Punishment painfully porn Videos

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Games of Goddess Kyaa River Endza Abigail Dupree Goddess Kyaa Navojoa

Genres: Bondage, BDSM
Video language: English
In this first scene that Goddess Kyaa has prepared, She has Her slave River and slave Abigail tied up in a little challenge that will test their teamwork abilities. The two slaves could not contrast each other any more than they do with slave River in light pink from head to toe and towering almost a foot over slave Abigail who is in all black. Scattered on the floor is a variety of different sized weights and a box of pebbles. Goddess Kyaa has them cuff each others hands behind their backs and proceeds to tether them together using clover clamps on their tits and a piece of twine between them that hosts a singular hook. Their goal is to move as many weights as they can in 3 minutes, from the floor to the box of pebbles using only the hook. It proves to be harder than they both expected. After failing miserably, Goddess Kyaa has no other option but to punish them for being such losers. She obviously enjoyed herself though as I think you will too.
Format: mp4
Duration: 18:11
Video: 1920x1080, AVC (H.264), 6835kbps
Audio: 156kbps




File size: 933.1 MB


DOWNLOAD FROM FILESMONSTER: Games of Goddess Kyaa River Endza Abigail Dupree Goddess Kyaa

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Stefanos' Brunch Oldhams

Cast: Dylan Ryan ,Beretta James
Genres: bottom ,Discipline ,slim ,Humiliation ,master ,Rough Sex ,brunch ,mixed ,BDSM ,natural boobs
Video language: English
The House has another Brunch filled with amazing BDSM debauchery. Tramp and pistol are punished in front of the guests by the Steward, and tramp is made an example of. The party moves to the lounge, pistol is put in a cage and the guests are allowed to have their way with her while tramp services another guest.
Format: mp4
Duration: 57:54
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 632.9 MB


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Lupus pictures bonus movie part 3 Frenchville

Release Year: 2005
Studio: Lupus Pictures
These are higher quality encodes than the versions shared here a few years ago. We can now view these classics as they were meant to be seen, with 50FPS bringing a new level of clarity to the punishments contained within.
Format: mp4
Duration: 1:15:49
Video: 720x576, AVC (H.264), 3241kbps
Audio: 250kbps



File size: 1.9 GB


DOWNLOAD FROM FILESMONSTER: Lupus pictures bonus movie part 3

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Rougher, Harder, Crazier! Kenzie Vaughn Cedar Point

Cast: James Deen ,Kenzie Vaughn
Genres: Rough Sex ,brunet ,Blowjob ,Submission ,Corporal Punishment ,shaved ,Anal ,Rope Bondage ,Kinky ,Domination
Video language: English
Gorgeous model with a perfect body, Kenzie Vaughn, gets treated like a filthy bondage whore. Sex and Submission brings you the hottest girls doing the most extreme kinky sex. You would never expect such a beautiful and seemingly innocence looking girl to get so turned on by the rough anal sex and strict bondage that James Deen dished out. Her DD breasts, nice round ass, completely shaved pussy, big eyes and mischievous smile draws the viewer in. Sex and Submission does what you can’t find anywhere else, combine intense rough sex with real sexual passion and chemistry.
Format: mp4
Duration: 1:05:59
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps



File size: 721.0 MB


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Synchronicity in Servitude Drake

Cast: Dylan Ryan ,Beretta James
Genres: natural boobs ,Rope Bondage ,Blonde ,master ,fake boobs ,slim ,bottom ,Corporal Punishment ,Anal ,Discipline
Video language: English
Synchronicity: the experience of events that are apparently unrelated, yet are experienced as occurring together in a meaningful manner.
A staff of slaves runs on teamwork. Teamwork relies on knowing your team mates. Knowing is being. And these two slave will ‘be’ each other until they get it right. Now, slaves, go fuck yourselves.
The household gathers to help us get the slaves in synch. They fuck themselves in synch, they are bound together on synch, they fuck each other in synch. The crowd is inspired and soon sex, whips and bondage break out among the guests, filling the room with the smell of servitude.
Format: mp4
Duration: 57:54
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 633.3 MB


