Side Fuck (101)

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
Brenda (Kimmy Kimm) had her heart in the right place when she agreed to be a companion to a terminally-ill man, Gerry (Robby Apples), platonically spending time with him during her summer vacation. But Gerry showers her with compliments and gifts, to the point where it's almost overwhelming... and actually DOES become overwhelming, especially when he gets upset at her for talking about going to college. During the heated confrontation, Gerry guilt trips her into delaying her college plans and moving in with him. Brenda, secretly having only agreed to move in since she figures he won't be around much longer, tries to make the best of the situation. But weeks later, it becomes too much and Brenda's miserable about putting her own life on hold. She can't take it anymore and tries to figure out a way to break things off with Gerry, despite feeling guilty at the idea of leaving a dying man. When Gerry suggests changing the terms of their arrangement to have sex, Brenda agrees to it, realizing it's a way to give him one last good memory before telling him she wants to end their arrangement. But will it really be that easy? 42:09
PureTaboo - 2025.05.06 - Kimmy Kimm - His Dying Wish
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
Amanda (Kenna James) is visiting an old friend, Lance (Pierce Paris), who is now a wealthy businessman. They have mostly drifted apart over the years, but occasionally get together for cake since they have the same birthday. Today is their 30th birthday, so Lance hints at a promise Amanda made. She doesn't remember, so he says that 10 years ago, he expressed feelings for her... She turned him down, but said that if they were both single at 30, they would marry each other. Amanda is in shock, but remembers the promise now. However, she says she only made the promise to turn him down gently. Lance gets angry, and accidentally lets it slip that he made sure she'd be single at 30. Amanda demands to know what Lance is talking about. Lance tries to say it was nothing, but she doesn't fall for it, so he admits he secretly convinced all her boyfriends to leave her. He declares he's better than all of them anyway, and can give Amanda a life of luxury. But Amanda is disgusted that Lance would go so far. Lance suggests they could at least try being intimate - if it's the best sex Amanda's ever had, they'll get married. And if not, he'll forget all about her old promise. Amanda is still disgusted by his behavior, but she realizes this might be her best chance at getting him to back off for good... 43:24
PureTaboo - 2025.04.22 - Kenna James - Pinky Promise
Kevin (Tommy Pistol) has been looking after his roommate, Jamie (Jennifer White), while she's been too sick to work. Dedicating all his time to her has turned out to be something he truly cherishes, but perhaps he's grown slightly too attached to this new routine... Now that Jamie's feeling better, she's been looking for a new job to get her life and finances back on track, and this sets off alarm bells in Kevin's mind. The last thing he wants is for Jamie to lose her dependency on him, and he must find a way to keep her close. That's when Kevin devises a devious plan to sabotage Jamie's job search, incrementally stiffling her prospects while cutting her mental stability down at the knees. Jamie has no idea that Kevin's doing this on purpose, and she plays right into his hands. Her ignorance leads to misplaced gratefulness... and eventually her getting seduced into Kevin's bed, giving him exactly what he's always desired. 54:13
PureTaboo - 2025.04.15 - Jennifer White - Need You To Need Me
An aspiring actress, Bethany (Alison Rey), goes to an audition for a commercial. As she waits for her turn, she listens in on a conversation between two other actresses, Yvette (Ana Foxxx) and Deedra (Ember Fiera), who are also auditioning for the role. At first, Yvette and Deedra grumble because they think that doing a commercial for a deodorizing foot spray is beneath them. But then Deedra gets a text message from her agent saying that the commercial is going to be made by Chris Dillon, an actual movie director, causing Deedra and Yvette to become excited. Bethany is surprised but also nervous, realizing that if she can impress Chris, this could finally be her big break. Eventually, the casting director, Grace (Casey Calvert), comes out and tells Bethany that it's