Videos (stepson and friend compete for step mom s attention)

Pristine Edge encourages her stepson, Jimmy, to date her friends on "Dating My Stepson." Surprisingly, her final date is with Jimmy. They start awkward but become playful as Pristine discovers he’s dated her friends. After a heartfelt admission of fe

Bigtit milf Tiffany Madison wants to get knocked up so she manhandles her stepson and his BFF in a BBG threesome

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

Amber Summer competes on Pristine Edge's show for her son Jayden to choose a stepsister. While she showcases her nurturing side, Jayden feels uncertain about their bond. After a playful date at a corn maze, he finds her confidence intriguing but ulti

Bigtit milf Sophia Locke wants a baby so she gets her stepson and his friend to fill that pussy with a double creampie

Oliver Flynn’s video "Three Steps to Impress Your Stepmom" inspired a sequel focused on his stepmom, Eva Long. He captures her attention with playful gestures, builds trust through reassurance, and offers compliments. Their connection grows through m

Olivia Westsun, a devoted ballet student, warmly greets her coach and friend Martin Spell. They enjoy playful banter while practicing, with Martin encouraging Olivia as she demonstrates her skills. Their supportive session fosters camaraderie and ins

Damon Dice is surprised by his stepsister Mackenzie Moss's playful teasing, stemming from a challenge she discussed with a friend. Their light-hearted banter leads to a fun moment on the couch, strengthening their sibling bond, which Mackenzie eagerl

Emily Mayers dresses in a chic little black dress and stylish heels for New Year's Eve, feeling confident for a night out with her boyfriend, Michael Fly. After a toast and an early kiss, they share sweet moments and laughter, creating a romantic atm

Bombshell milf Cassie Del Isla hustles her stepson and his friend with the promise they'll be her boy toys if she wins

Jennifer White helps her stepson, Parker, navigate relationships after overhearing his plans with a girl. She teaches him about body language and communication, emphasizing respect and boundaries. Parker gains confidence and becomes better prepared f

Lush and lusty Bunny Madison takes her daughter’s suitor on a date that turns into a test drive of his nice cock

Crystal Rush teaches her daughter's potential boyfriend how to dance and then how to please a babe in the bedroom

Caitlin Bell and Sonia Sparrow, new stepmoms, embrace friendship while navigating their roles with their stepsons. They share laughter and camaraderie, appreciating each other's kids. A playful cleaning game helps the boys bond, leading to joyful sha

Ivi Rein knows her stepmom Zlata Shine has the hots for her boyfriend but she gets that there’s plenty of him to share

Jimmy Michaels has a crush on Alexis Malone, his friend's attractive mother. Despite her attempts to keep distance, Jimmy seeks opportunities to be with her. An awkward moment arises when he sees her in stylish clothing, leading to flirtatious encoun

Logan Pierce found himself playfully caught in a rivalry between sisters Aria and Jessa over his attention. What began as teasing escalated into a spirited contest of charm, filled with laughter and fun. Ultimately, Logan enjoyed the moments they cre

Laura and her friend Anya are enjoying an illustrated book when Laura's stepson, Lucas, notices but feels embarrassed and leaves. Anya checks on him, leading to a heartwarming conversation. The trio discovers a shared attraction and engages in playfu

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

Sophia Locke, feeling lonely, decides to spice up her life by wearing elegant outfits at home, attracting her stepson Diego Perez. Their playful banter and lighthearted interactions lead them to share quality time, deepening their bond and bringing j