Family Roleplay (67)

After discovering Principal Mountain is a perverted master of deception, school reporter Melody Marks launches a private investigation into his character and past dealings. As part of her ongoing investigation, Melody breaks into his office and discovers a set of mysterious tapes locked in his desk. Our fearless little reporter starts going through them and the first piece of the puzzle sees Mr. Mountain passing as a security guard making a shady deal with a teen shoplyfter after she gets caught. This girl in the video is so fucking great at sucking and riding the Mr. Mountain's dick, that Melody can't help but pull her panties to the side and rub her delicate fingers over her wet little pussy. It seems that she's just as naughty as those Shoplyfter girls...

VHXXX Part 1: Loss Prevention Officer '92

As a loss prevention officer, I've learned to wield my power, and all these girls who shoplift from our store know it. When Krissy and Sasha sat in the back office, dressed in their revealing Luau outfits, I knew they were no exception, no different from all the other girls in this exact situation. I've done this a million times and knew they'd fold in no time if they wanted to avoid jail. But I'm not just some freak - I can tell these girls love finding their submissive sides. They've never been fucked by a real man or have had to submit to authority. Getting fucked in these situations, they feel so dirty, so raw, so fucking invigorated by the absolutely vulnerable position they're in. They discover an entirely new side to themselves - I am just the one who helps unlock that side of them. Naked and bent over the table, I spread their pussy lips wide, searching with my fingers as deep as possible They started to squirm, their eyes flashing with hatred, but I could see they also were fascinated and turned on. I made them suck my cock, slowly at first, their lips wrapped around it with a mixture of reluctance and curiosity. But as I pushed deeper, their inhibitions started to fade, and they began to satiate a primal lust they never knew they had. Soon, they started to move faster, their tongues dancing around the head. A simple blowjob isn't enough to get off the hook - a lesson I knew I had to teach them... As they bounced on my cock, their bodies began to tremble, their moans filling the room. They were lost in the moment, their submissive sides taking over. I've seen it time and time again - girls who think they're above this kind of thing, only to discover a deep-seated desire to surrender to carnal instinct - letting the power figure take the lead, relinquishing control. And I'm always happy to be the one to unlock that side of them.

Case No. 8003607 - Lu`Au Gone Wrong

Hazel never imagined what stealing a dildo from the mall's sex shop could cause. The young school girl, tired of being teased for being her class' miss goody two-shoes, decided to take matters into her own hands and pop her cherry with a sex toy. Unfortunately, she didn't have one and figured she had to do it right. At the sex shop, she reached for the biggest and thickest plastic dick on the shelf and tried to make a run for it, but security guard Jack Vegas caught her with ease, taking the naive gal for questioning. She was already in so much trouble, so she could barely talk while the officer patted her down. His firm hands certainly ignited sensations she had never felt before. The patdown evolved into a thorough cavity search, a security measure that felt more like a first time for Hazel. Feeling equally scared and aroused by the situation, she heard Jack's instructions eagerly as he explained he had to press charges unless she did something for him. The officer had always wanted for someone to suck his cock while handcuffed, another new for Hazel. Without other options and with a bit of expectation, Hazel turns Jack's fantasy into reality, knowing that this will only be the first part of their naughty deal.

Case No. 8003420 - Take My Pussy, Officer

I know I fucked up, but I never thought I'd be fucking my older step-sister with some stranger in the back of a department store. It all started when I tried stealing some sex toys. It was part of a school ritual, and I really wanted to prove myself. But things got out of hand, and when I was caught shoplifting, I knew I was in deep trouble. My only thought was to call my older step-sister, Hadley. Of course, she was furious but willing to do anything to help me. And I was willing to do anything to get us out of this situation. The loss prevention officer gave us an ultimatum - my step-sister and I play with each other's pussies, he fucks us, and we walk free. Losing my virginity like this was not how I pictured my first time at all... As wrong as all this is, is it weird that I was excited?

