Missionary (266)

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.

Elias and Spikey are off to college, and their stepmoms, Alexis and Kenzie, will miss them dearly. The two milfs express to one another that they want nothing more than to be pregnant. To see their dreams come true, the cunning milfs hatch a scheme to have their stepsons cum inside them before they go away to college. Alexis and Kenzie blindfold their stepsons, and when the blindfolds are removed, Elias and Spikey are shocked to see their stepmoms bent over in front of them, pussies out, ready to be fucked. It feels good to fuck each other’s stepmom, but Alexis and Kenzie want to get fucked by their own stepsons, so they initiate a sneaky swap to make things even kinkier.

College Bound Cream Pie

After Brandi’s divorce, she seeks comfort in her friend Silvia who invites her and her stepson Joshua to go on a getaway trip with her and her stepson Tyler. Once they all get settled in, they spend some time by the pool where Brandi confesses to Silvia that she hasn’t had sex in a really long time and is feeling extremely horny lately, so Silvia tells her how she’s been picking up young boys at the college bars lately and has been having a blast! They both point out how handsome each other’s stepsons were and come up with a way to swap and seduce them!

Recovering From the Divorce

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

Natasha, her husband and her stepson Elias are getting their house ready for their New Year’s party, and soon their neighbors Kenzie, her husband and her stepson Josh arrive to celebrate. Kenzie and Natasha have been feuding with each other for a while and tonight Elias and Josh wanna help them call a truce. Once the husbands are passed out, Natasha starts coming on to Josh and giving him a blowjob while Elias starts eating out Kenzie, but she notices Natasha blowing Josh and loses it! The two stepmoms start fighting but their stepsons have has enough and so they decide to fuck them until they make peace with each other… the best way to start the year!

Home for the Holidays

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

Julia is concerned about her stepson David’s recent uptick in masturbation and expresses her concerns to her friend, Arabelle. Luckily Arabelle has a solution and offers to talk to David one-on-one. Julia then learns from Arabelle’s stepson, Oliver, that Arabelle’s methods are pretty “hands-on.” When Julia walks in on Arabelle giving David a handjob, she explains it’s to ensure David has a positive attitude toward sex. Arabelle gives Julia a much-needed lesson in the art of cock worship.

A Lesson in Cock Worship

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

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.

Robby Echo is skeptical of the new neighbors, who seem to carry a dark aura around them. His stepmom, Carmen Valentina, assures him that Aria Khaide and Oliver Davis are nothing more than friendly, so she takes Robby to meet them. But upon their arrival, Aria and Oliver seem to have a strange affection for one another, and despite her efforts to ignore them, Carmen can’t help but feel aroused. Aria hatches a scheme to help Robby lighten up, and with the help of Oliver and Carmen, the plan is soon underway.

BFFs Cara and London just can't believe what's going on: the blondes woke up to realize their boobs have gotten huge! Their breasts are suddenly gigantic, bringing the attention of Rion and Max, their stepbrothers. The girls feel a bit awkward about the boys staring at their massive chests, but they also think that they should get even somehow. Max and Rion beg them to show them their juicy knockers, something Cara and London are willing to do if they get to see the boys' cocks. After a quick titty flash, Max and Rion are flabbergasted, so they pull down their pants to discover their generous dicks. Cara and London can't believe how well-endowed the boys are, so they exchange a horny complicit glance and agree to suck each other's stepbro's cocks to avoid feeling uncomfortable. Yet, as the gals get their mouths stuffed, they realize that maybe sucking their own stepbrother is not a bad idea, especially if they move on to their starvin' pussies next. The guys are more than willing to plow their stepsisters, and the joy is doubled as they observe how Cara and London get their cumholes filled while making out. Nothing is off the table as the busty girls eat pussy while getting fucked.

Blessed with Big Boobs

School life isn’t easy for Macy and Nade, two nerdy step-siblings who are constantly bullied. Sofie and her stepbrother Nicky are always humiliating them, and the geeks have had enough of them, so they devise a plan to give them a taste of their own medicine. By sneaking into their place, Macy and Nade capture some raunchy videos that showcase a different side of Sofie and Nicky. Now, holding all the power, Macy and Nade have some requests for Sofie and Nicky. Sofie knows that Nade is desperate to get his cock sucked, so offers him a blowjob in exchange for him deleting the video. Nicky doesn’t like the idea but accepts it once Macy offers to blow him, too. The negotiation soon becomes a full-blown swap session, yet the step-siblings can’t help but check each other out. Amidst everyone being naked and exposed, Nade and Nicky wonder what it might be like to fuck their own stepsisters. They don’t have to wait long to find out, as the girls are also curious about getting dicked down by their stepbrothers.

Don't Mess with the Nerds

Joshua and Lilly enjoy giving people a rough time, but they've made a big mistake after targeting Deliliah and Tyler. When these two get compromising film on the pair of bullies, it's time to beg for forgiveness and give in to their enemies' secret and perverted sexual desires if they don't want to lose everything over leaked sex tapes.

We Can't Lose Everything

It’s Valentine’s Day, and Elias and Rico are again left without Valentine's sweethearts. These nerdy dudes are never going to get laid if they don’t start making an active effort to put themselves out there. Luckily, their stepsisters, Bailey and Melanie, want to help the guys and ensure they don’t spend another Valentine’s Day alone. The girls start by giving their stepbrothers a makeover and putting them in some more appealing clothes. They then decide maybe it’s time for their stepbrothers to have kissing lessons. Elias isn’t so sure, but Rico encourages the lesson, knowing that this chance won’t come up again any time soon. Rico and Elias can’t believe they’re making out with each other’s stepsisters. Could this be a dream come true? The girls are pretty turned on themselves, and despite Rico and Elias being total dorks, they are pretty cute, and they’re fast learners, too. To really show their commitment to helping Elias and Rico, Bailey and Melanie set the guys up with dates. But the dates end with no kiss, which the girls were half suspecting. They don’t want their stepbros to be upset with the results of the date, so Bailey and Melanie once again offer themselves up to the guys. This time, however, Melanie wants to take things all the way. She doesn’t want the guys to be virgins forever, and if Bailey is cool with it, Melanie suggests a sis swap - Bailey will have sex with Elias, and Melanie will have sex with Rico. It sounds ridiculous at first. Were Bailey and Melanie really about to fuck in front of their own stepbrothers? But the more the thought crept into their minds, the hornier they got. It would easily be the most taboo thing they’d ever do, and who knows, maybe their stepbrothers had big cocks. So they go along with their plan, but neither Melanie nor Bailey can take their eyes off of their own stepbrother. Even while getting fucked, they make eye contact and think about how wild it would be to get fucked by their own step-family. The desire becomes too much to resist, so they switch again so that Elias and Rico are now fucking their stepsisters. Everyone knows how fucked up the situation is, but they also feel incredible. All the pent-up sexual energy since their kissing lessons are released in full force, and that only makes everyone in the room even hornier. When the guys can no longer hold their loads, they bust their nuts on their stepsisters' faces, who then share a cum glazed Valentine’s Day kiss.

Be My Naughty Valentine

Prev Page 4 of 12 Next