shy love,Penny Barber in 'Kink' - shy love and Penny Barber (Whipped Ass)

Penny is a very cute natural looking girl who loves pain, multiple orgasms, anal sex, bondage and roleplay. In this scene, she goes to her supervisors office to ask for a raise. Shy Love is her beautiful and sadistic boss who wont give her a raise without sexually humiliating Penny. Featuring spanking, amazing ass licking, foot fucking, anal strap-on and more.

Released : July 15th, 2005
Tags : Anal, BDSM, Bondage, Brunette, Corporal Punishment, Dominatrix, Facesitting, Fake boobs, Femdom, Fingering, Glasses, High Heels, Humiliation, Lesbian, LezDom, Mixed, Multiple orgasms, Natural boobs, Nylons Stockings, Pain, Pussy Eating, Rimming, Shaved, Slave, Spanking, Straight, Strap On, Sub, Toned, Vaginal Penetration, White

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Scenes from other sites featuring shy love,Penny Barber

Haley Spades in 'Slutty Cheerleader Caught Mid-Plot'

Haley Spades - Slutty Cheerleader Caught Mid-Plot

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!

Penny Barber in 'Seductive MILF Penny Shares A Cock With Rissa'

Penny Barber - Seductive MILF Penny Shares A Cock With Rissa

A fashion photographer knows how to bring out the sex appeal in her young subjects.

Penny Barber in 'Nympho MILF Massage'

Penny Barber - Nympho MILF Massage

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 in 'Cock Worship'

Penny Barber - 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 Barber in 'Gorgeous Gusher'

Penny Barber - 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 in 'Tiny But Mighty'

Penny Barber - 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 in 'Spanking Mommy's Ass in Strict Bondage'

Penny Barber - 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 Barber in 'Cock-Hungry MILF Penny Goes Airtight In Gangbang'

Penny Barber - Cock-Hungry MILF Penny Goes Airtight In Gangbang

A fast older woman seduces a young rideshare driver.

Penny Barber in 'Compilation: Perfect Bodies'

Penny Barber - Compilation: Perfect Bodies

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 in 'Mommy's Cock-Hungry Hole'

Penny Barber - 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 Barber in 'Teaching My Stepson How Not To Be A Cuck - S24:E2'

Penny Barber - Teaching My Stepson How Not To Be A Cuck - S24:E2

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.They begin with Max kneading Penny's nice titties and fondling her nips. Then Penny tells him that stepmommy is gonna teach him how to make a woman cum. A second later, Max is face first between Penny's thighs as he eats her out. Penny rewards Max for being a very good stepson by sucking his dick and promising him even more as his dad watches.Peeling off her remaining clothes, Penny climbs on the D and sinks down in reverse cowgirl so she can watch her husband watching her as she bangs her stepson. On her knees, Penny continues to maintain eye contact with hubby while taking it in doggy. She gets on her back and spreads her thighs so Max can give stepmilf a creampie, which is when Max suggests he's going to go to his mom's place for the night.

Penny Barber in 'They're Horny, They're Pervy, and They're in Control'

Penny Barber - They're Horny, They're Pervy, and They're in Control

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 in 'MILF Phoenix Rides Pussy-Hungry Pennys Face'

Penny Barber - MILF Phoenix Rides Pussy-Hungry Pennys Face

Two statuesque MILFS, one bed full of cash. When Penny and Phoenix party, the thrills don't come cheap, but they do come often.

Penny Barber in 'Horny Milf In The Wild'

Penny Barber - Horny Milf In The Wild

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 in 'Concept: Virgin Mommy'

Penny Barber - Concept: Virgin Mommy

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 in 'vs Carissa Montgomery'

Penny Barber - vs Carissa Montgomery

Please welcome Carissa Montgomery the MILF Mistress who comes to take on everyone?s favorite ?Mother? Penny Barber. Penny is Laughing at this new MILF calling her out. There can only be one MILF winner today and both these MILFS seem to think they are going to win. Carissa has wrestled before, it?s not like she?s a brand new rookie. Penny Has been wrestling since she was 19 and has taken on and learned from elite sex fighters like Mistress Kara, Dee Williams, Cheyenne Jewel and Professor Ariel X. Carissa is able to reverse some of Penny?s moves and somehow avoids Penny?s signature gift wrap. Carissa also has some amazing pussy licking skills which could put the orgasmic Penny Barber into some trouble. This match is exciting MILF sexual tension for three full rounds with fingering so hard and fast it looks like an orgasm is going to end round 3 just a little early but can these MILFs make it happen? The winner gets to put on her strap on and face fuck the loser. The winner verbally humiliates the losers with obnoxious trash talk. The winner fucks the loser?s pussy then gets into a lesbian scissor fucking position and trib fucks the loser until the Winner gets her power orgasm. The loser?

Penny Barber in 'Fuck Around and Find Out'

Penny Barber - 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.

Ashley Lane in 'Penny Trains Pet, Ashley'

Ashley Lane - 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!

Penny Barber in 'Domme Mommy Penny Barber Punishes Boy Toy While Hubbys At Work'

Penny Barber - Domme Mommy Penny Barber Punishes Boy Toy While Hubbys At Work

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.

Penny Barber in 'Two For Tennis, Three For Fucking'

Penny Barber - Two For Tennis, Three For Fucking

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.

Penny Barber in 'Professor Penny Barber Takes Every Inch Of Students BBC'

Penny Barber - Professor Penny Barber Takes Every Inch Of Students BBC

Professor Penny Barber Takes Every Inch Of Student's BBC

Rachael Cavalli in 'Muscle Mommies Compilation'

Rachael Cavalli - Muscle Mommies Compilation

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!

Penny Barber in 'Dirty Divorcée Gets All Oiled Up'

Penny Barber - Dirty Divorcée Gets All Oiled Up

Penny Barber is a pissed off ex-wife who needs a little relief from battling her husband and his lawyers all day. A message will do the trick! Vince Karter's strong hands are almost the touch she needs, oiled up and horny Penny is in the mood for something more. What would be better than a stiff, hard dick? that's right, recording it all to rub it in her ex's face.

Penny Barber in 'Naughty MILF Penny Risks It All For Two Thick BBCs'

Penny Barber - Naughty MILF Penny Risks It All For Two Thick BBCs

Penny is happy to have an affair, but she isn't willing to risk getting caught for a chance at some dick. For a chance at two dicks, on the other hand...

Penny Barber in 'Pretty In Pink'

Penny Barber - 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 Barber in 'Sticky Situations'

Penny Barber - Sticky Situations

What's up, TeamSkeet fans? Remember those good ol' days when you woke up with a messy load in your undies after one wild dream? What if we told you we had an extra hot scene about it a while ago and that it will make you cum just like when you were a teen? Published on June 6th, 2021, on the PervMom series, it features Penny Barber, one of the sexiest and boldest stepmom in our roster. You gotta sympathize with Robbie, her stepson, who keeps waking up all covered in his cum after dreaming of humping her. Penny knows the boy fantasizes about her, and her sweet jugs, so one morning, noticing the creamy liquid over his young body, she comes into his room to 'give him a little training' on how not to wet the bed like that. Sitting on her stepson's cock, Penny shows him how to save his wad for a better purpose. Craving to feel Robbie's man juice inside of her, she rides that dick until Robbie can't help but stuff her up. The next day, Penny is hungry for cum once more, so she gives Robbie a talk about his future with the ladies. She tells him that he needs to learn how to please a woman if he wants to get a girlfriend–the perfect excuse to have a creamy breakfast, courtesy of her stepson. As she drinks up, she looks at Robbie sassily, knowing that he'll never hear the end of it. Now a true fan of her stepson's cum, Penny surprises him by jerking off and decides to dive into her boy's fantasies. It's time for her to surprise him now with a provocative dress and thirst for cum that won't be quenched until he shoots every drop inside her luscious pussy.

Penny Barber in 'Swinger Set'

Penny Barber - Swinger Set

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!

Penny Barber in 'wants the married AC repair man to check her temperature'

Penny Barber - I Have a Wife

Penny Barber's AC is on the fritz, so she has Will the AC repair man stop by to fix it. She's also hoping he could take care of her wet MILF pussy. Even though Will confesses he's married and is flattered at her advances, she leaves him with the temptation to join her in the bedroom. She steps away into her bedroom and slips into some lingerie. As she moans while masturbating alone, Will can't help but peek his head in... just to have a look. It's way too hot for him to handle so he lends her a hand and his big cock instead of sitting on the sideline watching.

Penny Barber in 'Tasty MILF Is Hungry For Young Studs Cock'

Penny Barber - Tasty MILF Is Hungry For Young Studs Cock

Penny is the perfect mom, and all of her son's friends want to taste what she whips up. When one of them gets a moment alone with her, he sees an opportunity to slip his hand in her cookie jar.

Penny Barber in 'My Friend's Hot Mom'

Penny Barber - My Friend's Hot Mom

Penny Barber is on a little vacation like usual. The only thing different is this time her son's friend Tyler came along. Lucky for him he's feeling under the weather and gets to be pampered by his friend's hot-ass mom. When she proceeds to check his temperature, man o' man does it start to get HOT with her nice set of big round tits so up close. The only way to cure Tyler is to stroke his swollen cock until all that built-up pressure is released.

Becky Bandini in 'Dripping Pussys Compilation'

Becky Bandini - Dripping Pussys Compilation

Hey, TeamSkeet fans! We know you were yearning for this collection, so the wait is over! Join Becky, Harlowe, Julia, and Penny as they get their pussies all wet and dripping. You won't believe how much these chicks can squirt in this hot compilation.

Shy Love in 'Housewife 1 on 1'

Shy Love - Housewife 1 on 1

Shy Love's been reliving her college party days. To keep her husband happy she's going to give it the "ole college try" in the sack! Shy knows the way to her man's heart is thru his cock and she's going to tug, suck and fuck every bit of it!

Penny Barber in 'Cock Hungry Realtor Cant Resist Hard Dick'

Penny Barber - Cock Hungry Realtor Cant Resist Hard Dick

Every realtor has tricks up her sleeve for selling a hot property. Penny knows appearances are everything, and personally believes it's good luck to consummate a listing.