Case No. 8003592 - The Desperate Virgin Thief

Liz, a young and idealistic college student, is staging a protest against the mall's dress code policy, specifically their "no promiscuous clothing" rule, after being removed from the premises for her attire. In an act of defiance, she returns to the mall, wearing barely anything and carrying a sign that reads "Free the Nipples," challenging what she views as an unfair and restrictive policy. This doesn't sit well with Officer Mancini, who is just trying to do his job and can't have a noisy teenager chasing customers away from the wall with her vandalism. Now in Mike's office for questioning, Liz tries to talk her way out of the situation, but her irritating attitude prompts the security guard to do a thorough cavity search in search of any dangerous items. When Mike's hands reach for Liz' pussy, he realizes how tight and closed it is. Concerned about the little student's future, he offers to let her walk away a free woman if he gets to free her pussy first. The young activist realizes that she actually needs the Officer's creamy blessing much more than any protest to liberate herself from oppression.

Case No. 8003589 - Free The Pussy

Shoplifting gives juvenile delinquents all sorts of creative opportunities to try and snitch items in the most unsuspecting ways. Take Lucia, for instance. This cute skater girl has been experimenting with sex toys lately, and she had the unfortunate idea of attempting to take a dildo from the small by hiding it behind her board. Officer Fitzwell didn't find Lucia's idea very original and caught her easily. The nervous look on Lucia's face made Peter feel strong, asserting his dominance by stripping Lucia naked and conducting a thorough cavity search. This act of power secretly made Lucia aroused, but she had to keep her face straight if she wanted her plan to work. The sensation of Peter's hands on her private parts was exhilarating, but Lucia remained calm while the search occurred. Eventually, Officer Fitzwell noticed the dildo behind Lucia's skateboard and her plan crumbled down instantly. Still, the security guard tried to be sympathetic to the skater's sexual awakening and offered her a deal: rather than sitting on the dildo of her board, she could use the officer's cock to see what actual meat inside her pussy feels like...

Case No. 8003494 - Skater Babe Pays Her Dues

Case No. 8003422 - Matching Outfit Thieves

It's Chinese New Year and young Alexia is feeling wild! The girl went into the mall and tried to steal a beautiful lipstick she noticed in the store. What she doesn't know is that she was actually being watched and that the object she stole was really a vibrator. But this is not important now, as she has to answer Officer Pounder's questions if she wants to walk away a free woman. Unfortunately, Alexia tries to play dumb-the worst decision she could make with the security guard. Now, she has to go through all of Will's kinky security checks to prove she hasn't taken anything else. The future is not looking bright for Alexia, who is in the middle of a sticky situation and might have to face theft charges. Will, however, is not an insensitive guy. He is happy to let this one slide if she can do something for him. It is very simple: all it takes is a little preview of how the vibrating lipstick works...

Case No. 8003415 - That Doesn't Paint Lips, Babe

These stepsiblings thought they could run away from boot camp to destroy the mall on Memorial Day, but they didn't know what type of security guards would catch them. Making a deal with one guard is one thing, but ensuring that three of them let you go is not easy, and it will require giving them whatever they want. These stepsiblings are willing to do anything. She'll suck all four dicks in the room, including her stepbrother's, and he'll pound her pussy in front of everyone else while they jerk off. The stepsiblings might be able to fuck their way out of trouble, but nobody is leaving until her face is covered in all of their cum.

Case No. 8003813 - Memorial Day Gangbang

In a crowded mall, Aria slipped some items into her bra, hoping to conceal it from the prying eyes of the store's security cameras and staff. London Ford, the mall's vigilant security guard, immediately noticed something was wrong, so he quickly moved to intercept her. As Aria attempted to exit the store, London blocked her way out and gave her no choice but to follow him to his office. The questioning began and Aria failed to explain why she had so many unpaid items with her. Eventually, London was forced to strip the girl naked to make her come clean about stuffing her bra with merch. As Aria grew nervous, London decided to change his game and play the good cop to give her a chance to redeem herself. Her perk little tits had caught his eyes and he just wanted a little release from his stressful job as a security guard. Aria soon understood that her best way out of this situation was showing London what her beautiful boobs and her young yet powerful pussy were capable of.