her turn to audition. Grace leads Bethany to another room, where a man and a woman are waiting. Grace introduces the woman as Tina (Hazel Grace) and the man as Chris (Michael Vegas). With that, it's time for Bethany to audition in front of these three people. Bethany says the lines for the commercial and also shows off her feet, doing her very best. Grace, Tina, and Chris talk quietly amongst themselves, and then Grace thanks Bethany for coming, saying they'll get back to her. Bethany is devastated as she realizes that they didn't seem very impressed with her. She offers to try again, but Grace turns her down. Grace and Tina then leave for lunch, and Bethany gets desperate. She talks to Chris alone, pleading for another chance. And this time, she'll do ANYTHING to make a lasting impression... 40:47
PureTaboo - 2025.04.08 - Alison Rey - Foot In The Door
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
Rose (Summer Col) returns home from studying abroad, and is greeted by the family butler, Stuart (Tommy Pistol). We find out that Rose's parents died in an accident, and she inherited half the estate. The other half was bestowed to Stuart. Rose says they'll make the most out of this odd situation of owning the house together, and that of course he doesn't have to wait on her anymore. Stuart seems surprisingly offended, so she quickly agrees that he can continue to look after her. The next day, Rose is surprised and embarrassed when she sees that Stuart is washing her panties by hand. He makes a comment about the bold color and cut of her panties, making her even more uncomfortable. On another day, Rose is about to have a meal when Stuart startles her by tucking a napkin into her neckline. Rose is annoyed and says she's too old for that. Stuart acts innocent and apologizes for the mistake, but touches her lap as he tries to put the napkin there instead, annoying her further. Later that day. Rose comes out of the shower, only to find Stuart waiting right there in the bathroom with a towel. She angrily says he's being a creep. Stuart admits that he's been lusting after Rose. She is upset and doesn't want to live with a creep, but also doesn't want to give up her share of the house. Stuart offers to give it all up and leave her alone... if Rose has sex with him one time. 50:54
PureTaboo - 2025.03.18 - Summer Col - Being Of Service
When busty stepmoms Kiki Daire and Natasha Nice get the news that their respective stepsons Alex Jett and Tyler Nixon are leaving for college soon they devise a plan to convince them to stay with them. Natasha and Tyler come over to Kiki’s place and the two stepmoms tell the boys that they know they wanna go away to get some college chicks, but they’ll never find women like them over there, better to stay put and let their stepmoms really take care of them, exactly how they deserve. 54:13
MomSwap.2021-06-07.Kiki Daire, Natasha Nice
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. 45:31
MomSwap.2021-04-26.Carmela Clutch, Carmen Valentina
31:37
Lacy Lennon - [Wicked.com] - [2019] - Faithless Sc2 - 4K
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
Beth (Little Puck) and Max (Isiah Maxwell) are happy newlyweds moving into a home together. But things quickly take a strange, dark turn as unexpected and otherworldly events shatter their sense of normalcy. From Beth being locked in a room by an unseen presence to Max being pulled across the kitchen by unseen hands, whatever is going on is only getting worse. It's slowly revealed that Beth is keeping something from Max. Something about a tragic accident she was involved in. It seems that whatever is haunting them wants the truth to come out... But is everything really as it seems? 45:01
PureTaboo - 2025.03.11 - Little Puck - This Is My House
A woman, Vicky (Codi Vore), who is down on her luck, has been couch surfing for months, but she's running out of willing hosts. A friend, Marcus (Seth Gamble), generously offers to let her stay at his place for as long as she needs, which she is so thankful for. Marcus tries to play it off and insists that she goes to take a shower and settle in. Vicky is relieved as she steps into the bathroom and strips down, climbing into the shower. For the first time in months, she feels the stress washing off her like the water across her naked body. But as she's washing, Marcus barges in and insists on watching every intimate moment, his eyes hungry... It quickly becomes clear that his offer wasn't so selfless after all, but if Vicky wants to keep a steady roof over her head, she'll have to go along with whatever he desires. 45:58
