Punishment painfully porn Videos

[Bowezab]

Hogcuffed 2006-2011, part 1 Nienburg

Bodysearches and humiliating punishments, including fucking the warden with a mouthgag with a dildo on it. Sucking dicks and being strapped down in straightjackets or to a metal frame with a dildo shoved up the pussy can also help inmates learning how to behave. The guards and the warden often tease and arouse their prisoners, leaving them tied up with no chance to touch themselves...
Format: mp4
Video: 768x576

Total size: 6.8 GB in 50 files.

DOWNLOAD FROM FILESMONSTER: Hogcuffed 2006-2011, part 1

Subspaceland - Unexpected Punishment Helmstedt

Release Year: 2016
Studio: Subspaceland
Cast: Danielle Soul
Genres: BDSM
Video language: English
Danielle Soul thinks he is going to train her body, but he ends up training her mouth and throat instead.
Format: mp4
Duration: 23:48
Video: 1920x1080, AVC (H.264), 4337kbps
Audio: 184kbps

File size: 789.3 MB


DOWNLOAD FROM FILESMONSTER: Subspaceland - Unexpected Punishment

Subspaceland - Home Corporal Punishment II New Paris

Release Year: 2016
Studio: Subspaceland
Cast: Bunny Babe
Genres: BDSM
Video language: English
The torment and home corporal punishment continues for cute submissive painslut teen ball-gagged and ropes tied then spanked and pussy fingered hard. Hard fingering session makes her moaning but pleasure is bigger while her ass is whipped or penetrated deep in doggy style. Her naughty pussy is spanked, fingered more and excited with a vibrator. In suspension, elegant ropes bondage immobilizes the slave for dominator to eat pussy. Slave's mission is over after a blowjob session and doggie fuck.
Format: mp4
Duration: 22:55
Video: 1900x1080, AVC (H.264), 4052kbps
Audio: 124kbps

File size: 701.8 MB


DOWNLOAD FROM FILESMONSTER: Subspaceland - Home Corporal Punishment II

Subspaceland - Echoes of Punishment Godfrey

Release Year: 2015
Studio: Subspaceland
Cast: Alessandra Jane
Genres: BDSM
Video language: English
Alessandra Jane lacks is discipline...it's easy to lose sight of who you are when you get wrapped up in your own plans...her boyfriend spotted the issues immediately and had her sent to me...I call it humility training...
Format: mp4
Duration: 22:44
Video: 1920x1080, AVC (H.264), 2805kbps
Audio: 155kbps

File size: 493.8 MB


DOWNLOAD FROM FILESMONSTER: Subspaceland - Echoes of Punishment

Desirous Woman Disciplined And Whipped Amidst Rainfall – Section One Malvern

Cast: Steve Holmes ,Juan Lucho ,Nora Barcelona ,Silvia Rubi
Video language: English
Nora’s Been A Naughty Little Bitch - Part 1Nora Barcelona is a sweet, petite Spanish beauty, eager to be put in her slutty place. Silvia Rubi marches her out into a public square and puts her in handcuffs where Nora’s made to perform like a dog. She trots about in the rain, she’s stripped naked, plays fetch, begs for food from strangers, and is ultimately punished with a humiliating public spanking and flogging, all while being photographed and filmed by a steady stream of onlookers.
Naughty Little Bitch Gets Her Bone - Part 2Nora Barcelona is brought to a dive bar, fresh from being humiliated by Silvia Rubi in a rainy public square, and finally gets the bone she’s been begging for. She’s spanked, shocked and paddled in front of a rowdy crowd until her ass is beet-red and white-hot, then she’s handed over to a bar patron and fucked in front of everyone. Once Nora’s been fully humiliated, she’s led outside wearing nothing but shoes, and walks naked through the city streets.
Format: mp4
Duration: 26:51
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps

File size: 294.3 MB


DOWNLOAD FROM FILESMONSTER: Desirous Woman Disciplined And Whipped Amidst Rainfall – Section One

Abella faced repercussions due to errors made by newcomers Cranberry Twp

Cast: Zoe Parker ,Bill Bailey ,Abella Danger
Video language: English
Slutty masochist Abella Danger is a perfect slave, but can she graduate to tutoring another piece of hot slave fuck meat? The Butler finds her misusing the new girl as she cleans the lounge. Zoe has not even been taught the rules, let alone given a task aside from lapping at Abella’s asshole. Cruel metal nipple clamps and weight are applied to Abella to teach her a lesson in humility as Bill ties up the new slave trainee and shows Abella how to properly use a new girl. filling her hot mouth with cock, fucking her tight pussy, and stimulating her clit as she has the rules pounded into her, and electro zapper on hand if she can’t recite them. Abella is given a punishment orgasm, walking backwards to pull the tight metal clamps off her swollen nipples.
Second scene, Zoe is on her own as Abella has her head locked under a table and her ass tied open wide. Zoe must stand and take a deep pounding in her pink cunt while learning to plead for her and Abella’s pleasure with composure. Gracefully begging into Abella’s asshole, Zoes earns them both reward orgasms from the vibrators latched to both their clits with tight rope bondage.
Abella, having done a wonderful job with Zoe, is fed torment and rough anal fucking in bondage for the rest of her service. The look on fresh girl Zoe’s face is priceless and she soothes Abella’s cunt with her tongue and rips clamps on Abella’s insane breast zipper. Both girls get rough reverse cowgirl fucks and a hot cum on their lovely faces for a job well done.
Format: mp4
Duration: 1:02:57
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps

