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Penny Barber 312

Penny Barber is a 41-year-old actress from United States | See her IAFD Profile, Babepedia page or follow her on Twitter(X)

Penny Barber's Newest Videos | Popular Videos

Team Skeet Selects - Perfect Bodies

Vixi Rafi, Isabella Jules, Odessa, Violet Voss, Lucy Foxxx, Selina Imai, Ellie Nova, Madison Wilde, Fiona Frost, Penelope Woods, Blake Blossom, Leah Gotti & Penny Barber - Compilation: Perfect Bodies
Released: July 9, 2025

Whether she’s petite and perky or busty with hips to die for, these beautiful creatures have one thing in common: they’re all horny as fuck. This incredible compilation has some of the hottest women in the world begging for dick and even some pussy too! Redheads, brunettes and blondes, MILFS and Teens, but above all, desperately horny sluts. Don’t miss this ball-draining compilation, featuring Ellie Nova, Blake Blossom, Shay Sights, Leah Gotti, Madison Wilde, Penny Barber, Lucy Foxx, and more!

Divine Bitches - Penny Barber

Penny Barber - Mommy’s Cock-Hungry Hole
Released: July 3, 2025

The magnificent Penny Barber has found a bound Max Mabry, an eager and compliant sub, tied to a St. Andrew’s cross. Penny uses a cane on his sensitive skin, hitting his legs repeatedly. She uses a crop on him and he yells and writhes in his bondage. Penny licks his nipples and his cock through his lace underwear. In scene, Max is bound on his back with a leg suspended as Penny uses a strap-on dildo to fuck his mouth. She licks and finger-fucks his hole and plows him with the dildo. As Penny fucks Max she fingers herself to cum and squirts over his hole. When Penny cums again she squats over Max’s chest, squirts on his chest and feeds him her juices...

Moms Teach Sex - Penny Barber

Penny Barber - Teaching My Stepson How Not To Be A Cuck - S24:E2
Released: June 30, 2025

Penny Barber is cleaning her bedroom when she finds a cell phone under the bed. She realizes that her husband has been fucking his intern and recording it on a burner phone. To get even, Penny calls a family meeting where she seduces her stepson, Max Fills while her husband watches.

Team Skeet Selects - Compilation: Suck It Then Fuck It

Christy Love, Penny Barber, Clara Trinity, Naudi Nala, Sia Wood, Jill Taylor, Charlie Forde, Nicole Nichols, Ivy Ireland, Katerina Deville, Addyson James, Nikki Slick, Shelena, Mckenzie Mae & Ali Jones - Compilation: Suck It Then Fuck It
Released: June 5, 2025

"Are you ready for a big, hard dick inside you?" These women are always ready, and they'll suck it first every time. Even when they're handling two cocks at once, they'll make sure to shove both in their mouth before they get fucked. Sometimes, they'll even get pounded while sucking another guy's dick. Then, they'll lend out their pussies and asses, and ride those cocks, but one thing is for certain: they'll do anything to send everyone's dicks home completely dry.

Missa X - Penny Barber

Penny Barber - An Impossible Love
Released: May 6, 2025

Penny Barber is busy doing the dishes at her kitchen sink when stepson Jared (Ricky Spanish) sneaks up behind her. "Thomas!" she exclaims and starts grinding her ass against him, until she turns around and is shocked to see it's not his dad,Thomas, but her stepson instead!

