Videos (stepmom ivy ireland gives stepson a special helping hand)

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

During Christmas, Jay and his stepsister Alicia decorate the tree and are encouraged by their mother, Crimson, to make gingerbread houses together. Their neighbor, Celestina, joins in the festive fun, fostering laughter and creativity while they cher

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

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

Andi Avalon takes exception to her stepson calling her boring so she role plays the last time she cheated with his dick

Crystal Clark and Demi Diveena enjoy quality time while Crystal's stepson, Jay, plays video games. They playfully tease Jay, leading to lighthearted banter. As the evening unfolds, Demi becomes intrigued by Jay, enhancing their friendly and fun atmos

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

Melanie Hicks embraces her new life after remarriage and develops a playful bond with her stepson, Eddie. They share a fun day outside, applying suntan lotion and teasing one another. Through laughter and storytelling, they strengthen their family ti

Payton Preslee is devastated by her husband's infidelity, including betrayal by her sister. While caring for her stepson Charlie, she feels angry and plots her next moves. Together, they embark on an unexpected journey, exploring trust, loyalty, and

Alex Mack is adjusting to life with his young stepmother, Skylar Snow, with whom he feels a strong attraction. Their relationship becomes complicated as affection grows, leading to intimate moments that challenge family boundaries, prompting them to

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

Tiff and her boyfriend Van decide to film a playful video but unexpectedly encounter Van's stepmom, Janet, who offers filming tips. Janet encourages Tiff to explore her skills, fostering a supportive atmosphere. The trio navigates intimacy and connec

Ashley Lane reconnects with her friend Jamie Michelle, who is now married and has a stepson, Ricky. During a catch-up, Ricky's curiosity about their relationship grows when he accidentally overhears them. The story explores their evolving friendship

Armani Black, preparing to meet her fiancé's parents, initially chooses a bold dress but changes to a chic top and miniskirt after her stepson Jimmy suggests it may not suit his grandmother's taste. They share a warm connection while sharing chores a

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

Katie invites her stepbrother Nick to observe her playful time with her boyfriend, Joshua. After a lighthearted start discussing chores, she surprises Joshua by blindfolding him. The scene is filled with excitement and spontaneity, showcasing their c

Jayrock is startled to find his stepmother, Kayla Paige, on his computer. As he nervously asks her to close it, she notices the content and suggests it's just pop-ups. Their conversation shifts playfully, exploring their relationship boundaries and i

In "Dating my Stepson," young men seek love by connecting with potential girlfriends' mothers first. This episode features Bunny Madison and Parker Ambrose enjoying a picnic and games, highlighting their chemistry and playful interactions, sparking c

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

In "Dating My Stepson," suitors must impress their girlfriend's mom first. In this episode, Shalina tests Alex with a truth or dare game, revealing his relationship history and dietary choices. They enjoy playful moments, but will it lead to romance?