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Kink · November 24, 2025

Cock Worship

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 BarberWill Pounder

Kink · October 17, 2025

Gorgeous Gusher

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. Now on a sex box with hands bound behind her back, Penny gives Vince a foot job and then he stuffs his thick cock in her pussy and pounds her out. Penny is overwhelmed with his huge dick but loving every inch of it. Flipped on her side, Vince fucks her some more causing Penny to squirt all over the place and then back up on her knees Vince gives it to her again as Penny squeals and moans and cums uncontrollably again and again. Taking a quick break Vince slides his dick in Penny?s mouth and lets her clean all the cum off his cock. Then he fucks her pussy with his big toe making her squirt again. Wasting no time he pulls his squirting slut on top of him and fucks her cowgirl style until she cums hard and then on her back he pounds her pussy one more time with his big dick and cums all over her face.

Penny Barber

Vince Karter

Kink · September 17, 2025

Tiny But Mighty

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 slide 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.

Penny Barber

Luna Lovely

Kink · August 25, 2025

Spanking Mommy's Ass in Strict Bondage

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. After adding some weights, The Pope canes Penny?s feet and gets mean with the knitting needle. All of which earns a reward and the vibrator is stuffed between the clamps grinding out another orgasm. Next up Penny is suspended from one leg as the other and both arms are bound behind her back, and The Pope ties up her hair to complete the ensemble. He moves on to pulling her pubic hair too. The Pope crops Penny?s pussy, feet, and then her tits before getting the Hitachi again and alternating between that and the crop on her pussy, finally grinding the vibe into her clit as she tries to resist cumming only to give in, just to get the crop again. Then The Pope stuffs Penny?s wet pussy with the dildo on a stick and fucks her fast while fingering her clit only to return to the vibe to coax another orgasm from her. Finally Penny is bound to a crate on her side with her legs spread. The Pope gets the cane and works on Penny?s feet some more, alternating back and forth then adding the crop for fun. Then The Pope crops Penny all over, especially her ass and thighs. The Pope ties Penny?s hands behind her head and then further immobilizes her by binding her big toe. The Pope then crops her pussy before getting the vibrator again, grinding it into her clit. Then, after an adjustment to Penny?s bondage, The Pope crops the soles of her feet before moving on to finger-fucking her wet pussy. Once he knows she?s really holding out The Pope gets her to cum as he fingers quite the puddle from her gushing wet pussy.

Penny BarberThe Pope

Kink · July 2, 2025

Mommy's Cock-Hungry Hole

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. With Max now naked, Penny uses a vibrator on his cock, sits on his face, and while he licks her clit, she swats his thighs with a flat cane. Penny gets close but unties Max?s hands so he can stroke his cock and make it hard for her pussy. She licks his balls, uses the vibrator on herself and grinds on his legs. Just as Penny goes to put his hard cock inside her, Max cums prematurely without permission and has to face Penny?s wrath. She makes him apologize, re-ties his hands and blindfolds him. Penny uses the cane and crop and sits on his face. Penny sticks the suction cup of the dildo onto Max?s hairless flat chest and rides it to another squirting orgasm into his open mouth. Penny removes the blinders, sits on his face, and makes him lick her pussy until she cums, leaving Max tied up with the dildo still suctioned to his chest.

Penny BarberMax Mabry

Kink · January 1, 2025

Fuck Around and Find Out

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. Gagged, helpless, and obedient, Sage whimpers but is eager to please his master so he doesn?t complain. Next Sage is bent over on the bed with his wrists bound with a leather strap. Wearing long, black, shiny latex gloves Penny fingers his asshole and then fucks his butt with a strap-on. While pounding Sage?s ass she stuffs a huge dildo in her pussy and fucks herself until she squirts. Penny crams the same dildo up Sage?s tight ass and gets herself off several more times. Next, Sage is on his back, tied to the bed stretched out spread-eagle. Vulnerable and exposed, he is at the mercy of Penny?s sultry, sadistic desires. First she sucks and strokes his thick cock to make sure he is good and hard for fucking. Penny climbs on top of Sage in reverse cowgirl and fills her pussy with his man meat and bounces her way to a hot orgasm. She is so turned on she even stuffs her ass with dick and rubs her pussy until she cums again. Finally Penny mounts her sweet sub in missionary and fucks him hard until she squirts and then as a final reward jerks Sage off until he shoots his load.

Penny BarberSage Roux

Kink · November 27, 2024

Penny Trains Pet, Ashley

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!

