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Kali, navigating the end of a relationship, seeks confidence and connection. She playfully engages with her stepson, Peter, who eventually warms up to her flirtatious energy. Their interactions foster exploration and deepen their bond, leading to a m

In "Dating My Stepson," three mothers and stepsons tackle relationship dynamics. In this episode, Shalina and Micky compete for Matthew's attention but eventually team up, sharing time with him and fostering a lighthearted atmosphere. Their playful r

When horny cougar Lilly James runs out of vibrator batteries mid masturbation she turns to her stepson to finish her off

Hotblooded milf Crystal Clark takes her turn dating her friend's stepson but all this horny mama wants is the D

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

Jade Greene has a crush on Jason, her stepson's football friend. She surprises him with chocolates and enlists Coach's help for the game. Despite Jason's reluctance, Jade's charm and enthusiasm shine as she motivates him to support her stepson, highl

Joshua Lewis finds himself alone with his friend’s stepmom, Venus Valencia, leading to an unexpected connection. They explore their chemistry through playful exchanges and flirtation, deciding to keep their unconventional relationship a shared secret

Nata and Tommy enjoy a playful and intimate moment together in bed, both on their devices. Nata surprises Tommy with a playful schoolgirl outfit, leading to shared laughter and affectionate gestures. As they explore their connection, their dynamic gr

Veronica grapples with complex feelings for her stepson, Matthew. Confiding in a friend, she acknowledges her attraction. When Matthew arrives, she flirts by asking about his interests and subtly removes clothing, leading to intimate moments that tes

Juan was channel surfing when his stepsister Amber and her friend Ashley came home from school, excitedly sharing stories about classmates. They enjoyed light-hearted banter until their parents arrived, after which they resumed their fun discussion,

In "Dating My Stepson," contestants seek love by first charming their partner's mother. This episode spotlights Juan, who impresses Tiffany's mom, Cassie, by creating romantic gestures. Their chemistry blooms with laughter, leading Cassie to approve

Sheena Ryder is a cheerful woman who loves tidying her home. Her stepson Rion notices her joy, leading to light-hearted conversations about new beginnings. Sheena suggests spending quality time together, encouraging Rion to be brave and open-minded,

This episode of "Dating My Stepson" explores the deepening bond between Micky Muffin and Matthew Meier during their second date in a jacuzzi. Their playful interactions and shared laughter in a cozy setting highlight the growth of their affectionate

This season on "Dating My Stepson," Kira and her stepson Matthew enjoy a casino-themed night filled with playful rivalry and unexpected chemistry. As their bond deepens, they share affectionate moments that highlight the complexity of their relations

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

Gigi Dior is excited for a murder mystery party but feels weighed down by decorations. Her stepson, Jodie Johnson, helps her out, and they practice their roles in a flapper costume. Their shared enthusiasm ensures they'll impress their guests at the

Ivi Rein is sleeping with BFF Rebecca Volpettis husband and when she finds out all Rebecca wants is a threesome

Big boob redhead Summer Hart is ready to play with her stepson's cock as she rides him in cowgirl and gives a titty fuck

Bigtit hottie Bunny Madison is the milf you would marry, who comes on with a slow burn that heats up super fast