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Jennifer White is a stepmom now. Since Mother's Day is coming up, she begins making a list of things she wants from her stepson Jimmy Michaels.

Lexi Dona and her stepdaughter Olivia Sparkle meet their new neighbor, Stanley Johnson, who returns an item to Lexi. Olivia playfully teases Lexi about their interaction. The next day, Olivia finds them having coffee and joins in as they bond and sha

Ivi Rein embraces her love for dolls, playfully engaging with them alongside her stepbrother, Nikki. Dressed in a vibrant pink outfit, she charms him into continuing their imaginative game, leading to laughter and a spirited bond filled with creativi

Nathan helps his new neighbor, Octavia, move in, and an undeniable attraction simmers between them. Accidental touches lead to playful moments, including a light-hearted water spill that breaks the ice. Their laughter and flirtation deepen their conn

Lilian Stone values a tidy home, often challenged by her playful stepson Jayrock. While cleaning up his messes brings her joy, she enjoys dressing well while organizing. Together, they have fun tidying his room, fostering teamwork and laughter, resul

Jay Romero delivers pizza to Aaliyah Love, who playfully invites him to join her at the table. They enjoy lunch together, flirt, and engage in light-hearted banter, fostering a fun and lively atmosphere filled with laughter and connection.

Lauren Phillips embraces a fun Halloween spirit by dressing as a playful rabbit, dazzling her boyfriend, Quinton James. He’s captivated when she asks for help with her high heels, leading to playful photo moments and laughter, highlighting their chem

Usha, an enchanting brunette, had a fantastic time in front of the cameras and is eager to return. Her playful spirit and confidence in showcasing her figure made the session enjoyable. We can’t wait to see her again for her next adventure.

Oliver and his stepsister Megan engage in a light-hearted conversation while he does the dishes. She asks personal questions, and they jokingly explore the topic together. Their banter includes playful teasing and a reminder to keep things fun and fa

Jay is interrupted by his stepsister Myra, who playfully covers his eyes. When she accidentally breaks the family's TV, she asks Jay to take the blame. In return, Myra shows her gratitude, strengthening their sibling bond through humor and light-hear

Ricky Spanish, an adult, finds himself in amusing situations at home. His mother arranges for her friend Nickey to babysit while they’re away. Their playful banter turns into a fun bonding experience, leading to mutual respect and enjoyable memories

Chanel notices her stepbrother Jayden is having a tough day after a breakup. She offers support, reassuring him of his worth. Later, they share a light moment that lifts Jayden’s spirits, reinforcing their supportive sibling bond and mutual appreciat

Tanned toned milf Veronica Leal masturbates and daydreams about her stepson fucking her but the reality is way better

Bigtit milf Alexa Payne has phone sex and the real deal at the same time when her stepson bangs her bare pussy

Cum loving and well rounded hottie Spencer Scott seduces her stepson when they share a bed in a hotel room

Alyssa Bounty and Lady D are mid lesbian fuck when Lady D's roommate walks in on them and is invited to make a threesum

Athena Fleurs is interviewing Fiona Frost when her stepson demonstrates that he has a free use fuck card for Athena

The only thing hotter for stunner Zlata Shine than dressing in lingerie for a pussy pounding is getting fucked on camera

Juan is upset about being grounded and missing a party, but his supportive stepmom, Addison, offers to help him have some fun later if he completes a task for her. They share playful banter and enjoy each other's company while preparing for the outin

In this season of "Dating My Stepson," three stepsons and their stepmoms navigate complex relationships. In a recent episode, Alex and Shalina share a candlelit dinner, where initial awkwardness turns to a budding romance marked by a sweet kiss, high