DatingMyStepson Full Siterip as of May 2025
24 Videos | 50 GB
Dating My Stepson is a taboo porn site set up like a reality television show. One lucky guy goes on dates with his stepmom's friends, and would you believe it, he ends up sleeping with all of them, and even his stepmom to boot!
Cory Chase - An Exercise In Seduction - S5:E7
Released: July 8, 2026
Cory Chase is going on a date with his stepmom, Cory Chase, but he doesn't know it beforehand. He's surprised when Cory is the one who wants to do a workout session with him. This horny milf is divorcing her deadbeat husband and feels like the soon to be former stepson is fair game for her needs.
The date begins with Cory wearing tight fitting clothes as she leads Enzo on a workout to test his stamina. Despite his boner, Enzo does his best. It helps that Cory is constantly putting him into positions that are increasingly sexual. By the time Cory finally stops teasing Enzo, he can't wait to get his tongue on her pussy and eat her out. Getting his dick sucked by his stepmom is one of the best moments of Enzo's life to date...
Sophia Locke - My Stepmom Is The Perfect Date - S5:E4
Released: April 16, 2026
This season on Dating my Stepson, stepmoms are throwing their stepsons a bone by hooking them up with their single friends. Today's milf is Sophia Locke, who is also Arin Jones's stepmom. She just doesn't think any of her friends are going to love Arin the way she thinks he deserves.
Sophia has put together Arin's perfect date, a floor picnic with all of his favorite foods and a jacket for his favorite team. Sophia goes to change into a slutty cheerleader costume that makes it clear she's going to go all the way with him. Kneeling behind Arin, Sophia massages his shoulders. Then she kneels in Arin's lap and pops her big tits out right in front of his face. Arin is putty in Sophia's hands as she gets on her knees beside him to suck his dick...
Diana Grace - She Wants Coffee And My Cream - S5:E3
Released: April 1, 2026
This season on Dating my Stepson, stepmoms are throwing their stepsons a bone by hooking them up with their single friends. Today's milf is Diana Grace, who is BFFs with Gunnar Bishop's stepmom. They're going to have a coffee date where they try different coffees and creams. Both are excited to see where the day leads.
The coffee tasting isn't Gunnar's cup of tea, but he perseveres the best he can. When he's served a coffee with ghost pepper in it, Gunnar overheats and peels his shirt off. Diana is happy to match him, popping her boobs out of her dress. From there, it's easy to coax Gunnar into eating her pussy and then showing her what he's got down under. Diana can't wait to get her mouth around that nice cock for a good BJ. Gunnar shows his strength by lifting Diana up and holding her upside down so they can have a vertical 69.
Talia Mint - Show Me That Youre Good Enough - S5:E4
Released: February 10, 2026
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 Talia Mint, who has planned a massage to see how potential date Sam Bourne looks without all those clothes in the way.
At first, everything is on the level as Talia uses a towel to protect Sam's modesty during his massage. Things get hotter as Sam's boner becomes evident while he's on his back. Talia reaches down to cup it, then ditches the towel and goes full vixen on him. Next thing Sam knows, his potential date's mom is naked and massaging his dick...
Sharon White - I Have To Have Her - S3:E5
Released: January 6, 2026
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 Sharon White, who is newly divorced. She's allegedly looking for someone for her daughter, but if she finds a dude for herself she's not going to argue.
Sharon's date today is Sam Bourne, who Sharon immediately thinks is nice, young, and definitely her type. The date itself is going to be Sam teaching Sharon some English. Sam is confused, but Sharon knows this will give her excuses to touch Sam and have him touch her. Their lessons get hands on when Sharon asks Sam to touch her boobs. A hot minute later, Sharon is kissing him and then sucking Sam's dick...
Shalina Devine - I Didnt See This Cumming
Released: October 15, 2025
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 Shalina Devine, who could not be hotter or hornier. She's ready to take on Nikki Nutz, who's been looking for love.
Silvia Saige - Country Milf Is Too Much To Handle - S1:E6
Released: May 29, 2025
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 Silvia Saige, mom to Lilly Mae. A southern country belle, she needs to know if Sage Roux can handle her and her daughter.
Millie Morgan - Her Moms Traditional Technique - S4:E10
Released: January 29, 2025
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 Millie Morgan, mom to Sarah. She has set up a date where she gives Parker a palm reading followed by a nice massage out in her backyard.
