Warden

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The Role Reversal Game

Simone Sonay is our super-sexy Cougar jail..

Added: 2025-02-01 Rating: n/a

The Warden’s Tramp

The prison Warden enjoys it raunchy and harsh..

Added: 2025-01-14 Rating: n/a

Foxy Sweetie Has Some Tough Fuckin Job

The Yr 2021. The world has been overrun with..

Added: 2025-01-14 Rating: n/a

Assullum cockslut

A young inmate is trying to stash from the..

Added: 2025-01-13 Rating: n/a

Fist Fucking The Warden

Welcome Cougar starlet Anjanette Astoria to..

Added: 2025-01-12 Rating: n/a

The significance of collective values house a strenuous bond

In part 3 Bruno has Tony take Anna Belle on a..

Added: 2025-01-06 Rating: n/a

The magic of miranda

In part 3 Bruno has Tony take Anna Belle on a..

Added: 2025-01-03 Rating: n/a

The Warden’s Fuckslut

The jail Warden luvs it tough and tough and..

Added: 2024-12-30 Rating: n/a

Assullum superslut

A young inmate is attempting to lurk from the..

Added: 2024-12-29 Rating: n/a

Tips for a lucky job dialogue

In part 3 Bruno has Tony take Anna Belle on a..

Added: 2024-12-24 Rating: n/a

Laurie Steele

In part 3 Bruno has Tony take Anna Belle on a..

Added: 2024-12-18 Rating: n/a

Gina Hill

In part 3 Bruno has Tony take Anna Belle on a..

Added: 2024-12-15 Rating: n/a

Sarah Mills

In part 3 Bruno has Tony take Anna Belle on a..

Added: 2024-12-15 Rating: n/a

Linda Mitchell

In part 3 Bruno has Tony take Anna Belle on a..

Added: 2024-12-15 Rating: n/a

Warden Lola Interview’s Fresh Guard part 3

In part 3 Bruno has Tony take Anna Belle on a..

Added: 2024-12-10 Rating: n/a

Lesbian Vengeance

This desire roleplay shoot is an ode to..

Added: 2024-12-08 Rating: n/a

The Warden

In this week’s update Queen Donna plays a..

Added: 2024-12-03 Rating: n/a

The Super-naughty Journalist

Courtney Taylor’s an undercover journalist who..

Added: 2024-11-17 Rating: n/a

Laura Red - Womens Jail Showers (2024)

The rougher the gangster, the more preferential..

Added: 2024-11-07 Rating: n/a

Caught smoking while working & is sent to Isis Enjoy

In a city like San Francisco, smoking ciggies is..

Added: 2024-10-30 Rating: n/a

Uber-sexy Blond Jail Warden with Big Tits gets Gangbanged by Wild Inmates

In this dream roleplay update Samantha Sin plays..

Added: 2024-10-28 Rating: n/a

Encaged Feet: A Chicks In Jail Footsploitation Film!

In this sole fetishists fantasy come true film..

Added: 2024-10-28 Rating: n/a

Showers Gang-bang At Women's Jail

The harsher the gangster, the more preferential..

Added: 2024-10-26 Rating: n/a

New Meat for the Warden

Prisoner Danica Dillan gets visited by a sexy..

Added: 2024-09-11 Rating: n/a

Rectal Inmate

Tia Ling is the fresh dame in Ariel X’s jail..

Added: 2024-09-06 Rating: n/a

The Warden

In this week’s update Goddess Donna plays a..

Added: 2024-09-01 Rating: n/a

The Crazy Journalist

Courtney Taylor’s an undercover journalist who..

Added: 2024-08-08 Rating: n/a

Glorious Platinum-blonde Prison Warden With Thick Mounds fresh sadism & masochism porno flicks

In this wish roleplay update Samantha Sin plays..

Added: 2024-07-27 Rating: n/a

Ash-blonde Jail Warden With Ample Fun bags Gets Group-fucked fresh domination & submission porno vids

In this dream roleplay update Samantha Sin plays..

Added: 2024-07-19 Rating: n/a

Ashlynn Leigh, caught smoking while working

In a city like San Francisco, smoking ciggies is..

