Ass Caning

All posts tagged Ass Caning

Matt Williams has has a long week, all he does is work work work. But now it is the weekend and it’s time for him to unwind with one of his all time favorite activities: tormenting a sexy woman until she unravels. He’s found himself a fit young thing by the name of Sierra Cirque and the two of them are about to have a heck of a time together. After each brutal session, she will be rewarded with some time with the hitachi, but if she doesn’t cum loud or well enough for him, the next session will be even worse.

Matt has Sierra on the floor in a tight little dress, heels, and a black ball gag, tied up with her arms behind her and her knees spread so that her pussy is visible. He slices off the shoulder straps from her dress so that her tits are exposed and beats them some with a flogger, just enough so that her nipples harden and he can tie some twine between them and her thighs. After that’s set up, he takes the flogger to her pussy. Drool drips from the ball gag onto what remains of her dress from the pain.

The next few sittings Sierra has more of a say in. He plays some games with her, a different game for each round. The first time he picks the body part and she picks the toy, whether she wants to be hit with a dragon tail, a flogger, or a cane. In another he has her choose a number between one and ten, and the difference between her number and his number is how many times she is struck with the cane. And at the end of all of it it’s time to check again if she has learned to cum when told.
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Suffering for the Sake of the Subs

London River, one of our more accomplished handlers, has just finished a shoot for one of our other sites when O.T. finds her. When asked how it went, she says it was good, but she thinks maybe she got in a little too deep, went a little too far. She thinks maybe she deserves some kind of punishment to fix what she has done wrong and teach her a lesson for next time. Lucky for her she has a great friend like O.T. to help her out in that department.

O.T. takes London and ties her up in rope so that she is hung from the ceiling by her waist, wrists, and ankles. She struggles to get her feet down to the box beneath her to try and take some of the pressure off of the bound bits of her. Meanwhile, O.T. makes it more difficult for her. He punches her stomach and slaps her face a few times making her move around more so it’s harder to keep her feet down. Then he starts tickling her, after all it seems only right to do to her exactly what she does to her models.

After that he takes her down and sets her down on her back, her feet pulled up right next to her head so that her pussy and ass are wide open and exposed. He takes a metal hook and pushes it inside her ass as he starts to vibrate her clit with a celebrator. He pumps the hook in and out of her ass hard and fast. It’s almost too much for even London to handle. Maybe she has learned her lesson, thinks O.T., but he needs to be absolutely sure, so it’s time to bring out the cane.
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Lying Slut Gets Shown What’s What

Bonnie Day is all about O.T., she has been trying to hook up with him for a long time. Now she has started to get a little too aggressive, when he rejects her this time, she threatens to tell London River, his main girl, that she’s already slept with him already. Tragically for her, he’s sitting with London when he gets the text with the threat, and the two of them know exactly what to do about her. When she arrives at O.T.’s place to meet him, she is instead met with London’s fist and a quick nap.

When she wakes up she is all wrapped up in belts in a burlap sack with her mouth bound in a tape and cloth gag. Now it is time for O.T. and London to have their fun and exact their revenge on the presumptuous girl. O.T. slices off Bonnie’s panties with a knife as London humiliates her by drawing a face on the sack where her face should be. The two of them take turns punching the sacked up girl.

O.T. then takes out a few of his tools and beats her body over and over again. He gets her all wrapped up in black gauze like a mummy, then slices a hole in it for him to be able to access her ass. He uses his cane to beat it until it is bright red. Then it’s the whip cracking all up and down her body lashing against her soft skin. And after that the flogger, slamming against her until she screams.
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Homeless Hoe Beaten Black and Blue

KoKo Kitty has been down and out, living on the streets for the past few months. Each day she sits out in the park, asking for loose change, wrapped in her blanket just trying to keep warm. That’s where O.T. finds her, curled up for warmth, sitting on a curb, holding a cup out for a donation. He can do her one better, though. He tells her if he goes with him and takes a few pictures he’ll pay her for her time, and she won’t even have to get naked. But when has that ever really been the case?

They arrive at the studio and O.T. give KoKo a place to shower and get dressed, promising he wont watch her while she’s in there. He didn’t promise that he wouldn’t pop in to give her a towel, though, or that he wouldn’t take the panties she left on the floor. That’s about as close as O.T. is going to get to keeping his word, though. When she’s done getting dressed O.T. traps her in some extreme metal bondage and starts to take off the clothing she has just put on.

