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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 Cherry Kiss, mom to Lindsay. Parker Ambrose, the potential suitor, is a bit confused about the show’s premise, but he’s game since the normal dating scene isn’t working out.Once they’ve returned from their dinner date, Cherry tells Parker they aren’t done yet. She wants to make s’mores and then have him for dessert. Coming up behind Parker as he roasts a marshmallow, Cherry wraps her arms around him. She gently maneuvers him back against the counter to kiss her way down his body to pop his hardon out. Assuring Parker that her daughter won’t be home for a while, Cherry goes on to suck him off.Determined to take Parker for a thorough test drive, Cherry gets to her feet and lifts one leg to the kitchen counter so Parker can shove in from behind. Laying Parker on the ground, Cherry licks her own juices from his dick and then mounts him. Cowgirl makes this mommy moan as she rides. Getting on the counter, Cherry opens up for Parker one final time. He pumps Cherry to climax and then enjoys his own orgasm as Cherry kneels in front of him. Now Parker knows he’ll choose Cherry’s daughter.
Runtime: 2:52
Added: 2025-01-08
Tags: fair skin mini skirt blonde
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Whitney Oc has been called in to babysit her friend's son, Ricky Spanish while his parents are out of town. Ricky wants to watch scary movies, but he also wants to watch his hot babysitter as she shakes her ass in the kitchen. When Whitney joins Ricky on the couch, he puts his head in her lap. Whitney is having none of it, especially when Ricky tells her that if he has nightmares he's going to join her in bed.Later, Whitney is getting ready for bed when Ricky knocks on the door. He can't sleep after all those scary movies. Whitney says he can stay for a few minutes but he's not sleeping with her. After a moment, Whitney relents and has Ricky put his head in her lap. Then she pops her tits out so he can suck on them. When Ricky is sufficient at that, Whitney has him eat her pussy. If he wants to stay, he'd better give her dick.Knowing Ricky is turned on, Whitney pops his hardon out to suck him down. Then she crawls on top of him and rides the D in her landing strip cooch. Getting on her knees, she instructs Ricky to keep on dicking her down. On her back, Whitney has Ricky plow her until she's moaning, and then she strokes him off until he nuts all over her chest and boobs. Now that Ricky is drained, Whitney kicks him out and tells him she'll call him back if she wants to cum again.
Runtime: 2:40
Added: 2024-10-25
Tags: shaved pussy brunette milf
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Alexis Malone and Jena Larose are sharing some gossip when their stepsons Parker Ambrose and Jay Romero arrive home. The guys instantly begin making a huge mess in the kitchen. Sighing, the ladies go to clean up before Jena declares that they should leave the mess for their stepsons to clean up. Instead, they grab some wine and popcorn and sit on the couch chatting about dicks.When Jay overhears the conversation, he accuses Alexis of being a bad influence on his stepmom. Jena bites back that he can either rub Alexis's feet or go to his room. Then Jena tells Parker to get busy eating her out. Taking her cue from Jena, Alexis has Jay give her snatch the same treatment. Then the ladies swap out their stepsons so that Jena can suck Parker off and Jay can enjoy feeling Alexis's lips wrapped around his fuck stick.Now that the ladies have gotten going, they aren't about to stop without a full stepson swap fuck fest. Jay dicks Jenna down in doggy while Parker and Alexis get it on in the same position. Switching partners, Jena rides Parker in reverse cowgirl and Alexis does the same for Jay. The ladies get on their backs, with Jay doing Jena and Alexis and parker going at it. When Jay pulls out to nut on Jena's stomach, Parker follows suit with Alexis before the guys exchange a fist bump above their stepmilfs.
Runtime: 2:57
Added: 2024-01-31
Tags: shaved pussy panties blonde
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Covid is causing problems once again as Ricky Spanish is on his own because his parents have to quarantine. Two nurses, Alura Jenson and Reagan Foxx, are taking care of his parents and also taking responsibility for Ricky. In return, Ricky is being quite the brat. The MILFy nurses go to his room to wake him up, but Ricky is still asleep. They pull the top covers off of him, at which point Ricky claims he's sick. The nurses have already tested Ricky for Covid so they know he's lying. They announce that they're not his mommy and they won't be fooled by him. Pulling the sheet down, Alura checks Ricky's temperature rectally. The nurses can't help but see that he's rocking a huge hardon, so with a wink between themselves they decide to milk Ricky's prostate so he won't be hard all day. Reagan is the first to go beside Ricky for a handie, but Alura is right there a hot second later. Together, the bigtit nurses take care of their surprised patient with their hands and mouths, and even their big boobies.Getting Ricky to cum doesn't turn out to be a wham bam thank you ma'am type of deal. He's still raring to go as Alura mounts him in cowgirl. She hops off and sucks her girl goo from Ricky's stiffie so that Reagan can have a go in cowgirl, too, as Alura provides her jugs to be suckled. Getting on her knees, Alura takes a doggy style pussy pounding while she eats Reagan out. The nurses tag out with Reagan getting the D and a mouthful of sweet snatch juices. One her back, Reagan lifts one thigh as Ricky gives it to her, then switches spots with Alura so she can have one last go. When Ricky pulls out to blow his load on Alura's muff, Reagan is there to lick her clean and then share the jizz with a snowball kiss.
