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DatingMyStepson.com Episodes - Season: 4
Playing My Cards Right - S4:E1

Playing My Cards Right - S4:E1

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 Jayden Marcos trying to impress Pristine Edge, mom to Rachel. Pristine deals cards to Jayden, but eventually the date turns into strip poker. Things start getting spicy as Pristine's luck turns sour, although Pristine tries to remind herself that they're here for her daughter. Once her tits are out, though, Pristine gives in to the chemistry between herself and Jayden. She crawls across the table, palms his boner, and makes it clear he can have anything he wants. Once Jayden has sampled Pristine's pussy with his tongue, he stands up and shoves it in. Then Pristine crouches in front of him, licking his balls and shaft clean. She gets to her feet and leans forward over the table so Jayden can do her from behind. As they wind down, Pristine sits Jayden down and demonstrates her fitness by fucking him in cowgirl until he's ready to pop. She gives Jayden a handie until he blows on her stomach, and they both bask in the afterglow of a good fuck.
9.28 161 14 May 3, 2024
Learning Some New Moves - S4:E2

Learning Some New Moves - S4:E2

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.
9.3 185 9 May 16, 2024
Putting In The Effort - S4:E3

Putting In The Effort - S4:E3

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. After a brief makeout, Cassie peels off her dress to unveil a stunning body with hot lingerie and Juan goes in for a pussy feast. In return, he gets his dick and balls sucked. Getting to her feet, Cassie leans forward over the kitchen island so Juan can do her from behind. Juan takes his turn on the counter so Cassie can mount him in cowgirl and ride him until she's arching her back in delight. Climbing off, she gets on her back so Juan can keep their party going. He gives Cassie one last big O, then cums on her stomach. Although Cassie gives her blessing to Juan, Juan thinks he'll keep looking for another milf.
9.26 139 6 May 29, 2024
A Game Of Dare Always Spices Things Up - S4:E4

A Game Of Dare Always Spices Things Up - S4:E4

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. Alex admits that he cheated when he was younger, then tells Shalina his longest relationship was six months. When Shalina chooses dare, Alex tells her to show him how she chops wood. That gives them an excuse to get close together. When they get rained out, Alex sits down to a meal where he has to admit he's vegan. After another round of truth or dare, Shalina lets Alex get busy a different type of meat as she shows off her tits and then her ass. Soon Shalina is sucking Alex off and then he's eating that juicy pussy. Since Shalina is already on her back it's simple for Alex to adjust his position to glide home into her greedy twat. From there they spoon together and then Shalina rolls to her side for a doggy style dicking down. When Shalina gets on top, there's no stopping her until she's sated. She rides in cowgirl before turning around and riding in reverse cowgirl until she has milked a creampie and a promise to really consider choosing Amirah from Alex.
9.8 155 5 Oct 3, 2024
Dropping My Balls In Her Moms Pocket - S4:E5

Dropping My Balls In Her Moms Pocket - S4:E5

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. Once Alex has enjoyed a bunch of pool shots against Rebecca's ass and pussy, they agree that they're two consenting adults and that anything can happen while they're on a date. To that end, Rebecca is soon top off with Alex sucking her nipples and palming her pussy beneath her miniskirt. A moment later, Rebecca is on her knees with Alex's dick in her mouth as she enjoys an intense blowjob. Alex gives right back, licking and lapping at Rebecca's clit. Getting to his feet, Alex shoves into that greedy cooch. Rebecca moans at the completion, then stands up and leans forward over the table so Alex can do her from behind. The couple get back on the pool table together so Rebecca can ride in cowgirl. Turning around, Rebecca rides Alex in reverse cowgirl until he pops inside her. Dripping with Alex's creampie, Rebecca gives him permission to date her daughter.
9.4 102 7 Oct 18, 2024
Manifesting A Great Fuck - S4:E6

Manifesting A Great Fuck - S4:E6

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. Very spiritual, Veronica leads Alex inside to interview him. Her room is a reflection of her personality, which weirds Alex out, but he tries to be openminded as Veronica attempts to manifest his spirit. Once Veronica has seen Alex's aura, she opens herself to him. She immediately finds herself overwhelmed by Alex's sexual energy. Unable to help herself, Veronica is soon sucking Alex down in a voracious blowjob. She can't stop there. Rolling to her back, she invites Alex to cum inside. He tugs Veronica's thong aside dives deep, making her throw her head back in delight. Spooning together as they keep fucking leads to Alex laying on his back while Veronica rides him in cowgirl. Then he gives her a pussy pounding in doggy and lets her finish them both off as she rides him to a creampie in reverse cowgirl. Although Veronica feels guilty, Alex points out that their chakras have aligned perfectly now and that will transfer to Veronica's daughter.
9.11 93 6 Nov 1, 2024
There Is No Resisting Her Mom - S4:E7

There Is No Resisting Her Mom - S4:E7

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. Their game reveals that Alex wants to take care of Texas’s daughter but he’d also fuck the hell out of her for a first date. Alex can feel the connection between himself and Texas, and finds that he’s less interested in her daughter than in her. They come together with a kiss that turns into Alex eating Texas’s pussy. She pops those big naturals out for Alex to enjoy, then crawls forward to suck her new lover’s dick. On her back, Texas watches with hungry eyes as Alex shoves into her landing strip snatch. They spoon together and keep on fucking. Then Texas gets on her knees for Alex to show her how he does it doggy style. They finish with Texas on top, first riding in cowgirl and then turning around to pump a creampie out of Alex in reverse cowgirl. Texas gives permission to fuck (or date) her daughter.
9.15 53 5 Nov 20, 2024
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