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Taboo (293)

I always wanted children of my own. It’s not that I don’t love my stepson, but I always dreamed of being pregnant and giving birth to a child. Now that my husband can’t give me that, it feels like my chance is going away. Luckly my best friend was going through the same thing so we could confide in each other. Around that time our stepsons came home from college and that’s when that little idea crept into her mind… we wanted to get pregnant but not by a stranger. So she said I should fuck her stepson and she would fuck mine. We knew that even though they were uncertain at first, they wouldn't pass on the opportunity to fuck two hot MILFS like us. What we didn’t anticipate is how much we would want to fuck our stepsons… now, as my own stepson is pounding my little pussy, all I can think about is his cum filling my pussy to the brim and making me a mommy once and for all.

NNN Challenge Day 21: Cum Inside, Make Mommy A Mommy

Ricky is having trouble with girls at school. He feels like his stature is getting in the way of landing chicks, and his friend Jimmy watches as Ricky lives his life in utter turmoil. Luckily for Jimmy and Ricky, their stepmoms, Annie and Ryan, are cool as fuck, and want to help the boys with their girl troubles. Annie and Ryan teach the guys about picking up chicks and let Ricky and Jimmy practice their lines on them. They want to see how the guys would seduce girls, and Ricky and Jimmy soon find themselves in a risque groove. Things get heated when the milfs put their hands on their stepsons’ cocks. Before anyone knows it, the group is deep in a full-blown fuck sesh. Ricky and Jimmy can’t believe they’re fucking each other’s stepmoms, though things get even wilder when they switch back and fuck their own stepmoms. The lucky studs give the milfs their all until Ryan and Annie milk Jimmy and Ricky’s cocks clean of all their juice.

Perfect the Way You Are

It’s the hottest day of the summer. Jenna and Vanessa are chilling in the back yard when Axel, Jenna’s stepson, and Rion, Vanessa’s stepson, come running to them with an inflatable pool to make the afternoon more bearable. They start with a game of marco polo, but the guys want to make the best of this hot day, so they propose switching to truth and dare. It starts innocently enough, with the guys daring Jenna and Vanessa to lock lips, which they do. Then they dare Vanessa to suck on Jenna’s tits and Axel even dives into his stepmom’s breasts to show her how! Then Rion dares his stepmom to fuck Axel, and promises to fuck Jenna himself to make it less awkward… A dare is a dare, so both MILFS drop to their knees and start gagging on each other’s stepson’s meat poles. They lie on the couch and spread their legs wide open to get dicked down by the guys, who take advantage of the situation and pound the fuck out of of them as hard as they’ve ever dreamed of. Vanessa and Jenna go into a 69 position while still getting railed and pretty soon they have their own stepson’s cocks in their slutty mouths. They know it’s wrong, but it feels so right. Axel pounds his stepmom’s pussy while Rion grabs his stepmom’s big ass and fucks her pussy deep and hard. The incredible fuck fest ends with both guys taking turns cumming all over the MILFS’ pretty faces.

Truth Or Dare Turns Into A MILF Swap Fuck Fest!

After a meeting with other parents, PTA moms Charli and Jade decided to carry out a new fundraising event for the benefit of the school. They’ll make a calendar with photos of the PTA Moms. However, Jimmy and Parker, their stepsons, are completely upset about them being that involved in the high school community, so they begin to mock them. They state nobody would ever buy a calendar with boring photos of old hags like themselves. Offended, the two milfs come up with the idea to do a sexier photoshoot, one that highlights their gorgeous bodies and makes a fool of their stepsons’ lack of judgment. Surprisingly, the two boys go crazy when they see their stepmoms in hot outfits and parading their luscious asses in front of the camera, so they start collaborating with them. Suddenly, both women begin to realize how much their stepsons have grown up. Soon, they will all end up naked and promising each other they’ll keep the secret.

