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Prison 386

Newest Prison Videos

She Seduced Me - Marica Hase Prison Gangbang

Marica Hase, Aiden Starr, Alexa Chains, Isabella Nice, Lana Violet - Marica Hase Prison Gangbang
Released: March 25, 2026

Marica Hase is a strict prison guard who gets off on power-tripping her five alluring prisoners by dangling the keys to freedom right in front of them. Marica Hase is a petite 5'2"" Japanese MILF, with natural 32A-22-32 measurements, sleek black hair, brown eyes, and a slim, toned body that looks deceptively innocent in her uniform. Her prisoners—Aiden Starr 5'4"" brunette dominatrix,34B-26-34 curves, intense eyes, Alexa Chains curvy 5'1""-5'5"" mixed Latina, natural 32C-24-36 tits and round ass, Isabella Nice petite 5'0"" Latina spinner, natural 32B-26-32 perky frame, Lana Violet 5'2"" exotic beauty, 32C-24-34 toned exotic curves—have been waiting for their chance. One day Marica accidentally drops the keys, and the cell door swings open. In seconds the prisoners grab her, drag her inside, and show her what real power-tripping feels like...

Alena Croft - Pornstar Collection

Alena Croft Mega Collection
19 Videos | 10.25 GB

Alena Croft (also known as AZBlonde, born August 25, 1981) is an American porn star and adult model. Her measurements are 34F-26-38.

Shoplyfter - Krissy Knight

Krissy Knight - Case No. 8004863 - Stealing Award Ribbons Gets You Creamy Rewards
Released: March 7, 2026

Krissy tried to steal a pile of award ribbons from a craft store. Her insecurities pushed her to steal those to make it look like she’d won a ton of prizes and impress the boys they like, but she got caught. Joey, the security guard, wants to be understanding with her, but he cannot let her go without a thorough inspection. His suspicions are confirmed when stolen ribbon awards pop everywhere beneath her clothes. She’s absolutely busted and, if Joey decides to press charges, she’ll have to explain the situation to the cops and face some prison time. However, Joey knows how to handle these cases. Young ladies like Krissy need a little guidance from an experienced man like him. If she loves award ribbons so much, then this security guard can teach her what it really means to earn a prize…

Submissive X - New 2025 Updates

Ariel X & Savannah Fox - Sexy Lesbian Nuru Massage
Ariel X - Ariel Lifts and Carry Handsome Man
Ariel X & Mia Little - Anal Physical Therapy
... and MANY more!

Mixed X - Zazie Skymm & Candee Licious

Zazie Skymm & Candee Licious - The Other Memory
Released: February 20, 2026

Candee Licious arrives at a lakeside house with her lover, Zazie Skymm. The place is beautiful and serene, yet an unsettling atmosphere lingers in the air, as if the space itself remembers something they have forgotten. Candee Licious is tense and restless, unable to fully arrive in the present moment. Zazie, in contrast, is warm and patient, constantly trying to draw her back into the 'now,' into calm, into safety. As time passes, subtle irregularities appear within the house.

Freeze - Veronica Leal

Veronica Leal - Prison Bitch
Released: January 23, 2026

Newly-incarcerated Sam is escorted into his cell by a prison guard, where he is expected to remain for the rest of his life. In the adjacent cell, long-time prisoner Veronica taunts Sam into lashing out at her, causing the prison guard to enter Sam’s cell and beat him senselessly whilst Veronica enjoys the show.

Sex And Submission - Sophia Locke

Sophia Locke - Prison Break
Released: December 19, 2025

Vince Karter is locked up and fuming mad when his lawyer Sophia Locke arrives with news that although she’s done all she could, he’s going to have to stay in prison. He tells Sophia he’ll be out tonight. She laughs it off in spite of Vince’s menace, only to find him in her kitchen later that night. Vince takes hold of Sophia and reminds her who’s the boss with some breathe-play and face slapping. Using his belt to hold her in place, Vince gives Sophia a rough face-fucking.

Horny Hostel - Lapaisita & Tatiana Alvarez

Lapaisita & Tatiana Alvarez - Cuffed And Stuffed
Released: December 4, 2025

LaPaisita arrives at the prison, surrendering her buttplug and belongings before guards probe her holes and strip her into an orange jumpsuit. In her cell, Tatiana Alvarez explains rules while seducing her with hungry kisses and pussy grinds. The first guardian interrupts, as Tatiana sucks him deep, he calls Yeri Blue for backup, sparking a wild foursome fuck in cell and hallway. Girls take turns on thick cocks milking explosive cumshots across their faces and big tits. Exhausted guards collapse as the inmates steal keys and escape through the vents.

Futanari - New Autumn 2025 Updates

Dolly X & Tiffany Tatum - Ghosts Don't Exist
Matty Mila & Milan Cheek - Prison Witch
Amirah Adara, Black Angel & Dolly X - Exposed
Coco Bae & Matty Mila - Futa's Curse
Amirah Adara & Nata Gold - Someone's Watching
Audrey Reid & Octokuro - The Suspect
Clemence Audiard & Shaline Devine - Sleeper Agent
Released: November 30, 2025

Mature NL - 16 Old And Young Lesbians In A Prison Orgy

Agnessa, Bellatrix, Darya, Dina, Faina, Fedora, Janet Alfano, Janinka, Lola Danger, Mitzi X, Naomi Love, Rianna, Roksana, Sofie Morel, Suzie Sparklez - Old And Young Lesbians In A Wild Pussylicking Asslicking Prison Orgy Beyond You Wildest Dreams
Released: November 21, 2025

Women behind Bars! The ultimate old and young lesbian movie exclusively from your friends at mature.nl!

In over 80 minutes we take you to an all women prison where 14 prisoners and 2 guards get all wet in this all lesbian, pussy licking, asslicking lesbian prison orgy! We show you curvy, mature, younger ladies, grannies, moms and MILFs who got nothing else to do but eat and lick pussy all day long. There are old and young lesbian couples having sex to a complete orgy and groupsex sessions. They have sex in their cells, during the round up and even in the showers and on the toilet!

Cougar Seductions - Lolly Dames

Lolly Dames - Satisfying Lolly Dames' Desires
Released: November 22, 2025

When a cougar is on the prowl she is focused on only one thing: young hard meat that is ready and able to get her off. She takes no prisoners in her approach and has no time for worthless chit chat. Lolly Dames is here to fuck. Finding her pray (Goldey), she brings him home and immediately gets him to the couch to open the snap on his pants to get at his man meat. Within thirty seconds she has his massive cock buried deep in her mouth as she sucks it to a rock hard erection and soon has the young stud pounding her dripping wide open milf hole balls deep.

