Jessica Kay - Kingdom of Ass and Pain
Release Year: 2018
Cast: Jessica Kay, Bethany Benz
Genres: BDSM, All Sex, Ass fucking, Ass to mouth, Asslicking, Cum swallow, Eating food from ass, Face fucking, Facial, Foot licking, kicking, Painal, Rimjobs, Rough anal, Rough oral, smacking
Video language: English
Jessica is a beautiful lifestyle slave who loves to serve and to suffer with her ass. She has a heart made of gold and an ass sculpted by the gods. That's why she's been back several times. She goes to places most girls you see just can't go--and she goes in filth and grace. This time, Dr. Mercies took her back to 3000BC, in a twisted but heartfelt retelling of Gilgamesh. This session has some extremely harsh sex, where Jessica gets anally hatefucked and smacked up; but it also has moments of sublime tenderness. The domination and sex are unscripted and real, though Dr. Mercies did have her read a pre-selected passage from from the story. This scene doesn't follow any of the rules, which means you've never seen anything like it before. It's hot as fuck, filthy, brutal, passionate, and will get you off while lifting your mind.
Format: mp4
Duration: 1:00:46
Video: 1920x1080, AVC (H.264), 7886kbps
Audio: 124kbps
File size: 3.5 GB
Jessica Kay Ho, Ho, Whore Part 2
Release Year: 2016
Studio: RealTimeBondage
Cast: Jessica Kay
Genres: BDSM, Torture, Humiliation
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.
Format: mp4
Duration: 39:02
Video: 1280x720, AVC (H.264), 7341kbps
Audio: 108kbps
File size: 2.1 GB
Assylum - Kingdom of Ass & Pain (Director's Cut)
Cast: Jessica Kay
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 we have one of the true pinnacles of Assylum with one of the most amazing and beautiful sadomasochists we've ever had here.
Format: mp4
Duration: 1:35:43
Video: 1920x1080, AVC (H.264), 6743kbps
Audio: 107kbps
File size: 4.7 GB
Kingdom of Ass & Pain Director's Cut
Release Year: 2024
Studio: Assylum
Cast: Jessica Kay
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 we have one of the true pinnacles of Assylum with one of the most amazing and beautiful sadomasochists we've ever had here.
Format: mp4
Duration: 1:35:43
Video: 1280x720, AVC (H.264), 2756kbps
Audio: 123kbps
File size: 2.0 GB
Jessica Kay Ho, Ho, Whore Part 3
Release Year: 2016
Studio: RealTimeBondage
Cast: Jessica Kay
Genres: BDSM, Torture, Humiliation
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.
Format: mp4
Duration: 37:33
Video: 1280x720, AVC (H.264), 7339kbps
Audio: 108kbps
File size: 2.0 GB
Kingdom of Ass & Pain
Cast: Jessica Kay
Genres: BDSM, Bondage, Hardcore, Anal, Anal Play, Dildo, Blowjob, Ass Licking, Rimming, Suspension, Cum In Mout
Video language: English
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 we have one of the true pinnacles of Assylum with one of the most amazing and beautiful sadomasochists we've ever had here.
Format: mp4
Duration: 1:35:43
Video: 1280x720, AVC (H.264), 2756kbps
Audio: 123kbps
File size: 2.0 GB
Bdsm New Kingdom Of Ass & Pain Director's Cut
Release Year: 2024
Studio: Assylum
Cast: Jessica Kay
Genres: Bondage, Hardcore, Anal, Anal Play, Dildo, Ass Licking, Rimming, Suspension, Cum In Mouth
Video language: English
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 we have one of the true pinnacles of Assylum with one of the most amazing and beautiful sadomasochists we've ever had here.
Format: mp4
Duration: 1:35:43
Video: 1280x720, AVC (H.264), 2756kbps
Audio: 123kbps
File size: 2.0 GB
Jessica Creepshow
Release Year: 2022
Video language: English
A girl doesn't get this many piercings without being into a little bit of pain. A girl doesn't get them where Jessica Creepshow has them without being into a lot of pain. She's dominant in her every day life and Jessica gets so tired of taking charge of every situation. What she needs is a man who can wrestle control away from her, put her in her place, and take what he wants from her while she is helpless and in his power.
