Older / Younger (109)

Sophia notices her stepson Nade has been having serious issues at public school. When talking with her friend Cory, she tells her she home-schools her stepson Nick for the same reason and offers to help Sophia out by letting Nade take a couple of fundamental courses with her.
A few months later, Nade seems to be doing better and showing significant growth in all his core subjects. One day, Sophia decides to drop in unannounced and is shocked to find both Nade and Nick taking turns to eat Cory’s pussy. The teacher explains to her that this is a sex education course, another key subject the boys need to learn about. After the initial shock, Sophia accepts that Cory’s teaching methods do give results, so she decides to volunteer herself to help Nick and Nade learn more about sex ed.

HomeSchool Sex Ed

When Athena is at her wit’s end with her stepson Tyler’s bad attitude, she calls her therapist Jenna asking for guidance. Jenna relates with Athena, having gone through the same issues with her stepson Franco during her divorce. Once they’re all sitting down together, Jenna teaches Athena that the best way to make them help out is by encouraging them with sex!

Lessons on Motivation

When Kenzie and Pristine learn their stepsons, Oliver and Elias, plan to enlist in the military, the busty babes do everything they can to stop the boys from going. Oliver and Elias get an intense boot camp experience, but when the intensive training isn’t enough to deter the boy’s dreams, Kenzie and Pristine rely on extreme measures.

Nicky has a problem at school with Alex, who bullies Nicky constantly. Nicky’s stepmom Charley puts her foot down and confronts Alex and his stepmom, Crystal. Getting right down to the matter at hand Charley disciplines Alex the only way she knows how — with her thick thighs. Things get spicy fast, and before anyone knows it, they’re having a full-on stepmom swap.

Charley's Discipline Plan

When Joshua and Oliver find out about the kissing scene in their upcoming school play, they are eager to get the part. In need of some help with practicing their lines, they recruit their sexy stepmoms to read for the female leads. Appalled by Joshua and Oliver’s lack of confidence, the stepmoms come up with an idea to help the boys land a part in the play.

Naked and Unafraid

Robby Echo is skeptical of the new neighbors, who seem to carry a dark aura around them. His stepmom, Carmen Valentina, assures him that Aria Khaide and Oliver Davis are nothing more than friendly, so she takes Robby to meet them. But upon their arrival, Aria and Oliver seem to have a strange affection for one another, and despite her efforts to ignore them, Carmen can’t help but feel aroused. Aria hatches a scheme to help Robby lighten up, and with the help of Oliver and Carmen, the plan is soon underway.

Madi and her best friend Britt beg their respective stepbrothers Austin and Oliver to play spin the bottle with them so that Britt can have her first kiss. Oliver protests at first but eventually they give in and the four sit on the floor, spinning that bottle. They all take turns making out with each other, until things get way naughtier and the guys swap their stepsisters to fuck them!

Spin the Bottle

Penelope and Aubree enjoy their sleepover before being interrupted by their stepbros, David and Oliver. The guys decide they need to scare their stepsisters a little with a spooky story about a virgin snatcher. The plan goes all too well, and soon enough, everyone is fucking everyone!

Swappin' Scary Stories

Best friends Alona Bloom and Percy Sires are tired of their boring school uniforms so they decide to ask their brothers for some money to get some cute outfits. David Lee and Jason Deep immediately blow their sisters off, but they confess to each other that the other one’s sister has been looking cute lately, and they end up making a deal. David and Jason tell Alona and Percy that they will give them the money they asked for, but only if they agree to do a sister swap!

Sis Swap for Haul

Case No. 8004262 - Keep The Heels, But Wipe His Cum Off Them

Quirky Sophia and her bumbling stepbrother Rion, a duo of amateur scam artists, are up to their usual shenanigans. This time, they are posing as plumbers to get close to the cash register of this big department store. Yet, their grand plan is easily derailed by the unexpected appearance of Will Pounder, the store's no-nonsense, but surprisingly kinky, veteran security guard. Instead of immediate arrest, Will, a man who's seen it all, takes the stepsiblings to his faintly back office. After a tension-filled interrogation, Will undresses Sophia for a thorough cavity search in front of her dim-witted stepbrother. The poor guy tries to stop the process, but Will asserts his authority and conducts his security search anyway. The evidence is stacked against the incompetent stepsiblings, and the chances of them going to jail are high, but Officer Pounder knows how to make these charges disappear. After having inspected Sophia's "pipes" thoroughly, Will recruits the help of Rion to do some "unorthodox" plumbing on Sophia. The oblivious blonde accepts her fate and lets both Will and her stepbrother use their meaty tools on her pipes at the same time as a way to keep the whole incident under wraps.

Case No. 8004039 - Laying Both Pipes

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.

Case No. 8003887 - Under The Saris

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.

Case No. 800425 - His Ex's Credit Card Got Her A Big Dick

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

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

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

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

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

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

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

It’s Mother’s Day again, the time of year when we celebrate MILFs worldwide. Olivia and Sophia are as hot as they come, so their stepsons, Billy and Chris, want to make sure this is the best Mother’s Day ever! Things get a little spicy when Billy and Chris present their moms with an unexpected “gift.”

MomSwap.2022-05-09.Olivia Jayy, Sophia Locke

Jenna Noelle and Cole Church join Sheena Ryder and Jay Romero for dinner at Sheena’s house. But things take an unexpected turn when Sheena reveals that she lets her stepson, Jay, fuck her on the regular. Blown away by this, Jenna doesn’t know what to say but is captivated by the thought as well. Shortly afterward, what was supposed to be a lovely dinner escalates into group sex on the couch, with everyone focusing on Jenna. She is entirely turned on by this taboo encounter with her stepson and his friend and lost for words simultaneously.

MomSwap.2021-11-08.Jenna Noelle, Sheena Ryder

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

Prev Page 4 of 5 Next