"Penny Barber" 226

Related Terms: Penny Barber, Penny Barbers



Mommy's Girl - Haley Reed, Sabina Rouge & Penny Barber

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Haley Reed, Sabina Rouge & Penny Barber - Wingwoman
Released: May 28, 2022

Two teens, Sabina Rouge and her friend Haley Reed, are hanging out. Penny Barber, Sabina's stepmother, pops in and Haley instantly gets a crush on her, although Sabina doesn't seem to notice. Although Haley subtly tries flirting with Penny, Penny mostly ignores her... and instead seems to be paying attention to Sabina!

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Ultimate Surrender - Mona Wales & Penny Barber

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Mona Wales & Penny Barber - Close Match. One wrestler almost makes a cum from behind victory
Released: July 5, 2017

Penny Barber is Ultimate Surrender's favorite big tittied MILF who loves to get fisted. Mona Wales is Ultimate Surrender's Favorite leggy blond bombshell who loves to be fucked hard and humiliated. This match is exciting back and forth action with grapevines, giftwraps, sweeps, reversals and hard core competitive action at all times it's hard to know who will be the winner by the end of the match. One thing is for certain, no matter what the outcome, Penny Barber is going to get fisted. Mona wales weighs all of 114lbs while Penny Barber is 145. There are no weight divisions in the Big 10 tournament. It's just raw talent put on display in 100% real competitive erotic wrestling. Will the long bendy legs of Mona Wales be able to sweep Penny Barber and gain control, or will Penny Barber use her infamous giftwrap hold to disable her opponent and have her way with her? The action is back and forth. Both girls finger each other relentlessly. One girl gets the other to cum on the mats against her will with a coveted Orgasm on the Mat maneuver!. The winner gets to do what ever she wants to the loser. Winner face fucks the loser, throw her into doggy and fucks her pussy while she shoves a thumb up the losers ass. Loser is face sat until the Winner CUM!

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Brazzers Exxtra - Penny Barber & Jasmine Sherni

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Penny Barber & Jasmine Sherni - Swinger Set
Released: February 6, 2024

Swinger couple Mick & Penny are looking for new property. Being a freaky pair – the property is less important than the real estate agent – as Jasmine finds out when she takes these swingers on as clients. Jasmine tries to remain professional but can’t help herself and decides to get some threesome action with the hot married couple!

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Milf Hunter - Penny Barber

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Penny Barber - Car Karen Gets Fucked
Released: January 5, 2023

Jmac was gonna grab some pizza, but his plan changes when he sees a sexy MILF chewing out the valet for giving her car to her ex husband. Penny Barber is too much of a Karen to get a rideshare to pick her up... but she's got long legs and big tits, so Jmac offers her a ride! Penny's so horny she starts sucking his dick in the car and even gives him a foot job, then when they get back to the house it's on!

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Mylf Blows - Penny Barber

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Penny Barber - Her Sexual Appetizer
Released: October 14, 2019

Bookish MILF babe Penny Barber simply cannot wait for her date with her man tonight. She has been dreaming about him burying his long dick deep inside her juicy slit all week, and her patience has finally run out. She wants a sampler, so she seduces the lucky guy before they can even get out the door, inviting him to be her sexual appetizer. He breaks out his meaty sausage and the hungry MILF devours it, licking his shaft from balls to tip. He teases her cunt and she squirts like a fountain. Then, he penetrates her eager vag while she moans in pleasure. With gooey cum covering her face, it seems Penny has had her main course too!

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Infernal Restraints - Penny Barber

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Penny Barber - Beat the Brat 2
Released: June 7, 2013

This shoot is titled Beat The Brat because Penny Barber spent so long telling Cyd Black how proud she is for being so willful and defiant. When Cyd straps her down to the table she thinks it's going to be another light bondage session she can just laugh at. When Cyd starts pumping up her tits she doesn't know what to think. And when Cyd takes the whip to her pussy she thinks: "ANYTHING BUT THAT!". She goes right back to mouthing off the second Cyd shows a little mercy, but that's fine, it gives Cyd another opportunity to break her down. This time he bends her over and lets the cane do the work. She's sniffling and screaming in no time but Cyd doesn't stop until she's fallen in line. Her entire ass may be sore and swollen, but her ego is where Cyd will do the most damage.