PureTaboo - 2025.02.18 - Codi Vore - A Friends Hospitality
A Sunday school teacher, Ms. Mitchell (Syren De Mer), invites one of her students, Theo (Nathan Bronson), to her house. To his shock, she reveals that the mobile app she encouraged him to put on his phone secretly monitors his internet activity, so she knows he's been watching porn. Theo begs Ms. Mitchell not to tell his parents, saying he was just curious because he's a virgin. Ms. Mitchell then shows that her intentions have never been pure as she tells him that those nasty videos will lead him astray. BUT if he lets her show him how to have sex the way God intended, she won't ever have to talk to his parents... 44:51
PureTaboo - 2025.02.25 - Syren De Mer - God Is Always Watching
A marriage counselor, Dr. Taylor (Dee Williams), is surprised when her client Sam (Oliver Davis) shows up for his latest appointment without his wife. Sam explains that his wife was in a terrible accident, and is now in the hospital on life support. He acts distraught, saying that he feels lonely and touch-starved. Dr. Taylor assures Sam that his wife would understand if he sought companionship during this dark time. But to Dr. Taylor's surprise, Sam pleads for HER to have sex with him, saying he needs something to keep him going. Dr. Taylor is hesitant but sympathetic, and has tender sex with him... only to receive another nasty surprise. 46:55
PureTaboo - 2025.02.04 - Dee Williams - Im Sure Shed Understand
Law professor, Neal (Ryan Mclane), and his graduate assistant Brooke (Lacy Lennon) review all of the case evidence they have collected on student teacher affairs at Neal’s house. He believes his colleges in believing they did nothing wrong while she sides with her fellow female students. She things the older male professors took advantage of their power, even if the girls were the aggressors. To prove her point, she asks why he chose her to be his assistant, and why they are reviewing this case in his house instead of at school. As she questions him, she climbs on him and starts rubbing his cock. She makes him tell her that fucking her is very, very wrong. But of course that is not enough for either of them to stop. She takes out his cock and starts deep throating him and stroking him to get him ready for her tight little pussy. Then she sits on his dicks and rides him hard. She shows him exactly why all those professors were willing to risk their careers, marriages, and reputations just to fuck a student. She works him over until he explodes all over her red bush. 29:11
Lacy Lennon - [SweetSinner.com] - [2020] - Student Bodies 8 Sc4
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
25:11
Lacy Lennon - [Wicked.com] - [2019] - He Loves Me In Plaid Skirts And Panties Sc2 - 4K
Anya and Ellie are both desperate for grandchildren! They've tried everything to sabotage their stepsons, Jimmy and Nicky, hoping to get their girlfriends pregnant. Desperate to have babies back in the family and still being attractive and fertile ladies, they plot to get impregnated by each other’s stepson. With the excuse of teaching the boys about the basics of sex and how to keep their girlfriends satisfied, they lure them into a steamy session. As Jimmy and Nick are fucking each other’s stepmom, they feel tempted to swap, pushing their own boundaries by making babies with their stepmoms! 47:52
MomSwap.2024-01-15.Anya Olsen, Ellie Taylor
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
Selena (Sarah Arabic) is married to Eric (Isiah Maxwell). But one day, Selena has a chance encounter with a delivery woman, Katie (Lily LaBeau), and sparks fly. Selena realizes that she's not straight, and this leads to a secret affair with Katie. But things get serious and Selena decides she wants to divorce Eric since it's not fair to any of them. When Eric returns home, Selena gives him the divorce papers. She has Katie by her side, revealing that she's been having an affair, and Eric gets upset. Betrayed, he refuses to sign the divorce papers. The two women beg him to reconsider, and that's when he gets a sinister idea: he'll sign the papers IF the new happy couple lets him fuck them both. 48:53
PureTaboo - 2025.06.24 - Sarah Arabic & Lily LaBeau - A Costly Divorce
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