MylfLabs – Tristan Summers And Penny Barber – Perv Therapy
What is Perv Therapy? It’s when individuals get sent to therapy to work through their problems and things get sexual with the shrink. In today’s update, stepsiblings Tristan Summers and Jay Romero get sent to do a therapy session with Dr. Penny Barber after their stepmom caught them doing inappropriate things together. Dr. Barber lets […]
Jack Vegas and his stepdaughter Haley Spades go to see therapist Dr. Penny Barber to explore the reason why Haley has a crush on Jack. Dr. Barber encourages them to do a little exercise where they’re allowed to touch each other and explore those feelings further, but Jack feels guilty about it at first. Once […]
Milfty – Penny Barber – Championship Prize
Stepson Jay Romano has been holding off sex for the entire season so he could focus 100% on the game, so when he comes home after winning the championship, he’s pleasantly surprised to find his hot stepmom Penny Barber ready to give him the very special prize that he deserves.
PervDoctor – Penny Barber And Charly Summer – Do It For The Test
When olympic gymnast Charly Summer goes to do a drug test with Dr. Tommy Gunn, the results are brought in by Nurse Penny Barber who tells Charly they came back positive for several illegal substances. Charly begs her to re-do the test, she cannot get caught cheating. Nurse Barber makes her a devious offer, in […]
TeamSkeetLabs – Penny Barber And Reese Robbins – Concept: Tales Of Taboo 2
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 […]
MissaX – Penny Barber – Recovered
Lisa (Penny Barber) gets out of bed gingerly, holding her hip and limping out of the room in pain. Doing the dishes at her kitchen sink she is greeted by her stepson Carl (Nathan Bronson), who asks: “Are you okay?”. “Everything’s fine”, she responds. “How’s your leg?”, he asks. “What leg?”, she jokes. “Mom, there’s […]
MomSwap – Penny Barber And Rachael Cavalli – The Queens Of Cream
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 Cruise in the sales process. Using a special ingredient that only Joshua and Tyler can provide, Penny and Rachael […]
MomSwap – Penny Barber And Aaliyah Love – A Transformative Session: A Deep Analysis Extended Cut
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 […]
Milfty – Penny Barber – Don’t Leave Me
MILF Penny Barber is helping out her step son AJ to get ready to go back to school. After being homeschooled for so long, Penny doesn’t want AJ to leave her alone, so she does everything in her power to convince AJ to stay with her.
TeamSkeetSelects – Gianna Dior, Penny Barber, Tristan Summers And Ashley Wolf – Best Sluts Of 2021
Enjoy this steamy compilation of the naughtiest babes of 2021 featuring gorgeous sluts such as Ashley Wolf, Gianna Dior, Penny Barber, Tristan Summers and more as they get down and dirty in the most sensual ways.
AuntJudysXXX – Penny Barber – In her AJX Debut… 38yo Super-Star MILF Penny Barber Seduces Her Son’s Friend!
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 […]
Transfixed – Penny Barber And Valeria Atreides – Sugar Mentor
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 […]
I hope you are as excited as I am for our little vocabulary study session. I am sure you will get plenty excited once we start and it will be easy to see it in those pants you are wearing. Remember the rule is that for every word you get right Step-Mom will flash you […]
FamiliesTied – Penny Barber And Ivy Lebelle – Cock Crazed Step-Mommy Just Wants Anal For Christmas
Penny Barber is bustling around the house preparing a cookie plate for her thick dicked step-son to get home for Christmas. Her husband is safely scheduled to return a day late, leaving her lots of time to get all her slutty holes filled and get her round ass punished for all her misdeeds this year […]
MylfSelects – Lolly Dames, Penny Barber, Kenzie Taylor And Krissy Lynn – Sloppy Head Compilation
Who doesn’t love a good blow job? Much less when it’s coming from the hottest milfs imaginable! We’ve put together a badass compilation featuring stars like Kenzie Taylornding, Krissy Lynn, Lolly Dames, and Penny Barber, all going down on the luckiest dudes in the world. Enjoy this mashup of some of our favorite “sloppy toppy” […]
TeamSkeetVIP – Deep Analysis: A Swap Movie (2022)
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, […]
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 […]
MylfSelects – Best Of Threesomes Compilation
One hot MILF is plenty, but two is a dream come true. These babes love sharing a thick cock with their sexy friends whenever they get the chance. Beautiful Becky Bandini, Ella Knox, Lauren Phillips, Penny Barber, and more MYLF hotties enjoy sultry group sex in our Best of Threesomes Compilation. The more MILFs the […]
PervTherapy – Kenzie Reeves And Penny Barber – Stepbrother On My Mind
