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Pleasure (145)

Aaliyah Love is passionate about showing hospitality, but after giving out a house-warming gift that causes tension between her family and the newcomers, this busty, hot, and willing MILF is going to have to go all-out in proving there are ways both parties can help each other.

A Heartfelt Welcome

When best friends Rion King and Jay Romero are training for their big game, their respective moms Cindy Crawford and Sofie Marie make sure that they stay focused by prohibiting masturbation and sex. The boys are desperate to sexually release their pent up energy so Cindy and Sofie decide to swap their sons and teach them how to masturbate without cumming, promising a big reward once they win the game. After their big victory, Cindy and Sofie swap again to deliver their promised reward… a simultaneous fuck sesh with the boys on the couch!

A Lesson on Edging

Mayara and Tiffany sit on the living room floor with their art pads in hand. They’re trying to draw nude male models, but without the anatomy in front of them, the milfs are having difficulty capturing the image. Behind them, their stepsons, Jimmy and Nicky, attempt to snatch a credit card and a phone to watch premium porno in the bathroom. Tiffany walks in on Jimmy mid wanks, and he begs her not to tell his stepmom, Mayara. Tiffany then gets a devious idea - what if Jimmy and Nicky served as their male models? Tiffany brings the guys into the living room, where they strip nude. It started as just a funny idea, but after seeing their impressive cocks, Tiffany and Mayara are beginning to feel horny. So they claim they want to get the guys hard as a reference for their drawings, but really, these horny milfs want to see what Jimmy and Nicky can do with their big dicks. So they aren’t messing around with their own stepson, Mayara sucks Nicky’s cock, and Tiffany sucks Jimmy’s. Their lust is getting insurmountable, and now instead of just sucking dick, the milfs want to have their pussies filled. While Tiffany is getting railed by Jimmy, she can’t help but wonder what her own stepson’s cock would feel like inside of her. Mayara feels the same way, but fortunately, she doesn’t have to wait long to find out.

Nude Models Wanted

London and her stepson Nade watch every football match together. As the new season starts, she is not happy to hear that Nade wants to break their tradition by inviting his friend Nick over to watch it. London is upset but she simply can’t refuse. The problem is that Nick brings Vic, his stepmom, a young and sexy milf that dresses slutty and makes London feel less desirable. And to make things worse, Nade just can’t stop looking at Vic.
Feeling left out, London tries seducing her stepson’s best friend as a way to boost her self-confidence and give her stepson a message. The plan works too well, as Vic and Nade catch her giving Nick a hot blowjob in the kitchen. Instead of getting mad, Vic and London talk it out and discover that they both feel jealous and insecure around each other. They finally decide there is no point in them competing, so they swap their handsome boys to have fun with them while watching the game, turning the event into an unforgettable match.

An Unforgettable Match

With the upcoming NBA finals, Carmen and Crystal reminisce about when they played on their high school basketball team. After seeing their stepsons' disbelief, they challenge them to a game, which doesn’t go as they planned. However, hitting the shower after the match is a must, the perfect excuse for the two hot stepmoms to play a different game with Elias and Rion.

Back to the Cooter (Part 2 of 3): Carlos and Jimmy are flung from the year 1995 to 2013 after fucking their virgin stepmoms. When they return home, something feels different - and their stepmoms notice it, too. Kiki (Chloe) and Sasha (Venus) are stunned when Carlos and Jimmy are wearing the same clothes as the guys who took their virginity in 1995. Kiki and Sasha have the guys show them their cocks to prove their suspicions. Now the milfs feel frisky and want a round two with their stepsons. Carlos fucks Kiki, and Jimmy fucks Sasha, but after a while, the horny babes want to feel their own stepsons’ cocks inside them. After Carlos and Jimmy finish, they learn that in this new timeline, they have stepsisters. What does this mean for the future? Only Part 3 holds the answers!

Back to the Cooter Part 2: Return Trip

Alexis and Barbie are two recently divorced friends eager to rock their single lives. The two go for a weekend getaway in LA to forget their exes and do a little experimentation. Their stepsons Parker and Rion tag along for the fun, shooting videos all over the luxurious house they are renting. While taking shots of the house, the boys discover their stepmoms kissing and rubbing each other by the pool. Shocked, they interrupt the whole lesbian scene and lock themselves in their room. Alexis and Barbie feel a bit awkward, but they are also turned on by the situation, so they make a pact of seducing and fucking each other’s stepson, a sweet revenge on their cheating ex-husbands.