Added: 2024-05-22 Rating: n/a

The Insane Journalist

Courtney Taylor’s an undercover journalist who..

Added: 2024-05-16 Rating: n/a

Knuckle Pounding The Warden

Welcome Cougar star Anjanette Astoria to..

Added: 2024-05-07 Rating: n/a

Frauen im Liebeslager

A gang of ladies are kidnapped by guerrillas and..

Added: 2024-03-28 Rating: n/a

Ilsa, The Sinful Warden

Ilsa, now a perverse warden, runs a..

Added: 2024-03-01 Rating: n/a

Frauen im Liebeslager

A gang of damsels are kidnapped by guerrillas..

Added: 2024-02-18 Rating: n/a

Ilsa, The Wicked Warden

Ilsa, now a perverse warden, runs a..

Added: 2024-02-17 Rating: n/a

Kate Kenzi - Prisoner

In the world that Kate Kenzi was born into..

Added: 2024-01-19 Rating: n/a

Restrain bondage Is The Fresh Black: Vignette 2

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Added: 2024-01-13 Rating: n/a

Kate Kenzi - Prisoner

In the world that Kate Kenzi was born into..

Added: 2024-01-08 Rating: n/a

Kate Kenzi - Sexually masochistic jail

The manager warden has been given the task of..

Added: 2023-07-10 Rating: n/a

Youthfull Duo And Busty Cougar

Danica Dillon desired to have a conjugal visit..

Added: 2023-07-09 Rating: n/a

Restrain bondage Is The Fresh Dark-hued - Scene 2

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Added: 2023-06-21 Rating: n/a

Kate Kenzi - Prisoner

In the world that Kate Kenzi was born into..

Added: 2023-04-18 Rating: n/a

Bad Femmes Get Disciplined

When the renowned felon, Racquel is eventually..

Added: 2023-04-15 Rating: n/a

Prisoner

In the world that Kate Kenzi was born into..

Added: 2023-02-06 Rating: n/a

Prisoner

In the world that Kate Kenzi was born into..

Added: 2023-01-31 Rating: n/a

Luxurious Kate Kenzi is sentenced to life in a sexually masochistic jail

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Added: 2023-01-29 Rating: n/a

Corrupt Warden Penetrates Horny Prisoners Ppv

Quinnfinite and I got locked in a dingy damp box..

Added: 2023-01-28 Rating: n/a

Kenzie Taylor - Her Guilty Secret (2022)

Sara (Bella Blu) is chatting with her parent,..

Added: 2022-12-27 Rating: n/a

Femmes prisoners punished

A very first ever Mini Series. Bondage Is The..

Added: 2022-12-22 Rating: n/a

Have fun Pen

At the nys penitentiary known as 'The Playpen',..

Added: 2022-09-26 Rating: n/a

Hot Duo And Crazy Buxom Cougar

Danica Dillon dreamed to have a conjugal visit..

Added: 2022-09-24 Rating: n/a

Pounding the head warden

This inmate humps the hell out of the head..

Added: 2022-09-07 Rating: n/a

Prisoner

In the world that Kate Kenzi was born into..

Added: 2022-08-21 Rating: n/a

Restrain bondage Is The Fresh Black: Sequence 2

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Added: 2022-05-16 Rating: n/a

Harley Ace, Winnie Rider and Ashley Lane

A very first ever InfernalRestraints Mini..

Added: 2022-05-15 Rating: n/a

Restrain bondage Is The New Black: Vignette 1

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Added: 2022-03-10 Rating: n/a

Busty Fantastic Nymph Has Some Tough Fuckin Job

The Year 2021. The world has been overrun with..

Added: 2021-06-30 Rating: n/a

Les brulantes (1969)

Fresh inmate Marie arrives at an island jail in..

Added: 2021-05-12 Rating: n/a

Harley Ace, Winnie Rider, Ashley Lane high

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Added: 2021-04-24 Rating: n/a

Restrain bondage Is The Fresh Black: Vignette 1

A first-ever ever InfernalRestraints Mini..

Added: 2021-02-25 Rating: n/a

Fuck midget warden

Exclusive! Midgets! Sex dwarfs with dwarfs,..

