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Family Roleplay (71)

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. 46:21
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. 39:28
PureTaboo - 2025.09.02 - Lulu Chu - A Step Away From The Truth
Two stepbrothers, Cole (Parker Ambrose) and Ryan (Axel Haze), have a cruel prank in mind. Their target: a shy classmate of theirs named Lily (Lexi Lore). When they catch her walking home from school, they claim that they need help studying, inviting her to join them at their house the following day. Although Lily's a little unsure at first, the fact that this popular pair of stepbrothers want her help is enough to give in.The next day, Lily arrives to help the stepbrothers study but is surprised when they insist on loosening up first by playing with a harmless spirit board. Although she's hesitant, Lily gives in and they play the game. But she becomes flustered when the stepbrothers make the board say perverted things, like calling her out for being a virgin.But suddenly, it's no longer harmless fun as the bedroom door slams shut and the board goes flying. An ancient, disembodied demonic entity is summoned. It soon coaxes them all into a twisted game that reveals their darkest desires... and Lily's unexpected power. 50:06
PureTaboo - 2025.08.27 - Lexi Lore - Game Of Spirits
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... 47:08
PureTaboo - 2025.08.19 - Cadence Lux - Til Deception Do Us Part
In this sequel to Let Me In, Jessica (Reagan Foxx) knows that her old life with her family is completely ruined, so she has agreed to do whatever her demonic doppelganger Tess (Shay Sights) wants. As Jessica drives down the road with Tess riding beside her, Tess says that Jessica needs to go through an initiation first. Jessica doesn't know what that means, but then they spot three men (Isiah Maxwell, Mighty Dee, and Slim Poke) who are stranded because their car ran out of gas. Seeing the perfect opportunity, Tess tells Jessica to 'help' them. Jessica catches on, so she pulls over and works with Tess to seduce the men and then complete the sinister initiation. Once the initiation is complete, Jessica hungers for more, and Tess knows what their next step should be. They turn their sights on a family: Linda (Lexi Luna), her wife Teri (Sophia Locke), and their stepson Craig (Tyler Cruise), corrupting them as the next part of Tess's plan to build an army of lookalikes... 59:44
PureTaboo - 2025.07.01 - Reagan Foxx & Lexi Luna & Shay Sights & Sophia Locke - Let Me In Too
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. 46:45
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. 50:22
PureTaboo - 2025.06.03 - Rebel Lynn - To The Letter
A family of four arrive back at their vacation rental, having spent the day at an amusement park. The stepparents, Laura (Melissa Stratton) and Eric (Seth Gamble), leave to get dinner ready, leaving Jordan (Selena Love) and Oliver (Max Fills), their stepdaughter and stepson (who are also stepsiblings to each other), alone. Jordan and Oliver are grateful for the amazing vacation but also suspicious, wondering if their stepparents may be buttering them up for something. Sure enough, after the family finishes eating dinner, the stepparents continue seemingly buttering Jordan and Oliver up, which leads to Jordan and Oliver asking them what's going on. The stepparents become a little nervous, but admit to taking Jordan and Oliver on this vacation to tell them a secret: the stepparents THEMSELVES are stepsiblings! Laura and Eric explain that after they both turned 18, they had a torrid affair with each other, even though they were stepsiblings. Their family found out and they were both kicked out. Ashamed, Laura and Eric separately tried to pursue 'normal' romantic relationships, which led to Laura becoming a stepmom to Jordan and Eric becoming a stepdad to Oliver. However, Laura and Eric still loved each other and eventually divorced their spouses and returned to each other, but kept their history a secret. Jordan and Oliver are shocked and disgusted by the revelation. However, the stepparents insist that their love is pure... and they also reveal that they want all four of them to fuck as a family. 45:06
PureTaboo - 2025.05.27 - Selena Love & Melissa Stratton - Old Enough For The Truth
Lana (Hazel Moore) is celebrating her 19th birthday, so she has invited over her friends Christie (Hailey Rose) and Chloe (Liz Jordan) for a slumber party. Lana's stepfather Greg (Seth Gamble) promises to watch over the three girls and keep them out of trouble, especially since Lana's other parent (Lexi Luna) will have to miss the party due to a last minute shift change at work. However, Greg's intentions towards two of the girls are less than pure, and he knows that his stepson Ethan (Nick Strokes) has strong desires for the third girl. As Greg hatches his scheme with help from Ethan, the birthday girl learns disturbing truths about the people she thought she knew... and by the time the party's over, nothing will ever be the same again. 52:44