Penny Barber in 'Jizz Pancakes for Lewd Mommy's Breakfast'

Penny Barber - Jizz Pancakes for Lewd Mommy's Breakfast

Mommy is the most important thing in any girl's life. A mother gives a girl life, so in return she can give a mother the most precious thing. But this is only in theory. What if Mommy wants to ride on a girl's boyfriend's hard cock? What if she wants to take away her daughter's most precious possession: her future husband? Mommy also understands that it is very difficult to make such decisions, and so she acts without warning, without permission, and in complete submission to her lust...

Penny Barber in 'MILF Deals With a Couch Humper'

Penny Barber - MILF Deals With a Couch Humper

Dark-haired Penny Barber has invited Van Wylde for a much-needed booty call, but her house guest, Eva Nyx, is proving to be a problem! Blonde Eva is uncontrollably horny and loves to hump the living room furniture. Dominant Penny tells Eva to behave but before she knows it, mischievous Eva is spying on Penny and Van having sex on the couch! Eva crawls on top of the couch and sneakily humps to her heart's delight. When Eva is caught, Penny drags her in for a cum-filled threesome and Van gets the ride of his life!

Penny Barber in 'Waking Dream'

Penny Barber - Waking Dream

Waking Dream

Aaliyah Love in 'Deep Analysis: A Swap Movie'

Aaliyah Love - Deep Analysis: A Swap Movie

The Von Skeets are a cunning family and use their prosperity and charm to allure everyone around them. Jack and Penny are the heads of the household and work as psychologists known for their unconventional methods. They have a ravenous appetite for sex and love everything kinky and taboo. Then there is Theodora and Tyler, stepsiblings with the same sexual appetite as their stepparents – but Theodora and Tyler might be even more insatiable for pleasure. Close by are the Badcoxx, another well-to-do family. Aaliyah and Calvin's marriage is falling apart, and all they seem to do is argue anymore. Their stepkids, Coco and Josh, just want things to return to normal. When Theodora and Tyler meet Coco and Josh, they are immediately smitten with lust. Soon, they do everything in their power to seduce the other stepsiblings and corrupt their virgin minds. Coco and Josh are easily swayed and caught in the Von Skeets' plan. Tyler fucks Coco hard, and Theodora eagerly takes everything Josh has to offer. The four teens then swap, so it's raunchy stepsibling-on-stepsibling sex. Soon after, Aaliyah and Calvin receive a mysterious flash drive. It contains hidden camera footage of Coco and Josh fucking in the Von Skeets' pool. Mortified, Aaliyah and Calvin confront the Von Skeets, attempting to get to the bottom of this footage. Bewildered, Jack and Penny assume that their butler, Jay, must be the culprit and fire him on the spot. The Von Skeets assure the Badcoxx that the footage will never see the light of day. But their coyish plot does not end there, and Jack and Penny convince Aaliyah and Calvin to begin therapy. They agree, albeit skeptically, which sets the Badcoxx down a dark and intimate path of self-discovery. Everything quickly changes, and soon everyone gives in to their deep and unquenchable lust. See Aaliyah, Coco, Penny, Theodora, Calvin, Jack, Jay, Tyler, Josh, Freya, Link, London, Ophelia, and Rusty like you've never seen them before! This brand new feature-length Team Skeet Premium movie pushes the boundaries of all things taboo…

Penny Barber in 'Tumble'

Penny Barber - Tumble

A silent seduction plays out in plain sight in a 1950's laundromat.

Penny Barber in 'Concept: Tales of Taboo 2'

Penny Barber - Concept: Tales of Taboo 2

What's up, Mylf lovers? For this Labs update, we're bringing back a successful experiment, Tales of Taboo. In this episode, orphaned step-siblings Reese and Tyler are 18 and ready to be on their own. But before they can go out on their own, they'll have to stay with Penny, who is very strict and demanding of the two. When Tyler and Reese decide to rebel against Penny, she lays down the law and has the two stepsiblings fuck her as hard as possible. Tyler has his work cut out for him to keep both Reese and Penny pleased, but Penny won't accept failure as an option.

Penny Barber in 'Concept: Tales of Taboo 2'

Penny Barber - Concept: Tales of Taboo 2

Whats up, TeamSkeet fans? For this Labs update, were bringing back a successful experiment, Tales of Taboo. In this episode, orphaned step-siblings Reese and Tyler are 18 and ready to be on their own. But before they can go out on their own, theyll have to stay with Penny, who is very strict and demanding of the two. When Tyler and Reese decide to rebel against Penny, she lays down the law and has the two stepsiblings fuck her as hard as possible. Tyler has his work cut out for him to keep both Reese and Penny pleased, but Penny wont accept failure as an option.

Penny Barber in 'Suite After-Party'

Penny Barber - Suite After-Party

Armani and Penny put on their sexiest dresses to attract attention tonight, but when Penny gets more than she counted on, Armani's not sure she can lend a helping hand. Or maybe she's just afraid neither of them will be able to walk tomorrow...

Penny Barber in 'The Naughty Naudi Teacher Feature'

Penny Barber - The Naughty Naudi Teacher Feature

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.

Alura Jensen in 'The Best of Bad Milfs'

Alura Jensen - The Best of Bad Milfs

Everyone loves a milf, so for this Team Skeets Selects update, we've put together some of our favorite Bad Milf moments. You won't want to miss out on this ultra star-studded compilation, filled with the hottest mature women and their young counterparts getting fucked hard.

Aria Carson in 'Babes Riding Dicks'

Aria Carson - Babes Riding Dicks

Enjoy this compilation of the hottest babes like Aria Carson, Dani Blu, Lolly Dames, Penny Barber and more as they show off their naughty skills while riding dick like pros!

Penny Barber in 'Concept: ASMR'

Penny Barber - Concept: ASMR

By now, you've likely heard of 'ASMR,' an internet phenomenon that involves sensory stimulation via highly focused audio. Well, people have come to love ASMR worldwide, so MYLF decided it was time to try it out ourselves. Penny Barber plays the seductive nurse in this experiment, and Mike Mancini is the fortunate patient. Through years of experience, Penny will make sure Mike's check-up goes swimmingly and that by the end of their sessions, he is in perfect shape.

Penny Barber in 'Modern Cowgirl 2022'

Penny Barber - Modern Cowgirl 2022

The stunning Penny Barber is Mylf Of The Month for January here at Mylf.com! Dressed in her best cowgirl attire she shares some of her future plans for 2022 before lucky stud Ryan Mclane joins her in bed. Penny will ride Ryan's cock like the naughtiest cowgirl she is until she gets a delicious creamy load of cum all over her gorgeous face!

Gianna Dior in 'Best Sluts of 2021'

Gianna Dior - Best Sluts of 2021

Enjoy this steamy compilation of the naughtiest babes of 2021 featuring gorgeous sluts such as Ashley Wolf, Gianna Dior, Penny Barber, Tristan Summers and more as they get down and dirty in the most sensual ways.

Milan in 'fucking in the bedroom with her tits'

Milan - fucking in the bedroom with her tits

Milan is the luckiest milf in the world. Her husband Kurt has planned the most special night for them, including champagne, strawberries, a blindfold, and surprise ... her best friend Shy Love. Now that's a party. And yeah ... that Kurt's one lucky guy.

Shy Love in 'fucking in the couch with her tits'

Shy Love - fucking in the couch with her tits

Shy Love thinks Cheyne's wife is crazy, because, if she's not fucking Cheyne, then she must be crazy. Cheyne is hot, and if his wife isn't fucking him, then Shy soon will be. Poor Cheyne ... stuck with the crazy wife when his neighbor is the smokin' hot Shy Love.

Shy Love in 'Wife Shy Love fucking in the bedroom with her piercings'

Shy Love - Wife Shy Love fucking in the bedroom with her piercings

Shy Love's been reliving her college party days. To keep her husband happy she's going to give it the "ole college try" in the sack! Shy knows the way to her man's heart is thru his cock and she's going to tug, suck and fuck every bit of it!

Shy Love in 'Wife Shy Love fucking in the desk with her petite'

Shy Love - Wife Shy Love fucking in the desk with her petite

Shy Love has come to see her husband at the office, he is really hungry and is mad that she didn't bring him anything to eat. Well maybe she can give him desert by fucking him, that sounds pretty good to him.

Shy Love in 'Stranger Shy Love fucking in the couch with her tits'

Shy Love - Stranger Shy Love fucking in the couch with her tits

Matt has built himself quite a reputation with the cleaning service. It's to the point where the only thing getting cleaned anymore is his cock! Aye que buena!

Shy Love in 'fucking in the living room with her big ass'

Shy Love - fucking in the living room with her big ass

Her husband is not taking her out enough and not treating her right, so she decides that letting his friend fuck her will help to ease her sexual tensions.

Aria Carson in 'Stepmom Knows Best'

Aria Carson - Stepmom Knows Best

Aria Carson confides in her stepmom Penny Barber that her 1 year anniversary with her boyfriend Jay Romero is coming up, but she's not sure if they'll end up fighting or finally fucking. Penny tells Aria to bring Jay to the bedroom and she'll take care of the rest. Later, Jay is sitting on Aria's bed and when she blindfolds him he knows they're about to have sex, but what he wasn't expecting was Aria's hot stepmom to be involved as well!

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

Penny Barber - 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 Barber in 'Concept: Perv Therapy'

Penny Barber - Concept: Perv Therapy

What is Perv Therapy? It's when individuals get sent to therapy to work through their problems and things get sexual with the shrink. In today's update, stepsiblings Tristan Summers and Jay Romero get sent to do a therapy session with Dr. Penny Barber after their stepmom caught them doing inappropriate things together. Dr. Barber lets them know that she'll be recording the session and starts getting them to open up to her. After Dr. Barber encourages them to do a little reenactment, pretty soon things get naughty between the stepsiblings and Dr. Barber joins in! Who knew that therapy could be so satisfying?