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Cards of pain pt. 1 Plattenville

Release Year: 2019
We developed a new pain game and its first contestant is Lucy. In this game the player must devide 100 strokes between five of her body parts: Soles, Pussy, Tits, Bottom and Back. She wins the game and the huge prize only if she takes all five punishments. But there is one catch. She must draw a lucky card (or we should better call them unlucky cards) for each of the five punishments which slightly modifies the original punishments. These cards may contains virtually anything, double up the number of strokes, add a further punishment, change the body part or the way the punishment is executed... Will Lucy this time win the game?
Format: mp4
Duration: 1:01:09
Video: 1280x720, AVC (H.264), 3900kbps
Audio: 184kbps



File size: 1.8 GB


DOWNLOAD FROM FILESMONSTER: Cards of pain pt. 1

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Penny Play Navarre

Cast: Claire Adams ,Penny Barber
Genres: natural boobs ,Anal ,BDSM ,LezDom ,Dominatrix ,shaved ,Slave ,Corporal Punishment ,Fingering ,Femdom
Video language: English
Penny Play has an innocence about her that makes watching her in extreme bondage that much more enjoyable. She takes on some serious rope ties and punishment administered by Claire Adams. Great chemistry and hot action not to be missed!
Format: mp4
Duration: 1:09:17
Video: 960x540, AVC (H.264), 1365kbps
Audio: 122kbps



File size: 756.3 MB


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Lupus pictures bonus movie part 1 Ickesburg

Release Year: 2002
Studio: Lupus Pictures
Genres: BDSM, Spanking, Punishment
Hot Czech girls mercilessly spanked and caned for our amusement! These bonus packs from Lupus Pictures still contain some of the very best spanking cinema to date and most of these scenes are around 20 years old now.
Format: mp4
Duration: 1:42:34
Video: 720x576, AVC (H.264), 3186kbps
Audio: 250kbps



File size: 2.5 GB


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Service pt. 4 Erlanger

Release Year: 2010
Studio: TheUpperFloor
Inspired by the legendary French Bdsm erotic novel The Story of O, TheUpperFloor illustrates real lifestyle Bdsm as it is lived by 24/7 slaves and Masters, complete with extreme BDSM, explicit sex in bondage, punishment, erotic humiliation, and more. At Kink's The Upper Floor, slaves become willing playthings for cruel Masters and Mistresses. Porn stars with submissive desires come to TheUpperFloor to be trained as slaves; lifestyle slaves may beg for real life slave training or be given by their Masters or Mistresses to the Upper Floor. TheUpperFloor is where these submissive kink players become playthings for sexual Dominants and the guests of Kink.
Format: mp4
Duration: 1:16:04
Video: 1280x720, AVC (H.264), 4882kbps
Audio: 122kbps



File size: 2.7 GB


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Artemisia Love & Sarah Arabic - Busty Babes’ Boob Therapy Tishomingo

