When Anna Claire Clouds decided to visit the sperm clinic she had no idea she would meet such a handsome Doctor Mancini. That man is going to breed her right here, right now, so he fucks her wet pussy in front of his beautiful assistant, Mrs Barber. Anna Claire loves the feel of his cock […]
Penny Barber may be trying to look innocent in her long floral dress but that hottie is anything but innocent. She loves to show off her stocking-clad legs and tease you with her red panties. Nathan Bronson is ready to fuck this babe and he will cut those panties right off her and stuff them […]
Penny Barber enters the bedroom shared by her stepdaughters, Liz Jordan and Jill Kassidy (who are also stepsisters), so she can gather clothes to do laundry. To her shock, Penny finds a strap-on dildo in the room. Penny is furious and confronts the two girls, demanding to know which of them is the owner of […]
Doctor Barber, an unorthodox therapist, records Elias’ and Penelope’s session, two step-siblings who grew apart due to an incident they can hardly talk about. It seems that they were very close when growing up, but one day, Penelope caught Elias jerking off and their relationship got cold ever since. Doctor Barber suggests trying a mutual […]
Swinger couple Mick & Penny are looking for new property. Being a freaky pair – the property is less important than the real estate agent – as Jasmine finds out when she takes these swingers on as clients. Jasmine tries to remain professional but can’t help herself and decides to get some threesome action with […]
Therapist Penny Barber is meeting with her patient, Kenzie Taylor, and does a Rorschach test as part of the session. But each time Penny shows Kenzie an ink blot, Kenzie mentions seeing women in them. Everything from two women sitting at a cafe to two women kissing! Kenzie doesn’t understand why Penny is showing her […]
Penny Barber, a veteran pageant queen, has been coaching Alexis Tae for a pageant of her own over the last few weeks. The pageant is tomorrow, so they’re doing a dress rehearsal today, with Alexis trying on a stunning green dress for the first time. Penny can hardly believe her eyes- Alexis looks riveting, and […]
All fairytales start the same but don’t always end alike. So the milf Penny Barber did not expect that reading bedtime stories to her stepson would end far from a dream. She could not help but notice how her stepson was fidgeting in bed, obviously dissatisfied with something. When she finished reading, Penny asked what […]
Penny Barber is looking amazing in a tight little dress, and Nathan Bronson is eager to also see her OUT of the dress. But first, he asks Penny how she wants their sexual encounter to start. Penny gives one of her beautiful smiles and says that she’s looking forward to feeling his warmth, and taking […]
Destiny Mira is relaxing in her room when her stepmom, Misty Stone, enters. Misty cheerfully greets her and lets her know that Misty’s book club meeting is about to start. Misty then encourages Destiny to join them, wanting to spend some quality time with her stepdaughter. After some protesting, Destiny begrudgingly agrees and follows after […]
Penny Barber knows it’s wrong, but she wants her stepson Max Fills. She dresses in lingerie that shows off her e-cup tits and then comes up with an excuse to come to Max’s room. She brings him a drink and then apologizes that Max’s dad has grounded him. Upon Max’s request, Penny even brings Max […]
Kylie Rocket is annoyed by her dad’s new girlfriend, especially the way Penny Barber keeps invading her space and leaving messes everywhere, but even she didn’t expect Penny to flash her big tits over the breakfast table! The horny MILF starts touching Kylie as she games, asking if Kylie has a BF… or GF… or […]
Kimmy Kimm and Alison Rey are two film students who have just moved into a new apartment together. Luckily for them, however, their next-door neighbor just happens to be the one and only legendary filmmaker, Penny Barber! Not only has Penny given them a warm welcome to the neighborhood, but she’s also agreed to stop […]
Penny Barber tells her stepdaughter, Chloe Surreal, that she’s going out with some friends. As soon as Penny leaves, Chloe eagerly grabs a dildo she had stashed away to pleasure herself now that she has some alone time. The dildo has a suction cup base, so Chloe sticks the dildo to the floor and rides […]
Penny is the perfect mom, and all of her son’s friends want to taste what she whips up. When one of them gets a moment alone with her, he sees an opportunity to slip his hand in her cookie jar.