PureTaboo - 2025.04.29 - Hazel Moore & Liz Jordan & Hailey Rose - The Partys Over
A teen, Shawna (Kimmy Kimm), wants to move out and live on her own in another town, but her parent, Jesse (Sheena Ryder), insists she's still too young for that. Eventually, Jesse offers a compromise: Shawna can move out IF she stays with her Uncle Nick (Kyle Mason), who is Jesse's stepbrother. Shawna protests that the reason WHY she wants to move out is so she can have complete freedom, not live with her uncle! But Jesse insists that her choices are either stay with her uncle or stay home. Eventually Shawna begrudgingly agrees to go stay with her uncle. However, when Shawna arrives on her Uncle Nick's doorstep, they start enthusiastically making out, revealing this was their plan all along. And without Jesse to watch her anymore, Shawna is going to have sex with her uncle as much as she wants... 39:46
PureTaboo - 2025.03.25 - Kimmy Kimm - Playing Right Into Their Hands
Tina (Kimmy Kimm) has recently discovered she's a lesbian, but has to keep it a secret from her intolerant family, who would all but disown her if they found out. Luckily for her, college is on the horizon, so she'll soon be free to be herself without having to hide from those around her. One day, however, her stepcousin Marco (Juan Loco) comes over to visit and corners her in her room, asking to play Truth or Dare with her. She accepts, but is mortified when the game leads to Marco discovering her secret. Marco knows what her family will do if they find out, so he convinces Tina to keep playing the game or he'll reveal her secret to everyone. With no other option, Tina agrees to keep the game going, with the dares getting more and more sexual... until the final dare leads to them having full sex with each other. 43:57
PureTaboo - 2025.08.12 - Kimmy Kimm - No Truths Only Dares
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! 38:14
Shoplyfter - 2025.09.13 - Ameena Green - The Politicians Daughter
Rachel (Kenna James) is happily married to Tye (Chad Alva). However, Rachel wonders why Tye has kept her away from his stepmom Amy (Penny Barber) and his other parent Josh (Charles Dera). Rachel has never met or spoken to them after years of dating Tye, and he even refused to invite them to their wedding. One day, Rachel receives a phone call from Amy saying that she and Josh happen to be coming to town, so Rachel decides to be polite and invite them to stay here instead of going to a hotel. When Tye finds out, he gets upset at the idea of his parents staying over. Rachel is confused and asks why - his parents sound nice! Tye doesn't want to explain, but begrudgingly says that Rachel doesn't have to cancel the invitation to his parents, so Rachel drops the subject. When Amy and Josh arrive, Josh surprises Rachel by suddenly giving her a tight hug, lifting her off her feet. After he puts Rachel down, Amy hugs Rachel too, and sniffs her hair. Rachel starts to get weirded out, and when Tye arrives home from work, things get even more awkward and uncomfortable, especially when Amy gives Tye a goodnight kiss on the lips. This family visit might be a lot more than Rachel bargained for... 53:43
PureTaboo - 2025.02.11 - Kenna James & Penny Barber - Not Again
Mike is absolutely convinced that Ms. Olsen is out to get him. Low grades, detentions, and all kinds of punishments are making this jock’s senior year a living hell—and he’s determined to get back at her, no matter the cost. One day, he catches Ms. Olsen engaging in inappropriate behavior on school grounds, and he secretly records the whole thing on his phone. Later, he confronts her in her office and tells her what he saw. Anya tries to brush him off with threats, but Mike shows her the footage. Now, her job is on the line—and it’s up to Mike whether she stays or goes. The horny student starts fondling her, giving him a clear idea of what he has in mind. Ms. Olsen plays along, striking a horny deal with her student, sealed with hot cum, to keep the whole incident under wraps. 35:48
pervprincipal.25.08.09.anya.olsen
