PervTherapy – Sophia Burns And Penny Barber – Alex Says
Perv Therapist Penny Barber is back, and this time she’ll be helping stepsiblings, Alex Jett and Sophia Burns. Alex has confidence issues, but Sohpia seems to be blooming and is happy to boss Alex around, making him pleasure all her sexual desires on a whim. Penny suggests the duo try role reversal to increase Alex’s […]
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 catches her stepdaughter, Naudi Nala, getting naughty with her English teacher, Marcus London. At first, she is absolutely livid, but Penny wants some “English lessons” herself after seeing Marcus’s talents. Soon after, Penny makes a proposition with Marcus, and if he wants to buy Penny’s silence, he’ll get Naudi into a good school […]
ManyVids – Penny Barber – Mommy’s Your GF For Christmas
What would you like for Christmas this year, sweetie? A girlfriend!? Well those can be difficult to wrap, so don’t get your hopes up. I finish my umteenth cup of special eggnog, and go back to laying out holiday decorations. Later, you come into my bedroom after I call you. Mommy’s wearing nothing but a […]
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, […]
MILFY – Penny Barber – Tasty MILF Is Hungry For Young Studs Cock
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.
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 […]
LezBeBad – Dana Vespoli And Penny Barber – Parole My Hole
You’d think someone on house arrest would be terrified of their parole officer coming around. But when it comes to Dana Vespoli, she absolutely loves it. You see, Dana and her parole officer, Penny Barber, have a special arrangement… Dana ‘steps’ outside of the perimeter of her home, her ankle bracelet goes off, and then […]
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 […]
After Naudi is caught shoplifting, she is reprimanded and brought into the back office for interrogation. Marcus has difficulty getting information from the young thief, so loss prevention officer Penny offers a helping hand. Now, if Naudi wants to avoid serious punishment, she’ll do whatever Penny tells her.
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 […]
Penny Barber has invited her old friend, Lexi Luna, over to her house to catch up. It’s been ages since they’ve seen each other, so they have LOTS to talk about. After making themselves comfortable in the living room, they start dishing out all the hot gossip that they’ve amassed over the last few years. […]
AuntJudysXXX – Penny Barber – Penny Gets Stood Up, Gives Her Step-Son Incentive To Stay For Dinner
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 […]
Mylfwood – Penny Barber – Nurse Ratched
When Dr. Jack Vegas tells Nurse Ratched (played by Penny Barber) about how dangerous their patient Giovanni Francesco is, she begs him not to sentence him to fry in the electric chair. Dr. Vegas explains that it’s the safest thing to do so Nurse Ratched attempts to connect with Giovanni one more time… except the […]
Penny Barber is a pissed off ex-wife who needs a little relief from battling her husband and his lawyers all day. A message will do the trick! Vince Karter’s strong hands are almost the touch she needs, oiled up and horny Penny is in the mood for something more. What would be better than a […]
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 […]
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 […]
Deeper – Penny Barber – Tumble
A silent seduction plays out in plain sight in a 1950’s laundromat.
The Pussy Platoon is in full on the Upper Floor for this once a year blow-out slave review orgy. When nine trained Upper Floor slaves stand at attention, waiting to be inspected by the Steward and Mr. Acworth, the room stands still with anticipation until the order is given – ‘Get the Dicks Hard!” and […]
PervTherapy – Penny Barber And April Olsen – A Supportive Stepdad
Dr. Penny Barber sees April Olsen and her stepdad Dan Ferrari who feel sexually uncomfortable about April wanting to be an influencer and posting naughty pictures online to do so. After a few minutes with Dr. Barber, Dan agrees to do an exercise in which April will show how she takes pictures while he tries […]
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. […]
IHaveAWife – Penny Barber 32057: Penny Barber Wants The Married AC Repair Man To Check Her Temperature
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 […]
Clips4Sale – PrimalsMentalDomination – Penny Barber – Training His Lazy Bitch Coworker
The office is on minimum staff for another few months until it’s declared everyone can go back to work. Michael was selected to be one of the only two people to keep working in the office since he is the most productive and trustworthy employee in the company. However his coworker Penny was also picked […]
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 […]
MylfSelects – Penny Barber, Dee Williams, Crystal Rush And Lauren Phillips – Ultimate Butt Sluts
MYLF fans! Are you ready for another Selects update? Great, because we’re focusing on the Anal Mom series this time. These mature babes love taking it up the butt and showing off just how talented they are. You will see faces you love, such as Crystal Rush, Dee Williams, Lauren Phillips, and Penny Barber. You […]
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 […]
Security officer Rusty Nails brings suspected thief Serena Santos into the backroom for questioning when his partner Officer Penny Barber decides to join in the interrogation. Serena swears she has nowhere to hide any merchandise so Officer Penny proceeds to submit her to a strip search in which they find an expensive watch hiding in […]
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 […]
PervTherapy – Minxx Marley And Penny Barber – A Man Like Me
As Minxx Marley gets ready to leave for college, she and Rusty visit Dr. Penny Barber, who finds Rusty is jealous about how many new guys Minxx will meet in this new phase of her life, wishing she can find a man like him. To help, the doctor suggests sexual expression to solve possessive feelings. […]
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 […]
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 […]
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 […]
FamilySinners – Penny Barber – Peeping Tom
Jenny (Penny Barber) starts to feel as though she’s being watched as she gets changed and when she sees her stepson (Dante Colle) in the other room, he’s suspiciously out of breath. She decides to catch him red-handed and confronts him about his voyeuristic tendencies.
