Stella Bliss - My Mom's Best Girlfriend! You Can Fuck My Ass, but Do It Quietly so Your Mom Doesn't Notice Us!
Released: November 22, 2024
Devil Khloee - My Latina Mother-In-Law Baked Me a Hot Surprise
Released: November 21, 2024
I’ve heard that no one is more welcoming than a Latina mom, but I wasn’t expecting my mother-in-law to be that… nice. She called me to arrange a surprise for my girlfriend, so I went to the supermarket and got everything to bake a cake with her mom. The second I got to my mother-in-law’s house, I noticed she was all over me. She was wearing a tight dress that was making all her curves and thick ass look better than ever. She knew how hot she looked and was using that to get close to me, rubbing my arms and my legs and grazing her big boobs anytime she noticed I was looking. I tried to stop her, I swear I did, but what did you expect me to do when she shoved my dick in her mouth and started sucking me dry? I’m just a guy, and she is a total MILF. There was no way I was passing on the opportunity of pounding this babe after she got me so fucking horny and acted like a slut. I’m telling you, Latina moms are the best.
Texas Patti - There Is No Resisting Her Mom - S5:E2
Released: November 20, 2024
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's milf is Texas Patti. Alex Charger is back once again, looking for love in the form of his potential girlfriend’s mom. Patti wants her daughter to meet a guy who’s kinky like her. The date Texas has prepared is a game of Would You Rather that will let her get to know Alex better...
Skylar Snow - The Motherfucker
Released: November 15, 2024
Busty stepmom Skylar Snow is sure that her stepson is completely innocent. What else can be expected from a guy who spends 24 hours playing video games? Like any decent stepmother, Skylar worries that the young man does not have a girlfriend, so she sometimes listens to conversations in his room in the hope of hearing a woman's voice there. However, today a woman became a casual witness to an unusual conversation.
Veronica Leal - Manifesting A Great Fuck - S5:E1
Released: November 1, 2024
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's milf is Veronica Leal dating Alex Charger. Veronica is a super fit fun mom, who is ready to test Alex to make sure he'll be the perfect fit for her daughter.
Rebecca Volpetti - Dropping My Balls In Her Moms Pocket - S4:E5
Released: October 18, 2024
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's date is Rebecca Volpetti. The date is Alex Charger. Rebecca has prepared a date in her game room where they will play pool. They take shots as they chat, but Rebecca realizes she likes Alex so much that she needs to seduce him.
Cory Chase - Massaged And Milked By Anal MILF
Released: October 17, 2024
After facing some anal rejection from his girlfriend, Alex Jones finds himself lured onto a milking table by his girlfriend's horny masseuse mom (Cory Chase). Cory milks Alex 'til he cums, then lets him fuck her ass. It may be a matter of time before they're caught, but they're going to make the best of it with some hot, pervy sex.
Jennifer White - Guidance & Training
Released: October 5, 2024
I talked to your girlfriend.. Honey, I’m fine with you having sex… But you shouldn’t pressure her to do anal. She’s not ready yet. Trust your step mom. I know you really want to try it. But your girlfriend needs to want to try it too.. I don’t know why you’re so obsessed with anal. Have you even done it before?..
Shalina Devine - A Game Of Dare Always Spices Things Up - S4:E4
Released: October 3, 2024
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's date is Shalina Devine, mom to Amirah. The date is Alex Charger. Shalina wants to make sure Alex chooses Amirah, so she sets him up to play a game of truth or dare...
Rachael Cavalli - Heartburn pt. 1
Kenzie Taylor - When Dad Is Away II
Penny Barber - Behind Dad's Back
Aubree Valentine - Challenge or Fail
Brooke Barclays - Playing in the Pocket
Dana Vespoli - Dear Annie
Cherry Kiss - We're a Team
Mina Luxx - Private Dick
In Part 1 of the "Heartburn" saga, we're introduced to several of the characters, after a brief tease of the sexual action (and infidelity) in store.
Rachel (Olive Glass) is a housewife who is going back to college to study and become a professor, while earning some money of her own tutoring. Her husband George (Ryan Driller) is somewhat stifling to her ambition, sending her off on an errand to get his car fixed, even though she's busy trying to write. They're planning a weekend getaway but the busted car is one roadblock...
Sadie Summers - Best Birthday Ever
Released: June 6, 2024
19 year old Matt (Jimmy Michaels) feels down in the dumps because his stepmother (Sadie Summers) has forgotten all about his birthday.
