Winnie Rider. yes, Yes, YES
 

Winnie Rider. yes, Yes, YES
Cast: Winnie Rider

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Winnie Rider likes pussy torture. I'm not sure why we're bothering to say anything else. She's hot, she's willing, she's literally begging for us to hurt her. Her body language says as much as her voice. She leans forward when she tells us about how much enjoyment she gets from suffering through intense pussy punishment. Whatever metal bondage devices and pain toys we bring out she will readily play with.
Winnie's wearing a pretty dress but not for long. OT cuts it away quickly, revealing her banging body. Her tits are large and firm. Her pussy is shaved clean, a perfect target for his whip to crack against. Her ass is a nice round target without a blemish on it. Not yet, at least. In a few minutes it is going to have a combination of bruises from a heavy caning and the light crisscrossing red marks of a harsh whipping.
She told us that her favorite thing was pussy torture, though, and we didn't forget. OT is going to flog, cane, whip and paddle her pussy without mercy. And that won't be all that happens. Bondage isn't just for arms and legs. Clamps and hooks contort her face until she looks exactly how OT wants her to.. It's uncomfortable and distracting but nothing is going to keep her from feeling the impacts that are going to come down on her exposed cunt.
By the time her slot is filled with the cold metal dildo she is so sore. It doesn't matter. OT pounds Winnie relentlessly with the toy until she has an explosive orgasm. That doesn't begin to describe the intensity. Winnie wasn't kidding when she said she loved pussy torture. Getting abused like she did had her dripping wet and ready to blow before the steel cock was even inside of her. She's crying but it doesn't stop her from cumming.

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2008 Carmen Blue
Cast: Carmen Blue

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2009 Evanni Solei
 

2009 Evanni Solei

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2009 Mckenzee Miles
 

2009 Mckenzee Miles

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Mackenzie Miles is a long time friend of Micah Moore. Micah told Mackenzie that the machines would be too much for her to handle. Well, Mackenzie proves Micah wrong and then some. She fucks fast and hard, cumming in every position we put her in.

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2010 Danika Lamb
 

2010 Danika Lamb

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Danika is eager to please and she wastes no time getting down to business with the machines. She's particular about how she likes to cum and only able to really get off when she's on her back. Danika has intense full body shaking orgasms that are pounded out of her with the SatisfyHer and the Snake. It's hot to watch her legs and ass uncontrollably jiggle during and well after she cums.

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2010 Cherry Torn Sarah Shevon
 

2010 Cherry Torn Sarah Shevon

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The Slaves flolick while the Master is away

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2010 Cherry Torn Sarah Shevon
 

2010 Cherry Torn Sarah Shevon

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The slaves clean the upper floor after a long weekend of debauchery. Slave Shevon is punished in the kitchen by Torn and Trainer Mogul for her bad attitude.

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Cherry Torn Sarah Shevon
 

Cherry Torn Sarah Shevon

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House slave Shevon is to be reviewed, but it's Torn that takes the correction.

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2010 Cherry Torn Sarah Shevon
 

2010 Cherry Torn Sarah Shevon

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The Household is called to order to determine the future of slave slut Sarah Shevon.

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2010 Cherry Torn Bella Rossi Sasha Knox-Maestro
 

2010 Cherry Torn Bella Rossi Sasha Knox-Maestro

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Sasha Knox is dragged from the basement on her fourth day of slave training on TrainingofO.com, and put in front of the Master of the Houe and the Household.

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2010 Veronica Avluv
 

2010 Veronica Avluv

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Veronica is a fucking machine. End of story. This hot MILF gets nailed by the hooked dong on the Dragon and cums and cums and cums. She does the standing splits over the bed frame - squirts. She does the spread eagle splits on the bed, squirts. Her pussy literally rains onto the bed sheets and she sweats and shouts "I've never cum like this!'. Pure machine fucking greatness that was captured live.

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2010 Cherry Torn and Jessie Cox - Stefanos Brunch
 

2010 Cherry Torn and Jessie Cox - Stefanos Brunch

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Join sadistic Masters and Mistresses for brunch and a kinky play party.

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2010 Bride to Lust Dia Zerva
 

2010 Bride to Lust Dia Zerva

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2011 AnnaBelle Lee, Jessie Cox and Kait Snow - Let it Snow, Let it Snow, Let it Snow
 

2011 AnnaBelle Lee, Jessie Cox and Kait Snow - Let it Snow, Let it Snow, Let it Snow

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First weekend of December, The Upper Floor celebrates the coming Holidays, keeping warm with a fine selection of slaves and some winter themed entertainment.

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2011 Jessie Cox and Kait Snow - Service Day
 

2011 Jessie Cox and Kait Snow - Service Day

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House slaves Jessie Cox and Kait Snow are played off against each other in a lesson about working together, composure, and grace.

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