Revenge Is Best Served Young

Rion and Robby have wet dreams, and their stepmoms, Bunny and Bridgette, must devise a solution to help them. They decide to make molds out of their pussies for the stepsons to use whenever they want. When the guys don’t know how to use the portable pussies, Bunny and Bridgette jump into action once again. Bunny helps Robby, and Bridgette helps Rion, but they initiate a stepmom swap when things start heating up! Now, Rion and Robby get to fuck their own stepmoms and really make their wet dreams come to life!

A Dream Cum True

Mona and Kenzie invite their stepsons Nade and Nick to join them in a friendly tennis showdown as practice for an upcoming mother/son tournament. It’s the perfect opportunity for the gals to step outside and feel accomplished one more time. Kenzie and Mona are clearly more experienced and competitive, so they get worried when they see their stepsons are not nearly as good as they need them to be, so they decide to swap sons and practice with them 1-on-1. What they don’t know is that the reason why their boys are so distracted is because they are horny just from watching each other’s stepmom play! Mona and Kenzie are nothing if not understanding, so they help Nade and Nick cool down their boners with a hot foursome, so they can focus on properly learning how to play tennis.

Joshua and Rion come up with a plan to make their stepmoms lend them the car. Rachael and Sedona are hardcore basketball fans so Joshua and Rion pretend to like watching the game to get on their stepmoms’ good side. Rion knows that Sedona is into him so they swap stepmoms and fuck them good!

A Swapping Plan

Elias and Parker are two friends that are afraid to go to school, so they pretend to be sick so their stepmoms Payton and Skylar don’t force them to go. Unfortunately, the principal calls them and blows up their whole cover, so the boys need to come clean about their situation.
Turns out Parker and Elias are constantly being bullied and called pussies because they cannot talk to girls, so their stepmoms will have to step up to boost their confidence and help them get along with women.

Sandy and Sydney want to create special memories for Easter with their stepsons, Chris and Parker. Each year, they all wear pastel clothes, have an easter egg hunt, and a family photo. However, this year, the sons aren’t that into it, so they make little to no effort figuring out where the easter eggs could be. The boys decide to look in Sandy’s bedroom, and they do find some eggs, just not the ones they were looking for! Now Sandy and Sydney have to explain what kegel eggs are and how they work, but since their stepsons aren’t the brightest bulbs, they require a little more firsthand experience to really understand how these eggs can keep their stepmothers’ pussies tight and young.

Those Aren't Easter Eggs

Rion and Oliver run into an unexpected roadblock while working on an “art project.” With no other hot chicks to use, Rion and Oliver get help from their stepmoms, Demi and Lory. When things get intense, Rion hesitates, but Lory quickly helps him change his attitude.

"Art Project" Swap

Joshua and his stepmom, Aaliyah, have an unexplainable tension between them that they’d like to resolve. That’s when they decide to visit a spiritual healer, who they believe can strengthen their bond. However, when Aaliyah and Joshua arrive, things are not what they expected, and both Ashley and her stepson, Tyler, are like something out of a pagan cult.

Letting the Love in

After a little talk Aaliyah decides to follow her friend Penny’s advice and try out therapy for her and her stepsons Joshua and Tyler. Penny happens to be a therapist who has all the credentials to be able to take care of this case. Turns out the way to get deep into the boys’ issues was to let them fuck them! Joshua and Tyler each take their turn with Aaliyah and Penny as they show the deep love they have for their stepmom!

A Transformative Session: A Deep Analysis Extended Cut

Bunny and Mona are always concerned about the well-being of their beloved stepsons, Diego and Ellias. The two busty stepmoms can’t bear the thought of the boys getting sick or getting hurt if they were to leave the house. But all Diego and Ellias want to do is fuck hot girls, so they hatch a scheme to sneak out of the house. Their plan is foiled when Bunny catches them in the act. Now, Bunny and Mona will need to think of a way to keep the young studs content with staying home. Luckily they’ve got just the right idea. Ellias will fuck Bunny, and Diego will fuck Mona. The stepsons can’t believe their luck as they slide their cocks deep inside each other’s stepmoms. These milfs love every second of it, and even though they know it’s wrong, it just feels so right. So right, in fact, that they decide to spice things up and swap.