Penny Barber in 'Concept: Perv Therapy'

Penny Barber - Concept: Perv Therapy

What is Perv Therapy? It's when individuals get sent to therapy to work through their problems and things get sexual with the shrink. In today's update, stepsiblings Tristan Summers and Jay Romero get sent to do a therapy session with Dr. Penny Barber after their stepmom caught them doing inappropriate things together. Dr. Barber lets them know that she'll be recording the session and starts getting them to open up to her. After Dr. Barber encourages them to do a little reenactment, pretty soon things get naughty between the stepsiblings and Dr. Barber joins in! Who knew that therapy could be so satisfying?

Carissa Montgomery in 'Busty MILFS in Competitive Erotic Wrestling'

Carissa Montgomery - Busty MILFS in Competitive Erotic Wrestling

Please welcome Carissa Montgomery the MILF Mistress who comes to take on everyone's favorite 'Mother' Penny Barber. Penny is Laughing at this new MILF calling her out. There can only be one MILF winner today and both these MILFS seem to think they are going to win. Carissa has wrestled before, it's not like she's a brand new rookie. Penny Has been wrestlings since she was 19 and has taken on and learned from elite sex fighters like Mistress Kara, Dee Williams, Cheyenne Jewel and Professor Ariel X. Carissa is able to reverse some of Penny's moves and somehow avoids Penny's signature gift wrap. Carissa also has some amazing pussy licking skills which could put the orgasmic Penny Barber into some trouble. This match is exciting MILF sexual tension for three full rounds with fingering so hard and fast it looks like an orgasm is going to end round 3 just a little early but can these MILFs make it happen? The winner gets to put on her strap-on and face fuck the loser. The winner verbally humiliates the losers with obnoxious trash talk. The winner fucks the loser's pussy then gets into a lesbian scissor fucking position and trib fucks the loser until the Winner gets her powerful orgasm. The loser is left laying on the ground with the perfect huge tits out.

London River in 'Best Creampies given and taken in the prize round on Evolved Fights'

London River - Best Creampies given and taken in the prize round on Evolved Fights

Today we bring you a compilation of all of the greatest creampie endings we have seen on Evolved Fights. Here at Evolved Fights, The winner gets to do whatever he or she wants to do to the loser. One of the most humbling things a winner can to as a female winner is to drain your opponent of their seedwhether they want it or not. For a Man, planting his seed inside his prize is the Ultimate victory. We have over an hour of footage of vaginal cream pies and one anal creampie ending for your enjoyment.

Penny Barber in 'vs Leya Falcon'

Penny Barber - vs Leya Falcon

Leya Falcon is doing her first try at wrestling for Evolved Fights Lesbian Edition. She is taking oneveryone's favorite MILF, Penny Barber. Penny Barber is the best Wrestler mommy for a new girl to startwith because she's sexy, slutty and talks more shit than any other wrestler on our roster. If you can last amatch with the torment that Penny dishes out, you can last a match with anyone. Leya puts up a goodfights but let's face it, Penny destroys her in the wrestling rounds. The way our rules are set up, ifsomeone orgasms in the 3rd round, they lose. So Leya is planning on taking it easy the first two roundsand then pouncing on Penny in round 3 and making her cum. If you have followed Penny's wrestlingcareer, she has a weakness for ladies and she does have a tendency of cumming on the mats. Round 3is anyone game even though rounds 1 and 2 where total domination by Penny Barber using her gift wrap, face sitting and leg scissors. The Winner gets to use the REAL COCK to fuck the loser. The loser mustgive the winner a foot job and then give up the ass. The loser is fucked so hard her asshole gapes wideopen and we get a good look of what losers are made of.

Penny Barber in 'Feminist Assassin Enslaves Colby Jansen'

Penny Barber - Feminist Assassin Enslaves Colby Jansen

Colby Jansen committed a financial crime that robbed money from a feminist organization. He's at home, bragging to his buddy on the phone about it when Penny Barber appears in his kitchen, looking for justice.Penny tells Colby that she is going to get everything she needs to get her organization's money back, and he's going to give it to her. Her methods are a mix of seduction, ball squeezing and keeping Colby on the edge of orgasm until he breaks and tells her how much he stole, where his safe is with all the evidence, and the combination.While she's working on him he begs her to stop squeezing his balls. She sucks and strokes his cock along the way also making him beg to cum. "If you tell me what I want, I'll fuck you...","I've done this before, you'll break eventually..."She sucks the cum out of his cock then crushes his balls in hand putting him out.Colby Jansen comes to in his living room laying over a weight bench. Penny Barber is standing over him with a pink strap-on cock on. "I told you I'd fuck you if you gave me what I wanted..."Colby begs her not to fuck his ass. She smiles and makes a deal with him. "I could get the police involved, have you arrested, and put in prison where you'll get your ass fucked every day by sweaty inmates, or...,You can just take my cock right now. I'll take you back to our feminist compound where we keep bad boys like you to be used forever for whatever we desire..."Colby has no choice. He doesn't want to go to prison. Before he can decide she slides her cock inside him. At first it hurts, but he soon starts to enjoy it. "Come on Colby! What's it going to be? Get fucked by me and my feminist friends or get fucked by Bubba in prison?"He eventually breaks and agrees to leave his life and come with her to be a sex slave.Weeks have passed. Colby is laying naked in the feminist compound awaiting his next task. Penny struts into the room. She wants to use his mouth and dick to make her cum a few times.She rides his face in her pantyhose and miniskirt, then rips her pantyhose open and places her wet pussy on his tongue. Penny has a few big orgasms, then tells him she needs his cock."You can't cum Colby. If you do, I'm having you assigned back the strap-on line up. I've got a line of dominant women eager to use their new gigantic strap-on cocks on you. You don't want that, but I'd actually enjoy watching..."Penny orders Colby to fuck her hard. He tries as hard as he can not to cum while fucking her hard from behind. Every time he has to stop fucking her to keep from cumming she yells at him to keep going. Eventually he can't take it anymore and explodes a load of cum all over her torn pantyhose covered thighs."Looks like you're about to get your ass fucked..."Penny smiles and leaves him to await his next task.

Bella Rossi in 'Old school Wrestlers in Nude Wrestling'

Bella Rossi - Old school Wrestlers in Nude Wrestling

Ariel X and Bella Rossi are doing a competitive sex fight. They both have great experience which isdisplayed in their match with amazing holds. The action is back and forth as both girls try to get theiropponent to cum. In round 3, both girls are allowed to wear strapon cocks in an attempt to penetrate theiropponents to try to get the "instant victory" via "Orgasm on the Mat." One of these wrestlers completelydominates the other with brutal humiliating holds. The winner is allowed to do whatever she wants, andtoday the loser wants to fuck the loser hard and fast, making her cum over and over. The winner lifts andcarries the loser and throws her into one sex position to the next completely having her way with her.

Valentina Paradis in 'Club Filly'

Valentina Paradis - Club Filly

Milf Shy Love is on the hunt for sexy girls at Club Filly. She spots Kat Arina and Valentina dancing. Shy decides to seduce the girls into passionate threesome sex inside the club. Horny Kat and Valentina pleasure Shy's ass and pussy. Then Shy fucks both girls at the same time, leaving them happy.

Penny Barber in ''Mommy' MILF Penny Barber takes on BBC'

Penny Barber - '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 andstrong legs that can crush any creature who dare to step into her trap. Mickey Mod is a studly Ebony manwith BBC that will make you submit to it just by looking at it. Mickey has some training in Hapkido and isconfident 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 matfor a pin which gives favor in the Judge's eyes to her opponent who is able to Pin her. However, Pennypulls guard and uses her giftwrap move to hold her opponent, sweep him and generall have her way withhim. Mickey has really good stregth and he's really great at being a pervert so he is able to get somegreat moves on Penny. He has a good strategy for the match. When Penny gets "penalties" on him, heeats her pussy good in order to get her close to orgasm. He knows that if he can get her to cum in the 3rdround, he will get an instant victory and be able to dominate her. After 3 hard fought rounds, the winneris announce to take their prize. The winner spanks the loser, and rubs their feet all over them. Thewinner fucks the loser good and hard until Penny is cuming over and over then Mickey finally cums andshoots his hot load deep into mommy's pussy with an incredible creampie ending.

Bella Rossi in 'Hungry Amazons Part 2. Horny Amazons Tenderize Ass Meat'

Bella Rossi - Hungry Amazons Part 2. Horny Amazons Tenderize Ass Meat

Ariel X is still captive in the jungle. Nikki Delano found Ariel a while back and she liked playing with her so much, she has decided to keep her tied up for all the tribe members to take their turn with her. Today two of the sexiest more horny amazons have their turn with Ariel. They begin by tenderizing her meat with flogging and stretching. Ariel is on her tippy toes being held up on a sharp wooden block by her pussy. The girls lick and kiss her to taste the salt on her. Then they get her down and take turns licking her pussy and then feeding their pussies to her. Finally, both girls come in with a strap on cocks and use every hole Ariel X has. She is DP'd with both their strap on cocks until she cums and then she is left there for the next tribe member to take his or her turn.

Ariel X in 'Lesbian Nuru Massage with Penny Barber and Ariel X'

Ariel X - Lesbian Nuru Massage with Penny Barber and Ariel X

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

Penny Barber in 'MILF Agent Botches Undercover Anal and Sacrifices Step-Daughter'

Penny Barber - 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 in 'Tight Bodied Teen Star and Anal Step Mommy Fuck Director's Huge Cock'

Penny Barber - 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 in 'vs Mistress Kara'

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 in 'vs Johnny Starlight'

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.

Savannah Fox in '2 Butt sluts get Fisted and Fucked'

Savannah Fox - 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.

Penny Barber in 'Cock Crazed Step-Mommy Just Wants Anal For Christmas'

Penny Barber - 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.

