Jan 1
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.
Mar 19
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...
Mar 17
Mar 17
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.
Mar 5
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.
Feb 27
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!
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Feb 24
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.
Feb 20
Feb 20
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.
Feb 17
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!
Feb 16
Feb 16
Penny Barber - A Taboo Hunger
Released: February 15, 2026
Feb 14
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…
Feb 13
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).
Feb 7
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.
Feb 4
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.
Jan 9
Penny Barber - POV: Your Stepmom Penny Barber Has Some News & Needs Some Consoling
Released: January 7, 2026
Jan 3
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.
Dec 27
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.
Dec 26
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.
Dec 24
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...
Dec 19
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.
Dec 18
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.
Nov 25
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.
Oct 18
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.
Oct 17
Oct 17
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.
Sep 24
Sep 24
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.
Sep 23
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.
Sep 23
Sep 23
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!
Sep 18
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.
Sep 12
Cast: Charlie Forde, Lauren Phillips, Lexi Luna, London River, Penny Barber, Reagan Foxx, Richelle Ryan, Shay Sights
Sep 9
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…
Sep 5
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!
Sep 1
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
Aug 29
Aug 29
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.
Aug 25
Aug 25
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.
Aug 13
Aug 13
Penny Barber - Cock-Hungry MILF Penny Goes Airtight In Gangbang
Released: August 13, 2025
A fast older woman seduces a young rideshare driver.
Aug 13
Aug 13
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.
Aug 6
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...
Jul 30
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.
Jul 28
Jul 28
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.
Jul 28
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
Jul 18
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!!
Jul 15
UPDATED Lexi Luna & Penny Barber - Call Me Ma'am
Released: July 14, 2025
