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Pristine Edge encourages her stepson, Jimmy, to date her friends. In this episode of "Dating My Stepson," Cassie Del Isla cooks with him and flirts, despite her usual preference for older men. The playful atmosphere fosters innocent attraction as the

Blaire Johnson felt unexpected emotions as her stepson Jimmy prepared to move out. When he sought her help to find an apartment, jealousy arose. Later, she playfully suggested he stay, hinting at a deeper bond, which solidified their complex relation

After a tiring day, Danii asked her stepson Parker for a foot massage to ease her discomfort. They shared playful teasing and bonding moments, enhancing the experience with lotion. Their connection deepened as they enjoyed relaxing, laughing, and sup

Jennifer White is a supportive stepmother to Damon Dice, navigating the complexities of their relationship through small mishaps and moments of care. As they deal with various situations, the need for healthy boundaries and open communication in a bl

Jayrock is exploring the link between physical traits and hormone levels for a school project, making his stepmom, Emily, uneasy. After a conversation with his dad, Emily answers his questions but finds the dialogue awkward. They navigate misundersta

Crystal Rush faces the challenge of managing her rebellious stepson, Johnny, who avoids chores by creating distractions. Aiming to foster respect and responsibility, she sets clear boundaries and encourages participation in household tasks. Their ope

Jasmine Daze prepares for a special date night by choosing a confident outfit and dancing to music. When her stepson Joshua enters, they chat about soccer, and after some light conversation, she teaches him dance moves, creating a playful and joyful

On graduation day, Jay's stepmom, Jaimie, is excited to support him but faces an awkward moment when her dress zipper gets stuck and Jay helps her. This uncomfortable situation creates tension, but they work through it and move on, ready to celebrate

Codey Steele navigates his new life after his dad marries Reagan Foxx. An awkward breakfast incident leads to playful moments as Reagan helps him prepare for an important interview. They establish boundaries while keeping their relationship lighthear

Christie Stevens and her stepson Tony faced an unexpected challenge when their flight was canceled, forcing them to share a hotel bed. As they navigated the awkwardness of the situation, both tried to find comfort and support each other despite their

Makayla Cox enjoys a relaxed morning while her stepson Logan watches, plotting to impress either her or his stepsister, Hannah. He creates a playful "love potion," which leads to comedic misunderstandings, especially when their dad unexpectedly retur

Jay Romero prepares a thoughtful Valentine's Day gift for his stepmom, Alexa Payne, including a cozy sweater and scented candles. He surprises her with elegant lingerie, but she declines to try it on. They share a lighthearted moment, hinting at mutu

Vanessa Cage made lunch for her disrespectful stepson, Jason, and encouraged him to be more proactive. Despite lighthearted banter, boundaries were tested. Recognizing the need for respect, Vanessa aimed to foster a better dynamic in their relationsh

In "Dating my Stepson," suitors aim to impress mothers before dating their daughters. In this episode, Jayden Marcos tries to win over Pristine Edge through a poker game. Their playful banter leads to a surprising connection, leaving viewers curious

Lauren Phillips seeks help from her stepson's friend Ricky's stepmom, Crystal, regarding their behavior. They hold a candid discussion with the boys to understand their feelings on relationships. The adults provide guidance on communication, boundari

Hot milf Liv Revamped wants her stepson's treats this Halloween so she seduces him into a finger bang and stiffie ride

Cum craving mama Jesse Pony seduces her stepson until she gets to enjoy his big dick in her tight greedy fuck hole

Jimmy and Jay sneak a peek at Jimmy's stepmom, Jessica, during her live stream. After some playful interactions and outfit changes, Jessica invites them to join in her fun, directing a lighthearted scene. They agree to meet again for more enjoyable t

Alyssia Vera prepares a special wellness tea for breakfast, prompting her stepson, Jimmy Michaels, to pause a call with friends to connect with her. They share a cozy moment discussing their lives and dreams, highlighting their supportive family bond

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