New Boyfriend Roped into Anally Punishing Mommy’s Bad Girl

Kacie Castle is a sexy and mischievous little slut with sparkling brown eyes that spell trouble, and a petite frame that begs to be bound and fucked. It is these exact qualities that lead Rob Piper to follow Kacie from a couple dates to a road trip to her Step-Mother’s mansion. Kacie is all flirtation and batting eyelashes as she explains that her Step-Mother is definitely out of the country and that Rob and her have the run of the house, as well as all the kinky BDSM toys hidden under the pastel decor. Rob has been waiting to really dig into all the submissive potential and filthy sex he knows Kacie needs. A pair of handcuffs and tight metal nipple clamps provide the perfect catalyst and soon Rob has this perverted little whore gagging on his massive cock, moaning from heavy face slaps, and gushing squirt as he holds her down and makes her cum all over her Mommy’s bedroom floor. A harsh punishment for cumming without permission includes ripping off her clamps and a flogging her bouncy ass until she can’t take it anymore. She begs to be his little fuck puppet and Rob pounds her into the mattress in metal bondage. Unbeknownst to Rob, he is now a pawn in a perverse game of lesbian desire between Kacie and her Mother. Kacie has alerted her Mommy with a text that they are in her home, with the hopes that this transgression will rekindle their old taboo D/s dynamic that Kacie still dreams about. When Helena comes striding into her home she takes no pause at the sounds of fucking in her bedroom, but goes right out to the bedroom window to spy on her step-daughter and her strapping new boyfriend fucking. She gets her voyeuristic orgasm by rubbing her wet pussy with one hand, keeping her eyes trained on her daughter getting pounded out. After her orgasm Helena marches back into the house and feigns a fake discovery of the young couple. The game is on, and Rob is sent upstairs to clean up while Helena and Kacie go head to head. Kacie wants Helena to still be her strict BDSM Domme and taboo lesbian lover, and Helena has decided Kacie needs to grow up and learn to serve someone else. But not before she has taken one last strict over the knee spanking and licked her Mommy’s pussy like a good girl. Rob is invited to join them so Helena can really train Kacie to be the anal whore she was meant to be. Drooling and begging on her new boyfriend’s dick, Kacie couldn’t look happier as Helena circles behind her with a hard flogging and crop to the pussy. Spit swapping, deep-throat training, and lesbian cuckolding are just a few tactics Helena brings to her daughters final test. Holding trays, as well as her orgasms, while having a zipper ripped off her nubile skin is a lesson in pain and service before pleasure. Canes further underline the point, leading to an insane double penetration scene with Helena ramming her huge strap on in Kacie’s already stretched asshole that is full with Rob’s hard dick straining against the walls of her pussy. Choked and cumming like an anal slut, Helena decides Kacie has proven herself and asks Rob to accept her slut step-daughter as his sexual servant.
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Hot Under Her Spell: Julia Ann dominates hypnotherapist India Summer

Frustrated and uptight in her day to day life, Julia Ann makes an appointment with hypnotherapist India Summer to get to the bottom of her issues. India guides Julia to a meditative state and is surprised to find that Julia’s dominant side comes out to play! Julia takes India over her knee, lifts her skirt, and starts spanking her perfect ass. India is unsure what to make of these new developments but she soon gets hot under Julia’s spell! Julia places binder clips on India’s nipples and slips her fingers into India’s pink wet pussy. India gasps as Julia licks her clit while ruthlessly fingering her cunt, ripping orgasm after orgasm out of her. Next, India is tied in doggy with a metal anal hook in her tight little asshole. Julia flogs India’s back and ass, before toying with India’s sensitive feet. India loves the feeling of the flogger on her ass and soon gets to pleasure her client. She licks and sucks Julia’s pussy and ass as Julia cums all over her slutty therapist’s face. Finally, India is in metal bondage and Julia straps on a thick fat cock to plow Julia’s pussy. Julia whimpers behind her ball gag, as Julia fucks her cunt and threatens her with the zapper. Each thrust pushes Julia’s cock deeper and deeper into India. After India cums hard, Julia turns her sights to her therapist’s ass. India groans as her ass swallows Julia’s thick strap-on. She begs to cum as her ass gets plowed first in missionary and then in doggy. Julia grabs India’s ponytail, holding her slut in place while she gives her a deep hard fucking. India can’t stop cumming and Julia doesn’t want her to. She pulls her cock out and maneuvers them into scissoring, and they both cum hard all over each other.
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This video is dedicated to my good friend Koo. He is the best person I know! Samantha the Rocker is one of those real disciplinary films with so many facets. I was dating the bass player for Samantha’s band for awhile (and introducing the concept of disciplinary spankings in her life as a motivational tool) When Samantha had issues with drinking and drugging too much as to damage the bands reputation. Karen (the bass player) approached her road manager and suggested in acquiring my help (an ultimatum) to Samantha regarding the ability to keep her as the front person. To make a long story short, Samantha , Karen and Tony the road manager showed up this day, wherein Samantha agreed to this spanking to clear the air with the irate band. This is a real as it gets!
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These girls try to help each other’s relationships, only to find themselves in a den of tease and training. Can their friendship survive the trials and tribulations that they face in the Mistress’s den? Pain, beauty, pleasure, and the severity of the Mistress’s whims, this video strives to push the limits.
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Anal Dungeon: Lisey Sweet’s Big Ass Gets Worked by Mistress Kira Noir

