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Clothed Sex (147)

Anthony comes home tattered and humiliated, and he admits to his stepmom, Jessica, that he is being bullied at school. Jessica demands Anthony reveal who his bully is. Soon after, Jessica calls Savvy, the stepmother of Anthony’s bully, Dylan. Jessica isn’t going just to sit around idly while her stepson gets the snot beat out of him. Jessica and Anthony pay Savvy and Dylan a visit. If Dylan wants to be a bully, Jessica will show him what a real bully looks like. The powerful milf lays across Dylan’s chest, and she isn’t wearing any panties, and Dylan can see right up her skirt. Jessica doesn’t care - Dylan is a naughty boy who needs to be taught a lesson that only a milf can teach. Jessica demands that Savvy learn to be more assertive, and she can use Anthony to learn how. Savvy pulls her dress up and rides Anthony’s face. Then, Jessica has Dylan watch as Anthony fucks his stepmom. Dylan sees that he shouldn’t be a bully anymore, and now that the group is thoroughly turned on, they get right to fucking. Now that the boys have gotten past their beef, they can become friends as they fuck each other’s stepmoms. The milfs love getting the dick down from younger studs, too. The guys fuck the mature chicks hard until both Anthony and Dylan shoot their loads.

Swapping To Teach A Lesson

While their stepmoms are on vacation, Nicky and Parker mess around with their stepsisters. They use their stepmom’s sex toys no less, thinking that they will never find out. But when Angel and Nicole return, they discover what sorts of antics their stepsons have gotten into. To teach the boys a lesson in impulse control, the busty milfs decide to undress and rub their tits and clits all over their horny stepsons’ bodies. Nicky and Parker aren’t allowed to touch. But when the lesson gets too hot for even Angel and Nicole to resist, all they want is for their stepsons to fuck their eager, dripping pussies.

Impulse Control

Parker is looking to Kai's fraternity, and neither of their stepmoms can be prouder of them. Cassie and Elana visit their stepsons in their dorm to give them their well wishes. But when the milfs see Kai putting Parker through the wringer, they step in to make things right. Elana knows Kai had to go through similar experiences, and she knows how often her stepson gets laid - she just wants Kai to make sure Parker gets the same college experience. Cassie appreciates Elana's help and is gracious when Kai wants to perform a fraternity ritual then and there with the whole group. Kai blindfolds Cassie and initiates a cock sucking ritual. The whole situation seems wild and kinky, but everyone in the room starts feeling excited. Cassie wonders if her stepson is taking peeks through his blindfold to watch her suck cock. She knows it's fucked up to be thinking about her stepson in such a way, and she isn't sure what she'll do if she ends up having to suck Parker's dick. It's too kinky to think about, and the fact that her stepson's cock excites her feels insanely inappropriate. Still, both milfs feel immensely turned on by the situation. Parker and Kai have fun getting their cocks sucked, but they really take things to the next level when everyone starts fucking. Everyone's blindfolds come off, and that means the stepmoms get to look at their own stepson's cocks all they want. Kai fucks Cassie hard, and Parker doesn't hold back on Elana, doing everything he can to ensure he gets into this fraternity. Things get even more fucked up when the stepsons initiate a stepmom swap! Now, Cassie finally has her chance to see what it's like to get the dick down from her stepson. Parker penetrates his stepmom and thrusts his throbbing cock deep inside, making sure to give her every inch he can. The milfs get hot creamy loads to the face and share cum-drenched tongue kisses.

Welcome to the Frat Swap

Daya and Madison plan to surprise their stepsons, Jimmy and Joshua, with NBA finals tickets. Daya breaks the good news to Jimmy, her friend’s stepson, who is beyond elated. Daya goes to find Madison and Joshua, only to witness the unimaginable. Daya can’t believe what she’s seeing - her stepson and her friend going at it in the locker room shower. Jimmy stops Daya from interrupting them, and as a way of settling things, he proposes that he and Daya have some fun of their own. She agrees, and Jimmy and her get to work. This time, Daya and Jimmy get caught by Joshua and Madison. With everyone now on the hook, it makes sense that both milfs finish their fun. Jimmy will continue fucking around with Daya, and Joshua will keep having fun with Madison. The group sex is kinky and exciting, but things get even more wild when Daya starts sucking Joshua’s cock. Joshua can’t believe his own stepmom is there naked with his cock in her mouth. The excitement keeps climbing as the guys get to experience a full-on MomSwap. Fucking their own stepmoms is simply outstanding, and the guys fuck the milfs hard until they both get to shoot their loads.

It’s the end of the world as we know it, and all anyone can think about is getting laid one last time - or for the first time. Misty and Vivianne are looking for a little action, and their stepsons, Jimmy and Parker, are terrified to die virgins. The group knows they have to jump into action, and since it’s the last day on Earth, who cares anyway! Misty squirts all over Parker’s cock, and Vivianne is impressed - she wants a little bit of her own stepson’s cock for herself. Parker and Jimmy fuck Misty simultaneously, and she is over the moon. In the end, it was all worth it.

