Prison

RealWifeStories – Christina May – Cuck-held Without Bail
 24:43

RealWifeStories – Christina May – Cuck-held Without Bail

PornstarsLikeItBig – Georgie Lyall, Leigh Darby And Victoria Summers – The Doctor Part Three
 45:15

PornstarsLikeItBig – Georgie Lyall, Leigh Darby And Victoria Summers – The Doctor Part Three

RealWifeStories – Nina Elle – Jailhouse Cock
 36:37

RealWifeStories – Nina Elle – Jailhouse Cock

MoviePorn – Alexis Crystal – A New Hoe
 17:24

MoviePorn – Alexis Crystal – A New Hoe

HarmonyVision – Liza Del Sierra – Strung Out And Suspended – Fetish Prison Threeway
 35:58

HarmonyVision – Liza Del Sierra – Strung Out And Suspended – Fetish Prison Threeway

DevilsFilm – The Destruction Of Romi Rain (2016)
 01:35:49

DevilsFilm – The Destruction Of Romi Rain (2016)

HotAndMean – Lela Star And Molly Stewart – Wanted Fucked Or Alive: Part 1
 31:09

HotAndMean – Lela Star And Molly Stewart – Wanted Fucked Or Alive: Part 1

FakehubOriginals – Amber Deen And Sophie Anderson – Space Taxi: Bounty
 32:23

FakehubOriginals – Amber Deen And Sophie Anderson – Space Taxi: Bounty

Interracial Surrender 4
 02:45:45

Interracial Surrender 4

RealWifeStories – Asa Akira – Say Hi to your Husband for Me Part 3
 42:29

RealWifeStories – Asa Akira – Say Hi to your Husband for Me Part 3

Submissived – Kyra Rose – Military Sex Prisoner
 22:41

Submissived – Kyra Rose – Military Sex Prisoner

BlacksOnBlondes – Nicole Aria
 39:09

BlacksOnBlondes – Nicole Aria

TransAngels – Aspen Brooks And Jade Venus – Locked Up And Horned Up Part 2
 31:54

TransAngels – Aspen Brooks And Jade Venus – Locked Up And Horned Up Part 2

BigTitsInUniform – Katja Kassin – The Whore Prisoner
 28:29

BigTitsInUniform – Katja Kassin – The Whore Prisoner

DetentionGirls – Lilly Ford – Seducing The Admin
 32:55

DetentionGirls – Lilly Ford – Seducing The Admin

LilHumpers – Alexis Fawx – Lil Jailbird
 30:42

LilHumpers – Alexis Fawx – Lil Jailbird

PornstarsLikeItBig – Lexi Belle, Gia Dimarco, Christy Mack And Bonnie Rotten – Wonderland Part 2
 38:59

PornstarsLikeItBig – Lexi Belle, Gia Dimarco, Christy Mack And Bonnie Rotten – Wonderland Part 2

DeviantHardcore – Gina Valentina – Submissive latina Gina Valentina gets assfucked in a cage
 24:03

DeviantHardcore – Gina Valentina – Submissive latina Gina Valentina gets assfucked in a cage

HorrorPorn – The Beast From The Woods
 17:45

HorrorPorn – The Beast From The Woods

DPFanatics – Angie Koks – The Best Of The Corps
 30:08

DPFanatics – Angie Koks – The Best Of The Corps

BrazzersExxtra – She’s Gonna Cum! – The Best Of Female Orgasm
 01:31:07

BrazzersExxtra – She’s Gonna Cum! – The Best Of Female Orgasm

BigButtsLikeItBig – AJ Applegate – Escape From Asscatraz
 35:47

BigButtsLikeItBig – AJ Applegate – Escape From Asscatraz

DetentionGirls – Chanel Shortcake, Kenzie Reeves And Mackenzie Moss – Girl Power
 41:12

DetentionGirls – Chanel Shortcake, Kenzie Reeves And Mackenzie Moss – Girl Power

BrazzersExxtra – Ava Koxxx And Summer Brielle – I Hope You Brought Enough For Everyone
 31:46

BrazzersExxtra – Ava Koxxx And Summer Brielle – I Hope You Brought Enough For Everyone

MyDaughtersHotFriend – Charlotte Cross 26475

MyDaughtersHotFriend – Charlotte Cross 26475

HorrorPorn – Vinna Reed – Demonic Beauty
 16:31

HorrorPorn – Vinna Reed – Demonic Beauty

TransAngels – Kay Carter And Ariel Demure – Laying On The Lam
 40:49

TransAngels – Kay Carter And Ariel Demure – Laying On The Lam

DevilsFilm – Missy Martinez And Avi Love – Pros VS Cons
 30:42

DevilsFilm – Missy Martinez And Avi Love – Pros VS Cons

BrazzersExxtra – Lela Star – Wanted Fucked Or Alive: Part 2
 31:21

BrazzersExxtra – Lela Star – Wanted Fucked Or Alive: Part 2

Cucked – Luna Skye – Luna’s Hot Pussy Belongs To Her Ex
 24:51

Cucked – Luna Skye – Luna’s Hot Pussy Belongs To Her Ex

DPFanatics – Cindy Dollar – Prison DP
 34:39

DPFanatics – Cindy Dollar – Prison DP

PureTaboo – Angela White – Balance Of Power
 45:19

PureTaboo – Angela White – Balance Of Power

Private – Pirate Fetish Machine 14 – Theatre of Lust (2004)
 01:12:18

Private – Pirate Fetish Machine 14 – Theatre of Lust (2004)

