Prison 338


Newest Prison Videos


Debt 4K - Sata Jones

Dec 16

Clips, HD

Dec 16

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Sata Jones - E19
Released: December 16, 2021

This lady caught my attention – I have never EVER seen someone slip into debt prison because of adult toys. I managed to track her down and enter her apartment undetected! Her collection of sex toys really was an impressive one. Once the girl barged into the room, she was dumbstruck after seeing the handsome stranger (me) but I made things REAL clear: Listen up, baby – there are two ways this can end. You either return the toys or you enjoy the real deal right now. What’s your pick?

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Brazzers Exxtra - Audrey Madison

Nov 23

Clips, HD, Big Tits

Nov 23

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Audrey Madison - Break Out Get In
Released: November 23, 2021

The perverse but shy Audrey Madison has a unique passion: writing erotic letters to inmates at the local prison. One night, one of her pen pals, bad boy Alex Mack, breaks out of jail just to pay her a visit. Audrey has been waiting for this moment for so long, aroused by the months of exchanges sex stories and confidences. It doesn't take too long before she lets Alex fill her pleasure hole!. After a passionate sex session, it's time for the replete Alex to start a new life as a free man.

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Hot And Mean - Victoria Cakes & Clara Trinity

Nov 18

Clips, HD, Asian, Big Tits, Ebony, Lesbian

Nov 18

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Victoria Cakes & Clara Trinity - Fucking The Hitchhiker And The Jailbird - Part 1
Released: November 18, 2021

Victoria Cakes is driving out in the country, when she picks up sweet and sexy hitchhiker Clara Trinity. After having some fun flashing litter-picking prisoner Kyle Mason on the side of the road (more on him later!), Victoria drives Clara off to a secluded area and has the hitchhiker ride on a dildo fixed to the gear shift. The girls then run off into the woods and find a good place to fuck, all while avoiding Kyle and the warden in charge of watching him.

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Facial Abuse - Rebel Rhyder

Nov 14

Clips, HD, Anal, Fetish

Nov 14

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Rebel Rhyder - Manhandled Asshole
Released: November 14, 2021

I'll start off at the anal first in my tale of woe and misery. Her asshole was turned inside out--like a pink glove reached out to shake our cocks. She spread it wide open and you could see the pearly white nut that was deposited in her rectum like prison sex. She cleaned up all her face fucked mess with her mouth as she was getting plowed from behind as her brand new tits bounced to and fro. She did A2M and got slapped like a hooker by her daddy after taking communion...

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Mugur Porn - Gina Gerson

Nov 13

Clips, HD, Euro, Threesome

Nov 13

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Gina Gerson - Stepbrother The Escaped Prisoner: Part 1
Released: November 12, 2021

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Stay Home Milf - Kiara Lord

Nov 8

Clips, 4K, Big Tits, MILF, POV

Nov 8

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Kiara Lord - Off on Good Behavior
Released: November 8, 2021

When Mugur Porn comes home from prison, his stepmother Kiara Lord couldn’t be happier. She tries to make his first day home as enjoyable as possible by giving him whatever he wants—and there is only one thing on Mugur’s mind.

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Adult Prime - Ursula & Jimena Lago

Nov 4

Clips, HD, Threesome

Nov 4

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Ursula & Jimena Lago - Three Prisoners
Released: November 4, 2021

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Blacks On Blondes - Lola Fae

Oct 5

Clips, HD, Interracial, Threesome

Oct 5

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Lola Fae - Blacks On Blondes
Released: October 5, 2021

Seems Lola is involved in stealing checking account numbers and cashing fraudulent checks. Seems this petite girl fancies herself quite the criminal and loves treating her posse of user friends to expensive meals and party nights on stolen funds. Well guess what missy - the Dogfart plainclothes fraud division has caught up with you and justice is calling. Detectives Rico and Prince know how to deal with these type of troublemakers and soon have Lola confessing her crimes and pointing fingers at who is really behind it. Now for a stiff dicking to set her on the straight and narrow.

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Teen Fidelity - Amber Moore

Sep 14

Clips, HD, Teen

Sep 14

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Amber Moore - Coming Home - E484
Released: September 14, 2021

Brad has been released from prison, and makes his way back to Amber, who has waited patiently for him. They don't waste a lot of time with small talk, as her big natural teen tits demand his attention. Her body is the best coming home gift he could ever receive, and it doesn't take him long to blast his load all over that juicy ass.