End of the World Swap

Sienna hasn’t seen her friend in years and is astonished by the kind of lifestyle she has. How can Cherry afford all this luxury while she is drowning in debt? Willing to help her, Cherry confesses her secret: she’s an exotic dancer. Sienna knows her friend has always been hot as hell, but she never imagined she’d put a use to it, and she’s also a hot milf, so maybe Cherry can help her make some money with her curves! Sienna begins training her bodacious friend in the art of pole dancing. First, she has to dress like a provocative temptress. Next, she has to try out her powers to seduce guys, and who better than their stepsons Elias and Max to start? Elias isn’t fully comfortable with his stepmom dressing slutty, but as soon he feels step-mommy’s thick ass on her crotch, he sits back and enjoys the show. Maybe Sienna has an actual talent, and who’s Elias to question her? Plus, both he and Max love their stepmom’s cock-sucking talent, and they are more than happy to see them shine as long as they get to pound their pussies too!

I Want to Be an Exotic Dancer

Ever since Crystal's divorce, her life has been a bit tumultuous. Crystal's friend, Alaina, calls to check in and make sure all is well. The milfs reconnect and decide to meet up. A little get-together after not seeing one another for a long time is just what Crystal needs to feel better. Both Crystal and Alaina are stepmoms now, so Parker and Rion will be joining in on the get-together. Things go off without a hitch until Crystal and Alaina start messing around with each other's stepsons. The milfs know it's wrong, but they're both so horny and messing around with younger guys isn't an opportunity they get super often. Parker and Rion don't give it a second thought, although they know if either of them found out, they'd be furious. Things go south when the stepsons do discover the little fling. Crystal and Alaina calm the boys down, and the best solution they all agree on is recreating the sex in a fun environment where everyone can watch. At first, things are a little weird - fucking in the same room and seeing their stepsons naked is both odd and thrilling for the milfs. When things start heating up, the group opts for a swap. What would be kinkier and more fun than fucking their own stepsons, after all?

A Swap to Make Amends

Lauren and Nickey go way back, so when it comes time for their high school reunion, they're beyond excited to go together. So much has changed in their lives. They were once raunchy chicks exploring the world, fucking guys, and living life to the fullest. Now Lauren and Nickey have left all their antics behind and are full-time stepmoms. Their stepsons, Joshua and Matt, are totally oblivious to Lauren and Nickey's old lifestyle, although the boys have their suspicions. Lauren and Nickey are very eager to see one another, and they're both total milfs - it would be easy to see them getting into all types of slutty adventures. Lauren and Nickey head to the bedroom to change, leaving Joshua and Matt alone in the living room. Matt wants to know more about Joshua's relationship with Lauren. It seems like Joshua is always happy to do whatever Lauren tells him. Matt finds it weird that someone would get so much joy out of following their stepmom around, doing their bidding. But Matt doesn't know about Joshua and Lauren's relationship. Joshua explains that he and his stepmom are fucking all the time. Ever since her divorce, Lauren has been sad, but even more than sad, she's been unimaginably horny. Matt is taken aback and can't believe what he's hearing. Fucking your own stepmom sounded insane, and it was totally fucked up. But the more he thought about it, the hotter the idea became. Soon, Matt's head was filled with thoughts of himself positioned over Nickey, his cock deep inside of her pussy, and her calling out his name in a barrage of pure lust. It wouldn't be so weird, and she was just a stepmom, after all. If Joshua was doing it with Lauren, why couldn't Matt do it with Nickey? Meanwhile, in the bedroom, Lauren and Nickey reminisce on their youth. Another wave of horniness strikes Lauren, and her pussy is starting to get wet just thinking about the dirty acts she and Nickey used to get into. Lauren and Nickey decide it might be fun to mess around a little for old-time's sake. The milfs jump right into the fun. They've missed each other's bodies, but it feels like no time has passed at all. Their tits and pussies are familiar to one another, and it feels incredible to be back in action. While Lauren eats out Nickey's pussy, Matt and Joshua enter the room, catching the ladies entirely off guard. Lauren is excited to see the boys, but Nickey is slightly more concerned. Matt had never seen her like this before, but now that he was staring her down, she could feel herself becoming even more turned on. Matt tells Nickey that Joshua and Lauren fuck all the time and that he wants his chance to fuck his stepmom. Nickey is flattered, and the situation just seems to get hotter and more taboo. At first, Nickey isn't sure about letting her stepson fuck her, but the primal sexual desire in her is mounting to an all-time high. To make things easier, the stepsons swap stepmoms - Joshua will fuck Nickey, and Matt will fuck Lauren. It's an easy enough trade and still exciting enough to rock everyone to their core. The milfs show the younger guys that older women know way more about sex and kinky pleasures. The busty babes bounce up and down and let their stepsons lie back and enjoy the sex. Matt can't take his eyes off of his own stepmom, and Nickey knows it. They both want each other with a fierce passion and even start to dirty talk. They get swept up in the moment, and when they can no longer resist one another, Joshua and Matt swap back so that they can now fuck their own stepmoms. Filling his stepmom's pussy feels even better than Matt anticipated. It was a special connection he'd wanted with her for a long time, but never knew that fucking her would be the solution. The feeling is mutual, and Nikcey wants Matt's cock inside of her as deep as it can go. The group session is an intoxicating experience for everyone involved. Having more people in the room watching them fuck added an exciting element to Laruan and Joshua's already taboo relationship. Joshua and Matt cum hard on their stepmom's tits, making sure to give the milfs every drop they can. The two milfs feel young again and couldn't be any happier with their lives than in that moment.