Moka Mora in 'Hot Spoiled Princess and Anal Step-Mommy Earn Their Keep'

Moka Mora - Hot Spoiled Princess and Anal Step-Mommy Earn Their Keep

Curvy Mommy Penny Barber is busy cleaning the house for long lost Uncle Ramon's arrival and scolding her hot little piece-of-ass step-daughter for being a brat. Both ladies think that uncle Ramon is simply visiting to straighten out a small mistake in the will, not knowing that his brother did actually leave him everything, including them. He immediately starts by retracting the family Porsche from spoiled little princess Moka and makes her earn back the right to even touch the car. An over the knee spanking and flogging help her get the picture Soon she has a cute little shocked expression as she gets on her knees, handcuffed, to suck dick and get fucked with tight nipple clamps, gently kissing the bumper of the car that used to be hers.After putting Moka back in line he heads right upstairs to let the secretly submissive housewife Penny Barber know that Daddy is back in charge. Throwing her over the sink, he beats her ass red with a wooden spoon and instructs her in how she can keep paying the rent with her bouncy tits, wet mouth, and hot jiggly ass. Clamps on those big luscious tits, and a sold face fucking on the kitchen floor get's Penny's pussy wet, and soon she is begging to cum against the kitchen counter with her apron above her hips. Ramon shoves his thick cock in her ass sending her over the edge into screaming orgasms that she endures further humiliation and beatings to get. Moka discovers them there, and embarrassed yells at her Step-Mommy, only to be reprimanded by both Ramon and Penny.Moka is placed in a tough standing suspension and made to suck and fuck as Penny places strip after strip on her coed ass for calling her a whore. Drooling and begging and screaming apologies Moka does her best to remain composed, but eventually has to cum and does so with her feet lifted in a full suspension. After promising to be a good girl she is let down and allowed to take her Mommy's fist and lick up her Uncle's cock fresh out of Penny's hungry ass.

Penny Barber in 'MILF vs Cowgirl'

Penny Barber - MILF vs Cowgirl

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.

Mona Wales in 'Close Match. One wrestler almost makes a cum from behind victory'

Mona Wales - Close Match. One wrestler almost makes a cum from behind victory

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!

Ariel X in 'Bondage Wrestling Exhibition Match with Ariel X and Penny Barber'

Ariel X - Bondage Wrestling Exhibition Match with Ariel X and Penny Barber

To Penny Barber's surprise, Ariel X decided to turn this match into a play bondage game. We all knew Penny Barber wouldn't stand a chance against Ariel X so we needed to make things a little more interesting. Ariel doesn't use old boring rope to tie up her victim, Ariel uses Penny's arm and ankle bands to restrain her victim. She even gets Penny Barber into a legit Hogtie which makes Penny cry mercy. This is a no holds barred match for real! Anything goes and when we say that we mean, any thing goes into Penny Barber's Va-giant vagina. Ariel Plugs Penny's pussy with the hitachi head then makes her worship her muscles. Lift and Carry at the end of the video demonstrates how Ariel X is the GREATEST OF ALL TIME!

Penny Barber in '2017 Mom's I'd like to Fight ( MILF) mini tournament'

Penny Barber - 2017 Mom's I'd like to Fight ( MILF) mini tournament

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.

Savannah Fox in 'Savanna Fox and Penny Barber fight and fuck in a rubber match'

Savannah Fox - Savanna Fox and Penny Barber fight and fuck in a rubber match

Penny Barber and Savanna Fox have gone back and forth on winning and fucking each other. Penny Barber won one match then Savanna fox won a match. This rubber match will finally decide who the meanest bitch is. Who ever wins gets to fuck the loser with the biggest cock Ultimate Surrender has ever seen. Loser is fucked and humiliated like ever before.

Penny Barber in 'Discipline for Mommy's Little Anal Slut'

Penny Barber - Discipline for Mommy's Little Anal Slut

Penny Barber had one little problem: her out of control little slut step daughter Mercy West. Using her perfect MILF body and uncontrollable sex appeal to bring Mercy's punk boyfriend on board for disciplining Mercy, she get's a little more than she bargained for. After having her juicy round ass spanked a deep red, clamped, flogged, and controlled by Xander's thick cock, she leaves Xander with a few tools to persuade Mercy with: handcuffs, wax, and a dress for her little princess to where to tea. All lines of dominance eventually meet in confrontation when Mercy starts acting up again, resulting in Xander and Penny teaming up to get that pretty little punk covered in cane marks and her boyfriends huge dick in her tiny virgin ass. With the newly minted little angel lapping at Mommy's cunt full of her boyfriend's dick, Mercy learns what it's like to really earn some cum.

Sophia Grace in 'Season 14 is the season of Rookie Destruction'

Sophia Grace - Season 14 is the season of Rookie Destruction

Penny Barber destroys the rookie, makes her cum and makes her submit

Lisa Tiffian in 'So close yet So far, One team blows their chances and gets fucked hard'

Lisa Tiffian - So close yet So far, One team blows their chances and gets fucked hard

Losing Team Captain is fisted by her own team mate. Losers are fucked good and hard in front of a live audience

Daisy Ducati in 'Wrestler Utterly Destroyed on the mats, Gets fisted and fucked in ass'

Daisy Ducati - Wrestler Utterly Destroyed on the mats, Gets fisted and fucked in ass

This tournament is too much for one wrestler. The wrestler quits after 2 rounds and gets fisted first thing in the Prize round. The winner takes the loser's Asshole and verbally and sexually brutalizes her.

Sami Price in 'Penny Barber Summons Baphomet to seek revenge on Mother Superior'

Sami Price - Penny Barber Summons Baphomet to seek revenge on Mother Superior

Penny Barber has been caught drawing tits and ass and pussy AGAIN by mother superior. Mother has had enough of Penny's defiance so she is putting her in a dark closet so Penny can repent and reflect on her deeds. Penny wants nothing to do with repenting so in the darkness she draws a pentagram and summons the ancient demon Baphomet. Baphomet arrives to Penny's surprise but she is also very irked to have been dragged away from fucking virgins in hell. Penny tells Baphomet she needs her help to get revenge on Mother Superior. Baphomet will help but Penny must pay with flesh and since Penny smells like a virgin, Baphomet will take the flesh with blowjobs, pussy fucking and ass fucking. When Baphomet is done with Penny, she seals the deal by dropping a hot load on to the rosary that is shoved into Penny's ass after she got a good hard anal fucking

Penny Barber in 'Kajira Bound asks Izamar for Help to get the Bullys who fucked her'

Penny Barber - Kajira Bound asks Izamar for Help to get the Bullys who fucked her

Poor Kajira bound got ruthlessly bullied and fucked by Penny Baber and Lisa Tiffian, the last time she did a tag match with Bella Rossi as team captain Today, Kajira is filling in for Juliette March ( who is out from appendicitis) and she gets to have Izamar Gutierrez as her Team Captain. Their plan is to put Izamar on the mats for most of the match so she can give Penny and Lisa a taste of their own bullying medicine. If they use their tags right, Izamar and Kajira will be fucking the bullies senseless. This is a very close match up and it comes down to the final seconds of the match to determine the winners. Winner fuck the losers in front of a live audience and squirt on to their loser faces.

Penny Barber in 'Poor Kajira gets destroyed by Penny Barber and Lisa Tiffian'

Penny Barber - Poor Kajira gets destroyed by Penny Barber and Lisa Tiffian

It's Lisa's turn to do some bullying in a tag match. Penny and Lisa torment Kajira, trapping her on the mat too far away from her team mate to be able to tag out for help. Bella Rossi does a great job trying to make up points. Bella single handedly takes on the bullies Penny and Lisa to try to take team annihilator to victory.Loser are tied up and fucked hard. Used panties are jammed into their mouths to shut them up. They are blind folded and made to suck cock and take humiliation. Hang gags and brutal fisting

Penny Barber in 'From Carpenters to Lesbians, Aiden Starr makes a lot of things'

Penny Barber - From Carpenters to Lesbians, Aiden Starr makes a lot of things

Penny Barber and Veruca James are hard at work in the shop making a dick on a stick. When Aiden Starr walks in on the girls slacking off, she decides to over dose these fuck ups with fuck ups. Aiden spanks the girls and makes Veruca reluctantly be a lesbian with Penny. While Penny is all for getting to dyke out with Veruca, Veruca is less enthusiastic but Aiden makes her do it anyway. Lots of sloppy ass to mouth. The girls try their asses with the slink, the speculum, fisting and strap ons. Aiden lets the lesbo carpenters use the dick on a stick they made but only if they take it in the ass.

Wenona in 'MILF round Robin Erotic WRestling tournament'

Wenona - MILF round Robin Erotic WRestling tournament

this is the 2016 MILF tournament. We put Moms I'd Like to Fight on the mats to see who is the toughest mommy. Round 1 is Penny Barber vs. Wenona. Round 2 Angel Allwood vs. Penny Barber. Round 3 is Wenona vs. Angel Allwood. Round 4 is Wenona AND Angel vs. Penny Barber.All girls get fucked regardless of if they win or lose. DP acation, Fisting Action. Trib Fucking Action, Spitting and humiliation

Penny Barber in 'Orgasm On the Mat! Penny Barber gets a huge lead in Round 1'

Penny Barber - Orgasm On the Mat! Penny Barber gets a huge lead in Round 1

This match was filmed streaming LIVE. This is 100% real, competitive erotic wrestling. These Sexual wrestling gladiators show us what sex fights are all about. Penny Barber shows us impressive power against our powerhouse, Izamar. Penny Barber takes the lead going into round 2. Izamar must make a move if she's going to win. One of these wrestlers is made to cum on the mats. It is her demise. Too Many Orgasms from the sex fight, leaves one of these girls useless on the mats. Turned into a fuck doll for round 4. Loser is stripped of her colors, face fucked, fisted, and fucked in the ass with an anal strap on. Gaping ass is squirted with Cum.

Penny Barber in 'Battle of the biggest Brats'

Penny Barber - Battle of the biggest Brats

Penny Barber and Juliiette March are the most notorious Brats ever in Ulitmate Surrender history. These two are bitter losers and even more bitter winners. One thing is for sure, who ever wins will utterly humiliate the loser with a true grudge fuck. Loser must submit to a girl who bests her. It sucks getting fucked by someone you despise. Loser cleans off winners dirty feet after she is toe fucked.

