Miss Jane Starr,Penny Barber in 'Kink TS' - Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Transsexual Pussy Hunters)

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.

Released : May 1st, 2015
Tags : Anal, TS, Straight, TS Fucks Female, Role play, Cock Worship, Blowjob, Vaginal Penetration



Pictures from Miss Jane Starr,Penny Barber in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic

Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 1)
Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 2)
Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 3)
Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 4)
Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 5)
Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 6)
Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 7)
Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 8)
Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 9)
Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 10)
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Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 12)
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Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 14)
Miss Jane Starr in 'Kink TS' Poor Little Rich Girl Doesn't know how to say No to a greased up Mechanic (Thumbnail 15)

More 'Kink TS' scenes from Miss Jane Starr,Penny Barber

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

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.

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.


Scenes from other sites featuring Miss Jane Starr,Penny Barber

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 '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.

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

Penny Barber in 'Tumble'

Penny Barber - Tumble

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

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 '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.

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.

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.

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.

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!!

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!!

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!

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!

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.