Juan Loco is looking to choose a new stepsister, but first he gets to go through the potential newcomer’s room and see what she’s all about. His potential stepsister, Liz…
Madison Wilde sets up a video camera and shows herself off in front of it. She’s waiting for her stepbrother, Jimmy Michaels, to join her so she can see what…
Jay Romero is looking to choose a new stepsister, but first he gets to go through the potential newcomer’s room and see what she’s all about. His first contestant is…
Rissa May loves to play in the snow, but she isn’t having fun without her stepbrother Rion King paying attention to her. She dresses up in her best snow bunny…
Lana Smalls is excited for costume day this year. She has a surprise planned for her stepbrother, Parker Ambrose. Dressed as a slutty version of a space character, she makes…
Dylan Moore and Theodora Day are busy going through neckties when Coal Daniels walks in on them. He asks what they’re doing and Dylan says since her mom is gone…
Ashley Alexander is doing dishes when her stepbrother Juan Loco joins her in the kitchen. Ashley realizes this is an opportunity to get naughty and act out a fantasy. She…
Parker Ambrose gets to decide his new stepsister from two candidates: Jade Maris and Scarlett Alexis. They begin the date with Jade calling the first shots and ultimately getting the…
Bianca Bangs is obsessed with big dicks. Any time she has the chance to imagine a big one, she does. When she’s building a model snowman, she tries to put…
Bianca Bangs and Madison Wilde are working on boxing as a form of self defense and also because there’s a fight coming up that they’re very passionate about. When Parker…
Madison Wilde is dressed like a sexy American ballerina when she struts in to where Ricky Spanish is decorating for Independence Day. She asks Ricky if her skirt is too…
Alex Coal is back to host another episode of her Love Your Family Line. Today’s caller is Victor Ray, whose stepsister Sera Ryder is acting crazy jealous. Sera hates the…
Trinity Olsen and her boyfriend Diego Perez are getting flirty on the couch when Diego’s stepmom Alexis Malone joins them. Diego grows increasingly embarrassed as Trinity and Alexis begin gossiping…
Ethan Seeks and Xxlayna Marie are so excited about the house their parents have rented for a stepfamily vacation. They’re excited right up until they realize the room they’re supposed…
Myra Moans has a sexy new outfit that she can’t wait to show her long distance boyfriend. Between the sexy little top and the miniskirt, it’s clear she’s not wearing…
A crime has been committed at a party of the most notable and notorious people in high society, and it’s up to Detective Perron (Danny D) to get to the…
Robby is over at his girlfriend Bailey’s house as they prepare to study for their college midterm exams. Reagan, Bailey’s stepmom, really wants her stepdaughter to focus on her studies…
If Nicole Kitt thinks she can bring her boyfriend home and have PDA all over her new stepmom Misty Stone’s house, she’s got another think coming! After getting a talking…
Nade wanted to watch a movie with his stepsister, Kelsey Kane. However, she had other plans. She wanted to work out before watching so that she could sit down and…
Johnny was trying to make a documentary for his upcoming rap album. However, his stepmom, Kaden Kole kept interrupting. She even eventually kicked out his friend that was filming the…
Rocket and Ace are spending their day playing video games, but Rocket’s step sister Ashlyn has other plans for him. She barges into his room big ass tits practically bursting…
Savanah comes home to find her step son Jodie fapping away like it’s no tomorrow. She has lost count on how many times she has caught him. His father won’t…
Beautiful MILF Athena Anderson is getting ready to surprise her husband for their anniversary. And anal sex seems to be the perfect surprise in her opinion. The only problem is…
Stepsiblings Penelope and Austin are constantly playing tricks on one another, trying to one-up each other and make the other tap out. They’re both ruthless and love seeing the other…
Parker Ambrose and Jimmy Michaels have gotten together to watch Game 6 of the series as they cheer for opposite teams. Jimmy’s stepmom, Whitney Oc, comes to bring them snacks…
Kiki is always playing pranks on her younger stepbrother, Johnny. Whenever she has the chance, she bullies him and uses her status as the older stepsis to jerk him around….
Joshua’s bedroom got turned into his dad’s new office, so the boy is now forced to share a room with his stepsister, Vanessa. Neither of them is happy about it,…
Porno Dan and his stepson have given submissive Miss Jackson the hardest and roughest sex of her life much to her delight. This dirty talking blonde with a fat ass…
Syren De Mer never thought that it would be so hard for her to get pregnant. Unable to hold back her tears, an upset MILF cries, holding a negative pregnancy…
Stepsisters Chanel and Hazel may not be actual twins, but they look enough alike that they can typically fool people. Their entire lives, they’ve been able to bait and switch…
River and Chloe have been friends for a long time and confide all their secrets in one another. River tells Chloe that she thinks she’s finally ready to lose her…
Bunny is chilling at her place when her friend Talyor shows up at her door. The beautiful babe is crushed because she just learned that her husband is cheating on…
It’s Valentine’s Day, and Elias and Rico are again left without Valentine’s sweethearts. These nerdy dudes are never going to get laid if they don’t start making an active effort…
Jay’s birthday is coming up, and Sydney is doing everything at hand to be the coolest stepmom about it. She wants to throw a big party for him and she…
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today’s episode, Micky Muffin is up for her second date…
It’s Valentine’s Day, and Addis couldn’t be more excited. She has vivid ambitions for this day and imagines her wildest dreams will come to fruition. She fantasizes with Fiona about…
Nina is a fresh slate regarding American festivities, so she is perplexed when her stepson Victor explains Mardi Gras and the significance of the beads. Still, she is highly interested,…
Justine overhears her stepson Kai crying in his bedroom. The guy is crushed because his girlfriend Selina just broke up with him close to Valentine’s Day. Her vivacious stepmom won’t…
