JavaScript Required. Please enable JavaScript in your browser in order to access this web site

Anal madness and extreme sexual domination | Assylum.com

Searching for: Crying

Kingdom of Ass & Pain Director's Cut

Kingdom of Ass & Pain Director's Cut

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.

Added on 02/25/24 | Full Video Inside
The Ass Bead Game

The Ass Bead Game

Filth Studies V

Presenting the 2.5 hour Museum Collection conclusion to the 5-part Filth Studies Series. Dr. Mercies went all out in this spectacular session, bringing in the uber-hot sadistic mistress Charlotte Sartre to help dominate Rebel. This time, Rebel was turned into a puppet, in an incredible bondage suspension that allowed her to move into any position in 360-degree space. Charlotte and the good doctor played a game of art, philosophy, and spiritual inquiry together as they whipped, paddled, ass-fucked, pissed on, and did everything imaginable to Rebel. There are huge anal toys, sadistic bodily fluid predicaments, control by feet, inverted ass eating, and more. For the first time ever, you'll see a girl get anally fisted with hot sauce while fanning her sadistic top so that the latter stays cool. And we are pretty sure this is first time that anyone anywhere has brought the great bead game to life.

Added on 12/10/23 | Full Video Inside
Blind Little Anal Pleaser

Blind Little Anal Pleaser

Filth Studies 3 - Rebel Rhyder

After several days of seeking art through anal suffering, Rebel and Dr. Mercies decided it was time to rest the eyes. For her, this meant donning a blindfold and focusing her remaining senses on pleasing all the doctor's harsh desires. They stripped away everything to seek beauty through raw submission, degradation, and service. And they found it. One of the best moments, perhaps, is when Rebel became Dr. Mercies' assfucked massage chair, taking it up her ass, massaging him as he rested, taking it up her ass again, and on and on. This scene is as authentic and down to Earth as it gets. Enjoy.

Added on 06/20/23 | Full Video Inside
Anal Strip Search

Anal Strip Search

Filth Studies 2 - Rebel Rhyder

Rebel's second session was so demented, ambitious, and intense that we spread it out over two days of delirious filming. It's hard to describe what happened here, because there really is nothing to compare this to on he planet. Rebel was turned into a working projector, suspended in nothing but film and used like a theater seat while she herself brought art to screen through her suffering. Dr. Mercies also trained her to pleasure his physical cock and shadow cock at the same time. And he used and punished her very, very hard. Her asshole, breasts, throat, and clit all got a workout. She ate two loads of cum in this session and had multiple giant orgasms herself. This is truly a pinnacle scene at Assylum.

Added on 05/20/23 | Full Video Inside
Punished Lily

Punished Lily

Lily Thot

Alas, we have reached Lily's final session from her recent stay at the Assylum. What this one lacks in creativity it gains in authenticity. You see, Lily did something bad: she slept through one of her previous sessions. So she and Dr. Mercies agreed she needed to be punished. Dr. Mercies punished her PAWG ass very hard with the vicious rubber tawse. He slapped her face. And he used her mouth roughly. You don't see many sessions like this at the Assylum, but Lily is a real-deal submissive masochist, and it was the right session at the right time.

Added on 12/20/22 | Full Video Inside
Pressed Lily

Pressed Lily

Lily Thot

By Lily's third day at the Assylum, Dr. Mercies was having mixed feelings. On the one hand, he found himself feeling a certain affection for sweet little Lily. On the other hand, her bratty masochism made him want to make her suffer. So he combined both feelings into one scene. Lily suffers for a long time under the doctor's ass as he punishes her, and she takes it hard and rough up her ass too. He presses her--literally with his ass and a pile of sandbags; but then they press a flower together at the end. This scene is very cruel and yet very tender and kind. Enjoy.

Added on 10/20/22 | Full Video Inside
Anal Quest for the Chalice of Sadistic Silliness

Anal Quest for the Chalice of Sadistic Silliness

Lily Thot

Exciting days at the Assylum, folks. Lily Thot, a super-hardcore and super-sweet masochist, came by for 3 days of submission. She's got a small body but a big, juicy butt, and Dr. Mercies made sure to treat it right... meaning horribly. Lily likes it ROUGH, and ROUGH is how she got it. This first session, a mythical anal quest, has rough painal, hard slapping and spanking, nasty carbon-fiber rodding, extreme cum play with the doctor's frozen cum, piss drinking, mental fuckery, and a sort of anal impalement. But it's also completely ridiculous and fun. It's the best of all worlds, really, with one of our best new anal perverts.