Added: 2020-03-23 Rating: n/a

Bondage Is The New Black Episode 2

Previously on Bondage Is The New Black Pepper..

Added: 2020-03-04 Rating: n/a

Hooked - Abigail Dupree

On the Hook Impalement, the Ass Hook is a..

Added: 2020-02-22 Rating: n/a

Hooked

On the Hook Impalement, the Ass Hook is a..

Added: 2019-10-05 Rating: n/a

Warden Lola Interviews New Guard Part1

In this series Lola is at her desk when there is..

Added: 2019-09-09 Rating: n/a

Warden Lola Interviews New Guard part 1

In this series Lola is at her desk when there is..

Added: 2019-07-24 Rating: n/a

Lola: The Bad Warden part 3

In the final part of this series Lola Lynn gets..

Added: 2019-07-23 Rating: n/a

Bad Girls Get Punished

When the notorious felon, Racquel is finally..

Added: 2019-06-18 Rating: n/a

Sexy Hot Lady Has Some Tough Fuckin Job

The Year 2021. The world has been overrun with..

Added: 2019-06-01 Rating: n/a

Bondage Is The New Black part 2

Previously on Bondage Is The New Black Pepper..

Added: 2019-05-18 Rating: n/a

Bondage Is The New Black ,Episode 1

A first ever InfernalRestraints Mini Series...

Added: 2019-03-10 Rating: n/a

Les brulantes

New inmate Marie arrives at an island prison in..

Added: 2019-02-19 Rating: n/a

Fuck midget warden

Exclusive! Midgets! Sex dwarfs with dwarfs,..

Added: 2019-01-29 Rating: n/a

Bondage Is The New Black Part 2 - HD 720p

Previously on Bondage Is The New Black Pepper..

Added: 2019-01-13 Rating: n/a

Personal Pillory

Sadie Franklin has been misbehaving and she..

Added: 2019-01-11 Rating: n/a

Fist Fucking The Warden

Welcome MILF star Anjanette Astoria to..

Added: 2018-12-30 Rating: n/a

Ashlynn Leigh, caught smoking while working & is sent to Isis Love in order to keep her job!

In a city like San Francisco, smoking cigarettes..

Added: 2018-12-24 Rating: n/a

Personal Pillory , Sadie Franklin , HD 720p

Sadie Franklin has been misbehaving and she..

Added: 2018-12-23 Rating: n/a

Bondage Is The New Black Episode 1 , HD 720p

A first ever InfernalRestraints Mini Series...

Added: 2018-10-18 Rating: n/a

Bondage Is The New Black Episode 2 , HD 720p

Previously on Bondage Is The New Black Pepper..

Added: 2018-10-18 Rating: n/a

Les Brulantes (1969) - Maria Schell, Mercedes McCambridge

New inmate Marie arrives at an island prison in..

Added: 2018-10-17 Rating: n/a

Fist Fucking The Warden

Welcome MILF star Anjanette Astoria to..

Added: 2018-10-04 Rating: n/a

Ashlynn Leigh, caught smoking while working & is sent to Isis Love in order to keep her job!

In a city like San Francisco, smoking cigarettes..

Added: 2018-09-28 Rating: n/a

Stella Cox's Second Appearance - August 9, 2016

You saw what happened to Subil Arch. Well, her..

Added: 2018-09-21 Rating: n/a

Les Brulantes (1969) - Maria Schell, Mercedes McCambridge, Maria Rohm

New inmate Marie arrives at an island prison in..

Added: 2018-08-22 Rating: n/a

Harley Ace Winnie Rider And Ashley Lane

A first ever InfernalRestraints Mini Series...

Added: 2018-08-21 Rating: n/a

Kate Kenzi

Kate Kenzi is sentenced to life in a sexually..

Added: 2018-08-03 Rating: n/a

Prisoner 84621

In the world that Kate Kenzi was born into..

Added: 2018-06-25 Rating: n/a

Les Brulantes (1969) - Maria Schell, Mercedes McCambridge, Maria Rohm

New inmate Marie arrives at an island prison in..

Added: 2018-05-18 Rating: n/a

Fuck midget warden

Exclusive! Midgets! Sex dwarfs with dwarfs,..