Venus Lux in 'Horny Electricians get their hands dirty'

Venus Lux - Horny Electricians get their hands dirty

Penny Barber and Venus Lux are electricians who have been working all day and night. They are tired, exhausted and horny. They can feel the energy between them as Penny Barber foils their night plans by breaking a fuse box. These girls are use to working with their hands and Venus shows us how good she is with her hands by fisting Penny Barber's freshly fucked pussy. Venus finishes Penny off with a good asshole pounding and then busting a nut onto Penny's Glasses.

Mia Li in 'Orgasmic Wrestlers meet on the mats. It's inevitable that One will cum'

Mia Li - Orgasmic Wrestlers meet on the mats. It's inevitable that One will cum

Penny Barber and Mia Li are two of our most orgasm wrestlers on the roster. We are guaranteed to see an orgasm on the mat or so we thought. Seems like Mia Li has been training and she isn't allowing herself to cum on the mats. She even seems to be able to give Penny Barber a little trouble on the mats. When it is evident that these girls are not going to be able to hold each other down long enough to make each other cum, the ref breaks out the magic wand and the wrestler in control gets to use it on a pinned wrestler. Orgasms happen, again and again!!

Megan Rain in 'Up Your Game, Bitch'

Megan Rain - Up Your Game, Bitch

When Megan Rain arrives on set and proceeds to annoy everyone with her unprofessional behavior, it's up to consummate pro and agency head Shy love to come by and straighten the bitch out. After confronting the young starlet, Shy allows Megan to prove her worth with a firm but fair lesbian fuck sesh.

Nerine Mechanique in 'Electroslut Tied, Teased, Fisted, Fucked!'

Nerine Mechanique - Electroslut Tied, Teased, Fisted, Fucked!

Nerine Mechanique electrodominates old friend Penny Barber with the violet wand body plate, a florescent bulb electrode, finger banging, fisting and vaginal and anal strap-on!

Penny Barber in 'Team Tarrasque and Team Grappler Go out with a Bang for season12'

Penny Barber - Team Tarrasque and Team Grappler Go out with a Bang for season12

These Team Captains have been going at it all season long. It's been a back and forth battle all season. Just when one team gets ahead in points, the other team cums from behind and closes the gap. Today the Grapplers come in with less than a 300 point lead. Tarrasque has some strong players on their team tonight and they are hoping to get the victory and give Darling the gang bang she deserves.Round 1 is mona wale and Mia Li for Team Tarrasque taking on Daisy Ducati and Julietter March for Team GrappplerRound 2 is Lisa Tiffian and Yasmine Loven for Team Tarrasque taking on Holly Heart and Angel Allwood for Team GrapplerRound 3 is Penny Barber and Cheyenne Jewel for Team Tarrasque and Darling and Izamar for Team Grappler Round 4 is a brutal gang bang of the losing team. Fucked Hard, Turned into human dildos to be used to make the winner cum. Mutiny for the losing Captain as her team turns on her and gang bangs her. Hard fisting from her team!

Penny Barber in 'Darling takes on Penny in a 2 on 2 tag match for the last time'

Penny Barber - Darling takes on Penny in a 2 on 2 tag match for the last time

this is the last 2 on 2 tag match for this season. The Finale will be stream Live on September 4th, No audience. Team Tarrasque has been making some ground in the last few matches. They have picked up some momentum and they are closing the gap. Will they have what it takes to even the score going into the finale? Losing Team captain if fucked hard in front of the audience. Losers trib fuck in a biggest loser battle. Everyone gets fucked one way or another.

Savannah Fox in 'Rookie Cup champion Takes on Season 12 Tag Team Captain for a rematch'

Savannah Fox - Rookie Cup champion Takes on Season 12 Tag Team Captain for a rematch

Savanna Fox has been waiting for this day for a long time. Her first match on Ultimate Surrender was against Penny Barber. She lost to Penny the first time around but she has gone on to get a 5 match winning streak. Now that she understand the rules better, she is confident that she will be able to redeem herself against Penny. Penny is confident she will win just based on her size advantage. This match is everything erotic wrestling fans dream of. it's all out action with back and forth control for both girls. Several moments of "double control" where the girls must use their sex skills to out last the other girl. This match is so close it comes down to the final 10 seconds of the match. The girl who can score points better by face sitting and getting fingers into the pussy comes out the victor in the very last moment of the Match. This is Unbelievable!!

Penny Barber in 'take Anal from beautiful TS Jonelle Brooks'

Penny Barber - take Anal from beautiful TS Jonelle Brooks

Penny Barber is meeting with her soon to be ex husband's attorney to discuss some legal matters. Turns out Penny has been hiding some assets from her husband and the attorney want's to make sure Penny gets what she deserves. What Penny deserves is a nice hard cock down her throat, in her pussy and up her ass and that's exactly what Jonelle gives her. Penny takes every inch of the TS goddess's cock in every hole. She uses ever part of her body to satisfy Jonelle; mouth, hands, pussy, ass, feet. Jonelle finishes off on Penny's perfect toes.

Darling in 'Tag Team Erotic Wrestling Match with Gang Bang and Fisting Prize.'

Darling - Tag Team Erotic Wrestling Match with Gang Bang and Fisting Prize.

Penny Barber and Darling head their teams again for season 12. They attempt to coach their teams to victory, not because they love to win, mostly because they don't wanna lose and get gang banged again. Today the winners make the losers squirt all over each other and mop the mats with their faces. One poor loser is DP'ed and brutally fucked in front of her team

Sadie Santana in 'Francesca Le gives Pussy and Ass Fisting to Bad Girls who cant pay debt'

Sadie Santana - Francesca Le gives Pussy and Ass Fisting to Bad Girls who cant pay debt

Francesca Le has the best hand at the poker table and when the girls can't pay their debt she uses her hand to put them over her knee and spank their round bottoms. Sadie Santana and Penny Barber pay their debt anally. They are spread open, Penny is fisted in the ass and her pussy. Both girls are fucked with a giant strap on by the talented Francesca Le

Penny Barber in 'Milf Penny Barber does an erotic wrestling match with Lisa Tiffian'

Penny Barber - Milf Penny Barber does an erotic wrestling match with Lisa Tiffian

Because we had a rookie cup tournament, some of the matches had to be shot out of order to accommodate our update schedule. This is one of Lisa's First matches ever and she's going up against our finest vets, the Big tittied, mouth Milf we all love to hate, Penny Barber. These girls clash hard on the mats. There is a lot of power in both their legs, and much damage to be done with their huge tits flying around everywhere. The Winner takes the loser's ass and pussy as a prize. The tits are tied up and the loser is made to acknowledge they are a failure to all their fans.

Lea Lexis in 'Sexy Lingerie Football Team mates get some Anal Training from Coach'

Lea Lexis - Sexy Lingerie Football Team mates get some Anal Training from Coach

Lea Lexis is the head coach of a sexy "full contact" football league. When she walks in on two of her team members fooling around in the locker room, she decides to play hardball. With her fists in asses and pussies, Lea Lexis shows her team how to properly stretch. DP, Fistings, Everyone gets fucked!

Miss Jane Starr in 'Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic'

Miss Jane Starr - Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic

Miss Jane Star is a Type A rich bitch. She has taken her car to a mechanic and has waited over a month for her car to get out of the shop. When she comes in to check on her car she catches the mechanic literally jerking off on the job. While she is annoyed, Miss Jane Star is slightly turned on by the sass and mouthiness of the dirty mechanic. Jane Star fucks her mechanic and give her a nice dirty anal Cream Pie lube job of her own.

Savannah Fox in 'Penny Barber wants to squash a rookie. This rookie wont go down easy'

Savannah Fox - Penny Barber wants to squash a rookie. This rookie wont go down easy

This is Savanna Fox's first US match. She has some wrestling experience but she's also got a devastatingly huge booty that can pin girls down. Penny Barber has some ass of her own. These girls fight to impose their will on each other. Outstanding performance from a First time US wrestler. Loser gets an explosive load of cum splattered on her freshly fucked holes.

Darling in 'Team Tarrasque is Dominated on the Mats by Team Grappler'

Darling - Team Tarrasque is Dominated on the Mats by Team Grappler

One Team Takes a Huge Led and be Win. Losing Captain is Fucked Fisted and humiliated.

Penny Barber in 'Full-Time Dominance and Submission: Slave Contracts and Financial Domination'

Penny Barber - Full-Time Dominance and Submission: Slave Contracts and Financial Domination

Ready to kick your D/s up a notch, or even try it full-time? Here's what you need to know about consensual contracts, binding your partner into service to you, including guiding their spending habits. Penny Barber and Ella Nova demonstrate Slave Contracts as tools of negotiation and service. They also discuss and demonstrate how to use Financial Domination for deepening engagement with your submissive on a full-time level as well as money-oriented games and role playing.

Penny Barber in 'Anal Surrender! Sex Wrestling with Ass Smoother and Ass Fingering'

Penny Barber - Anal Surrender! Sex Wrestling with Ass Smoother and Ass Fingering

Welcome to March Madness on Everythingbutt.com Holly and Penny are two glorious wrestlers with glorious asses. Their ass are so Glorious that we are making them the Prize for this ANAL SURRENDER wrestling match. These girls must gain control and score points by finger each other's assholes, putting their assholes into each other faces or doing anything involving their big powerful tushies. The winner of this match up gets to do WHAT EVER SHE WANTS to the loser.Round 1 tactics allowed: Ass Sitting/Smoothering, Forceful ass worship, Anal, Fingering, AnilingusRound 2 tactics allowed: Same as round 1 however when a Wrestler gains control, she will be handed a toy and will be allowed to fuck her opponenets ass until control is lost. Prize round Brutal Ass fucking, Strap on and fisting!

Darling in 'Team Grappler Meets Team Tarrasque in the first Tag installment for season 12'

Darling - Team Grappler Meets Team Tarrasque in the first Tag installment for season 12

First Tag Match of the Season, Grapplers take on the Tarrasques in a nail bitting close match up. Losing Captain gets Cum Splattered on her freshly fi

Penny Barber in 'Horny Maid distracts Stock Traders, gets them to invest in her holes!!'

Penny Barber - Horny Maid distracts Stock Traders, gets them to invest in her holes!!