Sluts Around Town - Ashley Moore

Ashley Moore - Bad Girl Finally Gets To Hook Up
Released: October 30, 2025

Paroled bad girl Ashley has been so horny since getting out of prison. Once she gets her ankle monitor her first stop is her FWB’s house to finally satisfy her horny cravings

Dorcel Club - Agatha Vega

Agatha Vega - Prisoner of Desire
Released: October 24, 2025

Agatha Vega, a latex-clad dominatrix in corset and boots, reigns over a bound and gagged submissive, reduced to nothing more than a plaything. Yet he dares to make a bold request: to watch, powerless, as another man takes her pleasure… while he remains chained, obeying only his mistress’s commands.

Dorcel Club - Agatha Vega

Agatha Vega - Prisoner of Desire
Released: October 24, 2025

Agatha Vega, a latex-clad dominatrix in corset and boots, reigns over a bound and gagged submissive, reduced to nothing more than a plaything. Yet he dares to make a bold request: to watch, powerless, as another man takes her pleasure… while he remains chained, obeying only his mistress’s commands.

Jimena Lago - Pornstar Collection

Jimena Lago Mega Collection
25 Videos | 28.12 GB

Jimena Lago was born on October 13, 1994, in Madrid, Spain. Cute, petite and slim, the sexy Spaniard although young is slowly but surely becoming a porn star veteran. She started shooting adult films in 2013 at the age of nineteen. Jimena, sometimes credited as Aelita, has been actively shooting for four years in genres such as lesbian, POV, Latina, public, hardcore, teen, and toys.She has been shooting mostly for Spanish porn websites and companies such as putalokura.com, but also for international productions such as Viv Thomas, Girlfriend Films, Airerose Entertainment, Brazzers, Evil Angel, Perfect Gonzo DVD, BaDoink and so on. Jimena has a natural body and she is very proud of it. Her navel is decorated with a piercing. Her measurements are 35B-23-34.

Evil Angel - Asteria Jade

Asteria Jade - Obedient Prison Guard starring Asteria Jade
Released: September 11, 2025

Silas Stone is a prison guard... and he's obsessed with his new inmate. Her name is Asteria Jade and she has a way of looking at him that makes him want to get on his knees and submit to her. The way she looks deep in his soul... like she's already seen the future and know it involves her owning him. He comes to her cell for nightly inspection.. he tries to act with autority but he starts to feel confused when he tells her to stand up and she asks 'do I get something for it?'. She casually strolls over to him and asks 'what if you... get down on your knees for me officer?' as she brushes her finger across his chest. He knows he should tell her to shut up, but deep down, he wants this badly...

BUFU.xxx - All new updates

Lilly Bella - Blue Oyster Club Fantasy
Daruma Rai - Helping Hand in Metropolust
Lucy Mendez - Men's Prison Showers
Una Fairy - Back Swan
Vera Jarw - Liminal Space Succubus
Ramona Lapiedra - Just a One Diary of a Nymphomaniac Page
Veronica Leal - The Anal VVitch: A New-Colombian Folktale
Lola Danger - Things of Desire
Released: August, 2025

They had agreed to meet, but he never showed up. Maybe he had simply forgotten, or maybe he wasn’t as thoughtful as she had hoped. While she waited, her mind wandered, and she started to imagine ways she could show her disappointment. Her thoughts drifted so far that she even wondered if she should never have given him a chance at all. In the end, it didn’t really matter, because it was only in her imagination.

VR Cosplay X - Lucy Foxx

Lucy Foxx - Mario Kart World A XXX Parody
Released: August 23, 2025

Here we go! It's a-time for some Luigi number one action with the phenomenally beautiful Lucy Foxx as Princess Daisy in the cosplay VR porn from VRCosplayX. 3... 2... 1... It's time for lift off as you head down to see your beloved Princess and ask her if she'd like to race with you. She's everything Peach isn't - outgoing, energetic and bold. She takes no prisoners, and that's why you like her. When you head down to ask her about the race, you're almost certain she'll be into it - and lucky you... she is!

Digital Playground - Chantal Danielle

Chantal Danielle - Locked Up
Released: August 18, 2025

In the far future, rebellious Chantal Danielle has been cuffed and locked in a prison cell that resists all her attempts to breach the barrier. She's gotten bored of pacing when the guards throw inmate Mazee in with her. The only thing worse than being locked up is locked up with a whiner, so Chantal tells Mazee she needs total silence and a good fuck, and he's happy to oblige. Chantal sucks him, then snaps her cuffs so she can put him right where she wants him as they fuck all over the cell. Chantal wears him out, and after he cums on her face, she finally gets some peace and quiet!

Girls Way - Lana Smalls & Scarlet Skies

Lana Smalls & Scarlet Skies - Escape From Camp Conversion - Chapter 3
Released: July 31, 2025

In Chapter 3 of Escape From Camp Conversion, our group of lesbian captives have set a plan in motion to finally break free from their shackles. During one of their morning exercises, Jenna (Octavia Red) has smuggled a phone outside, waiting for the right moment to steal away from the watchful eyes of her three monstrous counsellors: Victoria, Marcy, and Lynn (Charlie Forde, Codi Vore, and Cami Strella).

Breeding Material - Scarlett Rosewood

Scarlett Rosewood - Please, Lord, Let Me Serve My Stepdaddy's Every Need and Give Me His Seed
Released: July 28, 2025

My stepdaddy has been in prison for so long, I know he needs a good snack, and I'm here to serve him, hoping that the Lord will let me take care of all of his desires. Last night, he heard me praying for him and confessed that what he needs is to fuck a woman. Maybe it was the way he grabbed my tits as he said it or the fact that he said he wants to raise a baby with me, but either way, I'm going to keep my promise. I'll do anything to give him what he wants. If what he needs is to cum inside me and get me pregnant, then I'll suck his cock until it's hard enough and let him shove it inside me until he's ready to give me his seed.

Nick Marxx - Nina Dolci

Nina Dolci - Mob Boss Prison Bae - E201
Released: July 16, 2025

Mylfed - Sophia Locke & Selena Love

Sophia Locke & Selena Love - Vi Fucks Little Caitlyn Raw (Arcane Parody)
Released: July 9, 2025

After breaking Jynx free from prison, Vi laments her mistakes when Caitlyn comes to her rescue. With a war upon them after being on opposite sites of the fight for years, they’re sexual tension grows stronger by the second, knowing this might be the last opportunity they get to be together. Vi needs to have her, and Caitlyn needs to be hers. As they embrace and explore every inch of each other’s bodies, Vi prepares her strapon to pound her little lover’s pussy harder than it’s ever been fucked in her entire life.

