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.
Romi Rain, Cory Chase, Penny Barber, Syren Demer, Sophia Locke, Shay Sights & Rachael Cavalli - Menopausal Step Mommy
Released: March 19, 2026
When Debbie (Cory Chase), a frazzled suburban housewife on the verge of menopause, decides to throw a Botox party to lift the spirits of her equally tired MILF friends, she has no idea what kind of transformation awaits. Enter Veronique (Romi Rain), a mysterious and sultry consultant who introduces Debbie to a revolutionary supplement that promises relief from the hot flashes and hormonal chaos that plague her.
What Debbie never expected, however, was for Veronique’s product to instantly consume her with a new kind of heat… something wild, sensual, and nearly uncontrollable. What starts as a mild hormonal flare-up quickly turns into a full-blown sexual revival, with her lazy stepson, Jordan (Max Fills), just happening to be in the wrong place at the VERY right time...
Penny Barber - Like Father Like Son
Released: July 15, 2025
One morning, he decides to test her, ordering stepmom to fetch him a glass of water, then complaining that it's warm, so he orders her to bring ice. When Penny balks, his curt response is: "You want to live here, right?". Worse yet, he flaunts his assumed power, walking around the house naked in front of her, humiliating Penny.
She finally erupts: "I know that your parents neglected you. When I married your father, I did my best to make sure that you had all the love I felt you didn't have. I made this a home, and you don't have to humiliate me! Your father abandoned me too -my life is in shambles, I have nothing, all right? You are a spoiled brat!". She stalks out of the living room, leaving James to ponder what's next.
Penny Barber & Scarlette Moon - Deep Inside The Splash Zone
Released: March 4, 2026
Newcomer, Scarlette is on her knees, ready to please Penny. Penny pulls Scarlet’s perky tits out and slaps them around. She makes Scarlette get on all-fours and spanks her cute little ass. Next she makes her little pussy squirt and Scarlette laps it up. Penny finger-bangs Scarlette’s pussy, puts a ball-gag in her mouth, and then punishes her with the zapper for having tits too perfect. After that, Penny puts clothespins on Scarlette’s pussy, covers her body with lube and hot candle wax, and then makes Scarlette cum with her big strap-on cock. In the final scene, Scarlette is in a frog-tie with her wrists tied to her ankles. Penny rubs Scarlette’s hard little clit and then shoves her fingers inside Scarlette’s greedy little pussy. Scarlette wants to cum again but Penny doesnt let her and uses the vibrator on herself, and then makes Scarlette lick her pussy.
Ariel X & Savannah Fox - Sexy Lesbian Nuru Massage
Ariel X - Ariel Lifts and Carry Handsome Man
Ariel X & Mia Little - Anal Physical Therapy
... and MANY more!
Penny Barber - College Dean Penny Barber Takes Her Student's Need Seriously
Released: February 24, 2026
College Dean Penny Barber is interrupted mid-phonecall by a student who's come to complain about his professor being particularly tough on him and accusing him of doing things like using AI for his papers. He won't let it go, and is hoping Penny will step in and take a look, tell off the professor, anything in her power. While she's not swayed by his arguments, she can't ignore that bulge in his pants and offers a little quid pro quo as she gets up and walks around to meet him head-on... well, on her knees, taking his cock out for a nice, sensual blowjob. After stripping naked for him, he's ready to go and he takes a seat in a nearby chair so she can get on top to ride him cowgirl, doggystyle, and more, until he fills her up with a nice big creampie load.
Penny Barber - Stepmoms Creampie Apron
Released: February 20, 2026
Axel Haze and his friend Rion King are watching TV when Axel's stepmom Penny Barber comes in. She claims that they're better than this when she sees what a mess they've made. She lets them know that they've earned a little reward.
Haley Spades & Penny Barber - Slutty Cheerleader Caught Mid-Plot
Released: February 17, 2026
College cheerleader Haley Spades has a problem: she's gonna get kicked off the squad if she fails the class taught by stern teacher Penny Barber. Haley thinks it's wise to sneak into Penny's office one evening to steal some test answers, but Penny catches her red-handed. Haley could be in real trouble here... but she knows Penny has a thing for cheerleaders and she's not opposed to using sex to calm down her pissed off professor!
