Jail Bondage

Pages: NEXT ►

Order by: Popular Date Relevance

Infernalrestraints - Safe Building 2 Part 1

Her delivery method speaks lucidly of where she..

Added: 2025-03-21 Rating: n/a

Infernalrestraints - Restrain bondage Is The Fresh Black: Vignette 2

Previously on Restrain bondage Is The Fresh..

Added: 2025-03-20 Rating: n/a

Helen Russell

Sarah’s the new nice and virginal female in..

Added: 2025-03-11 Rating: n/a

Buttfuck Extortion

Giant caboose dark haired Kimber Forest is in..

Added: 2025-03-10 Rating: n/a

Mary Gibson

Sarah’s the fresh ultra-cute and harmless..

Added: 2025-03-08 Rating: n/a

Carol Morales

Sarah’s the new lovely and innocent chick in..

Added: 2025-03-07 Rating: n/a

Penny's Anal Embezzlement

When Penny Pax is confronted by her employer’s..

Added: 2025-03-06 Rating: n/a

Leather chic

Sarah’s the fresh lovely and innocent nymph in..

Added: 2025-02-28 Rating: n/a

Trouble at the Mansion of Gord

Gord and Nymph Serena love an evening of freaky..

Added: 2025-02-16 Rating: n/a

The Role Reversal Game

Simone Sonay is our super-sexy Cougar jail..

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

Stealing Maid

Huge-boobed towheaded Angel Vain gets caught..

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

Sophie is Punished Daily in Bondage & discipline Jail with Clips

Sophie is disciplined daily by trio jail guards...

Added: 2025-01-31 Rating: n/a

Spy Mirela is Caught Suffers a Sadism & masochism Interrogation

Mirela is caught on the grounds of Reverend..

Added: 2025-01-31 Rating: n/a

Reporter is Caught Trespassing Imprisoned for Sadism & masochism Punishment

Mirela is caught on the lands of Reverend..

Added: 2025-01-31 Rating: n/a

Heidi is Imprisoned for Bondage & discipline Penalty for False Charity Work

Heidi is collecting charity donations from door..

Added: 2025-01-30 Rating: n/a

Mirela Will Confess After Sadism & masochism Imprisonment Electro Have fun

Mirela was arrested for being a spy and..

Added: 2025-01-30 Rating: n/a

Spy Mirela Won't Confess

Mirela has been in interrogation for several..

Added: 2025-01-30 Rating: n/a

Nadja Suffers Daily Bondage & discipline Punishment Humilation with Blow Blowjob

Nadja is disciplined daily by 2 jail guards...

Added: 2025-01-30 Rating: n/a

Call girl Nadja is Imprisoned for Bondage & discipline Punishment

Nadja has been in jail for a few years where she..

Added: 2025-01-30 Rating: n/a

Nadja's Domination & submission Interrogation Involves a Rusty Hook her Slit

Nadja's interrogation is still in progress. Her..

Added: 2025-01-30 Rating: n/a

Nadja Suffers Daily Bondage & discipline Punishment Humilation with Fire

Nadja's imprisonment has been spent in a dark..

Added: 2025-01-30 Rating: n/a

Hooker Nadja Hates Sadism & masochism Prison Torture She Earned

"Sexy brunette, nineteen years old, looking for..

Added: 2025-01-30 Rating: n/a

Nadja Swears Purity as She's Punished with Ciggies

Nadja, a nasty youthful slut, mimes virginal..

Added: 2025-01-30 Rating: n/a

Natalia is Strapped Made to Gag on a Fake penis in Bondage & discipline Jail

Natalia is penalized daily by a Jail medic and..

Added: 2025-01-30 Rating: n/a

Natalia's Sadism & masochism Penalty Includes Speculum, Water Boarding

Natalia was arrested for being an undercover..

Added: 2025-01-30 Rating: n/a

Town Slut Natalia Suffers Medical Torture with Jail Doc

Natalia flirts with everyone in town. She is..

Added: 2025-01-30 Rating: n/a

Lori Endures Gonzo Orb Torture Abjection in Jail

Lori was arrested for prostitution again and..

Added: 2025-01-30 Rating: n/a

Lise is Disciplined in Solitary Restriction with Waterboarding & Humiliation

Eyes covered with a sack over her head, Lise is..

