Side Fuck (101)

So, she thinks being a security guard is pathetic? She's going to regret saying that. She can't expect me to ignore the fact that she's wearing all those stolen bikinis under her clothes, and she can't expect me to go easy on her after she insulted me. I'm going to show her just how non-pathetic my job is by searching her entire naked body for more evidence. I'm going to grab her tits, her ass, and I'm going to shove my hand up her asshole. If that deep cavity search doesn’t prove how much power I have over her, I’ll give her a choice to show her what I can do. She can go to jail, or she can suck my dick. Let's see how tough she is when I fuck her on my chair. She better be great at riding my cock if she wants me to forget everything she did and said.

Case No. 8003815 - The Busty Bikini Thief

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

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

Being a security guard is tough because thieves always think they can get away with anything. This time, a gorgeous woman stole ballet accessories and believed I wouldn’t notice because she was wearing them as though they were hers. Sure, that tight ballet leotard fit her like a glove, and I loved that I could see her perky ass through her tights, but the law is the law. Then, she tried to use her friends as an example to avoid trouble, claiming they always steal from the store and the other guards let them walk away. Well, her friends must be sluts because the only way to avoid trouble is by cutting a deal with the guards. Luckily for her, the way her body looked with the stolen merchandise got my dick hard enough to give her a choice: she could give me a blowjob or go to jail. It was no surprise my dick was inside her mouth right away, but as she was sucking my cock dry, I realized I had to make her do way more than that.

Case No. 8003417 - The Slutty Ballet Dancer

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

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

Abigail (Leana Lovings) is a teen high school student from a poor family. One day she goes to her guidance counselor's house, since the guidance counselor, Mr. Taylor (Jason Sarcinelli), has offered to give her some of his own girl's old dresses for Abigail's upcoming prom.

Abigail is grateful, but as she changes in and out of the dresses, Mr. Taylor spies on her through a crack in the doorway. But when Abigail discovers that Mr. Taylor is both spying on her AND is lying about being a parent, it's revealed that he manipulated the situation in order to seduce Abigail.

Abigail is at first livid, but Mr. Taylor manipulates her further, guilting her by reminding her of all the help he's given her. After everything he's done for her, the least she can do is show her gratitude... right?

His Charitable Act

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 lesbian teen, Anna (Sophia Sterling), invites her bisexual crush Bailey (Maisey Monroe) over for a movie night to get to know her better. Anna's stepdad Jake (Ryan Driller) is supportive and plays wingman in an attempt to help Anna, but it backfires when Bailey starts coming onto HIM instead. Bailey cheekily invites him to watch the movie with them, which leads to Bailey tempting Jake to fool around with her under a shared blanket. All the while, Anna is unaware. When Anna finally leaves the room for a short time, Bailey and Jake have lustful sex with a major almost-caught moment.

PureTaboo - 2025.12.09 - Maisey Monroe - Stealing Her Crush

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

Lucas (Isiah Maxwell) is outraged when he finds that someone egged his house. Thanks to his doorbell camera, he finds out that the culprit is his teen neighbor, Jodie (Summer Col). He confronts Jodie, saying that he already cleaned up the mess outside, so she needs to make it up to him by cleaning INSIDE his home... Otherwise, he'll tell her parents.

Jodie agrees, but as she cleans, Lucas gets increasingly tempted by the sight of her body. He 'accidentally' spills water on her so she'll have to clean dressed only in her underwear, and eventually he offers that she won't have to keep cleaning IF she has sex with him. Jodie is shocked but wants to stay out of trouble, and does her best to please him with an energetic sex session.

PureTaboo - 2025.10.28 - Summer Col - Cleaning Up Her Act

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

Steve (Elias Cash), his girlfriend Cassie (Leana Lovings), and their mutual friend Danny (Victor Ray) are playing poker. When Cassie takes a break and goes into the kitchen to make snacks, Danny suggests a wild bet: whoever loses the next hand gets to fuck the other guy's girlfriend. Steve playfully accepts, not thinking the bet is serious. But when he loses, he finds out that Danny was completely serious about it.

When Cassie finds out about the stakes of the bet, she seems furious and decides to go along with it to make Steve feel bad for using her in a bet. Steve eventually leaves, dejected and humiliated, but once he's gone... the truth reveals itself.

PureTaboo - 2025.11.11 - Leana Lovings - Up The Stakes

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

After his parent's sudden passing, Rick (Isiah Maxwell) is left to pick up the pieces, including making all the arrangements for the funeral. To make matters even worse, it was discovered in his parent's will that he had a younger mistress to whom the deceased even left some of his inheritance. Rick is eager to help his family move past this, but he ends up getting a surprise visit from the mistress in question, Chrissy (Aria Sloane). Despite his anger, Rick humors her and allows her inside, after which he learns that Chrissy wants to attend the funeral despite the entire family forbidding it. She pleads with Rick, eventually offering him to have his way with her body in exchange for her being able to attend. Rick is disgusted, but takes her up on her offer, leading to a rough sex session that he never expected to have.

PureTaboo - 2025.07.29 - Aria Sloane - Nothing She Wont Stoop To

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

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

Loreli (Coco Lovelock) is getting ready to don her alter ego, Jasmine, for one of her regular camming sessions. She puts on her wig, outfit, and makeup... transforming before our very eyes. It figures that she'd have to put on a disguise, since her parent (Aaliyah Love) would lose it if she found out what Loreli did to pay her way through college.

When Loreli starts her camming session, however, she gets an invite for a private video call with one of her chatters, 'Keith'. But when Keith turns on his camera, Loreli is disturbed to see him wearing clown makeup. He looks terrifying, and he's also clearly desperate for affection and intimacy. The surreal combination is too much for Loreli to handle, so she ends the call.

Later, Loreli goes to visit her stepfather Wes (Dick Chibbles) to keep him company. When he greets her, however, she notices the remnants of clown makeup on his face. Loreli confronts him, causing him to reveal that he's been seeing a camgirl named Jasmine behind his wife's back. Loreli relishes the fact that he has no idea that she's the camgirl he's been so horny for, and she then decides to give this pathetic man what he wants... his stepdaughter's tight, wet pussy.

PureTaboo - 2025.06.10 - Coco Lovelock - Fathers Day

Lizzie (Rebel Lynn) has been receiving love letters for months from her deployed soldier husband, promising his imminent return. But that's not all: the letters also share a fantasy of Lizzie blindfolding herself to welcome him home with a sexual encounter unlike any they had before he left.

When the day comes, Lizzie dons the blindfold and has intimate sex with the man she THINKS is her husband, only to discover partway through the sex that she's actually with her husband's sibling, Sam (Rion King). Lizzie is shocked at the realization that she's having sex with her in-law... and she is shocked even further when she learns the truth about her husband.

PureTaboo - 2025.06.03 - Rebel Lynn - To The Letter

Prev Page 3 of 5 Next