Mommy’s Little Man - Jayne Doh

Jayne Doh - Dirty Jane
Released: May 10, 2025

Parker, a rebellious and unruly young man, is enrolled in the controversial Scared Straight program, aimed to deter juvenile delinquency by exposing troubled youth to the harsh realities of prison life. Parker arrives at the correctional facility with a defiant attitude. The program coordinators assign him Dirty Jayne Doh, the most notorious and feared inmate in Cell Block 69. Jayne, a hardened criminal with a reputation for manipulation and endless sex drive, agrees to participate in the program as part of a twisted deal with a corrupt guard.

XL Girls - Alisha Brooke

Alisha Brooke - Alisha Brooke & Zack Whiter Get Busy
Released: May 2, 2025

Alisha Brooke won't need handcuffs to get Zack Whiter ready to enjoy her, not with that body, those big tits and Alisha's pretty face. She had him the first time she laid her eyes on him, and Zack was boob-drunk from the start when he spied her. She keeps him her prisoner in bed ... like he's going to try to run out the door? No way. Not with this busty baby. Alisha does a sultry striptease, peeling off her pink mesh top, black skirt and pink bikini. She lifts up her bikini top to show Zack her mouthwatering tits topped off with big, brown areolae and prominent nipples. Alisha rewards Zack for having the kind of big dick she loves with a juicy blow job. She has a very talented mouth. Alisha squishes his bone between her soft breasts,…

Deeper - Lulu Chu

Lulu Chu - Hanging On The Telephone
Released: April 24, 2025

A convict in a women's prison has a way of twisting men around her finger so they'll indulge her in everything she can't get on the inside.

Divine Bitches - Jewelz Blu

Jewelz Blu - Your Worst Nightmare
Released: April 23, 2025

Jewelz Blu might be your dream girl, but for Fuck Buck she’s his Nightmare Domme who’s going to use all her favorite BDSM toys to torment her newest prisoner. After falling asleep one night, Buck finds himself trapped in bondage and locked in chastity by this indigo-haired sleep paralysis demon who proceeds to tease and tickle his feet, spank and flog his ass, and make him regret getting those nipple piercings with a mean set of chain clamps. Once she finally frees him, he’s repositioned and his mouth is put to use pleasuring his Goddess and, of course, lubing up her giant blue strap-on! He takes her cock like a good servant should, but gets too excited and can’t help cumming without permission. Naturally, this calls for a much harder, rougher fucking—and once Goddess Jewelz feeds Buck his own cum, she makes him eat her pussy until he’s hard enough to fuck so she can squirt all over his chest.

Conor Coxxx Clips - Lacey London

Lacey London - Starfire - Erotic Revenge
Released: February 10, 2025

Just a few years ago, Starfire (Lacey London) apprehended the evil scientist, Dr. Mayhem (Peter Fitzwell) for his crimes associated with a futile effort to conquer the world. The evil scientist has now escaped prison, and his only thought is vengeance. Starfire teleports and arrives at the villains lab to discover him, sitting and plotting. He has been waiting three whole years for revenge, and now she has fallen into his trap. Dr. Mayhem now has the perfect plan to subdue Starfire with sexual pleasure. How will our sexy ebony superheroine fare against this vengeful nemesis? Watch to find out!

Blacks On Blondes - Coco Lovelock

Coco Lovelock - A Product Of The System
Released: March 14, 2025

Meet Coco Lovelock. A product of the system. She had grown up in juvenile detention centers her whole life so by the time she was finally released from prison she had nowhere to go but the streets. Her parents sure didn't want her back and she could not find a good job. Now 19 years old with no real life skills she was cold and lost. Couch surfing only gets you so far and she was sick of the loser boyfriends she hooked up with. There had to be something for Coco. She was young. She was hot.

Brazzers Exxtra - Cherie Deville

Cherie Deville - Twelve Horny Men
Released: March 7, 2025

Cherie Deville is found guilty of a minor crime and sentenced to 24 hours in prison. Having never gone that long without sex, she panics and seduces the all-male jury into dominating her! One last sloppy gangbang before she’s locked up!

Brazzers Exxtra - Ryan Reid

Ryan Reid - Ex Con Gets His Meat Beat
Released: February 26, 2025

Ryan Reid has been chatting with a prisoner, JMac, whom she has never met but the phone sex has been great! Ryan loves how controlling and dominating JMac is, and when he's released, he comes to her house and gives her a taste of the real thing with a rough fucking!

Freeze - Merida Sat

Merida Sat - Interview With A Thief
Released: February 25, 2025

Merida Sat enters a high security prison. She is there to interview an infamous thief, Steve Q. Merida details that Steve had stolen billions of funds from multiple locations in an impossible amount of time. When authorities searched for the money, they were only able to find one gold coin.

In an effort to get the convict to talk, Merida gives the coin to Steve. Merida doesn’t realise the consequences of this action. Steve demonstrates how he did it, flipping the coin and freezing time. He torments Merida, using her body for his own personal pleasure whilst she remains frozen. From the interviewer’s perspective, Merida doesn’t catch him doing anything but feels all of his actions...

Alt Erotic - Titi Ramone

Titi Ramone - Prisoner Titi Ramone Gets Interviewed By Detective
Released: February 20, 2025

Prisoner Titi Ramone gets interviewed by Detective Jason Sarcinelli

Deeper - Angie Faith

Angie Faith - Allegory Of The Cave
Released: February 20, 2025

A vision of natural beauty and lust drives a prisoner out of the darkness for an encounter that's anything but platonic.

Team Skeet Labs - Ava Sinclaire

Ava Sinclaire - Behind Bars
Released: February 18, 2025

Ava's time in jail has not been easy. She has to deal with an uptight prison guard who is crazy for power. Even asking to make a simple phone call means she's gonna have to do anything he wants her to. This time, he has a special request: One of the other inmates wants to meet her, and he's been really lonely and horny in prison, so he needs to release everything he's been keeping. If she wants to make her precious phone call, she needs to let him fuck her brains out, and the pervert guard will watch to make sure everything is exactly how they want it to be.

