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Jayden Marcos is dating Rachel's mother, Pristine Edge, and they engage in a heated strip poker game. Pristine's attraction to Jayden is evident, as she shows him everything he wants, including licking his shaft and balls. As they end, Pristine fucks Jayden in a cowgirl outfit, showcasing her physical prowess and letting him sleep. This season's Dating my Stepson follows Pristine's journey towards love.
Ivi Rein and Ricky Rascal attend a poker tournament together. Ivi tricks Ricky into thinking he has the superior hand and gives him a kiss of consolation. Ricky gives her a handjob and a pussy eating session as a prize. They sit on the couch, Ivi blows him out, and Ivi crawls on top of him. They stay together until they're satisfied. Ivi bends down to allow Ricky to crash back inside, and she rides her fuck stick to regain control. Ricky tries to blow his stack, but Ivi lets him slip out at the last minute.
Gigi Dior and Joshua Lewis plan a great vacation, with Joshua being open to her wanting his large load in her. Gigi shops for an outfit and enters Joshua's room for hot fuck. The stepmother massages Joshua's wood, causing a deep throat BJ. Gigi enjoys a rough ride in cowgirl and reverse cowgirl, waiting for Joshua to give her a doggie.
Betzz, a ballerina, performs live for her admirers, including her boyfriend Nick Ross. She enters Nick's room after a cooldown and kisses him, drawing him into her tights. She then rides like a wild person, savoring every part of Nick. Nick treats her with respect, and they both gasp as Nick thrusts up into her velvet glove. Betzz satisfies both her boyfriend and herself, completing the task on time.
Lana Smalls is excited for costume day and plans to surprise her stepbrother, Parker Ambrose, by dressing up as a space figure. She bemoans Parker's misconception that they are having sex, and Lana uses her seductive blowjob to suck him dry. She then rides Parker like a cowgirl, allowing him to dick her. The stepsiblings have a fun time, proving that gossip at school is accurate.
Kimmy and Small Hands have a fun chemistry, fucking each other over the bed. They fuck on the dining table until Small Hands cums inside her, then fingers the cum back into her.
Raul Costa and Tiffany Tatum plan a date night at their apartment, where they indulge in nude sushi. Raul is excited about the sushi and enjoys it with her. Tiffany then moves in for dessert, while Raul leans in for a kiss. They continue to mewl and mewl, and Tiffany indulges in doggie on her hands and knees. Rual helps Tiffany ride him in reverse cowgirl mode. After enjoying a final moment together, Tiffany gives Raul a slow cowgirl kiss and a quick stroke and suck.
Xxlayna Marie sneaks in late at night, but her stepdad catches her. Parker Ambrose intervenes, allowing Xxlayna to hang out in his room. Xxlayna expresses gratitude and reveals her dirty behavior. Parker shows his dirty side by face-fucking her. Xxlayna tries to ride Parker, but Parker pulls out and squirts nuts. Parker's father enters and becomes enraged.
Honey Demon, dressed in black lingerie and stockings, struts up stairs, flaunting her curves and licking her pussy. She takes off her underwear and stops to swallow Erik's cock. When the mask is removed, Honey experiences extreme face-fucking and deepthroating. She stands up, bends down, and performs blowjobs, including bouncing her curvaceous ass over Erik's cock. Honey enjoys getting fucked in various positions and enjoys getting fucked in various ways.
Lolly Dames reveals to her stepson Tony that his father kicked her out and she wants to stay with him. She confesses to having an affair with Tony's father, who hasn't had sex with her in months. Tony cracks up, but Lolly insists she keeps it a secret. They take Lolly to her bedroom, where she performs a backward cowgirl ride, and Tony reciprocates by sucking his dick.
Matty and Barbie engage in a passionate sexual encounter, with Barbie taking control of the situation and allowing her to explore Matty's body. They bond over their mutual love for each other's bodies, and Barbie's tongue melts any shyness Matty might have experienced. As Matty descends from her climax, the girls unite in a crushing embrace, and Barbie helps Matty crawl over his face, creating a lesbian 69. They continue their pleasure-filled sexual encounters, ending in a puddle of pleasure.