River Lynn & Penny Barber - Penny Barber vs River Lynn, Part 2: A Double Anal Dream Come True… (“Mom vs GF” Special)
Released: February 14, 2026
Penny Barber vs River Lynn, a “Mom vs Girlfriend” special event (part 2 of 2:) River isn’t going to back down so easily. If Penny thinks she’ll just get her way, uncontested, she’s wrong. They both want Tyler, but can they both have him? Penny is willing to make a deal - if River can prove she’s worthy, they can share Tyler. The test? A double-headed dildo… Penny wants to see River’s anal skills. River is sluttier than Penny thought, and passes the test. Now, they’ll truly go head to head and see whose asshole Tyler prefers. In the end, it’s a win-win-win outcome. How lucky is Tyler that he gets to experience these goddesses and their tight holes? This is a new dynamic he could get used to…
River Lynn & Penny Barber - Penny Barber vs River Lynn, Part 1: Your Girlfriend Is Only Allowed To Watch (“Mom vs GF” Special)
Released: February 13, 2026
Penny Barber vs River Lynn, a “Mom vs Girlfriend” special event (part 1 of 2:) What happens when a mother isn’t ready to give up her favorite and most important man? Anything his girlfriend can do, she can do better. She’ll just need to remind him that he only needs one woman in his life. Penny is the perfect overprotective, jealous, protective mother. Nobody can have her stepson’s cock except her, and she’ll make sure River knows it. In fact, she’ll show her - River can watch while Penny gets fucked by Tyler. This dick belongs to her, not some new girl. But, things can change, and if River proves herself worthy, maybe she can get in on the fun… (Continued in Part 2).
Hazel Moore, Penny Barber & Alona Bloom - Tickle Tension
Released: February 7, 2026
Mandy (Hazel Moore) is texting in her bedroom when her nosy stepsister, Dawn (Alona Bloom), comes in and starts probing about who she's texting. When Mandy lets slip that she's chatting with a crush, Dawn becomes even more nosy, trying to get the sweet deets from Mandy. When Mandy doesn't give in, however, Dawn playfully tickles her in an attempt to get the truth from her. That's when their stepmom, Cynthia (Penny Barber), hears their laughter and innocently joins in on the fun, which leads to them all tickling each other. But the group tickling leads to unexpected feelings of arousal between all of them. After briefly acknowledging their newfound feelings, they decide to explore the feelings even further with a steamy, sensual threesome.
Penny Barber & Rissa May - Seductive MILF Penny Shares A Cock With Rissa
Released: February 4, 2026
A fashion photographer knows how to bring out the sex appeal in her young subjects.
Penny Barber - POV: Your Stepmom Penny Barber Has Some News & Needs Some Consoling
Released: January 7, 2026
Penny Barber - Nympho MILF Massage
Released: January 3, 2026
Penny Barber is in the mood to get fucked! she hires a masseuse Victor Ray, with the intent to seduce him into sex. After a brief flirty intro, she gets down to business, being pushy and taking control of the massage to make sure it goes down the way she wants it. Victor tries his hardest to keep it professional, but she won't let him slack on the job.
Penny Barber - Penny Barber Consoles Her Despondent Jock Stepson
Released: December 26, 2025
Special XMas Treat!... Busty Super-MILF Penny Barber is Back in Action by Member Request! Today, Penny Barber checks up on her depressed and despondent stepson, sulking on the couch, upset that his college's basketball team lost yet another game. She tries in vain to listen and hear him out and cheer him up, but nothing seems to get through to him or help in any way, he's just resigned to being upset. Finally, she realizes he's not upset about the game, but something else entirely : he likes a girl at uni but he's still a virgin, and feeling self-conscious about it.
