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DatingMyStepson.com Episodes - Season: 3
Filled Up Before Dinner - S3:E1

Filled Up Before Dinner - S3:E1

This season on Dating My Stepson, we have three hot milfs and three eager stepsons to mix and match. On today's episode, Sam Bourne and Shalina Devine are having their date cooking dinner together. Sam arrives with a rose, which instantly pleases Shalina. They get busy, and it turns out that they work well together with their clothes on. All Shalina can think of is seeing if they work as well together with their clothes on the ground. Taking her chance, Shalina pours water onto Sam accidentally-on-purpose. It's of course on her to help him clean off. Dropping to her knees, she tugs Sam's pants down until his stiffie pops free. She wants to suck it, but first she daubs it with whipped cream to give them both a little treat as she gets down to the business of her BJ. Dinner is forgotten as Shalina gets in a chair and spreads her thighs for Sam to eat her pussy. Getting to his feet, Sam sinks balls deep into that velvet glove. They make good use of the chair, with Shalina on her back and then her side, winding up on her knees. Giving the chair over to Sam, Shalina sucks their juices from his hardon and then rides him in reverse cowgirl until he's close. Turning around, she goes for a ride in cowgirl until he delivers a creampie that's way more satisfying than any meal could ever be.
9.42 172 16 Feb 28, 2024
Candlelit Romance - S3:E2

Candlelit Romance - S3:E2

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. Finally giving in to her urges, Shalina lets Alex kiss her. Their passion is almost animalistic as Shalina gets to her knees and unbuttons Alex's pants. Once she lays hands on that hard dick, she can't stop from sucking and stroking. Shalina's tits are heavy and tender as she uses one hand to feel herself up and even rub her pussy while she continues to blow Alex. Leaning forward, Shalina moans as Alex finally comes into her from behind. She sucks their combined juices off his dick and then lays back so he can give it to her on her back. Climbing onto Alex's lap, Shalina rides him in cowgirl for the intimacy. Turning around, she goes for it in reverse cowgirl until he blows his nut inside her in a hot creampie
9.59 165 8 Mar 7, 2024
All In - S3:E3

All In - S3:E3

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. Once the two begin their kissing, they can't keep their hands off one another. The dealer makes his way out of the room, leaving Matthew and Kira to make their way over to the couch. Matthew eats his stepmilf out and then watches with hot eyes as Kira returns the favor by blowing him. Soon enough, Kira rolls onto her back and spreads her thighs to welcome Matthew inside. They begin in missionary with Kira on her back, but soon their passion heats up to even greater levels. Kira gets on her side so her stepson can slide deep inside as they spoon together. Then she gets on her knees so Matthew can really give it to her in doggy. When Matthew lies down on his back, Kira dominates him first in cowgirl and then in reverse cowgirl. That final position is all Matthew can take; he gluts his stepmom with a creampie that leaves them both breathless.
8.96 95 9 Mar 20, 2024
Coming Clean - S3:E4

Coming Clean - S3: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 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. Taking things back inside the house, they find that their chemistry has really ignited. Sam pushes Micky onto the couch to pepper her with kisses and eventually finds himself with his face between her thighs. He licks and suckles, then closes his eyes in bliss as Micky returns the favor by blowing him. There's no question that these two are going to go all the way. Sam eventually seals the deal as he sinks his cock deep inside. When Micky falls to her side with Sam spooned behind her, of course he follows her down to keep on going. Micky gets to her knees so Sam can give her a doggy style pussy pounding. Then she mounts him, enjoying every inch of his nice long dick as she rides in cowgirl. Turning around, Micky keeps on bouncing in reverse cowgirl until Sam cums inside her.
9.6 108 8 Mar 29, 2024
Playing My Cards Right - S3:E5

Playing My Cards Right - S3: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 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.
9.48 107 14 May 3, 2024
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