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Lacy and Macy are on a quest for Christmas gifts but frequently run into Macy's stepbrother, Jason, who warns them to be cautious. Their playful banter turns into lighthearted mischief, leading to shared laughter and a memorable experience that stren

Jennifer White wants a baby, and if her husband won't give it to her, then her stepson Diego Perez will have to do.

Kenzie, participating in a sleep study, becomes disoriented at night. Her stepbrother Lucky notices and offers to help. When she behaves unexpectedly during a nap, Lucky tries to wake her, realizing she’s teasing him. They share a laugh, strengthenin

Aiden Ashley is a confident woman who, while enjoying personal time in stylish lingerie, is interrupted by her stepbrother, Charlie. Instead of shying away, she embraces the moment, leading them into a playful and intense exploration of their mutual

Petite besties Molly Little and her friend Nikki Nicole get a holiday pussy pounding from Molly's well hung stepbrother

This season of "Dating My Stepson" features a twist where potential partners must impress their date's mother first. Cherry, Lindsay’s mother, takes Parker on a fun dinner date with s’mores and games, allowing them to bond and explore their connectio

Quinton James is enchanted by Jennifer White's beauty, finding joy in simple moments like chores. A playful water fight leads to laughter and sweet kisses. They share lighthearted, intimate moments in the living room, filled with warmth, affection, a

Cory eagerly prepares a festive New Year's Eve, dressed to impress in hopes of catching her stepson Diego's attention. She adds a fun surprise behind a curtain, creating a playful atmosphere. Their light banter leads to a joyful celebration as they w

In "Dating my Stepson," young men seek love by connecting with potential girlfriends' mothers first. This episode features Bunny Madison and Parker Ambrose enjoying a picnic and games, highlighting their chemistry and playful interactions, sparking c

Bree, Jason's stepmom, is frustrated with his messy room and creates a task list to motivate him. She introduces a reward chart with stars to encourage responsibility. After Jason cleans well, Bree is proud and plans to continue helping him develop g

In "Dating my Stepson," the guys must win over their date's mother first. Millie Morgan sets up a fun date with Parker, featuring palm reading and an outdoor massage. They bond and share laughs, but Parker reveals hesitations about dating Millie's da

Olivia Sparkle wants a fun night but faces an internet outage. She confides in her stepbrother Charlie Dean, and they lighten the mood with playful banter. As they bond without digital distractions, their evening takes a humorous turn when their pare

Chris Lockwood struggles with his pants, prompting his stepsister, Scarlett, to offer help. Their interaction becomes awkward yet playful, deepening their bond. Later, Scarlett asks Chris for assistance with her skirt, leading to shared moments and a

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

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

Scarlet Skies and her stepbrother Nick debate cooking for their Fourth of July gathering, leading to a fun cook-off suggested by Scarlet's friend Selina. As they compete, mishaps ensue, but they embrace teamwork and laughter, culminating in a festive

Myra feels overwhelmed by the pool party outside and seeks relaxation in her bedroom. Her girlfriend, Haley, notices her anxiety and offers comfort. They share gentle kisses and laughter, using a calming device. Together, they create a peaceful, inti

Big tit milf Alexa Payne makes a deal with her stepson that they will not wear shirts which leads to a pussy pounding

Jodie Johnson seeks a new stepsister and explores Anna Claire Clouds' distinctive, alternative style. Initially intrigued yet uneasy, he discovers her self-care items and enjoys conversations about astrology. They bond over their differences but deci

Jay Romero returns home from college to find his new stepsister, Riley Star, in his bed. As they navigate their unexpected blended family, they bond over shared experiences, homework help, and car borrowing, striving to strengthen their sibling relat