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Glory Hole Secrets - Ophelia Kaan

Sep 10

Clips, HD 1 mode_comment

Sep 10

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Ophelia Kaan - Ophelia's First Gloryhole Video
Released: September 10, 2021

You know that sexy librarian in all those '80s & '90s music videos who would let down her hair and suddenly become the sexy video vixen? That's what we have this week with newcomer Ophelia in her FIRST GLORYHOLE EVER. She may look quiet and reserved with her clothes on and her hair up, but let that bangin' body out of its cotton prison and there is a sex goddess underneath. It comes out in her interview that she is a closet freak. 38-year-old Ophelia is a MILF who looks a decade younger than what her driver's license reads (we checked)...

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Jax Slayher TV - Avery Black

Aug 26

Clips, HD, Asian, Interracial

Aug 26

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Avery Black - FRESH OUT
Released: February 15, 2021

When I got released from prison, my bottom bitch Avery Black came to scoop me up. Then took me out for a bite to eat before I gave her some of this daddy dick that she was missing while I was doing time.

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The Life Erotic - Gaia Sofia

Aug 4

Clips, HD, Euro, Fetish

Aug 4

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Gaia Sofia - Sexual Release # 2
Released: August 4, 2021

Sexy brunette submissive Gaia Sofia is bound, gagged, and crammed into a tiny cage fashioned from a wooden crib and bondage cords. She is on her knees, head bowed and ass thrust in the air, naked except for black thong panties. Turned on by her kinky predicament, she squirms against the mattress.

Next, an anonymous man wearing black surgical gloves strokes her panty-crotch, then stretches it aside to expose her trimmed pussy and tight asshole. He teases her slit and, when she is wet enough, pumps a black dildo in her snatch and pushes it in deep. His latex-clad fingers tease the rim of her asshole, then guide her hands onto the dildo before he leaves...

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DDF Busty - Skylar Vox

Aug 4

Clips, 4K, Big Tits, Threesome

Aug 4

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Skylar Vox - Busty Blonde Slut Skylar Vox Tagged Teamed by 2 Escaped Prisoners
Released: August 4, 2021

After writing a letter to her degenerate boyfriend who’s an inmate in the California State Prison system, busty blonde slut Skylar Vox’s pussy is wet. However, little does she know that she’s in for a pleasant surprise because her boyfriend – who’s just escaped prison with his inmate pal – is nearly at her house. Once the initial shock of seeing each other for the first time in years wears off, Tyler takes his orange prison jumpsuit off and starts fucking his girlfriend. Like the true friend that he is, Tyler ends up sharing his girlfriend with his prison friend Will, who hasn’t fucked a woman for years. Together, the two dudes give Skylar a fuck that she hasn’t received in a long time.

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Sex Mex - Sara Blonde

Jun 27

Clips, HD

Jun 27

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Sara Blonde - Sex In Prison
Released: June 27, 2021

Sarah Blonde got caught masturbating in a mall bathroom. They took her to jail and, she will have to spend seven days in prison. She will offer sexual favors to the warden to lessen her sentence.

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Digital Playground - Lulu Chu & Nicole Kitt

Jun 21

Clips, HD, Asian, Ebony, Lesbian 1 mode_comment

Jun 21

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Lulu Chu & Nicole Kitt - Wait For Me
Released: June 21, 2021

After Lulu Chu escapes from prison, the only thing she has on her mind is seeing her ex-girlfriend, Nicole Kitt. Nicole, however, has moved on and is living with her new boyfriend, Zac Wild, which Lulu discovers after sneaking into her home and witnessing them being intimate. The heartbroken convict will not let this deter her however, planning on getting her ex-lover back at any cost... and she doesn't want to share her with anybody.

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Scoreland - Dominno

Jun 19

Clips, HD, Big Tits

Jun 19

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Dominno - Prisoner Of Dominno
Released: June 18, 2021

The great Dominno makes Perry her slave, putting a leash around his neck like a dog and handcuffing him. She wants a slave to obey her without question, eat her pussy and do whatever she wants. Perry's not complaining at all. He's happy to be in Dominno's space because she's a superstar sex-bomb in the Czech Republic. He's watched Dominno's videos and is honored to serve. Dominno offers him her dainty stockinged foot and her shoe to kiss and grovel at...

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