File size: 689.9 MB


DOWNLOAD FROM FILESMONSTER: Abella faced repercussions due to errors made by newcomers

Subspaceland - Deserted Hope Brightwood

Release Year: 2016
Studio: Subspaceland
Cast: Mia Evans
Genres: BDSM
Video language: English
No mercy and no hope in this BDSM session! Skinny slave Mia Evans is so fragile, you can see her ribs, and this is even more interesting... to see if she resists until the end of this harsh torment, because surrender is not her first options. Full body tied, legs apart and tied, hands tied behind and crotch rope bondage, makes her ultra-sensitive and she feels every lash more intense, but this is just the warming up. Caught in pipes in a terrible position the slave must endure a rough pussy punishment: she gets her horny pussy fingered and drilled with a vibrator... her shaved pussy glows, she is so wet and soon you would think the she will gave...
Format: mp4
Duration: 24:27
Video: 1920x1080, AVC (H.264), 3302kbps
Audio: 124kbps

File size: 614.7 MB


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[Bowezab]

Maggie's fun Lake Leelanau

Studio: Notorious Productions
Video language: English
She thought she was having some harmless fun recording herself wacking off, now she's caught and has to be punished...
Format: mp4
Duration: 20:09
Video: 640x480, AVC (H.264), 3905kbps
Audio: 124kbps

File size: 595.0 MB


DOWNLOAD FROM FILESMONSTER: Maggie's fun

Bibi Miami vol.1 Sexual Disgrace Bound For Glory Deerwood

Release Year: 2016
Studio: SexualDisgrace
Cast: Bibi Miami
Genres: Bondage, BDSM
Video language: English
Bibi up for round two and make her focus on the punishing training that lies ahead. Next, master cuts right to the chase and fucks her pretty face like it?s his last day on earth. He spits in Bibi?s face and whips her, and just when you think the humiliation can?t get any worse, he breaks out a jumbo dildo on a stick and what?s left of Bibi?s cum sockets. Bibi digs it all!
Format: mp4
Duration: 15:05
Video: 1280x720, AVC (H.264), 7814kbps
Audio: 106kbps

File size: 874.9 MB


DOWNLOAD FROM FILESMONSTER: Bibi Miami vol.1 Sexual Disgrace Bound For Glory

Hidden Gem Luthersville

Cast: James Deen ,Dana DeArmond ,Skin Diamond
Video language: English
Skin Diamond makes her debut at Everythingbutt as a submissive to Dana DeArmond and James Deen. She gets off from punishment and being told what to do. Her ass gets fucked hard and deep by Dana’s strap-on and James’s cock.
Format: mp4
Duration: 1:19:02
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps

File size: 863.7 MB


DOWNLOAD FROM FILESMONSTER: Hidden Gem

He Hogcuffs part 2 Utting

This clip starts where Part 1 ended... The creepy man removes her punishing cleave gag and replaces it with a large black ball gag. He then toe and thumb cuffs her. He uses more black tape... wrapping it around the ball gag. it deeper into her mouth. He sits back and watches her struggle. After a while he returns to cuff her elbows and then he hogcuffs her. He leaves her to whimper moan and struggle again in the unforgiving steel chain and cuffs. He's not done with her yet though. He clover clamps her nipples and then stands over her with his foot on her side, like a proud hunter standing over his prize trophy game. Poor Violet does not seem to like the clamps at all! He doesn't seem to care though, he seems to delight in her suffering. After a while he pays her some more attention. He finally removes the clamps and then her gag. He kneads and pinches her sore nipples and once again delights in her muffled screams. He removes the cuffs and chains except for her wrists and ankles. Violet seems to be learning her place. She is now calling him "Sir" and is trying to keep quiet as he works. He tells her that he wants to see her bound in rope. He starts by tying a rope around her neck. This is where Part 2 ends.
Format: mp4
Duration: 22:45
Video: 1280x720, AVC (H.264), 2921kbps
Audio: 120kbps

File size: 507.9 MB


DOWNLOAD FROM FILESMONSTER: He Hogcuffs part 2

Breastsinpain Breast Punishment and Orgasm for Slave Sylvie Torre Pellice

Release Year: 2022
Studio: Breastsinpain
Cast: Rubber Slave Sylvie
Genres: BDSM
Video language: English
Rubber Slave Sylvie may be a precious little flower, but there's lots of fight in her...This update features a progressive set...Madison starts out dressed in fetish garb...
Format: mp4
Duration: 27:08
Video: 1920x1080, MP4V, 4883kbps
Audio: 92kbps

