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 […]
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!
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, […]
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 […]
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 […]
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. […]
PureTaboo – Haley Reed And Penny Barber – We Warned You Last Time
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 […]
MylfSelects – Victoria June, Penny Barber, Quinn Waters And Caitlin Bell – Cougars Be Hunting
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!
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!
MylfSelects – Victoria June, Ivy Lebelle, Dee Williams And Penny Barber – Big Booty Mylfs
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!
APOVStory – Penny Barber – Your Mom Is A Flirt Part 2
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 […]
PureTaboo – Laney Grey And Penny Barber – Some Ground Rules…
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 […]
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 […]
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 […]
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 […]
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, […]
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.
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 […]
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 […]
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 […]
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, […]
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. […]
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 […]
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 […]
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, […]
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 […]
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” […]
Milfty – Penny Barber – Out Of Touch
When Penny Barber discovers that her stepson Joshua Lewis is using tiktok to watch porn, she realizes her methods of getting into the sexy mood are a bit out of touch so she decides to try and get into tiktok. Joshua catches Penny in the middle of making a tiktok and offers to help her […]
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.
PervTherapy – Jamie Michelle And Penny Barber – Just My Type
Jamie Michelle and Billy Boston visit perv therapist Penny Barber after Billy has been experiencing jealousy issues. As it would turn out, Billy seems to have a thing for his stepmom. Penny suggests they lean hard into the fantasy and experiment a little. The results are better than Jamie and Billy could have hoped for, […]
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 […]
PervMom – Penny Barber – Strict But Fair
Penny Barber is a stepmom who is hard to please, and Billy Boston constantly feels her stinging wrath. When Billy walks out on his chores one day, Penny decides it’s finally time to punish her unruly stepson. But Billy ends up liking the torture, and so to make things right, Penny comes on to Billy […]
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.
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 […]
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 […]
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!
MomSwap – Pristine Edge And Penny Barber – Swappin’ Amish
Penny Barber and Pristine Edge come all the way from the countryside to visit their stepsons, Billy Boston and Joshua Lewis. Once Amish folk, Billy and Joshua are now men of the city, with good times and pussy on the mind. Shocked, Penny and Pristine aren’t sure what to do at first but then hatch […]
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 Selects
Fan favorite pornstar Penny Barber can do no wrong. Her looks and her body are enough to bring anyone to their knees, and she rocks any role she plays on Mylf. That’s why we wanted to dedicate this entire Mylf Selects to showcase some of our favorite Penny Barber moments. Kick back and enjoy the […]
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 […]
MomSwap – Penny Barber And Ashley Wolf – Holier Than Thou
After Tyler Cruise and Joshua Lewis are caught watching pornography at their highly religious school, their stepmoms, Ashley Wolf and Penny Barber, decide to teach them a hard lesson. Using creative techniques, Ashley and Penny want to ensure the two delinquent boys don’t commit the same sin. Though the lesson turns out to be a […]
AllHerLuv – Ariel X, Jade Baker And Penny Barber – Life After Divorce Parts 1-2
Just a few months ago my world was turned upside down when my dad left my stepmom, Ariel. I heard them fighting, daddy was furious and embarrassed that Ariel cheated on him with his own secretary. Ariel cried, apologized, and fell to her knees. I saw a different side to my father that day, and […]
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 […]
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 […]
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 […]
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 […]
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.
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, […]
TeasePOV – Penny Barber – Married Milf Blowjob
AnalMom – Penny Barber – Punished By My Stepmom
Nathan Bronson is a little bit of a delinquent and is at all times getting on the nerves of his stepmom, Penny Barber. At some point, Nathan tries to swipe cash from his stepmom’s room whereas she’s away at work. However when she comes houses unexpectedly, Nathan hides. A lot to Nathan’s shock, Penny begins […]
PureTaboo – Penny Barber – Swapping Sexualities
SCENE OPENS to the doorbell ringing, and Gail (Penny Barber) and her husband Steve (Draven Navarro) eagerly approaching the front door. Before they open the door, they share a quick conspiratorial look. Gail then opens the door, revealing that the person on the other side is Eric (Tony Sting), who is holding a suitcase. They […]
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 […]
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 […]
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 […]
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 […]
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 […]
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 […]
TSPussyHunters – Penny Barber and Jonelle Brooks – Penny Barber Take Anal From Beautiful TS Jonelle Brooks
Penny Barber is meeting with her soon to be ex husband’s attorney to discuss some legal matters. Turns out Penny has been hiding some assets from her husband and the attorney want’s to make sure Penny gets what she deserves. What Penny deserves is a nice hard cock down her throat, in her pussy and […]
BadMilfs – Penny Barber And Aria Carson – Stepmom Knows Best
Aria Carson confides in her stepmom Penny Barber that her 1 year anniversary with her boyfriend Jay Romero is coming up, but she’s not sure if they’ll end up fighting or finally fucking. Penny tells Aria to bring Jay to the bedroom and she’ll take care of the rest. Later, Jay is sitting on Aria’s […]
ShoplyfterMylf – Penny Barber – Holy Mother Of Pearl
When an unassuming milf, Penny Barber, is brought in as a potential shoplifter, loss prevention officer Tommy Gunn looks her over for stolen goods. All seems fine until the cavity search—that’s when Mr. Gunn finds what’s been stolen. There is only one way for Penny to get out of this fiasco.
PervTherapy – Penelope Kay And Penny Barber – The Jealous Stepsister
In this update of PervTherapy, Penny Barber meets Penelope Kay and Anthony Pierce. Penelope and Anthony are in therapy after Penelope shows signs of aggression when Anthony talks to other girls. Penny has a sneaking suspicion that Penelope might be jealous and suggests taking an unconventional therapeutic route. Although the session starts a bit heated, […]
MylfSelects – Natasha Nice, Tia Cyrus, Rachael Cavalli And Penny Barber – Teach a Thing or Two
Who doesn’t love a good lesson now and then? Whip out a notepad and a #2 pencil because you’re going to want to write this down—in this compilation, we’ve gathered the finest stepmom teaching moments around.
PervTherapy – Penny Barber And Syren De Mer – Freudian Slip
Recently, Anthony Peirce has been fantasizing more and more about his stepmom, Syren de Mer. Wanting to get to the bottom of things, Syren suggests she and Anthony see Penny Barber, a therapist. Penny explains that rather than avoid it, Syren and Anthony should embrace the growing sexual tension.
MylfSelects – Crystal Rush, Ivy Lebelle, Brandi Love And Penny Barber – January 2021 Smash Hits
Everyone loves a good milf video, but only the best of the best can hang with this crew. Enjoy this compilation from some of the best milf videos from January of 2021.