Added: 2025-01-30 Rating: n/a

Mirela is Tormented with a Cattle Prod in Punishment Imprisonment

Mirela is caught on the lands of Reverend..

Added: 2025-01-30 Rating: n/a

Lise is Still Conforming Imprisonment in Solitary Limitation with Tit Torture

Lise never thought her imprisonment would be..

Added: 2025-01-30 Rating: n/a

Nadja is Imprisoned Will Suffer Bondage & discipline Penalty

Nadja, a wild prostitute, has been caught and..

Added: 2025-01-30 Rating: n/a

Lengthy Sadism & masochism Imprisonment Interrogation with Mirela

Mirela has been in interrogation for months and..

Added: 2025-01-30 Rating: n/a

Sophie is Bound in Domination & submission Jail for Rock-hard Spanks

Sophie is a betting dork and has amounted fairly..

Added: 2025-01-30 Rating: n/a

Sophie is in Bondage & discipline Jail

Sophie is imprisoned for punishment. She must..

Added: 2025-01-30 Rating: n/a

Sophie has Earned Lash Cream Dild

Sophie is disciplined daily by trio jail guards...

Added: 2025-01-30 Rating: n/a

School Campus Flirt is Imprisoned for BDSM & Humiliating Penalty

Clara flirts with everyone at her college. She..

Added: 2025-01-30 Rating: n/a

Bea Suffers Ache Play While Cleaning the Floor her Coochie

Major Claudia was disgusted with some newspaper..

Added: 2025-01-30 Rating: n/a

Lori is Imprisoned Penalized for Prostitution

Lori was arrested for prostitution and..

Added: 2025-01-30 Rating: n/a

Lori Obeys her Imprisonment Suffers Hard-core Breast Torment

Lori is arrested and imprisoned. Her punishment..

Added: 2025-01-30 Rating: n/a

Lori is Imprisoned for Infidelity Suffers 1st BDSM Shower

Lori was arrested for adultery and imprisoned...

Added: 2025-01-30 Rating: n/a

Zen Jail Studio scene 0127

All in all, everyone had a joy afternoon toying..

Added: 2025-01-29 Rating: n/a

Gooey Steaming Wrap Trap

In a shoot that features some of the best..

Added: 2025-01-29 Rating: n/a

Rectal Payback

Platinum-blonde sweetheart Lily LaBeau pays for..

Added: 2025-01-29 Rating: n/a

Zen Jail Studio gig 0112

All in all, everyone had a joy afternoon..

Added: 2025-01-24 Rating: n/a

Zen Jail Studio gig 015

All in all, everyone had a joy afternoon toying..

Added: 2025-01-23 Rating: n/a

Gia Jordan and Brian Surewood

Gia Jordan is one super-naughty chick who has a..

Added: 2025-01-18 Rating: n/a

Fist Fucking The Warden

Welcome Cougar starlet Anjanette Astoria to..

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

Hooker Natalia is Imprisoned for BDSM Penalty

Natalia has been in interrogation for months and..

Added: 2025-01-11 Rating: n/a

Escort Natalia is Imprisoned for Sadism & masochism Penalty

Natalia was arrested for prostitution and..

Added: 2025-01-11 Rating: n/a

Sophie is Penalized Daily in Domination & submission Jail with Clamps

Sophie is punished daily by 3 jail guards. She's..

Added: 2025-01-11 Rating: n/a

Sophie is Corded in Bondage & discipline Prison for Rigid Spanks

Sophie is a betting fool and has amounted fairly..

Added: 2025-01-11 Rating: n/a

Sophie is in Sadism & masochism Jail

Sophie is imprisoned for punishment. She must..

Added: 2025-01-11 Rating: n/a

Sophie has Earned Lash Juices Dild

Sophie is disciplined daily by three jail..

Added: 2025-01-11 Rating: n/a

Lori is Imprisoned Punished for Prostitution

Lori was arrested for prostitution and..

Added: 2025-01-11 Rating: n/a

School Campus Flirt is Imprisoned for Bondage & discipline & Abasing Penalty

Clara flirts with everyone at her college. She..

Added: 2025-01-10 Rating: n/a

Bea Suffers Agony Have fun While Cleaning the Floor her Cooter

Major Claudia was disgusted with some newspaper..