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 […]
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 […]
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 […]
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 […]
UPCLOSE – Penny Barber – Up Close With Penny Barber
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 […]
MommysGirl – Jane Wilde, Maya Woulfe, Penny Barber And Maddy May – Our Way Of Saying Thanks
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, […]
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 […]
AuntJudysXXX – Penny Barber – Penny Barber Enlists Her Stepson For Computer Help, Gets A Creampie As Well
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 […]
Captain Warren (Penny Barber) is on the warpath after the jailbreak, and Officers Bishop (Nicole Kitt) and Jones (Alex Jones) are the first targets for her wrath, but when a ransom video from Gibbs arrives, it’s all hands on deck. Warren wants to ensure Bishop and Jones are going to be team players, so she […]
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 […]
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.
MilfAF – Penny Barber – MILF Penny Barber Got Impaled – Mylf POV
“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.
MommysGirl – Aften Opal, Penny Barber And Summer Col – Your Stepsister’s In Charge
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 […]
TheUpperFloor – Moka Mora And Penny Barber – Hot Spoiled Princess & Anal Step-Mommy Earn Their Keep
Curvy Mommy Penny Barber is busy cleaning the house for long lost Uncle Ramon’s arrival and scolding her hot little piece-of-ass step-daughter for being a brat. Both ladies think that uncle Ramon is simply visiting to straighten out a small mistake in the will, not knowing that his brother did actually leave him everything, including […]
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 – Aaliyah Love, Lauren Phillips, Dee Williams And Penny Barber – Hottest Horny Stepmoms
Jerk off to this compilation of the hottest horny stepmoms such as Aaliyah Love, Dee Williams, Lauren Phillips, Penny Barber and many more!
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 […]
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 […]
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.
UPCLOSE – Penny Barber – Call Me Mommy
In this week’s episode, Bree Mills interviews retired wrestler and AVN MILF Performer of the Year (2024) Penny Barber! Penny discusses her early fascination with power dynamics and fetishism, influenced by pop culture like the 2002 film ‘Secretary’, and early Disney movies! Bree and Penny reflect on how to reckon with the personal identity & […]
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.
TeamSkeetSelects – Alura Jensen, Crystal Rush, Becky Bandini And Penny Barber – The Best of Bad Milfs
Everyone loves a milf, so for this Team Skeets Selects update, we’ve put together some of our favorite Bad Milf moments. You won’t want to miss out on this ultra star-studded compilation, filled with the hottest mature women and their young counterparts getting fucked hard.
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 […]
MilfBody – Penny Barber – Tricky Poses
Penny Barber starts doing her yoga routine, making sure she hits all the poses to keep her body good and stretched. After she’s done with the basics, yoga instructor Sterling Cooper joins in to help adjust some of the trickier poses. Soon, Penny will put her flexibility to good use.
MylfSelects – Lily Lane, London River, Ivy Lebelle And Penny Barber – A Better Man Compilation
Being a bad boy can also be tricky because you never know when you’ll get a horny MYLF to correct your naughty ways. So we’ve put together an excellent compilation of some of the hottest, kinkiest attempts to turn these guys around. From Lilly Jane to London River and Ivy Lebelle, don’t miss out on […]
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 […]
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.
MilfBody – Penny Barber – Better Late Than Never
Will is late to his workout with the steaming hot Penny. She’s mad, but not so mad that she isn’t happy to see him. The two get to work, and Penny wants Will to see how all of her work in the gym has paid off. She’s horny for him, and she isn’t shy about […]
MylfSelects – Armani Black, Carmela Clutch, Penny Barber And Lauren Phillips – Our February MYLFs
What’s up, TeamSkeet fans? Who doesn’t enjoy watching a hot, horny MILF ride a big dick and orgasm? Well, prepare to be amazed. As February comes to an end, as usual, we’ve thrown together some of our favorite MYLF moments of the month, with spectacular scenes including Penny Barber, Aila Donovan, Lauren Phillips, Carmela Clutch, […]
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 […]
MommysGirl – Misty Stone, Penny Barber, Jennifer White And Destiny Mira – Book Club Sapphic Seduction
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 […]