Lisey Sweet has a stunning body. From her blonde hair down to her thick juicy ass and thighs. This girl is banging and her boyfriend knows it, but she has a little problem. Her man is going to dump her if she can’t get bigger toys in her tight ass. So she does what any good partner will do and finds a professional to train her butthole. Showing up in a creepy dark alley wearing the highest booty shorts she meets her new mistress. Kira Noir is dressed in tight latex and ready to anally train her new pet. First she gets handfuls of Lisey’s perfect ass and spanks it red. Next she puts Lisey in a head cage fully nude with her ass exposed and ready for torment. She takes a hard beating with the flogger all while wearing a jeweled butt plug. Finally her ass is ready for more. Next up is a giant black dildo. This thing is huge and gets Lisey screaming with orgasm. After gaping over and over, Lisey floods the room with a huge squirting orgasm! Welcome to Lake Lisey! Next the real training begins and Kira brings out the speculum. After cranking it wide open she gets a full view of everything inside Lisey’s perfect pink asshole. Now it’s time for Lisey to return the favor and learn how to appreciate a tight hole. Kira gets fully naked and rides Lisey’s strap on. She gets fucked deep and hard in her ass over and over again. Finally she takes orgasm after orgasm from her little anal slut pet. Who needs a loser boyfriend anyway!
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French teacher, Anastasia knows how to captivate the attention of her new student Christina Carter. The restrained and gagged au pair is made to learn quickly and fulfill all her teacher’s Desires.
Bound struggles, gagged with lemons, compelled orgasm, wicked games and dick on a stick are all part of the learning process! That will teach her to question her teacher’s authority!
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One Tough Slut: Helena Locke pushes Ana Foxxx to the edge!

There’s no mistaking that Ana Foxxx is one badass slut and in this update, her ass is on the line! Domina Helena emerges from the shadows clad in shiny latex, eager to see how much this little girl can take. Ana is gagged and on her knees, with her legs are tied open and her arms tied behind her. Helena flogs Ana’s front and back to warm her up and puts clover clamps on Ana’s nipples and labia. Ana giggles with anticipation as Helena brings out the cane. Her giggles turn to cries as Helena gives her a good firm caning on her thighs. Her legs tremble and she breaks out in a sweat. Helena moves to cane her perfect ass and Ana takes every stroke. She yells around the gag, spit trailing over her lips and down her chest. After Helena removes Ana’s clamps, Ana cums hard. Next, Ana is suspended from one leg as Helena threatens her with the zapper. Once Ana has her instructions, Helena brings her down and puts her to work. Eager to avoid the sting of the zapper, Ana buries her face in Helena’s cunt, using her tongue to pleasure her Domina. Ana’s face gets sloppy wet as Helena rides her face and cums hard. Then, Ana is put on her hands and knees in thumb cuffs. Helena gives her a long hard spanking on her ass, paying extra attention to her shy asshole. She pushes her strap-on cock into Ana’s pretty pussy and fucks it until Ana cums. After her orgasm, Ana works Helena’s cock into her ass. Every thrust opens her ass up more, making her moan like crazy. Helena fucks Ana hard, before flipping her over on her back and fucking her some more! Ana cums hard with Helena’s dick in her ass like the good slut she is.
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Casey Calvert Demands Anal Payment From Submissive Roommates

