categories: asian, couple, fishnet, handjob, hardcore, moaning, natural tits, shaved, stockings, thong

8 years ago
9:54

Ah Me

Chihiro Hara from idol69tied up in jail and gets a sex train

Categories: asian, hardcore, jail, prison, tied up, train

4 years ago
6:00

TubeDupe

Jailhouse Fuck Three

Categories: babe, doctor, glasses, hardcore, milf, nurse, pornstar, prison, reality, redhead

7 months ago
17:31

PornHub

#7 where it all began - Miru had to fuck him for my safety

Categories: amateur, anime, asian, ass, babe, big ass, big tits, cartoon, prison

5 years ago
5:21

JizzBunker

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Categories: asian, babe, bukkake, cumshot, english, facial, first time, gangbang, japanese, uncensored

4 years ago
5:52

XBabe

Imprisoned teens hard fucked before being released

Categories: 3some, babe, ball licking, blowjob, cowgirl, cum in mouth, cumshot, doggystyle, ffm, hardcore

Pornstars: Peaches

4 years ago
5:00

AnyPorn

Three cunt lovers get naked and have a lot of fun together

Categories: bra, cunt, fake tits, fingering, licking, nude, pornstar, pussy, stockings, strap-on

7 years ago
9:00

FlyFlv

Japanese Female Army Privates Are Captured

Categories: army, babe, big tits, bondage, brunette, cunt, hairy, japanese, legs, spreading

6 years ago
6:30

AnySex

Hot like hell caged sweeties perform steamy BJ to cute brutal boys

Categories: big tits, blonde, blowjob, brunette, cumshot, cute, facial, group sex, milf, pornstar

7 years ago
6:00

FlyFlv

Caged Girls Know Their Place

Categories: bdsm, blowjob, brunette, cage, domination, humiliation, milf, prison

1 year ago
7:41

PornHub

MyDirtyHobby - Teen escapes prison after caught masturbating in public

Categories: amateur, big natural tits, big tits, blonde, blowjob, caught, creampie, german, masturbation, outdoor

4 years ago
7:59

TubeDupe

Nasty Blonde Bangs Dude in Uniform

Categories: ass, babe, blonde, dick, face fucking, fantasy, hardcore, long hair, masturbation, smoking

3 years ago
4:04

PornHub

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Categories: 3some, ass, bbw, big ass, big tits, chubby, compilation, ebony, fat, fetish

9 months ago
7:59

PornHat

So Busted II

Categories: bed sex, blonde, close up, gaping hole, high heels, perfect body, pornstar, posing, prison, tease

Pornstars: Kylee Nash

6 years ago
5:00

TubeON

Prison nurse Gianna Michaels dominating a helpless male inmate

Categories: big tits, brunette, femdom, fetish, lingerie, nurse, pornstar, prison, stockings

Pornstars: Gianna Michaels

1 year ago
8:23

PornHub

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Categories: american, ass, bdsm, bondage, brunette, feet, jail, kinky, latina, nude

2 months ago
7:08

HDSex

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Categories: bondage, handcuffed, prison

8 months ago
10:32

PornHub

Fashion Business: Horny Prisoners And A Sexy Girl-Ep 37

Categories: 3d, amateur, business woman, cartoon, erotic, funny, game, jail, milf, mom

2 months ago
37:00

UPornia

Lisa Lipps And Daphne Rosen - Nvp Prison Conflict 2

Categories: big tits, brunette, lesbian, pornstar, prison, retro, vintage

Pornstars: Daphne Rosen, Lisa Lipps

8 months ago
8:22

VideoSection

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Categories: bdsm, bondage, british, cage, caning, prison, punishment, raunchy, spanking, whip

9 months ago
10:00

PornHat

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Categories: babe, blowjob, brunette, cowgirl, cunt, deep throat, doggystyle, handjob, hardcore, legs

9 months ago
10:00

PornHat

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Categories: 3some, ass, blonde, blowjob, cowgirl, doggystyle, double penetration, handjob, legs, missionary

9 months ago
7:55

HDSex

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Categories: big cock, blowjob, jail, prison, teen (18+)

8 months ago
3:45

PornHub

Tyron's bare back whipping at prison 0208

Categories: amateur, barebacking, caning, fetish, kinky, prison, slave, spanking, whip

1 year ago
3:56

PornHub

Chelsy's ass whipping at prison 2502

Categories: amateur, ass, caning, english, fetish, kinky, prison, spanking, whip

9 months ago
7:59

OK.XXX

Good-looking busty Kylee Nash shows off her nippleless boobies

Categories: babe, bed sex, big ass, big tits, blonde, close up, fingering, gaping hole, handjob, high heels

Pornstars: Kylee Nash

8 months ago
9:59

PornHat

The Future Is Fucked

Categories: blowjob, close up, cowgirl, fake tits, handjob, legs, milf, missionary, model, oral

Pornstars: Audrey Bitoni

8 months ago
6:10

VipTube

Brunette sucks and rides officers big cock to evade prison

Categories: big cock, blowjob, brunette, cop, hardcore, hd, prison, small tits, sucking, teen (18+)

1 year ago
8:11

HDSex

lesbian Cop tells arrested chick to stretch her toes and cop checks every toe

Categories: chained, cop, feet, handcuffed, lesbian, prison, toes

45 days ago
12:58

HDSex

Hotwife, gonzo, three-ways

Categories: 3some, cage, cuckold, prison

8 months ago
10:00

OK.XXX

Very cute busty angel Sofia Lee jumps on a pretty massive dick

Categories: bbw, big ass, big cock, big tits, blowjob, brunette, caught, close up, cowgirl, cute

1 year ago
12:00

PornHub

Deviant Hardcore - Dom Alix Lynx & Karlee Grey

Categories: ass, big tits, fake tits, femdom, fetish, hardcore, lesbian, natural tits, piercing, pornstar

Pornstars: Karlee Grey

2 years ago
3:24

Txxx

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Categories: bdsm, fetish, prison, redhead, spanking

1 year ago
2:47

TheyAreHuge

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2 years ago
4:35

Txxx

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Categories: femdom, fetish, prison, slut, strap-on

10 months ago
14:17

xHamster

Kathy Willets and Ron Jeremy - Naked Scandal #2 (1996)

Categories: big tits, blonde, cop, hardcore, mature, milf, nude, pornstar, slut, vintage

Pornstars: Kathy Willets, Ron Jeremy