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Moms Bang Teens - Penny Barber & Krissy Knight

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Penny Barber & Krissy Knight - Car Squirter Makes Nice With Mean MILF Threesome
Released: March 19, 2023

Blonde teen Krissy Knight gets so horny over her stepmom's new convertible, she just has to rub herself all over it. She video calls her boyfriend Jimmy Michaels, who rushes right over in time to see her squirt in the car. The teens fuck, but stepmom Penny Barber catches them just as Jimmy cums on the inside of the windshield. They're in big trouble, and she makes Krissy lick it off before marching them to her bedroom for a threesome.

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Mylfwood - Tana Waters, Spencer Bradley & Penny Barber

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Tana Waters, Spencer Bradley & Penny Barber - Porky's
Released: March 27, 2020

Who can forget the infamous locker room scene from Porky’s? Looking through that little peephole and seeing all those beautiful girls in their birthday suits - there’s nothing like it! Well, when busty MILF Penny Barber takes on the role of the moaning gym teacher Miss Honeywell, things get extra naughty after class. She catches two befuddled studs snooping around the girls’ locker room and teaches them a lesson with her domineering MILF snatch. She grabs their cocks one by one and stuffs them down her throat. Then, she gets her body rocked by the lucky guys at the same time! A sticky creampie all over the gorgeous MILF’s face is the perfect way to end this Hollywood classic.

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Ultimate Surrender - Penny Barber, Izamar Gutierrez & Mistress Kara

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Penny Barber, Izamar Gutierrez & Mistress Kara - 2017 Mom's I'd like to Fight ( MILF) mini tournament
Released: May 10, 2017

Today we have 2 mom's and one wrestler who makes everyone call her MOMMY. Keeping with Tradition, we have each wrestler matched up for to fight one round against each other. Round 1 is Penny Barber vs. Mistress Kara. Penny Barber come out like a bat out of hell but quickly learn her place on the mats against Kara. Round 2 is Kara vs. Izamar. Can Izamar take advantage of Kara after Penny has worn her down? Round 3 is Izamar vs. Penny Barber. This round is a must see with orgasms on the mat and brutal "hold her down" finger fucking. Round 4 is the "losers" tag teaming up on the winner. The winner is trapped on the mats, held down by two gorgeous wrestlers and made to take brutal pussy fingering. The prize round takes the two losers, one bound in rope bondage, the other controlled by pure brute. Izamar's ass is fucked right over Pennys face, Penny prays nothing falls out while both losers are humiliated by the winner. Tribbing, Fisting, rope bondage, Anal, Orgasms on the mat!!! This match does not disappoint.

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Sexually Broken - Penny Barber

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Penny Barber - Lippy Penny Barber has her face shoved into a box, dicked down 2 big cocks, uncontrolled squirting!
Released: September 13, 2013

Penny Barber is a lippy litte cunt. Talk talk talk, she is full of sass and clever quips all day long. We know what to do to lippy little cunts around here at Sexuallybroken-stuff their head into a box so that only the important bits stick out. Now she can talk all she wants and we don't have to deal with it. We start with a simple face down, ass up tie on our well-used bed, what makes this position unusual is the addition of a head box. Head boxes are handy when you only want to deal with the fun end. And Penny has fun to spare, her juicy bubble butt is just begging for attention. We aim to oblige around here. Locked in darkness with her ass and pussy completely exposed, Penny can't see a thing. All she can do is feel and endure. Feel not one but two big cocks walk up any time they want and just slide right in. There isn't a thing she can do to stop it. Far from panicking her, the situation seems to get her pussy wet. One after another, both cocks own her pussy. It is a brutal, relentless, teeth-chattering pounding. 10 inches of BBC are shoved up balls deep. Penny is so turned on she helplessly squirts, the puddle irrefutable evidence of just how much she loves being turned into a humping post. We use her squirt as lube to keep fucking that pussy, and use her hand to keep our dicks from getting cold. Just to keep her guessing, we add a flogger and a vibrator in as well. The thick "thud" of the sound of the flogger impact makes a wonderful accompaniment to the various gurgles and moans coming out of Penny's head box. We add the hum of a vibrator and it turns into a full sex orchestra. We use our fingers and the vibrator to finger blast Penny out of her mouthy little mind. Multiple orgasms shake through her quivering assflesh, her strict bondage increasing the intensity tenfold. The bondage, massive multiple orgasms, multiple dicks and head box serve to drop Penny deep into subspace, and she lies limply in her ropes. We finish up, leaving her shaking and sweating, covered in her own squirt and girl juices, broken words gurgling out of that smart mouth hole of hers. Something tells us she might be a little less sassy, at least for a while. And we always have the head box if we need to use it again….