Bella Bare - 53-year-old Bella Bare is down to fuck her daughter's boyfriend
Released: July 25, 2024
Jimmy comes by looking for his girlfriend. She's not home, but her hot mom, Bella Bare, is, and she's wearing a sexy red dress. Her daughter isn't going to be home for a while, but Bella invites Jimmy to stay. She has a few things she wants him to take a look at. One of those things is her pussy.
Sure, the guy, who looks like he can't be more than 18 years old, is shocked when Mrs. Bare, who's 53, grabs his ass, and, sure, his girlfriend would freak if she found out about this, but that's a risk you have to take when a petite piece of ass like Bella starts making the moves on you. Besides, there's no way Jimmy's girlfriend can suck and fuck the way her mother does.
Megan Marx - Happy Hump Day - S27:E1
Released: July 17, 2024
Megan Marx spies her stepbro Nick Stokes coming home from school. She tells him happy hump day and gives him a hug, leaving Nick confused. Later, Megan tells Nick happy hump day yet again and shares that she heard his girlfriend talking about how big his dick is. It may not be Wednesday, but it's the day Megan has decided to hump him. They're interrupted by Megan's mom arriving home...
Natasha Nice - My Girlfriend's Mom Is Just Like Me!
Released: July 15, 2024
Alex Jones has always had weird chemistry with his girlfriend, who's too bossy and selfish in bed. When he meets the GF's mother (sexy Natasha Nice) one evening, the two hit it off immediately! Alex just has so much more in common with the sweet MILF. One thing leads to another and an innocent introduction turns into passionate fucking in the kitchen... but will Natasha's daughter catch on?
Anya Olsen & Ashley Alexander - Meet The Step Mom
Released: June 26, 2024
Oh my goodness! A hot hot young girl? Is this your girlfriend, Alex? That’s amazing! I’m Alex’s step mom.. I don’t think he’s ever had a girl over before. And you’re so pretty… Well, I won’t bother you too much. I’m sure you’re ready for some action, if you know what I mean….
***Starring Anya Olsen & Ashley Alexander***
Ebony Mystique - Black queen Ebony Mystique loves to educate her son's friends on how to fuck a woman
Released: June 10, 2024
Kevin and his girlfriend want to hook up Max with a girl today at the mall, Max doesn't want to go because he's a virgin and has no experience with girls. Kevin's mom Ebony Mystique, arrives home and asked why wasn't he at the mall with her son. Max told her that he doesn't know how to treat a woman, and since the house is empty, and they're all alone she can undress him and show Max how to fuck a woman.
Brooke Barclays - Watching Porn With Brooke
Bunny Madison - The Game
Ophelia Kaan - I'm Yours, Son
Ricky (Spanish) is very close with his stepmom Brooke (Barclays), and he sympathizes with her over the news that dad is staying longer in Europe on business, rather than returning to take Brooke on vacation. It's her birthday coming up, and Ricky presents her with a computer tablet he owned, wrapped up with a bow (he couldn't afford a new one)...
Cassie Del Isla - Putting In The Effort - S4:E2
Released: May 29, 2024
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's date is Juan Loco trying to impress Cassie Del Isla, mom to Tiffany.
Cassie has prepared a date where Juan will learn how to treat a lady. She shows him how to arrange roses, how to make chocolate dipped strawberries, and how to write a haiku. Cassie can tell Juan is checking her out, and she finds that she likes it. By the time they get to the haiku, they can't seem to keep their mouths off each other...
Kaya Knight - Extensive Stamina Training
Released: May 22, 2024
Kaya is concerned about her stepson, Rion. She’s fed up with him lazing around the house, and she wants a stepson she can finally be proud of. Ever since Rion and his ex-girlfriend broke up, he’s been a slob and doesn’t want to do anything. Rion reveals he has a bit of a problem regarding stamina. He cums far too early, and he feels it’s the reason for his breakup. Kaya won’t take that as an excuse - if he needs help lasting longer, she’ll get him there. Rion is stunned when Kaya offers to play with his cock. He knows he shouldn’t be getting sex lessons from his stepmom, but when she grasps his dick, it’s hard to resist. She pumps his cock and sees what he’s working with. Rion is good at fucking, but she wants to get him to last longer. The sweet milf does everything in her power to help Rion and his stamina. From there on out, Rion and Kaya mess around whenever they can. She knows getting him to last longer will take work, but the strict Tiger Mom is seeing results immediately. Finally, Rion can fuck without cumming too quickly, and he pounds his stepmom hard, filling up her pussy with every inch of his shaft.
Crystal Rush - Learning Some New Moves - S4:E1
Released: May 16, 2024
This season on Dating my Stepson, we're taking a new twist. The guys are looking for love, but they need to date the potential girlfriend's mom first. If it works out, he'll date the daughter right on the spot. Today's date is Rion King trying to impress Crystal Rush, mom to McKenzie.