Whitney Wright is late on her rent again. Laying around the pool is her two roommates, fully nude and caressing each other. The stunning and dominant Casey Calvert is having her way with the cute and perky young Miranda Miller. What excuse does Whitney have this time for not having the money. Casey offers up an all anal alternative to this dilemma. Will Whitney give up her cute perky bubble butt to make rent? Inside the house Casey shows her two girls the huge collection of butt toys. After some deep lesbian rimming, the glass dildo comes out to start stretching open Whitney’s tight asshole. Miranda wants her turn too and gets her ass filled and gaping with toys. Next the two girls have a turn stretching and gaping Casey Calvert with a butt plug. Finally with the hitachi out all the girls have deep anal orgasms. Miranda really wants to prove her worth to the household and takes a speculum in her ass for the first time. This stretches her cute butt wide open and gapes for all the girls. Whitney bounces her big booty on a huge dildo and rides it right to orgasm. Finally Casey shows both girls who is the boss anal bitch and takes a fist up her ass followed by two huge metal balls. Rent is paid in full this month!
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Cheyenne Jewel vs Mistress Kara

Welcome to the Summer Vengeance series Tournament on Ultimate Surrender! Today is the moment you’ve been waiting all summer to see. We have had 13 of this season’s finest veterans and rookies in a single knockout seeded tournament. Today we have our #4 ranked wrestler, Cheyenne Jewel, put against our #1 ranked wrestler, Mistress Kara in the season finale. Cheyenne “The Wrangler” is an all-natural, muscular, big assed, brunette hard-body. Her wrestling skills are very good, but she has taken on Kara many times and has never been able to figure out how to stop Kara’s signature move. Kara “The Queen” was originally ranked #2 behind Ariel X, but Ariel has had to pull out of the tournament due to injury. Kara is the Queen for a reason. She easily dominates her opponents and then turns them into servants to please her after each victory. She has one move that every single wrestler seems to get stuck in. A move that enables her to keep control while burying fingers deep into her opponents’ pussies. She has landed this move on every girl in this tournament. Today, Cheyenne Jewel is able to stop Kara’s move. This is her most technical match EVER against Kara. The girls are so even in the arm wrestling that they end up dragging each other all over the mats trying to gain an advantage. The wrestling is the same way. Zero points are scored in the first half of the first round. The girls circle each other and push each other, trying to catch each other off guard. They are tentative and patient. Each girl knows that one mistake can land them in hot water with fingers buried in their pussies. The match ends with a very low score on the board. The winner gets her hand raised and then drags her opponent to the center of the mats for brutal domination. The winner slaps the losers face and hand gags her as well. To show her dominance, she puts her loser into a head scissor and denies her orgasms while she punches her belly. The loser will only be allowed to cum when the winner allows it. Finally the champion allows the loser to cum and then makes her come again and again and again making her have orgasm overload. The loser is weak from the orgasms which makes her prime for putting into brutal submission holds. The winner takes advantage of this and puts the loser into one submission hold after another. She puts her in a choke, a boston crab, a baby swing and a camel clutch. The loser taps out each time. The winner then takes her strap on cock and fucks the loser until she cums more and more. Finally the winner wants her prize. It is her time to cum. The winner rides the losers face until cum is dripping out of her beautiful winner pussy. This is a winner take all match. The winner lifts and carries the loser off the mats and tells her that every night from today on, she is going to fuck the loser just like she did until the fucking loser can finally beat her in wrestling. This punishment is on going until these two meet again on the mats and settle the score there.
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Anal MILF And Busty Teen Service The BDSM Swinger Orgy