Mylfwood - Penny Barber

Penny Barber - 50 Shades of Milf
Released: May 29, 2025

Ana (Penny Barber) was so excited to become Mr. Gray’s (Ken Feels) new assistant. A partner of Ana’s dad, Mr. Gray’s success was surrounded by a mysterious air that captivated Ana. One day, Mr. Gray invited Ana to his home and showed her around the place so she could get familiar with his daily routine. Suddenly, they came across a secret room. When Mr. Gray opened the door, Ana noticed kinky leather objects all over the place and trembled. Was Mr. Gray a sadist? The successful businessman soothed the lovely lady by explaining that he was a dominant. His true desire was for Ana to submit to him fully. Ana’s fears suddenly evolved into something different–a kinky rush of curiosity and excitement. She was no longer interested in learning about Mr. Gray’s corporate success. She now wanted to understand this mysterious man’s world of pleasure, and submit to his deepest and darkest desires…

Mommy’s Boy - Ryan Keely & Penny Barber

Ryan Keely & Penny Barber - Penny's Fucking 40
Released: May 24, 2025

It's Penny Barber's 40th birthday and her best friend, Ryan Keely, is about to take her out for a night of fun to celebrate. But when Ryan sees how... modest... Penny's outfit is, she's unimpressed. Now that Penny's a MILF, she has to dress the part, which is when Ryan gifts her a sexy form-fitting dress to wear instead. Although Penny's flustered, she gives in and tries it on.

Oops Family - Penny Barber

Penny Barber - Stepmom got busted
Released: May 16, 2025

Stunning MILF Penny Barber drives young guys wild with her curvy body and massive, jaw-dropping tits. Even her stepson can’t stop ogling the big-ass, juicy stepmom. But when he returns from the police academy, he notices her expensive outfit — highlighting her fantastic rack but clearly out of her budget. Turns out, the horny shoplifting stepmom steals clothes to flaunt her sexy curves and make guys’ cocks rock-hard. The rookie cop stepson won’t tolerate crime at home, so he cuffs the busty seductress to keep her from fleeing the scene.

Team Skeet Selects - They’re Horny, They’re Pervy, and They’re in Control

Penny Barber, Samantha Reigns, Penelope Woods, River Lynn, Shay Sights, Tommy King, Sonny Mckinley, Emma Rosie, Mochi Mona, Sophia Sterling, Kelly Caprice, Bad Bella, Charlotte Mae, Daisy Pheonix, Delilah Dagger, Clemence Audiard & Arina Shy - They’re Horny, They’re Pervy, and They’re in Control
Released: April 20, 2025

Knowing what you want is hot, and having the power to get it is even hotter. Whether it is a horny principal, a security guard who can promise to get anyone out of trouble, a therapist who can’t keep their eyes away from their client’s tits, or a masseur who wants to massage every inch of their client’s body, if they’re pervy enough, we all need them. There’s nothing better for a submissive teen or a hot milf than a horny power figure who is desperate to take care of their bodies, fucking them until everyone can hear their moans and teaching them how wild and dirty fantasies can get.

Slayed - Penny Barber & Phoenix Marie

Penny Barber & Phoenix Marie - MILF Phoenix Rides Pussy-Hungry Pennys Face
Released: April 15, 2025

Two statuesque MILFS, one bed full of cash. When Penny and Phoenix party, the thrills don't come cheap, but they do come often.

RK Prime - Hime Marie & Penny Barber

Hime Marie & Penny Barber - Steamy Towel Girl Threesome
Released: March 23, 2025

Hot MILF Penny Barber is enjoying the sauna naked, until Mick Blue walks in on her. Penny covers back up... but only for a little while. She flaunts her hot body as she pours water over her tits and ass, enticing Mick to eat her pussy. As the pair are fucking, horny towel girl Hime Marie peeks in at them... and gets caught! The MILF and the silver fox undress the teen and let her join them for a very steamy threesome, as the women lick each other and take Mick's big cock, sharing his load.

Brazzers Exxtra - Penny Barber

Penny Barber - Horny MILF In The Wild
Released: March 13, 2025

Penny Barber is so horny she masturbates in her car, hoping nobody will catch her. But it’s not long before college bro Damion walks by and sees the hot MILF rubbing her pussy, and he can’t resist filming her with his phone. Horny and annoyed, she scolds him and tells him to get her in her car – after all, a dick will make her come harder than her hand.