Then he sets to work beating her up and down. He whips her perky tits and her pussy with a dragon tail and canes her ass until it turns purple. Then he spreads her legs, sticks a metal pussy hook inside of her, and starts pumping. After a moment he brings in the celebrator and starts vibrating her clit. In no time at all she is moaning and sqirting all over the place, her body betraying her and forcing her into orgasm. She got some reward, maybe she’ll get her money eventually.
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Dripping Wet and Hung Out to Dry

In the third and final installation of Nikki Darling’s second live feed, while she gets soaking wet we are getting ready to hang her out to dry. We strap her arms together and up to the ceiling and have her stand on two metal blocks with electricity coursing through them. Then O.T. and London River work together with whips to really make her suffer. They lash at her back and her ass, sending stinging pain through her body and making her start to cry almost immediately.

O.T. and Matt Williams strap her ankles up to the ceiling and release her wrists so that she is hanging upside down, legs spread. Then they strap a hitachi in place right over her clit and slide a metal pussy hook inside her. O.T. sets the hitachi to high and gets back to whipping. He focuses on her breasts this time, to shake things up. She’s shaking and swinging in pain and pleasure. O.T. puts his whip back down so he can take the pussy hook in hand and fuck Nikki with it, and she loves it. She screams as she cums hard from the pressure of the hook on her G-spot.

They pull Nikki down to the floor again so that they can have her bend over the cage they have Milcah Halili boxed up in. O.T. takes out a cane and starts beating her sweet round ass. With every stroke she lets out a little whimper and then begs for more with a “thank you sir may I have another?” And the answer to that is always yes. He keeps going on her until her gorgeous ass is covered in little raised purple lines and he is sure he has left a lasting impression.
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Starlet Gets Surprised at Interview

Devilynne is an up and coming starlet and she’s looking for her big break when she finds herself in O.T.’s office. She’s determined to get the job, but he doesn’t seem too sure about her. He says that he can tell a lot about a girl from the smell of her panties. It seems odd, but she waits until he looks away and removes them for him to sniff, and clearly he smells something promising, because she gets the job. Devilynne is about to learn first hand, though, that there is no easy way to the top, as she finds herself gagged and tied up in leather straps on the floor surrounded by people waiting to touch her.

O.T. sets her up, laying her down on her stomach and strapping her ankles to her neck in a hog tie. Then Matt Williams sticks a stocking over her head and gives her an electrical tape gag and blindfold, tying the stocking to her feet as well so that her head is held up. O.T. pulls up her skirt so he can tickle her and she starts screaming, so he decides he’d better give her something to scream about. He takes out a cane and starts beating her ass and her feet.

He sits her up with her legs spread by two wooden posts and sticks a bit gag in her mouth. She knows she’s stuck. She doesn’t struggle. She sits there waiting for whatever O.T. will deliver next. He brings a dragon tail over and lashes at her ass and pussy with it. In no time she is crying and drooling all over herself. Then it’s time for him to share a keepsake with her. He pulls out his phone and shows her a video from earlier in the night a dick being stuffed down her throat, and that gets more screams than even the beating. She can’t take seeing herself that way, but she has no choice. Just like she has no choice in whether or not O.T. is going to make her cum.
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Slut Gets Stage Soaking Wet With Squirting

If there is one thing we know for a fact about KoKo Kitty it is that she is a big time A-list squirter. It’s ridiculous. Every time you make this girl cum the entire room gets soaked, and KoKo cums on a dime. Luckily, Matt Williams likes it wet and wild, and he’s ready to see just how much he and KoKo together can make it rain. With any luck he’ll be splashing around in rain boots in the puddles she makes by the end of their time together.

When we arrive at KoKo she is sat down on a sybian vibrator, tied down to the floor by a rope around her waist, and dressed in a tiny pink dress that doesn’t even cover her bare pussy. Matt cuts the straps off of her skimpy dress, then he turns on the sybian and takes out a flogger. As she sits there, completely overwhelmed by the power of the vibration from the sybian, Matt flogs the rest of the dress off of her, gradually uncovering her tits and stomach, making each stroke more painful as less of her is covered by fabric. Once they are totally exposed, he ties her nipples down to the floor so she forced to bend even farther forward than her strappado is already pushing her.

