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Welcome SUPER MILF Shay Fox to Whipped Ass. Shay seeks the help of Gold Star Services looking to forget her failing marriage of 15 years by becoming a gold star lesbian -- a woman who has only had sex with women. With the unconventional help of Gia Dimarco, Shay is made into a hungry pussy licking, strap-on fucking, ass worshipping, lesbian punishment slut!

Melody Jordan is just the kind of innocent-looking, girl-next-door type that we love around here. We never know what to expect out of the new girls but half the fun of having them is breaking them in. Everything is new to them, from the restriction of the bondage to the intensity of the orgasms. All of it is combined with a rough throat fucking it is a sexual overload for our cute little ingenue.

$Two cute topless red-haired girls get cuffed to St.Andrew\'s cross by mature BDSM master$

$Our little Nympho MILF is learning a little about grace under pressure on her journey through the Training of O. She is also getting fucked in the ass allot. In this installment, Veronica Avluv is taken back to the dungeon where she must prove herself worthy to return to a plush, domestic setting.Avluv is first made to suffer the cowgirl trainer, a simple device designed to make or break a slave girls ability to \'Do The Work\'. Once past this trial, she may proceed to getting some real cock. First her face is brutally fucked in a blaze between masturbation, pussy control and deep throat skills.TTOO is famed for it\'s brutal cowgirl fucks, and Veronica applies herself to the task with a vengeance. Once her pussy is heated, she can accomplish anything, and she slams that huge gimp dick with her pretty little pussy for all she is worth.When we finally sink that cock into her waiting asshole, she cannot control the overwhelming orgasms and she is gone. Watching this slut get her ass pounded into oblivion in the name of servitude has a poetic justice to it. Is she good enough? You decide.$

Super Sexy Kristine Kahill has returned for another serving of rough bondage and hard cock just the way she likes it. Sexually Broken is the only place that gives her the perfect mix of pleasure and pain that makes her have the most intense orgasms of her life. If she can deep throat, cum on command and keep us satisfied than maybe we will even go a few more rounds with her. If she is lucky.

Multi orgasmic squirter, anal queen and genuine submissive Veronica Avluv is back for an action packed BDSM session! Dominated by Mr. Pete who is in top form, Veronica gets rough sex, corporal punishment, face fucking, strict bondage and hard fucking in her pussy and ass!

Summer Brielle returns for a very intimate BDSM scene with Mr. Pete.

What ten thought was going to be her average interview very quickly turned into a whole lot more

She is weak. She knows nothing about submission. But she is fucking hot, and she fucks real good. Unfortunately for her, that is not enough. This site needs standards, and the only way to instill them is to cut out the weak. But not before using them up and teaching them where they stand.

In a post apocalyptic future, Darling and Casey Calvert are captured by a savage hunter who sexually torments them with bondage and rough sex. This feature presentation fantasy movie includes hard bondage, anal sex, rough blowjobs, role-play and intense orgasms!

Highlights from the BEST Anal MILF Training Movies!Favorite MILFS Veronica Avluv, Simone Sonay and Holly Heart in the best anal MILF Training scenes that Kink.com has on offer!

$We love Darling not only for her amazing talent of flexibility but also how this hot cunt can just cum and cum and cum. Repeatedly her body is stretched to the max in outrageous positions. She cums like she is in pain, and all that does is turn us on. In the first position Darling is bound with her tits and ankles tied in a bow on a box. The weight of her torso presses her tits into the box uncomfortably. She is hoisted into the air and gets reminded that all she is good for is being under Claire\'s Dominance. In the second position, she is bound in an open legged hairpin. Clamps on her nipples, breast bondage, and an anal hook all add a feeling of completeness to this helpless cum whore. Third, Darling is installed in a very challenging hogtie suspension with her tits bound to her ankles. Last, the almighty sybian always finishes. Darling gets thoroughly fucked into another planet getting a sybian ride she will not soon forget.$

When I am feeling a bit frisky I like to punish two slaves at one. Nothing beats double tit torture.

