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Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Sarah Taylor is the lucky lady who gets to date Jimmy first. The date that Pristine has arranged is a couple's massage.When Sarah comes out in her robe, she finds Jimmy trying to cover his hardon up and tells him not to bother. She's seen everything since she has a son his age. Things are going well right up until Jimmy rolls over at the end of the massage with a massive stiffie, only to lock eyes with his stepmom who was checking on the date. Trying to recover the magic Sarah makes a move by joining Jimmy on his massage table and locking lips with him as she grinds against his dick.Moving lower on the table, Sarah takes that nice erection in her mouth to stroke and suck. Mounting Jimmy, Sarah rides him in cowgirl with long strokes of her hips. Then she gets to her feet so Jimmy can love on her from behind. He presses her onto the table on her belly, diving nice and deep. Turning onto her back, Sarah spreads out for Jimmy to give her a grand finale before he pulls out and cums on her landing strip twat. As she basks in the afterglow, Sarah asks Jimmy to remember her.
Runtime: 5:35
Added: 2023-09-13
Tags: brunette milf enhanced
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Juan Loco is looking for something in the couch when his stepsister Freya Parker gooses him from behind. Juan grabs Freya's boobs in return. Although she clearly enjoys it, Freya eventually comes back to herself and tells Juan to cut it out and that she only grabbed him because he's not wearing green. Juan snaps back that St. Patty's Day isn't a real holiday and that she's only using it as an excuse to get Mona Azar, the teacher she has a crush on, to come over to give them a history lesson.Freya may have flounced out of the room, but Juan was right about the crush part. Later, Mona and Freya have just had a seat on the couch when Juan joins them. Mona also gooses him since he's still not wearing green, and Juan goes right for the boobs. Mona lectures Juan, who decides the proper response is to put a leprechaun hat on his dick. Exasperated, the girls decide to make out while Juan jerks off. The only rule is he can't cum.Kissing of course leads to so much more. Soon enough, Freya is tongue deep in Mona's creamy coochie. After sharing a kiss, the girls work Juan in a double BJ to include him in the action. He gets to fuck Freya in doggy as his stepsis returns to eating Mona out. Then Mona goes for a reverse cowgirl stiffie ride before getting on her knees so Juan can do her in doggy as she laps at Freya's twat. On her back and cradled against Mona's big bosom, Freya spreads herself wide open to fuck her stepbrother until he pulls out to nut on her muff. The girls share their treat with one last round of sweet kisses.
Runtime: 4:08
Added: 2023-03-10
Tags: black hair high heels masturbation
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Anya Olsen is overprotective of her stepson, Joshua Lewis. She's in the middle of telling her friend Lindsay Lee about how Joshua got in trouble for being in the girls bathroom. Anya tries to defend it, but it's quickly revealed that Anya holds Joshua's dick when he pees. Bemused, Lindsay calls her stepson Lucky Fae to come in along with Joshua.The boys give different accounts of what happened, with Joshua claiming he was pushed and with Lucky claiming Joshua was actually fucking a teacher. When Anya immediately jumps to Joshua's defense, Lindsay realizes how kinky her friend is. She suggests that Anya teach Lucky a thing or two about sex since Lucky thinks he's a gift to women. The girls agree to swap stepsons and both get their kink on. Lindsay takes Joshua to the couch, where she begins sucking him down. In return, Anya gets busy with Lucky's stiffie.The moms aren't about to just suck dick. They both want their pussies licked, so they lay down shoulder to shoulder and let the other's stepson go to work. Eventually Lucky sinks deep into Anya's snatch as she kneels and watches over her shoulder, while Lindsay climbs on top of Joshua's hardon. The girls each go for a reverse cowgirl ride and then get shoulder to shoulder once again so that Lucky can give it to Anya and Joshua can give it to Lindsay. As the guys each pull out to cum, the girls agree they should do this again.
Runtime: 3:19
Added: 2023-04-26
Tags: fair skin shaved pussy blonde
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Bunny Madison and Izi Blu Sky are fooling around with Izi throwing popcorn Bunny's tits when their stepsons walk in on them. The ladies claim it's girls night. Bunny invites them to girls movie night, and when they ask if they'll get pussy, Bunny says they'll find out.Later, Lucky Fate is sitting beside his stepmom when Bunny has her finger her pussy under a blanket. She claims she's going to take Lucky to go get more popcorn, but she really blows him while they all try to hold the moan. Meanwhile, Diego Perez is getting his cock sucked by his own stepmom. When it comes to light that they're all enjoying some horny time, they decide to do it together in a stepmom swap.After the girls exchange kisses and give their stepsons handies in the open, they get ready to fuck. Bunny lays on her back for Lucky to shove inside, and Izi gets her pussy pounded in doggy by Diego. The ladies switch it up so Bunny can ride Diego's fuck stick while Izi rides Lucky in reverse cowgirl. Then Bunny lays on her side for Lucky to give her the D as Diego dicks down Izi while she's on her back with her thighs spread. Lucky pulls out to pop on Bunny's buxom chest, as Diego cums on his stepmom's stomach.
Runtime: 3:16
Added: 2025-08-20
Tags: shaved pussy blonde brunette
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Dani Jensen has called her friend Slimthick Vic over to talk about some concerns she has with their sons. She has overheard the boys, Alex Mack and Lucky Fae, saying some things that make her wonder what on earth they're learning from the dirty videos they're watching. Dani suggests that the best way to break their sons of the bad habits they're learning is to date each other's sons. Vic thinks about it for a bit, but ultimately agrees that that's a good way for them to guide their sons and teach them how to respect women.The date itself turns out to be successful, but when Dani offers Alex a goodnight kiss he goes right in to grope her big boobs. Vic calls her son out for mauling Ms. Jensen, but Dani soothes her friend by suggesting that they help the boys learn how to give proper goodnight kisses. Soon, Dani tells Vic that the boys will get blue balls if they don't help them cum. Vic puts up some token resistance, but she really wants to get Lucky's cock as much as Dani wants Alex's. Now that the boys have been given permission, they can sit back and relax as their friend's moms pull out their cocks to stroke. Dropping to their knees, the girls each go to town sucking their friend's sons off.Sitting the guys down, Dani and Vic go for some real fun. Dani mounts Alex's cock in reverse cowgirl, while Vic gives Lucky the cowgirl treatment. Vic falls to her back with Lucky between her thighs, and Dani goes for it in doggy. When it's Vic's turn for a pussy pounding in doggy, she takes it with glee while leaning forward to suck on Dani's tits as the redhead gets it on her back. Alex pulls out to nut on Dani's muff, while Vic gets her bottom covered in cum by Lucky. The moms propose that they all do this type of date night every week.
Runtime: 4:11
Added: 2022-10-19
Tags: shaved pussy redhead blonde
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