Format: mp4
Duration: 1:00:17
Video: 1280x720, AVC (H.264), 6762kbps
Audio: 106kbps
File size: 3.0 GB
Jessica Kay - Kingdom of Ass , Pain Directors Cut 720p
We are almost the same height, but he is just slightly taller an imposing figure to anyone in his presence, Im sure.
Format: mp4
Duration: 1:35:43
Video: 1280x720, AVC (H.264), 2756kbps
Audio: 123kbps
File size: 2.0 GB
Assylum - 40,000 Years of Anal Tears
Release Year: 2018
Studio: Assylum
Cast: Jessica Kay
Genres: Ass fucking, Asshole pain, Asslicking, Face fucking, Facial, Foot licking, Painal, Rimjobs, Rough anal , Rough oral, Spitting, Bondage, Breast pain, Breast slapping, Face slapping, gagging, Mind fucking, Paddling, Pain, Pussy pain, Screaming, Suspension, W
Video language: English
Beautiful, submissive sweetheart Jessica Kay is back for another sick and twisted epic. And of course, she´s brought her plump, hot ass back with her. This time, Dr. Mercies is in good spirits, because life´s been treating him well. But he wonders what it would be like to be an anal BDSM pervert in other times and places. So he takes Jessica on a crazy painal domination journey across 40,000 years. This session is surreal but also real. It includes painful anal fucking in a straightjacket, cave woman beating, witch dunking, and severe ass punishment in the scold´s bridle.
Format: mp4
Duration: 1:22:56
Video: 1280x720, AVC (H.264), 1780kbps
Audio: 122kbps
File size: 1.1 GB
Jessica Kay - Maid for Punishment
Release Year: 2018
Studio: Assylum
Cast: Jessica Kay
Genres: Ass fucking, Ass to mouth, Asslicking, Cum in eye, Face fucking, Facial, Gaping, Painal, Pissing, Rimjobs, Rough anal , Rough oral, Breast pain, Crying, Endurance challenge, face pain
Video language: English
Hot little anal punishment glutton, Jessica, is back for day 3 of her Extended Shoot. Because she likes to clean, Dr. Mercies had her clean his closet, but he called her out every several minutes to use her submissive little mouth and asshole. This is no typical porno or factory BDSM movie, folks. This is an honest, spontaneous session that lasted close to two hours. It contains repeated bouts of rough anal sex, very punishing ass to mouth, extended deep rimming, face fucking, slapping, caning, flogging, tongue beatings, and much more. In the end, Dr. Mercies spread his cum into Jessica´s eyes and sent her back into the closet to continue cleaning with her eyeballs on fire. The beauty of this session is that Jessica liked it. She´s sick and awesome like that. [Extended Shoot, Day 3]
Format: mp4
Duration: 1:07:37
Video: 1280x720, AVC (H.264), 1514kbps
Audio: 117kbps
File size: 812.5 MB
A little pain for surrender
Release Year: 2023
Cast: Jessica Kay
Genres: All Sex, Ass fucking, Ass to mouth, Asshole pain, Asslicking, Cum swallow, Painal, Rimjobs, smacking, Spanking machine, Bondage, Caning, Crying, Endurance challenge, Paddling, Pain, Spanking, Big ass, Slim girl with round bubble butt
Video language: English
What better way to give thanks than with a painful anal fucking and a long, hard ass beating? So, for Thanksgiving dinner, Dr. Mercies bent Jessica over the table and turned on his brutal, new spanking machine from Germany. Then he calmly enjoyed his meal and ignored her while she suffered. Once her butt was all marked up, he gave it a good ass-to-mouth fucking. Her poor hole was already sore inside from her previous session, so she cried quite a bit when it got fucked again. But Jessica is an anal masochist who's always down for a challenge under the right circumstances, and she submitted beautifully. Dr. Mercies fed her his cum, and she swallowed it all down like a good girl. It was a lovely evening.
Format: mp4
Duration: 35:36
Video: 1920x1080, AVC (H.264), 5450kbps
Audio: 120kbps
File size: 1.4 GB
Pain-Slut girl Becomes Slave Girl
Release Year: 2014
Genres: Bdsm, Bondage, Humilation
Gorgeous schoolgirl Jessica is such an extreme pain slut that she breezed through the severe punishment of reform school having a grand time see "Reform school for teens: Upside Down Pain Slut Jessica"..