Added on 08/20/22 | Full Video Inside
Director's Cut--Sadistic Sustenance

Director's Cut--Sadistic Sustenance

Leah Winters

Warning: LEVEL 13 DIRECTOR'S CUT!!! The roughest anal fucking we've ever shot now includes an anal protein bar feeding. We shot this at the beginning of the pandemic. The original release was intended to explore the need for sadomasochistic companionship along with the other essentials during quarantine. This Director's Cut retains that theme while providing a fuller cut that showcases the absolute filthiness that occurred between Leah and Dr. Mercies. Please enjoy.

Added on 07/20/22 | Full Video Inside
Of Purity and Filth

Of Purity and Filth

Contrast Series, E2 | Rebel Rhyder

Folks, session #2 of Rebel's Contrast Series is here, and there are no words for it. First, let me remind you that Rebel is a genuine submissive masochist who enjoys extreme challenges. This session was eagerly created by all. But with that said, it goes heavy, and I mean very, very heavy in many ways, all at once. It's brutal, filthy, twisted, and nonstop intense for 2 hours (edited down from 3.5!). It also continues the mental and emotional journey begun in session #1. You see, we don't make everyday porn here. We make BDSM documentaries; we show people going on consensual journeys. Body, mind, and spirit is what it's about for us. In this case, few people on the planet besides Rebel could have gone on the journey. Please enjoy.

Added on 03/05/22 | Full Video Inside
In Deepest Painal May We Find Peace

In Deepest Painal May We Find Peace

Contrast Series, E1 | Rebel Rhyder

Ladies and Gentleman, we mark the end of the year with an extreme anal domination session like you've never before seen. Rebel Rhyder, the girl who can do what almost no other girl can, has returned to our Assylum for a 10-day visit of unbelievable proportions. And I mean that literally. In this first, 2-hour, epic installment of her many-hour journey, Rebel goes from gentle pussy eating to a brutal anal impalement session on a series of dildos so huge that even Vlad the Impaler would be proud. And yes, there is rough assfucking. And yes, there is piss. And yes, there is hard S&M. And yes, there is a mental journey--in fact, I'd call it a spiritual one--into the nature of the human condition. We present this scene not only for its rare physicality but for the heights to which it aspires. This is Assylum at its very best, and for that, we thank the one-and-only Rebel Rhyder. We also thank Hankey's Toys for providing the beautifully monstrous impalers that made this exploration possible.

Added on 02/05/22 | Full Video Inside
Smack-o-lantern

Smack-o-lantern

Xaya Lovelle

Warning: this is one of the hardest anal and ass punishment scenes we've shot. Xaya takes it very, very rough. She's an eager masochist, and before the scene began, she actually picked the hardest implements in Dr. Mercies' closet to be used on her: the ballbearing whip, the metal rod, the rubber baton, and the rubber strap, among others. Her beating coincides with painal, ass to mouth, and a strapping while dunked in piss. And did we mention the pumpkin? That's right, she carved her own pumpkin head to wear while being punished. Let me tell you, folks: having that 20-pound quasi-hood on your head takes everything to another level. We expect Xaya to be back on a regular basis. Her type is rare and special.

Added on 10/22/21 | Full Video Inside
Director's Cut: Punish my 19yo Ass

Director's Cut: Punish my 19yo Ass

Anastasia Rose

Special treat today, dear members! We've taken our most popular scene ever and completely re-edited and remastered it to create a 20% longer super cut! In this scene, Dr. Mercies and Anastasia did a little roleplay, pretending to cross paths outside. Bratty Anastasia needed a very hard punishment, with brutal assfucking and harsh, soapy face fucking, so that's what she got... in the Assylum bathroom. There's plenty of painal, ass to mouth, deep ass eating, and face slapping too. Enjoy.