Kiki Klout - Dad's spoiled girlfriend, Kiki Klout, receives a thick bar of white chocolate with nuts for Mother's Day
Released: May 11, 2024
It's Mother's day and Ethan's dad insisted he get Kiki Klout something nice for the special occasion. But Ethan could care less since Kiki is not his mom. But when Kiki threatens to tell Ethan's dad that he wasn't very thoughtful and that his allowance should be better off with her, Ethan acts quick to please her. He comes back with her favorite treat -- a big thick bar of white chocolate with nuts!
Pristine Edge - Playing My Cards Right - S1:E3
Released: May 3, 2024
This season on Dating my Stepson, Jayden Marcos is taking a new spin towards finding love. She has decided to go on a date with the potential girlfriend's mom. If it works out, he'll date the daughter right on the spot. Today's date is with Pristine Edge, mom to Rachel.
Mandi Mayes - 48, teaches a young guy the art of ass-fucking
Released: April 18, 2024
Ace has come to Mandi Mayes for advice. You see, his girlfriend wants to get fucked in the ass, but he doesn't know how to go about it. "Lube up her ass and stick it in her butthole," you might say? "Anal sex is amazing," is what Mandi says. "I can show you how to do that."
By showing, she means doing, and that's what this scene is all about: 48-year-old mom and wife Mandi taking a big cock up her ass. But here's the problem for Ace: Now that he's ass-fucked the best, will he even want his girlfriend, or will he keep coming back to Mandi for some mature ass?
Romi Rain - Out Of Your System
Released: March 21, 2024
When it comes to beautiful women, the eye does not betray one's interest and admiration. You spend time scrolling through your phone while waiting for your girlfriend to arrive when the door to the house opens, and Romi Rain, your girlfriend's mother, walks in. The busty MILF chats you up, making small talk before bringing up a sensitive topic. Romi notices how your attention seems to wander whenever she's in the room and wants to clear the air between the two of you.
UPDATED Christy Love - Is There a Doctor in the House?
Released: April 10, 2024
Christy is not a fan of her stepson’s life choices. If Christy had it her way, Max would be a doctor and would take care of her for the rest of his life. But Max is distracted by his girlfriend, and Christy believes the chick has filled Max’s head with dreams and nonsense. Not to worry, though. Christy is the type of Asian mom who knows how to use discipline as well as rewards to get someone back in line. The Tiger Mom tells Max she can do whatever his girlfriend can do and more. She gets down on her knees and starts blowing her stepson. Max knows this whole situation is fucked up, but the way his stepmom sucks his cock is like nothing he’s ever experienced before. She knows how to use her tongue so delicately, and her lips wrap around his cock as though she’s been practicing for this moment forever. When Max is about to cum, Christy stops and won’t let Max cum until he comes home with better grades...
OwlCrystal - Just a Slut?
Released: February 6, 2024
Carassio is lucky to have OwlCrystal, a hot vixen with an everlasting sex appetite, as his girlfriend. His mom, however, begs to differ: she thinks that the horny girl is wrecking his life, having sex with him all the time instead of letting him focus on other stuff. The problem is that Carassio’s bitchy mom has bad timing: she just called her son to tell her this in the middle of a blowjob! Now that OwlCrystal has learned what her “mother-in-law” thinks about her, she will get her revenge. There’s only so much that she can do with Carassio’s huge dick, and she doesn’t mind adding some extra sex toys to pervert the not-so-naive Carassio. Maybe his mom will learn his lesson when she gets to see the filthy videos the two shot, having sex all over the house with all kinds of toys and positions that Carassio’s prude mother hasn’t even heard of.
Cory Chase - Cumming Home for Christmas
Released: December 16, 2023
Alone with Step-Mom
I'm home for Christmas and I (Luke Longly) can't wait to see my dad and my step-mom! I ring the doorbell and my step-mom, Cory Chase, answers the door wearing a bright red dress. I walk inside and we sit down next to each other on the white, leather couch. She starts asking me questions about my ex-girlfriend at college, when I notice my step-mom's legs are starting to spread. 'You're not wearing any panties!' I gasp. I grab her leg and help her legs spread wide open. Then, I notice that she is bald down there! She doesn't have a bush! And I suddenly notice that she isn't wearing a bra either! My step-mom unbuckled my belt, telling me that she wants to unwrap her present now...