Mylf Labs - Penny Barber

Penny Barber - Virgin Mommy
Released: March 6, 2025

I didn't use to be like this. Until a few days ago, I was a virgin. Sex wasn't something I obsessed over until he showed up. It all started when I rented out my spare room to a student. Week after week, He brought chicks home, and I heard everything. I was jealous, always thinking: "Why can't that be me?". Every morning, he paraded himself in nothing but his underwear. There was only one thought I couldn't shake, and then it happened. He knew I wanted him, and he refused to wait any longer. For the first time, I felt like a woman.

Mom Swap - Penny Barber & Shay Sights

Penny Barber & Shay Sights - Our Stepsons Are Embarrassing Us! Only a Foursome Can Help
Released: February 23, 2025

Politics are hard! I've been working on my campaign nonstop, and now, since my stepson was seen by several pedestrians sniffing panties, people think that he's a perv, and the voters' opinions of me are changing. Just when I thought all was lost, my rival's stepson was caught humping every unanimated object he could find. Our campaigns are our priority, so we've decided to call a truce until we figure out what to do with our stepsons. If they're both overly sexual, there's only one way to deal with them, and it will require spanking, a few blowjobs, and a foursome to get all their urges out. Hopefully, two wet pussies will be enough for them to stop embarrassing us.

Girls Way - Penny Barber, August Skye & Lana Smalls

Penny Barber, August Skye & Lana Smalls - Supernaturally Stacked: Dove Plea
Released: February 20, 2025

August Skye and Lana Smalls are packing up boxes one day when they stumble upon their old spirit board. They're absolutely ticked pink as they start recounting old memories of when they used to tempt the spirits with their supernatural shenanigans. That's when one of them gets the idea to go back to their old haunt (and the place where they had their first kiss)... Placard Manor!

When they arrive at Placard Manor, it's just as dark and cobwebby as they remember it. They find the perfect spot and bust open the spirit board, ready for some giggles and chills. What they end up getting, however, is something much more real... and ghostly, than they ever could imagine. Penny Barber, a resident spirit of Placard Manor, shows up, and she's only got one thing on her mind...

Pure Taboo - Kenna James & Penny Barber

Kenna James & Penny Barber - Not Again
Released: February 11, 2025

Rachel (Kenna James) is happily married to Tye (Chad Alva). However, Rachel wonders why Tye has kept her away from his stepmom Amy (Penny Barber) and his other parent Josh (Charles Dera). Rachel has never met or spoken to them after years of dating Tye, and he even refused to invite them to their wedding.

One day, Rachel receives a phone call from Amy saying that she and Josh happen to be coming to town, so Rachel decides to be polite and invite them to stay here instead of going to a hotel. When Tye finds out, he gets upset at the idea of his parents staying over. Rachel is confused and asks why - his parents sound nice! Tye doesn't want to explain, but begrudgingly says that Rachel doesn't have to cancel the invitation to his parents, so Rachel drops the subject.

Missa X - Penny Barber

Penny Barber - The Storm
Released: January 8, 2025

Kyle (Ricky Spanish) and his new stepmother Penny Barber are trapped at home while his dad's away. with the town suffering a blackout power shortage as a storm rages locally. They try to be optimistic but as Penny admits, "It's apocalyptic".

Bundled up to try and keep warm in the cold house for a second night without power, the two of them try to keep up their spirits, with Kyle haltingly telling a "stepmom joke." The joke is cute, albeit, sexual. Penny can't help but laugh at a joke that's terrible. She admits, "At least it made me forget the cold for a second".

Elegant Angel - Penny Barber, Reagan Foxx, Ryan Keely & Shay Sights

Penny Barber, Reagan Foxx, Ryan Keely & Shay Sights - 4 MILFs 1 Cock
Released: January 19, 2025

Adult Time - Penny Barber

Penny Barber - Knows The Drill
Released: January 9, 2025

Penny Barber is standing tall and proud, wearing a tight black skirt, revealing white blouse, and heart-shaped earrings. She's immediately hungry for attention, unafraid to talk dirty as she removes her top and shows off her amazing tits. Then she slips off her skirt, showing off her sexy black panties beneath. Even though she encourages Ryan Driller to jerk off the whole time to get ready for her, she still wants him -- and you -- to follow her instructions closely. And NO ONE is allowed to cum until she says so!