Perv Therapist Penny Barber is back, and this time she’s helping step-siblings Kenzie Reeves and Nathan Bronson get past a recent barrier between the two. Kenzie recently walked in on her stepbrother masturbating, and since then, she can’t get the image out of her head. Penny suggests that instead of running away from the fantasy, […]
Penny Barber had one little problem: her out of control little slut step daughter Mercy West. Using her perfect MILF body and uncontrollable sex appeal to bring Mercy’s punk boyfriend on board for disciplining Mercy, she get’s a little more than she bargained for. After having her juicy round ass spanked a deep red, clamped, […]
FamilyStrokes – Aaliyah Love, Penny Barber, Coco Lovelock And Theodora Day – Masquerade: A Deep Analysis Extended Cut
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 […]
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 […]
PervMom – Penny Barber – A Stepsons Wet Dream
Robby Echo wakes up from a wet dream about his stepmom Penny Barber when she walks in to get him out of bed and realizes what he was hiding under the sheets. Robby is embarrassed but Penny assures him that it’s completely natural and even offers to finish the job and get all that cum […]
MylfOfTheMonth – Penny Barber – Modern Cowgirl 2022
The stunning Penny Barber is Mylf Of The Month for January here at Mylf.com! Dressed in her best cowgirl attire she shares some of her future plans for 2022 before lucky stud Ryan Mclane joins her in bed. Penny will ride Ryan’s cock like the naughtiest cowgirl she is until she gets a delicious creamy […]
ModernDaySins – Spencer Bradley And Penny Barber – Idle Fantasies: Center Of Attention
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. […]
MommysBoy – Penny Barber And Chloe Surreal – Visiting Family
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 […]
FamiliesTied – Penny Barber And Isabella Nice – Tight Bodied Teen Star And Anal Step Mommy Fuck Director’s Huge Cock
Tight bodied teen Isabella Nice is done being managed by her over bearing Step-Mother Penny Barber. Unfortunately for her, she doesn’t know Penny has been using her hot body and slut skills to buy Isabella every role she’s ever had. When the director send Isabella away for wardrobe, Penny is ready to pay him interest […]
APOVStory – Penny Barber – Mommy’s Little White Lies
Stepson (Nathan Bronson) is trying to watch the game with his stepmom (Penny Barber) but gets upset because Penny is chatting away on her phone. She is in a bind though because she has been lying to her friends about a guy she’s dating. The issue being that it is a lie; He thinks she […]
MissaX – Penny Barber – Let Them Talk II Part 1
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 […]
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 […]
PervMom – Penny Barber – Post Porn MILF Bang
When bookish MILF babe Penny Barber gives her stepson a fashion show of the new threads she bought herself, it involves a lot of sultry lingerie and exposed MILF skin. She masturbates while her horny stepson jerks his cock! Later, Penny wants to dive a little deeper into the intimate fun she started the other […]
MylfSelects – Nadia White, Penny Barber And Brooklyn Chase – Two Girls One Cock Compilation
Who doesn’t love a good three-way? At Mylf, we can’t get enough of them, so for this Mylf Selects update, we’ve put together some of the best two-girls-one-cock moments. You’ll see favorites like Penny Barber, Nadia White, Brooklyn Chase, and many more in this perfect new installment.
Jessica and her stepson, Joshua, have been experiencing a lot of tension at home. In search of a solution, the pair sit down with therapist Penny, who tries to figure out what’s going on between them. After asking them to list their favorite qualities about one another, Penny concludes that the built up heat between […]
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 […]
What would happen if four families each contributed one member to create a new family? In this episode of Family Swap, Sera Ryder is looking hot for her Valentine’s Day date. It turns out that her date is swap daddy Clarke Kent. Both Penny Barber and her swap son Ricky Spanish are unhappy with that […]
FamilySinners – Penny Barber – Mothers-In-Law Episode 4
MylfLabs – Penny Barber – Concept: ASMR
By now, you’ve likely heard of “ASMR,” an internet phenomenon that involves sensory stimulation via highly focused audio. Well, people have come to love ASMR worldwide, so MYLF decided it was time to try it out ourselves. Penny Barber plays the seductive nurse in this experiment, and Mike Mancini is the fortunate patient. Through years […]
MissaX – Penny Barber – My Mother The Cam Star
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 […]
TeamSkeetSelects – Becky Bandini, Harlowe Blue, Penny Barber And Julia Robbie – Dripping Pussys Compilation
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.
