Jessica Kay - 40,000 Years of Anal Tears
Release Year: 2018
Cast: Jessica Kay
Genres: BDSM, Bondage, Face Fucking, Rough Oral, Whipping, Mind Fucking, Paddling, Pain, Gagging, Suspension, Rough Anal
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: 1920x1080, AVC (H.264), 5623kbps
Audio: 122kbps
File size: 3.4 GB
Jessica Kay Ho, Ho, Whore Part 1
Release Year: 2015
Studio: RealTimeBondage
Cast: Jessica Kay
Genres: BDSM, Torture, Humiliation
There was a horrible experience Rain had years ago, involving q-tips and a very spicy, green paste, and she has been waiting all of that time to pass along the love. It's going to stick with Jessica, too, judging by the tears, snot and drool running down her face.
Format: mp4
Duration: 41:11
Video: 1280x720, AVC (H.264), 7336kbps
Audio: 109kbps
File size: 2.2 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 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
Jessica Marie ( Racist's Teenage Daughter 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 dad-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 dad 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 dad 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 daddy says about certain people is just nonsense. Now Jessica doesn't tell her dad this. You can't convince certain people of anything.
But how does Jessica know all the stuff her dad says about these people is wrong? Because (don't tell her dad) but Jessica's friends with one of the people her daddy 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 dad's head would explode if he knew this...And his whole body would explode if he knew that Jessica invited this person into her father's home. And this person...he's got some ideas about fun stuff to do with this racist's tiny barely legal teenage daughter....
Format: mp4
Duration: 28:51
Video: 640x360, AVC (H.264), 879kbps
Audio: 309kbps
File size: 252.4 MB
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
Jessica Kay - Christmas Domination
Release Year: 2015
Cast: Jessica Kay
Genres: BDSM, Torture, Humiliation, Pain, Blowjob, Spanking
Video language: English
Now that the dinner is done and the presents unwrapped, it's time to unwind with one last piece of Christmas joy. This little present is named Jessica Kay, and she calls herself a natural submissive. She got into BDSM by reading a certain famous novel that will remain nameless, and we're happy to further her education in the erotic arts. We learn a few other secrets from her,
Rain DeGrey is disappointed in the effort she has put forth so far. She can barely fit a couple of fingers down her throat, so she is going to need some training before she managed to get a decent cock in there. If her face is no good for fucking, then she's going to have to use it for something else. Rain plans on making her suffer. There was a horrible experience Rain had years ago, involving q-tips and a very spicy, green paste, and she has been waiting all of that time to pass along the love. It's going to stick with Jessica, too, judging by the tears, snot and drool running down her face.
Format: mp4
Duration: 41:11
Video: 1280x720, AVC (H.264), 7336kbps
Audio: 109kbps
File size: 2.2 GB
No Escape - Jessica Kay
Release Year: 2015
Genres: BDSM, Anal Fingering, Ass Caning, Blindfold, Caning, Cloth Gag, Crying, Dildo, Fingering, Orgasm, Rope Bondage, Tears, Thigh Caning
Video language: English
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 until she is bruised and crying. And she'll have it.
Jack is going to cane her until the tears flow from her face and the juices flow from her pussy. She's a bondage slut and a pain slut, completely ready to submit, even while she sits there grinning with her braces and innocent smile. Young, eager, and oh, so sweet, Jessica is about to become a favorite play thing for one of the most intense dominants out there.
Format: mp4
Duration: 1:16:58
Video: 1280x720, AVC (H.264), 6798kbps
Audio: 105kbps
File size: 3.8 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
Jessica - Grosses Out Swallowing In Her First Gloryhole (2023)
Release Year: 2023
Cast: Jessica
Genres: Oral
Video language: English
Jessica is a young mother at only 26-years-old. She was telling me how she just wanted to get out and do something hot and sexy because she is stuck at home all the time with her kid, or she is working to support her kid. The idea of sucking anonymous dick at gloryhole had her really turned on! But wait, you will crack up once you start watching this video. She really gets grossed out by having to swallow all the cum and you can visibly see her gagging on having to swallow so much. Jessica is an all-natural amateur mom next door and I believe the fantasy in her head was hotter than the reality. For us watching it is way hot seeing a young mother gag on cum. I do believe Jessica liked it; however, she literally didn’t expect so much cock and so cum in her belly. Well, she certainly had the Jizz Locker experience and took 8 big loads of cum and swallowed. Slow-motion cumshot replays included!