Don't Worry, Just Swap!

Scandal In Suburbia: A Dee Williams Mini-Series [Part 3 of 3] - Previously, on Shoplyfter Mylf, Dee helped get Rion and her stepson, Joshua, out of trouble by showing off her persuasion skills. Now the boys are off the hook and are hanging out in Rion’s kitchen. But when they recount how Dee fucked the security officer, Rion’s stepmom, Nadia, overhears the perverted story. Nadia flips out and calls Dee to confront her, only to find out Rion fucked Dee just the other day. To get Nadia to loosen up, Dee shows her that she can be a cool stepmom, too. Joshua, Rion, and Nadia help bring Dee’s pervy milf story to a climactic end.

Scandal in Suburbia: Part 3

When Katie and her stepson Joshua welcome their new neighbors Reagan and her stepson Lucky to the neighborhood, Joshua notices there’s something weird about them. Joshua tells Katie that he suspects them to be vampires, but of course she doesn’t believe it. While Joshua confronts Lucky, Reagan seduces Katie and bites her in the thigh! Joshua and Lucky find Reagan teaching Katie all about being a vampire, and now he must learn how to take her of her urges!

The Vamp Next Door

Mellanie instructs her stepson Diego to stop wasting his time on his podcast and instead fold the laundry. Diego and his friend Rico start sorting through the laundry when Rico finds Mellanie’s underwear and starts sniffing it! Diego is taken aback at first but when Rico tells him about how much money they could make selling them online, the boys are determined to steal all of their stepmothers’ underwear! Mellanie and Ms Visual find out what they’re up to and decide to swap the boys and teach them a very naughty lesson!

The Underwear Thieves

Emmy and Ophelia ask their stepsons David and Rion if they could help them get in shape since they’re always working out. David and Rion agree to help, but only if they swap their stepmoms. Emmy and Ophelia are willing to do anything to get a good workout… including sucking the other’s stepson’s cock!

Sexercise Routine

Busty milfs Barbie and Cassie have caught their stepsons, Anthony and Nick, spying on their stepsisters. The milfs know they must show their stepsons the value of privacy, so they set up their own webcam to spy on the guys. Anthony and Nick catch on immediately and jerk off so their stepmoms see their dicks. Barbie and Cassie can’t help but get turned on. Later, while Barbie and Cassie are in the kitchen, they realize that Anthony and Nick are spying on them. But this time, they’re ready to have some fun, and they want to fuck around a little. Nick fucks Barbie, and Anthony fucks Cassie, but to make things even hotter, the milfs swap so they can get fucked by their own stepsons!

It Takes Two to Spy

Sophia notices her stepson Nade has been having serious issues at public school. When talking with her friend Cory, she tells her she home-schools her stepson Nick for the same reason and offers to help Sophia out by letting Nade take a couple of fundamental courses with her.
A few months later, Nade seems to be doing better and showing significant growth in all his core subjects. One day, Sophia decides to drop in unannounced and is shocked to find both Nade and Nick taking turns to eat Cory’s pussy. The teacher explains to her that this is a sex education course, another key subject the boys need to learn about. After the initial shock, Sophia accepts that Cory’s teaching methods do give results, so she decides to volunteer herself to help Nick and Nade learn more about sex ed.

HomeSchool Sex Ed

When Athena is at her wit’s end with her stepson Tyler’s bad attitude, she calls her therapist Jenna asking for guidance. Jenna relates with Athena, having gone through the same issues with her stepson Franco during her divorce. Once they’re all sitting down together, Jenna teaches Athena that the best way to make them help out is by encouraging them with sex!

Lessons on Motivation

When Kenzie and Pristine learn their stepsons, Oliver and Elias, plan to enlist in the military, the busty babes do everything they can to stop the boys from going. Oliver and Elias get an intense boot camp experience, but when the intensive training isn’t enough to deter the boy’s dreams, Kenzie and Pristine rely on extreme measures.

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