Punishment painfully porn Videos

[TZFotiwof]

MILF gets tormented and machine fucked Henefer

Cast: Orlando ,Simone Sonay
Genres: Blonde ,Corporal Punishment ,shaved ,Domination ,Metal Bondage ,black hair ,Handler ,BDSM ,MILF ,Latinx
Video language: English
Simone is put in grueling positions that leave her helpless to the desires of her captor. She is tormented in ways that she didn’t know were possible and made to cum harder than she ever has before.
Format: mp4
Duration: 1:01:41
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 676.0 MB


DOWNLOAD FROM FILESMONSTER: MILF gets tormented and machine fucked

[TZFotiwof]

Maid for Punishment Earp

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


DOWNLOAD FROM FILESMONSTER: Maid for Punishment

[TZFotiwof]

Casey Calvert Cyd Black In Heat Nantou County

Genres: Anal, Ball Gag, BDSM, Bell, Bondage, Butt Plug Tail, Chain leash, Chains, Dildo, Domination, Drool, Flogging, Gag, Handcuffs, Kitten, Metal Collar, Milk, Mittens, Nipple Clamps, Orgasm, Pet Play, Ring Gag, Stockings, Tape Gag, Toys, Vibrator, 720p
Video language: English
Casey Calvert and I have a lot of fun together. We have our private games that we like to play. Today I brought her a present, a pair of cat ears and a tail. The ears are on a convenient little headband but to wear the tail she is going to have to insert a pretty sizable plug into her ass.
If I let her crawl around with opposable thumbs it will break the fantasy. Instead I tape her hands with vet wrap, turning them into perfect paws. Her legs get bent so that she has to crawl around on her fists and knee caps. It amuses me to watch her play on the ground like an animal.
A good kitty gets a prize. It's time with every pussy's favorite toy, the Hitachi. It's the most powerful hand held vibrator you'll ever see and it does a number on Casey's dripping wet pussy.
We're about more than just fun and games, though. There is an element of discipline that comes with having pets, even cats. Some tough corporal punishment will remind Casey that I'm in charge here, that I'm her master and owner, and she is my property. Floggers and canes are an ideal way of reinforcing the power structure and keeping my pets obedient.
That thing she thought was just her scratching post has another purpose. Turned sideways it makes for a brutal horse for her to ride. Unlike most, which come to a point, this one is flat on the side, but the ropes wound around it dig into her crotch as her weight presses down. When she rocks her hips backward to allow my vibrator access to her clit you can clearly see the marks that the rope has left.
Format: mp4
Duration: 1:10:51
Video: 1280x720, AVC (H.264), 2696kbps
Audio: 105kbps



File size: 1.5 GB


DOWNLOAD FROM FILESMONSTER: Casey Calvert Cyd Black In Heat

[TZFotiwof]

Misstreatment Lichtenfels

Release Year: 2016
Studio: Assylum
Cast: Delirious Hunter
Genres: Ass fucking, Ass to mouth, Asslicking, Facial, Nasty cum play, Rough oral, Spitting, Caning, Crying, Face slapping, Paddling, Pain, Punishment, Screaming, Spanking
Video language: English
Gag-fucked while getting her ass beaten, Delirious Hunter starts to cry a little. But her tears taste bitter, so Dr. Mercies rips apart her candy bra and uses the candy to sweet her teardrops. Then he cums all over her face and applies crackling candy to the cum. As if that weren´t enough, Orderly Sinn shows up and starts to hatefuck Delirious´s already degraded mouth and asshole just when she thinks her therapy is done. (This therapy session also has lots of ass eating and caning and paddling.)
Format: mp4
Duration: 23:52
Video: 1280x720, AVC (H.264), 2385kbps
Audio: 124kbps



File size: 440.2 MB


DOWNLOAD FROM FILESMONSTER: Misstreatment

[TZFotiwof]

My Only Joys Are Yours, Sirs Norborne

Release Year: 2017
Studio: Assylum
Cast: Paige Pierce
Genres: Anal toys, Ass fucking, Ass to mouth, Asshole pain, Asslicking, Painal, Rough oral, Bondage, Caning, Crying, gagging, Mind fucking, Pain, Punishment, Screaming, Spanking, Training, Big ass, Tattoos
Video language: English
Paige is a bratty alt-type girl who needs to be put in her place and put there hard. We don´t hold back with this one at all. Dr. Mercies dives deep into her head, with some heavy domination and sadistic mindfucking while Orderly Rex reams her big ass with his long, hard cock. Over the course of her therapy session, Paige learns to forget all her joys and focus instead on what makes the staff at the Assylum happy. You won´t find anything like this anywhere else. This is a hardcore treatment documentary.
Format: mp4
Duration: 54:51
Video: 1280x720, AVC (H.264), 1738kbps
Audio: 124kbps



File size: 751.8 MB


DOWNLOAD FROM FILESMONSTER: My Only Joys Are Yours, Sirs

[TZFotiwof]