Format: mp4
Duration: 35:17
Video: 1920x1080, AVC (H.264), 5102kbps
Audio: 153kbps
File size: 1.3 GB
Jessica Starling - Big Tit Blonde Loves Hardcore Anal (2023)
Release Year: 2023
Cast: Jessica Starling
Genres: Anal, Big Tits
Video language: English
Jessica Starling looks stunningly beautiful in a red crop top and tight denim shorts paired with black stiletto-heeled sandals. The gorgeous blonde bombshell playfully strips out of her clothes to show the full beauty of her big tits, huge ass, and plump pussy. Seeing Jessica's naked body is enough to make Michael Stefano want to have fun with her right away. Unable to restrain his lust, the veteran stud immediately gives Jessica the pussy licking she deserves. Aside from enjoying the taste of the blonde babe's pussy, Michael also takes pleasure in giving Jessica sensual foot worship. The naughty hottie returns the pleasure by giving Michael a passionate footjob. Moans of delight fill the room as Michael fucks Jessica's pussy while spooning her. The horny lad then slides his dick into Jessica's asshole while fucking her in missionary. Jessica gives Michael a blowjob and titjob before riding his cock in cowgirl and reverse cowgirl. She can feel Michael's dick stretching out her tight asshole as he keeps up with the intense anal pounding. Michael continues fucking Jessica's gaping asshole doggystyle before cumming in Jessica's mouth.
Format: mp4
Duration: 41:09
Video: 1920x1080, AVC (H.264), 6115kbps
Audio: 256kbps
File size: 1.9 GB
Jessica Kay - Kingdom of Ass & Pain (Director's Cut)
Release Year: 2024
Cast: Jessica Kay
Genres: BDSM, Bondage, Hardcore, Anal, Anal Play, Dildo, Blowjob, 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 Starling - Brazen Blonde Takes An Anal (2024)
Release Year: 2024
Cast: Jessica Starling
Genres: Anal
Video language: English
Pigtailed blonde Jessica Starling is relaxing outside when she notices the gardener, Vince carrying out his chores. She gives her friend a call and gets distracted as she watches Vince from a distance. She tries to get his attention by seductively eating a banana and then struts over to him to get what she wants! Jessica pulls out her big boobs and kneels down on the grass to suck his big cock. Making things nice and sloppy, Jessica gets face fucked and deepthroats until she gags, impressing her gardener immensely! They head inside and Vince fucks Jessica's pussy and ass in multiple positions. This brazen blonde gives him a tit job and even takes his cock from ass to mouth! Finishing up with a messy cumshot over her tongue, Jessica spits out his load and rubs it all over her big tits!
Format: mp4
Duration: 45:28
Video: 1920x1080, AVC (H.264), 7409kbps
Audio: 210kbps
File size: 2.5 GB
Jessica Ryan & Lily Lane - Lily Lane Handles Jessica Ryan’s Ass
Release Year: 2023
Cast: Jessica Ryan, Lily Lane
Genres: BDSM, Bondage, Lesbian, Anal, Anal Stretching, Strap-on, Dildo, LezDom, Ass Licking, Rimming, Stockings
Video language: English
Lily Lane and Jessica Ryan get it on for the first time in this super hot EB update. Princess Lily saunters into the dungeon in her sexy lingerie and high heels to find Jessica is all tied up and eager to please. She starts with the crop on Jessica’s butt, thighs and tender feet getting her all warmed up for a day of all the way girl on girl ass play with lots of big toys. Lily stretches Jessica’s tight hole with bigger and bigger butt plugs and then fucks her ass good with a strap-on dildo causing her to cum hard. Then Princess Lily lures her filthy little toy into her own sexy, curvy ass. Jessica licks Lily clean and then fucks her ass with a thick pink dildo and then an even bigger toy and finally stretches Lily’s ass wide open with an industrial speculum. What a fun play day!