Penny Barber - Penny Barber Consoles Her Despondent Jock Stepson
Released: December 26, 2025
Special XMas Treat!... Busty Super-MILF Penny Barber is Back in Action by Member Request! Today, Penny Barber checks up on her depressed and despondent stepson, sulking on the couch, upset that his college's basketball team lost yet another game. She tries in vain to listen and hear him out and cheer him up, but nothing seems to get through to him or help in any way, he's just resigned to being upset. Finally, she realizes he's not upset about the game, but something else entirely : he likes a girl at uni but he's still a virgin, and feeling self-conscious about it. She's pretty sure some lucky girl out there would be happy to be his first to get it out of the way, and slowly works up the nerve to hint at being an ideal candidate for the task. He's skeptical at first, but when she slowly caresses his crotch and then unzips his pants and takes out his hard cock, he's only too happy as she gives him a long sensual blowjob, then continues stroking his cock while he unbuttons her dress to suck on her big and perky MILF tits. He returns the favor, spreading her out on the couch to lick her pussy, then gets right to work pounding her pussy missionary. She then takes charge, putting him on his back and riding his cock cowgirl style, until they both cum hard together.
Penny Barber & Emma Rosie - A Family That Nudes Together, Stays Together
Released: December 24, 2025
Axel Haze nervously brings his girlfriend, Emma Rosie, home to meet his stepmom, Penny Barber, for the first time. But Emma gets the shock of her life when Penny greets them NUDE! She's even MORE shocked when her boyfriend strips down to join his stepmom!
It's soon revealed that the family enjoys a nudist lifestyle. After discussing it with each other, they decided to just rip off the band-aid and show Emma instead of telling her upfront. Emma, loving Axel very much, decides to try accepting the nudist lifestyle...
Penny Barber & Coco Lovelock - Special Christmas Orgy For Cuckold
Released: December 19, 2025
Busty bombshell Penny Barber fucks like a goddess among MILFs, her voluptuous body a masterpiece of curves that her cuckold husband worships from afar. But on Christmas Eve, she finally grants his deepest fetish: watching her tight, shaved pussy get stretched and pounded by another man's thick cock right in front of him. To orchestrate this ultimate taboo holiday gift, Penny ropes in her naughty little stepdaughter Coco Lovelock and her hung stepson.
Romi Rain, Cory Chase, Penny Barber & Syren Demer - Menopausal Step-Mommy
Released: December 17, 2025
When Debbie (Cory Chase), a frazzled suburban housewife on the verge of menopause, decides to throw a Botox party to lift the spirits of her equally tired MILF friends, she has no idea what kind of transformation awaits. Enter Veronique (Romi Rain), a mysterious and sultry consultant who introduces Debbie to a revolutionary supplement that promises relief from the hot flashes and hormonal chaos that plague her.
Penny Barber - Cock Worship
Released: November 24, 2025
Will Pounder is bound to a wooden chair leaving his hairy body exposed for Penny. She kisses him down to his feet before moving up and releasing his big cock. Wasting no time Penny strokes Will’s cock and gets him nice and hard while she admires his body. Penny edges his hog with her mouth for a while and then ties off his cock with some string and giving him a bit of a titty-fuck. Then Penny grabs the Hitachi and uses it to tease Will’s while she sucks him and grinds her pussy against his hard dick. Will tries not to cum but fails. Next up Will is bound to a padded table and Penny rides his fingers and hand before moving on to stroking his cock some more, getting it ready for round two. Soon Penny mounts Will and sucks his cock again while he licks her pussy. Then Penny slides Will’s hard cock inside her dripping pussy and rides him to the edge before dismounting and stroking his hard cock to the brink again and again before he finally blows past the edge and unloads all over them both.
Penny Barber & Summer Col - Sneaky Checkup
Released: October 18, 2025
Daisy (Summer Col) is in a medical exam room for a checkup, accompanied by her stepmom Margaret (Penny Barber). As they wait, it's clear that Daisy is horny and secretly in a sexual relationship with Margaret, who tells her to behave. But when the doctor, Dr. Q (Siouxsie Q), comes and starts the examination, Daisy does anything BUT behave as she tempts Margaret into fooling around with her right under the doctor's nose! During the examination, Daisy and Margaret sneakily fool around, all while Dr. Q is oblivious. But when the doctor finally gives Daisy a clean bill of health and leaves, Daisy and Margaret finish what they started.
