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Dylan Moore and Theodora Day assist Coal Daniels in sorting through neckties, removing Coal's ties the next day. They share everything with Dylan's stepdad, giving each other kisses and baring their titties. In return, they give Coal a double BJ, a reverse cowgirl ride, and a dick in doggy. Theodora rides her face, Dylan finishes their threesome, and Coal fucks her to a creampie.
Maria Kazi and her stepbrother Parker Ambrose are packing sandwiches when Parker becomes enraged when Maria teases him about taking items from his lunch bag. Maria admits her intention to have him seize and fuck her, which leads to a violent confrontation. Maria enjoys the experience, pushing Parker onto the couch, giving him a bald pussy stiffie ride, and finally giving him a blowjob.
Ashley Alexander, her stepbrother, comes to help with dishes in the kitchen. She questions Juan about using his eyes to strip women, and they both strip off to find out if their imaginations are real. Ashley takes the lead, but Juan's dick gets in her way. She tries to suck him out, but ends up wedged between Ashley's thighs. Ashley helps Juan finish off by squeezing his load all over her tummy.
Elsa Violet wants to show her stepbrother Jay Romero her new outfit after a shopping trip. They discuss the outfit and Elsa focuses on getting a creampie. Jay is putty in Elsa's hands, threatening to fuck her. They start riding in cowgirl mode and reverse cowgirl mode, with Elsa getting one last fuck when she gets on her back.
Renee Rose visits her stepbrother Tony, who is considering attending the same school next year. They discuss attractive girls and Renee's fun with them. In exchange for Tony's help with her biology essay, Renee agrees to help. They head to the bedroom, where Renee admires her T&A and teaches Tony about cowgirl and reverse cowgirl. Renee ends their fuck fest with a mouthful of come, marking Tony's first experience.
Jay Romero is to choose his next stepsister between Lexi Lore and Chanel Camryn. Chanel has a strong first impression, but is sent away before she can fully entice Jay. Lexi interrupts them and asks Jay to take off his shirt before they move on. Lexi retaliates by removing her entire garment. Before they form a team, the females fight over him, but Lexi handles it. Chanel gets rough and tumble, and Lexi eats her out. Chanel scoots forward, allowing Lexi to sit on Chanel's face while Jay dicks her until he pulls out to pop.
This season of Dating my Stepson involves men dating the mother of a potential girlfriend before pursuing their love interests. Juan Loco aims to win over Tiffany's mother, Cassie Del Isla, by teaching him how to treat a lady. They engage in a romantic feast, with Cassie revealing her sultry figure and Juan tackling her from behind. Despite Cassie's blessing, Juan believes he will continue searching for another partner.
Parker Ambrose is to choose between Jade Maris and Scarlett Alexis as his new stepsister. Jade calls shots at the start of their date, ending with a D. Scarlett interrupts them, shoving Jade from the room and agreeing to suck Parker's cock. Despite Parker blowing his load, Scarlett blows him again, causing him to become hard again. Parker requests Scarlett to blow him away, but his desire for her to be his stepsister is evident.
Kimmy Kimm prepares food for her sleepover when her stepbrother, Parker Ambrose, tries to consume it. Kimmy tells him he is not allowed to have her food or friends. Kimmy bemoans her friend's and crush's attraction and later sits down with Parker. Parker advises Kimmy to fuck him to make her crush envious. Kimmy jumps on Parker, shows off her tits, and orders a messy BJ. Parker pulls out and gives Kimmy a sleepover in his room.
Dylan Moore is in her room when her stepbrother Jodie Johnson comes to borrow a phone charger. She flashes her tits at him and borrows his phone to lure him back into her room. She challenges him to fuck her, and Jodie realizes his stepsis is serious. Dylan cries on top of Jodie, riding in cowgirl and reverse cowgirl, and then takes her to cum town.
Jade Maris struggles with her own bed and her friend Vanessa Marie informs her about a sale on Memorial Day. They tour the house and try Jade's stepbrother's bed, but are discovered in Jay Romero's bed. They threaten to make him sleep on the couch or share his bed. Jay agrees to share his bed with them, but they wind him up by blowing him away. Vanessa pulls him out, leaving the girls to split the mess.
