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During Thanksgiving, Katie invites her friend Skyler to join her family, including her mom Lindsay and stepbrother Jay. Playful interactions arise when Lindsay suggests Jay take Skyler to the movies. The group enjoys a fun meal, dessert, and lighthea

After a tough week, Josephine Jackson opts for a soothing bath but finds her massage appointment canceled. Seeking help, she calls her stepson Sam, who agrees to assist. She starts with a foot massage during her bath, and later, they continue in the

Charlie is adjusting to his new stepmom, Nicole, who is passionate about fitness. During a couple of encounters, they share friendly conversations while she works out. Intrigued, Charlie joins her, and their interactions revolve around encouragement

Max is frustrated that his older stepsister Angel is in charge and prevents him from having a party. After some back-and-forth, Angel establishes her authority with a fun challenge, ultimately allowing Max to host his party if she can join in the fun

When bigtit teen Rissa May finds her stepbrother practicing his swing, she gives his big bat a ride in her shaved pussy

Busty milfs Cassie Del Isla and Natasha Nice enjoy their stepsons' cocks in a glory hole before riding them to creampies

Bigtit milf Cassie Del Isla wants a baby and is happy to let her stepson and his friend seduce her for a double delight

Angel Windell gives her stepbro cake on her nipples and her pussy pie to her stepbro to celebrate his birthday

Bigtit milf Sasha Pearl has her stepson and his friend help with chores then give her pussy a good pounding

Katie and Sera excitedly sort through Valentine’s gifts when Sera's stepbrother, Jay, passes by with gifts for his girlfriend. They invite him in to share their playful decorations, sparking a fun and light-hearted interaction filled with laughter an

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

Amber Summer wants her stepdad's dick but when she can't have it she and Skyler Storm turn to his son for a good time

In this season of "Dating My Stepson," three stepsons and their stepmoms navigate complex relationships. In a recent episode, Alex and Shalina share a candlelit dinner, where initial awkwardness turns to a budding romance marked by a sweet kiss, high

Renee Rose often borrows things from her stepbrother Juan Loco without asking, frustrating him. When he confronts her about wearing his shirt, she suggests sharing everything. Later, a playful moment in Juan's room leads to unexpected bonding, deepen

In this episode of "Dating My Stepson," Micky Muffin and Alex Charger bond over a round of golf. Despite a mishap with her swing, they share playful moments and laughter, leading to a growing chemistry. Watch their connection develop on this unique o

Lana and Sera's Memorial Day party takes a turn when they unexpectedly find themselves without dates. Their stepbrother Ricky drops by, igniting playful banter and laughter over snacks. Curious antics follow, strengthening their bond as they enjoy th

Max Fills seeks the perfect stepsister and explores a candidate's room, discovering her playful side. Teasing each other leads to light-hearted moments, including whipped cream antics. Their chemistry grows through laughter, teasing, and affectionate

Oliver and his stepsister Megan engage in a light-hearted conversation while he does the dishes. She asks personal questions, and they jokingly explore the topic together. Their banter includes playful teasing and a reminder to keep things fun and fa

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