Anya Olsen is trying to be a good stepmom for Juan Loco, but he just sees that she's nagging him relentlessly. She wants Juan to wear pajama bottoms in bed, and then she takes his phone away. Since Anya wants Juan to get the best night's sleep possible, she strips down to her thong and climbs into bed with him. After asking Juan if he finds it relaxing, Anya strokes his hair and helps him go to sleep. The next morning, Anya comes in to tell Juan to change his underwear. She has to watch to make sure he does it. Later, when Juan has finished showering, Anya is there to hand him his towel and make sure he's cleaned everything thoroughly. She tells Juan the only way she'll know if he washed his dick properly is to sample it. One thing leads to another and next thing Juan knows he's got Anya on the sink so he can eat her out. Getting to his feet, he listens to stepmom and shoves it into her twat. Taking their action to the bedroom, Juan lays spreadeagle as Anya mounts him to ride in cowgirl. Reverse cowgirl follows suit, and then Juan gets to bang Anya as she kneels before him. On her side, Anna lifts one leg as Juan spoons behind her and keeps her pussy party going until he pops deep in her fuck hole. 41:20
momwantscreampie.25.10.11.anya.olsen.your.turn.to.take.care.of.me.stepson.4k
Anya Olsen is trying to be a good stepmom for Juan Loco, but he just sees that she's nagging him relentlessly. She wants Juan to wear pajama bottoms in bed, and then she takes his phone away. Since Anya wants Juan to get the best night's sleep possible, she strips down to her thong and climbs into bed with him. After asking Juan if he finds it relaxing, Anya strokes his hair and helps him go to sleep. The next morning, Anya comes in to tell Juan to change his underwear. She has to watch to make sure he does it. Later, when Juan has finished showering, Anya is there to hand him his towel and make sure he's cleaned everything thoroughly. She tells Juan the only way she'll know if he washed his dick properly is to sample it. One thing leads to another and next thing Juan knows he's got Anya on the sink so he can eat her out. Getting to his feet, he listens to stepmom and shoves it into her twat. Taking their action to the bedroom, Juan lays spreadeagle as Anya mounts him to ride in cowgirl. Reverse cowgirl follows suit, and then Juan gets to bang Anya as she kneels before him. On her side, Anna lifts one leg as Juan spoons behind her and keeps her pussy party going until he pops deep in her fuck hole. 41:20
momwantscreampie.25.10.11.anya.olsen.your.turn.to.take.care.of.me.stepson.4k
Ugh, I’m literally stuck in this disgusting, cramped office with four gross loss prevention officers who think they’re so much better than me just because they caught me shoplifting. Newsflash - I always get what I want when I want it. But now, these men have me right where they want me - naked, vulnerable, and entirely at their mercy. It’s infuriating because I’m not used to being told what to do or being treated like some kind of...I don’t know, sex toy or something. But as they’re touching me, groping me, and exploring my body, I have to admit that it’s kind of...exciting. I mean, I’d never admit it out loud, but being bent over and fucked by four different men is a total thrill, even if it is a bit degrading. And okay, fine, I’ll say it - I’m loving every second of being their little fuck toy! Being passed around and used for their pleasure…I never knew submitting to someone could be so fun. Bent over on the desk, my delicate pussy lips spread by their strong hands, all of them gawking at me, imagining all of the fucked up things they wanted to do to me. It’s wrong, but holy fuck am I wet right now… I’m just a vessel for their cum, and it’s kind of...liberating. I mean, I’m not going to start wearing a “I’m a slut" t-shirt or anything, but...yeah. Being completely and utterly at their mercy is kind of a turn-on. And as they’re taking turns fucking me, I’m just going to have to swallow my pride and admit that, yeah, I’m enjoying this. A lot. 37:12
Shoplyfter - 2025.03.29 - Angel Windell - The Officers Gangbang
Tommy Pistol sets up some nanny cams around the house to keep an eye on the housecleaner. The cameras don't record anything, but they stream directly to his laptop whenever he wants, so he's confident he'll be able to see if the housecleaner does anything suspicious. However, when Tommy uses his laptop to check the cams, he unexpectedly catches a tantalizing glimpse of his stepdaughter Destiny Mira wearing only a towel because she just finished taking a shower. As the days go by, Tommy continues to use the cams to catch Destiny in various states of undress, spying on her more and more. Eventually, Tommy tries to sneak a camera right into Destiny's room so he can see even more of her, but Destiny suddenly comes into the room and catches him in the act. At first, he tries to lie about what he's doing, but Destiny doesn't fall for it, so he guiltily comes clean to her about his twisted desires and attraction. She's shocked and punishes him by making him squirm all the more, insisting that she'll give him what he wants. He's disgusted with himself but gives in, which leads to lustful sex. 51:36