A stepmom, Penny Barber, is scolding her stepson, Ricky Spanish, for having been caught looking at nudes on his cell phone at school. Shockingly, however, it’s revealed that the nudes were actually of Penny herself! They have been in a secret relationship together, and thankfully no one recognized her in the photos. If she HAD […]
Penny Barber’s AC is on the fritz, so she has Will the AC repair man stop by to fix it. She’s also hoping he could take care of her wet MILF pussy. Even though Will confesses he’s married and is flattered at her advances, she leaves him with the temptation to join her in the […]
Three stepsisters (Jane Wilde, Maddy May, Maya Woulfe) are shocked by the cost of raising a family and are filled with admiration for their single stepmom, Penny Barber. They express their love and admiration to her and want to give her something special, but they’re not sure what they could possibly offer. After some hesitation, […]
Monica (Penny Barber) and Jared (Robby Apples), a married couple at the peak of their success, are celebrating moving into their new house when they get some horrible news. The cryptocurrency market has crashed, putting their entire livelihoods up in the air. Suddenly, the dream they were living becomes nothing but a neverending nightmare. A […]
Penny Barber is on a little vacation like usual. The only thing different is this time her son’s friend Tyler came along. Lucky for him he’s feeling under the weather and gets to be pampered by his friend’s hot-ass mom. When she proceeds to check his temperature, man o’ man does it start to get […]
As we wrap up the year 2022 we have compiled the hottest, naughtiest mylfs of the year! End the year right and jerk off to stunning mylfs like Bunny Madison, Katie Kush, Penny Barber, Vivianne DeSilva, and more doing what they do best!
Penny Barber paces tentatively through her living room, the beams of midday light from her wooden blinds painting a soft pattern on her skin and dress. She takes out her cell phone and sends a text to Apollo Banks, the young man who runs her paper route. She asks if he can come by, and […]
Hey, TeamSkeet fans! We know you were yearning for this collection, so the wait is over! Join Becky, Harlowe, Julia, and Penny as they get their pussies all wet and dripping. You won’t believe how much these chicks can squirt in this hot compilation.
Kylie Rocket and her girlfriend Lexi Lore are frustrated, because Kylie’s stepmom Penny Barber has a ‘no-closed-door policy’ at the house, making it impossible for Kylie and Lexi to get frisky together. They can’t go to Lexi’s house, because HER parents are even worse… they won’t let Kylie and Lexi be in the same ROOM […]
Every realtor has tricks up her sleeve for selling a hot property. Penny knows appearances are everything, and personally believes it’s good luck to consummate a listing.
Chelsea (Coco Lovelock) arrives at a luxurious house, enviously admiring it while reflecting on how rough her life is right now, especially when it comes to the relationship she has with her parents. She then meets Lydia (Penny Barber) and Anthony (Seth Gamble), a married couple, who warmly invite her inside. Lydia and Anthony begin […]
Penny Barber is visited by Valeria Atreides, who works with her at an LGBTQ+ community center. Valeria says that she wanted to thank Penny for all the work she’s done to help people within the community, especially queer people like themselves — and even MORE for trans people like Valeria. Penny is touched as she […]
Penny Barber has taken her stepson Ricky Spanish to visit family for the weekend. When they arrive, they are greeted by Penny’s stepniece Chloe Surreal, and they all exchange pleasantries. They haven’t had a chance to spend much quality time together, so Chloe is super excited to get to know her stepaunt and stepcousin better […]
Liz and Milf Penny visit the sperm clinic with one goal in mind..to get Liz inseminated with warm man goo. The duo meets with the handsome Doc and proceeds with a very unconventional procedure. They both get so horny they take turns on the docs big cock and she gets a massive creampie under medical […]
Mommy is the most important thing in any girl’s life. A mother gives a girl life, so in return she can give a mother the most precious thing. But this is only in theory. What if Mommy wants to ride on a girl’s boyfriend’s hard cock? What if she wants to take away her daughter’s […]
Blonde teen Krissy Knight gets so horny over her stepmom’s new convertible, she just has to rub herself all over it. She video calls her boyfriend Jimmy Michaels, who rushes right over in time to see her squirt in the car. The teens fuck, but stepmom Penny Barber catches them just as Jimmy cums on […]