Added on 07/24/21 | Full Video Inside
A World of Sodomy, Piss, and Pain

A World of Sodomy, Piss, and Pain

Lydia Black

On Lydia's first day at the Assylum, she earned her own unique mold. Now, on her second day, she has to prove she deserves it. This requires her to steadily inhabit her mold while Dr. Mercies brutally uses her for his sadistic and twisted pleasaure. Rough anal sex, tongue punishment, ass to mouth, rimming, piss enemas and piss drinking are all part of the challenge. Lydia also gets a harsh tongue beating and must then endure a rough face fucking with her sore tongue. This is a severe and intense update made possible by a wonderful masochist. Enjoy.

Added on 05/26/21 | Full Video Inside
Ass Cream Sundae Reward

Ass Cream Sundae Reward

Rebecca Vanguard

After 2 days of trial and use at the Assylum, Rebecca earned a reward from Dr. Mercies: an Ass Cream Sundae. Prior to the Sundae, Dr. Mercies had her eat out of his ass using an especially filthy, degrading technique designed specifically for her. This was accompanied by some brutal caning that had her crying into his ass. Then, once she finished her appetizer, he filled her ass with the sundae ingredients, made her squeeze them out, and then fed her the concoction while she orgasmed. We're pretty sure she enjoyed this. Rebecca is a very sick and twisted girl. We find her very fun.

Added on 04/26/21 | Full Video Inside
Quarantine Dreams--the Finale

Quarantine Dreams--the Finale

Leah

Leah was already brutally dominated 3 times in a row. And now, for her last day with him during their lockdown together, Dr. Mercies put her up to an even more intense challenge. He kept this session simple and gimmick-free. This one is about sheer physicality and mental connection. As a rare "Assylum Uncensored" release, this session shows things that normally don't get shown. Enjoy.

Added on 06/15/20 | Full Video Inside
Sadistic Sustenance

Sadistic Sustenance

Leah Winters, Quarantine Dreams 2

The day after Leah Winters and Dr. Mercies made Submission, Inc, she came back for this. Despite her ass (and the rest of her body, really) having already being roughly used, the good doctor decided to use it even harder today. As he had gotten to know Leah, Dr. Mercies had learned that she's an absolute sponge for domination, sadism, and extremely rough anal usage. The result from day 2 of their quarantine together is very harsh. Dr. Mercies' fucks her ass from every angle while also punishing her pussy and stomach. But it's also quite tender, as they were both very thankful to each other for their time together. Note that this session was self-filmed by Dr. Mercies.

Added on 04/24/20 | Full Video Inside
Anal Table Manners

Anal Table Manners

Rebecca Vanguard

The night before Rebecca'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.

Added on 03/12/20 | Full Video Inside
One Ass, Six Versions of Anal Sadist

One Ass, Six Versions of Anal Sadist

Rebecca Vanguard

Rebecca 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 Rebecca 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 by Dr. Mercies' idiot version of himself, and subjected to a humiliating and painful dance in clamps by jester Mercies. All in all, it was 90 minutes of sadistic domination. I think she felt good to get through it and get something out of herself.

Added on 02/19/20 | Full Video Inside
Anal Crazy School (aka P-EYE-NAL)

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 again. Finally, he gave her an extra concentrated piss enema and made her drink it all. Poor Lexi's eyes and ass were burning this whole 90-minute scene. And she was not allowed to come or have any pleasure. But this is what she wanted and needed; make no mistake about it.

Added on 01/16/20 | Full Video Inside
Rebel's Initiation (aka Hardest Gangbang Ever Shot)

Rebel's Initiation (aka Hardest Gangbang Ever Shot)

Order of the Red Star: Rebel Rhyder

No marketing hype: this is the hardest gangbang ever shot, as well as one of the longest ones. 3 hours of nonstop, sadistic anal insanity with a beautiful, big-ass babe and 4 brutal dominants. This scene has extreme anal stretching, very rough ass fucking, heavy caning and paddling, anal electrical play, upside down rope suspension, interrogation, lots and lots of piss, ass to mouth, foot and boot worship, ass eating, and just a profound level of physical and mental challenge. Let it be clear: Rebel is a submissive masochist and wanted this scene. That's why we have included the full consent discussion in this release. Also, be sure to watch the post-interview discussion for context. We present this scene not only as a rare piece of entertainment but as what we believe will be a valuable, educational glimpse into the practice of BDSM.

Added on 11/21/19 | Full Video Inside
[1] 2 3 4 »

Join the ward to see all the sessions