Ashley Lane

Penny Barber

Kink · March 13, 2024

Pretty In Pink

Marcelo (sissy name Marcy), in his pink satin dress, is locked to the floor with his legs spread and his balls tied taught to a post, leaving him fully exposed for Mistress Penny Barber to do as she wishes. She starts with some cock and ball torment but that only gets Marcelo harder. So, to teach his disobedient cock a lesson, Penny decides that sounding is the right medicine. Next, Marcelo is on his back, legs tied wide open so Penny can use the paddle he made especially for this meeting. Penny doesn?t limit herself to just paddling his ass, she gets in some good foot torment and caning for good measure and then stuffs her fist up Marcelo?s welcoming asshole. After some thorough exploring of Marcelo?s guts with her fist Penny moves on to a big black dildo to finish her happy little sub. Finally, Marcelo is lying face down in a neck-down body-bag where his naked Mistress paddles his ass before she eats it, then flips him over to give him the reward he?s eared by being such a good sissy all day.

Penny BarberMarcelo

Kink · June 2, 2021

Before Daddy Gets Home: Mommy Penny Barber Fists Brat Natalie Mars

When Natalie Mars behaves like a brat, her Mommy Domme, Penny Barber, decides it's time for a spanking! She pulls Natalie over her knees and spanks Natalie's ass red. Natalie squirms as her Mommy slides her thumb into Natalie's cute asshole.After punishing her brat, Penny brings Natalie into the shower to prepare her for their Daddy Dom's arrival. Natalie's hands are bound behind her. After her Mommy bathes her thoroughly, Natalie eats her Mommy's ass. Next, Penny pinches Natalie's nipples hard before putting on latex opera gloves and fisting her girl's hole. Natalie moans as her Mommy's fist fucks her asshole.Penny then uses an anal spreader to stretch Natalie's hole wide open. She spits and squirts into Natalie's ass. She has Natalie bound and gagged and locked in chastity right before their Daddy returns from work.

Penny BarberNatalie Mars

Kink · November 9, 2018

MILF Agent Botches Undercover Anal and Sacrifices Step-Daughter

Bubbly and big-titted Penny Barber is determined to move up at her FBI job as an undercover agent. She has been working on one particular arms dealer Rob Piper, and is moving in for her last operation when Rob turns the tables on her. Claiming she is 5k short and that he is willing to cancel the deal, Rob gets Penny onto her knees and offering Rob anything he wants in exchange for the guns. Rob has been watching her round ass for months and knows exactly what he wants: Agent Barber with her jiggly red ass poised in the air for a hard flogging. Once her cunt has squirted multiple times and her ass is a bright pink from a heavy handed spanking, Penny gets on her knees and begs for Rob's HUGE cock in her mouth. Slobbering and gagging, Penny does the best she can with that massive dick and makes Rob very happy indeed. He throws her into handcuffs, pushes her head down and gives her the hard fucking she craves despite her protest that she is married. Railed hard and begging for Rob to cum in her, Penny is given a pass on the missing 5k and is sent on her merry way with her last arms pick up. It's too soon to celebrate for this hot MILF agent. She immediately receives a text notifying her that Rob has been playing her all along, and now has her step-daughter held hostage in a cheap motel. Penny rushed straight into the trap. Kendra is a gorgeous teen menace, tied in brutal backbend shibari and gagged with heavy metal clamps on her perky teen tits. She drools and scream around her gag as Rob offers Penny employment as his mole in the agency. Penny protests but caves once Rob starts fucking her darling daughter, making her squirt all over the floor. Swearing fidelity to Rob directly into Kendra's soaking wet cunt, Penny is made to lick and grovel until Kendra is ungagged and releases a torrent of cusses and back-talk like we have never seen. Penny has had enough of everyone playing her and telling her she sucks at her job. She cleverly offers Rob her daughter to use, and throws the little brat's mouth around his giant dick. Kendra is overwhelmed with cock, and screams in pain as Penny cruelly rips off her tit clamps and presses a vibrator down on Kendra's tender clit. Put in even tighter rope suspension Kendra takes every inch of Rob's hard cock and hollers with disbelief as she cums uncontrollably all over the floor in a fountain of squirt. The rest of the day is spent in a mother/daughter grudge match. Penny torments Kendra's tits with a flogger, smothering her dirty mouth with pussy and ass, and making sure she is milked of every last drop of teen squirt. Kendra eggs Rob on, insisting he cane Penny and fuck her in the ass. Penny's face during anal is a priceless silent scream of shock. Used up and fucked out, Kendra is made to lick Rob's cock straight out of Penny's ass and take a huge load on her face...which she then spits in her mother's face. Take that, bitch!