File size: 989.9 MB


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Subspaceland - True Emotions Through Tears Pearisburg

Release Year: 2016
Studio: Subspaceland
Cast: Fira Ventura
Genres: BDSM
Video language: English
Newbie in the art of BDSM submission game, slave's babe Fira Ventura punish lesson starts with tickle torment and gets more serious and painful once he begins the whipping and spanking session. Tied up with tight breast bondage and crotch rope, master fires up her ass cheeks, fingers and vibrates her nasty pussy until she screams of pleasure. The ordeal of BDSM submission game is over once she is hardcore deepthroat mouth fuck while pulling hair and cum in mouth to swallow cum.
Format: mp4
Duration: 24:50
Video: 1900x1080, AVC (H.264), 2831kbps
Audio: 124kbps

File size: 538.6 MB


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Coralie Reyes and Blair Weston Washougal

Cast: Nikki Nievez ,Kelly Wells
Video language: English
Kelly Wells has a fantastic body, pretty face and craves to be dominated thoroughly. Nikki Nievez is strict and demands hard punishment before rewarding her slaves. This session has rough sexual play and an intense anal scene with a giant acrylic plug!
Format: mp4
Duration: 38:12
Video: 960x540, AVC (H.264), 1366kbps
Audio: 121kbps

File size: 417.3 MB


DOWNLOAD FROM FILESMONSTER: Coralie Reyes and Blair Weston

[Bowezab]

The Event: Forgive Me, Dad, My Transgressions Are Countless Orlean

Cast: James Deen ,Evi Fox ,Kiki Vidis
Video language: English
Two trouble making girls are too much for Sister Pink to handle. After being ridiculed and disgraced, the Sister goes to Father Deen for assistance. His unorthodox approach to discipline is very effective in turning these girls into apologetic fuck sluts. Watch two brand new hot girls, Evi Fox and Kiki Vidis take punishment in the form of rough sex, bondage, degradation and corporal punishment!
Format: mp4
Duration: 1:17:58
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps

File size: 851.9 MB


DOWNLOAD FROM FILESMONSTER: The Event: Forgive Me, Dad, My Transgressions Are Countless

[Bowezab]

Subspaceland - A BDSM Lesson of Terror Okemah

Release Year: 2014
Studio: Subspaceland
Cast: Alessandra Jane
Genres: BDSM
Video language: English
He gets right to work using bondage, punishment and sexual dominance and Alessandra Jane responds very well...
Format: mp4
Duration: 22:19
Video: 1280x720, AVC (H.264), 1759kbps
Audio: 156kbps

File size: 314.1 MB


DOWNLOAD FROM FILESMONSTER: Subspaceland - A BDSM Lesson of Terror

Breastsinpain Tit Punishment for Bettine in the new White Room Port Royal

Release Year: 2020
Studio: Breastsinpain
Cast: Bettine
Genres: BDSM
Video language: English
Bettine's got one hell of a crazy body and she's not shy about showing it...She simply oozes sex and listening to her moan as she disrobes, is arousin g...to say the least...
Format: Windows Media
Duration: 14:32
Video: 1280x720, Windows Media Video 9, 2929kbps
Audio: 125kbps

File size: 326.3 MB


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Breastsinpain Archives – Tit Punishment for Bustyteen continues Fritch

Release Year: 2020
Studio: Breastsinpain
Cast: Bustyteen
Genres: BDSM
Video language: English
And then, she sits back and masturbates for us. We then bind her arms and legs tightly and Bustyteen , despite her obvious strength, is certainly no match for these ties...
Format: Windows Media
Duration: 28:48
Video: 1280x720, Windows Media Video 9, 2929kbps
Audio: 125kbps

File size: 647.6 MB


DOWNLOAD FROM FILESMONSTER: Breastsinpain Archives – Tit Punishment for Bustyteen continues

Raw Flesh: Repeatedly Embraced Within Restrictive Ties Glenham

Cast: Tommy Pistol ,Aften Opal
Video language: English
Aften is young, fit, and more than willing to be bound and fucked by Tommy Pistol. We begin with Aften bound to a wooden chair with tight rope bondage around her writs and ankles. Tommy enters and begins to explore her flesh, as well as her holes. He inflicts some pain with his hands before pushing her head down on his cock and making her swallow all of it. He goes back and forth between fucking her face and holding the vibe on her pussy, until she is completely wrecked. Next, Aften experiences her first ever rope suspension with her hands and feet pulled up and out of Tommy’s way. He begins by priming her pussy with the vibe again and squeezing out more orgasms. Now that this slut is ready, Tommy begins to inflict more punishment with a leather paddle on her ass and pussy. It’s time for fucking, so he buries his cock balls deep in her wet pussy. As he fucks her he continues to torment her with more hating and torment. Orgasms pour out of her pussy as she is used like a piece of meat. In the final scene, Tommy has Aften in a ball tie and helpless on the bed. He positions her in a way to service his cock before fucking her more. Once the fucking begins, he is on a mission to overwhelm her with non stop orgasms until he covers her ass with his big load of cum.
Format: mp4
Duration: 1:07:56
Video: 1920x1080, AVC (H.264), 9755kbps
Audio: 156kbps