Case No. 8003680 - Bra Stuffing Brat

Asteria and Rhae wanted to do something naughty for their boyfriends, so they went to the mall to steal some sexy outfits to surprise them. They ended up at the Halloween store, where they found the sexiest little bunny costumes, with deep cleavage and fishnet stockings. They thought they had it, but Officer Rebel caught them just before they could get away. Asteria and Rhae know they’re screwed, but they also know they can get out of it… after all, they’ve been fucking cops and security guards to get out of trouble ever since they turned eighteen. Who could resist these little sluts together? Officer Rebel certainly won’t, and these slutty bunnies are about to milk his cock for all its worth.

Case No. 8003683 - Two Slutty Little Bunnies

Jason never knows what will happen during his shift. As the mall’s security guard, he is constantly forced to detain young delinquents who think they can get away with shoplifting, but there’s never a dull moment when he is on duty. The big surprise today was Isabella, a beautiful gal with a broken moral compass who seems to have played the old trick of going into an apparel store’s changing room and coming out of it with something that was not hers. Everything seemed pretty straightforward to Jason until he noticed the girl was actually wearing a butt plug! Shocked, he conducted a cavity search to ensure she wasn’t hiding anything deep inside of her hole. Isabella pretended to be outraged, but she was enjoying every second of it, feeling Jason’s sturdy fingers climbing inside of her. Isabella was obviously guilty of something and Jason couldn’t just let her get away with a warning, so he offered her a deal: if she loves butt plugs so much, why not try real meat for a change?

Case No. 8003683 - The Butt Plug Situation

There was something special about Kiani from the start. She wasn't like the other girls who stole from this store. She had an air of curiosity and defiance. I knew she was a fucking freak from the jump, and I could tell we were going to have fun. Sure enough, when I bring her to the back office for interrogation. She has a stolen sex toy on her. She claimed she had never seen one before and wanted to see how it worked. I was happy to oblige this little slut's fantasy. If she's so curious about sex, why not show her how a man takes care of a girl's sexual needs? Of course, we started with the toy, but it wasn't long before I had that thirsty chick bouncing up and down on my cock. For a virgin, she sure knows how to ride dick...

Case No. 8003413 - The Curious Dildo Thief

A camgirl, Lily (Charlotte Sins), is performing in her living room when her stepbrother Robert (Tyler Cruise) unexpectedly walks in on her, having come home from college a day early. Robert is shocked that she's camming, saying that their parents take care of everything - including college tuition. But Lily says that's only true for HIM, so SHE needs to work. Robert is a bit sympathetic that she doesn't get the same care from their parents, but still says that camming is wrong and he's going to tell their parents unless she stops. Lily panics at the thought of losing her livelihood, and offers him sex so that he'll keep her secret.

PureTaboo - 2025.12.16 - Charlotte Sins - Camgirls Dilemma

A teen girl, Diane (Rissa May), packs her bags while her stepmom Maura (Reagan Foxx) argues loudly with her stepdad Frank (Charles Dera) and her stepbrother Scott (Axel Haze) in the next room. It's revealed that Maura and Diane moved in with Frank and his stepson Scott after Maura got divorced and remarried. What this led to, however, is a toxic environment where both men have been making sexual advances on Diane. At this point, she's had enough and decides to run away. She begs her stepmom to come with her, but Maura is too scared to leave and be out alone in the world again, so Diane leaves her behind.

A few months later, however, Diane returns in defeat, unable to survive on her own. She's let in by her stepmom, who dryly invites her inside, her eyes filled with resentment. Diane learns that Maura has had to endure Frank and Scott's behavior all by herself- especially considering that once Diane left, they turned all their frustrations onto her. Maura has grown to accept this, but still blames her stepdaughter for abandoning her in the first place.

Diane begs for forgiveness and asks to be accepted back into the family, something which Maura will consider only on one condition: Diane needs to submit herself sexually to her and the rest of the family's whims. Diane accepts, pulling down her shorts while Maura dons a large strapon. Maura fucks her stepdaughter in the ass, and when the two men arrive home, they hungrily join in as well. This leads to a filthy foursome where the men relish in having Diane come back to be their little sex slut, honoring the occasion with a family sex train.