Matt then ties her up so she is lying on her back, her ankles lashed to wooden poles on either side of her to keep her legs spread, and her neck tied down to the floor. He takes a little time to cane her feet and flog her pussy to get her worked up. Then it’s time for the waterworks. First he takes out the metal pussy hook, sticks it inside her and starts fucking her silly. In no time at all she is squirting all over the place, but it still isn’t enough, so he takes out the hitachi and vibrates her too. There is cum flying everywhere and Matt Williams is a happy camper, practically bathing in it.
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Tramp in Tears Keeps Teasing

Nikki Darling stunned our staff at first when she came back for a second live feed on Real Time Bondage. Being completely used for hours on end by a crew of merciless handlers who are being advised by some of the sickest minds on the internet, our loyal viewers, is no easy task. And now, in her second installment, you can really see just how much it takes out of a girl. When we return to her she is sitting on the floor looking exhausted. Our staff doesn’t know how much more the poor girl can take, but it is our job to find out.

O.T. puts Nikki on top of the cage of Milcah Halili, who only gets to watch and doesn’t get to play. He ties Nikki’s hands behind her back into a strappado, which he then ties to a rope around her neck, so that every time her arms get tired and she lowers them, she has to choke herself. Our girl is a little overzealous though, and leans into it, lowering her arms intentionally as O.T. vibrates her pussy and punches her stomach. In no time at all she is in tears and cumming hard and loud against the hitachi.

Then our handlers move Nikki so that she is sat in mid air, held up by her two legs which are spread and cuffed to wooden posts on either side of her. A collar around her neck is attached to a chain leash which pulls it up just a little too high so she is being perpetually lightly choked. Her arms are bent behind her over a wooden pole and tied in place. Now the handlers have free reign to interrogate her, vibrating or caning her harder when she talks back or gives an answer they don’t like.
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Perfect Pussy Turned Purple

O.T. has Milcah Halili wrapped around his finger, and chains wrapped all around their body. They start out in a cute little green dress and beige high heels, bound with shackles so their legs are spread and their arms locked tightly behind them. They have a bit gag in their mouth and a look of fear on their face, probably for good reason. O.T. spends a little time getting a feel for their body by poking and prodding it with a BBQ skewer before he really gets to work.

He turns Milcah upside down and shackles their ankles in place so that their ass is sticking straight up in the air, and their head is below their knees in a collar. They kneel there on the box, unable to move, as O.T. canes up and down their thighs and ass. They wince with each strike, as their skin begins to turn colors and there are purple and red lines up and down the backs of their legs and ass. He uses a variety of different width and material canes, finding out which kind gets the best reaction. Then he sticks a metal butt plug in their ass and starts moving it around inside of them as he uses a hitachi to vibrate their pussy.

Then he flips Milcah back onto their back so he has better access to their other hole. He slides a metal pussy hook inside her and starts pumping away at it, fucking her as once again he takes out the hitachi and places it right on her clit. Cum is pouring out of her pussy as it gets fucked, it’s almost too much for her to take. O.T. doesn’t want to overwhelm her with pleasure, so hes stands her up and chains her wrists to the ceiling so he can whip her tits and face.
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Pussy Pounded Until the Cunt Cries

Sasha Heart’s body is absolutely incredible. She has perky breasts, an ass that won’t quit, and an all over tight little figure that could make a grown man cry. That, however is not the plan. Matt Williams ball gags her and ties her legs so they are spread wide and her pussy exposed. Then he ties her nipple clamps down to the floor so that she can’t move without causing herself pain. Only then does he take out the cane and start beating her ass and up and down her legs. It looks like Sasha is going to be the one doing all the crying today.

Next, Matt moves Sasha so that she is roped to a chair, her tits held in place by a breast harness. The best part of the setup, though, is the hitachi vibrator set to high power and taped down to the chair between her legs so that she can’t move away from it pressing against her clit. All she is left to do is sit there cumming over and over again as Matt attaches clothespins, first to her nipples, and then down her stomach in a zipper. When he tears them away she goes to scream, but Matt covers her mouth with her hand so she can barely even breathe as she shakes and writhes in pain.

By the time he finally decides to move her, Sasha has had the hitachi vibrating her pussy for around fifteen minutes. One might expect that after being vibrated for that long, her pussy might have just gone numb, but actually it works the exact opposite way, making her clit more and more sensitive with every moment it’s on. That’s why it hurts so much when Matt bends her over backwards and starts flogging her pussy, and why she screams out with such pleasure when he finally stops flogging her and starts finger fucking the life out of her. By the time he’s done Sasha has completely lost count of how many times she’s cum. It’d be surprising if she even remembered her own name.
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