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Jessica Kay – Kingdom Of Ass & Pain Director’s Cut 

Six years ago, Jessica Kay delivered one of the most extreme and moving sessions in Assylum history. Today, we bring it back, with 50% more footage and an entire re-mastering of the scene. This session is level 11! The faint of heart should not proceed. The painal is harsh, the punishment is hard, the degradation is deep. But this session is also a re-imagining of the great Epic of Gilgamesh–a sincere spiritual journey of a pair of modern perverts. Here…

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RealTimeBondage – Ho, Ho, Whore Part 2 – Jessica Kay, Jack Hammer 

A girl with her head sticking out of a barrel probably thinks that she knows what kind of punishments and humiliations she is about to be subjected to. Jessica Kay only has her face available, after all, so she has to assume that there is only so much pain and degradation that we can inflict on her. It’s amazing how naive some people can be. Between the hooks, the mouse traps, and a bit more of Rain DeGrey’s special sauce,…

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RealTimeBondage – Ho, Ho, Whore Part 3 – Jessica Kay, Jack Hammer 

We unwrapped our toy, and we’ve been playing with her all day, but we are not every careful when it comes to pretty, young sluts. Jessica Kay should have been labeled fragile, because she is about to be completely broken by the end of this. Enough pain will bring anyone to tears, so it isn’t surprising that Jessica is crying while we flog her tits. Her nipples have been getting played with all day and they are super sensitive. And…

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SensualPain – Girl Girl and Dreamy Masturbation | Jessica Kay | Abigail Dupree 

Am I rather for you? Mmm Dad please side to orgasm with me, let me see your pulsing dick orgasm when I do. How many times do you orgasm to the idea me being fucked by another woman? Mmm, simply considering 2 hot women enjoying with each other makes my pussy slick as well as wet. Is it enjoyable to view me pleasure myself with my preferred vibe while thinking about your orgasm in my mouth? My pussy is so…

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SensualPain – Stomach Punching Until you Pee | Jessica Kay | Abigail Dupree 

Abigail Dupree Punches Naked Jessica Kay in the tummy continuously creating her to scream out suffering, cry as well as practically puke. Defeating the abdomen continuously time and again till she is laying on the flooring hurting and also has to pee. There is simply something unbelievably sexual about girl-girl Stomach Punching. If you clicked this video clip, I assume you are or will be a follower of stomach Stomach Punching. Obtaining typed the digestive tract is among the most…

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SensualPain – Oct 20, 2019: Whore Trained For The kerb crawler | Jessica Kay 

The dark passenger cruises the city streets at night and the early mornings before dawn. He is me, I am of him that will always be. I know him as a cruel and cunning dude that collects the lost and bates them with food. He is sly and shameless, nocturnal and ageless. He hunts for Jack or Jill, the runaways, the homeless not the pigswill. But I am different than this Master of perversion, that I watch with blurred vision….

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Sensual Pain – Feb 19, 2017 – Abigail Dupree | Jessica Kay | Master James 

  Slave jess was sent to the Sensual Pain Dungeon by her Master, to be put through a rigorous series of tests at the hand of Master James. Tests of strength, endurance, will, tolerance, honor, submission and pain. To begin, Master James has her kneeling on the slave seat and adorned with heavy, rugged stocks on her wrists and neck. Where perfection and a confident will to achieve are expected from an alpha slave like jess, she tends to forget…

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Real Time Bondage – Jan 2, 2016 – Jessica Kay 

  A girl with her head sticking out of a barrel probably thinks that she knows what kind of punishments and humiliations she is about to be subjected to. Jessica Kay only has her face available, after all, so she has to assume that there is only so much pain and degradation that we can inflict on her. It’s amazing how naive some people can be. Between the hooks, the mouse traps, and a bit more of Rain DeGrey’s special…

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Infernal Restraints – Title: Nov 6, 2015: The Assistant | Jessica Kay 

  Jessica Kay got into this gig thinking that if she hung around long enough then maybe O.T. would notice her and decide to use her in the same way he does all of the models that come onto the set. She doesn’t want to be on video, she has no interest in being a star, but Jessica definitely wants to be dominated and she has become obsessed with being the next girl he handles. Her plan is simple, if…

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Hardtied – Oct 28, 2015: Innocence Lost | Jessica Kay | Jack Hammer 

  A girl like Jessica Kay lets you know with her smile and her body language that she is young and innocent, but she doesn’t want to stay that way forever. She wants to keep the look, for sure, because she knows that it makes the men want her. What she wants to lose is the actual innocence. She doesn’t just want to be wanted, she wants to be had. She wants to be used. She wants to be beaten…

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Hardtied – Oct 28, 2015: Innocence Lost | Jessica Kay | Jack Hammer 

  A girl like Jessica Kay lets you know with her smile and her body language that she is young and innocent, but she doesn’t want to stay that way forever. She wants to keep the look, for sure, because she knows that it makes the men want her. What she wants to lose is the actual innocence. She doesn’t just want to be wanted, she wants to be had. She wants to be used. She wants to be beaten…


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