File size: 4.8 GB


DOWNLOAD FROM FILESMONSTER: Raw Flesh: Repeatedly Embraced Within Restrictive Ties

Camille Angel - Big Boobs Of My Stepdaughter (2025) Plevna

Release Year: 2025
Cast: Camille Angel
Genres: Old and Young
Video language: English
Camille’s stepdaddy, Julian, wants her to tidy her room. If she doesn’t do it within an hour, she’ll face a consequence. The idea of ​​being punished by Julian excites Camille, and she decides to defy him by being a baaaad girl!
Format: mp4
Duration: 27:31
Video: 1920x1080, AVC (H.264), 7323kbps
Audio: 122kbps

File size: 1.5 GB


DOWNLOAD FROM FILESMONSTER: Camille Angel - Big Boobs Of My Stepdaughter (2025)

Return of the Panty Sniffing Perverts Prairieburg

Release Year: 2021
Genres: BDSM, Bondage, Tits Torture
Video language: English
To tell the truth she wasn't done with us, either. You see, she isn't some captive piece of ass that we're keeping locked in a dungeon. She is here of her own free will. She came looking for intense bondage and corporal punishment. We brought more than one Dom along because we've seen Bella, and dozens of other girls just like her, before. The seductive smile and coy flirting are all there to entice you in under the guise of showing her a thing or two, but Bella knows exactly what she's doing, exactly what she wants, and she is insatiable.
Format: mp4
Duration: 34:11
Video: 1280x720, AVC (H.264), 6770kbps
Audio: 101kbps

File size: 1.7 GB


DOWNLOAD FROM FILESMONSTER: Return of the Panty Sniffing Perverts

IR - Bonnie Day - Chatter Bitch Part 1 Whitelaw

Release Year: 2014
Cast: Bonnie Day
Genres: BDSM, Extreme Bondage, Domination, Fetish, Spanking, Humiliation
Video language: English
Bonnie Day Has Her Behavior Modified.
Man, Bonnie Day can be one obnoxious ass bitch around the office. She's constantly getting in the way of everyone else getting their work done. Well, OT needs his business running like a well oiled machine, and if she is going to get in the way of that then she is going to have to be taught a lesson in proper office performance.
Here at Intersec we have a... unique view on how to punish our employees. We don't like to just fire people if we know there is a way they can be reformed. Sometimes they just need a little bit of incentive to behave themselves properly.
In this case the punishment is corporal and it comes along with some intense heavy metal bondage. It's the only way we can be sure that she's going to learn not to bother the rest of the staff when they are working. We need to be able to depend on her to do what she is told, nothing more and certainly nothing less. And if that means taking a few days out of her work week to bring her down to the dungeon and show her what the price of disobedience is, then OT is more than happy to do it. If Bonnie doesn't like it she's free to quit. You know... as soon as we unlock her.
Format: mp4
Duration: 39:06
Video: 1280x720, AVC (H.264), 7284kbps
Audio: 111kbps

File size: 2.1 GB


DOWNLOAD FROM FILESMONSTER: IR - Bonnie Day - Chatter Bitch Part 1

[Bowezab]

Subspaceland - Chains Of Obedience Hagerstown

Release Year: 2016
Studio: Subspaceland
Cast: Alessandra Jane
Genres: BDSM
Video language: English
Sweet teen Alessandra Jane is about to be punished and fucked in hot BDSM sex session! She is so young and always horny and she really needs to be tempered a bit. Hands tied up and wearing sexy black lingerie, slave got tickled for the beginning, then her Master ties her leg with rope and fully exposed all her body. Blonde slave gets her clit rubbed and her pink pussy fingered and must endure severe whipping treatment. Strapped down and spread legs open for pussy stimulated with vibrator, the slave feels exhausted in the intense experiences of both pain and pleasure. Tied to bed, the tormenting continues with an extreme sex session and beautiful slave gets mercilessly fucked by her...
Format: mp4
Duration: 22:16
Video: 1920x1080, AVC (H.264), 3597kbps
Audio: 184kbps

File size: 617.7 MB


DOWNLOAD FROM FILESMONSTER: Subspaceland - Chains Of Obedience

Rhys Sterling and Juniper Bellweather Dahlonega

Cast: Stacey Cash ,Elliot Skellington
Video language: English
‘Do you know why your mouth is gagged? No? Because it is only good for eating my pussy and licking my ass. Now, LICK’, she commands with a cruel tug on the rope leashed around his balls. The black latex spreads tightly across her taught flesh, and his tongue laps eagerly at her perfect ass.
Stacey Cash looks amazing wielding a whip, dressed in black latex, dishing out the punishment before violently fucking her slaveboy in the ass with her hard strap-on.
Format: mp4
Duration: 41:39
Video: 640x480, AVC (H.264), 1171kbps
Audio: 122kbps

