Tori Cummings - Showing Him How To Spoil A Lady - S5:E8
Released: July 17, 2026
Enzo East is going on a date with his stepmom, Tori Cummings. Although Enzo is an outdoorsy guy, Tori has planned a spa day with him. She wants to show him that sometimes it's more about pleasing a woman than about always doing what he wants.
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...
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!
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...
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.