Divine Bitches - Penny Barber

Penny Barber - Fuck Around and Find Out
Released: January 1, 2025

Sage Roux is back for more punishment and domination from a beautiful woman. Today, sensual and commanding Penny Barber is the Divine Bitch who will try to break Sage and give him extreme pleasure beyond his wildest dreams. Sage is on his knees tied to a headboard as Penny inspects her toy. She canes his sensitive feet and ass leaving bright red slash marks across his flesh and then pinches clothespins all over Sage’s balls before slapping them off.

Penny Barber - Pornstar Collection

UPDATED Penny Barber Mega Collection
313 Videos | 400 GB

Penny Barber (aka Penny/Penney Play, born May 24, 1985) is an San Francisco-based American porn star and bondage model. Barber has filmed for Twisted Factory, Kink and also produces her own films. Barber's productions feature elements of femdom, sissification and ageplay. She has also written and published a book on the subject of age play and diaper fetishism titled The Age Play and Diaper Fetish Handbook.

Anal Arrangement

Cast: Cherry Kiss, Lauren Phillips, Penny Barber, Siri Dahl

Oops Family - Penny Barber & Melody Marks

Penny Barber & Melody Marks - It’s Time For Christmas Orgy
Released: December 20, 2024

Christmas is already on the threshold, so gorgeous MILF Penny Barber alongside her husband invite stepdaughter Melody Marks and stepson for the family celebration. The stepmother suggests everyone decorate the Christmas tree. While the stepson is doodling, his stepsister works hard on this task. But at one moment, the guy notices something that gets his attention. Lovely Melody forgot to put on her panties when she was changing clothes. And now the stepsister's juicy pussy appears in front of the guy's eyes, so his hands are already reaching out for this wonderful gift.

MiLFUCKD - Penny Barber

Penny Barber - Boss Seduces Her Eager Young Intern
Released: December 7, 2024

After climbing to the top of the corporate ladder, Penny finds that she has everything she ever wanted. One of the perks of being the boss is getting access to a new eager intern, who is willing to go above and beyond to make sure his boss is pleased

Adult Time Switch - Codi Vore & Penny Barber

Codi Vore & Penny Barber - Switch: Breathless
Released: November 30, 2024

Codi Vore agreed to go on a hike in the woods with her friend Penny Barber, knowing it would be a fun-filled adventure. Since Penny was an environmentalist, Codi figured she'd learn a thing or two from her about nature. But little did Codi know, she'd learn a thing or two about her OWN nature as well.

Whipped Ass - Ashley Lane & Penny Barber

Ashley Lane & Penny Barber - Penny Trains Pet, Ashley
Released: November 27, 2024

Penny Barber and Ashley Lane are no strangers to BDSM and when they get together for Kink.com the sparks literally fly! For starters Ashley is Penny’s pet bauble, chained to a metal cot with a dog’s water bowl beside it. Mommy Penny wants to see just how dirty her pet is so she tries out her new toys starting with a suede flogger, then the cane, to Ashley’s ass. Next Penny tests Ashley’s pussy and declares that hole is good and used but could be used even more. Next Ashley is bound to the cot face up while Penny dangles some clothespins on a string in her face. After applying the pins to Ashley’s nipples Penny gets a big studded and starts working it one stud at a time into Ashley’s pussy. Penny then applies a zipper of clothespins across Ashley’s tits then yanks it off as she uses the Hitachi on her pets pussy, and then Penny gets the Zapper on Ashley a bit. Finally Penny has put on a strap-on and has per pet Ashley suck it like the dirty girl she is, doing such a good job that Penny has her mount the dong and ride her Mommy to climax. At last Penney wants her piece of Ashley’s ass and bends her over the chair, before squirting all over her sexy little pet!