Milfs Turn PTA Into Pussy, Tits & Ass For Students

Desiree and Mia are so sad their good boys are leaving for boarding school for a year, but their dads are right, if they don't leave their moms for a while they'll never man up, they'll be virgins forever! Elias and Dylan don't want to go, they love their stepmoms more than anything in the world, and the thought of being away from them for such a long time sucks. But then, just as they're about to leave, Desiree has an idea... if the problem is their virginity, they'll take it themselves! Elias is shocked, and Dylan can't believe it. Desiree explains to her stepson Elias that he'll get to fuck Mia and that her stepson, Dylan, will fuck her. They're hesitant, but as soon as the naughty MILFS start rubbing their inexperienced cocks through their pants, they forget all about that! The slutty older women suck their cocks and make out with each other as they ride their faces, before riding their best friend's stepsons' fat cocks! Then they go doggy and the guys can't help but try their own stepmother's pussies! Now they're the hesitant ones, but as soon as they go in the rush is so high that they almost cum on the spot! They keep sharing the guys in every position imaginable until they cum all over their faces like the good boys they are!

Hot MILFs Desiree Dulce & Mia James Take Their V-Cards On The Couch!

It’s Parents’ Day and Justine and Lilly are really looking forward to celebrating with their stepsons Parker and Anthony. They have a tradition that they love doing every year: foot massage, cooking a special dinner for their stepmoms, and then eating it all together. However, this year, Lilly and Parker started hooking up a couple of months ago, and they take any opportunity they get to be sexual with each other. Little do they know that during dinner, when Justine “accidentally” drops her fork and goes under the table to retrieve it, she’s actually giving Anthony a blowjob, because they’ve been secretly hooking up as well! Though it’s awkward for everyone at first, the stepmoms slowly realize that they can use this to improve their Parents' Day plan. After all, getting some young dick reinvigorates these two sassy milfs, and the boys are happy to please each other’s stepmom and get authentic lessons from experienced women. So what better idea than skipping dessert to have a deliciously nasty foursome, with orgasms for everyone!

Innocent Tradition Turns Into MILF Swapping Fuck Sesh

Chloe gets some lessons in stripping from her friend Frenchy. Chloe has wanted to learn for a while, and most of all, she wants to support her stepson, David. Frenchy and her own stepson have some bonding to do as well, so this is the perfect opportunity for both milfs to get closer to their stepsons. Chloe is a quick learner and looks immaculate on the pole, spreading her legs and showing off her perfect body. David feels horny for his stepmom while he watches her, and Chloe feels horny for him. They know it’s inappropriate to have such feelings, but they can’t help it, and each time they make eye contact, they get hornier and hornier. Things soon get too hot to handle, and the group can’t keep their hands off each other. They don’t want it to be too weird, so the milfs play with each other’s stepsons rather than their own. But even then, Chloe is thinking about being fucked by David even though it’s Joshua’s cock inside of her. The tension becomes too great to resist, so the group agrees to a Mom Swap. Now, Chloe will finally get the dick down from David. Having his cock inside of his stepmom feels so wrong but so right. David knows he wants to cum for her and show his stepmom how much he appreciates her love. Joshua fucks Frenchy hard to show her the same thing - she’s always worked hard to support him, and now he can show his gratitude. The lucky studs fuck their stepmoms until they both pump out hot loads of jizz.

You Know You Want to Swap

Mason and Parker are a bit odd, and their experience with girls is nonexistent, to say the least. Above all else, they seem so focused on being "Woke" and PC that it's getting in the way of enjoying the more risque adventures in life. Their stepmoms, Lindsey and Raquel, are fed up with the woke nonsense and agree to teach their boys a lesson in intimacy. Mason and Parker are stunned when the milfs whip out their tits and let the guys go to town. The guys know it's wrong and certainly not respectful behavior, but playing with Lindsey's and Raquel's giant jugs is too much fun. Things get even more intense later on when the milfs teach their sons a more profound lesson in love - fucking pussy. Mason and Parker get the chance to fuck each other's stepmoms before moving on to their own. It's the most inappropriate thing they've ever done, yet they can't resist burying their cocks deep inside of their stepmoms's pussies. When the guys can't hold their loads any longer, they pump a hot, sticky mess all over Lindsey and Raquel. The milfs let their boys cum all over their tits and in their mouths before sharing a cummy kiss with one another.