Jade Maris plans to celebrate Cinco de Mayo with more than a piñata. She flirts with her stepbrother Max Fills, but they don't discuss the pinata. Jade dresses up in a do-me ensemble, demonstrates seriousness by displaying her tits, and enjoys sucking Max's dick. They ride Jade's fuck stick, but Max pulls out to nut on her landing strip.
Tommy Gold and his stepsister Nata Ocean fight over a towel, causing tension between them. Nata insists on Tommy showing her, leading to a lengthy blowout. Tommy leads the stepsiblings to a 69, willing to give it his all. Nata uses a reverse cowgirl mount to ride Tommy, but falls on her side, causing Tommy to dick her down. When Tommy gives Nata a kiss, she screams.
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.
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.
After a shopping trip, Elsa Violet and Camila Cream wear new ensembles together. They bring in Camila's stepbrother, Diego Perez, to decide who is the hottest. They dress up as his favorite princess and decide to fuck both. Diego hesitates, but they make out in front of him. Elsa rides Diego's dick in cowgirl mode, and Camila reclines, allowing Elsa to glide over her tongue.
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.
Jojo Austin prefers her stepbrother's bed over her own, but Parker Sims dislikes sharing it. When he confronts her about her short skirt, Jojo offers to help with her penis. Parker admires her cock and helps her with her sexy miniskirt. They share a passionate moment, with Parker dicking Jojo down and nuting her tummy.
Madi Collins and Aria Valencia return from shopping and head to the kitchen to make snowcream. They ask Jay Romero for sperm instead, and they suck him off in a double deep throat BJ. Aria slaps Madi, and Madi rides her friend's tongue. Jay fucks Madi until she lies down. Jay feeds his stepsis a creampie, and Aria scoops up the snow cream.
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.
Myra Moans creates a video discussing makeup products, with her stepbrother Jimmy Michaels appearing. Britt Blair discusses cookies she sells and expresses desire for him. They collaborate, giving each other blowjobs and a doggy-style pussy pounding. Myra gives Jimmy a final scold before he leaves. Britt prepares cookies and directs Jimmy's sperm shot towards them, creating a delicious dessert for both.
Haley Reed, a caller on Lil Sis, shares her experience with her stepbrother Juan Loco, who used to provide her with lavish meals. However, Juan's girlfriend ended their relationship, and Haley had to give him physical affection. She was led by Alex, who shared her experience with Juan, who confessed his desire to have sex with her. Haley embraced Juan, fucked him, and smothered him. When Juan pulled out, Haley was left with no options. Alex then reveals that a transactional coupling isn't necessary.
Theodora Day enjoys spending time alone, removing her clothing and masturbating her tummy. When her stepbrother, Juan Loco, arrives home, she offers to fuck her once. After blowing him out, she slides him onto a hardboard for a stiffie ride. Despite her dissatisfaction, she lets Juan dick her in a doggie manner. Theodora rolls onto her back, opens her thighs, and lets out a mewl of joy before cumming all over her tummy.
Xxlayna Marie dreams of getting together with her stepbrother, Ethan Seeks, who is engrossed in a major sporting event. Xxlayna joins him on the couch and shows her pussy and tits, causing Ethan to break down. They continue their pussy party, with Xxlayna obstructing Ethan's vision of the game. Ethan delivers a final blow to Xxlayna's back before shooting his full in her face.
Juan Loco, a candy lover, loves Easter. His stepsister, Madi Collins, taunts him with a basket of treats, suggesting he eat her pussy instead of candy. Madi leaves the basket beside her sheer lingerie, and Juan decides to eat the pussy. Madi falls backwards in bed, inviting Juan to eat his treat. In return, he gets a blowjob from Madi. Juan Loco loves Easter because he loves candy.
Love coach Alex Coal hosts a hotline on Lil Sis, where Parker Ambrose discusses Lulu Chu's affair with Brooke Barclays. Brooke threatened to alert Parker's father if he found out again. Lulu hasn't taken the situation seriously, and her mother has been playing tricks on him. Parker chastises Lulu with a hard kiss, eating her pussy and having her suck his dick. Lulu cowgirds up to Parker's hardon, giving her a final orgasm before he finishes. Lulu tries to get Parker in trouble by stealing his clothes, but he gets out.