Power hungry cock-sucking, double penetration, and double-vag!

Penny Barber in 'Rookie Destroyed and utterly humiliated on the mats'

Penny Barber - Rookie Destroyed and utterly humiliated on the mats

cocky fit girls gets utterly humiliated on US mat. Submitted over and over, brought to the brink of tears

Lea Lexis in 'Pre-Season Tag Match up with all our Brats'

Lea Lexis - Pre-Season Tag Match up with all our Brats

Winners and Losers battle out who can cum first. Can the Losers redeem themselves in a sex fight?

Bella Rossi in 'Tag Team Fianle Team Queen has a devastating disadvantage going into the match'

Bella Rossi - Tag Team Fianle Team Queen has a devastating disadvantage going into the match

Each girl wrestles one round of extreme, intense tag team action, giving it everything she's got to help get her team the win

Mistress Kara in 'Our Top Ranked Wrestlers takes on our Biggest mouth'

Mistress Kara - Our Top Ranked Wrestlers takes on our Biggest mouth

The only way to shut Penny up is to stick a fist in her pussy while you sit on her face.

Daisy Ducati in 'Team Queen takes on Team Wrangler. Star wrestlers steal the show'

Daisy Ducati - Team Queen takes on Team Wrangler. Star wrestlers steal the show

Elite Wrestler gets Fucked and disgraced on the mats along with her Loser team mates

Holly Heart in 'Penny Barber and Holly Heart in Summer Vengeance. One gets bullied Hard'

Holly Heart - Penny Barber and Holly Heart in Summer Vengeance. One gets bullied Hard

Quitter get brutally fucked and fisted in prize round and has the audacity to get sassy with winner. Winner shows her who's boss after all.

Penny Barber in 'Singletailing 101 (East Coast Swing)'

Penny Barber - Singletailing 101 (East Coast Swing)

Learn the art of using a singletail in sensual ways, using control to safely and precisely deliver a wide range of sensations, from ooh to orgasmic.

Bella Rossi in 'Team Queen vs. Team Wrangler 2nd match up of the season'

Bella Rossi - Team Queen vs. Team Wrangler 2nd match up of the season

the strategy is the same for both teams; keep the rookie on the mat with the vet so she can get molested and sexually destroyed.

Ariel X in 'Anal Sluts: Penny Barber and Ariel X'

Ariel X - Anal Sluts: Penny Barber and Ariel X

Big Bottom Anal Sluts with Ariel X and Penny Barber.

DragonLily in 'MILFs Mom's I'd Like to Fight: Mini-tournament Who's the baddest mom'

DragonLily - MILFs Mom's I'd Like to Fight: Mini-tournament Who's the baddest mom

Each girl gets one round to prove herself against her opponent. If she wins she moves on to face the next opponent.

Penny Barber in 'Bratty MILF gets tortured and made to cum!!'

Penny Barber - Bratty MILF gets tortured and made to cum!!

Penny gets her bratty attitude checked by The Pope

Gaia in 'The Masochist Meets the Porn Star'

Gaia - The Masochist Meets the Porn Star

Porn Star Gaia Fucked in the Ass and begs to come while masochistic slut Penny Barber is beaten for her shortcomings

Penny Barber in 'Busty MILF's hot little mouth gets her in trouble'

Penny Barber - Busty MILF's hot little mouth gets her in trouble

Penny is known for two items: Her gigantic tits and her big mouth.The secret is that Penny does like to submit, but one has to cane her beyond words.

Penny Barber in 'get shut up by Cheyenne Jewels Bubble butt'

Penny Barber - get shut up by Cheyenne Jewels Bubble butt

Several Orgasms on the Mat. One Wrestlers show true sexual supremacy and physical dominance.

Bella Rossi in 'Masquerade Orgy with Nine Slaves,100 Horny Guests, Part Three'

Bella Rossi - Masquerade Orgy with Nine Slaves,100 Horny Guests, Part Three

Our slave girls finish off the rest of the horny guests and torture the bartender with orgasms.

Penny Barber in 'Two Strong Welter Weight Babes Battle for the chance to fuck the champ'

Penny Barber - Two Strong Welter Weight Babes Battle for the chance to fuck the champ

Too Proud to Lose. Jayogen is a reluctant Loser but she gives Penny Barber what she wants because Penny earns it

Bella Rossi in 'Masquerade Orgy with Nine Slaves,100 Horny Guests, Part Two'

Bella Rossi - Masquerade Orgy with Nine Slaves,100 Horny Guests, Part Two

When the Upper Floor throws an orgy, there is so much sex and bdsm going on than we have to break it into three parts

Darling in 'and Bella Rossi takeon Penny Barber and Rookie, Juliette March'

Darling - and Bella Rossi takeon Penny Barber and Rookie, Juliette March

With talent of this caliber, orgasms on the mat are guaranteed. true sexual dominance in every single round.

Penny Barber in 'Behind the Scenes Bloopers with Penny Barber and Holly Heart'

Penny Barber - Behind the Scenes Bloopers with Penny Barber and Holly Heart

Two buxom babes really let their personalities shine in this very candid and hysterical behind the scenes footage.

Bella Rossi in 'Masquerade Orgy with Nine Slaves,100 Horny Guests, Part One'

Bella Rossi - Masquerade Orgy with Nine Slaves,100 Horny Guests, Part One

Nine Trained Slaves are fucked, disciplined and tested in the annual Upper Floor Masquerade Orgy

Penny Barber in 'Big Tittied Babes Penny Barber and Holly Heart Wrestle and Fuck'

Penny Barber - Big Tittied Babes Penny Barber and Holly Heart Wrestle and Fuck

he Winner Tortures the Loser big titties in every way. Her Tits are stretched and squeezed in brutal fashion.

Penny Barber in 'Hot MILF, Tight Bondage, Mind Blowing Orgasms!!'

Penny Barber - Hot MILF, Tight Bondage, Mind Blowing Orgasms!!

Penny is tormented in tight bondage!

Penny Barber in 'Komic Kon Slut Gets Dicked Down in Elevator - Big Tits! Double Vag!'

Penny Barber - Komic Kon Slut Gets Dicked Down in Elevator - Big Tits! Double Vag!

Busty brunette with big round ass is cornered in an elevator where all her gangbang fantasies come true!

Penny Barber in 'Summer Vegeance Match up. Syd Vs Penny Barber'

Penny Barber - Summer Vegeance Match up. Syd Vs Penny Barber

Will all the trash talking get into Syd's head and make her fight with emotions rather than skill? Or will Syd make Penny her Bitch once and for all?

Penny Barber in 'Rounds 1-4 Tag Team Finale. Wrestling rounds and a 12 girl Fuck Fest'

Penny Barber - Rounds 1-4 Tag Team Finale. Wrestling rounds and a 12 girl Fuck Fest

month after month these teams fought on our mats for sexual supremacy. This Match determines once and for all what bitches are the toughest

Nerine Mechanique in 'Bailey's Redemption'

Nerine Mechanique - Bailey's Redemption

When Bailey Blue fails the House, she is sent to Training of O to learn to fuck better, and now she returns to the Upper Floor be redeemed.

Lorelei Lee in 'One Good Submissive and One Bratty Slut, Electrofucked LIVE!!'

Lorelei Lee - One Good Submissive and One Bratty Slut, Electrofucked LIVE!!

D-Cup submissives get trained with the cattle-prod, fucked with electric cocks and double-penetrated with electric ass plugs and samurais in this elec

Penny Barber in 'Jayogen makes US Debut'

Penny Barber - Jayogen makes US Debut

Dragon Lily is back on the mats wrestling for her team and she's in top shape. This is THE most exciting round of the match.

Penny Barber in 'Round 2 Tag Finale. Darling and Bella vs. Daisy Ducati and Penny'

Penny Barber - Round 2 Tag Finale. Darling and Bella vs. Daisy Ducati and Penny

Darling and Bella are relentless on their victims today. They use their tags wisely and #teamdragon has no answers for what they throw at them

Penny Barber in 'Tag Team finale Round 1 Bella Wilde and Berretta vs Sophia Fiore and Serena'

Penny Barber - Tag Team finale Round 1 Bella Wilde and Berretta vs Sophia Fiore and Serena

Bad Ass Sophia Fiore refuses to lose! She takes down Berretta AND Bella Wilde at the same time. But the 2 little ones give her a run for her money

Bella Rossi in 'SV S10 9th meets 5th. Two Voluptuous Welterweight Clash on the mats'

Bella Rossi - SV S10 9th meets 5th. Two Voluptuous Welterweight Clash on the mats

Bella wants to win Penny just to win Penny and Penny wants to win so she can meet up with Syd ( her arch nemesis this season)

Cheyenne Jewel in 'Full Match July Tag TEam Match-up Everyone gets a hand in fucking Syd'

Cheyenne Jewel - Full Match July Tag TEam Match-up Everyone gets a hand in fucking Syd

Team Dragon takes turns sexually brutalizing Nightmare's body. Fisted and fucked with a huge dong in her pussy and ass then left in a pile of losers.

Cheyenne Jewel in 'Dragon Maintains Lead for this Match. Big time Catch up done today'

Cheyenne Jewel - Dragon Maintains Lead for this Match. Big time Catch up done today

Penny and Cheyenne dominate this Tag match and play catch up after a horrible season! Team Nightmare is Devasted

Cheyenne Jewel in 'Round 2 July Tag match, Team Dragon vs. Team Nightmare'

Cheyenne Jewel - Round 2 July Tag match, Team Dragon vs. Team Nightmare

Dragon gangs up on the little Bella and racks up huge points. If they keep this up they could still stand a chance in the finals

Pink in 'Anal Slave Barks to Come while House Slave Earns Her Leathers'

Pink - Anal Slave Barks to Come while House Slave Earns Her Leathers

Watch Claire Robbins bark when she takes cock in a gorgeous ass

Cheyenne Jewel in 'Round 1 July Tag match. The Bellas of Nightmare vs. Cheyenne and Penny'

Cheyenne Jewel - Round 1 July Tag match. The Bellas of Nightmare vs. Cheyenne and Penny

Team Dragon sees the opportunity to catch up in season points by trapping Nightmare's weakest player on the mats and finger blasting her.

