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Cowgirl (269)

Mysteries & Moans (part 3 of 4): This investigation keeps getting kinkier and kinkier. But I haven't seen enough yet. I need to see things play out in front of my very eyes. Luckily, I think Axel and Rion can help me in that department. I have a fucked up little swap plan that'll give me a clearer picture of the fucked up dynamic in this stepfamily. But will these guys really fuck their own stepmoms? Of course, they will - once they see those beautiful bodies, they won't be able to resist...

Mysteries & Moans Part 3: Romi's Private Show

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

Anthony and Axel want to lose their virginities, but they’re having trouble finding girls. Concerned, their stepmoms, Aviana and McKenzie, step in to save the day. The women don’t want their boys constantly worrying about sex, and if losing their virginities means a healthy mental release, they’ll do anything to help. Their plan is taboo but should go a long way for Anthony and Axel. Essentially, the milfs plan to surprise the boys with tantric sex - they’ll swap stepsons so that Aviana gets fucked by Axel and McKenzie gets fucked by Anthony. It’ll still be pretty intense, fucking as a group and being sexual in front of each other. Still, the idea of being so vulnerable in front of their own stepsons excites both Aviana and McKenzie. Their plan is set in motion, and Aviana and McKenxie dress themselves in sexy lingerie, letting their tits and pussies peak through the thin lace. Anthony and Axel are completely blown away and are immediately concerned. They know it would be totally fucked up to mess around with their own stepmoms, but when they learn the plan is to swap, they start to come around to the idea. They still know it’s a bit out there and is wrong to fuck in front of their own stepmoms, but they’re so horny at this point they’ll do anything to lose their V-cards. The milfs climb into bed and give each other’s stepsons blowjobs. It’s an exciting feeling, and both milfs can’t take their eyes off of their own stepsons. They want to see just how much they’re enjoying getting their cocks sucked. The mature chicks know it’s wrong, but it feels so right in the moment. The milfs then let the guys fill up their pussies, letting them release all of their pent-up sexual frustrations in an instant. But they still can’t help but wonder what it would be like to be filled up by their own stepsons. Unable to resist any longer, they finally initiate a full-blown swap. It’s intense for everyone involved, and each person knows just how taboo it is, but getting to feel their own stepmom’s pussy is even better for Anthony and Axel. The lucky studs have to do everything not to cum right away. They want to show their stepmoms how appreciative they are for helping them lose their virginities. The milfs get fucked hard until the guys can no longer hold their loads. Anthony and Axel cum hard on their stepmom’s faces, covering them in a sticky mess. The milfs share a cummy kiss and let the intensity of the moment wash over them.

Swapping Tantric MILFs

My friend Sasha has always been rich, so when I was struggling with money, she let me and my stepson crash at her place. I knew she did it so she could brag about her fortune because the first thing she showed me was her fancy dildo. It was big and fat, but most importantly, it was made of gold and sapphire! I've never had anything that expensive inside me, so I wondered how it would feel. When she wasn't looking, I took it to my room, but her stepson caught me! I thought he was going to tell Sasha, but instead, he helped me hide it. Sure, the place he chose to do so was my pussy, and I wasn't expecting it when he shoved it in, but it felt good anyway. Then, he said that since he helped me, I should help him too. He dropped his pants, offering me his hard cock. Sasha saw us and got so jealous that she seduced my stepson. When I confronted her, her dildo slipped out of my pussy! She said that since I stole it, now I had to watch my stepson fuck her. Watching him pound her wasn't as bad as I thought. I was even getting horny myself. When Sasha spread my legs and asked her stepson to fuck me too, I was so relieved. That was what I needed. I wonder if asking them to swap would be too much, but it was worth the risk.