File size: 395.6 MB


DOWNLOAD FROM FILESMONSTER: Rhys Sterling and Juniper Bellweather

Lola vs. A Little Roleplay El Penon

As I was tying Lola up she mentioned she wanted to try a little roleplay sometime. While she was likely fantasizing about being a naughty girl and a light spanking, I had other plans. Bound in a strappado with her mouth stuffed and taped shut, Lola was curious about where this was going. After accusing her of stealing money on the counter, the actuator connected to her strappado lifted bringing her to her toes. Struggling to keep the pressure off her arms, it’s made clear she’ll only get a break after she admits her crime. Lola tries her best but eventually gives in. What she doesn’t know is her actual punishment is yet to come!
Format: mp4
Duration: 13:44
Video: 1280x720, AVC (H.264), 2449kbps
Audio: 310kbps

File size: 277.8 MB


DOWNLOAD FROM FILESMONSTER: Lola vs. A Little Roleplay

Sheena Rose's Smart Mouth Gets Punished Osmond

Release Year: 2023
Studio: SexualDisgrace
Cast: Sheena Rose
Genres: Bondage, BDSM
Video language: English
I get scared sometimes he might do something more than he does, something I really can't handle. That's why I shut up but tempted to talk back again. I think he likes it. He gives me a huge steamy load of his sweet man juice every time I rile him up and take his punishing cock. I know I please my Master.
Format: mp4
Duration: 24:09
Video: 1920x1080, AVC (H.264), 2993kbps
Audio: 107kbps

File size: 549.2 MB


DOWNLOAD FROM FILESMONSTER: Sheena Rose's Smart Mouth Gets Punished

Breastsinpain More hard Tit Punishment for Bettine Barneston

Release Year: 2020
Studio: Breastsinpain
Cast: Bettine
Genres: BDSM
Video language: English
She's a fan fa vorite and it's easy to see why, and we expand upon that by asking her to strip and show our members all that she's got.
Format: Windows Media
Duration: 15:47
Video: 1280x720, Windows Media Video 9, 2929kbps
Audio: 125kbps

File size: 354.1 MB


DOWNLOAD FROM FILESMONSTER: Breastsinpain More hard Tit Punishment for Bettine

Subspaceland - Burning Haley Monteria

Release Year: 2016
Studio: Subspaceland
Cast: Haley Hill
Genres: BDSM
Video language: English
Dark secrets are kept in the attic and revealed only for the real fans of fascinating bdsm world! Enjoy hot submission of Serbian blonde teen Haley Hill and watch her totally surrender to her cruel dominant! Wearing sexy leather lingerie, she lets her fresh body at her Master's disposal and gets strongly aroused by tickling and whipping session. Haley moans in pain and humiliation as she pushes her ass higher in the special bondage chair designed extremely for a real pussy punishment. Tied up tight she gets her cunt dildo fucked without mercy, and even with the ball gag in her mouth you can tell how much she likes it! Next is a hot wax play: Master is dripping hot...
Format: mp4
Duration: 23:52
Video: 1920x1080, AVC (H.264), 3228kbps
Audio: 184kbps

File size: 597.6 MB


DOWNLOAD FROM FILESMONSTER: Subspaceland - Burning Haley

Brooklyn Lee's Discipline with Spanking West Burlington

Cast: Brooklyn Lee ,Isis Love ,Mark Wood
Video language: English
Brooklyn Lee clearly gets off on rough sex and punishment. Isis Love works this hot slut over with anal toys and kinky girl on girl action. Then she gets intense and emotional hard anal sex with Isis Love and Mark Wood teaming up to give this sexy pain slut what she deserves!
Format: mp4
Duration: 1:11:03
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps

File size: 776.4 MB


DOWNLOAD FROM FILESMONSTER: Brooklyn Lee's Discipline with Spanking

[Bowezab]

Bashful Riley Willis

Cast: Lorelei Lee ,Riley Shy
Video language: English
Lorelei Lee makes her Dom debut on WiredPussy as she electrifies and sexually teases her slave, Riley Shy. The chemistry between these two hot girls is undeniable - even in the pre-interview there is a glint in Riley’s deep blue eyes. She admits that her greatest pleasure is being a good girl for her Mistress even though she is scared of the electricity. Lorelei ravages Riley bringing her close to orgasm and then denying her little sub, until the last scene of the day. Instead of orgasms Riley is punished with voice activated stims, electrified nipple clamps and an electrified copper dildo stuffed deep into her cunt with the magic wand just out of her reach. Lorelei works her submissive into such an aroused state that by the end of the shoot, Riley is begging for the electricity to be turned up while she cums hard after waiting for it all day long.
Format: mp4
Duration: 47:26
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps

File size: 518.3 MB


DOWNLOAD FROM FILESMONSTER: Bashful Riley

Concluding Assessment Waiblingen

Cast: Steve Holmes ,Tricia Oaks
Video language: English
Out of desperation, Tricia Oaks takes a final exam that tests her endurance and determination. She is punished and fucked in the professors office. For the second part of her test, Tricia goes to his house at night, puts herself in bondage and gets fucked in the ass.
Format: mp4
Duration: 58:06
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps

File size: 634.8 MB


DOWNLOAD FROM FILESMONSTER: Concluding Assessment

Cane Rain Dronninglund

Release Year: 2024
Genres: BDSM, Bondage, Humilation,Tits torture
Video language: English
I laid my canes next to Rain Degrey so she would know what was coming. Her hands, feet and ass are all exposed to the impending punishment and she's terrified. When she has had enough I will move her into a new position and start working on fresher flesh.
Format: mp4
Duration: 37:31
Video: 1280x720, AVC (H.264), 2687kbps
Audio: 118kbps

File size: 806.0 MB


DOWNLOAD FROM FILESMONSTER: Cane Rain

IR - Bonnie Day - Chatter Bitch Part 2 Glenmoore

Release Year: 2015
Cast: Bonnie Day
Genres: BDSM, Bondage, Humiliation, Squirting, Toys, Ass Caning, Face Bondage, Hogtie
Video language: English
Bonnie Day was given one job. After disrupting the office yesterday OT removed her, showed her the price of her poor performance, and brought her back to the office. She was tired, humiliated, locked in bondage and gagged still, but all she had to do was finish a single edit and he would let her out and things would go back to normal. She closed her eyes for “just a minute” so that she could think more clearly after a nap.
When OT woke her up the next morning the fear in her eyes was obvious. It looks like she needs another day to think about how much she needs this job. Being a good worker and a good submissive are very alike. They must learn to take instruction well, accomplish tasks that are assigned and accept punishment for their failures.
Sometimes we'll suspend a girl in the air to add to their feeling of helplessness. OT is caning Bonnie so hard that she literally uses her bondage to pull herself up off of the ground. That's how you know it is effective.
Format: mp4
Duration: 40:35
Video: 1280x720, AVC (H.264), 7284kbps
Audio: 111kbps

File size: 2.1 GB


DOWNLOAD FROM FILESMONSTER: IR - Bonnie Day - Chatter Bitch Part 2

Madam Heart and Sharp Shooter Bill South Wellfleet

Cast: Mistress Heart ,Wild Bill
Video language: English
Mistress Heart comes to MenInPain with her own sense of style and domination. Partnered with the mischievous Wild Bill she takes her time teaching him not to top from the bottom and adminstering some harsh punishment. As always Bill’s hard on doesn’t disappoint so he is tied to the chair and made to be a puppet with tight ropes around his cock and balls! This is a BONUS update, enjoy!!!
Format: mp4
Duration: 23:40
Video: 640x480, AVC (H.264), 1171kbps
Audio: 122kbps

File size: 224.8 MB


DOWNLOAD FROM FILESMONSTER: Madam Heart and Sharp Shooter Bill

Mena Li is Brought Back for More Use and Orgasms Marland

Release Year: 2015
Studio: SexualDisgrace
Cast: Mena Li
Genres: Bondage, BDSM
Video language: English
This session I woke up on a bare bed, ropes hugging my breasts, more rope keeping my wrists together behind my back, my legs free for easy maneuvering. I tried to getaway but he knows how to keep me bound in place for whatever he desires. No matter how much I screamed, he pushes me down, slaps me around and punishes me with his throbbing cock, making me beg for it. The only times I was still is when I was servicing his dick, my head in his hands making me take it deep down my throat. He threw me all around the bed to do so with such ease. I must admit. I love being manhandled, covered in spit and pussy and mouth sore from so much cock. He fucked my doggy, on my side, missionary, all perfect for taking cock deep, fast and rough. He's relentless. No matter how many times I cum, he keeps going, wrecking my pussy even more. After all this work, I just wanted his thick creamy warm load. I feel this slutty sex slave earned it.
Format: mp4
Duration: 29:19
Video: 1920x1080, AVC (H.264), 2840kbps
Audio: 100kbps

File size: 632.8 MB


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Dillion Carter Proves to be a Cock Hungry Sex Slave Gabriola

Release Year: 2015
Studio: SexualDisgrace
Cast: Dillion Carter
Genres: Bondage, BDSM
Video language: English
The more I moan, the rougher he gets with me. I get scared sometimes he might do something more than he does, something I really can't handle. That's why I shut up but tempted to talk back again. I think he likes it. He gives me a huge steamy load of his sweet man juice every time I rile him up and take his punishing cock. I know I please my Master.
Format: mp4
Duration: 21:40
Video: 1920x1080, AVC (H.264), 2972kbps
Audio: 102kbps

File size: 488.7 MB


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[Bowezab]

Subspaceland - A Well Deserved Punishment Darlag

Release Year: 2016
Studio: Subspaceland
Cast: Anina Silk
Genres: BDSM
Video language: English
Hard times for bad slave Anina Silk. Master teaches her what a disobedient slut deserves giving her the well-deserved BDSM rough treatment. Tormented with rope bondage, hard slapped, and orgasm denied this slave learns by hard domination the way to be a good submissive
Format: mp4
Duration: 16:53
Video: 1900x1080, AVC (H.264), 4264kbps
Audio: 124kbps