Syren de Mer in 'MILF Ass Slut Syren de Mer is Under the House Slave's Thumb'

Syren de Mer - MILF Ass Slut Syren de Mer is Under the House Slave's Thumb

When gorgeous MILF Syren de Mer is recruited to entertain Mr Grey's cock, she gets rough instruction from House Slave Penny Barber

Penny Barber in 'Summer Vengeance wrestlers ranked 10th and 9th meet on the mats'

Penny Barber - Summer Vengeance wrestlers ranked 10th and 9th meet on the mats

Winner humiliates the losers. Spits in Face, Squirts on her, Shaves pussy hair and glues it to her face with Honey. Loser left Genuinely humiliated!

Penny Barber in 'Anal Slave Meets the Household, and a Gorgeous Guest is Ass Fucked'

Penny Barber - Anal Slave Meets the Household, and a Gorgeous Guest is Ass Fucked

Blonde and Brunette with glasses take hard cock in the ass all night long to amuse the crowd.

Penny Barber in 'Smart Ass Anal Slave Girl Gets an Attitude Adjustment'

Penny Barber - Smart Ass Anal Slave Girl Gets an Attitude Adjustment

When Smart Ass Slave Girl Penny Barber arrives, she is fucked in the ass till she learns that Discipline, Duty and Dick rule the Upper Floor

Cheyenne Jewel in 'Round 4 April Tag match. Nightmare is Nobody's fool'

Cheyenne Jewel - Round 4 April Tag match. Nightmare is Nobody's fool

Audrey is fisted in front of the audience while her team mates are brutally fucked next to her. A fucking of Epic Proportions.

Cheyenne Jewel in 'Round 3. Nightmare vs. Dragon installment 3'

Cheyenne Jewel - Round 3. Nightmare vs. Dragon installment 3

Dragon uses all their tags early in the match which leaves Cheyenne out for almost half the round. Frustration sets in for team dragon.

Penny Barber in 'Welter Weight Semi Finals Penny Barber vs. Mistress Kara'

Penny Barber - Welter Weight Semi Finals Penny Barber vs. Mistress Kara

Kara gives Penny an opportunity to make up for being such an Ultimate loser by challenging Penny to a submission wrestling match.

Cheyenne Jewel in 'Round 2 Tag Match Nightmares elite wear down Dragon's best'

Cheyenne Jewel - Round 2 Tag Match Nightmares elite wear down Dragon's best

Team Nightmare bully Dragon's weakest player and rack up big points by fingering the pussy

Yasmine Loven in 'Super Voluptuous Welter Weights battle it out in the Quarter finals.'

Yasmine Loven - Super Voluptuous Welter Weights battle it out in the Quarter finals.

This match is so action packed, so energy driven that it was destined to end early because things got too intense.

Cheyenne Jewel in 'Nightmare not pleased with loss comes back with vengeance'

Cheyenne Jewel - Nightmare not pleased with loss comes back with vengeance

Cheyenne Jewel shocks the world with her legit skills, holding her own against two of U/S's legendary wrestlers

Penny Barber in '6 girl Orgy! Losers sex fight each other to determine Biggest Loser'

Penny Barber - 6 girl Orgy! Losers sex fight each other to determine Biggest Loser

It's Prize round time. Team Nightmare solidifies a good lead for the season. Team Dragon must pay the price with Anal sex and pussy pounding.

Penny Barber in 'Match 1 round 3 Nightmare vs Dragon NO TAGS FOR YOU DRAGON!!!'

Penny Barber - Match 1 round 3 Nightmare vs Dragon NO TAGS FOR YOU DRAGON!!!

Nightmare Squashes Team Dragon and traps their wrestlers on the other side of the mat so the Dragons can't tag out.

Penny Barber in 'Match 1, Round 2 Nightmare vs Dragon'

Penny Barber - Match 1, Round 2 Nightmare vs Dragon

Round 2 of the first match up of the season for Team Nightmare vs. Team Dragon. Nightmare Lays the lessons on dragon hard

Penny Barber in 'Season 10's First Tag Team Match: Team Dragon vs. Team Nightmare RND 1'

Penny Barber - Season 10's First Tag Team Match: Team Dragon vs. Team Nightmare RND 1

Syd Blakovich decides to put fate into her own hands and she's wrestling for her team for the first ever tag match up.

Tina Horn in 'Penny The Tarrasque Barber vs Tina professor Booty Horne'

Tina Horn - Penny The Tarrasque Barber vs Tina professor Booty Horne

Penny Barber completely dominates Tina Horne in an embarrassing competitive female wrestling match. Winner Fucks the Losers

Katie Summers in 'BIG TITS on the mat!! Pinned, Helpless, Fingered, and Strap-on Fucked!'

Katie Summers - BIG TITS on the mat!! Pinned, Helpless, Fingered, and Strap-on Fucked!

Big tits face off on the mat! Watch now to see who spends the day pinned and helpless, struggling to get the fingers out of her cunt!

Penny Pax in 'Tag Team Rd 3 - Tits vs Ass'

Penny Pax - Tag Team Rd 3 - Tits vs Ass

Team Tits - Penny Barber and Penny Pax face off Against Team Ass - Sarah Shevon and Odile

Penny Pax in 'Sept. Tag Team Match-Up!! Fierce Fight, Face Sitting, Finger Fucking'

Penny Pax - Sept. Tag Team Match-Up!! Fierce Fight, Face Sitting, Finger Fucking

Sarah Shevon and Odile face off against Penny Pax and Penny Play on the wrestling mat for the 2nd rd of this months Tag Team Match-Ip!

Aiden Starr in 'Competing Hookers'

Aiden Starr - Competing Hookers

Two locked up prostitutes give the lesbian officer kinky favors to get out of jail including drinking lactating breasts!

Penny Pax in 'Breast Fest! Hot 4-way action and it's Penny Pax's first time on US'

Penny Pax - Breast Fest! Hot 4-way action and it's Penny Pax's first time on US

It's Penny Pax's first time on the mat. It takes ovaries of steal to jump into a tag team with these crazy bitches. Expect a breast-fest!

Penny Barber in 'Summer Vengeance Tournament: One Match Closer to Determining the Champ'

Penny Barber - Summer Vengeance Tournament: One Match Closer to Determining the Champ

Summer Vengeance is narrowing down to it's close. Only the best wrestlers are left! Brutal submission holds and anal strap-on sex for the loser!

Penny Barber in 'Summer Vengeance Tournament: 15 vs 8 - Rookie Learns the Hard Way'

Penny Barber - Summer Vengeance Tournament: 15 vs 8 - Rookie Learns the Hard Way

When a wrestler ranked #15 faces off against #8 she quickly realizes that she's not as tough as she thought.

Bryn Blayne in 'May Tag Team Match-up: Round 4 Clash of The Titans!!!'

Bryn Blayne - May Tag Team Match-up: Round 4 Clash of The Titans!!!

Round four of May's Tag Team match!

Bryn Blayne in 'May Tag Team Match-up: Round 3 Clash of The Titans!!!'

Bryn Blayne - May Tag Team Match-up: Round 3 Clash of The Titans!!!

Bryn Blayne and Ariel X go head to head against Penny Barber and Bella Rossi.

Bryn Blayne in 'May Tag Team Match-up: Round 2 Clash of The Titans!!!'

Bryn Blayne - May Tag Team Match-up: Round 2 Clash of The Titans!!!

4 experienced wrestlers team up to destroy their opponents on the mat!! Face sitting, pussy fingering, and extreme g/g sexual wrestling domination!

Bryn Blayne in 'RD 14 of May's Live Tag Team Match: Totally non-scripted lesbian wrestling!'

Bryn Blayne - RD 14 of May's Live Tag Team Match: Totally non-scripted lesbian wrestling!

Big Tits vs Small tits: The epic battle is on, 4 girls non-scripted live Tag Team Action. Brutal action, the only REAL sex wresting in the world!

Penny Barber in 'Penny Barber'

Penny Barber - Penny Barber

Penny gets tiled up, blindfolded, and sprayed down with water

Penny Barber in 'Veteran vs Season 9 Rookie: Who will end up getting their pussy railed on the mat'

Penny Barber - Veteran vs Season 9 Rookie: Who will end up getting their pussy railed on the mat

Penny Play is determined to work her way up the ranking system. Lyla is determined to win one match! Who will end up chocking on the winners cock?

Audrey Rose in 'Veteran returns to show the new rookies hows it's done. Will she get her ass kicked Or take the win'

Audrey Rose - Veteran returns to show the new rookies hows it's done. Will she get her ass kicked Or take the win

Veteran returns to show the new rookies hows it's done. Will she get her ass kicked? Are the new class of rookies push overs.someone's getting fucked!

Shy Love in 'A Little Bit O. Hotel Ass!'

Shy Love - A Little Bit O. Hotel Ass!

Scott?s car broke down and he?s crashing at this hotel for the night. He is so bored, he calls hotel room service and tells them he needs some entertainment. Moments later, there's a knock on the door and Scott opens it, he sees Shy, a big butt escort at the door. He flips out as she pushes him on the bed? She gives him an ass show that makes his mouth drop. Then she dominates him and fucks him with her big ass and fulfills his wildest dreams!

Shy Love in 'Dr Shy Love or- How I Learned to Stop Cumming too Fast and Love the Spray'

Shy Love - Dr Shy Love or- How I Learned to Stop Cumming too Fast and Love the Spray

Scott Nails visits Doctor Love hoping to find an answer to his premature ejaculation problem. She introduces him to a very effective spray that numbs his cock. In order to find out if the solution works properly on him they must obviously fuck. Can you think of any other way of testing it out? No? Me neither.

Shy Love in 'Do You Want Dessert'

Shy Love - Do You Want Dessert

Shy Love heads off to a local restaurant where she hopes to find a waiter with a big piece of meat. Luckily for her Johnny is serving her tonight and desert is on the house.