Mom Swap - Penny Barber & Charlie Forde

Penny Barber & Charlie Forde - NNN Challenge Day 21: Cum Inside, Make Mommy a Mommy
Released: November 21, 2024

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.

MILF Dreams

Cast: Jessica Ryan, Penny Barber, Rachael Cavalli, Reagan Foxx

Elegant Angel - Penny Barber

Penny Barber - Bed and Breakfast
Released: November 13, 2024

Anatomik Media - Laney Grey & Penny Barber

Laney Grey & Penny Barber - Dinner Scene
Released: August 26, 2024

Pure Taboo - Penny Barber

Penny Barber - Future Darkly: Virtual Immorality
Released: October 31, 2024

A widow, Lilah (Penny Barber), says goodbye to her stepson Darryl (Max Fills), who is going back to college after a period of mourning. As the weeks go by, Lilah feels lonelier than ever without Darryl in the house. She becomes desperate for intimacy and connection, so her friend Justine suggests trying A.I. companionship.

Lilah goes down the rabbit hole of exploring technological innovations to stimulate herself emotionally and physically, including an A.I. who takes the form of Darryl that she eventually falls for. By the time the real Darryl comes back home for a visit, she is hopelessly obsessed with this virtual fantasy - and the only way he can pull her back to reality is by offering her a real-world version of the taboo relationship she's become dependent on.

MILFY - Penny Barber

Penny Barber - Domme Mommy Penny Barber Punishes Boy Toy While Hubbys At Work
Released: October 30, 2024

Penny's husband can't loosen up, so she recruits a boy toy who will let her take charge. This wife knows what she wants, and cheating is the least of what she'll do to get it.

Mylf Selects - Swap My Stepmom

Jessica Ryan, Miss Raquel, Silvia Saige, Carmen Valentina, Lilly Hall, Crystal Rush, Brandi Love, Ryan Keely, Penny Barber, Bunny Madison, Crystal Clark, Katrina Colt, Millie Morgan, Lindsey Lakes, Angel Wave, Alaina Taylor, Justine Jakobs, Savvy Suxx, Selina Imai, Ebony Mystique & Annie King - Swap My Stepmom
Released: October 24, 2024

Do stepmoms love to swap? Uh, fuck yeah, they do! If you’ve been with us a while, you know swapping is always on the menu. If you’re new here, strap the fuck in because we’re constantly swapping moms. The stepmoms around here are always teaching valuable lessons, showing their stepsons how to pleasure a woman’s pussy and how to bring her to crazy squirting orgasms. This compilation features some of our favorite stepmom-swapping moments and showcases all of your favorite horny milfs. You won’t want to miss a single second of these mature bombshells getting sexual and playing with forbidden fruit. Big tits, the juiciest asses, and sloshing wet pussies await you in this Selects scene!

Missa X - Penny Barber

Penny Barber - Behind Dad's Back
Released: October 12, 2024

What happens when a stepmother is sexually attracted to her son? Stepmother Penny Barber, is so attracted to her stepson, Derrick (Parker Ambrose), that her husband is taking notice. She must not lead him on, she tells herself. She must try to be a NORMAL stepmother. My god.. how should one act when he comes downstairs with his youthful but masculine chest exposed? She criticizes him for appearing shirtless, and sends him back upstairs to dress properly, claiming what would his dad think if he came home (already left for work) and saw him like that?

Family Swap - Penny Barber & Sky Wonderland

Penny Barber & Sky Wonderland - Swap Family Halloween Boxes - S9:E8
Released: October 7, 2024

What would happen if four families each contributed one member to create a new family? In this episode of Family Swap, Sky Wonderland and her swap bro Parker Ambrose are making scary boxes. Their swap parents, Penny Barber and Will Pounder, get drawn into the argument. Will takes Sky's side while Penny takes Parker's.

