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Family Roleplay (71)

Fine, it's true. I stole a pair of heels, but I just wanted to look good for my concert, and they were so expensive. I didn't think I might go to jail for something like that. The security guard even made me undress for him so he could do a cavity search. Did he really have to touch every inch of my body? He even ripped my tights and shoved his fingers inside my pussy! When he made me bend over and I felt his hand inside me, I had to prevent myself from moaning. I knew what he was doing was wrong, but it felt so good. Then, he grabbed my tits, got my nipples hard, and asked me to do something for him. If I did what he wanted, he was going to let me go, and I would even be able to keep the heels. He didn't have to tell me what he wanted. When he made me get on my knees and dropped his pants, I knew exactly what that was. His cock tasted like power and freedom, and every drop of cum was making me hornier. Why was my pussy so wet for a security guard? Then, he fucked me so hard I couldn't even pretend I didn't like it. Can you blame me? His dick was hard and fat, riding it gave me an orgasm, and I was going to leave his office with his cum inside me and brand new heels. 33:53
Case No. 8004262 - Keep The Heels, But Wipe His Cum Off Them
We knew as soon as we saw her what kind of girl Scarlet was. Troublemaker, little fucking horny slut, willing to do anything to have her clit played with. See, Officer Avalon and I have been doing this a long time. We know a fucking punk when we see one. Well, we brought this girl to the back, and I've got to say - we both wanted her. Petite, small titties, a cute little bubble butt, and my favorite - a ginger. Avalon and I knew she was guilty from the jump, but we were going to have our fun. Stripped naked, we enjoyed taking our time ripping her clothes away piece by piece. The fun really begins when you have them bent over the desk, legs spread, and pussy starting to get wet because you know they like it, despite their efforts to suggest otherwise. Scarlet was no different. As soon as Avalon and I started playing with her pink pussy, she was dripping wet. 38:13
Case No. 8004034 - Threesome With The Vibrator Thief
All I wanted was to fit in. I didn’t think that stealing a pair of sneakers would end with a security guard fucking my brains out. When he asked me to take off my clothes, I thought he was only going to make sure I didn’t steal anything else, but he took his sweet time touching every inch of my naked body. He stopped at my tits and squeezed them really hard, as if I could have hidden anything there. Then, he made me bend over his desk, and I felt his fingers slowly sliding into my pussy, deeper and deeper. Should I have stopped him? Maybe, but I wanted to get out of trouble, and he knew how to use his hands. Besides, it was my last year of college, and law school was on the line, so if the prize of those sneakers was having a cock in my mouth for a while, I was going to suck it until I had swallowed every drop of cum. His dick felt even better than his fingers when he shoved it inside me, and I rode it so well that he let me keep the shoes. 32:36
Case No. 8004401 - Her Pussy For A Pair Of Shoes (Winter Flynn's Debut)
With the excuse of shopping for a friend’s wedding, Nikki and Satine, two pals with a knack for getting in trouble, are accused of shoplifting. Dragged by security guard Jack Vegas, the girls are questioned about the missing goods, as the officer has evidence of them hiding jewelry under their Indian sari dresses. Cornered and nervous, Nikki and Satine try to deny the whole thing, but Jack is onto them, and he has zero tolerance for little lying brats. Convinced of their crimes, Officer Vegas checks the girls’ cavities to both look for stolen goods and teach them a lesson about stealing. Now completely broken and under the threat of going to jail, Nikki and Satine decide to cooperate with Jack to avoid facing the consequences. The handsy officer fondles the two felons and feeds them with dick with the promise of keeping the whole incident secret. 47:53
Case No. 8003887 - Under The Saris
Food bloggers make me nuts. They think they can eat anywhere they want and not pay their bill just because they have a few followers. Then, when I catch one of them, like this pretty girl today, they always try to get away by asking to deal with a female security guard instead. Guess what? My coworker is as tough as I am. I'll wait and watch as she undresses our suspect and touches every inch of her body, trying to find more evidence. We always get our way, and if she doesn't want the cops to come, she'll make us cum. Sharing a body with my hot coworker is my favorite thing about my job. I love seeing their tits rub against each other, having two pussies to fuck, and watching their mouths share my dick. Our solution might be unorthodox, but it's way better than going to jail, so she better let us fuck her hard. Eating pussy and dick is the only way she'll pay for her meal. 37:32
Case No. 8004037 - Eating Pussy And Dick Paid For Her Meal
Bambi ran away from home because she thought she could easily provide for herself, but she soon discovered just how hard it is in the real world. She got caught stealing food at the mall, and after attacking some employees, she was tied up in the security room. Luckily, Mr. Fitzwell is a very reasonable man, and he’s agreed to let her go if she cooperates with the cavity search. What she didn’t realize is that Mr. Fitzwell searches better with his cock than his hands… 38:23
Case No. 8004404: Pounding The Runaway Teen
It didn't matter that I was wearing a thin shirt and a tiny skirt that showed I had nothing on me. When the security guard found out I was using my ex's credit card to go on a shopping spree, he didn't hesitate to undress me and put his hands all over my naked body, searching for more evidence. He claimed he was only trying to do his job, but tearing my thighs and leaving my bare ass exposed was beyond inappropriate. He even used his fingers to search inside my pussy. I wanted to expose him, but all that power and the way he used his hands were turning me on. I wondered if he could tell I was getting wet. I had to get out of there before I did something that I could regret. As if he heard my thoughts, he gave me a way out. All I had to do was suck his cock. When he dropped his pants, I didn't have to question if I'd do it or not. His dick was big and hard, and I was too horny to resist temptation. If we fucked, we'd both win. 38:19
Case No. 800425 - His Ex's Credit Card Got Her A Big Dick
I’m so tired of these lowlife criminals… they think they can steal from under my nose? I have a pristine record, and I’m not about to lose my credibility over two fucking sluts who decided to spend a day at the mall and fuck with the security guard. No, today they’re about to find out what happens when you try to fuck with me… you get fucked. 43:58
Case No. 8004031 - Bratty Teens Fuck Around And Find Out
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. 28:57
Case No. 8003863 - The Sloppy Cheerleader
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. 37:29
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... 44:54
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. 35:07
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. 36:35
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? 43:57
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... 43:29
Case No. 8003494 - Skater Babe Pays Her Dues
Emma and River might look cute in their matching work outfits, giving a sort of big sis/young sis vibe, but these two BFFs are juvenile delinquents trying to get away with shoplifting. Their plan was simple and diabolical: they both got jobs at one of the mall's luxury brand stores and tried to sneak out a couple of fancy purses before ending their shift. However, Officer Mike has a keen eye for spotting perpetrators, so he caught the girls red-handed and took them to his office. River and Emma try to lie their way out of the situation, but they are awful at it, pushing Mike to conduct a thorough search. Now, the girls have a choice: they can both lose their jobs and face criminal charges...or they can take one of Mike's kinky offers and give his cock a reason to let them go with a warning this time. 39:30
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. 36:17
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. 36:22
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? 41:23
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... 38:33
Case No. 8003413 - The Curious Dildo Thief
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. 35:25
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. 54:43
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. 54:06
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. 153:28
PureTaboo - 2025.09.23 - Penny Barber & Lilly Bell - The Secrets We Share
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