Ginger South Kent

Cast: Ginger
Genres: shaved ,natural boobs ,LezDom ,Cattle Prod ,Electro Clamp ,Corporal Punishment ,Dominatrix ,Slave ,Electrical Play ,Facesitting
Video language: English
Chanta has forgotten her ID and Ginger won’t bring her a glass of wine…not a smart move when there is a hand bag of electrical toys close by! Ginger is tied up, electrified and made to cum before being bent over and fucked with Chanta’s electric strap on.
Format: mp4
Duration: 25:06
Video: 640x480, AVC (H.264), 1171kbps
Audio: 122kbps



File size: 238.3 MB


DOWNLOAD FROM FILESMONSTER: Ginger

[TZFotiwof]

The Assistant Ulu Kelang

Cast: Jessica Kay
Genres: BDSM, Humiliation, Torture
Video language: English
Jessica Kay got into this gig thinking that if she hung around long enough then maybe O.T. would notice her and decide to use her in the same way he does all of the models that come onto the set. She doesn't want to be on video, she has no interest in being a star, but Jessica definitely wants to be dominated and she has become obsessed with being the next girl he handles.
Her plan is simple, if she dresses like a slut enough then O.T. won't be able to help himself. Or so she thinks. Well, it pays off once, but not in the way that she thinks. Sure, O.T. uses her, but it comes with conditions. She isn't going to be strutting around the office wearing skirts so short her panties peek anymore. She'll be nice and professional.
But Jessica isn't a quitter. She wants to be dominated daily and she'll do whatever it takes to make it happen. Sure enough, things start slipping through the cracks and she needs to be punished again. Metal bondage, corporal punishment, and more than a few orgasms are coming for her. It may be counter productive and just encourage her to mess up more, but O.T. is tired of her screwing around so if nothing else works he is going to give her more of what she wants than she'll know how to handle.
Format: mp4
Duration: 52:30
Video: 1280x720, AVC (H.264), 7310kbps
Audio: 109kbps



File size: 2.8 GB


DOWNLOAD FROM FILESMONSTER: The Assistant

[TZFotiwof]

Sandra Romain and Julie Night Dinosaur

Cast: Sandra Romain ,Julie Night
Genres: shaved ,Slave ,Anal ,Corporal Punishment ,Pain Slut ,Fingering ,slim ,Humiliation ,Femdom ,Facesitting
Video language: English
Julie Night really comes alive as a submissive and is one of the toughest pain sluts we know. Locked inside a small cage down in the scary Armory basement, she awaits her tormentor, Sandra Romain. Nothing is made easy for Julie and she must try hard to please Sandra with her tricky games and punishments. As her final act of submission, she is fucked in the ass while suspended sideways.
Format: mp4
Duration: 1:08:48
Video: 960x540, AVC (H.264), 1365kbps
Audio: 122kbps



File size: 750.9 MB


DOWNLOAD FROM FILESMONSTER: Sandra Romain and Julie Night

[TZFotiwof]

Training Of Holly Heart, Day Four Wellpinit

Cast: Holly Heart ,Maestro
Genres: master ,Bondage ,Role Play ,Caning ,Gimp ,Female Slave ,Discipline ,black hair ,Corporal Punishment ,Humiliation
Video language: English
Judgment day for sex slave Holly Heart as she demonstrates anal skills and caning with a sense of dignity and humility in front of the household.
Format: mp4
Duration: 1:14:06
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 810.0 MB


DOWNLOAD FROM FILESMONSTER: Training Of Holly Heart, Day Four

[TZFotiwof]

Punish my ass as I pleasure yours Mellen

Release Year: 2017
Studio: Assylum
Cast: Anastasia Rose
Genres: Ass fucking, Ass to mouth, Asseating antics, Asslicking, Cum swallow, Facial, Painal, Rough oral, Bondage, Breast pain, Crying, Face slapping, gagging, Punishment, Spanking, Whipping, 1821
Video language: English
19 year-old Anastasia gets a hard painal fucking and eats a lot of ass while tied in a demented chair predicament. If you´ve never had a metal chair tied to your shoulders while getting assfucked, then you can´t imagine what an intense session this was for her. It´s one of our hardest, and because she enjoyed it, it was one of our best. She´s not cured yet, though. Not at all.
Format: mp4
Duration: 23:59
Video: 1280x720, AVC (H.264), 1941kbps
Audio: 121kbps



File size: 363.8 MB


DOWNLOAD FROM FILESMONSTER: Punish my ass as I pleasure yours

[TZFotiwof]

Built for Anal Larue

Release Year: 2016
Studio: Assylum
Cast: Tangled Tanzi
Genres: Ass fucking, Ass to mouth, Asslicking, Cum swallow, Double anal, Facial, Huge toys in ass, Rough oral, Bondage, Training, Amateur
Video language: English
Double anal punishment awaits this bratty masochist as we pry and hammer open her asshole with demolition tools. We tell her that her we´re going to treat the brat in her hard so that she learns to be a good, obedient, submissive whore instead. Orderly Damian, our new staff member, pounds her asshole while she is bound with measuring tape and a level and balanced on one leg. "Stay level," he tells her, before jamming a dildo into her ass alongside his cock. Tanzi is also made to tongue Orderly Damian´s and Dr. Mercies´ asses for a long time and do lots of nasty ass to mouth and face fucking. Honestly, the treatment failed, because this pervert liked it too much. But we´ve got more punishment in store for her. This is just the beginning of her anal therapy.
Format: mp4
Duration: 45:08
Video: 1280x720, AVC (H.264), 2422kbps
Audio: 125kbps