Aylin Tattoo, a blonde hottie, is seen in a SimplyAnal scene on vacation. She swallows a cock outside, slurping on her man's dick while gazing out to sea. Aylin then goes from pussy to mouth, deepthroats, and enjoys anal fingering. She then mounts him for a backward cowgirl ride, eagerly waiting for a sloppy titty cumshot.
Alex Coal, a casting team member, interviews Elsa Violet, a 24-year-old novice. They begin by trying on clothes and stripping Elsa naked. Juan Loco appears on screen for the first time, and Alex assists them in masturbating. Elsa steals the stage, and Alex assists in getting onto Juan's cock. She rides in reverse cowgirl, licking the bubbly coed's clit, and continues eating her out. The girls are seated, and Juan gives them a facial, giving them a fun time.
Lilly Bella, dressed in bedtime panties and a crop top, prepares breakfast for Jason X and herself. Jason approaches her from behind, squeezing her tits and pierced nipples. He then reveals his hardon through his briefs, consuming Lilly's flesh. Lilly releases the stick and sucks everything in, allowing Jason to wet his dick from behind. They sit on the couch, and Lilly lifts one thigh above her head to increase penetration. Jason then releases, giving Lilly a creampie of his scorching love.
Jay Romero calls his stepmother, Alexa Payne, to help him find his remote. Alexa flashes T&A and initially agrees to help. However, when Jay requests to view her tits, she recoils and consents to let him see and touch her pussy. Reluctant to give up, Alexa agrees to suck Jay's dick, giving him a cowgirl ride and hammering her pussy in a doggie fashion. Jay's final directive is to keep his father in the dark.
Sheena Ryder's stepson, Rion King, notices her attractiveness and is excited about breeding season. Sheena tries to win him over, but her early flirting attempts fail. Sheena surprises Rion with a BJ to encourage breeding. Sheena seduces Rion with a pussy licking and rides him in cowgirl and reverse cowgirl modes. Sheena feels pregnant after he delivers a large cream pie.
Angel Gostosa finds chaos in her living room and asks her stepbro Parker Ambrose to clean it. Parker agrees, but Angel insists she hires others. When Angel returns, the room is still in ruins, and Parker is lying on the couch. Angel sucks Parker dry, and they engage in a dogfight. Parker agrees to another fuck tomorrow.
Lilly Bell and Tonny Carrera, after dating, fantasize about Tony seeing Lilly with someone else. They meet James Duval, creating a passionate trio that fosters shared pleasure and intimacy. The performance features Lilly Bell Duval James.
Crystal Rush is cleaning the kitchen and her stepson Joshua Lewis follows her. Joshua is amusing himself by observing her and attempting to open a jar. Crystal makes fun of Joshua and demands he show her his face. Alexis transforms into a hotter version of herself and corners Joshua on the couch. Crystal gives Joshua a ride on her fuck stick, and they enjoy a new level of relationship.
Casey and Codey have a comfortable chemistry, caressing and kissing each other. They engage in powerful orgasms using a vibrator, with Casey licking his ass and sucking his cock until Codey cums.
Ricky Spanish and his stepmother Alexis Malone are on vacation, and Ricky sleeps on the couch to save money. Alexis sneaks into the living area and cuddles with Ricky, but he cannot feel at ease. Ricky indulges in Alexis's large tits, and she falls to her knees. Ricky enjoys a deep throat blowjob, and she implores Ricky to give her everything. His father discovers they are recovering from their fuck fest.
Eliza Ibarra is a new age woman who is cleansing her home after a recent heartbreak. She helps her boyfriend, Parker Ambrose, clear his heart chakra by straddling his hips and using stones. Eliza then tries to support Parker by riding in cowgirl mode, causing tension in his root chakra. Parker eats Eliza's pussy to balance her chakras, causing Eliza to scream. After giving Parker a loving pat, Eliza promises to always be there for him.
Lumi Ray, determined to save her business and achieve recognition on television, targets Derrick Pierce, a powerful and sensual man, showcasing her growing professional aspirations.