Penny Barber - Gorgeous Gusher
Released: October 17, 2025
Penny Barber and Vince Karter get it the fuck on in this super hot Dungeon Sex update. To begin, Penny is chained to the floor as Vince approaches his bound and sexy prey. He tears Penny’s shirt off revealing her tits and then warms her up with the flogger to get her ready for his big cock. After hitting her breasts and the arches of her feet, Vince fucks Penny’s wet pussy and makes her squirt immediately. Next Penny is standing tied up with nipple clamps while Vince vibes her pussy with the Hitachi and fucks her from behind, throwing Penny into another squirting orgasm.
Penny Barber - What's In the Box? Nookies Naughty Delivery
Released: September 23, 2025
A very fun night at home was in the plans for Rion and his girlfriend before she travels for business. He even ordered some sexy items for them to enjoy that were just about to be delivered. But when she cancels on him at the last minute, what can he do about it? The only logical answer is to fuck the Nookies Delivery girl, of course! That girl in question is Penny Barber - a hot delivery chick who discovers what's in the box and decides that Rion is super cute and she's down for a little sexy time fun.
UPDATED Penny Barber & Lilly Bell - The Secrets We Share (5 scenes) + Full Movie
Released: September 23, 2025
A 20-year-old exchange student, Anna (Lilly Bell), arrives at an idyllic suburban home for a two-week summer immersion program, only to become entangled in a web of dark family secrets.
Penny Barber - MILF Pact 6 - Scene 4 - All IN!
Released: September 23, 2025
It's time to go all in and get exactly what you need! MILF babe is sucking and fucking young cock! Do not miss this babe inepic action!
Penny Barber & Luna Lovely - Tiny But Mighty
Released: September 17, 2025
A naked Luna Lovely starts wrapped in rope in a full suspension. Penny Barber enters the dungeon in tight high waisted latex pants and a strap on. Penny first torments Luna’s feet. She zaps Luna with electricity, puts clover clamps on Luna’s labia, and hits her pussy with the cane. After that, Penny slides her fat dildo inside Luna’s slutty pussy and fucks her to orgasm. In the next scene, Luna is bent over, bound to a fuck-box. Penny gets her pretty tits out and takes her time making Luna’s ass turn bright red, hitting it continuously with a big wooden paddle. Penny fucks Luna’s tight asshole with her strap-on and then lets her cum on the vibrator. Just when Luna thought her butt cheeks were safe, Penny gets a long paddle and hits her ass and thighs. In the final scene, Luna is on her back. Her arms and legs are tied up and a now naked Penny Barber climbs on top of her. She puts her feet in Luna’s face, licks her pussy, and teases Luna’s clit with her hard nipple. Penny rubs her pussy on Luna’s pussy and they both cum hard but Penny isn’t finished with her. Penny sits on Luna’s face and Luna licks her pussy until Penny drips cum all over her face.
Cast: Charlie Forde, Lauren Phillips, Lexi Luna, London River, Penny Barber, Reagan Foxx, Richelle Ryan, Shay Sights
Penny Barber - Confidence Boost
Released: September 9, 2025
A concerned step mom decides it’s time for her son to become a man. He just needs a little help…
Penny Barber - Mommy's Affair
Released: September 5, 2025
Hot nasty MiLF has a dirty secret watch her get nasty and wild! This is hardcore fucking ! Mom likes to suck and fuck!
Penny Barber & Allison Rey - Pussy Loving Wives
Released: September 1, 2025
Hot lesbian babes are ready to get nasty! Dripping wet pussy action! These babes are ready for anything
Penny Barber - Tight Grip, No Escape: Penny Barber Handjob
Released: August 18, 2025
Penny Barber, dressed in a striking red dress, takes full control in this POV handjob scene. With a firm and teasing grip, she keeps him on edge, denying release as she dictates the pace. Every stroke is deliberate, leaving him desperate and powerless under her command. She finally is allowed to cum he shoots a massive cumload all over himself to Penny's delight.