Penny Barber in 'Good Girl'

Penny Barber - Good Girl

Innocent girl gets bound, spanked and fucked!

Penny Barber in 'Samantha Sin The Python (0-0) vs Penny Play The Tarrasque (0-0)'

Penny Barber - Samantha Sin The Python (0-0) vs Penny Play The Tarrasque (0-0)

Feisty Blond takes on Bodacious Brunette in nude wrestling.

Shy Love in 'Total Knockers'

Shy Love - Total Knockers

Shy Love is stressed the fuck out! She hasn't had sex in a long long time, she just went through a bad break up and she's been training for her next fight. Let's put her in the ring with Mikey Butders and see what happens. Keep your chin up Mikey cause she sucks like a butterfly and fucks like a whore!

Shy Love in 'One pie for Shy'

Shy Love - One pie for Shy

Today on our Big Tits Cream Pie adventure I got Shy Love. I bet everyone knows who she is. I asked my guys to meet her cause I was running late. She told them that she wants to fuck some young guy and by the time I got there I already had someone in mind for that, and of course that would be Porcupine. When we were sitting there at some cafeteria talking, some dude came up to us and once we told him what we were shooting for he got so excited I could barely get rid of him. Anyway back to my place, Shy and Porcupine were ready to fuck. She took care of this young man. He fucked her really hard and we all got to see this nice hot dripping cum out of her pussy. Check out this episode.

Shy Love in 'Sleeping on the Job'

Shy Love - Sleeping on the Job

Shy Love caught Keiran sleeping on the job again. This time she decided to fire him, but he insisted and decided to tell her why it happens: he's a ladies man that has a stable of women to satisfy every night, which leaves him very little time to sleep. Not convinced in the slightest, she decides to have him prove it to her by fucking her to redeem his pos

Shy Love in 'A BIG sprain'

Shy Love - A BIG sprain

Shy love is always getting in trouble, this time she injured Alec Knight. But she took him home and took care of him if you know what i mean. His sprained ankle wasn't hurting anymore when .Shy had Alec's huge dick in her mouth. She loves herself a big fucking dick.

Shy Love in 'Reunion Swapping'

Shy Love - Reunion Swapping

Shy Love invited her best friend Shyla Styles and her husband over. They hadn?t seen each other in a long time and had a lot to catch up. But when Shy caught Shyla?s husband looking at her ass and Shyla caught Shy?s husband looking at her breasts, the naughty housewives agreed to have a swap and enjoy the other?s better half. Shy enjoyed getting fucked in the ass while watching her husband fucking Shyla.

Shy Love in 'Teachings from the book of Kamasutra'

Shy Love - Teachings from the book of Kamasutra

This young man Seth is having a great deal of trouble trying to understand and follow the instructions in the Sex Pro book of Kamasutra. He nearly popped his blow up doll trying to reenact the sex positions in the book, so before he made a casualty of a real girl he called on Sex Pro, Miss. Love for aid. She brought out the sex god in Seth and it made for a very hot scene!

Shy Love in 'Climbing the corporate ladder'

Shy Love - Climbing the corporate ladder

It is Shy Love's first day at work and she was really surprised to find out that her manager is someone she had a one night stand with. At first she was embarrassed but then she realized this was a good opportunity to start moving up the corporate ladder so she showed him her real "skills" and made sure he would want to keep her around...

Shy Love in 'Love teachings'

Shy Love - Love teachings

Dr. Love, who is incredibly sexy might i add, today is doing a physical consultation shall we say. The man in to see her today is having issues performing anal sex with his partner and seeks the council of Dr. Love, approriate no? Being an expert on the issue she gives him a really in depth and passionate lesson on anal sex. See Dr. Love at her best in this scene, you might learn a thing or two!

Shy Love in 'Waste Time'

Shy Love - Waste Time

Jack came in to see his office doctor for his flu shot, only to find out that the doctor had left for the afternoon. Shy, the doctor's secretary, was able to get the doctor to come back, but now Jack has to wait an hour. Luckily Shy and Jack found a very convenient way to waste some time...

Harmony in 'Princess Donna Dolore, Harmony and Penny Barber'

Harmony - Princess Donna Dolore, Harmony and Penny Barber

Penny Play is the perfect little submissive slut. She likes to struggle, she likes to whine, and she likes to take whatever her dom can dish out. Harmony and Princess Donna gang up on Penny and give her some good back arching, pussy shocking, strap-on fucking fun!

Jezabelle Bond in 'shy love and Jezabelle Bond'

Jezabelle Bond - shy love and Jezabelle Bond

Jezabelle Bond is tall, sexy, has an amazing ass, loves bondage and submission. What more could you ask for? Shy Love dominates her in various positions and makes sure she and her sub have strong orgasms. Smoking fetish included.

shy love in 'and Deja Daire'

shy love - and Deja Daire

Deja Daire is extremely cute and innocent looking. She receives her punishment with obedience and being dominated is a definite turn on for her. Shy does a great job with breaking this new girl in.

shy love in 'Evan Stone and shy love'

shy love - Evan Stone and shy love

Shy Love returns for more domination, bondage and blowjobs. This time she goes to the next level and gets tied up immobile and fucked hard by the one and only Evan Stone.UPGRADED VIDEO QAULITYIPod 320x240 @ 762KbpsREAL and WMV 640x480 @ 700Kbps

shy love in 'and Wild Bill'

shy love - and Wild Bill

What would you do if left alone to clean Mistress Shy Love?s dungeon? Wild bill decided he could sniff and lick Her panties and rub Her high heel boots on his balls. All hell breaks loose when he gets caught by the sexy Mistress who then fucks him, flogs his cock and pounds his ass.

Christina Carter in 'shy love and Christina Carter'

Christina Carter - shy love and Christina Carter

Christina Carter makes her debut at whippedass with Shy Love as dominatrix. This busty girl can take some real pain and bondage especially when it?s mixed with sexual play. Her submission is breathtaking!

shy love in 'and Lacey Lust'

shy love - and Lacey Lust

A girls first time experience being submissive to another girl is a beautiful thing. Shy Love breaks in her new slave Lacey who is willing to be punished and humiliated. Featuring Ass licking, multiple orgasms, OTK, bootlicking, strap-on and more.

Isis Love in 'Isis Love, Sarah Blake, shy love and Nina'

Isis Love - Isis Love, Sarah Blake, shy love and Nina

Sarah?s the new cute and innocent girl in jail who gets roughed up and made into a little fuck toy by two badass dominatrices, Isis and Shy Love. Featuring double spanking, foot fucking, face sitting, ass licking, multiple orgasms, flogging and strap-on sex.

shy love in 'and Talon'

shy love - and Talon

Shy Love usually dominates men and sexy women but this time she switches to a submissive role and fullfils her secret fantasy. A thorough flogging and weighted nipple clamps in bondage was enough foreplay to make her want to be fucked real bad. With tight rope around her elbows she is made to deep throat which was exciting and new for her. Then, Talon fucks her good with plenty of spanking, chocking and anal sex.

shy love in 'mini and shy love'

shy love - mini and shy love

When you marry Shy love the wedding vows go something like - ?for better or for worse and when you stumble home drunk I crop your tied up balls, then flog your bare chest before you suck MY cock and I fuck YOUR ass?. Seems reasonable enough - if only in Shy?s dreams and his nightmares. Enjoy this fantasy trip down marriage lane.

shy love in 'and Dick Richards'

shy love - and Dick Richards

Help wanted - must be flexible, able to take direction and willing to work your ass off for the boss. Sometimes you have to read between the lines of the help wanted ads. Too bad dick wasn?t so quick to catch on. Mistress Shy Love gives him the job interview of a lifetime sparing very little of his ego or his flesh. Once the luscious Shy is done fucking the bound applicant she shows no mercy as he crawls around for her pleasure. If the office chair could talk, - oh, the screaming it would do. Enjoy!

shy love in 'shy love, Isis Love and Ed Stone'

shy love - shy love, Isis Love and Ed Stone

Shy and Isis use ed for the fucktoy that he is while tied down to their kinky dungeon bed. Oh, to be held captive by such beauties?but it has its price. These women want a hard cock, they expect it?and the fact that ed?s balls are tied is no excuse for not keeping them happy at all times! Satisfying one Dominatris is a tall order but 2 is even more difficult! Looks as if ed will be receiving some training in being a little bitch!MORE UPDATES?MenInPain now updates 6 times every month!

Penny Barber in 'and Isis Love'

Penny Barber - and Isis Love

First timer Penney has that cute and innocent girl next door look who really just wants to be a slut. She is slapped around by Isis which gets her pussy wet and is teased with the magic wand, giving her shameful orgasm after orgasm. Punished for cumming is a pleasure for Isis as well as worshiping her feet, pussy and ass hole. Isis takes her new fuck slave in the ass with a strap-on while bound and clamped. Penney?s new experience left her hoping for more to come in the future and I think you will too.

shy love in 'and Jasmine Byrne'

shy love - and Jasmine Byrne

Jasmine makes her debut at whippedass with the strict Mistress Shy Love, two beautiful and sexy Latinas. This update is chock-full of sexual domination including ass licking, spanking, whipping, footworship and strap-on ass fucking.

shy love in 'and Frank Stone'

shy love - and Frank Stone

Shy Love makes naughty office boy frank pay with his body for hitting on the girls in the office. Sexual harassment is taken to the next level as Shy flogs, fucks and shreds frank?s ass like confidential documents. Does he learn his lesson? Watch and find out?

shy love in 'shy love'

shy love - shy love

Shy Love is a Hustler star and covergirl of Club magazine?she is also one of the top Dominatrix?s used over at Whippedass. We?re not sure why such a dominant, established star of the adult industry would let us tie her up and dominate her for the first and only time anywhere but we were happy to take the challenge! This ?Mistress? needs to learn what its like to lose control and now we are the teachers. Enjoy!

shy love in 'Staci Thorn and shy love'

shy love - Staci Thorn and shy love

Staci Thorn is a sexy young blonde with a hot natural body and a slutty attitude. Shy Love is a real knockout brunette who truely enjoys overpowering submissive women. Together they create a lustful scene of lesbian power play.