Long Hair (191)

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

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

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

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

Cole Church and Jay Romero are studying for a test when suddenly the subject of their stepmoms comes up in conversation. Both believe the other’s stepmom wants to fuck them, so they make a bet who can make it happen first. Like the good stepmoms they are, Katie Monroe and Nova Sky make sure they both win their bet and fuck Cole and Jay at the same time.

MomSwap.2021-10-11.Jupiter Jetson, Katie Monroe

Rion and Robby are both great students. Only one problem, they are just so embarrassed by their stepmom’s behavior. Once these two biker moms find out how their stepsons really feel about them, they decide to show them who's in charge. Lilly and Tricia swap their scholarly stepsons and show these virgins boys who make the rules and calls the shots.

MomSwap.2021-07-05.Lily Lane, Tricia Oaks

When mom friends Casca Akashova and Jane Dove get back from a girls day out they find their sons just slacking on the couch, they know it’s been tough for them to take care of themselves during the pandemic so they decide to help them by giving them a makeover. When the boys come downstairs looking all cleaned up and handsome they start talking about how they’re gonna get all the girls now. Casca and Jane are feeling kind of jealous though, so they decide to swap sons and have them all to themselves instead!

MomSwap.2021-07-19.Casca Akashova, Janie Erixa

Best friends Carmela Clutch and Carmen Valentina are planning to go on a trip together with their respective sons Johnny The Kid and Nade Nasty, the problem is that the boys don’t get along. Carmela and Carmen decide to discipline them by showing them a lesson in sharing so they swap their sons and teach them exactly how to get along.

MomSwap.2021-04-26.Carmela Clutch, Carmen Valentina

MILFs April Storm and Nickey Huntsman are lamenting their husbands' lack of care and intimacy, especially with Mother's Day coming up. Little do they know, their stepsons are listening in...and they are hatching a plan to make sure April and Nickey feel appreciated.

MomSwap.2021-05-10.April Storm, Nickey Huntsman

Karen Fisher and her stepson Robby Echo visit her good friend Syren De Mer and her stepson Nathan Bronson one afternoon. While the boys play in their room, Syren shares with Karen that the divorce has been rough, leaving her feeling lonely most nights and unfortunately, Nathan doesn’t let her take care of him like she used to. When the boys come back down needing some attention, Karen and Syren have the idea to swap their stepsons and show them what a real good time they can have with mommy’s friend!

MomSwap.2021-03-29.Karen Fisher, Syren De Mer

I fucking love my job. Being a security guard at the mall is such a power rush, especially when bratty little thieves like Ameena try to steal from us. I know girls like her, getting caught is half the fun for these sluts, and I'm more than willing to play my part. Now I get to have fun with her tight little holes and paint that pretty face with a fresh load of cum... what a life!

Shoplyfter - 2025.09.13 - Ameena Green - The Politicians Daughter

Redhead Lacy Lennon is looking extra hot in her shiny stilettos, but the alluring outfit has her stepdad suspicious of her motives! Turns out, she is not trying to get out of babysitting at all. In fact, she wants to stay in all day and night with her loving stepdad. The blue eyed babe wants to remind her old man what it is like to be young and fun, so she takes off her tight leotard and makes seductive eyes at him. Then, she gobbles his love stick, soaking it in her spit while she gives him a nasty blowjob. Finally, she bends over and pops her young pussy, letting him slide his veiny dick deep inside while she screams, yes yes yes!

Lacy Lennon - [TeamSkeetXSpankMonster.com] - [2019] - Shiny Stilleto Fuck Sesh

Prev Page 7 of 8 Next