Emma Rosie & Nikki Rouge - Sharing with Boyfriend’s Mom
Released: May 6, 2023
Cheating is complicated, but it can turn into something more complex, like what happened to Emma Rosie. The beautiful tiny blonde cheats with Milan while her boyfriend is not at home. The two horny beasts are already at it on the couch. Milan gives the skinny tattooed hottie the foot worship she deserves. Emma and Milan are so busy with their dirty deeds that they don't notice Nikki Rouge coming to the living room. The surprised look on Emma's face becomes more apparent when her boyfriend's mother reveals that Milan has his way with her this morning...
Sladyen Skaya - My Girlfriend Catches Her Mom Sucking My Cock And Takes Over
Released: November 12, 2023
Justine Jakobs - The Secret Girlfriend
Released: November 15, 2023
You’re at home waiting for your girlfriend to come over. Her mom walks in the door. Your confused because she’s all alone. She says there’s something she needs to tell you about her daughter…
Madi Collins - Good Girl From Now On
Released: August 21, 2023
Just as Derrick is about to read her the riot act, a car horn sounds and Madi rushes off with her boyfriend Joey, escaping the impending lecture. But when she returns, Madi is distraught: Joey was mean to her. Surprisingly, stepdad takes her side: he's glad she's dating, after all he was dating at even a younger age, but he wants to back up her mother as his wife, in charge of her own kid.
Elizabeth Skylar - Sexy MILF Elizabeth Skylar shows her son's friend how she handles a cock
Released: October 10, 2023
Ricky stops by his friend's place to hang out but his friend is out with his girlfriend. His friend's mom, Elizabeth Skylar, is home and insists Ricky stay to enjoy some cookies and talk with her. When she finds out Ricky is single and doesn't know how to approach a woman nor what to do with one, she takes her big titties out and teaches him a lesson on how to fuck.
Brianna Beach - Take It Slow
Released: July 5, 2023
I’m sorry your girlfriend broke up with you. Do you want to talk about it?.. I’m your step mom, you can tell me anything.. Even if it’s embarrassing. It’s my job to help you, and maybe I can teach you something new…
Cc Doll & Lolly Dames - Relationship Advice
Released: June 8, 2023
We need to talk. Why are you not willing to experiment with your girlfriend? You know she’s going to break up with you. As your step mom I can’t allow you to ruin this relationship. She wants to try anal. There’s nothing to be scared of.. Don’t worry, I’ll stay here and help both of you…
Gigi Dior - Hot, blonde MILF Gigi Dior fucks her daughter's boyfriend
Released: April 21, 2023
Ah, it's the always exciting daughter-leaves-her-cell-phone-home-and-mom-sees-the-dick-pic-she-received-from-her-boyfriend scenario. In this case, the daughter is only 18 years old, the guy sending the dick pic is 34 and the mom is Gigi Dior, a 41-year-old blonde hottie. Now, in most cases, this would spell trouble for the boyfriend, but not here. Gigi likes what she sees. Check that. She loves what she sees. She wants some of what her daughter's been getting. So she texts him back as if she were her daughter, and when the dude arrives, he's shocked to see his girlfriend's mom standing at the door wearing sexy lingerie...
Eden West - Before She Wakes Up
Released: April 10, 2023
You wake up next to your beautiful new wife, who looks a little tired. Being a mom can be a tough job, and she wants to have a little fun.. But you have to do it quietly...
Brianna Beach & Krissy Knight - Our Girlfriend
Released: March 30, 2023
Sit down. And get rid of that attitude. You shouldn’t be surprised. Your girlfriend is very sexual and needs new experiences, and you haven’t been willing to help her. But don’t worry, step mom has done your job for you. She’s our girlfriend now…
Scarlett Sage - Bro's Big Problem
Released: January 18, 2023
Katie (Scarlett Sage) is in her blue gown getting ready to go to her school graduation ceremony, putting on lip gloss, then calling out to her stepbrother Johnny (Joshua Lewis), afraid they'll be late for the big event. With no answer she searches for the boy, finding he's hiding in the bathroom.
She finally coaxes him to open the door and let her in, Johnny reveals his secret: his cock is standing up pointing skyward in his underpants, looking like a tent pole. Katie finds his predicament a riot, her laughter only adding to his humiliation. Making matters worse, he's class valedictorian, but ashamed to appear in public in this embarrassing condition. And when he confesses that the sustained boner was caused by his having taken some of her daddy's potency pills, the situation sounds even worse...
Bunny Madison - Banging My Girlfriends Mom - S17:E11
Released: February 24, 2023
Alex Mack is waiting for his girlfriend Jessie to come home from work. His girlfriend's mom, Bunny Madison, takes Alex through a photo album of old pics. Then she begins to talk about how she's had to beat off lots of men.