Runtime: 5:27
Added: 2022-07-29
Tags: shaved pussy blonde brunette
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Armani Black loves to dress nice and sexy. Showing off her big bazongas is priority number one for any outfit this milf puts on. Knowing that she's about to meet her fiance's parents, she pours herself into a sexy black dress and then out to where her soon-to-be stepson Jimmy Michaels is sitting to get his opinion. Jimmy tells her that it may be too sexy for his grandmother's taste, so Armani goes to change.The next day, Armani is wearing a sheer lace top that can barely constrain her breasts and a short little miniskirt. Jimmy walks in to see her doing the dishes and agrees to help. Anything to get closer to those titties. When Jimmy learns that Armani is going to a tutoring position dressed like that, he protests. Offering Jimmy a sexy little smile, she offers to tutor him. Before he knows it, he has his Armani on her knees in front of him, sucking and stroking him while offering him a position as her boy toy.Armani gets her wish as Jimmy bends her over the counter and slides her miniskirt up so he can fuck her right there. He fondles her pierced nipples and jiggles those jugs as he bangs her from behind. Then Armani gets Jimmy to lay down on the countertop so she can ride him in reverse cowgirl. Her boy toy loves those jiggling tits in his face when she turns around. Taking Jimmy's stiffie on her back, Armani squeals and moans as she reaches her peak. A hot minute later, Jimmy pulls out to blow on her stomach. They bask in the afterglow as Jimmy realizes his life is going to be a lot more fun with a new stepmom.
Runtime: 3:47
Added: 2023-05-10
Tags: high heels mini skirt shaved pussy
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Veronica Leal has plenty of passion in her younger milf body. She also has the hots for her stepson, Charlie Dean. She finally actions on those desires when Charlie walks in on her mid-workout and begins making out with his new girlfriend, Lya Cutie.Turning so Charlie and Lya can see her ass perfectly, Veronica continues stretching until Lya asks for lessons. That gives Veronica the chance to get her hands all over the redhead. Charlie can't hide his arousal at watching the girls stretch, so when they make it clear they're eager to tag team him he doesn't resist. He just lets it happen as Veronica and Lya make out in front of him while sharing his dick.The ladies aren't about to stop there. Veronica masturbates as she watches Lya's technique riding her stepson's dick. When Lya climbs off, Veronica takes a turn in reverse cowgirl. She helps Lya onto her back so Charlie can plow that tight twat while Lya suckles Veronica's tits. Then Veronica climbs on top of Lya to create a double pussy stack for her stepson to enjoy. The trio winds down with Charlie delivering a nice cum shot to Lya's face, a treat she shares in a kiss with Veronica.
Runtime: 2:04
Added: 2024-04-03
Tags: masturbation shaved pussy hairy pussy
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Ricky Spanish may be an adult, but his mom doesn't trust him home alone. The last time he was home alone, Ricky masturbated in the living room and the neighbors saw him. When his parents go out of town for the night, his mom calls her friend Nickey Huntsman to babysit.There's sexual tension between them right from the start as Nickey makes jokes about the size of Ricky's hardon. When she has tucked Ricky into bed way too early, Nickey makes yet another jibe at the size of Ricky's hardon. He pulls it out with a rude comment, but to his surprise Nickey goes in for a blowjob instead of getting ticked off at him.Next thing Ricky knows, Nickey is on top of him riding the D in cowgirl as she shoves her tits into his face. Taking a moment to slurp her own cream from Ricky's hardon, Nickey climbs back on for reverse cowgirl. They spoon together and then Nickey rolls onto her back for Ricky to bring her off. When she's finally sated, Nickey lets Ricky blow his load on her big naturals, leaving them both pleased with the babysitting arrangement.
Runtime: 1:59
Added: 2024-01-05
Tags: shaved pussy brunette feet
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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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Remy Rune and Taylor Wild are making sandwiches and talking about how well they're sticking to their new year's resolutions. They get to talking about how their stepsons aren't taking theirs seriously. The ladies comment that they both catch their stepsons staring at their tits before going to bring them the sandwiches.Taylor immediately suspects her stepson Jodie Johnson has broken his resolution to not look at mom porn. Juan Loco has been looking, too. The milfs suggest that they use their imaginations to jerk off instead, and even offer to give the boys a titty show. When Jodie and Juan whip out their dicks, the stepmilfs are stunned at how nice they are. The titty show turns into a hardcore affair, with Remy sucking down Juan and Jodie enjoying a BJ from Taylor. The guys demonstrate they know how to eat pussy, and then it's no holds barred.Taylor rides Juan's hardon in cowgirl as Jodie gets the same from Remy. Then the ladies swap partners so Remy can get a dicking down from Jodie and Talyor can get a doggy pussy pounding from Juan. The milfs switch again for another round of doggy. Then Remy gets on her back for Jodie and Taylor spreads herself out for Juan. They both finish that way, then helps their stepsons get off too.