Part Two of our Upper Floor summer soiree finds our busty, all-natural teen Amilia Onyx trying to give a good disciplined fuck. But she isn’t used to working for her orgasms. She falls off the cock, begging forgiveness as she can’t remember a single one of the house rules! Her MILF sister in service saves the day. She helps her make it up to our guest of honor by giving his cock the ride of a lifetime, while cumming from a hard cropping on her swollen pink clit. The Governess kindly places Amilia on restorative ball duty, having her clean up the cock from balls to shaft. At the same time, London continues in an athletic reverse cowgirl display, her gorgeous tits bouncing. The Governess decides she is owed some gratitude from both of these little cock-whores and has them lap and lick at her pussy and ass until she cums. Stefanos tries to keep the place in order, making the submissives focus on protocol, all while flogging them. But the room is in sexual chaos. One of our beautiful guests is placed in a complex shibari tie and transformed into a little sex piggy with a curly tail butt plug. Humiliated and turned on, she is made to look at herself in the mirror with a pig nose and fuck herself with a dildo while her Master has her suck his cock. She is rewarded for her degradation with a orgasms in full suspension, twisting and oinking while the crowd cheers. Guests have a wild finale, exchanging sexual partners, finding corners for blow jobs, hardcore lesbian wrestling, and a very special birthday girl gets a very intense beating instead of the classic birthday spanking. She is given applause and aftercare, followed by her Master’s hard dick. The finale to the night places London in an inverted bondage pile driver with a hard dick in her ass and Aiden’s fist in her cunt. Screaming like a banshee, London still manages to wait for permission to cum, while licking Stefanos’ shoes as she’s getting double fisted. Amilia is placed back on cock duty, and gets her face covered with cum and sweat, as she bounces her 19 year old ass. London and Amilia are both cropped and made to fuck until they can’t fuck anymore. At the end of the night, when they both look like sweaty, fucked out little sluts, Stefanos and Aiden congratulate themselves. Finally, some proper servants for our sexually depraved House! Both whores are rewarded with a hot load of cum and collared for good service.
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California Neighbors Do Anal!

Everyone knows California neighbors do anal! Everyone except for Christie Stevens. Fresh from middle of the country, Christie is shocked to find her neighbor Chloe Cherry stripping in her backyard. Christie rushes over to let Chloe know that everyone walking by can see her, but Chloe isn’t bothered. She’s a California girl through and through, and she’s excited to show her hot new neighbor how they do it in California. She helps Christie out of her dress and leads her inside for an introduction to California anal! Inside, Christie wiggles out of her panties and spreads her legs, revealing her perfect pink pussy. Chloe can’t wait to get her mouth on a fresh pussy. As she licks Christie’s pussy, she slowly slides her fingers into Christie’s tight asshole. Christie moans as Chloe’s tongue and fingers work their magic. Chloe pushes a plug in Christie’s ass and then it’s Christie’s turn to return the favor. She tastes her first California pussy and teases her new neighbor’s ass with a plug. All this foreplay has Christie hooked. Seeing all Chloe’s toys, she asks if they can try other toys and Chloe is more than happy to share. She spreads Christie’s cheeks and watches as her neighbor’s ass swallows a fat glass plug. Once the plug is in, Chloe licks the opening of Christie’s tight hole as it clenches down around the plug. These two hot babes take turns cumming on a variety of plugs as they tease each other. Next, Christie sets her sights on bigger toys. She pushes a fat black dildo into Chloe’s ass and fucks her to orgasm. Chloe moans as her neighbor fucks her tight ass. She then puts another anal toy on the floor and bounces on it as Christie tells her what an anal whore she is for splitting her asshole open for her new neighbor. Then it’s Christie’s turn to get fucked. Chloe fucks Christie’s ass with a fat cock. Christie cums hard as Chloe fucks her relentlessly. Finally, Chloe gets Christie to fill her ass with as much of her hand as she can fit. Christie gets most of her fist in and works it in and out of Chloe’s tight ass as Chloe cums over and over again.
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Some folks are just not cut out to be criminals. It might be that they just haven’t thought things through, in this case, they are too easily distracted. When the pretty burglar finds the damsel in the house she’s prepared to rob, she quickly does her up in pretty scarves that go so well with bare foot bondage. Our damsel hops away in a futile attempt to escape, but finds herself tightly rope tied and ball gagged in the living room. With the next awesome tabletop, blindfold and gag hog-tie, it is easy to that the burglar is more interested in her helpless victim than the booty in the house. She better watch herself though, because her has learned a few rope tricks from all these predicaments, and if she can escape…well, let’s just say the tables might be turned in quite a delicious way.
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The husband is forced to watch as Kendra James and Bella Rose decide to have some fun with each other. Kendra verbally torments the poor husband while she plays with Bella’s nipples and pussy. Bella is more than happy to receive the attention she is finally getting.
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Yet another eye-roll-absurd case of client biting off more than he can chew. This gentleman sent me a trove of sex toys with the request that I test them ALL on him.
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