Penny Barber - Spanking Mommy's Ass in Strict Bondage
Released: August 25, 2025
Penny Barber reunites with The Pope for some hot rope bondage. For starters Penny is bound kneeling on a wooden crate with her arms bound behind her back and legs tied to opposing support beams leaving her pussy exposed for The Pope to explore. The Pope puts clamps on her nipples then flogs her ass before getting the Hitachi and grinding it into her pussy. The Pope flogs Penny’s abs then removes the clamps to flog her tits before reapplying the clamps to her labia.
Penny Barber - Cock-Hungry MILF Penny Goes Airtight In Gangbang
Released: August 13, 2025
A fast older woman seduces a young rideshare driver.
Stevie K, DD White, Elizabeth Skylar, Linda Lan, Scarlett Venom, Suki Sin, Aderes Quin, Shay Sights, Lolly Dames, Penny Barber, Ryan Keely, Diana Grace & Reagan Foxx - Compilation: Milfs Riding Frenzy
Released: August 13, 2025
Everyone loves a hot, horny milf. All those years of fucking and getting pounded have taught them exactly how to please your dick. One of their favorite moves? Riding it until you can't resist unloading your sticky cum inside their wet pussies. They love feeling like a slut, and nothing makes them feel like that than using your cock to have an orgasm. Don't worry, they won't stop until you cum too, and you'll get to see their big tits bouncing and their asses banging against your balls over and over until you can't handle how turned on you are.
Penny Barber - Coach Plays Both Sides - S1:E7
Released: August 6, 2025
There's a big problem between teammates Parker Ambrose and Sage Roux. Their coach, Penny Barber, has called them to her office to figure out a solution. She sits the guys down and lectures both of them.
Parker accuses Penny of fucking her players, and while Penny denies it she also gets up and pops out her tits for Sage to play with. Parker definitely wants some too, so Penny lays on the desk where she can suck Sage off while Parker eats her pussy. Sage gets the first opportunity to shove it in while Penny turns around to give Parker some good suck too...
Abby Rose, Bubblez Bankz, Mandy Monroe, Addyson James, Nicole Emma Vaunt, Daisy Fuentes, Naomi Foxxx, Kendra Heart, Charley Hart, Payton Preslee, Angel Wicky, Penny Barber & Pristine Edge - Insane Milf Orgasms Compilation
Released: July 30, 2025
What’s up, MYLF lovers? When it comes to orgasms, the only thing hotter than a bodacious milf cumming is when they do so with an extra dose of freakiness! Come check out this amazing collection of beautiful ladies experiencing the wildest orgasm of their lives. Top stars such Angel Wicky, Charley Hart, Naomi Foxxx, and Nicole Emma Vaunt scream, squirt, and shout and do the kinkiest faces while they reach insane orgasms for you to fap to! These stunning ladies are triggered by the most unconventional situations, and it takes a nice fingering, a good old pussy-pounding or some random shit scenarios to make them reach their climaxes! So sit back, relax, grip your meat, and jerk to this horny collection of insane milf orgasms.
The.Older.Woman.XXX.DVDRip.x264-CiCXXX
Cast: Dee Williams, Maitland Ward, Penny Barber, Syren De Mer, Alex Jones
Fulfill your fantasies with a more mature kind of lady in MILFY.com's The Older Woman. This series is all about the sweet and sensual sexuality proven to only gets better with age. Featured cover girl Dee Williams shows a younger man who catches her eye a good time while her husband isn't looking. Maitland Ward, Penny Barber, and Syren De Mer also feature in our lineup of exquisite beauties. Detailed stories, high class production values, and elite performers: sexy never goes out of style in MILFY.com's The Older Woman.
