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New spinner Isabella Jules does some stepbrother role play with Katie Kush acting as the enabling horny girlfriend

When chess club is cancelled Teal Conrad plays strip chess with her stepson and ends up riding his stiffie

In "Dating My Stepson," contestants seek love by first charming their partner's mother. This episode spotlights Juan, who impresses Tiffany's mom, Cassie, by creating romantic gestures. Their chemistry blooms with laughter, leading Cassie to approve

With her big tits and ass Lolly Dames doesn't have too much trouble coaxing her stepson into letting her stay with him

Whitney OC is a yoga instructor offering personalized at-home classes. She guides her student, Codey Steele, through essential stretches and poses, fostering professionalism and a friendly atmosphere. They focus on mindfulness and physical well-being

Casey prepares a special evening for her girlfriend, Diamonnd, complete with playful surprises and affection. After a tender reveal, they share kisses and intimacy, exploring their connection with joy and laughter. The night culminates in love, creat

Matty arrives in a stunning outfit to meet her friend Barbie, who is equally stylish. Feeling nervous, Matty relaxes as Barbie affectionately guides her. Their sweet moments deepen their bond as they explore tenderness and closeness, enjoying their n

Freya Parker visits her friend's home and shares her admiration with Mr. Legend, her friend's dad. They engage in playful banter and grow closer while enjoying light-hearted moments in the living room. Their connection deepens, leading to a cheerful

Freya Parker has a crush on her roommate, Chanel Cameryn. After revealing her feelings, they share a light-hearted moment that leads to mutual affection. As they explore their newfound connection with laughter and tenderness, they deepen their bond a

Theodora Day is excited for some alone time at home, but her plans change when her stepbrother, Juan, arrives. Instead of being alone, she visits him, and they share a playful and unexpected moment of connection, exploring their bond in a fun, lighth

This episode of "Dating My Stepson" explores the deepening bond between Micky Muffin and Matthew Meier during their second date in a jacuzzi. Their playful interactions and shared laughter in a cozy setting highlight the growth of their affectionate

Kendra Heart is frustrated with her husband and stepson for not helping at home. Dressed casually, she cleans when her stepson Parker unexpectedly arrives. They engage in playful banter, and as the day progresses, they share humorous moments, navigat

Ivi Rein and Ricky Rascal enjoyed a fun date night at a poker tournament, where Ivi playfully misled Ricky and won his chips. Afterward, they moved to the couch for light banter and flirting, sharing affectionate moments and deepening their connectio

Lilly and Blake, close roommates, enjoy a playful moment while trying on outfits, hinting at their chemistry. Tension rises when Lilly's boyfriend Robby joins. They decide to have fun together, sharing laughter and stories, creating lasting memories

Maya Woulfe feels low after her breakup as Valentine's Day nears, so she spends time with her friend Liz. When Liz's boyfriend Robby joins them, he suggests they stay in for dinner. The night turns playful and fun, lifting Maya's spirits as they bond

Josephine Jackson rents a beautiful vacation apartment, causing her stepson Alex to feel frustrated about his hostel stay. As they discuss their feelings, tension builds, leading to an unexpected kiss. Realizing the time, they grapple with their newf

Jennifer White is washing dishes when her stepson Dylan Ledger seeks advice on starting a business. Though his idea is promising, he struggles to find clients. After asking her to be a reference in exchange for a back massage, they share a supportive

Irina Cage exudes confidence as she prepares for a special evening with her boyfriend, Raul Costa. Their playful banter and intimate dance create a warm atmosphere, deepening their connection. They enjoy affectionate gestures and create memorable mom

Sera Ryder and Jayden Marcos return to his house after a fantastic date. Excited for their first sleepover, Sera changes into Jayden's letter jacket, sparking playfulness and warmth. They share laughter, deepen their bond through cuddling, and enjoy

Myra Moans expresses herself freely, causing awkward encounters with her stepbrother, Parker Ambrose. When she playfully calls for his help to find an imaginary ring, they share a surprisingly intimate moment. Their teasing evolves into a deeper conn