You Stole My Dildo: Now Watch Your Stepson Fuck Me

I can't believe my stepson is going away to college. What am I going to do without him? I know my best friend feels the same way. We're both worried our stepsons are going to forget about us the moment they get there. They promised they wouldn't, but we needed to be sure, so we came up with a plan to make them remember us. We are going to let them fuck us. She'll take care of my stepson, and I'll take care of hers. Our Fourth of July party is the perfect opportunity for that. We'll play trivia and let them win. Every time they answer correctly, we'll show them a part of our body. After they've seen our perfect, bouncy tits and wet pussies, they won't resist shoving their hard cocks inside us. If they still don't think we can party as hard as college girls by then, we'll swap. A foursome will make them come home all the time, and they'll be thinking about our mouths on their dicks for a very long time.

Fourth Of July Trivia: Why Do Your Stepmoms Fuck Better Than College Girls?

Alaina and her stepson Jayden have a lovely relationship, but it’s not as intimate as the one between his best friend Sage and his stepmom Jessie. Still, Alaina how close it was: she didn’t know Jessie was fucking her stepson every single day. Even if she struggled to admit it, the first time she saw her choking on Sage’s cock, she felt really jealous… maybe she wanted to have that too? Whatever doubts she might’ve had went away as soon as she saw her Jayden fucking Jessie’s throat while she herself choked on Sage’s pole. The gloves where off and she was gonna fuck her stepson no matter what.

Stars, Stripes & Wieners: Memorial Day Swap

Parker and Jimmy are two geniuses who love using their wits for pervy stuff. Their latest invention is a pervy VR experience involving their hot stepmoms Alexa and Vivianne. In this Virtual World, they are kings and can grope them however they want to, with the chance to feel their big and juicy tits and firm asses. The experience is so realistic that the boys lose track of time and play away. However, in the real world, Vivianne and Jimmy notice the boys with their pants down fucking the air. Rather than losing their minds, they decide to give Jimmy and Parker a taste of reality by sucking their dicks while they still think it’s all VR. Soon, the whole situation becomes a fuck fest, with Parker and Jimmy fucking each other’s stepmom without even knowing. Yet, suddenly, the VR glasses come off and the guys realize what they are doing. The boys try to call it off, but the horny stepmoms convince them to finish with what they started and to go all the way with them.

Ethan and Jimmy have been very supportive of their stepmoms Elise and Samantha having a night out on Valentine's Day, after all, it can be a tricky night for lonely moms. What they didn't know was that they had a secret weapon: a magic powder that would make any man fall for them almost instantly. However, as luck would have it, they're the ones who ended up sniffing it! After Elise and Samantha returned from their shitty dates, these young studs were horny and ready to make this the greatest Valentine's Day ever! After all, they've always loved their step mommies... haven't they?

Sloppy Valentine's Day Mom Swap

Mandy and Sydney, two sexy stepmoms, have decided that they are going to dress sexy this year for their first Halloween after the divorce from their awful husbands. Unfortunately for them, their exes came up with excuses and left them stuck with their boys, Berry and Nicky. The gals are pissed because their plans to have a sexy night of fun are in danger, but they might as well make the best of it and come up with some new horny ideas. Mandy and Sydney agree that they can swap and have sex with each other’s stepson, a situation that soon evolves into a lusty foursome.

Sexy Halloween Treat

Ethan and Jimmy have been very supportive of their stepmoms Elise and Samantha having a night out on Valentine's Day, after all, it can be a tricky night for lonely moms. What they didn't know was that they had a secret weapon: a magic powder that would make any man fall for them almost instantly. However, as luck would have it, they're the ones who ended up sniffing it! After Elise and Samantha returned from their shitty dates, these young studs were horny and ready to make this the greatest Valentine's Day ever! After all, they've always loved their step mommies... haven't they?

