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Ashley Alexander loves Halloween for the chance to dress in slutty costumes and fill her pussy with stepbro's cum

This season of "Dating My Stepson" introduces a twist where contestants first date the mom before meeting her daughter. Featured mom Texas Patti is excited to connect with someone adventurous. During fun activities, Alex feels a strong connection wit

Marina Gold practices yoga in the kitchen when her stepbrother Alex Charter joins, feeling down. She aims to cheer him up with playful banter, despite their earlier agreement for it to be a one-time occurrence. They move to the couch, deepening their

Anya Olsen brings joy to baking, especially while preparing a Thanksgiving pie for her stepson, Juan Loco. Their playful banter hints at a special charm in her secret ingredients, creating a fun atmosphere filled with laughter and family traditions.

Juan and Nade relax on the couch until their stepmoms, Crystal and Isabel, ask them to sit on the floor. Later, the stepmoms join the boys and, through playful interactions, teach them about caring relationships. They share laughter, bonding as a fam

Boxer Jane Wild senses her coach Bruce Venture is troubled after he bet on her last fight, which didn't go well. He urges her to focus on cardio, but she prefers striking. Jane proposes a unique way to showcase her stamina, leading to a playful yet i

Robby Echo and his girlfriend Raven Lane enjoy a lighthearted day together, planning to shop for a new purse. Raven changes into a fun outfit, capturing Robby's attention and sparking playful banter. Their laughter and chemistry create a warm atmosph

Micky Muffin, married to Brady's dad, struggles with feelings for her stepson, Brady. Their awkward encounters lead to tension as boundaries blur, complicating their relationships and forcing them to confront the emotional undercurrents of their situ

Whitney and Kathryn, after arranging Christmas presents, chat about their stepsons' good behavior. They decide to surprise their partners with festive outfits and laughter once the kids are asleep. The night becomes a joyful celebration of love and h

Rissa May and her friend Alex Coal explore a fun dynamic with Rissa’s stepbrother, Nade. After a camping trip, Rissa feels uncertain, and Alex helps her brainstorm playful ways to get Nade's attention, fostering friendship and lighthearted antics.

Khloe Kapri, initially a Christmas skeptic, playfully plots to steal the holiday spirit from her stepbrother, Lucky Fate. However, as she observes him preparing a gift, she experiences a change of heart. Their humorous banter leads to a joyful celebr

Chloe Temple looks for the perfect New Year’s Eve dress and seeks her stepbrother Ricky Spanish’s opinion. Their conversation about family traditions leads to a humorous misunderstanding and playful engagement, prompting Chloe to propose a new fun tr

Roommates Ashley and Juniper discover unexpected Valentine's gifts from Juniper's stepbrother, Lucky. After realizing the mix-up, they share laughs and light-hearted moments, leading to a fun and flirty evening that strengthens their bond and celebra

Megan Marx and Parker Ambrose enjoyed a fun date night, with Megan shining in her red outfit. As they connected, she suggested extending their time together. They shared sweet kisses, playfully enjoyed each other’s company, and deepened their bond th

Redheaded goddess Scarlet Skies pranks her stepbro until he agrees to dick her down as hard and fast as she can handle

Robby Echo enjoys coffee when his girlfriend, Lana Smalls, and her friend, Chloe Temple, come home playfully. They cheer him up with lighthearted antics, and after some laughter, move to the couch, sharing compliments and creating joyful memories tog

Petite Della Cait is bitchy to her stepbro but when he accidentally gets his hand on her pussy she wants his whole dick

Cum hungry Sawyer Cassidy teases her stepbro until he gets her to lift her miniskirt and fuck her as she holds the moan

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