Bunny Madison - Showing Her Mom My Best Moves - S4:E9
Released: January 17, 2025
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 Bunny Madison, mom to Becky. Bunny has prepared a floor picnic as a date with Parker Ambrose. They begin chatting, and the chemistry between them definitely sparks.
Cherry Kiss - Her Mom Took Me For A Test Drive - S4:E8
Released: January 8, 2025
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 Cherry Kiss, mom to Lindsay. Parker Ambrose, the potential suitor, is a bit confused about the show’s premise, but he’s game since the normal dating scene isn’t working out...
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...
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.
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...
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...
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.
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.
Micky Muffin - Coming Clean - S1:E4
Released: March 29, 2024
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 having a picnic with her stepson Sam Bourne. They both confess to the cameras that the week in the house has changed their opinions of each other. They initially agree to go with the flow and not make things awkward, but they get flirty together with the fancy food and find themselves coming together for a deep kiss.
Kira Queen - All In - S1:E3
Released: March 20, 2024
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's episode, Kira Queen must face off with her stepson, Matthew Meier. They are to enjoy a casino night together, even though they can't seem to stop telling each other how much they hate one another. Matthew doesn't take it well when Kira beats him, and she slaps him to stop him from continuing to yell. The next moment, the two of them are making out...
Shalina Devine - Candlelit Romance - S3:E2
Released: March 7, 2024
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's episode, Alex Charger and Shalina Devine are enjoying a candlelit dinner date. It's a bit awkward for the stepmom and stepson to be dining romantically, but they have both been into each other for a long time. Shalina tries to deny the chemistry between them, but she can't keep slapping Alex away...
Micky Muffin & Shalina Devine - Pleasure By The Pool - S2:E5
Released: February 16, 2024
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's episode, Shalina Devine is supposed to have a date with Matthew Meier. Unfortunately for Shalina, Micky Muffin has other plans. She likes Matthew far too much to let him go easily.
Micky Muffin - It Started In The Jacuzzi - S2:E4
Released: February 7, 2024
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 in the series. This time, she and Matthew Meier are getting to know each other in a jacuzzi. There's nothing stopping them from feeling each other up and eventually coming in to make out...
Micky Muffin - I Aced Her Hole - S2:E3
Released: January 25, 2024
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 going on a date with Alex Charger. They're going golfing, although Micky doesn’t know anything about it...
Kira Queen - Going Overboard On Her Pussy - S2:E2
Released: January 12, 2024
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's episode, Kira Queen is paired up with Sam Bourne. Kira still lives with her stepson, so she's on the show to find a boy toy for herself. Their date is to go on a boat with Sam manning the oars to take them around a nearby lake. When Kira has had enough, Sam brings them back to the dock so they can move the party indoors.
Kira Queen - Massage Queen - S2:E1
Released: January 3, 2024
This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's episode, Russian widow Kira Queen meets up with her date Alex Charger for a massage date. Kira is eager to learn more about this outgoing and handsome young man, so she comes up with a plan before ever laying down on the massage table...
Pristine Edge - Stepmoms Secret Confession - S1:E5
Released: September 28, 2023
Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Jimmy learns that his final date is Pristine herself. Pristine isn't happy about the producers putting her in this situation, but she and Jimmy decide to make the best of it. They agree to sit down to the very nice dinner that's been laid out for them, and soon enough things have moved from awkward to flirty...
Crystal Clark - Riding More Than Bicycles - S1:E4
Released: September 27, 2023
Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Crystal Clark is in it to win it. She's already into younger guys, so Jimmy is right up her alley. She can't wait to drain Jimmy's balls as she fucks him right...
Cassie Del Isla - Turning Up The Heat - S1:E2
Released: September 26, 2023
Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Cassie Del Isla will be cooking dinner with Jimmy. Normally Cassie dates older men, but she is making an exception to see how things are with Jimmy. They work together to make a pizza, where Cassie gets increasingly flirty...
Bunny Madison - The Milf Youd Want To Marry - S1:E2
Released: September 25, 2023
Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Bunny Madison is ready for her date with Jimmy. A college friend of Pristine's, Bunny can't wait to see what Jimmy has to offer as a romantic partner.