$FREE PREVIEW : WMV | WMV HD |MP4 HD |iPodThis is a previously recorded event from the Training of O archives published here as a bonus!House owner, Peter Acworth, is very annoyed that the training of Upper Floor slaves is taking so long. Worried that the slaves will not be ready for a Cocktail Party tentatively planned for next month, Peter has asked Lead Trainer, James Mogul, to screen several local applicants and host a full-scale slave audition in the Armory\'s basement that he will personally oversee. Among the applicants is Satine Pheonix, who shamefully collapsed from sugar deprivation at The First Supper inaugural event. Those who make it through the audition will enter a grueling training program with hopes of eventually petitioning the House for a position among the Upper Floor slave ranks. Join Peter, James, handler Maestro and newly initiated Upper Floor slave Cherry Torn to help test these applicants and decide who is worthy of being trained.$

Mia Li is an exotic Asian beauty. She has marvelous, big, sensitive tits, practically begging to be tied off, pinched, or clamped. Her ass is so nice it would be a crime not to spank it, cane it, or whip it. She has long, black hair, perfect for pulling. So when she showed up telling O.T. that she loves tight, rough rope bondage. Her words and her body are literally asking for what comes next.

Penny Pax is an E.R. doctor who is haunted by the ghost of a man whose life she could not save. After visiting Penny at her office and at a local bar, he finally materializes in her bedroom one night and gets revenge through rough anal sex and bondage!

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$This is our Double Blind Study - an experiment to test the limits of two young and beautiful people. How long can they stand to be stressed physically, mentally and sexually before they can\'t take anymore and their minds or bodies break? We have our volunteers and a series of increasingly terrible torments already lined up. We won\'t quit until we have our answers.$

Dedicated Divine Bitches member and slave boy, Lucas Knight, applies to win a fantasy hour with Goddess Lorelei Lee. His selfless devotion earns him his wet dream and his worst nightmare. Lorelei owns him and his orgasm through intense humiliation, sploshing, strap on fucking, flogging, cropping and face sitting.

$You have seen Tiffany Tyler before, this long legged beauty is as sexy as sexy comes. She is flexible and multi-orgasmic. Now you get to see the first scene she ever did for us. This is the meet and greet with Tiffany, where we gauge her strengths, weaknesses, we do all the bondage on screen. This is the very type of scene that you, the members, can easily do at home. Watch and learn, this update is for you. We simply bind her elbows and wrists tightly together. In less than 30 seconds this tall, thin flexible girl is 100% helpless. We add a neck rope and play breath games. The danger makes her pussy dripping wet, she is scared but excited. We own her now sexually and she doesn\'t even know it. We add nipple clamps, flog her and then pull her arms up in a brutal strappado. The vibrator makes her cum over and over. She is helpless, we make her cum at will until she is exhausted. Now we pull the strappado tighter and make her suffer until we return. When we do return she will do anything we want...$

Gorgeous, horny MILF of the Year India Summer is put into a domestic setting and taken down a notch on her journey to learn her Principles of Servitude. Hard discipline, painful predicament bondage, hard anal and pussy fucking, face fucking all stand in the way to learning her lesson.

$Liv is still new to the BDSM world, but that doesn\'t mean this slut doesn\'t love to suffer. Her body is fucking amazing and we make sure to display it in grueling bondage. She may be new to the game, but Liv is definitely one that loves to suffer. Her orgasms get stronger as the pain increases throughout the day.$

Nadia Styles returns to Sex and Submission with Tommy Pistol in this kinky role play with rough sex and bondage.

Darling returns for a very intense lesbian BDSM experience with Lorelei Lee including lesbian bondage, fisting and anal fucking!

Rose Red stars in this feature presentation with James Deen. This 22 year old, all American girl loves bondage, anal sex and rough sex. James goes to work on her and pushes all the right buttons in this super hot and intense fantasy role play update.

In this erotic fantasy role play, Mellanie Monroe and Alura Jenson live out their sexual fantasies as they are dominated and fucked in the ass by Bill Bailey.