Penny Barber & Leana Lovings - Lesbian Stepmother 9 - Naughty Lesbian Mommy
Released: July 28, 2025
Naughty Lesbian sex is about tobe epic Pussy lickinhg dripping wet fun takes things to the nxt level! This mother daughter duo is all about pleasing
Penny Barber - Deep Inside A Hot Mom
Released: July 18, 2025
Nasty horny babe is ready to get her pussy slammed! Relentless fucking and explosive sex has never been this nasty!!
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!
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...
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.
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.
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!
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…
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.
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.
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.
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.
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.
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.
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.
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.
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...
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.
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".
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!
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 & 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.
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
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.
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!
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.
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.
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.
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!
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?
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.
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.
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!
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...
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.
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.
Brooke Barclays & Olive Glass - Getting It Back pt. 1
Cadence Lux & Sadie Summers - Falling For a Married Woman
Charlie Forde, Jessica Ryan & Penny Barber - Book Club pt. 2
Cherry Candle & Penny Barber - Is Something Wrong with Me?
Dharma Jones & River Lynn - I Think I Love You
Penny Barber & Jasmine Sherni - Nerdy Roomie Is A Secret Freak
Released: September 14, 2024
Jasmine Sherni is horny, but her BF says he's too busy for an x-rated video call, so she just has to take care of herself. That's when her nerdy roommate, Penny Barber, hears noises and sneaks closer to listen at the door! Penny starts touching herself as she watches her hot roommate play with her pussy, then sneaks to her room to use Jasmine's vibrator and sniff her panties, getting off to the sounds of her cumming on the other side of the wall. Jasmine goes looking for her toy and finds it and her panties under Penny's blanket, and she decides to have some fun with the secret freak! They lick each other and share some toys, then trib, leaving both of them satisfied.
Cast: Freya Parker, Gizelle Blanco, Jessica Ryan, Lauren Phillips, Maya Woulfe, Penny Barber, Serene Siren, Vanna Bardot
Director Pat Myne bring you 8 of the industry's hottest, wettest girl-girl starlets in their annual showcase series "Lesbian Performers of the Year 2024"! This year's batch of awards season favorites get candid about their passion for other women and explore each other's bodies with fingers, tongues, and toys to produce earth-shaking orgasms in the way only a Sapphic can. AVN MILF Performer of the Year Penny Barber gets a taste of Performer of the Year Vanna Bardot; XBIZ MILF Performer of the Year makes love with Freya Parker; Sultry Jessica Ryan gushes over her love of women with sweet Maya Woulfe; finally, renowned lesbian Serene Siren seduces this year's Lesbian Performer of the Year Gizelle Blanco.
Penny Barber - Professor Penny Barber Takes Every Inch Of Students BBC
Released: September 4, 2024
An art professor gives her student a lecture at a private gallery showing, and provokes a response out of him.
Cast: Lauren Phillips, Penny Barber, Reagan Foxx, Ryan Keely, Shay Sights, Sophia Locke
The hottest MILF showcase of the year has arrived; Elegant Angel proudly presents "MILF Performers of the Year 2024"! The award-winning series returns with more of the most acclaimed, prime MILFs in porn. Pat Myne directs four provocative new scenes, featuring anal, lesbian, and boy-girl action, and culminating in an epic 4-woman reverse gangbang that completely drains Zac Wild's balls. Starring Sophia Locke, Reagan Foxx, Shay Sights, Ryan Keely, XBIZ MILF Performer of the Year Lauren Phillips, and AVN MILF Performer of the Year Penny Barber.
Penny Barber - Primals Taboo Family Relations Penny Barber Sex Starved Stepmom Finds Out Her Stepson Has A Monster Cock
Released: August 2, 2024
Penny Barber - A Fucking Conversation
Released: July 12, 2024
Enjoy the latest episode of "A Fucking Conversation" and "Cum Corner" with the super-fit super-sexy MILF Penny Barber!