Fake Taxi - Thayana Babyy

Thayana Babyy - Huge Tits do the Talking
Released: January 26, 2025

It was just another day driving around in the Fake Taxi when I picked up smokin’ hot Colombian Thayana Babyy. The raven-haired stunner told me that she’d just been released from prison! I was attracted to the sexy jailbird, so I pulled over and joined Thayana in the back of the cab, where she showed me her huge boobs! After being locked up in prison for so long, the voluptuous nympho was feeling extra horny, and she was soon deepthroating my cock, and then she treated me to a titwank! Wanting to fuck, Thayana pulled aside her thong and took a missionary-style pounding before hopping on top to ride me in cowgirl, giving me a fantastic view of her big, juicy bubble butt as it bounced up and down! To finish, I banged the pierced babe from behind in doggy, and then she jerked me off until I spunked a load on her tongue!

Futanari - Black Angel & Sata Jones

Black Angel & Sata Jones - Cellmate
Released: January 10, 2025

Black Angel is having a miserable time in prison. Despite belonging to one of the most powerful families in the criminal world, they keep her locked up without ever telling her when she’ll be released. What’s worse is she has to deal with her cellmate Sata Jones constantly pestering her.

Device Bondage - Vanessa Vega

Vanessa Vega - Pain Slut Vanessa
Released: January 6, 2025

Vanessa Vega is back on Kink.com to get roughed up by Eli Cross. Vanessa stands with her arms bound to a post, gagged and collared. Eli kneads her tits then tenderizes her thighs with some rapid slapping. Eli hits her tits with his hands and then gets a long leather paddle to work on her thighs again. After checking Vanessa’s pussy for approval, Eli moves on to cane her with some gusto, marking his territory. After leaving a grid of welts on Vanessa’s thighs, Eli treats her to her first wedgie, and then rewards her with the Hitachi.

VR Cosplay X - New October & November 2024 Updates

Sarah Arabic - What We Do In The Shadows A XXX Parody
Lexi Love - The Gilded Age A XXX Parody
Raven Lane - Arcane Vi A XXX Parody

DFX Homewreckers - Sophia Sterling & Angelica Raven

Sophia Sterling & Angelica Raven - Sophia Sterling And Her Step-Mom Angelica Raven Can't Resist a Rocking Hard Cock
Released: November 16, 2024

Well Sophia Sterling went and did it again. This little 18 year old slut has been off fucking around sucking dick all over town and her father found out. One guess who is grounded again. Sophia even has her stepmother, Angelica Raven watching to make sure she does not go out and get into more trouble. This is like being in prison to a horny little girl who just needs her teen twat fiddled with. Finding herself alone, Sophia sneaks her boyfriend Lawson Jones into the house.

Deeper - Angie Faith

Angie Faith - Conjugal
Released: November 14, 2024

A churchgirl pays a visit to the prisoner who assaulted her fiance.

Mature 4K - Laura Red

Laura Red - Women's Prison Showers
Released: October 15, 2024

The tougher the gangster, the more preferential treatment he gets from the prison authorities. Some have a TV set in their cell, others have the opportunity to eat fresh lobster for lunch, and some boast of gold jewelry, but none of them can compare to the hero of this story. His influence is great and his power extends beyond the borders of prisons and states. Today is his birthday. And to really brighten up the celebration, the warden has ordered him to be taken to the women's showers…

Piss Play - New 2024 Updates

Dolly - Drinking Strangers Piss
Casey Calvert, Kira Noir & Cadence Lux - Casey And Friends
Nuria - Kinky Straws
Casey & Lydia Black - Piss Play
Piss Play - Piss Goggles
Dolly - BBC For Dolly
Casey & Charlotte - Charlotte Gets Used And Abused
Nuria - The Public Urinal

Futanari - New August 2024 Updates

Black Angel & Fanta Sie - Keep Out
Amirah Adara & Veronica Leal - Futa Dream
Hot Pearl & Tiffany Tatum - Disciplinary Action

Sex Mex - Anai Loves

Anai Loves - Imprisoned
Released: August 25, 2024

Anaí Loves, the hot Colombian who was put behind bars for exhibitionism in another city. Locked up in a local prison, her only way out is to convince one of the guards, the attractive and reserved Officer Ruiz, that she deserves a second chance. She seduces him and fucks him.

Voodooed - Rikako Katayama

Rikako Katayama - Prison Lawyer
Released: July 9, 2024

Amirah Adara is waiting for her lawyer in her prison cell. But Rikako Katayama brings some bad news for her... Instead of a shorter sentence, the judge ruled an extra 20 years for her! Amirah gets really upset that her lawyer screwed things up so badly, so she takes out her voodoo doll and uses its magic on Rikako...

Fake Taxi - Nuria Millan

Nuria Millan - Straight Outta Prison
Released: July 17, 2024

The other day, sexy brunette Nuria Millan hopped into my cab and asked for a lift into the city centre. As we set off, I got chatting with Nuria, who told me she’d just been released from prison! The hot Euro confessed she’d been caught having sex for money, and then she offered me her services in exchange for a free ride! After parking the Fake Taxi, I joined the cute jailbird in the backseat, where she helped herself to my throbbing erection, and then she treated me to a titwank. Following an incredible deepthroat blowjob, the Spanish beauty moaned loudly as she bounced her tight pussy on my big cock before spreading her legs and taking a missionary fuck. Afterwards, we did some spooning, and then Nuria stuck out her nice round bum and invited me to bang her from behind doggystyle until it was time to cum on her tongue!

Voodooed - New June 2024 Updates

Clemence Audiard - Weather Girl
Veronica Leal - Prison Guard
Eden Ivy - It Support

Futanari - Barbie Rous & Ashby Winter

Barbie Rous & Ashby Winter - Prison Temptation
Released: May 17, 2024

Ashby Winter sat in her lonely cell, her mind consumed with thoughts of lust and longing. It had been far too long since she had felt the warmth and touch of another human being… As she waited, her prison guard, Barbie Rous, made her routine rounds, checking on the inmates. But when she approached Ashby’s cell, the unexpected happened… As Barbie approaches Ashby’s cell, the inmate suddenly undergoes a futa transformation and she grows a huge futa cock!

As lonely and craving as her inmate, Barbie is filled with lust. Unable to resist the temptation, she gets on her knees and starts sucking on Ashby’s hard cock. After she is done, she quickly unlocks the cell door and they both start undressing. Their moaning fills the cell and they start fucking hard until Ashby finishes with a massive facial on Barbie.