PureTaboo - 2025.11.25 - Reagan Foxx & Rissa May - The Last Train Home

Many shoplifters think they can outsmart security guards with the oldest tricks in the book. Chanel, for instance, tried to sneak out some items from the mall by pretending to be pregnant and hiding stuff under her dress. Needless to say, Officer Vegas spotted her immediately and took him back to his office for questioning. The naive young girl insists that she is pregnant and has nothing to hide, but Jack easily manages to make her show what's beneath the dress. To assert his authority, the security guard pats Chanel down and gives her a cavity search to make sure there aren't any concealed items inside of her. With her will broken, Chanel is eager to do anything to walk away a free woman. Turned on by the girl's newly submissive attitude, Jack tells her that she can leave if she sits on his lap and plays with his meaty cock.

Shoplyfter - 2025.01.11 - Chanel Camryn - Not So Pregnant After All

Annie (Lulu Chu) has been raised under the rigid control of her religious stepmother, Mary (Penny Barber). Mary resents her ex-husband for being sinful - including watching pornography behind her back - and is determined to make sure Annie doesn't go down the same lustful path.But one night, Annie secretly watches adult content for the first time, and touches herself until she orgasms. She hopes Mary will never find out about it, but the next morning Annie is horrified to find a strange, living growth between her legs. She lets out a scream, causing Mary to come running, and Mary is horrified when she sees what's happened to Annie.Panicked, Mary rushes Annie to a nearby urgent care clinic, and begs for help from the doctor, Dr. Hunt (Sophia Locke). Doing her best to examine the grotesque mutation, Dr. Hunt quickly becomes both alarmed and fascinated. Dr. Hunt says that fluid is building up inside this strange growth, so they need to find a way to release the pressure before the situation gets worse... Blending body horror with psychological tension, The Growth explores the disturbing consequences of sexual repression, religious guilt, and the fear of desire.

PureTaboo - 2025.10.29 - Lulu Chu & Penny Barber & Sophia Locke - The Growth

Bailey (Aria Sloane), wants to have her own pet but her stepdad, Clive (Tommy Pistol), denies her because he feels she's not responsible enough. But if she agrees to BE a pet herself for a whole week, then he'll allow her to have a pet. Although Bailey finds this proposal weird, she's determined to get that pet, so she agrees. How bad could it be, right?

Things seem to start off well enough but as the week goes on, Clive starts to become purposely neglectful to make her feel what a pet would feel if she skimped on her duties. A missed meal here, a delayed outdoors break there... Still, Aria holds strong, knowing she's close to getting what she wants.

But eventually Clive becomes even more perverted to the point where he has her beg to get his 'bone' on the last day of the deal. Although she's shocked, Bailey, not wanting everything she's been through to be for nothing, gives in.

PureTaboo - 2025.10.21 - Aria Sloane - Family Pet

A 20-year-old exchange student, Anna (Lilly Bell), arrives at an idyllic suburban home for a two-week summer immersion program, only to become entangled in a web of dark family secrets.

Margaret (Penny Barber) is the stunning yet domineering matriarch who exerts total control over her household. Not even meek John (Max Fills) is safe as Margaret uses him, his rascally stepbrothers, Henry (Axel Haze) and Paul (Tyler Cruise), and his charming stepfather, Edward (Charles Dera), like pieces in her own twisted game.

You see, it's no coincidence that Anna's been sent to their household, with Margaret having secretly arranged for her arrival as a new plaything for the family. A little extra femininity to try and soften all the raging testosterone, so to speak. But as tensions within the household escalate, Anna is pulled into a nightmare she never could have imagined.

PureTaboo - 2025.09.23 - Penny Barber & Lilly Bell - The Secrets We Share

Madison (Madison Wilde) lives with her extremely strict stepdad, Thomas (Charles Dera). He runs a tight household, where Madison is expected to live up to his rigid expectations no matter what. That's why it's no surprise that he's nearly furious when Madison comes home late from school one day. Madison apologizes, but she knows that nothing she can say will dampen his disappointment. Luckily, he lets her off with a warning, and she goes up to her room to apparently study.

But when Madison is late again for dinner later, Thomas bolts upstairs to confront her, not bothering to knock on her bedroom door and simply bursting in. He is shocked to walk in on Madison practicing giving a blowjob to a dildo, and his anger comes to a rolling boil. This is NOT how he raised her, and even though Madison explains that she wants to practice sexual acts so that she can keep up with other girls her age, he's still furious with her despite her rationale.