FuckedAndBound – Penny Barber – Bratty Bitch Beatdown
Penny is no stranger to the pages of this site, and her bratty attitude is something most of us have come to enjoy about her. Derrick, on the other hand puts this smart ass whore in her place quickly. She makes several attempts at trying to push his buttons, yet all it does is get […]
PervTherapy – Maya Farrell And Penny Barber – Building Up Oliver
Stepsiblings Maya Farrell and Oliver Davis visit their therapist Dr. Penny Barber who will try to solve their animosity towards each other. Turns out, even though Maya is always teasing Oliver, this kind of turns him on, so Dr. Barber suggests they explore that further by helping him realize some of his fantasies. After all, […]
MissaX – Kenzie Reeves – In Love With Daddy II
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 […]
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 […]
MomDrips – Penny Barber – Won’t Let Go
Penny Barber has been sleeping with her best friend’s husband for a while now, she wants him to leave her for her, but every time she brings it up he says he feels too bad about it. Penny realizes there’s only one way he’ll finally choose her, so next time they meet, she won’t let […]
APOVStory – Penny Barber – A Day In The Life Part 1
Lila (Vanna Bardot) is always at odds with her horny stepbrother, Jerry (Codey Steele). It’s hard for a young man to think straight with two beautiful women in the house. The other woman he is infatuated with is his very own stepmom, Alex (Penny Barber). Alex is not only his stepmom but his teacher. She […]
Two teens, Sabina Rouge and her friend Haley Reed, are hanging out. Penny Barber, Sabina’s stepmother, pops in and Haley instantly gets a crush on her, although Sabina doesn’t seem to notice. Although Haley subtly tries flirting with Penny, Penny mostly ignores her… and instead seems to be paying attention to Sabina! When Penny excuses […]
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 […]
A cultural exchange student, Holly Day, has been staying with a married couple, Penny Barber and Ken Feels. However, Holly has been behaving badly: always arriving late to the dinner table, nitpicking their cooking, never helping around the house, the list goes on and on. When Penny and Ken confront Holly about this, they say […]
TeamSkeetSelects – Aria Carson, Penny Barber, Dani Blu And Lolly Dames – Babes Riding Dicks
Enjoy this compilation of the hottest babes like Aria Carson, Dani Blu, Lolly Dames, Penny Barber and more as they show off their naughty skills while riding dick like pros!
PureTaboo – Penny Barber And Sophia Burns – Nothing’s Too Good For My Boy
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, […]
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 […]
FuckedAndBound – Penny Barber – Sexy MILF is Milked and Fucked
Penny is back and hotter than ever. She is led in by Mr. Mod wearing a cow bell and put on display then he makes her milk her lactating tits. This horny slut is face fucked and then tied standing for her cunt to get pounded hard and fast. Next her ass is the center […]
AnimeshinClub – Hentai Sex School – 2nd Semester – Episode 5 – Track & Field
It’s the fourth & final round in the coveted 4Play Games which will decide the winner with Hentai Sex School facing off against Thrustwell Academy. Tensions are at an all-time high as Nathan, Penny, Misty, and Blitz face off against Preston and his elite team. Although Preston tries to get in their heads, Nathan and […]
MommysBoy – Penny Barber – Be Polite To Our Guest, Young Man!
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 […]
MomWantsCreampie – Penny Barber – My Stepmom Really Cares
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 […]
StayHomeMilf – Penny Barber – Perfect Roommate For The Job
Hot MILF Penny Barber is quarantining with Filthy Rich during the pandemic, since they both make dirty videos to earn money, they are the perfect roommates to help each other out. Filthy convinces Penny to assist him with his latest POV video and she’s more than happy to do so.
APOVStory – Vanna Bardot – A Day In The Life Part 2
Lila (Vanna Bardot) begins to think twice about how hard she’s been on her snoopy stepbrother, Jerry (Codey Steele). She walks into his bedroom to make peace with him, but the truth is, that she likes the attention he gives her. It makes her feel special, beautiful, and wanted.. and she wonders how wonderful it […]
PervTherapy – Lilly James And Penny Barber – Sexual Beings
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 […]
MomsBangTeens – Penny Barber And Krissy Knight – Car Squirter Makes Nice With Mean MILF Threesome
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 […]
Melody Marks did not expect to spend this Christmas alone with her stepbrother. Their stepparents went on a trip, and now they have to entertain themselves. Maybe gifts set by the fireplace will somehow fix this awkward evening? And Melody couldn’t imagine that her stepbrother’s present is trendy lace lingerie. Only someone special could choose […]
MomSwap – Jessica Ryan And Penny Barber – Stepmommy Pies
Busty stepmoms Jessica Ryan and Penny Barber have been catching their respective stepsons Anthony Pierce and Tyler Cruise jerking off excessively, but when they see them fucking the pies they had just baked, that is the last straw. The stepmoms tell them off first, demanding an apology, but then they decide to give them a […]
FreeUseMILF – Penny Barber, Aria Carson And Lyra Lockhart – Polygamy
Aria Carson, Lyra Lockhart and Penny Barber are the three chosen wives of lucky stud Calvin Hardy, who demands full access to their bodies throughout the whole day! The three wives will suck on Calvin’s cock and get pounded as hard and as often as he pleases and they’re all happy to thoroughly pleasure their […]
MylfSelects – Penny Barber, Charley Hart, Kiki Klout And Bunny Madison – Mylf Swallows Compilation
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!
MyYoungerLover – Penny Barber – Paper Route
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 […]