What’s up, Mylf lovers? It’s time for another Selects update, so let’s jump right into the fun! We wanted to bring you some of our favorite face-sitting moments for this compilation. When a milf has curves in all the right places and thighs that could knock someone out cold, there’s nothing hotter than her sitting […]
After intense rounds of swap therapy, everything has led up to this – the Von Skeet masquerade! Penny, Jack, Tyler, and Theodora invite Aaliyah, Calvin, Coco, and Josh to their mansion for an orgasmic party. It doesn’t take long for things to get wild, and soon everyone is fucking everyone. Stepbrothers and stepsisters cum together […]
The holiday season brings out the craziness in people, and Tyler, Penny, and Macy are no exception to the rule. Expecting guests, Penny tells Macy she’ll be sharing a room with Tyler. But Macy is not so stoked on the idea as Tyler is obnoxious and is constantly jerking off. When Penny catches Tyler fucking […]
Step-siblings Juan (Loco) and Kyler (Quinn) are in the laundry room, arguing as usual. Her mom Penny Barber married Juan’s dad a year ago, and the kid still doesn’t like hearing Kyler call him “big brother” all the time. The ice breaks as she asks “Why are you looking at me like that?”. “You’re just […]
Dark-haired Penny Barber has invited Van Wylde for a much-needed booty call, but her house guest, Eva Nyx, is proving to be a problem! Blonde Eva is uncontrollably horny and loves to hump the living room furniture. Dominant Penny tells Eva to behave but before she knows it, mischievous Eva is spying on Penny and […]
Penny Barber is helping her stepson, Spikey Dee, practice for a spelling bee he will be competing in shortly. Penny checks the index cards with words provided by the school, and is surprised to see that the first word Spikey has to spell is ‘vulva’. Spikey doesn’t know what that word means, so she explains […]
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 […]
Penny’s emotions were deeply stirred by an intense dream she had last night. She’s a married woman… but we do things in dreams we would never do IRL, right?
Before leaving the house to run some errands, Penny Barber has a word with her two stepdaughters, Aften Opal and Summer Col. She instructs Summer to obey Aften (who is Summer’s older stepsister) while she’s gone. Penny leaves, and Aften goes on a power trip, demanding that Summer do EVERYTHING she says in a clear […]
A silent seduction plays out in plain sight in a 1950’s laundromat.
Jmac was gonna grab some pizza, but his plan changes when he sees a sexy MILF chewing out the valet for giving her car to her ex husband. Penny Barber is too much of a Karen to get a rideshare to pick her up… but she’s got long legs and big tits, so Jmac offers […]
Penny Barber has invited her friend Kendra James over for lunch, but the kitchen is a TOTAL mess! Good thing she’s got her stepson, Jay Romero, to help clean the place up. But when Penny asks Jay to lend some elbow grease, he just groans, complaining that he’s supposed to go hang out with his […]
Stepdaughter Kenzie (Kenzie Reeves) walks past her stepdad (Chad White) swathing TV. She asks him to leave her alone in the house for her online therapy session and ends up going off on him when he pushes her about spending some time together. She apologizes and at the therapy session we find out that she […]
Penny (Barber) is doing the dishes in her kitchen, ear phones on, when her husband Peter (Dick Chibbles) sneaks up behind her -home early from a convention. She rubs her ass against his hard cock, closes her eyes as she lays her head back on his chest, she coo’s “Mmm.. Benny.” The man steps back […]
The Von Skeets are a cunning family and use their prosperity and charm to allure everyone around them. Jack and Penny are the heads of the household and work as psychologists known for their unconventional methods. They have a ravenous appetite for sex and love everything kinky and taboo. Then there is Theodora and Tyler, […]
Stepmom Penny (Barber) caught her son Benny (Juan Loco) in bed with his girlfriend Vicky (Slimthick Vic) -who she hadn’t yet met, and is shocked and hurt that he would have a lover at the end of Part 2. Three months have passed, and Penny laments that her stepson left her for another woman, i.e., […]
“Oh fuck!” That’s all milf Penny Barber can say as you pump your prick in her tight pussy. This gorgeous MILF badly wants and needs your jizz and she’s willing to do whatever it takes to coax it out of you. What it takes is thorough pumping of Penny’s pussy.