Seeing as it will be nearly impossible to prevent Madison from experiencing the delights of adulthood, Thomas decides that he will take her sexual education in hand himself. He whips out his dick and instructs her to get on her knees and blow him. Madison's a little hesitant, but she wants to make her stepdad happy, so she does it. What follows is an intense and energetic sex session where Thomas shows Madison the ropes, including how to deepthroat his massive dick.

PureTaboo - 2025.07.15 - Madison Wilde - Step By Step Inch By Inch

A stepsister, Lyla (Lulu Chu), has been noticing her stepbrother, Mike (Axel Haze), acting suspiciously around their stepmom, Irene (Charlie Forde), so she keeps an eye on him. This leads to Lyla discovering that Mike has been secretly spying on their stepmom while she gets undressed. After seeing him do this on multiple occasions, Lyla finally confronts Mike about it.

Mike pleads with her not to tell their stepmom what he's been doing, offering whatever she wants to keep it a secret. That's when Lyla cheekily decides that she'd like to have sex with him. He agrees but is SHOCKED when Lyla starts showing him pictures of their stepmom from her social media page while they fuck! This turns Mike on even more and leads to energetic, wild sex as Lyla taunts and shames him for being a despicable little perv.

PureTaboo - 2025.09.02 - Lulu Chu - A Step Away From The Truth

Two stepbrothers, Cole (Parker Ambrose) and Ryan (Axel Haze), have a cruel prank in mind. Their target: a shy classmate of theirs named Lily (Lexi Lore). When they catch her walking home from school, they claim that they need help studying, inviting her to join them at their house the following day. Although Lily's a little unsure at first, the fact that this popular pair of stepbrothers want her help is enough to give in.The next day, Lily arrives to help the stepbrothers study but is surprised when they insist on loosening up first by playing with a harmless spirit board. Although she's hesitant, Lily gives in and they play the game. But she becomes flustered when the stepbrothers make the board say perverted things, like calling her out for being a virgin.But suddenly, it's no longer harmless fun as the bedroom door slams shut and the board goes flying. An ancient, disembodied demonic entity is summoned. It soon coaxes them all into a twisted game that reveals their darkest desires... and Lily's unexpected power.

PureTaboo - 2025.08.27 - Lexi Lore - Game Of Spirits

Maria (Cadence Lux) goes to her stepbrother, Leo (Robby Apples), for comfort after her new husband learns that she's not a virgin like she promised. On their wedding night, the husband received an anonymous text exposing Maria, which led to her being kicked out.

As she leans on Leo's shoulder, he slips up and it's revealed that HE sent the damning text to the husband, outing her. He claims he did this because he's in love with Maria and wants to be with her.

Maria is stunned and rejects Leo's love, demanding that he make things right by telling her husband that the message was just a sick joke. Leo eventually agrees to do so... IF he can fuck Maria. Although Maria is stunned, she's desperate to set things right with her husband, so she agrees...

PureTaboo - 2025.08.19 - Cadence Lux - Til Deception Do Us Part

In this sequel to Let Me In, Jessica (Reagan Foxx) knows that her old life with her family is completely ruined, so she has agreed to do whatever her demonic doppelganger Tess (Shay Sights) wants.

As Jessica drives down the road with Tess riding beside her, Tess says that Jessica needs to go through an initiation first. Jessica doesn't know what that means, but then they spot three men (Isiah Maxwell, Mighty Dee, and Slim Poke) who are stranded because their car ran out of gas. Seeing the perfect opportunity, Tess tells Jessica to 'help' them. Jessica catches on, so she pulls over and works with Tess to seduce the men and then complete the sinister initiation.

Once the initiation is complete, Jessica hungers for more, and Tess knows what their next step should be. They turn their sights on a family: Linda (Lexi Luna), her wife Teri (Sophia Locke), and their stepson Craig (Tyler Cruise), corrupting them as the next part of Tess's plan to build an army of lookalikes...

PureTaboo - 2025.07.01 - Reagan Foxx & Lexi Luna & Shay Sights & Sophia Locke - Let Me In Too

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