Format: Windows Media
Duration: 53:43
Video: 480x360, Windows Media Video 9, 1220kbps
Audio: 62kbps
File size: 490.0 MB
Pretty Jessica Kay is completely broken & dominated
Release Year: 2016
Cast: Jessica Kay
Genres: BDSM, Torture, Humiliation, Pain, Blowjob, Toys, Spanking
Video language: English
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 of course when we put her nipples in suction cups and a rope around her neck she is almost a blubbering mess. But if you want the real evidence of how much she has been through today, watch her reaction to the Sybian. The multiple, intense orgasms start to put a smile on her face, but she has been so horny for so long that she doesn't remember to hold herself back a bit. As soon as she cums once she is filled with regret. This machine doesn't stop like her gentle lovers do. It keeps on buzzing between her legs, tearing more ecstasy from her body until it turns to agony. Her eyes have rolled back into her head and she barely knows where she is by the time the vibrations finally stop.
Format: mp4
Duration: 37:33
Video: 1280x720, AVC (H.264), 7339kbps
Audio: 108kbps
File size: 2.0 GB
Jessica Ryan, Hazel Moore - World Tour From Home (2023)
Release Year: 2023
Cast: Jessica Ryan, Hazel Moore
Genres: Lesbian
Video language: English
Jessica Ryan is walking down the stairs when she is stopped by her , Hazel Moore, coming out of the bathroom and closing the door quickly behind her. Jessica is surprised and curious as to what Hazel is up to. Hazel explains that since Jessica has gone to so much effort to save up for Hazel's college - so much, in fact, that Jessica has been unable to afford a vacation for herself - Hazel has decided to show her gratitude with a special surprise!
Hazel says that she has drawn a luxurious bath for Jessica, who is instantly appreciative and moved by Hazel's thoughtfulness. But Hazel is quick to say that the bath isn't the only surprise she has in store for Jessica. Since Jessica can't go on an actual vacation these days, Hazel has planned a 'trip around the world' - all from the bathtub!
As Jessica relaxes in the bath while wearing her favorite bikini, Hazel uses various treats, decor, and music to help Jessica feel as if she's vacationing in different parts of the world. Jessica is charmed by Hazel's adorable efforts to make her happy, and eventually invites Hazel to join her in the tub.
Format: mp4
Duration: 35:24
Video: 3840x2160, AVC (H.264), 14645kbps
Audio: 125kbps
File size: 3.7 GB
Jessica Ryan: Reunited in Rope
Cast: Jessica Ryan ,The Pope
Genres: shaved ,The Pope ,BDSM ,Suspension ,Pain ,brunet ,Straight ,Flogging ,Rope Bondage ,natural boobs
Video language: English
Years ago, Jessica Ryan worked with The Pope on Device Bondage. Today she is trapped in his ropes as he has his way with her. She begins with her hands above her head and her legs spread wide in a standing position. She questions her choice to come back after all of these years. She’s eased into the day with a flogging that slowly increases in momentum, warming her body up for what comes next. Her pale flesh turns a bright red as the leather strikes her again and again. The orgasms follow the pain, which is more tormenting to her than the actual torment. Next, Jessica gets hoisted into a hogtie suspension with her arms tied to bamboo, holding them in a crucified stop position. The Pope introduces her to some electrical play, something new for Jessica. It starts with the zapper, and quickly escalates to the cattle prod. Her reward for enduring such brutal torment, is the vibe and lots of finger banging until the orgasms reach the same level of suffering. The final scene has Jessica on her back in a ball tie, with her legs pulled up away from the rest of her body. Bastinado is on the menu and there’s plenty to go around. First with the crop, next the cattle prod, and then to finish her off ,she gets the cane. Her reaction to the cane is what makes him happy, so he continues to torment the rest of her body with the cane as well. Her orgasms are powerful. He makes her hold the vibe herself, as he canes her feet for ultimate orgasms.
