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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

Jay Romero fills bags with pantry food, aiming to improve his wellness, while his stepsister Chloe playfully challenges him to stick to his goals for a week. As she bakes delicious treats, their friendly competition heats up, ending with Chloe claimi

Brady Bud thinks he’s alone at home and watches a movie, but his stepmom, Josephine, is also there. She checks in on him, discovers his interest in older women, and suggests a neighborhood drive. They bond over a light conversation about relationship

Megan Marx enjoys casting and engages in a delightful Q&A with Emma Rosie, boosting her confidence. Afterward, Parker Ambrose joins them, creating a playful atmosphere. The trio collaborates effectively, sharing laughter and camaraderie while capturi

Lusty milf Cherry Kiss makes up some shamrock shakes and then tells her stepson she wants his personal cream on top

Rachel Cavellis stepson swears hes not using her shampoo to jerk off but he still accepts her help to get off instead

Sawyer Cassidy and Eva Generosi are swingers who have invited Emma Rosie and Melody Marks for a lesbian playdate

Thicc milf Abby Rose knows her stepson wants her and she realizes she wants to get a rough pussy pounding from him

In January 2025, Amirah Adara shares her excitement for a relaxing massage, captured by her husband. She enjoys the soothing experience and playful moments with her therapist, including shared affection and laughter. The session fosters deeper connec

Alexis Malone supports her stepson Parker Ambrose in his fitness journey and enlists his help with moving boxes for a family addition. As a thank you, Parker chooses a dinner of steak and potatoes, leading to a relaxed and fun evening that deepens th

Aleks Foks radiates confidence and energy in the spotlight, embracing the excitement surrounding her. She values taking time to enjoy moments with others, eager to make the most of their time together and treasure each interaction.

Rika enjoys her rooftop patio before showering and dressing in chic lingerie, feeling confident for an evening with her boyfriend, Stanley. They greet each other warmly, sharing playful moments filled with laughter, affection, and a deeper connection

Raul searches for his laptop in his dad and stepmom's room and discovers romance diagrams. Veronica, in her robe, explains her desire to revive their relationship, feeling a bit shy about it. They bond over ideas for rekindling romance, emphasizing t

Desiree Dulce is suspicious of her daughter's boyfriend, Diego Perez, possibly taking her belongings. When she confronts him, they engage in a playful and flirty exchange, leading to a fun adventure that deepens their connection and ends with mutual

Beaver explores adulthood and shares his curiosity with friend Emily. After an unexpected moment, they engage in innocent discussions about feelings. Emily leaves content, and Beaver talks to his dad about relationships. A rumor about his mom arises,

Beaver explores his feelings about relationships and sexuality, which catches his mom's attention. Concerned, she discusses it with Beaver's dad, who plans a talk with Beaver. Seeking clarity, Beaver invites his friend Emily over, and they connect, e

Willis and Johnny had a friendly competition, with Willis winning a visit to Blair's room. Unprepared for the occasion, he found himself in a playful situation. They shared flirtatious banter, kisses, and laughter, creating a memorable and enjoyable

Bud Bundy invites his friend Rob over, attracting attention from his mom Peg and sister Kelly. As they playfully compete for his time, Peg settles Rob on the couch. Bud returns to a messy couch but tries to keep it light. The scene features friendly

Janet and Crissy prepare for new roommate Jack, confronting landlord issues over mixed-gender living. They suggest Jack pretend to be gay for acceptance. When Crissy visits Jack, unexpected moments arise, while playful interactions spark between Jack

Jennifer Amton captivates Marco in her simple dress and heels, sparking undeniable chemistry. Their playful interactions and affectionate exchanges deepen their bond, leading to a heartfelt moment filled with laughter and intimacy, leaving both feeli