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Whitney Oc is decorating a pumpkin when her stepson, Juan Loco, announces plans to meet friends. After reminding him of his promise to help, Whitney guides him in creating fun designs. Their decorating session turns into a joyful bonding experience f

Myra is eager to showcase a stylish outfit to her long-distance boyfriend but pauses to check on her stepbrother Nick, who's feeling down. She engages him in lighthearted conversation to cheer him up, maintaining their sibling bond and balancing her

Max and his stepmom, Cherry, have a study session interrupted by a coffee spill. After he declines a refill, Cherry expresses her coffee preferences. As they study, the atmosphere becomes charged, leading to playful affection and an exploration of th

Josephine Jackson accidentally encounters her stepson, Jimmy Bud, in the shower. She asks him politely for a towel and engages in a conversation, leading to an unexpected emotional connection. Their playful interactions foster trust and understanding

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

Diego Perez helps his stepsister Lexi Lore and her friend Sophia Sterling peel corn for Thanksgiving, sharing amusing anecdotes. They joke about gratitude, including cling wrap. The light-hearted mood continues with costumes and playful banter, celeb

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

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

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

Juan is engrossed in a video game while Diego scrolls through his phone. When Diego's phone dies, he finds Juan's stepmom, Laura, who offers a charger. Their playful interaction continues, leading to lighthearted teasing and a fun afternoon, emphasiz

Millie and her boyfriend Sam openly show their affection while visiting friends Liz and Parker. In light-hearted moments filled with playful interactions, Millie encourages the more reserved Parker to let loose. The group bonds over shared experience

Nikki and Sam are gaming when Sam's stepmother, Nelly, drops by to socialize. Sam expresses worries about Nelly's flirtation, while Nikki sees it differently. Nelly's playful teasing lightens the mood, creating a relaxed and humorous atmosphere as th

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

Asian coed Kimmy Kimm sees her stepbrother's dick and knows she needs to suck it off and ride it in her hairy pussy

Sam Bourne discovers a laptop in his dad's room while searching for him. When his stepmom, Zlata, walks in, they share a surprising moment that leads to a complex conversation about boundaries and communication. They emphasize the importance of respe

Melody Marks and Selena Imai relax on the couch, chatting with Parker Ambrose about his ideal date. Later, they invite him to help pick outfits for a date and tease him about possibly going out with him, leading to a fun fashion consultation filled w

Karina King is in her room when her stepson, Alex Charger, comes to ask about laundry. Their chat turns playful as Alex inquires about a statue. Karina reminisces about a college trophy for her party spirit, leading to teasing banter that deepens the

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

Bianca and her stepbrother Elias spend the evening in their van when a security guard asks them to leave. To lighten the mood, Bianca jokes with the guard and invites him to stay a bit longer. They share laughs, keeping the atmosphere friendly and re