See more by tags DatingMyStepson Diana Grace

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.

Climbing into Gunnar's lap, Diana rides him in cowgirl. Then she lets Gunner push her to her knees so he can do a solid dicking down from behind. Diana enjoys another ride, this time in reverse cowgirl. Then she lets Gunnar bend her nearly in half as he lifts one of her ankles to hook around his neck and open Diana up. Diana finishes Gunnar off by taking his cum shot in her mouth, but it's not enough for Gunnar to want a relationship.

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See more by tags DatingMyStepson Talia Mint

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...

Climbing on top of Sam, Talia sinks down on that fine man meat to ride him right in the living room. Then she sucks her own juices from his hardon while in a 69 where she sees how Sam is with his mouth. Talia goes for a reverse cowgirl ride next, then takes things down a notch as she and Sam fuck while spooning. When Talia gets on her knees, Sam is there to do her in doggy. As they wind down in missionary, Talia realizes that Sam is more her speed than her daughter's.

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See more by tags DatingMyStepson Sharon White

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...

There's no language barrier as things get hardcore. After worshipping Sharon's boobs and ass with his mouth and hands, Sam shoves it in in doggy. Then he fucks Sharon as he spoons behind her. When Sharon takes control, she rides her new lover in reverse cowgirl and then cowgirl. Their fuck fest culminates with Sam going to town in Sharon's cooch until she's squirming beneath him. Pulling out, he lets the milf guide his cum shot all over her trimmed snatch.

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See more by tags DatingMyStepson Shalina Devine

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.

Shalina has decided to play a game with Nikki that breaks the rules of the show, but that's fine because she loves to date younger guys. Blindfolded, Nikki is supposed to guess what Shalina puts in his hand. She's quick to drop her top so that Nikki is grabbing her boobs. As soon as the blindfold comes off, Nikki dives face first into Shalina's pussy. In return he earns himself a BJ that rocks his world.

Shalina has Nikki seated on his lap and riding his ding dong before he knows it. She gets on her side while Nikki spoons behind her and keeps her pussy party going. Getting to her knees, Shalina leans forward and thrusts back as Nikki pounds her. She ends up back on Nikki's stiffie as she rides in reverse cowgirl until he gives her a creampie. Nikki has passed the milf test, but Shalina wants to keep him for herself.

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