PureTaboo - 2025.06.17 - Destiny Mira - Stepdads Forbidden Glimpses
Lesbian Stepsisters 10 - Scene 2 30:10
Lacy Lennon - [SweetheartVideo.com] - [2021] - Lesbian Stepsister - Leah Winters
Tired of summer school, rebellious Indica Marie snuck out and tried to steal tons of merchandise from the shopping mall. The plan was clearly flawed, and her only intention was to get caught, so when Officer Mancini took her to his back office for questioning, her bratty attitude remained. Seeing that he could not get to her, Mike tried a more agreeable approach and gave the girl a strip and cavity search. He even introduced his fingers deep down her surprisingly wet pussy to provoke her, but Indica’s boldness was still intact. Soon, Mike realized that scaring the crap out of Indica would not work, but maybe he could convince her to make a naughty deal, empowering the spoiled schoolgirl and getting something out of it as well. Faking reluctance, Indica sucked Mike’s cock and let him play with her perky tits as an excuse to walk away a free young woman. 37:26
Shoplyfter - 2025.07.12 - Indica Marie - Bratty And Horny
A man, Ryan (Charles Dera), has an erotic obsession with twins and engineers a situation where he marries and divorces one woman to have a stepdaughter, Alisha (Kimmy Kimm), then marries another woman so that he can have another stepdaughter, Madison (Lulu Chu), who looks just like Alisha. Ryan seemingly wants them to all be one big, happy family but the stepdaughters start to get suspicious and weirded out when Ryan's behavior changes. Especially one day when he gifts them matching dresses to make them look even more alike than ever before. The stepdaughters then get a shock to the system when Ryan announces that he's divorcing Madison's parent and that he wants Madison to stay with him and Alisha so that they can continue being a family. But Madison carefully says that she's going to stay with her parent instead. Ryan seems to understand... but when Madison's parent later pass away under mysterious circumstances, both stepdaughters realize that something's horribly wrong. When the stepdaughters confront him and learn about Ryan's twisted desires, they eventually agree to fulfill his sexual fantasy in order to stay on his good side... for now. 59:35
PureTaboo - 2025.01.21 - Lulu Chu & Kimmy Kimm - Twin Desires
Eleanor (Dana Vespoli) has recently been in an accident and is paralyzed from the neck down. She is bedridden and doted on by her loving, obedient stepdaughter Maggie (Kylie Rocket), who offers to do anything to make Eleanor happy. That's when Eleanor, who longs for sex, becomes inspired. Eleanor invites over Travis (Tommy Pistol), a man she had casually dated before the accident, and offers up Maggie for him to have sex with. The condition is that he has to fuck Maggie on the bed right next to her, so that Eleanor can live vicariously through them. Although Travis is shocked at first, he gives in, having sex with Maggie while Eleanor puppeteers everything. 50:34
PureTaboo - 2025.01.28 - Kylie Rocket - Taking It Lying Down
Marcie (Victoria Voxxx) is alone at home because her husband went out. She gets a surprise visit from her husband's sibling, Bill (Nathan Bronson), who is stopping by with a casserole dish. She pleasantly invites her in-law inside and questions why he's brought over a casserole. Bill is careful as he says he's checking up on her, revealing that Marcie is having trouble conceiving with her husband. Marcie is stunned when Bill mentions that she's infertile, which isn't true. Marcie explains that she's perfectly capable of getting pregnant, but her husband has a low sperm count and THAT'S why they can't conceive. Bill is surprised, admitting that her husband has been telling everyone that she's the infertile one. Marcie becomes angry as she realizes that her husband has lied to Bill and everyone else. They live in a religious community that believes it's a woman's duty to get pregnant, so her husband has essentially ruined Marcie's reputation to save his own. Even though Marcie is furious, she suddenly gets an idea. She begins seducing Bill, saying that Bill has proven himself already to be very fertile, so HE could get her pregnant. Bill is stunned by the offer. Marcie gloats that her husband will KNOW it's not his bundle of joy, but won't be able to say anything without damaging his OWN ego and reputation because of his lies... in other words, it would be the perfect revenge. 46:45
PureTaboo - 2025.05.20 - Victoria Voxxx - Conceiving The Perfect Revenge
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