Jeans (14)

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

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

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

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

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

Celestina Blooms and Cody Carter have a sleepover with Gia DiBella and Tyler Cruise. When Cody and Tyler find nothing to do with no TVs in the house, their next move is to bother Celestina and Gia. The four opt for a game of “Truth or Dare,” which doesn’t take long to heat up.

A Daring Sleepover

It’s been three months since the apocalypse commenced, and there are no signs of any other survivors. Joshua and his best friend David, as well as their stepsisters Britt and Mae, are left all alone together. Although they are all virgins, they feel it’s time to come together in efforts of enacting a repopulation plan.

Cumming Together

Payton Avery and Sophia Leone just want to party, but they’re stuck at home with their stepbrothers instead. It’s up to James Angel and Jayden Marcos to keep the girls entertained, but their idea of a good time is less than thrilling. Bored and unable to focus, Payton and Sophia express they’re just too horny for guessing games and take matters into their own hands to liven up the living room. After a push and some good old-fashioned encouragement, James and Jaden make this the best game of their stepsisters’ lives.

Pervy Guessing Games

When stepsiblings Tyler Nixon and Lily Larimar visit their friends AJ and his stepsister Kylie Rocket they expect to have a great time during their slumber party. Kylie and Lily decide to watch a scary movie and wait for their boyfriends to sneak in to have some fun, but Tyler and AJ play a prank on them, put on some scary masks and spook them. The guys sneak into their room and decide to swap their stepsisters and eat them out from behind! The girls think is their boyfriends at first, but when they discover that it’s their stepbrothers they agree to continue having fun as they were doing a great job eating them out!

The Seductive Art Of Massage - Scene 1

The Seductive Art Of Massage - Scene 1

I got caught shoplifting again, but I didn't understand why they were making a huge fuss about it again. I had already fucked the store manager, so I thought they wouldn't give me a hard time anymore, especially not after how deep I shoved his dick in my throat. Yet, there I was again, getting my big tits groped as the security guard searched for stolen merchandise on my naked body. I have to admit that his hands felt amazing on me, but there was no way I was ever going to admit it, even if he was squeezing my butt as if it was the best thing he had ever felt. When he bent me over his desk and took off my G-string to search inside my asshole, I knew how good he would be at fucking. I even shocked myself by moaning, but I couldn't control it! Things got even more intense when he used his tongue to search even deeper. Sure, I was supposed to be pissed and hesitant, but when he said "I'll let you go if you let me fuck you until I cum," I was so turned on I had to say yes. I thought I was leaving with new underwear, but instead, I left with his cum on my face.

Case No. 8004218 - Scarlett Is Back For Seconds (Pervz Singles Sequel)

Steve (Elias Cash), his girlfriend Cassie (Leana Lovings), and their mutual friend Danny (Victor Ray) are playing poker. When Cassie takes a break and goes into the kitchen to make snacks, Danny suggests a wild bet: whoever loses the next hand gets to fuck the other guy's girlfriend. Steve playfully accepts, not thinking the bet is serious. But when he loses, he finds out that Danny was completely serious about it.

When Cassie finds out about the stakes of the bet, she seems furious and decides to go along with it to make Steve feel bad for using her in a bet. Steve eventually leaves, dejected and humiliated, but once he's gone... the truth reveals itself.

PureTaboo - 2025.11.11 - Leana Lovings - Up The Stakes

It’s Mother’s Day again, the time of year when we celebrate MILFs worldwide. Olivia and Sophia are as hot as they come, so their stepsons, Billy and Chris, want to make sure this is the best Mother’s Day ever! Things get a little spicy when Billy and Chris present their moms with an unexpected “gift.”

MomSwap.2022-05-09.Olivia Jayy, Sophia Locke

Anya and Ellie are both desperate for grandchildren! They've tried everything to sabotage their stepsons, Jimmy and Nicky, hoping to get their girlfriends pregnant. Desperate to have babies back in the family and still being attractive and fertile ladies, they plot to get impregnated by each other’s stepson. With the excuse of teaching the boys about the basics of sex and how to keep their girlfriends satisfied, they lure them into a steamy session. As Jimmy and Nick are fucking each other’s stepmom, they feel tempted to swap, pushing their own boundaries by making babies with their stepmoms!

MomSwap.2024-01-15.Anya Olsen, Ellie Taylor