Videos (stepmom teaches stepson how to take a proper dick pic)

Stepmilf Armani Black offers to show Mandy Waters how she lets her stepson cum inside her to save money on tissues

Cherry and Katrina enjoy coffee while their stepsons, Parker and Juan, excitedly discuss a golf tournament. The stepmoms change into nicer outfits, receive compliments, and invite the boys to join them for some lighthearted banter. They share laughte

Karina King is secretly chatting online, which her stepson Alex accidentally discovers. Their brief but intense conversation leads to emotional upheaval and unexpected feelings between them. As they navigate their complicated bond, they confront fami

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

Jamie Michelle enjoys her new role as a stepmom to sweet Alex, her stepson. While baking cookies with friend Maya, they catch Alex sneaking peeks. When he becomes impatient and gets stuck in the cookie jar, the trio shares laughs and playful moments,

Two stepmoms, Lauren and Skylar, accompany their stepsons, Robby and Juan, to a crafting event. Frustrated by delays, they humorously switch roles to motivate the boys. Their playful approach helps refocus the kids, leading to laughter and plans for

Mandy Waters relaxes on the couch when her stepson Johnny returns from college, feeling stressed about a math exam. To help him unwind, she suggests joining her for a shower, fostering a lighthearted conversation that strengthens their bond and empha

Valentina Bellucci calls her stepson Chris Lockwood to assist with a plumbing issue. After fixing it, Valentina invites him to stay, leading to playful and complicated interactions that leave Chris feeling uncertain yet intrigued. The encounter creat

Sandy Love aims to be a caring stepmom to Parker Ambrose, supporting him with his favorite pizza and offering comfort when he can't spend time with his dad. She engages playfully, creating a loving atmosphere that fosters their special family bond.

Sadie Ambrose prepares for a night out, applying moisturizer and dressing up. Her stepson, Parker, offers to help with her zipper and playfully inquires about her plans. Their interaction leads to humorous misunderstandings, highlighting family dynam

Pristine Edge sets up dates for her stepson, Jimmy, to help him find romance. On his first date with Sarah, they enjoy a couple's massage. Initially nervous, Jimmy’s awkwardness leads to a playful moment when Sarah joins him on the table, making the

Jennifer White is a stepmom now. Since Mother's Day is coming up, she begins making a list of things she wants from her stepson Jimmy Michaels.

Gina, focused on fitness, invites her stepson Raul to join her for stretching after an unexpected visit. Their playful interaction reveals underlying tension, shifting to a more intimate exchange that emphasizes consent and communication, deepening t

Pristine Edge and Sophia Locke return from shopping to find their stepsons, Jimmy and Juan, engrossed in video games. Teasing the boys about their gaming habits, they change into tennis outfits, leading to a fun, lighthearted game. The women provide

Crystal Rush is working when her stepson Jayden asks for an allowance advance for dates. She advises him to seek someone with shared interests for deeper connections. Later, their discussion emphasizes the importance of mutual respect and building me

Beverly Hillson, a busy massage therapist, vents her frustrations to her stepson Jason, who responds with playful sarcasm. After he cleans the house as a reward, he offers her a massage to help her relax. They share laughter and a close bond, enjoyin

Ricky and Juan are excited for their school's Valentine's Day dance, with their stepmoms, Fiona and Cherry, helping them prepare. The women plan to enjoy their own evening after dropping off the boys, ensuring they feel confident and ready for a fun

In this episode of "Dating My Stepson," moms and sons bond while preparing dinner. Sam surprises Shalina with a rose, sparking chemistry. Lighthearted antics, including a playful water splash, create laughter and connection as they enjoy a delightful

Aiden Ashley and Pristine Edge use Easter as an excuse to dress in lingerie to teach their stepsons how to fuck properly

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