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Missionary (276)

Alex, a pampered cheerleader with a snobby attitude, feels the sudden rush of pre-game panic and tries to steal the one lip gloss that perfectly complements her pout. Her hasty attempt at shoplifting did not go unnoticed as Ryan, a security guard who has no tolerance for bratty girls, observes the whole incident and intercepts the petty thief before she tries to escape. Now inside a cramped office, Alex tries to lie to the security guard to make it to the match on time. Ryan is not eager to let her go so easily, and conducts a thorough cavity search, only to find the missing lip gloss hidden deep inside her pussy. Desperation gets hold of Alex as she imagines the repercussions of her actions on her popularity. Lucky for her, Ryan has a soft spot for hot cheerleaders with pouty lips who know their way around cock. Faced with no alternative, Alex gives Ryan a sloppy blowjob and lets him stuff her up to avoid her reputation as a cheerleader being ruined by an “honest” mistake.

Case No. 8003863 - The Sloppy Cheerleader

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

Freya’s always been a brat, and her stepmom Ivy Mae barely does anything to stop her. This time, however, neither of them is in charge. After Freya gets caught shoplifting at the mall, Mr. Fitzwell, the security guard, calls upon her stepmom and quickly realizes what kind of dynamic he’s dealing with. It becomes clear to him that he needs to be assertive and dominant if he wants justice to be served. These two are used to getting away with anything, but today, the only thing they can do is use their little holes to milk his cock until he explodes all over their pretty faces.

Bratty Teen Freya Von Doom Gets Caught And Fucked With Her Stepmom (Member Story)

On Mother's Day, everyone is desperate to find the perfect gift, and they do anything to get it. As a security guard, I see people stealing all kinds of gifts on this day every year. That's why I knew this chick was hiding something. I took her to my office and tried to check her purse and body, but she insisted on her stepmom being there. Once both of them were in the room, I did my job and found a very expensive bottle of perfume in her bag that she stole for her stepmom. I tried to find out if that was the only thing she stole, so I checked her body, stripping her naked and touching every inch of it, even shoving my fingers inside her ass and her pussy. Neither of them wanted problems, so I offered them a choice: they could both suck my cock, or go to jail. They didn't even hesitate. Before I knew it, both of their mouths were around my dick, sucking it dry and licking it as if their lives depended on it. I guess moms are not the only ones getting something nice this time of the year.

Case No. 8003860 - Stepmom To The Rescue

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

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

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

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 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, Ruby (Emma Rosie), is standing outside of her house naked while holding a humiliating sign. A stranger, Marlow (Derek Kage), is so stunned by the sight that he stops his car and gets out to ask Ruby what happened. Ruby explains that her parents are angry at her because she lost her virginity, so they decided to punish her like this.

Marlow says that's outrageous, and declares that he's going to give her parents a piece of his mind right now. But Ruby says that her parents went out and locked the door, so she has no way of getting back into the house until her parents come back and decide to let her in. She adds that all of her neighbors are the 'mind your own business' type, so she knows that none of them will bother to help her.

Seeing that Ruby is shivering, Marlow offers to drive her back to his place so she can warm up, and then he can return her before her parents notice. She agrees, but once she's at his place it turns out his intentions aren't so noble...

PureTaboo - 2025.12.02 - Emma Rosie - Nude And Unusual Punishment

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

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

Janet (Lexi Luna) is catching up with her longtime friend, Phil (Leo Vice). Their friendly conversation takes a turn, however, when Phil mentions that he's found out that Janet has become a sex worker. He holds no judgment against her for it, which momentarily reassures her, but things get weird when Phil starts musing about potentially booking her services for himself. At first, Janet thinks he's joking, but when it turns out that he's serious about it, she is totally disgusted. She eventually agrees to give her so-called 'friend' a taste of her goods, but warns him that it won't cost him anything... except their friendship. Phil takes her up on it, so Janet has intense, energetic sex with him while putting on the same fake 'enthusiastic' face she's put on for her other clients, ultimately ending their friendship with a resounding bang.

PureTaboo - 2025.10.07 - Lexi Luna - Parting Shot

A teen girl has had a private discussion with a high school guidance counselor, Judith (Princess Emily). Unfortunately, the teen's two overbearing parents, Dan (Chad Alva) and Maria (August Skye) confront Judith in her office, demanding to know all the details of that private discussion.

Judith refuses to give out the confidential information, but her confidence crumbles when the ruthless parents recognize her as someone they went to school with - an unpopular girl who was bullied. The parents switch tactics, bullying her and rubbing her loneliness in her face, ultimately offering her sex in exchange for the information they want.

Overwhelmed by both the taunting and the temptation, Judith finally gives in...

PureTaboo - 2025.08.05 - August Skye & Princess Emily - Misguiding The Counselor

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

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