Don't Go Woke, Give Me a Poke

Karen Fisher and her stepson Robby Echo visit her good friend Syren De Mer and her stepson Nathan Bronson one afternoon. While the boys play in their room, Syren shares with Karen that the divorce has been rough, leaving her feeling lonely most nights and unfortunately, Nathan doesn’t let her take care of him like she used to. When the boys come back down needing some attention, Karen and Syren have the idea to swap their stepsons and show them what a real good time they can have with mommy’s friend!

Swapping Needy Boys

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

Friends Katrina and Millie join forces this Thanksgiving to celebrate the festivity together, accompanied by Elias and Ricky, their teen (and very horny!) stepsons. They are not that great at cooking, but they sure know how to prepare one delicious pumpkin pie. The problem is that their boys are at the age where their hormones are all over the place, and they’ve gotten the craziest idea from a movie they saw. Once Millie and Katrina step out to take a shower, Ricky and Elias go to the kitchen and start fucking the pie! Unfortunately, their stepmoms catch them in the middle of the act and go mad. Tired of their stepsons’ attitude, the two milfs decide to teach them a lesson on how to control their hormones and how to treat women properly.

Taste It with the Tip

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

Jimmy and Parker want to go to a party, but they’re shut down by their stepmoms, Mandy and Spencer, because it’s Yom Kippur. They must act tough, but Mandy and Spencer are just as horny as Jimmy and Parker and can’t wait to break their fast. Thinking they’re alone, Mandy and Spencer have a little girl-on-girl fun, but their stepsons catch them in the act. If the milfs want their stepsons to keep this a secret, they must offer something for their silence. The milfs get right to work and show Jimmy and Parker things they’ve only ever dreamed of!

Breaking the Fast

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.

Berry is watching porn on the couch when he notices something funny - Carlos’s stepmom, Misty, is in the video! Berry’s shock is amplified when the other woman in the video is HIS stepmom, Mandy. The women are showering together, soaping each other up and feeling each other’s tits. The boys recognize the shower as the one in their house, so they investigate the situation. Sure enough, the two milfy babes are in the shower together, now being watched by their stepsons. Mandy rubs Misty’s clit until she squirts hard and screams out in pleasure. But the boys are seen by their stepmoms and flee back to the living room. Now, Mandy and Misty need to lecture their stepsons and do whatever they can to keep this a secret. The solution? Berry and Carlos will get their own private show! This little stint turns into a full-blown fuck sesh! Eventually, fucking each other’s stepsons isn’t enough, and Mandy wants a taste of her own stepson’s cock. Misty needs more convincing before they can have a proper Mom Swap, but rest assured, you know she’s horny enough to come around.

Our Own Private Show

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

Valentine’s Day couldn’t be looking worse for Gigi and her stepson Elias. The vivacious blonde got stood up by her husband despite her getting hot lingerie for the occasion. Elias and his friend Nick got rejected by their girlfriends, who opted to fuck with college guys. And Millie, Nick’s stepmom, had the same bad luck, with her husband leaving her alone on the special day. Yet, this lustful foursome won’t accept no as an answer, and instead of fucking who they were supposed to, they are having a nasty swap session together! Gigi will try youthful Nick’s luscious dick while Millie gets to have her way with her best friend’s stepson, Elias. As the two milfs get sweet revenge while riding young cock, the boys get a lesson on pussy-drilling from two experienced ladies who know how to make them cum nice and hard.

Don't Waste Your Valentine Seed

Berry is watching porn on the couch when he notices something funny - Carlos’s stepmom, Misty, is in the video! Berry’s shock is amplified when the other woman in the video is HIS stepmom, Mandy. The women are showering together, soaping each other up and feeling each other’s tits. The boys recognize the shower as the one in their house, so they investigate the situation. Sure enough, the two milfy babes are in the shower together, now being watched by their stepsons. Mandy rubs Misty’s clit until she squirts hard and screams out in pleasure. But the boys are seen by their stepmoms and flee back to the living room. Now, Mandy and Misty need to lecture their stepsons and do whatever they can to keep this a secret. The solution? Berry and Carlos will get their own private show! This little stint turns into a full-blown fuck sesh! Eventually, fucking each other’s stepsons isn’t enough, and Mandy wants a taste of her own stepson’s cock. Misty needs more convincing before they can have a proper Mom Swap, but rest assured, you know she’s horny enough to come around.

Our Own Private Show

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

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