Penny Barber

Kendra Spade

Kink · July 20, 2018

Tight Bodied Teen Star and Anal Step Mommy Fuck Director's Huge Cock

Tight bodied teen Isabella Nice is done being managed by her over bearing Step-Mother Penny Barber. Unfortunately for her, she doesn't know Penny has been using her hot body and slut skills to buy Isabella every role she's ever had. When the director send Isabella away for wardrobe, Penny is ready to pay him interest on her daughter's big chance, getting on her knees and groveling for dick, her big nipples chained up with clips while she squirms and whines under the zapper. Tied in a tight strappado and bent over a chair, her big MILF ass is ripe for a hard caning, which she made to beg for. Smart mouthed as always, Penny is covered with red welts and ready to take a deep dicking her her ass and pussy. Unfortunately, Isabella comes back by the room and begins to understand how managed her career really in. Taking matters into her own hands, she offers her nubile little body to the director hoping to make it in the big leagues on her own. Seth puts her on the floor and shows her exactly what her is looking for in her performance. Slapped around, her labia tied to her toes in a painful squat with a vibe pressed to her pussy she starts to learn voice projection as she screams and begs for more cock in her throat, more orgasms, and to have the painful zipper torn off her body. Thrown over the bed and tied up she has her wet swollen clit cropped until she earns the fucking she was begging for. Cumming from the electrical torment and the cock in her tight pussy she really gets into her role. However, Mommy is none to happy, and decides to teach Isabelle about the finer points of acting, throwing her over her knee for a hard spanking, then humiliating Isabella and presenting her daughters reddened ass to the director for further use. Tied up in a painful partial suspension, Isabella is fucked, cattle prodded, and eventually thanking her Step-Mommy for every time she gets her little clit licked. Penny teaches Isabella how to take a cock in her ass with an up close lesson, including cleaning the cock off every time it comes out of Penny. For her biggest role ever, Isabella has her tiny tits clamps and tied and it made to take an athletic ride of the directors dick until her mother is satisfied she has learned her lesson and let's her cum and beg for a big load on her face.

Penny Barber

Isabella Nice

Kink · July 11, 2018

Penny Barber vs Mistress Kara

Welcome to the Summer Vengeance series Tournament on Ultimate Surrender! We have 13 of this season's finest veterans and rookies in a single knockout seeded tournament. Today we have our #7 ranked wrestler, Penny Barber, put against our #1 ranked wrestler, Mistress Kara. Penny is a curvy, big-titted, big-assed, brunette MILF who is known for cumming on the mats. Her wrestling skills is honed but her compulsive lust on the mats have lost her many fights. This is why she is ranked #7. Kara "The Queen" was originally ranked #2 behind Ariel X but Ariel has had to pull out of the tournament due to injury. Dee Williams will take Ariel's place. Kara will be bumped to #1 ranking, Dee Williams will default to #2 ranking. Kara is the Queen for a reason.. She easily dominates her opponents and makes them call her Daddy. Right of the bat, Penny is able to secure a Head Scissor and it puts Kara into trouble. Penny takes the lead in the beginning of the match and this mentally effects both wrestlers. Kara tries to come back in full force but is it enough to win her this match? Kara knows she promised to give up anal if she lost on Ultimate Surrender again, so there is a lot on the line here today! These girls give it everything they've got but only one can move on. The winner drags the loser into the locker room. Loser is fisted in the pussy and fucked in the ass. She is then humiliated and made to concede her loss: she's out of the tournament and the chamption moves on to the next victim!

Penny Barber

Mistress Kara

Kink · June 13, 2018

Penny Barber vs Johnny Starlight

Welcome to the Summer Vengeance series Tournament on Ultimate Surrender! We have 13 of this season's finest veterans and rookies in a single knockout seeded tournament. Johnny Starlight, ranked #10, is a curvy dark haired beauty who was our intermin Rookie Cup champion this season. Penny Barber, ranked #7, is everyone's favorite big mouthed MILF with a terrible gift wrap hold that gives ever girl problems. Johnny wants to squash Penny and fist her pussy. Penny wants to hand gag and humiliate the sassy little rookie. Penny Barber bullies our rookie in the first round with her signature hold, the "gift wrap" and is able to hold Johnny down. This frustrates her and get her close to orgasm. Sadly, for Penny her weakness is fingers in the pussy and once that happens, it can be game over for her. Today, that's exactly what Johnny needs to do. The winner of this match will move on in the tournament which means more money, more fame, and more fans. One girl gets trapped, fingered relentlessly and is utterly broken by the end of the match. The winner has her way with the loser. The winner hand gags, hair pulls, and puts feet in the mouth of the loser and fucks her pussy in brutal fashion.