Format: mp4
Duration: 1:01:29
Video: 1920x1080, AVC (H.264), 9725kbps
Audio: 156kbps
File size: 4.3 GB
Assylum - Maid for Punishment
Release Year: 2018
Studio: Assylum
Cast: Jessica Kay
Genres: Ass fucking, Ass to mouth, Asslicking, Cum in eye, Face fucking, Facial, Gaping, Painal, Pissing, Rimjobs, Rough anal , Rough oral, Breast pain, Crying, Endurance challenge, face pain
Video language: English
Hot little anal punishment glutton, Jessica, is back for day 3 of her Extended Shoot. Because she likes to clean, Dr. Mercies had her clean his closet, but he called her out every several minutes to use her submissive little mouth and asshole. This is no typical porno or factory BDSM movie, folks. This is an honest, spontaneous session that lasted close to two hours. It contains repeated bouts of rough anal sex, very punishing ass to mouth, extended deep rimming, face fucking, slapping, caning, flogging, tongue beatings, and much more. In the end, Dr. Mercies spread his cum into Jessica´s eyes and sent her back into the closet to continue cleaning with her eyeballs on fire. The beauty of this session is that Jessica liked it. She´s sick and awesome like that. [Extended Shoot, Day 3]
Format: mp4
Duration: 1:07:37
Video: 1280x720, AVC (H.264), 1514kbps
Audio: 117kbps
File size: 812.5 MB
Jessica Marie ( Racist's Teenage Makes A New Friend!)
Video language: English
Jessica Marie is 18 years old. She's from a small town in the south. Very small, very safe community. People don't even lock their doors. It's a great place to grow up. And the reason-at least according to Jessica's -is because there's not that many people of a certain...persuasion around. He uses another word to describe them though....
It's a word that Jessica has heard so much during her 18 years, especially in the past year. Her said that the older she gets the more aware she has to be about what certain people would do to a 5 foot tall, 85 pound pretty little white girl. Yeah Jessica's is not very openminded. But Jessica is. She watches lots of music videos and reality tv shows so she knows that all the bad stuff her says about certain people is just nonsense. Now Jessica doesn't tell her this. You can't convince certain people of anything.
But how does Jessica know all the stuff her says about these people is wrong? Because (don't tell her ) but Jessica's friends with one of the people her hates. He always talks to Jessica when she's walking to and from school....telling her hi...that she's so pretty...encouraging her to go with him and have some fun...saying that him and her can have a party at her house when her parent's aren't home....Jessica knows her 's head would explode if he knew this...And his whole body would explode if he knew that Jessica invited this person into her 's home. And this person...he's got some ideas about fun stuff to do with this racist's tiny barely legal teenage ....
Format: mp4
Duration: 28:51
Video: 640x360, AVC (H.264), 879kbps
Audio: 309kbps
File size: 252.4 MB
HardTied Jessica Creepshow Cry Jessica Cry
Release Year: 2016
Studio: HardTied
Cast: Jessica Creepshow
Genres: BDSM, Bondage, Hardcore, Domination, Torture, Humiliation, Toys
Hardtied is known for bringing the best in the business when it comes to rope bondage. Jessica Creepshow is known for being on of the hottest models in the world....
Format: mp4
Duration: 46:52
Video: 1280x720, AVC (H.264), 6832kbps
Audio: 104kbps
File size: 2.3 GB
Bdsm New Stomach Punching Until You Pee
Release Year: 2024
Studio: SensualPain
Cast: Abigail Dupree, Jessica Kay
Genres: Punching, Hitting, Peeing, Crying, Pissing, Stockings
Video language: English
Abigail Dupree Punches Naked Jessica Kay in the stomach repeatedly causing her to yell out in pain, cry and almost puke. Beating the abdomen repeatedly again and again till she is laying on the floor in pain and has to pee. There is just something incredibly erotic about girl-girl Stomach Punching. If you clicked on this video, I think you are or will be a fan of abdominal Stomach Punching. Getting punched in the gut is one of the most painful things that can happen, but it can be the most erotic for some. Receiving pain from someone in a relatively unprotected areas of the body is giving power to someone to hurt you.
Format: mp4
Duration: 14:06
Video: 1920x1080, AVC (H.264), 6838kbps
Audio: 156kbps
File size: 723.2 MB
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