Runtime: 1:55
Added: 2026-01-16
Tags: black hair high heels mini skirt
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Eliza Rae is here to talk to one of her student's parents. She runs into her student's stepbrother, Charlie. Charlie reveals that he's home alone. When Eliza reveals that it's really imperative she talks to them today. She asks Charlie to bring her back to the apartment so she can leave a message with him to relay to his parents.Once Eliza has gotten Charlie alone, she reveals that his stepbrother has been making sexual comments about her body. He's even sending her unsolicited pictures of dicks he's been drawing. Charlie is very apologetic. He's so nice and gentle that Eliza gets an idea: She wants to give Charlie her number so he can text her regularly and send her real dick pics. Her come-ons get even hotter when teacher whips out her titties in a peekaboo bra that shows off her pierced nipples.Eliza is very convincing, especially once she gets on her knees to suck off Charlie's hard cock. Turning around, Eliza leans forward and offers herself to Charlie to fuck. He does her from behind and then gets her to sit on the chair so he can shove back inside as she watches him. Teacher keeps on schooling Charlie as she goes to work riding him in cowgirl. When she turns around and does him in reverse cowgirl, Charlie can barely hang on to the end. Eliza knows Charlie is close, so she gets on her knees just in time to receive a facial that leaves satisfied but already looking forward to next time.
Runtime: 1:31
Added: 2023-05-26
Tags: black hair masturbation mini skirt
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Pristine Edge and her friend Aiden Ashley want to get a group photo with their respective stepsons, Juan Loco and Max Frills. They feel that as the stepmothers, it's their job to teach their stepsons how to treat a lady. They inform the boys that they're doing a group photo for Easter, and after a bit of back and forth Juan and Max reluctantly agree.When Pristine and Aiden arrive for the photo wearing skimpy lingerie and bunny ears, the boys can't believe their eyes. Pristine crouches to fix Max's belt. In return, Aiden fixes Juan's hair. Max can't hide his stiffie, so without further ado Pristine goes for the D and begins sucking. She convinces Aiden to give Juan the same treatment lest the boys' hardons ruin the photo shoot.Once these horny ladies begin playing with the D, they aren't about to stop. Relocating to the couch, they sit the boys down so that Pristine can ride Max's dick in reverse cowgirl and Aiden can do the same with Juan. Sucking their own juices from the guys' cocks, they switch things up. Aiden goes for it in doggy with Max while Juan spoons behind Pristine. They swap partners one last time, with Juan giving Aiden a good pussy pounding until he nuts on her stomach. A moment later, Max pulls out from pounding Pristine in doggy to blow his load on her big boobies.
Runtime: 2:26
Added: 2023-04-05
Tags: fair skin shaved pussy bras
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Syren De Mer is just cleaning up around the house when she receives a text message. Imagine her surprise when she realizes that it's her son Nathan Bronson's dick and balls. Syren isn't pleased. Nathan insists it wasn't supposed to be sent to his own mom, but he won't tell Syren who it was meant for instead. Eventually Syren insists on seeing Nathan's phone, at which point she realizes that the photo was meant for Nathan's best friend's mom, Lexi Luna. Lexi is Syren's age, which leaves Syren in total disbelief. She sends Nathan to his room.A few days later, Syren invites Lexi and her son Rico Hernandez over to do some baking. The girls are just chatting about Lexi's marital problems when Rico comes in to ask whether he can go to the mall. Lexi stops Rico before he can go and offers him a blowjob before he goes. Lexi is shocked, but Rico is all for it. Nathan enters the room to find his best friend's dick in his mom's mouth, which is an understandable shock to him. That's when Syren tells Lexi that she knows about the dick pics Nathan has been sending, as well as the sexy pics she's been sending Nathan in return. Lexi isn't about to let Syren get away with having all the scandal in this situation, so she spreads her thighs and calls Nathan over to come lick her pussy.Obviously once the two couples begin this game of sexual chicken, they aren't about to stop with just oral delight. Both moms end up deep throating cock and delivering titty fucks. Then the girls get on their hands and knees so Rico can fuck Syren in doggy and Nathan can do the same for Lexi. The big boobie milfs go for a reverse cowgirl stiffie rides next. Hopping off the D, Syren kneels on the couch so her cooch is in Rico's face to create a sexy 69. Lexi does the same for Nathan. Laying on their backs on the same couch so their heads are close to one another, the moms both spread their things for one final round of pussy pounding. Rico delivers a delightful creampie to Syren, while Nathan gives Lexi the same treatment, a hot ending to a surprisingly sexy foray.
Runtime: 3:52
Added: 2022-06-01
Tags: black hair fair skin shaved pussy
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