Penny Barber

Kink · April 6, 2018

2 Butt sluts get Fisted and Fucked

The gorgeous Savannah Fox takes out her two foxy MILF butt sluts to play! Dark haired Penny Barber is so glad to be out of her cage, and super blonde London River is eager to get fucked. First Savannah must make sure each ass is tender. She spanks her toys' asses and takes a deep whiff. She uses Penny's mouth to warm up London's asshole and when Penny gets mouthy, she shoves her head right in between London's cheeks. Then London gets to lick and smell Penny's delicious asshole. Once these two sluts are all warmed up, Savannah breaks out the toys! She starts with the fat, cold stainless steel double ended dildo. She teases Penny with it before plunging it in London's greedy asshole. For Penny's asshole, Savannah chooses a glass corn on the cob dildo. Penny squirms as the cold toy gets pushed slowly in and out of her asshole. These hungry slutholes are aching for more and Savannah knows just how to satisfy them. She has London hold Penny's legs open as she slides her fist right into Penny's ass. Penny screams as the fist slowly sinks into her ass and tries to squirm away, but is unable to escape and made to orgasm on Savannah's fist. Then Penny holds London's legs open as Savannah pushes her fist into London's slutty asshole. Once the fist is in, London can't stop cumming as Savannah fist-fucks her hole. As a reward for being so good, London gets stuffed with Penny's fat cock. London moans as her ass is fucked and Savannah is so turned on, she starts masturbating and fucking her own asshole. The more London screams, the more aroused Savannah is. She squirts all over London, covering her dirty sluts in cum.

Savannah Fox

London River

Penny Barber

Kink · December 22, 2017

Cock Crazed Step-Mommy Just Wants Anal For Christmas

Penny Barber is bustling around the house preparing a cookie plate for her thick dicked step-son to get home for Christmas. Her husband is safely scheduled to return a day late, leaving her lots of time to get all her slutty holes filled and get her round ass punished for all her misdeeds this year with a strict belting and caning. Huge tits bouncing in her Christmas sweater she runs right into a holiday disaster: her step-son making out with his goth girlfriend he brought home for Christmas. Cookies come crashing to the floor as Penny regards her new rival Ivy LaBelle. A curvy perfect body to match Penny's with plenty of attitude, iconoclast Ivy is having none of Penny's holiday cheer, and drags her boyfriend upstairs to fuck her in tight bondage, flogging her wet cunt, and spanking her big round ass. Xander takes Ivy to task for thinking she's superior to his step-mother, but nothing prepares him for when Penny charges right up the stairs and calls him out of his bedroom in a clever bid to get some. He politely tries to stay out of trouble, but Penny get's right on his cock and tell's him she needs her punishment. Her handsy bullshit activates a sadistic flare in him, and he throws her over the couch, spanking the shit out of her, belting her ass, and giving her a strict caning. Putting her in tight belt bondage he plows her ass hard and fast, making her scream and cum like a whore in the living room. However, even that isn't enough for Penny. She waits like a cat for her prey in the living room all night, and eventually is rewarded when Ivy appears to steal some cookies from Santa's platter. She gives Ivy her Christmas present early: a big metal butt plug to prepare for her step-son's monster cock. Before she can get fucked, Ivy has to endure confessional, having hot wax dripped all over her tender flesh, flogged off, and made to hold her orgasms back while holding heavy buckets of coal. When Penny is sure this little goth slut is good enough for her step-son, she commences in training her how to take a huge dick in her tight ass, smothering her new step-daughter in her tits and cropping her swollen red cunt until she cums, shuddering and screaming in front of the Christmas Tree.

Penny Barber

Ivy LeBelle

Xander Corvus

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Latest Updates from Kink

Cock Worship

Gorgeous Gusher

Tiny But Mighty

Spanking Mommy's Ass in Strict Bondage

Mommy's Cock-Hungry Hole

Fuck Around and Find Out

Penny Trains Pet, Ashley

Pretty In Pink

Before Daddy Gets Home: Mommy Penny Barber Fists Brat Natalie Mars

MILF Agent Botches Undercover Anal and Sacrifices Step-Daughter

Tight Bodied Teen Star and Anal Step Mommy Fuck Director's Huge Cock

Penny Barber vs Mistress Kara

Penny Barber vs Johnny Starlight

2 Butt sluts get Fisted and Fucked

Cock Crazed Step-Mommy Just Wants Anal For Christmas