Videos (stepmom gina helps stepson tommy with his urges)

Alana Cruise feels uneasy about her daughter Emily and her stepson Kyle spending time together. Despite Alana's attempts to set boundaries, Emily often leads their interactions, disregarding her mother's concerns. Alana worries about their choices an

Charlie Valentine aims to be a caring stepmother to Juan Loco and decides to bake cookies. During decorating, icing spills occur, leading to a playful mess. Juan shares the funny moment with a friend, prompting Charlie to invite him back for a lighth

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

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

In "Dating My Stepson," men must impress their date's mother first. In this episode, Rebecca and Alex enjoy a fun evening playing pool, leading to flirtation and shared laughter. They express mutual interest, leaving open the possibility of future da

Ryan Keely, recovering from a knee injury, relies on her stepson Nick for daily support. As he assists her with tasks like moving her wheelchair and bathing, their bond deepens. Nick learns to provide care while ensuring Ryan feels comfortable, findi

Sharon White finds her stepson's socks in poor condition while doing laundry, prompting a conversation with Raul Costa. Their encounter becomes awkward, but they discuss the need for clearer boundaries and open communication, enhancing respect in the

Jessica Ryan is excited to listen to a baseball game on the radio while wearing her spirited outfit. Her stepson, Rico, enters, and they share light banter, including a funny mispronunciation. After a playful kiss, he leaves to get ready for his game

Adira Allure is worried about her stepdaughter, Kate Bloom, and her shy relationship with Seth Gamble. To help, she offers friendly advice to improve their communication and affection. As Kate and Seth open up, Adira feels relieved and happy to suppo

Thanksgiving poses challenges for Reagan, her stepson Kyle, and adopted daughter Kiara. As they navigate awkward moments, Reagan encourages gratitude, but Kyle's response creates tension. Despite discomfort, they share appreciation, finding joy and c

Jay Romero unexpectedly encounters his stepmom, Charli Phoenix, in a private moment. She playfully asks him to help retrieve a toy, leading to light-hearted banter and an exploration of boundaries. They share mutual enjoyment and agree to keep the ex

Seth assists his stepmother Claudia and stepsister Kyler with chores, sharing playful banter. They later retreat to the bedroom to explore their feelings but are interrupted by Claudia. Back in the living room, their flirtation intensifies until Clau

Julia discovered a personal item in her stepson Van's room that led to a heartfelt conversation about his relationship struggles with his girlfriend Halle. She chose to support them, facilitating open discussions about intimacy, trust, and comfort, h

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

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

This season on "Dating My Stepson," Kira and her stepson Sam enjoy a fun outing that begins with a scenic boat trip. After an accidental fall into the lake, they share playful moments indoors, strengthening their bond with laughter and flirtation, hi

Jodie Johnson likes bossing her stepson around even more when she realizes how horny it makes him to fuck her

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

Nikki Nutz feels anxious about his date, but his stepmom, Alyssa Reece, encourages him to practice. They role-play compliments and light interactions, with Alyssa offering supportive advice on confidence and communication. By the end, Nikki feels mor