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DatingMyStepson.com Episodes - Season: 2
Massage Queen - S2:E1

Massage Queen - S2:E1

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. When Alex comes into the room, he begins the massage but finds that he's a bit shy in Kira's presence. She slyly asks if he wants to swap. Alex takes Kira up on it, and before he knows it he's getting the rubdown of his dreams with Kira's big tits on his skin and then her hands and mouth on his dick. How can Alex do anything but eat Kira's juicy coochie out in return? Since Kira is already laid out on the massage table, it's simple for Alex to spoon behind her and slide on home. That kicks off quite the fuck fest as Kira gets on her knees for a doggy style pussy pounding. When Alex lays down on the table, Kira goes for broke riding him in reverse cowgirl and then cowgirl. She keeps on pumping Alex's dick until he gluts her with a creampie to round out this first date.
9.47 156 9 Jan 3, 2024
Going Overboard On Her Pussy - S2:E2

Going Overboard On Her Pussy - S2:E2

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. Everything is going smoothly until Sam falls into the lake. Kira leads Sam indoors to the closest part of the house, where she begins to undress him so he can warm up. Kneeling in front of Sam, Kira tugs his jeans off and sees that he's packing a really nice cock. Knowing that Sam will heat up even more if she strokes it, Kira gives him a handie. That of course leads to her going back to her knees to suck him down and even pop those big jugs out for a titty fuck. No longer cold, Sam does some pussy exploration with his tongue that gets Kira moaning. Although he could go on feasting like that forever, Sam decides to get his dick wet as he takes Kira right there in that little bunk bed. They go to town in spooning and then Kira turns over so that Sam can keep her party going from behind. Getting Sam onto his back, Kira uses the bunk bed for leverage as she rides in cowgirl and then reverse cowgirl. She keeps up the good work until he fills her to the brim with a creampie, leaving just enough cum dripping down his own hardon for Kira to suck him clean.
8.65 147 7 Jan 12, 2024
I Aced Her Hole - S2:E3

I Aced Her Hole - S2:E3

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. Alex is fine with showing Micky the ropes, especially as Micky shows off her thong when she leans forward in her cute miniskirt. Things are going great until Micky accidentally hits Alex in the dick with her golf club. That cuts the date short as Micky leads Alex inside. Alex coaxes Micky into massaging his cock because he claims it helps him feel better. She offers to kiss his booboo, which is all the excuse she needs to stroke and suck Alex down. Peeling off her thong, Micky goes ahead and spears herself on Alex's hardon to ride him. There's no question about their chemistry as Alex pushes Micky onto her back and bangs her, then gets her on her knees and pulls her hair in doggy. Shifting to reverse cowgirl, Micky rides Alex for all she's worth until he aces her hole with a big fat creampie that helps him forget all about his injury.
9.51 139 11 Jan 25, 2024
It Started In The Jacuzzi - S2:E4

It Started In The Jacuzzi - S2:E4

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. When Micky beckons for Matthew to get out of the water, he follows her obediently to a convenient bedroom. They resume their kisses as Matthew explores Micky's body with his hot hands. Easing her down, he palms her pussy while worshipping her tits. Once Matthew has had a taste of her pussy, Micky needs a taste of his cock. It's only fair. When she has finally removed her bikini, Micky lays on her side as Matthew spoons behind her. Rolling onto her back, she moans as Matthew reenters her. Then he gets on his back so Micky can ride him, first in cowgirl and then in reverse cowgirl after a brief detour into doggy. Micky's reverse cowgirl stiffie ride milks the cum right out of Matthew in a creampie that seals their affection for each other.
8.96 123 11 Feb 7, 2024
Pleasure By The Pool - S2:E5

Pleasure By The Pool - S2:E5

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. After Micky barges in on the date, Matthew and Shalina decide to take off and let Micky have the hot tub. Micky comes to find them, claiming that Shalina forgot her towel. The ladies begin fighting over Matthew, who seems only too pleased to let Shalina suck his cock while Micky pulls her tits out for him to enjoy. When the ladies fight over the blowjob, Matthew just gets even hotter for both of them. Eventually the girls decide that fighting is pointless and they should use Matthew as a toy together. Now that they've decided to share, the girls treat Matthew as the fuck toy he is to them. Micky gracefully gives Shalina the first go on the D in cowgirl before she lays back to let Matthew do her as she eats Shalina's pussy. On her knees, Shalina rocks back to meet Matthew's strokes as she laps at Micky's snatch. Micky gets to enjoy Matthew's charms as she lays on her side with her mouth in Shalina's coochie and Matthew spooned behind her. Then Shalina climbs on and rides Matthew hard in reverse cowgirl, milking a creampie out of him that Micky snowballs with her. The two milfs agree they'll have to do more s haring in the future.
9.23 180 8 Feb 16, 2024
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