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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…

Assylum – Rebel Rhyder – The Impossible Anal Journey

Level 13 anal masochist Rebel Rhyder returns in this first, 1-hour episode of a 4-session mega-epic! This episode is filled with rough painal, deep ass eating, piss drinking, and harsh play with very large anal toys. But it’s also got some other things you might not expect: a beautiful film from 1904 called the Impossible Journey to kick off this unique, authentic exploration of body and soul with Rebel.

Ass Not Done Yet – Rebel Rhyder

After Rebel’s 3-hour gangbang, in which she was entirely damaged, she went to make use of the shower and obtain dressed. That’s when Dr. Mercies grabbed her and also informed her that her experience was not yet full. He supplied the final part of her initiation into the Order of the Star. This suggested that her wrecked asshole (as well as rest of body) was plundered all over once more. This scene is very short. However it’s raw, harsh, and…

Assylum – Anal Table Manners – Sailor Luna

The night before Sailor’s epic session in the padded cell, I invited her to dinner. I had noodles. She had noodles too… from her ass. There was much painal to go along with them. And giant pickle insertions. And ass hair removal via pliers. And piss. She said she needed this. It’s been hard for her to find a sadist who delivers. It was a good meal for them both.

One Ass, Six Versions of Anal Sadist – Sailor Luna

Sailor has wanted to visit the Assylum for a long time, because she has trouble finding a strict dom to put her in her place. So Dr. Mercies gave her a firm introduction to the Assylum style of hard anal domination. He wore one hat after another, assuming various identities, and made Sailor submit to them all. She got severely ass stretched by pirate Mercies, suspended by gentleman Mercies, worshipped King Mercies’ ass, savagely anally raided by Viking Mercies, beaten…

Assylum – Anal Crazy School (aka P-EYE-NAL) – ANAL CRAZY SCHOOL

Lexi needed to be punished hard, and Dr. Mercies was feeling extra cruel. So they made this scene together. First, Dr. Mercies came in Lexi’s eyes (after making her tongue-clean his ass, feet, underwear, and the inside of his boots). Then he fed her a piss popsicle while beating her ass with a heavy paddle and his gnarliest set of anal beads. Then he put her in a straightjacket and used soapy lube to fuck her ass until he came…

Assylum – Blender Studies Director’s Cut – Charlotte Sartre

A member favorite with the incredible, filthy Charlotte Sartre… now with 20% more footage. There may be some things we still can’t show you from this scene, but we think you’ll enjoy the extra enemas and ass squirting, as well as Charlotte talking about her expectations before the scene began. This one is nasty and edgy. Enjoy the pressure release.

Assylum – Wet Painal

Violet’s ass was still sore from the previous day’s brutal anal domination session. She was also a bit nervous about Dr. Mercies’ enema syringe. This made her extra fun. Dr. Mercies bent her over the table and fucked her ass very rudely before giving her a nice, big enema. She had to come with that enema inside her while Dr. Mercies rolled her belly flat with a carpet roller. Yes, this scene is a bit fucked up. But Violet makes…

Assylum – I Am whore, Asswhore I am

Delirious is a hot, blond anal painwhore who recently helped Dr. Mercies overcome his sad feelings. Now that he is feeling better, he is back to his anally sadistic self. He gives Delirious a very special treatment by binding her in zippers that open and close on all of her holes. Then he and Orderly Grind savagely fuck her ass and mouth. Both men drown her face in their cum and make sure to give her the ass smacking,…