Penny Barber - Carry-On Stroker Surprise
Released: July 22, 2024
Penny Barber and her family are going on a trip soon, and her teen's friend Nathan Bronson will be joining them. While her teen and Nathan are out shopping at the mall for some last-minute things for the trip, Penny decides to pack lunches into the boys' carry-on bags. But when Penny opens up Nathan's carry-on to put a lunch inside, she is shocked to discover that he's packed a male masturbator... in other words, a SEX TOY for stroking his cock!
Penny Barber - Case No. 8002505 - The Magic Milf
Released: July 13, 2024
Penny is a wicked woman with a talent for sleight of hand. She has no issues swindling her customers with her theatrics, but one day, her actions come back to bite her in the butt. Officer Mike interrogates Penny and learns of her thievery - now it’s up to him to bring the milf to justice. She isn’t going down without a bit of a fight, and she knows just what kind of man Mike is. All she has to do is offer up her pussy and suck his cock a little, and she knows he’ll turn a blind eye to what she’s done.
Penny Barber - The Lover Of His Stepmom's Dreams
Released: July 10, 2024
When Penny Barber stirs one morning and makes her way out to the kitchen, her stepson, Ricky Spanish, greets her but notices how distracted she is. Penny opens up about how she's frustrated that she can't remember most of the details from her dreams last night, feeling like she is destined to connect with someone...
Penny Barber - Better Late Than Never
Released: July 5, 2024
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 letting him know it. Will gets his chance to fuck the stunning milf soon enough when she grabs his hard cock beneath his shorts. Penny gets to sucking, fitting Will’s cock deep down her throat as part of her routine. Will pounds Penny’s pussy until he can feel his load coming. Penny gets back on her knees, and Will busts hard onto her beautiful face.
Nicole Kitt & Penny Barber - Dirty Cops - Episode 4
Released: June 24, 2024
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 kisses Bishop, then Jones. DA Hopkins (Isiah Maxwell) joins in the foursome, fucking Bishop while Jones pounds the captain's pussy! Warren warns the rookies to keep their mouths shut about the traitor Detective Harris and do whatever it takes to bring Officer Allff home.
Siri Dahl - The Bottom Floor
Released: June 14, 2024
The Bottom Floor is an invitation-only POV experience combining the genres of personal attention with the fetish/bdsm/group sex party niche.
Be prepared to be taken on a personalized journey into the depths of a private underground sex party where fetishes of all kinds are proudly on display. But you are not alone since Siri Dahl is your date and personal tour guide for the evening. Siri is excited to mingle with the partygoers, catching hungry looks from the likes of Seth Gamble, Codey Steele, Aiden Starr, Hazel Grace, Dillon Diaz, Penny Barber, and Davin Strong...
Penny Barber & Nicole Kitt - Is That A BUTTPLUG??
Released: June 13, 2024
Two friends, Nicole Kitt and Penny Barber, have a longtime, ongoing game where they try to pants each other while the other isn't looking. The thing is... Nicole ALWAYS loses! Penny is just too good at using various tricks, such as ringing the doorbell or leaving out dirty dishes, to distract Nicole so Penny can sneak up and pants her. And one of the rules of their game is that the loser can't retaliate on the same day, so it's really tough for Nicole to get Penny back...
Penny Barber - Taboo Series Episode 3 - Off Limits
Released: June 7, 2024
Hot babe is ready to get her pussy pounded! This is epic play, including mutiple positions and explosive climaxes!
Rachael Cavalli, Cory Chase, Penny Barber, Sophia Locke, Kylie Rocket, Lulu Chu, Fit Kitty, Alexa Kiss, Madison Brite, Sophia Sterling & Jewell Marceau - Muscle Mommies Compilation
Released: June 5, 2024
What’s up, TeamSkeet fans? It’s time to jump into another Selects update! For this go around, we’re celebrating all the wonderful muscle mommies. There is something particularly exciting about muscle mommies. They have a strong, commanding presence and love taking cock. Watching these fit babes work both their submissive and dominant sides all at once is always thrilling. We knew we had to showcase some of our favorite babes on the site and show off their powerful statures. See these muscley babes suck cock and get fucked hard!