Release Year: 2024
Cast: Artemisia Love, Sarah Arabic
Genres: Brunette, Big Ass, Big Tits, Blowjob, Close Up, Deep Throat, Doggystyle, Facial, Hardcore, Handjob, MILF, Masturbation, Mature, Natural Tits, POV, Shaved, Straight, Threesome (FFM)
Video language: English
Kai has a rather odd obsession with his stepmom Artemisia’s breasts. He stares at them constantly, follows Artemisia around the house, and tries to fondle her occasionally. Fed up with her stepson’s attitude, Artemisia hires Sarah, the super nanny who specializes in these kinds of fixations. Sarah has a strict approach to teaching young perverts like Kai. First, she pulls her massive tits out and asks Artemisia to do the same. Then, they put Kai to the test, forcing him not to touch their sweet jugs while still getting a good eye on them. Next, he receives his first real punishment: watching hours of motorboating videos. The plan quickly backfires as Kai ends up jerking off obsessively to these vids. That’s when Sarah realizes that the problem is much bigger than she thought and that they should be trying a different method. Asking Artemisia to take her shirt off again, they try some aversion therapy by giving Kai a titjob and sucking his cock while also sprinkling some water on him to try and generate self-control on the kinky boy. Finally, Artemisia and Sarah realize that they had it all wrong. It’s not through rejection that Kai will learn to cope with his obsession. He’s still a virgin and he just needs to have sex to make those intrusive thoughts go away. Artemisia and Sarah join forces to give Kai one filthy first time to finally cure Kai’s obsession.
Format: mp4
Duration: 55:42
Video: 1920x1080, AVC (H.264), 5827kbps
Audio: 155kbps



File size: 2.4 GB


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Human Furniture Defuniak Springs

Cast: Lorelei Lee ,Dutch Bardoux
Genres: Orgasm Denial ,Pegging ,Dominatrix ,Male Sub ,natural boobs ,foreskin ,Bondage ,body builder ,Slave ,Corporal Punishment
Video language: English
Lorelei Lee loves when a fresh piece of man meat is given to her to use as she sees fit. When Dutch Bardoux arrives at the steps of the Armory Lorelei, Madeline and Madeline’s all girl crew aren’t quite sure what to make of him. He’s a stocky, beefy muscle type who didn’t have much to say so Lorelei decided it best to objectify him and make him into a piece of human furniture. As soon as Dutch is put in bondage, made into an object, has his balls stomped on, spanked, flogged, waxed, humiliated and strap-on butt fucked he suddenly opens up and becomes an obedient slave and a slutty piece of man meat! Lorelei has so much fun putting his head into the face sitting box and makes him sniff, worship and lick her pantyhose and ass. She uses his dick to get off until he’s begging to cum. She then lets him blow his load alright but only at the cost of wearing his filth all over his face!
Format: mp4
Duration: 52:44
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 576.3 MB


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Porno Barbie: Lesbian bondage, domination,and anal strap-on fucking! Kennedale

Cast: Lea Lexis ,Missy Martinez
Genres: black hair ,Corporal Punishment ,Sub ,Caning ,Curvy ,Bondage ,Humiliation ,Anal ,Domination ,BDSM
Video language: English
The Dollhouse series returns with bombshell barbie doll, Missy Martinez and hot latex clad dominatrix Lea Lexis. Lea tests the abilities of her pretty plaything with bondage, finger banging, pussy licking, spanking, flogging, caning, facesitting, and pussy and anal strap-on fucking!!!
Format: mp4
Duration: 1:02:39
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 686.7 MB


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Caged Redhead Spring Creek

Cast: Cherry Torn ,Sophia Locke
Genres: BDSM ,LezDom ,Anal ,Dominatrix ,Corporal Punishment ,Slave ,Redhead ,Humiliation ,other hair color ,Fingering
Video language: English
Sexy redhead, Sophia Locke, makes her explosive debut on Whipped Ass. Sophia really loves BDSM. She’s kept in our new hanging bird cage and fucked deep in her cunt. Sophia has intense genuine reactions to everything that Cherry Torn dishes out and the girls have amazing chemistry!
Format: mp4
Duration: 1:01:25
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 673.2 MB


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The prospective maid Spring Grove