File size: 844.7 MB


DOWNLOAD FROM FILESMONSTER: Built for Anal

[TZFotiwof]

Teen Nurse Shocked Into Proper Office Behavior Staunton

Cast: Cherry Torn ,Kendra Cole
Genres: Tattoo ,Tens Unit ,Anal ,Electro Clamp ,bottom ,natural boobs ,Corporal Punishment ,Gay ,slim ,Lesbian
Video language: English
You can’t blame her, really. Kendra Cole is only 19 and hasn’t had enough work experience to know much about business casual; that she can’t go traipsing around the hospital ward dressed in tight, short dresses that don’t even try to conceal her young ass.
Dr. Cherry Torn, however, has no patience for such excuses. She’s seen this naive slut fuck every RN in the building and decides if Kendra can’t keep her pussy dry, then she better share with the whole office. Starting with the boss!
Kendra is assigned a full day of electrotraining, starting with some TIGHT bondage and a DEEP, penetrative fuck with the violet wand. Then she is pretzeled over the desk with sticky pads shocking her ass, holes wide open for Dr. Torn’s NEW, bigger + stronger Samurai and a DOS that Kendra’s pussy has no problem cumming on, again and again. She’s made to eat her boss’s cunt til her face is covered in cum and then tzapped to complete electro submission.
Format: mp4
Duration: 59:17
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 649.8 MB


DOWNLOAD FROM FILESMONSTER: Teen Nurse Shocked Into Proper Office Behavior

[TZFotiwof]

The Girlfriends Bertrange

Cast: Mona Wales ,Lotus Lain ,Dolly Leigh
Genres: shaped ,shaved ,Dominatrix ,Rimming ,Facesitting ,Gag ,Slave ,Corporal Punishment ,black hair ,bottom
Video language: English
Lotus Lain has moved in with Dolly Leigh’s ex boyfriend. Previously, Dolly turned his man cave into domesticated heaven right before he broke up with her. Now Lotus is reaping all the benefits. Attorney, Mona Wales, mediates the argument and poses unique solutions to their problem. Forget the ex, make up and fuck! The ladies aren’t as willing and Mona has to use dominance to teach them a lesson. Spanking, pussy licking, ass licking, strap-on anal, dildo gag and more!
Format: mp4
Duration: 1:03:43
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 698.4 MB


DOWNLOAD FROM FILESMONSTER: The Girlfriends

[TZFotiwof]

Sarah Jessie Slips In Her Back Door Lover Oshawa

Release Year: 2025
Cast: Sarah Jessie
Genres: Anal, BDSM, MILF, Hardcore, All Sex
Video language: English
Dirty milf Sarah Jessie gets dominated, face fucked and rough assfucked in airtight bondage. It isn't punishment, it is just her lot in life.
Format: mp4
Duration: 43:48
Video: 1920x1080, AVC (H.264), 11683kbps
Audio: 122kbps



File size: 3.7 GB


DOWNLOAD FROM FILESMONSTER: Sarah Jessie Slips In Her Back Door Lover

[TZFotiwof]

Rule-Breaking Teacher Fucks Step-Sibling Students Katie Morgan & Aubree Valentine Fremont Center

Release Year: 1998
Aubree pushes her stepbro Austin into the empty classroom. She wants to pull the ultimate senior prank: having Austin cum in their teacher’s cup of morning coffee. Austin is uncertain, but his devious stepsis convinces him by sucking his cock. Unfortunately, Ms. Morgan, the teacher, walks in and notices something weird going on. Austin tries to hide the whole situation but he accidentally cums inside his stepsis’s mouth. Ms. Morgan soon realizes what’s going on and scolds the two pervy step-siblings, marking them for summer school. Later on, hoping not to face their punishment, Aubree and Austin enter Ms Morgan’s classroom while the teacher is grading their finals. They try begging her not to give them summer school as it is their last summer vacation ever, but Katie isn’t listening to reason. Desperate, Aubree tries to convince her another way. She heard rumors about Mrs. Morgan has a kinky lesbian side, so she starts playing with her teacher’s cunt. Little do Aubree and her stepbro know that, once their teacher has tried their sexual talent, Summer School will be her excuse to fuck both of them!
Format: mp4
Duration: 37:12
Video: 1920x1080, AVC (H.264), 1845kbps
Audio: 125kbps



File size: 539.2 MB


DOWNLOAD FROM FILESMONSTER: Rule-Breaking Teacher Fucks Step-Sibling Students Katie Morgan & Aubree Valentine