Naughty MILF Penny Barber has been playing around on some very sketchy sites lately and it’s made her laptop go haywire, malicious spam and adverts popping up all over the place. Luckily, her stepson is a wiz with computers, but he says this is going to take all day and she can’t even compensate him […]
What’s up, Team Skeet fans? For this Labs update, we’re bringing back a successful experiment, Tales of Taboo. In this episode, orphaned step-siblings Reese and Tyler are 18 and ready to be on their own. But before they can go out on their own, they’ll have to stay with Penny, who is very strict and […]
Armani and Penny put on their sexiest dresses to attract attention tonight, but when Penny gets more than she counted on, Armani’s not sure she can lend a helping hand. Or maybe she’s just afraid neither of them will be able to walk tomorrow…
30-something brunette MILF Penny Barber got stood up by her husband for a planned home-cooked meal, only to turn and find her step-son getting ready to walk out as well. Feeling lonely and neglected, she implores him to stay and enjoy a home-cooked meal with her. When he seems uninterested, she brings on the charm […]
Jerk off to this naughty compilation of hot mylfs such as Charly Hart, Lilith Grace, Cory Chase, Kenzie Love, Penny Barber and more as they suck dick like pros and swallow every last bit of cum!
Ms. Hensley (Penny Barber) asks one of her students, Sandra (Sophia Burns), to stay after class for a brief talk. Sandra says that’s fine, since she doesn’t have cheerleading practice today. Ms. Hensley says that’s actually what she wanted to talk about, because Sandra’s grades have been slipping due to all her cheerleading practices. However, […]
Stepmother, Michelle (Penny Barber), is seen getting ready for cam in a black robe. As she goes live her stepson Billy (Chad Alva) is outside in his car and talking to his girlfriend on his phone about Penny. She is working the room and undressing as the tips come in. The money keeps rolling in […]
Penny drops in to check on her friend, who isn’t home, but her son is – which is exactly what Penny wanted. As she sits on the couch, she stammers through trying to confess her attraction to him and staring at his loose-fitting basketball shorts, then moving in close while rubbing his crotch and getting […]
A shy scientist, Spencer Bradley, who has never put much thought into her appearance, has to present a keynote speech at an upcoming conference, and goes to a fashion designer, Penny Barber, to have an outfit made for the event. As soon as they meet, Penny has eyes for Spencer but tries to remain professional. […]
Ellen (Penny Barber) and her husband Walter (John Strong) are walking through their backyard when they notice a neighbor’s teen, Terry, sneaking around. They are especially curious yet suspicious since Terry soon stops at the home of their troublesome teen neighbor, Gina (Haley Reed). Ellen and Walter watch with growing disgust as Terry nervously knocks […]
Enjoy this compilation of some of the wildest cougars like Caitlin Bell, Penny Barber, Quinn Waters, Victoria June and more riding some young eager cocks!
Jerk off to this compilation of the hottest horny stepmoms such as Aaliyah Love, Dee Williams, Lauren Phillips, Penny Barber and many more!
Enjoy this compilation of the hottest mylfs with the biggest bootys getting fucked into orgasmic oblivion. Featuring Dee Williams, Ivy Lebelle, Penny Barber, Victoria June and more!
Aunt (Penny Barber) is standing in the kitchen, wistfully gazing out the window, when Tyler (Cruise) comes in. “Good morning, sleepyhead”, she greets him. “Mom didn’t tell me you were staying”, he says. “Well, your stepmother has a lot of secrets, but you know that”, she says. “She does?”, he wonders. “How long has she […]
Emily (Laney Grey) nervously enters the office of a youth shelter worker, Donna (Penny Barber). It’s soon revealed that Emily is pregnant but unsure if she will keep it, given that she’s living on the streets. While Donna is caring throughout the conversation, she admits that she and her husband, Alex (John Legendary), are trying […]
After the death of Franco’s father, he and his stepmom Lilly pay a visit to Dr. Barber. While Lilly thinks this visit is to help Franco cope with his sudden loss, Franco addresses the fact that he’s caught Lilly staring at him in the shower– multiple times. With the help of Dr. Barber, Lilly acknowledges […]