Added: 2025-01-10 Rating: n/a

Lise is Disciplined in Solitary Limitation with Waterboarding & Indignity

Blinded with a balls over her head, Lise is..

Added: 2025-01-10 Rating: n/a

Lori Conforms her Imprisonment Suffers Hardcore Jug Torment

Lori is arrested and imprisoned. Her punishment..

Added: 2025-01-10 Rating: n/a

Lori is Imprisoned for Infidelity Suffers 1st Bondage & discipline Bathroom

Lori was arrested for cuckoldry and imprisoned...

Added: 2025-01-10 Rating: n/a

Lori Suffers Gonzo Melon Torture Abasement in Jail

Lori was arrested for prostitution again and..

Added: 2025-01-10 Rating: n/a

Reporter is Caught Trespassing Imprisoned for BDSM Penalty

Mirela is caught on the lands of Reverend..

Added: 2025-01-10 Rating: n/a

Spy Mirela is Caught Suffers a Domination & submission Interrogation

Mirela is caught on the lands of Reverend..

Added: 2025-01-10 Rating: n/a

Lengthy Bondage & discipline Imprisonment Interrogation with Mirela

Mirela has been in interrogation for months and..

Added: 2025-01-10 Rating: n/a

Spy Mirela Won't Confess

Mirela has been in interrogation for a few days...

Added: 2025-01-10 Rating: n/a

Mirela is Tantalized with a Cattle Prod in Penalty Imprisonment

Mirela is caught on the lands of Reverend..

Added: 2025-01-10 Rating: n/a

Mirela Will Confess After Sadism & masochism Imprisonment Electro Play

Mirela was arrested for being a spy and..

Added: 2025-01-10 Rating: n/a

Nadja Endures Daily Bondage & discipline Penalty Humilation with Gargle Oral

Nadja is disciplined daily by 2 jail guards...

Added: 2025-01-10 Rating: n/a

Escort Nadja is Imprisoned for Domination & submission Penalty

Nadja has been in jail for several years where..

Added: 2025-01-10 Rating: n/a

Nadja Suffer Domination & submission Imprisonment Torture with Clamps

Nadja never thought her imprisonment would be..

Added: 2025-01-10 Rating: n/a

Nadja is Imprisoned Will Endure BDSM Penalty

Nadja, a super-naughty prostitute, has been..

Added: 2025-01-10 Rating: n/a

Call girl Nadja Hates Sadism & masochism Jail Torture She Earned

"Sexy brunette, 19 years old, looking for a job...

Added: 2025-01-10 Rating: n/a

Nadja Suffers Daily BDSM Penalty Humilation with Fire

Nadja's imprisonment has been spent in a dark..

Added: 2025-01-10 Rating: n/a

Nadja's Domination & submission Interrogation Involves a Rusty Hook her Vulva

Nadja's interrogation is still in progress. Her..

Added: 2025-01-10 Rating: n/a

Nadja Vows Innocence as She's Penalized with Ciggies

Nadja, a super-naughty youthful slut, mimes..

Added: 2025-01-10 Rating: n/a

Natalia Suffers Bondage & discipline Interrogation with Suspension

Natalia has been in interrogation for months and..

Added: 2025-01-10 Rating: n/a

Natalia is Bound Made to Gag on a Fake penis in Bondage & discipline Jail

Natalia is disciplined daily by a Jail physician..

Added: 2025-01-10 Rating: n/a

Natalia's Domination & submission Penalty Includes Speculum, Water Boarding

Natalia was arrested for being an undercover..

Added: 2025-01-10 Rating: n/a

Town Biotch Natalia Suffers Medical Torment with Jail Physician

Natalia flirts with everyone in town. She is..

Added: 2025-01-10 Rating: n/a

Sophia's secret

Sarah’s the new cute and harmless female in..

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

Linda Graham

Sarah’s the fresh lovely and virginal lady in..

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

Tips for staying concentrated while studying

Sarah’s the fresh lovely and innocent lady in..

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

Barbara Jones

Sarah’s the fresh ultra-cute and innocent dame..

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

Mabel Ferguson

Sarah’s the fresh cute and guiltless lady in..

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

Sharon Howard

Sarah’s the fresh nice and guiltless doll in..

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

Krissy Lynn Huge titted, blond, pent up in the Huge squeeze

Pent up in a custom-made jail only 6 inches..