Fake Taxi - Matty Mila Perez

Matty Mila Perez - Prison Release Day Fuck
Released: May 6, 2024

Today in the Fake Taxi, I picked up hot brunette Matty Mila Perez for a lift into the city centre. During the ride, I found out that she’d just been released from prison! She was pretty cute for a jailbird, and when she told me how horny she’d been, I felt my cock getting hard with desire. The naughty minx started touching herself while I found somewhere quiet to park, and then I hopped in the backseat and licked her pierced pussy.

Brazzers Exxtra - Romi Rain

Romi Rain - House Arrest Hottie Works The Penal System
Released: May 5, 2024

Hot body babe Romi Rain is released from prison, but she’s not granted total freedom. Instead, she’s guarded by cop Mick Blue in her home and forced to wear a house arrest ankle bracelet. As soon as Romi’s alone, she’s thinking about one thing: cumming. She gets to work with her wand when Van Wylde, her badass bf who just broke out of jail, shows up to surprise her. Excited to show off her new ankle jewelry, she gives Van a footjob and move quickly on his cock, fucking like she wants to get caught.

Exploited College Girls - Trinity

UPDATED Trinity - Passionately Rough Me Up
Released: October 5, 2023

Holy Mother of All Fucks everyone because today’s exploitee is 18 year old Trinity and I’ve never seen a girl get so much attention, so fast, as today's future superstar Trinity. She’s special alright and here to take two Dicks at once for the Very First Time. Love it, and if you’ve seen her absolutely scorching First Sex on Camera over at excogigirls.com entitled: “I Like Girls More Than Guys” with Amber Moore and her First Cock on Camera here entitled: “The Red Pill. Loved All Of It” then you know she took the Red Pill and she’s on her way to unlocking her suppressed Sexual Desires, and Threesomes she declared are A Big Leap for her.

Female Fake Taxi - Lady Gang

Lady Gang - The Prison Release
Released: March 13, 2024

Today in the Fake Taxi, I picked up a handsome chap who had just been released from prison. Since he had been stuck in jail for a long time, he was feeling really horny and looking to fuck someone. I offered him my services, and while I found somewhere quiet to park, he got his huge dick out! I joined the dark-haired stud in the backseat, where I took the full length of his hardening cock in my mouth, treating the ex-con to a sexy blowjob! Afterwards, I bounced my tight pussy on his lap cowgirl-style, and then I spread my legs and moaned in euphoria as the stud licked my lips and clit before banging me in missionary. I rode his cock some more while he spanked my curvy ass, and then we spooned in the back of the cab until he spilled a thick load all over me!

Parasited - Emiri Momota

Emiri Momota - Emiri's Adventures
Released: July 16, 2023

Emiri’s Adventures include 3 crazy parasited adventures for Emiri Momota!

Warning: The 3rd video contains graphic scenes that may be disturbing or unsettling to some viewers. Viewer discretion is advised.

Adventure 1

Emiri Momota is lying in her comfortable bed, enjoying the silence when suddenly she feels something slimy crawling on her body. The alien parasite slides inside her pussy and a few days later she wakes up in a prison cell. The parasite’s influence makes her crave extreme sexual pleasure and she starts to masturbate.

A prison guard checks on her after hearing hear moan loudly. Unexpectedly, Emiri pulls the guard closer, cuffs him to the bars and starts giving him a sloppy blowjob. She sucks him dry, extracting all of his energy until he falls to the floor. Emiri stands next to him and mounts his dick, riding him until he explodes with a huge load of cum inside her...

ExCoGi Girls - Trinity Olsen & Roxanne

Trinity Olsen & Roxanne - Roxanne Sexy Tight Teenager
Released: October 25, 2023

Well October just keeps trucking along doesn’t it and when I said all treats and no tricks everyone? Well just feast your one-eyed monster’s sweat tooth on today’s treats because Roxanne and Trinity Olsen went at it today full throttle and at a take no prisoner’s approach to muff munching in this behemoth of a whopping video that’s over 2 hour and 9 minute long. I mean who wouldn’t want to lick and fool around with either one of these two, or be in between the shenanigans as they go at it in a full out assault on each other’s beautiful girly parts. And when I say beautiful? I mean spectacularly beautiful because Roxanne has one of those bodies and pink pussies that would make any father of a sexy tight teenager want to lock up their daughters if they looked like her...

Dorcel Club - Karina King

Karina King - Surprise massage
Released: October 23, 2023

Ready to do whatever it takes to free her client from prison, Karina King follows Renato to his appointment with the masseuse. Disguised, she takes the masseuse's place to execute a daring plan. Beneath her skilled hands, the air becomes charged with electric tension. Renato and Karina share an entrancing moment. The stakes are high, but the connection that forms between them is even more potent, crafting an experience as memorable as it is risky

Brazzers Exxtra - Lulu Chu & Reese Robbins

Lulu Chu & Reese Robbins - Horny Jailbird Craves Cock
Released: October 18, 2023

Reese Robbins surprises her gamer boyfriend Jayden Marcos with a prisoner costume and handcuffs, looking to turn up the heat in the bedroom. Reese can’t stop gaming though so in the meantime, Reese will have to settle for giving him a blowjob before they can get around to her roleplay fantasy. Later, while they’re away, Lulu Chu, a real-life jailbird on the lam, breaks into their home and helps herself to some pie and their comfy bed. When Jayden and his girlfriend return, they split up to look for the intruder. Jayden finds the sexy petite Lulu first and soon finds out that nothing’s hotter than having cheating sex with an escaped convict!

Futanari - Amirah Adara & Zazie Skymm

Amirah Adara & Zazie Skymm - The Prisoners
Released: July 28, 2023

Zazie Skymm is put in a prison cell, where she meets her new cellmate, Amirah Adara. Amira tells Zazie that she has been put here because she did something against her colleague’s will. Zazie is curious about what could have she possibly done to end up here, so she insists on telling the full story.

Alt Erotic - New January & February 2023 Updates

Carmen Callaway & Skylar Green - Help Nikki Hearts Get Over Her Ex
Adalind Gray & Evilyn Ink - Female Prisoners Blow A Thug
Kitana Montana - Kitana Montana Gets A Money Bag Tattoo
Martina Rose & Little Louise - New British Bombshells
Sabien Demonia & Taylor Nicole - Show Slutlana
Kitana Montana - Artistic Fuck Session

Japan HDV - Yu Ayana

Yu Ayana - Secret Prison Yu Ayana Scene 2
Released: August 3, 2023

Shoplyfter Mylf - Payton Preselee & Nova Vixen

Payton Preselee & Nova Vixen - Case No. 6615419 - A Dangerous Duo
Released: July 29, 2023

While Officer Jack is interviewing Payton, the thief he just caught shoplifting, he gets notified that there is another thief around, and it turns out it’s Payton’s stepdaughter Nova! In his quest for justice, the security guard strips them naked, finding their pockets full of stolen goods. Facing prison charges, Jack gives them an option: they can follow his command or go spend time behind bars.