Savannah Fox returns for more spanking, punishment, fisting, deep anal and extreme squirting in this sexploitation women in prison lezdom flick!

$Darling is another big time bondage legend who never does boy/girl sex. Or at least she was until she met us. There is something about our special brand of bondage that is so intensely erotic that she just can\'t hold back. She takes the hardest fucking of her life, screaming and cumming the entire time. After a few squirting orgasms her eyes roll back into her head and she is out.$ $Governess Lia Lexis trains defiant pupil Skin Diamond. Zapper, electro strap-on, tens unit, face sitting and finger banging make up Lea\'s multi orgasmic electro sex toolbox of discipline.$

$Rain DeGrey once said that she doesn\'t think there is anything more painful than having her tits tormented. It\'s time to prove her wrong.$

$Cherry Torn\'s breasts are one of the seven wonders of the world. They keep getting bigger and she loves them being bound severely. I could elaborate on a long drawn out dialogue about what happens, or I could let the pictures and video speak for themselves. Enjoy this bitches\' ride from hell on the sybian, challenging suspensions, predicament bondage, and nice tight breast play!$

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$Watch Part 1!! The wait for part two of the racy step mother and daughter lesbian drama is over. In part 1 we find Ella and Darling captured and fucked by two sadistic lesbians. The story continues to unfold when the truth about Ella\'s mom comes out and the sadistic lesbian make Ella punish and fist fuck her mother! Ella breaks away for just enough time to call on one of her mother\'s friends, Simone Sonay who naively arrives at the situation and is quickly turned out by the evil cunts! Simone is spanked, humiliated and double strap-on fucked in from of her best friend and her best friend\'s daughter. The mother\'s are ass fucked deep and the daughter is made to lick the cocks clean of all the ass juice. Once the lesbians are through with them they kick them out made, to fend for themselves in the city naked and fucked!$

$Gorgeous, lascivious Angel Allwood is one of the hottest blonde MILFs we\'ve encountered, and I\'m certain she will win you over as a true Electroslut. Aiden starts by tying this big-breasted beauty to a metal staircase and working her over with the violet wand and electro hitachi. Lots of clit zapping and intense orgasms. Next Aiden makes this pretty lady crawl her bubble butt over to a bare mattress and gets her ass in the air for some ANAL electricity and DOUBLE PENETRATION with the samurai! Pussy licking, high voltage, and lots of tongue zapping earn Angel an A+!!!$

$This Special Halloween Feature update stars bondage superstar Darling in a cruel sex-slave auction. After being sold to the highest bidder, Darling is locked up in wooden stocks and sexually used for her new master\'s pleasure. Watch Darling get overwhelmed with intense pleasure and erotic torment as she endures strict bondage and merciless fucking in her tight ass!$

$The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this fantasy role play, Cherry\'s husband gets a promotion that requires him to move across country. Not wanting to leave, she agrees to live the rest of her life in sexual servitude. Shot on location this update includes rough sex, anal penetration, hard face fucking, painful nipple and tongue clamps and bondage sex!$

Cowgirl suspends Lorelei and teases her mercilessly until she begs to cum!! The elctricity is turned all the way up and she is punished for her orgasm!!

$Wenona and Darling are a pair of veterans so you know it takes some extreme measures to make them scream. It takes a glob of wasabi up Wenona\'s ass or tying off Darling\'s nipples so tight that they look like they may twist off. It takes hot wax, an intense fucking machine, a brutal caning and some good vibrations. And it takes the suggestions of our members, carried out by our twisted crew.$

$Welcome Alina Li for her first bondage shoot ever. Her body is put in compromising positions and her pussy is exposed for The Pope to do his bidding. Her nipples and pussy are clamped and weights added until she can\'t take any more and then orgasms are ripped from her willing cunt.Next she is spread wide on the floor and again her body and pussy fall under assault. She is blindfolded and helpless with fear of what comes next.Finally we have her ass in the air to torment her hungry cunt. She is manhandled and made to cum so many times that she truely doesn\'t know her own name.$