Reverse Cowgirl (221)

Steve (Elias Cash), his girlfriend Cassie (Leana Lovings), and their mutual friend Danny (Victor Ray) are playing poker. When Cassie takes a break and goes into the kitchen to make snacks, Danny suggests a wild bet: whoever loses the next hand gets to fuck the other guy's girlfriend. Steve playfully accepts, not thinking the bet is serious. But when he loses, he finds out that Danny was completely serious about it. When Cassie finds out about the stakes of the bet, she seems furious and decides to go along with it to make Steve feel bad for using her in a bet. Steve eventually leaves, dejected and humiliated, but once he's gone... the truth reveals itself. 41:39
PureTaboo - 2025.11.11 - Leana Lovings - Up The Stakes
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
Janet (Lexi Luna) is catching up with her longtime friend, Phil (Leo Vice). Their friendly conversation takes a turn, however, when Phil mentions that he's found out that Janet has become a sex worker. He holds no judgment against her for it, which momentarily reassures her, but things get weird when Phil starts musing about potentially booking her services for himself. At first, Janet thinks he's joking, but when it turns out that he's serious about it, she is totally disgusted. She eventually agrees to give her so-called 'friend' a taste of her goods, but warns him that it won't cost him anything... except their friendship. Phil takes her up on it, so Janet has intense, energetic sex with him while putting on the same fake 'enthusiastic' face she's put on for her other clients, ultimately ending their friendship with a resounding bang. 41:34
PureTaboo - 2025.10.07 - Lexi Luna - Parting Shot
Penny (Nicole Doshi) is estranged from her family and down on her luck. That's why she's so surprised one day to discover that her chauvinistic grandparent left her his entire estate in his will. It was no secret that he hated Penny, especially her boldness in the face of men, so she can't imagine what would have prompted the change of heart before his passing. But when she talks to Jack (Tommy Pistol), the lawyer overseeing his estate, it becomes clear that this wasn't so much a change of heart as one final reckoning. Penny shockingly learns that in order to get her inheritance, her grandfather left one perverted condition: Penny must submit to a man's sexual desires, doing everything he wants, no matter how humiliating. Penny is disgusted, and even more so when Jack insists she must have sex with HIM that very instant. When Penny argues, Jack even goes so far as to enlarge the requirements, insisting that she must now have anal sex with him to boot. Penny is still shocked, but her desire for a better life wins out, prompting her to accept the terms. She has anal sex with the lawyer right in his office, all while his paralegal (Kasey Warner) watches from the sidelines while chatting nonchalantly with Jack. 42:18
PureTaboo - 2025.09.16 - Nicole Doshi - Submitting To His Will
After his parent's sudden passing, Rick (Isiah Maxwell) is left to pick up the pieces, including making all the arrangements for the funeral. To make matters even worse, it was discovered in his parent's will that he had a younger mistress to whom the deceased even left some of his inheritance. Rick is eager to help his family move past this, but he ends up getting a surprise visit from the mistress in question, Chrissy (Aria Sloane). Despite his anger, Rick humors her and allows her inside, after which he learns that Chrissy wants to attend the funeral despite the entire family forbidding it. She pleads with Rick, eventually offering him to have his way with her body in exchange for her being able to attend. Rick is disgusted, but takes her up on her offer, leading to a rough sex session that he never expected to have. 41:46
PureTaboo - 2025.07.29 - Aria Sloane - Nothing She Wont Stoop To
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
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
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
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 patient, Tommy (Tommy Pistol), is heading into a routine surgery. He's a bit nervous, but the nurse (Anna Claire Clouds) assures him that everything will be fine. However, just before the procedure begins, the nurse and the surgeon (Ashley Lane) start acting a bit suspiciously. When Tommy becomes fully alert after the surgery, he finds himself in the same room, but now he's all alone... and something feels very, very wrong. He frantically removes his bandages, and is horrified to see that his penis is completely gone. Tommy panics, but he finds a note telling him to go to the basement. Tommy enters the basement, and is shocked to find that the surgeon has transformed into a terrifying monster, and she's using Tommy's detached penis to fuck the nurse. Tommy pleads for his cock back, but the monster says it will cost him his soul and much more, because she wants to create a human-demon hybrid. Tommy is desperate, so he agrees to the bargain. Tommy's dick is reattached to his body, but now he has to fulfill his half of the deal by having a threesome with the monster and the nurse until their twisted desires are satisfied... 47:16
PureTaboo - 2025.03.26 - Ashley Lane & Anna Claire Clouds - Manhood
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
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.” 47:20
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. 42:58
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. 42:00
MomSwap.2021-10-11.Jupiter Jetson, Katie Monroe
Mylf stepmoms Sheena Ryder and Dee Williams discuss how bad their respective stepsons Anthony Pierce and Cody Carter have been misbehaving lately, being extra rude and demanding. Sheena and Dee decide to get together and punish the boys by spanking them and then swapping and fucking them until they start behaving like good boys again! 59:59
MomSwap.2021-08-30.Dee Williams, Sheena Ryder
Flight attendants Crystal Rush and Kaylynn Keys are on their way home from a long trip, and their stepsons, Nade Nasty and Johnny the Kid, can’t wait to see them. Thinking their stepmoms may have brought presents back from their trip, Nade and Johnny dig through Crystal and Kaylynn’s luggage. But when the men discover their stepmom’s “vibrating swords,” Crystal and Kaylynn give the two gifts they won’t soon forget. 43:51
MomSwap.2021-08-16.Crystal Rush, Kyla Keys
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. 46:58
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! 39:12
MomSwap.2021-07-19.Casca Akashova, Janie Erixa
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
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