Digital Playground - Luna Star, Kira Noir & Kayley Gunner

Luna Star, Kira Noir & Kayley Gunner - Machine Gunner Episode 3
Released: July 10, 2023

Alone behind enemy lines, Nikki Ransom (Kira Noir) finally has her evil ex, Riggs, in her sights. But when it comes to a firefight, Nikki has to make a retreat, hijacking the truck full of weapons and the driver, another old army buddy. Caine (Tommy Gunn) agrees to drive her to the border in exchange for some road head... but when sexy assassin Daytona (Luna Star) lies in wait for them, Nikki is taken prisoner. Meanwhile, Nikki's team ignore orders to return to base and instead go looking for her. Rena (Kayley Gunner) and Jimmy (Damon Dice) set a trap for Daytona, and neutralize the naughty assassin with a hot threesome.

Bang Bus - Ahh Dee

Ahh Dee - Heat Will Make Her Cheat
Released: July 5, 2023

Driving by what we thought was a prison we catch Dee walking. It's such a hot day here we honestly got her on the bus with just some cold water. She told us she had a boyfriend so no funny business. For a few dollars we got her to flash her tits, but the real show was her humongous ass. She pulled her tight jeans down and had just a piece of thread she called panties lost in it. Lucky Jay was here to help her pull it out. He spilled some water on her ass and while trying to help her clean it up, he tripped and his dick fell into her. Dee did not go crazy, but actually was grateful to be getting dicked down in some ac. Her pussy was good and hot. Jay painted her face, and she refused to wipe it off. If she really has a boyfriend she is going to have some explaining to do. You've seen these before so you know what happens next...vroom.

Puta Locura - Paola Hard

Paola Hard - Threesome With A Prisoner Of War
Released: July 4, 2023

Many of you may have wondered what happens in wars when soldiers take women prisoner? Well, in the vast majority of cases what you are going to see happens in this interesting recreation that our friend Magic Javi makes for us, bringing it to life some young soldiers who capture a young local woman named Paola Hard in the middle of battle, find her in her house alone, defenseless, so they approach her and throw her on their shoulders in search of a quiet place where they can release all the adrenaline accumulated in several days fighting at the front...

Digital Playground - Kira Noir

Kira Noir - Machine Gunner Episode 2
Released: June 26, 2023

Nikki Ransom and her team walk directly into a trap, but these professionals have the situation under control. After Nikki takes out the enemies, she sends the others back to the chopper, intending to scout ahead for her ex... but finds herself taken prisoner by two of his goons. Voss (Charles Dera) and Bailey (Scott Nails) tie up the hardened merc in an abandoned warehouse, but she soon has the guys hard as she talks herself out of the ropes and into the middle of a threesome... then makes her move!

Shoplyfter - Anna Claire Clouds

Anna Claire Clouds - Case No. 7906250 - Shoplifting in the Genes
Released: June 16, 2023

Anna was about to go visit her dad on Father's Day. The guy is in prison so Anna thought about smuggling some things he might need, but she got caught in the mall. Mike, the security guard that busted her, checks her background and finds out about her dad's criminal record. Anna opens up to the officer about his feelings toward his jailbird father. Mike does a thorough check and finds nothing, so he feels sympathetic to Anna's situation. He offers to let her go out without any consequences if she helps him out. Anna accepts on the condition that she can call him daddy.

Interracial Pickups - Skyler Storm

Skyler Storm - Interracial Pickups
Released: June 8, 2023

Skyler is a little whippersnapper who is always up for adventure as she likes to think of herself as a girl who is willing to take a chance. So take today for instance. While walking home from school she notices a man filming her on his phone. Hmmm, is this one of those stunt videos or is he just a creep? Either way she is going to find out and confronts him. He informs her he is taking these videos of good looking women for his friend who is fresh out of prison and under house arrest and cannot get out and see girls in person. Well if that isn't the best pick up line she's ever heard. She might as well go meet this man. After all, his name is Chocolate God and she does love chocolate. Arriving at the random stranger's pad she does indeed meet the man in the ankle bracelet who is under house arrest. Wow, her very first ex-con. Today is a day of adventure. Next thing you know she is showing Chocolate God one her little titties and asking for him to show something. Oh we all know where this is going as Chocolate brings out the biggest penis she has ever seen. Damn right she is going to suck it, otherwise this story is over right now. Soon she is sucking both cocks and getting her tight little chick whole reamed out as the dudes take turns pumping her full of sweet black meat. Now this is an adventure.

Cherry Pimps - Harley King

Harley King - Inmate Pen Pal
Released: May 30, 2023

For Harley King's college thesis, she decided to write a thesis about pen pals and she decided to be a pal to an inmate. Soon their letters got intimate and she enjoyed the idea of her fantasy coming to life, but didn't expect her inmate pen pal would show up on her doorstep! He broke out of prison just for her and she made sure to make it worthwhile for him!

Hentaied - New March & April 2023 Updates

Emiri Momota - An Alien Inside # 3
Lulu Chu - Lulu’s Adventure
May Thai & Rae Lil Black - Prison Time

Emiri Momota wakes up in a pool of slime. Her perfect body is trembling as she can feel something wrong inside her. Suddenly, a tentacle crawls out of her mouth and another from her pussy. She has an alien inside! The creature fucks her from the inside and then slowly slides back. More tentacles appear, pushing deep into her tight pussy. turning her initial fear into pleasure. The alien finishes with a huge creampie and fills her pussy with warm alien cum. The tentacles crawl back, leaving Emiri alone, covered in cum. As she is shaking from the intense fuck, she lays alien eggs!

Japan HDV - Rio Haruna

Rio Haruna - Rio Haruna gets to suck two men in the secret prison
Released: May 15, 2023

Remember that hottie Miss Rio Haruna that was in the private jail cell? She was here doing some hard time with a cock in her mouth. Just sucking away at that hard cock! She has been in for a few weeks now and she has been a very good jail girl. In fact sometimes the jailer has some of the men come down to visit her. It is usually just a few of the upper managers. But sometimes for fun he will invite a bunch of guys down to have some fun.