Sloppy Valentine's Day Mom Swap

Jimmy and Ethan want to score, so they go online to find some hot, willing women. The horny roommates catfish some older babes into a conversation but soon become enamored by their sexiness and allure. The guys don’t realize, however, that they’re talking with each other’s stepmoms. It isn’t until Jimmy starts titty fucking Sydney and Ethan messes around with Vivianne do the women realize the situation. But seeing Jimmy’s cock, Vivianne feels a sense of excitement. She knows that her stepson’s dick shouldn’t turn her on, yet there she was, craving him and wanting a taste. She can’t help but get on her knees and get a feel of her stepson’s throbbing dick in her mouth. It’s so wrong, but it turns her on immensely, making her pussy wet with excitement. No one can believe what’s happening, but seeing Vivianne suck her stepson’s cock makes Sydney want to try her stepson’s dick, too. Jimmy and Ethan are at a loss for words, knowing full well that this whole situation is pretty fucked up. Things get even more intense when the women want their pussies filled up. To make things a little less taboo, Sydney and Vivianne swap, so as not to get fucked by their own stepsons - spoiler alert, that won’t last long! The group sex is kinky and wild, but it would be even hotter if Jimmy and Ethan had more of that forbidden fruit. They initiate the Mom Swap and get a chance to fill up their own stepmoms. It’s been a while since these mature women have been fucked by younger studs, and they love feeling young and naughty again. Sydney and Vivianne ride hard until they have their stepsons blowing their white-hot, creamy loads.

Cougars Catfished Into Filthy Swap

So I'm going to be a married man. Whoop-de-fucking-doo, right? At first, I was on top of the world. Spending the rest of my life with my soulmate? It's a dream come true. And, hey, it's not like I don't like my fiance. It's just... Fucking one person for the rest of my life? That's a scary thought. And that's where things get really fucking weird. I go to vent my problems to my stepmom and my best man's stepmom, who're both in their wedding dresses. What the fuck? I brush it off and think, "Ah, what the hell, they're feeling nostalgic." But then, as I was explaining my reservations to my stepmom, she and her friend pounced on me like a tigress hunting her prey along the banks of the Ganges, slinking low to the ground, her every step a sultry declaration of dominance. Her eyes burned with a pang of hunger so intense it could melt glaciers - her muscles rippled like forbidden poetry, and her claws - oh, her hot milf claws - poised to deliver one swift, devastatingly seductive swipe that whispered, 'You're mine.'" Well, maybe not quite that weird, but shit, I'm sucking on my friend's stepmom's titties and he walks in. Things really get weird when we start fucking each other's moms in front of each other. But, of course, that wasn't enough for these women - they want some of their own stepson's cock.

I Cheated Minutes Before My Wedding... With My Stepmom!

Little Puck and her stepson Mike have America's hottest and naughtiest podcast. Their dirty minds always think about each other and help other stepmom-stepson duos realize their potential. These milfs have cock on their minds 24/7, and they can't wait to see what sort of heat their stepsons are packing. The audience can't get enough of Little Puck's perfect body, so you know they'll go insane for Madison Blaze. On air, the stepmoms get their pussies filled to the max! Their stepsons will never want to fuck another woman again when they see how amazing their stepmom's lips feel wrapped around their cocks...

Swapcast - Where Stepmom's Talk Dirty

Abi and Lola feel that their teenage stepsons, Axel and Dylan, are drifting away from them. Desperate to make some new family memories, the milfs decide their boys have to spend Saturday with them playing games. This situation that overwhelms the boys soon becomes awkward. What they don’t know is that the ladies have a secret ingredient to spice things up and give their teenage boys that extra kink they desperately need. While playing Twister, their bodies start touching accidentally. The big winner decides what her prize will be a dare: Everyone who loses must take off their clothes. The room gets even more awkward for Axel and Dylan, but as soon as they realize how sexy their stepmoms are, their worries are blown away, and things get even more heated. They have all kinds of hot ideas for the dares, and they’re great at Twister.

What can two milfs do when they find out both of their husbands are cheating on them? Easy: Have an affair of their own, but for these horny women, getting even is not enough. They need to make everything steamier and kinkier by having a foursome with their hot stepsons who are more than ready to fuck their brains out.

Hijab MILFs Have Pussy Shattering Affair

Apollo and I are so concerned about the future of our country that we’ve never really had time for girls. We know our stepmoms worry about that, but we never thought they’d take it this far. What started as an innocent election night challenge quickly evolved into the two ladies gagging on our cocks and now, as my stepmom is about to ride me and Apollo’s stepmom spreads her legs open for him, we know the future of our cocks is looking brighter by the second.

Getting The MILF Vote

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

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