Brazzers Exxtra - Penny Barber & Kell Fire

Penny Barber & Kell Fire - Two For Tennis Three For Fucking
Released: October 3, 2024

Van Wylde goes crazy for his girlfriend (Penny Barber) when she wears her cute tennis outfit. When Penny's friend (Kell Fire) comes over wearing a matching outfit, Van finds himself horny and confused, accidentally fucking Kell from behind while she's looking through the fridge. Penny catches them, which leads to lesbian sex and a hot threesome. That tennis tournament can wait.

Girls Way - Come Out to Play: An All-Girl Warriors Parody

Jane Wilde, Little Puck, Leana Lovings, Codi Vore, Hailey Rose, Lulu Chu, Penny Barber, Ana Foxxx, Casey Calvert & Serene Siren - Come Out to Play: An All-Girl Warriors Parody
Released: October 3, 2024

A DJ (Ana Foxxx)'s voice echoes through the grimy cityscape of alleys and buildings, creating an atmosphere of tension and anticipation. Her voice is charismatic, smooth, and authoritative as she speaks into her microphone from where she sits in her little red booth.

The DJ announces that two all-girl gangs are about to have the clash of a lifetime. One of the gangs is led by the fierce and fearless Raven (Little Puck), who is ready to whip everyone into submission as she leads her girls (Codi Vore, Lulu Chu, Hailey Rose) into battle. The other gang is led by the bold and brilliant Blaze (Serene Siren), who is ready to crush the competition with her girls (Casey Calvert, Jane Wilde, Leana Lovings). Both of these sexy gangs are filled with femmes who are ready to throw down and show the city what they're made of!

Missa X - New 2024 Updates

Rachael Cavalli - Heartburn pt. 1
Kenzie Taylor - When Dad Is Away II
Penny Barber - Behind Dad's Back
Aubree Valentine - Challenge or Fail
Brooke Barclays - Playing in the Pocket
Dana Vespoli - Dear Annie
Cherry Kiss - We're a Team
Mina Luxx - Private Dick

In Part 1 of the "Heartburn" saga, we're introduced to several of the characters, after a brief tease of the sexual action (and infidelity) in store.
Rachel (Olive Glass) is a housewife who is going back to college to study and become a professor, while earning some money of her own tutoring. Her husband George (Ryan Driller) is somewhat stifling to her ambition, sending her off on an errand to get his car fixed, even though she's busy trying to write. They're planning a weekend getaway but the busted car is one roadblock...

Mylf Selects - Milfs Training Compilation

Sofie Marie, Penny Barber, Sophia Locke, Bianca Burke, Cassie Del Isla, Payton Preslee, Crystal Clark, Sage Rabbit, Kat Marie, Mayara Lopes, Blaire Johnson, Monica Lush, Kelly Caprice & Miss Flora - Milfs Training Compilation
Released: September 26, 2024

What’s up, MYLF lovers? You can’t get enough of our roster of milfs, and we love serving you the wildest and kinkiest compilations. Selects is all about putting together niche moments focused on a specific kink. This time, we’re celebrating training milfs, because everyone loves a fit mama. Whether she’s slender and has perfect tiny titties, or she’s thick and curvaceous, with powerful thighs and a tight body, milfs training is a mega turn-on for everyone. Who doesn't love seeing their favorite stars in skin-tight clothes, getting their legging ripped so you can get a peek at their pussy? This compilation is all about celebrating all of our beautiful stars getting sweaty and taking cock as part of their routine. See the mature hotties you love doing what they do best.

Girls Way - Ryan Keely, Penny Barber & Daisy Fuentes

Ryan Keely, Penny Barber & Daisy Fuentes - Compromising Positions
Released: September 19, 2024

Two friends, Ryan Keely and Daisy Fuentes, arrive at the home of their other friend, Penny Barber. They are surprised when Penny greets them while wearing yoga gear. It's revealed that Penny is an entrepreneur who wants to open a yoga studio. However, she's impulsive and has taken on many ventures in the past that did not work out.

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