Format: mp4
Duration: 58:18
Video: 1920x1080, AVC (H.264), 9743kbps
Audio: 156kbps
File size: 4.1 GB
Jessica Deep Sucking While Getting Fucked In The Ass
Release Year: 2017
Cast: Eden Sin , Jessica
Genres: BDSM, Bondage, Torture, Humiliation
Video language: English
Eden Sin is turned into a Jessica 3000! The experiment was largely sexual in nature. Restraints are necessary due to the intensity of the procedure. Once Eden is locked down she begins to question her decision to sign up for the Jessica 3000 experiment. To be fair she hadn't done any research on what she'd be getting into. The dick gag down her throat and the pear of anguish in her ass begins to give her an idea of what she is in for. The drool drips from her face and she's pulled by her asshole to the floor into a horrific squatting position. She nearly drowns in her own spit. Each phase of the experiment gets worse. She's made to bend over and suck on a cock deep in her throat while she's fucked from behind. Her thumbs are pulled high above her while she's gagged and whipped. The final phase of the experiment is where the real action happens. Large metal rods skewer her body through her ass and out her mouth. The drool and tears drain from her face. When the electric wires are attached our new Jessica 3000 begins to panic!
Format: mp4
Duration: 29:46
Video: 1280x720, AVC (H.264), 7323kbps
Audio: 106kbps
File size: 1.6 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 Starling - Jessica s Darling Gape
Cast: Jessica Starling
Genres: Anal, Blowjob, Gonzo, Hardcore, Oil
Jessica Starling is your new favorite gaping darling as she really opens up in this playful anal romp! This blonde bombshell is the anal slut your dreams are made of— beautiful face, slim waste & a very welcoming & wet, juicy gape! Watch as she lets you into her deepest parts with the thickest dick opening her up!
Format: mp4
Duration: 41:22
Video: 1920x1080, AVC (H.264), 11622kbps
Audio: 124kbps
File size: 3.5 GB
Jessica Ryan - To Make Up For The Lost Time (2023)
Release Year: 2023
Cast: Jessica Ryan
Genres: Anal
Video language: English
Redhead mylf Jessica overhears her stepson Spikey as he’s talking on the phone with his girlfriend about wanting to try anal, but it seems like she’s not up for it. When Jessica goes to talk to him he asks her about her reunion and she mentions that it made her realize that she’s not as adventurous as she used to be. She then reveals that she overheard his conversation and, tapping into her adventurous side, suggests that he could try anal with her!
Format: mp4
Duration: 33:58
Video: 1920x1080, AVC (H.264), 4690kbps
Audio: 125kbps
File size: 1.2 GB
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
Jessica Ryan, Savvy Suxx - Swapping To Teach a Lesson (2024)
Release Year: 2024
Cast: Jessica Ryan, Savvy Suxx
Genres: Orgy
Video language: English
Anthony comes home tattered and humiliated, and he admits to his stepmom, Jessica, that he is being bullied at school. Jessica demands Anthony reveal who his bully is. Soon after, Jessica calls Savvy, the stepmother of Anthony’s bully, Dylan. Jessica isn’t going just to sit around idly while her stepson gets the snot beat out of him. Jessica and Anthony pay Savvy and Dylan a visit. If Dylan wants to be a bully, Jessica will show him what a real bully looks like.
Format: mp4
Duration: 56:25
Video: 1920x1080, AVC (H.264), 2441kbps
Audio: 125kbps
File size: 1.0 GB
Related Posts Jessica Kay 40 000 Years of Anal Tears:
- Sedusa Anal Tears at 18 Years
- Assylum Anal Tears at 18 Years vol.2
- Assylum 40 000 Years of Anal Tears
- Sedusa Anal Tears at 18 Years vol.2
- Assylum Anal Tears at 18 Years
- Jessica Starling Jessica Stunning Anal Seduction HQ
- Brunette tears anal
- SeriousImages Amanda Wildefyre New Years Medical Toys New Years Part 2
- Claire 22 years old the shock encounter with Elena 27 years old 2020
- Very First Anal For New 19yo Busty Teen Jenny Tears