Penny Barber, Cheyenne Jewel - Hard Torture and Deep penetration of BDSM Sex (Ultimate Surrender) (2020 | HD)

Today we are getting down to the wire. We have the Cheyenne Jewel who is a beautiful, muscular Cowgirl ranked 2nd in our Big Ten tournament. She is taking on Ultimate Surrender’s favorite Bratty MILF, Penny Barber. Penny Barber has a brutal Giftwrap maneuver that most girls can not seem to figure out. Cheyenne Jewel has a bull like ability to push girls over and overpower them. Both of these beautiful wrestlers have fine asses and they use their asses to hold each other down. One wrestler takes the lead after ripping and orgasm on the mat from her opponent. The winner fucks the loser with the biggest dildo our strap on can handle. Loser is humiliated with hand gags, fisting, orgasm denial, hair pulling, spanking face sitting and ass smothering. The loser is fucked so hard in the ass, her asshole is left gaping open.
Savannah Fox, London River, Penny Barber - Hard Humiliation and Incredible Sex (Everything Butt) (2020 | HD)

2 Butt sluts get Fisted & 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.
Seth Gamble, Penny Barber, Isabella Nice - Hard Torture and Pain from Wild BDSM Sex (FamiliesTied) (2020 | HD)

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, Kendra Spade, Rob Piper - Hard BDSM Orgy Merciless (FamiliesTied) (2020 | HD)

MILF Agent Botches Undercover Anal & 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, Mickey Mod - Hard and Wildly Fucked in BDSM (EvolvedFights) (2020 | HD)

“Mommy” MILF Penny Barber takes on BBC Penny Barber is everyone’s favorite Taboo Fetish MILF. She’s a tall Brunette with big lactating tits and strong legs that can crush any creature who dare to step into her trap. Mickey Mod is a studly Ebony man with BBC that will make you submit to it just by looking at it. Mickey has some training in Hapkido and is confident that his abilities on the Mat will dominate over Penny Barber who seems to be a one-trick pony. Penny likes to pull guard which in Evolved rules, is not great since it does put her shoulders on the mat for a pin which gives favor in the Judge’s eyes to her opponent who is able to Pin her. However, Penny pulls guard and uses her giftwrap move to hold her opponent, sweep him and generall have her way with him. Mickey has really good stregth and he’s really great at being a pervert so he is able to get some great moves on Penny. He has a good strategy for the match. When Penny gets “penalties” on him, he eats her pussy good in order to get her close to orgasm. He knows that if he can get her to cum in the 3rd round, he will get an instant victory and be able to dominate her. After 3 hard fought rounds, the winner is announce to take their prize. The winner spanks the loser, and rubs their feet all over them. The winner fucks the loser good and hard until Penny is cuming over and over then Mickey finally cums and shoots his hot load deep into mommy’s pussy with an incredible creampie ending.
Penny Barber - Sam Solo (EvolvedFights) (2020 | FullHD)

Everyone’s favorite Mother is back on the mats. A real authentic MILF with supple breasts and a mouth that would make a sailor blush, Penny Barber is here today to squash a little man. Sam Solo is pretty pissed off after his last loss. He works extensively with Penny Barber and vows to beat her and put her in her place for all the embarrassment she has put him through. Sam has been watching Penny’s moves and taking notes. He knows she has a history of having orgasms on the Mats so he’s hoping this will happen in round 3 so he can get is Instant victory. Penny Barber doesn’t mess around in this match. Take a look at their arm wrestling match once it uploads. You see Penny resort to cheating by spitting into Sam’s eyes to distract him from arm wrestling! She wants to win at all costs and as the adage goes ” If you’re not cheating, you’re not trying”. Penny shows no honor in this match. She pounces on Sam and gets him to tap over and over again in the first round. In the penalty she makes him take her fingers in his ass even though he appears to be reluctant to them….but in they go, grinding away at his pure little ass. Sam is smart and has a good strategy? will it work? Will Sam get…
Ariel X, Penny Barber - Lesbian Nuru Massage with Penny Barber and Ariel X (SUBMISSIVE X) (2019 | HD)

Ariel X has signed up for a Nuru Massage with sexy, curvey MILF Penny Barber. The clothes come off, the oil goes on and hot lesbian passion ensues. Penny rubs her body all over Ariel’s body, they kiss passionately. Penny uses everything she has to release ariel. in order to get deep into the muscles without the client jerking around, Penny ties up Ariel in rope bondage to get extra deep. Penny puts all her finger inside ariel and the fucks her ass with a strap on