Added: 2024-12-07 Rating: n/a

Kapri Styles African American Queen

Welcome Kapri Styles to Device Bondage. This..

Added: 2024-12-02 Rating: n/a

Penny's Assfuck Embezzlement

When Cent Pax is confronted by her employer´s..

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

Assfuck Extortion - Charles Dera, Kimber Woods

Humungous bum black-haired Kimber Forest is in..

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

Ass-fuck Payback

Blonde sweetheart Lily LaBeau pays for her..

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

Jail Paralegal

All paralegal Maya Kendrick needs to do is get..

Added: 2024-11-16 Rating: n/a

Legitimate Year Aged Assfuck Rehab

When 18-year old April Aniston finds herself..

Added: 2024-11-16 Rating: n/a

Dana DeArmond, Claire Robbins, Emma Haize (Anal Bi-atch Jail Whores)

She fights against the cold steel and leather,..

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

Lengthy term horse chick instructing pt.2

The next thing she knows she wakes up in a bed,..

Added: 2024-10-22 Rating: n/a

Baby In Chains Belicia

With your distorded password you get access to..

Added: 2024-10-17 Rating: n/a

Jail Paralegal

All paralegal Maya Kendrick needs to do is get..

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

Anal invasion Extortion - Charles Dera, Kimber Forest

Phat donk black-haired Kimber Forest is in some..

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

Penny's Anal invasion Embezzlement

When Cent Pax is confronted by her employer´s..

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

La Turista

When bitchy, big jug Yankee tourist Kagney Linn..

Added: 2024-10-07 Rating: n/a

Wealthy Hoe

Alicia Stone plays a wealthy gal who gets thrown..

Added: 2024-09-27 Rating: n/a

Wealthy Tart new bondage & discipline pornography movies

Alicia Stone plays a wealthy dame who gets..

Added: 2024-09-22 Rating: n/a

Barely legal Counsel: Zoe Sparx Trades Crevices For Barely legal Representation

When check fraudster Zoe Sparx gets into trouble..

Added: 2024-09-12 Rating: n/a

Miss Sultrybelle - Authentic Malaysian Judicial

Gemma and Amy have been caught snooping and are..

Added: 2024-09-04 Rating: n/a

The Warden

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

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

Krissy Lynn Massive titted, blond, pent up in the Massive squeeze.

Pent up in a custom-made jail only 6 inches..

Added: 2024-08-22 Rating: n/a

Sandra Romain and Jazmine Leih fresh sadism & masochism porn videos

Jazmine Leih and Sandra Romain have fun 2 call..

Added: 2024-08-22 Rating: n/a

Secondary Moaning

She's apprehensive, but she obeys as he has Luci..

Added: 2024-08-13 Rating: n/a

Secondary Moaning

Airport security is just the worst. For Luci..

Added: 2024-08-11 Rating: n/a

Victim Dame Earns a Couch

Delilah Knight is hastily finding out her utter..

Added: 2024-07-29 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

Gloppy Red-hot Wrap Trap fresh bondage & discipline porno movies

In a shoot that features some of the finest..

Added: 2024-06-24 Rating: n/a

Meet The Jail Wire fresh bondage & discipline porno flicks

It has been a while since we’ve seen Lita..

Added: 2024-06-04 Rating: n/a

Tia Ling Punctured in a one person jail

Welcome Tia Ling to Implement Bondage. Pent up..

Added: 2024-06-03 Rating: n/a

Whim Hunter

"I was obsessed with freedom, craved freedom,..

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

La Turista fresh domination & submission porn flicks

When bitchy, ginormous titty American tourist..

Added: 2024-05-02 Rating: n/a

Ass-fuck Extortion fresh sadism & masochism porn vids

Massive bootie dark-haired Kimber Forest is in..

Added: 2024-04-30 Rating: n/a

One Jail

Today's goal is climaxes while being bound,..

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

Categories

Our Friends

Disclaimer: All models on this adult site are 18 years or older. Our site has a zero-tolerance policy against illegal pornography. All videos and links are provided by 3rd parties. We have no control over the content of these pages. We take no responsibility for the content on any website which we link to, please use your own discretion while surfing the porn links. This website uses cookies to ensure you get the best experience on our website.

© FilesMonster.TV • DMCA Policy • Privacy Statement • Trade Traffic •