DoctorAdventures – Roberta Gemma – Midnight Fuxpress
 33:56

DoctorAdventures – Roberta Gemma – Midnight Fuxpress

MyDirtyMaid – Samantha Bell – Big Booty Latina Maid Gets PIPED
 51:29

MyDirtyMaid – Samantha Bell – Big Booty Latina Maid Gets PIPED

Dorcel – A Novice Lawyer (2014)
 02:03:12

Dorcel – A Novice Lawyer (2014)

PornstarsLikeItBig – Audrey Bitoni – The Future Is Fucked
 29:49

PornstarsLikeItBig – Audrey Bitoni – The Future Is Fucked

DetentionGirls – Adira Allure, Jane Wilde And Mackenzie Moss – Saint Patrick’s Day Sex Party
 38:35

DetentionGirls – Adira Allure, Jane Wilde And Mackenzie Moss – Saint Patrick’s Day Sex Party

ZZSeries – Julia Ann – Lost In Brazzers Episode 2
 31:14

ZZSeries – Julia Ann – Lost In Brazzers Episode 2

TeensLikeItBig – Dani Daniels – Inmate In My Pussy
 38:38

TeensLikeItBig – Dani Daniels – Inmate In My Pussy

HotAndMean – Victoria Cakes And Clara Trinity – Fucking The Hitchhiker And The Jailbird Part 1
 26:43

HotAndMean – Victoria Cakes And Clara Trinity – Fucking The Hitchhiker And The Jailbird Part 1

Salieri – CKP – War In The Former Yugoslavia (1996)
 01:17:50

Salieri – CKP – War In The Former Yugoslavia (1996)

CumPerfection – Zeena Valvona – Get Out Of Jail Free
 10:21

CumPerfection – Zeena Valvona – Get Out Of Jail Free

MommyGotBoobs – Julia Ann – My Conjugal Stepmother
 36:34

MommyGotBoobs – Julia Ann – My Conjugal Stepmother

DetentionGirls – Natalia Nix – Sneaking Out
 32:00

DetentionGirls – Natalia Nix – Sneaking Out

DaughterSwap – Audrey Royal And Lilly Hall – The Pussy Before Prison Provision
 45:15

DaughterSwap – Audrey Royal And Lilly Hall – The Pussy Before Prison Provision

SpoofPorn – Karyn – Undercover Slut II: The Punishment
 36:05

SpoofPorn – Karyn – Undercover Slut II: The Punishment

HorrorPorn – Hell In Jail
 45:06

HorrorPorn – Hell In Jail

PornWorld – Dolly Diore And Olivia Jager – Jailhouse Tramps Hardcore Fucked by Guard
 37:32

PornWorld – Dolly Diore And Olivia Jager – Jailhouse Tramps Hardcore Fucked by Guard

EvilAngel – Sexploits (2021)
 04:05:53

EvilAngel – Sexploits (2021)

JamesDeen – Vannah Sterling – Vanna Sterling Sucks Two Dicks Before Getting Fucked
 32:10

JamesDeen – Vannah Sterling – Vanna Sterling Sucks Two Dicks Before Getting Fucked

PrettyDirty – Kenzie Taylor – Civil Commitment
 29:16

PrettyDirty – Kenzie Taylor – Civil Commitment

DPFanatics – Aletta Ocean – The Gutterman-Files
 30:35

DPFanatics – Aletta Ocean – The Gutterman-Files

GirlsWay – Jenna Sativa And Angela White – Panty Theft
 38:00

GirlsWay – Jenna Sativa And Angela White – Panty Theft

MissaX – Aiden Ashley And Vanna Bardot – A Killer On The Loose Part 1
 41:16

MissaX – Aiden Ashley And Vanna Bardot – A Killer On The Loose Part 1

MissaX – Jill Kassidy – Laura Part 3
 22:54

MissaX – Jill Kassidy – Laura Part 3

PureTaboo – Adriana Chechik And Vienna Rose – Booked
 54:10

PureTaboo – Adriana Chechik And Vienna Rose – Booked

BangbrosClips – Kailani Kai – Kailani Kai Fucks Inmate
 35:33

BangbrosClips – Kailani Kai – Kailani Kai Fucks Inmate

BigButtsLikeItBig – Mandy Muse – Free My Ass And The Pleasure Will Follow
 32:14

BigButtsLikeItBig – Mandy Muse – Free My Ass And The Pleasure Will Follow

Vixen – Scarlit Scandal, Cards Dealt

Vixen – Scarlit Scandal, Cards Dealt

SexAndSubmission – Penny Pax – Pennys Anal Embezzlement
 01:00:42

SexAndSubmission – Penny Pax – Pennys Anal Embezzlement

DigitalPlayground – Misha Cross And Jessa Rhodes – Rawhide S02
 29:37

DigitalPlayground – Misha Cross And Jessa Rhodes – Rawhide S02

BrazzersExxtra – Victoria Cakes And Clara Trinity – Fucking The Hitchhiker And The Jailbird Part 2
 31:03

BrazzersExxtra – Victoria Cakes And Clara Trinity – Fucking The Hitchhiker And The Jailbird Part 2

CuckoldSessions – Kay Lovely
 31:06

CuckoldSessions – Kay Lovely