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Perv Therapy - Penny Barber & Sophia Burns

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Penny Barber & Sophia Burns - Alex Says
Released: October 1, 2021

Perv Therapist Penny Barber is back, and this time she’ll be helping stepsiblings, Alex Jett and Sophia Burns. Alex has confidence issues, but Sohpia seems to be blooming and is happy to boss Alex around, making him pleasure all her sexual desires on a whim. Penny suggests the duo try role reversal to increase Alex’s confidence and get him out of his rut. The result is astounding, and soon he’s bossing Sophia and Penny around to do whatever he wants. There is no Perv Therapist quite as good as Penny.

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Ultimate Surrender - Penny Barber & Johnny Starlight

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Penny Barber & Johnny Starlight - Penny Barber vs Johnny Starlight
Released: June 14, 2018

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...

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Moms Lick Teens - Kylie Rocket & Penny Barber

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Kylie Rocket & Penny Barber - Sneaky MILF Games College Lesbian
Released: November 27, 2023

Kylie Rocket is annoyed by her dad's new girlfriend, especially the way Penny Barber keeps invading her space and leaving messes everywhere, but even she didn't expect Penny to flash her big tits over the breakfast table! The horny MILF starts touching Kylie as she games, asking if Kylie has a BF... or GF... or if she's experimenting with girls at college. Kylie tries to keep concentrating as Penny sucks her tits and licks her pussy, but when the hot brunette rubs their nipples together, then fingers her tight pussy, she just has to hit pause on her game to focus on cumming as Penny scissors her and brings out a strap-on!

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Perv Mom - Penny Barber

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Penny Barber - Strict But Fair
Released: January 16, 2022

Penny Barber is a stepmom who is hard to please, and Billy Boston constantly feels her stinging wrath. When Billy walks out on his chores one day, Penny decides it’s finally time to punish her unruly stepson. But Billy ends up liking the torture, and so to make things right, Penny comes on to Billy hard. The result is the start to what looks like a beautiful sex marathon between Penny and Billy—chores have never looked so fun.

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Bad Milfs - Naudi Nala & Penny Barber

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Naudi Nala & Penny Barber - The Naughty Naudi Teacher Feature
Released: April 27, 2022

Penny Barber catches her stepdaughter, Naudi Nala, getting naughty with her English teacher, Marcus London. At first, she is absolutely livid, but Penny wants some “English lessons” herself after seeing Marcus's talents. Soon after, Penny makes a proposition with Marcus, and if he wants to buy Penny’s silence, he’ll get Naudi into a good school — in addition to other terms as well.

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Shoplyfter - Penny Barber & Serena Santos

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Penny Barber & Serena Santos - Case No. 7906146 - The Right Way To Search A Girl
Released: June 2, 2021

Security officer Rusty Nails brings suspected thief Serena Santos into the backroom for questioning when his partner Officer Penny Barber decides to join in the interrogation. Serena swears she has nowhere to hide any merchandise so Officer Penny proceeds to submit her to a strip search in which they find an expensive watch hiding in her panties. Officer Penny then teaches Officer Rusty the proper way to do a cavity search on the girl, before making a devious deal with her to keep her out of jail. A few sexual favors supervised by Officer Penny and Serena can walk free.

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