Hentaied - New January & February 2023 Updates

Rae Lil Black - Toilet Encounters 3
Emiri Momota - Prison
Ellie Luna & Eve Sweet - The Prisoner
Lulu Chu - Hospital
Cherry Kiss - Dangerous Mission

Japan HDV - Ria Sakurai

Ria Sakurai - Ria Sakurai is in jail and sucks some cock to get a shorter sentence
Released: April 15, 2023

One of our favorite videos and models is here today. You will remember her from her ping pong lesson many years ago. We had her pussy spread on a ping pong table after a hot lesson. Do you remember Ria Sakurai now? We have her back again today and she has fallen on some hard times and is in prison. But where she is at is not your normal prison. This is a very special one for the crimes she is accused of committing. The charges are being a working girl. Today she is being transferred to a new holding cell and the guard is taking her in.

Team Skeet X Molly RedWolf - She Fucked Her Prisoner

Molly RedWolf - She Fucked Her Prisoner
Released: April 9, 2023

Sexy anime dominatrix Molly has her submissive Danny tied and bound naked with his cock hard. Molly will play and tease Danny before laying him on the bed to ride his cock until she gets a super creamy creampie!

Hunt 4K - Kristy Waterfall

Kristy Waterfall - Dirty Story About Clean Dishes
Released: February 10, 2023

It's amazing what some people will do to avoid compromising their idiotic principles. I've heard that in some countries prisoners are willing to cut off a finger to avoid having to work. And the couple I met were disgusted with dishwashing. These two wanted to eat in the cafe and escape, but the manager caught them at the very exit. Well, I like to help people, and this time I helped two parties to a conflict at once. One got the money, the other got my beautiful cock...

Interracial Blowbang - Harley King

Harley King - Interracial Blowbang
Released: March 27, 2023

When Harley gets thrown out of her parents house (again!) she finds herself in need of short term shelter. Turning to her brother, he suggests she crash at a halfway house he recently spent time at after leaving prison. It's an all male facility but the manager owes him a favor, so Harley is offered a place to bunk. She just has to respect the rules and not cause problems. Well, being the slut she is, Harley just cannot help herself. All these men around, how could it hurt to just suck one dick.

Bangbros Clips - Kailani Kai

Kailani Kai - Kailani Kai Fucks Inmate
Released: February 14, 2023

Anything can happen at our prison. Cameras are rolling 24/7 and that gave us the idea to have fun at work. Kallani Kai is one of the guards that is having the most fun. She goes around everyday choosing a new inmate to fuck. She loves getting wild and she loves sampling the new meat that get sent to our prison. This particular time, after a fresh batch of newbies comes in she decides to single one of the out. The nerdiest looking one. She pulls up to his cell and gives him an offer he can’t refuse. This dude fucked Kallani in several different positions making her cum several times all over his cell. Eventually, he cuts all over her face. Now it’s time to get dressed and pretend none of this ever happened.

BarsAndStripes.com - SITERIP

BarsAndStripes Full Siterip
599 Videos | 18.21 GB

The only prison where bad girls pay the price for their crimes. All are punished harshly. Spanking, caning, paddling, strip searches & medicals.

XL Girls - Gina George

Gina George - Gina George & The Anal-ist - Remastered
Released: January 2, 2023

Creamy English tart Gina George gives up her soft, round British butt when she goes to see The Analyst, a man who appreciates a big pair of tits. A woman of lusty tastes and appetites, Gina brings The Analyst's head between her big boobs. He licks and kisses Gina's bra-created mounds to her delight...

Sis Swap - Gaby Ortega & Krissy Knight

Gaby Ortega & Krissy Knight - Fugitive Swap
Released: January 1, 2023

Best friends Gaby and Krissy are reminiscing about their stepbrothers Victor and Nicky who’ve been locked up in jail for a while. The girls realize they miss their stepbrothers and it turns out they had just escaped prison and were heading their way! Nicky and Victor sneak in and find their stepsisters sitting on the couch, and they realize they’ve grown up a lot since the last time they saw them. They also haven’t seen any women in years so when they give their respective stepsisters a hug they get huge boners! Gaby and Krissy take pity on them and decide to swap their stepbros and finally give them what they’ve been craving for so long!

Pure Taboo - Kenzie Taylor

Kenzie Taylor - Her Guilty Secret
Released: December 27, 2022

Sara (Bella Blu) is talking with her parent, Sadie (Kenzie Taylor). They're awaiting the arrival of Sara's boyfriend, who Sara has been dating for a few weeks. This will be Sadie's first time meeting the boyfriend, although Sara says she's already told him that Sadie is a prison warden - in fact, he's been making jokes about what it would be like to have a prison warden for an in-law...

Porn World - Alisha Martinika

Alisha Martinika - Busty BDSM Cop Alisha Martinika Lets Stud Loose For Anal Destruction
Released: December 14, 2022

BDSM police officer Alisha Martinika only has one thing on her mind and when she manages to capture sexy criminal Tim she locks him in her dungeon to use as her own personal plaything. Alisha teases him by stripping and masturbating as he watches from behind bars and this filthy blonde toys herself with a glass dildo to make Tim seriously hard. She heads over to his jail cell and sucks his cock through the bars before he fucks her from behind. This busty blonde sets her prisoner free and Tim demolishes her pussy and ass with his thick shaft! Alisha kneels down and licks his balls before he showers her in a messy facial!

Digital Playground - LaSirena69, April Olsen & Roxie Sinner

LaSirena69, April Olsen & Roxie Sinner - Wasteland Ultra - Episode 3
Released: November 21, 2022

After Officers Vennix and Laredo pull up to the firefight, it's anybody's guess how it will go down. Inside his warehouse, Duke (Scott Nails) tries to keep the Synthetics (Roxie Sinner, LaSirena69) safe... and they're starting to get overloaded and ready to blow. He'd better let the horny robots use his dick to burn off their excess energy. Meanwhile, out in the Wasteland, the bounty hunters bring prisoners Dexter (Van Wylde) and Officer Laredo (Isiah Maxwell) back to their outpost for warlord Ruin (April Olsen) to deal with... but the men are shocked to learn she's a Synthetic too! After sucking and riding Dexter's dick, the insatiable conqueror unties them both to get just what she wants: a hard spit-roast.