Added: 2018-02-14 Rating: n/a

Les Brulantes (1969) - Maria Schell, Mercedes McCambridge, Maria Rohm

New inmate Marie arrives at an island prison in..

Added: 2018-02-10 Rating: n/a

Bondage Is The New Black Episode 2

Previously on Bondage Is The New Black Pepper..

Added: 2018-02-06 Rating: n/a

The rooky

This girl is new in prison. She's going to learn..

Added: 2018-02-02 Rating: n/a

Private Pillory

Sadie Franklin has been misbehaving and she..

Added: 2017-12-23 Rating: n/a

The rooky

This doll is fresh in prison. She's going to..

Added: 2017-10-06 Rating: n/a

The rooky

This gal is fresh in prison. She's going to..

Added: 2017-06-18 Rating: n/a

Personal Pillory

Sadie Franklin has been misbehaving and she..

Added: 2017-06-16 Rating: n/a

A Young Duo And Buxom Sexy Cougar

Danica Dillon desired to have a conjugal visit..

Added: 2017-05-28 Rating: n/a

Individual Pillory

Sadie Franklin has been misbehaving and she..

Added: 2017-05-18 Rating: n/a

Knuckle Pounding The Warden

Welcome Mummy starlet Anjanette Astoria to..

Added: 2017-04-16 Rating: n/a

Jail Heat: Gangbang cherry prays to be brutalized!

Welcome Virginia Colons to Hardcore Gangbang!..

Added: 2017-04-10 Rating: n/a

Ashlynn Leigh, caught smoking while working & is sent to Isis Enjoy in order to keep her job!

In a city like San Francisco, smoking ciggies is..

Added: 2017-04-10 Rating: n/a

Pulverize midget warden

Exclusive! Midgets! Fucky-fucky dwarfs with..

Added: 2017-03-27 Rating: n/a

Bad Dolls Get Disciplined

When the legendary felon, Racquel is eventually..

Added: 2017-03-14 Rating: n/a

Harley Ace Winnie Rider And Ashley Lane

A very first ever InfernalRestraints Mini..

Added: 2016-12-02 Rating: n/a

Bondage Is The Fresh Black: Scene 1

Restrain bondage Is The Fresh Ebony is a porno..

Added: 2016-09-05 Rating: n/a

Harley Ace

Pepper Channing, Alice Vicks, and Tasha..

Added: 2016-08-31 Rating: n/a

Bondage Is The Fresh Black: Gig 2

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Added: 2016-08-31 Rating: n/a

Restrain bondage Is The Fresh Black: Vignette 2

Precedingly on Restrain bondage Is The Fresh..

Added: 2016-07-02 Rating: n/a

Harley Ace, Winnie Rider and Ashley Lane

A first-ever ever Mini Series. Restrain bondage..

Added: 2016-07-02 Rating: n/a

Barbed String Women

"Barbed Cord Dolls" has to be one of the..

Added: 2016-07-01 Rating: n/a

Restrain bondage Is The Fresh Dark-hued

Pepper Channing, Alice Vicks, and Tasha..

Added: 2016-06-21 Rating: n/a

Restrain bondage Is The New Black 2

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Added: 2016-06-10 Rating: n/a

Harley Ace Winnie Rider And Ashley Lane

A first-ever ever InfernalRestraints Mini..

Added: 2016-06-09 Rating: n/a

The Crimson Reformatory: Elder Pals

We meet again to witness a fresh Lupus Images..

Added: 2016-05-10 Rating: n/a

Restrain bondage Is The Fresh Black: Episode 2 - Only Agony HD

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Added: 2016-04-29 Rating: n/a

Youthful Duo And Highly Spectacular Mummy

Danica Dillon wished to have a conjugal visit..

Added: 2015-12-17 Rating: n/a

Restrain bondage Is The New Black: Vignette 1

Bondage Is The Fresh Ebony is a porno parody...

Added: 2015-12-12 Rating: n/a

Harley Ace, Winnie Rider and Ashley Lane

A first-ever ever InfernalRestraints Mini..

Added: 2015-11-22 Rating: n/a

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