Release Year: 2016
Studio: Captivechrissymarie
Genres: BDSM, Spanking, Fetish, Bondage, Glamour
I run a local housecleaning business on the side, but things have been particularly slow lately, so I went on a few new websites and after some searching found an ad for someone needing a maid on a regular basis. This could be a great steady income, but he requires and interview before he can guarantee the job. I arrive right on time, dressed ready to do some cleaning in my shorts, tank, sneakers and bandana to keep my long hair out of my face when I'm working. I knock and an attractive man answers the door. We seem to get along well as we start discussing the job, but he does mention that he has some strange requests for his maids, which is why he pays so highly. I tell him no problem, with my experience I'm sure it's nothing I can't handle. I get to work cleaning the dining area and I must admit it's a little disconcerting to be watched so closely, but he reassures me that I'm doing a great job. Then he brings up his first request: He likes his maids to be nude while cleaning. I hesitate as I am not that type of housecleaner, but he mentions he knows my business is struggling and that I really need the money. Unfortunately I really do, so I decide it can't be that bad, as I strip down to just my socks and get back to work. Next he brings up another surprise, that after his maids are finished cleaning, he likes to tie them up for his viewing pleasure! This really makes me uncomfortable, but I don't want to lose the cash now that I did all that work, completely naked, that would be so humiliating! I tell him it's a really strange request, but I guess I'll try it. He throws me a rope and asks me to start tying my ankles, before going on to tie my wrists and thighs for me and cleave gag me with the bandana off my head! He moves me back to the living room and orders me to struggle while he watches me. Then he decides he wants to see my bare feet, so he removes my white ankles socks to expose my soles. I keep struggling but really start to get tired of it and ask to be let out, but he doesn't listen, and instead starts fondling me! This was not part of the agreement! I try to fight it, but being all tied up, I can't really do anything about it. Then his touch starts to involuntarily arouse me, and I start to think about how it is kind of hot to feel so helpless as this man controls me. My moans start to turn less distressed and more pleasured as he gropes me, and before I know it he has me under his spell and I'm telling him that I'm a very bad maid who needs to punished!
In Part Two, it's time for the next part of the interview and to see how well I can endure a harsh punishment. I've spent the majority of the interview up to this point feeling quite uncomfortable with the whole situation. I even asked to be untied at one point, however he did not let me go and instead started fondling me until I reached the point where I was under his control and actually started to enjoy it, begging him to punish me for being a naughty maid! He bends me over on the couch and starts whipping me with a flogger on my ass and thighs. The combination of pain and pleasure is unlike anything I've ever experienced. As he gets rougher and rougher, my faint moans start to turn more agonizing. I know if I can just endure this last part of the interview, I will definitely get the job, and I really need the money. If I have to endure it, I'm going to try to enjoy it as well. He moves on to whipping ass and bare soles before flipping me over on my stomach and giving me a good old fashioned hand spanking to finish it off, leaving me with a bright red behind and nearly in tears, but then he gives me the great news that I'm hired and will be back same time next week. I ask him if perhaps I'll actually do some more cleaning next time, and he says we'll see about that!
Format: mp4
Duration: 22:15
Video: 1920x1080, AVC (H.264), 8388kbps
Audio: 241kbps



File size: 1.4 GB


DOWNLOAD FROM FILESMONSTER: The prospective maid

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Exposed, Fucked and Humilated all in Public Kalaupapa

Cast: Tommy Pistol ,Jacqueline Black Lady ,Princess Donna Dolore
Genres: Rough Sex ,Discipline ,Humiliation ,Public ,Ball Gag ,natural boobs ,BDSM ,Anal ,Blowjob ,Feet
Video language: English
Jacqueline walks the bridge with sticky pads electrifying her ass, sending the shock waves down her legs all the way into the heels of her pretty little feet. She is helples, no one but Tommy Pistol to dominate her in the streets of Berlin.This is just the beginning of her long day outside where anyone can see Jacqueline get fucked, slapped, punished and humiliated, and no one can help her. Princess Donna Dolore and Sir Tommy will own Jacqueline until they are done, fucking her in the subway, at the loading dock, the Olympic Stadium…anywhere they please to open her legs and take advantage of their little whore.
Format: mp4
Duration: 55:43
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps



File size: 608.8 MB


DOWNLOAD FROM FILESMONSTER: Exposed, Fucked and Humilated all in Public