For Old Times Sake

Tyler and Franco are looking to have a good time after their adult bar mitzvah, so they attempt to find sex workers online. Their idea fails when Angelica confronts Tyler and Franco. Angelica calls Alex immediately so they can talk things out with their stepsons. But Angelica has a plan that may help Tyler and Franco on their journey toward manhood. Alex will fuck Franco, and Angelica will fuck Tyler so that they lose their virginities to someone they trust. However, the fun doesn’t end there, and soon the stepmoms swap, so they both get to fuck their own stepson!

Stepping Into Manhood

Lindsey steps in to help her childhood best friend, Slimthick Vic, who has fallen into hard times since her separation. Lindsey invites her to the NHL Finales so the two friends, as well as their sons Elias and Rico, can reconnect. Afterward, the two families spend the night together. When Vic catches Lindsey fooling around with her stepson, they all realize that lines have been crossed, but will cross even more taboos in order to soothe feelings of loneliness.

NHL Turns Me On

Charlie and Julia, two ultra-conservative and religious moms, are extremely disappointed in their stepsons. They were caught watching porn, so the stepmoms need to teach them to be men of god. Charlie and Julia then decide to punish them by making them watch the film while “conditioning” them to realize that porn is dirty, and the first step on the road to damnation. However, this plan backfires on them when they get a little too turned on by the whole situation.

When Charley and Mandy find boner pills in their stepsons' bedrooms, they know they must address the situation immediately. Nicky and Parker explain that they’ve been busting nuts way too fast when they’re with their girlfriends. As expert sex therapists, Charley and Mandy jump into action right away. Together, they teach Nicky and Parker all sorts of ways to last longer. The milfs push their stepsons further and further until they reach the final step – a good old-fashioned stepmom swap!

Nut Bust Conundrum Swap

Lolly and Sandy are celebrating Thanksgiving together with their stepsons Nicky and Juan and they notice that the boys have been super depressed lately. They sit them down and have a talk with them, and they discover that they both were recently dumped. Lolly and Sandy have a great plan to cheer up their ungrateful stepsons, they will swap and fuck them! Lolly sucks Juan’s cock while Sandy sucks Nicky’s, and suddenly the boys have a lot to be grateful for!

Ungrateful No More

After a whole year of celibacy, hot MILF friends Mandy and Vivianne decide it's time to get back in the game. They're both super horny and ready to jump back on the wagon, but they don't want their husbands to be the ones to pop them. Instead, they prefer to get themselves some young male cocks that can actually keep up with them. It so happens that James and Nicky, their stepsons, are young, hunky, and eager to help. As Vivianne and Mandy get fucked by each other's stepsons, they realize that swapping might not be a bad idea...

A Celibate No More!

Nurses Joslyn and Kate have a hard time making their stepsons Nicky and Victor go to their doctor’s appointment. When they find the boys playing video games they suspect they didn’t go to their appointment so they take it upon themselves to do the physical check up. They swap and Joslyn takes care of Victor’s cock while Kate inspects Nicky’s boner. The stepmoms agree they have to get the “specimen” and finally give both their boys a very thorough inspection!

Naughty Nurses Swap

It’s time for the camp meeting, and milf stunners Mckenzie Lee and Syren de Mer couldn’t be more excited. Their stepsons, Billy Boston and Tyler Cruise, are hatching a plan of their own, though, to earn the “Fuck Your Mom” badge. If they fuck each other’s stepmom, then they can walk as legends with this mysterious and taboo badge. But the stepmothers don’t make it so easy at first and give the studs a run for their money. If they want those badges, they’ll have to earn them and show their actual skill.

The Forbidden Badge

Penny Barber and Rachael Cavalli are on a sales mission, but getting to their goal seems like an impossible feat. That is until Penny comes up with the ingenious idea to involve Joshua Lewis and Tyler Steel in the sales process. Using a special ingredient that only Joshua and Tyler can provide, Penny and Rachael plan on seeing a massive increase in sales.

The Queens Of Cream

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

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

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

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