Glory Hole Secrets - Nova Vixen

Nova Vixen - Nova Vixen's First Gloryhole Video
Released: November 11, 2022

Nova Vixen starts off with a bang during her face off with these anonymous cocks. She may look quiet and reserved with her clothes on, but let that bangin' body out of its cotton prison and there is a sex goddess underneath. Nova is ready to suck some cocks and double up her numbers today. She is about to pump her stats significantly today as the throng of anonymous strangers on the other side of the wall load her throat full of cum. She does not discriminate when it comes to putting dicks in her mouth; she loves them all. Nova also has no cock type preference. She just wants as many as possible in her mouth as soon as possible. That moment is going to come very soon for Nova, just like most of her faceless men will. She rates herself a "8.5" on the cock-sucking ten-scale, but you'll have to watch her video to see if she lives up to the hype, then comment below about what you think. Should Nova come back to suck more cocks again in the booth, now that she has had a taste of the gloryhole action? That's all up to the members to decide.

Team Skeet Classics - Piper Perri

Piper Perri - Reunited With His Big Black Cock
Released: October 31, 2022

This Team Skeet Classics update features Piper Perri and Asante Stone. Originally released Sept 25th, 2015, this Teens Love Black Cock scene was and still is a major hit! Tiny blonde Piper has been writing back and forth with her prison pen pal Asante. Piper tells him that she can’t wait for him to get out so that she can finally get fucked by his huge black cock!

Analized - Jodi Taylor & Dana Vespoli

Jodi Taylor & Dana Vespoli - Evil Stepmom Fucks Her Ass
Released: October 1, 2022

Punishments from people with a ‘step’ in front of their titles might sound bad but it’s actually really, really good, in cliché porn plots, at least. If you know what we’re talking about, you saw some good shit in some point of your life. But this scene might give you the same setting but fresh plots. Come around, lads. Dana Vespoli is gonna sodomize Jodi Taylor as a form of “disciplinary action” using fake dicks and some toys in a prison cell. Well, this starts as a normal step mom and step daughter serious talk...

Dorcel Club - Alessandra Jane & Lola Bellucci

Alessandra Jane & Lola Bellucci - Intimate Friendship
Released: September 19, 2022

When you're in prison, all you can think about is getting out. But now that Clea is back to her normal life, she feels abandoned and doesn't recognize anyone but Steve. But on his side, he didn't waste his time and took advantage of it with Clea's friends.

Sex Mex - Pamela Rios

Pamela Rios - My bussiness partner's hot wife
Released: September 12, 2022

My business partner was sentenced to prison for 20 years. Someone will have to take care of his hot wife, Pamela Ríos.

Behind The Mask

AdamAndEve.Behind.The.Mask.XXX.1080p.WEBRip.MP4-VSEX
Cast: Avy Scott, Cherokee, Jana Cova, Jesse V, Kody Coxxx, Melody Max, Teanna Kai

What really goes on at the secret masked meetings of an elite society? One woman dares to find out! Baring body and soul but not her face, she gives in to total sexual submission. Is this a world a taboo prison of the mind or is it the bodies ultimate freedom? Judge for yourself as we take you Behind The Mask!

Model Media US - Madi Collins

Madi Collins - Real POV Adventures: Bad Cop, Hot Prisoner
Released: June 22, 2022

Sex Mex - Connie Garcia

Connie Garcia - Lustful Thief
Released: August 18, 2022

An escaped prisoner breaks into spinster Connie Garcia's home and finds her flicking the bean. The petty thief seizes the opportunity to fuck a woman after a year behind bars.

Penthouse Gold - Roxanne Hall

Roxanne Hall - Roxanne Hall's Hot Sex In A Jail Cell
Released: August 5, 2022

It's prisoner Scott Styles' lucky day as sexy sheriff Roxanne Hall pays him a super hot and heavy visit in his jail cell. The busty blonde just can't wait to get her clothes off and feel his hungry mouth on her big tits and huge dick deep inside her horny pussy. The naughty nympho just can't get enough of the stud's monstrous cock, first riding him in cowgirl, giving him a blowjob to get him even stiffer, and then getting pounded until he busts a cumload on the Penthouse star's shaved snatch.

Missa X - Kylie Rocket

Kylie Rocket - Watching Porn with Kylie Rocket
Released: May 11, 2022

Jacob (Chris Epic) has an argument with his wife Helen (Ryan Keely) after she catches him watching porn on his laptop. "I love you, okay? It's totally normal to watch porn. I don't know a single guy who doesn't", he claims. "Am I not enough for you? Do I not do it for you anymore?", Helen asks.

Glory Hole Secrets - Lizzie Love

Lizzie Love - Lizzie Love's First Gloryhole Video
Released: July 22, 2022

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 Lizzie Love in her FIRST GLORYHOLE EVER. She may look quiet and reserved with her clothes on, but let that bangin' body out of its cotton prison and there is a sex goddess underneath. Lizzie is ready to suck some cocks and double up her numbers today. Before her interview finished she tells us a secret and says she has only ever sucked 12 dicks. She is about to pump her stats significantly today as the throng of anonymous strangers on the other side of the wall load her throat full of cum...

Pure Taboo - Scarlett Mae

Scarlett Mae - Nothing To Lose
Released: May 3, 2022

NOTHING TO LOSE

Beth (Scarlett Mae) is home alone when her doorbell rings. She's a little confused but then shocked when she opens the front door to find a nervous-looking man, Simon (Lucky Fate), standing there. Although Beth is about to close the door in his face, he pleads with her to let him in...

Once Beth begrudgingly lets him in and they sit down, it's revealed that Simon is Beth's ex, whom she hasn't seen in many years. Of course, she gets another shock to the system when Simon says that there is a warrant out for his arrest and that he is facing a long prison sentence. Although he's been on the run, he knows he's in the wrong and is ready to turn himself in. But before he does that, he wants to have one last night with her since they've always had a special bond...

Digital Playground - Karma RX

Karma RX - Breaking Out
Released: April 18, 2022

Inmate Harley (Karma Rx), a hot and badass crime boss who’s been recently incarcerated, plans on making a quick escape from prison by seducing a prison guard (Oliver Flynn) and convincing him to help her break out. However, they’ll have to settle a couple of scores with the head prison guard and her rival cellmate before they can make their getaway.

Wicked - Kenzie Taylor

Kenzie Taylor - Deranged - Scene 2
Released: January 14, 2022

Dr. Charlie Hayes (Kenzie Taylor) has an agenda and though the prison's warden, Marc (Derrick Pierce), can see right through it, he can't resist her feminine wiles. She wants the Curwin case, and she'll do whatever it takes to get it.

Debt 4K - Sata Jones

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?

Brazzers Exxtra - Audrey Madison

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.

Hot And Mean - Victoria Cakes & Clara Trinity

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.

Facial Abuse - Rebel Rhyder

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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