File size: 543.3 MB


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Breastsinpain Breast Punishment for sexy Slave Dana Reseda

Release Year: 2022
Studio: Breastsinpain
Cast: Slave Dana
Genres: BDSM
Video language: English
Trashy or sophisticated...in my mind I can clearly see her both ways, but nothing in between...and I dont care which way she does go, I'll lust for her just the same...
Format: Windows Media
Duration: 8:16
Video: 1920x1080, Windows Media Video 9, 4882kbps
Audio: 125kbps

File size: 305.4 MB


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Brunette Cindy Likes To Play With This Pretty Girl Yako

Release Year: 2014
Cast: Madlin And Cindy Hope
Genres: Bondage, Fetish, BDSM, Wax, Anal, Toys, Lesbian
Video language: English
Mistress Cindy Hope has slavegirl Madlin to play with. While she reads a magazine, the Hungarian goddess keeps her naked submissive standing and leashed next to the couch...
Then Cindy decides to have fun with her subbie. She tugs her down by her leash and gets Madlin eating her out in this fetish Hot video. She has Madlin well-trained to lap deep at her dominant quim...
But Madlin’s duties are not only sexual. The Hungarian slavegirl fetches refreshments for her mistress, but then the domme cruelly trips her...
For such clumsiness, punishment is required in the form of a harsh spanking on Madlin’s naked bottom. In fact, determined to really redden that butt, Mistress Cindy puts Madlin over her knee to unforgettably warm those cheeks.
Then, for her further amusement, Mistress Cindy chains Madlin to the coffee table for some lesbian bondage and pours red candle wax all over the helpless girl’s nude body and shaved pussy! Madlin writhes and gasps in agony as her naked skin is littered with the sizzling wax.
But there’s even more - as inventive Mistress Cindy sits on her slave’s face and then takes out a black dildo for further humiliations and penetrations in this epic of Full HD Bdsm!
Format: mp4
Duration: 37:55
Video: 1920x1080, AVC (H.264), 7810kbps
Audio: 184kbps

File size: 2.2 GB


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Deceitful, unfaithful hussy Romeo

Cast: Mark Davis ,Savannah West
Video language: English
Adorable Savannah West is caught cheating on a test and gets punished and fucked in this incredibly sexy fantasy role play with Mark Davis. This is Savannah’s first time getting fucked in bondage and she absolutely loves every minute of it.
Format: mp4
Duration: 51:53
Video: 960x540, AVC (H.264), 1364kbps
Audio: 122kbps

File size: 566.3 MB


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MistressAE - Clip 32 Robersonville

Studio: MistressAe
Genres: Femdom
Who remembers the cigarillo from the second part? Missed it? Actually, you always watch all the parts of a series here. That screams punishment.
Format: mp4
Duration: 18:59
Video: 1920x1080, AVC (H.264), 3188kbps
Audio: 127kbps

File size: 459.9 MB


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Naima New Maryland

Cast: Steven St. Croix ,Naomi
Video language: English
Naomi is a well known performer in the adult industry. She enjoys doing the occasional rough sex scene because she’s “made to put more energy into the scene.” This is her first BDSM scene and as you will see she really gets off and enjoys the experience immensely. Steven St. Croix makes her suffer and surrender to punishment, blowjobs and anal sex while her hard, fit body is bound. This is a very passionate scene!
Format: mp4
Duration: 53:13
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps

File size: 581.4 MB


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My sweet bbw Mullingar

Release Year: 2025
Cast: girl
Genres: Bbw, Dp, Oral, Facial, Anal, Blowjobs, ThroatFuck, Vomit, Humiliation, Pissing
Video language: English
She was turned out hard and rough. Fastidiously fucked, and vi.ated like a vassal state under the malevolent hand of Mao--she learned a lot about herself, and was proffered a notion about her place upon the pasture with a plethora of punishments and perversions that would make any pudgy piglet polemically pale with pedantic precariousness. She hated the Yellow Discipline. It made her cry, but she deserved it, and as she sat there in her own filth, whilst taking 3 nuts to her sexy face, and a dog bowl full of abominations upon her head, she was taught the simple facts of patriarchal power and predominance.
Format: mp4
Duration: 57:20
Video: 1920x1080, AVC (H.264), 7755kbps
Audio: 300kbps

File size: 3.3 GB


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[Bowezab]

Question closely Orrick

Cast: Mark Davis ,Sara Faye
Video language: English
If you’re not into the LA pornstar look, Sara Faye is the girl for you. She is a pretty natural looking girl who gets turned on by kinky sex. In this role play scene, she gets interrogated by Mark Davis in a dark holding cell. He tries to get her to speak through punishment, humiliation and sex while bound. Will she finally give in after being fucked and her mouth filled with her tormentors cum?
Format: mp4
Duration: 44:35
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps

File size: 487.3 MB


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[Bowezab]

Breastsinpain Archives – Breast Punishment Lesson for Rubber Slave Sylvie West Frankfort

Release Year: 2021
Studio: Breastsinpain
Cast: Rubber Slave Sylvie
Genres: BDSM
Video language: English
So we tie Rubber Slave Sylvie up and strip her down, just like all the other models...then we sit with her clit on top of the sybian...and then we make cum...obviously, at the very least, is a switch and hot as hell...
Format: Windows Media
Duration: 26:57
Video: 1280x720, Windows Media Video 9, 2929kbps
Audio: 62kbps

File size: 593.6 MB


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Naughty Hotties In A Musical Studio Schifferstadt

Release Year: 2013
Cast: Cindy Behr, Harvey Jay, Christine Love, Jasmine Black, Rebecca Ryder, Britney, Amanda Black, Black Angelica, Tarra White, Farrah Fox
Genres: Pornstars, Group Sex, Big Tits, European, DvP, Lingerie
Video language: English
10 Hot girls just waiting to be in the music industry. Watch them all try to get there! Radio host Ben Dover is shooting a webcam podcast in his studio and invites a couple of guests to his show. Amanda is an up and coming singer from Romania and is promoting her new album in Bender's studio.
She gives a little strip tease for the webcam viewers and wants to demonstrate the host and the producer what other talents she possesses. Two nuns, Jasmine and Tarra, are looking for Ben Dover to assist them with a special request they have but instead they find two other colleagues that are willing to help Jasmine and Tarra with their needs.
Girl duo Angelica and Britney have a new record and are at Ben's show to do some promoting. But instead of promoting their album, Angelica and Britney decide to have some hot, wet fun with their mouths. Christine is looking for some assistance from Ben for charity.
Ben would love to help but needs some convincing and Christine is willing to do anything for Charity, even if it means being DP'd! Harvey and Rebecca are the admin girls at Bluebird Radio and recently have not been performing their task correctly, so Ben decides to punish them the only way he can think of.
Cindy and Farrah are in a punk band making their way to Bluebird studio so that Ben can play their new record on the radio but Ben needs some convincing before he helps these girls.
Format: avi
Duration: 2:46:26
Video: 854x480, AVC (H.264), 1600kbps
Audio: 124kbps

File size: 2.1 GB


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[Small Talk] Sklavenschule Scene #2 Brinkhaven

Release Year: 2006
Studio: Small Talk
Genres: BDSM, Male Dom, Fem Dom, Cock Torture
Video language: German
These hot dominating whores love fucking their captives and victims as much as they love administering the punishment. Some do it right in a kitchen or
in a living room using spoons as well as special punishment tools and riding crops to get their men ready for fuck. Others take it to a special BDSM
chamber using spanking and walk as a kinky sexual foreplay before having submissive cuties suck cock and punishing their little wet pussy holes.
Format: lavfpref
Duration: 16:50
Video: 720x576, AVC (H.264), 3808kbps
Audio: 124kbps

File size: 485.5 MB


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Breastsinpain Breathplay and Tiny Tits Punishment for Rija Mae Rawlings

Release Year: 2021
Studio: Breastsinpain
Cast: Rija Mae
Genres: BDSM
Video language: English
The start of a new series with she. Rija Mae and I did a few shoots towards the end of 2019 and then lost touch. We recently met up again and decided to shoot.
Format: Windows Media
Duration: 12:35
Video: 1280x720, Windows Media Video 9, 3906kbps
Audio: 125kbps

File size: 373.3 MB


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Introducing Housebreaking for Daisy, Initial Session Winkler

Cast: Daisy Ducati
Video language: English
I am impressed that Daisy Ducati comes to Training of O with clear goals in mind: 1.) To get over her fear of the cattle prod, 2.) to conquer her fear of the single tail, and 3.) to learn to take cock in the ass. The first thing to do is to establish a baseline. I tell her to strip and zap herself with the cattle prod. She is visibly terrified. I smile. This is going to be fun.
On to other assessments, I suspend her and pull her cunt wide open. Let’s see how this girl gets off and how intense she can take it. When I tell her to fuck the dildo stand cowgirl style she thinks it’s going to be easy, but little does she know that this device has destroyed the strongest sluts in the business.
I strap her to the pile driver stand and tie her asshole open. The vibe is tied tight to her cunt and the ass stretching begins. I work her asshole slowly. It is tight. She has never been fucked in the ass by a real cock, and I am intent on making sure she does it well for me before this week is over. She will become my little ass slut.
I drive her over the edge physically and mentally, always extracting rules, refining goals and motivation, always testing her, quick to judge, quick to punish her. The first day is hard for Miss Daisy. Very hard.
Format: mp4
Duration: 1:06:51
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps

File size: 730.8 MB


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Subspaceland - Punished Innocence Minto

Release Year: 2014
Studio: Subspaceland
Cast: Minnie Manga
Genres: BDSM
Video language: English
The jig is up for Minnie Manga as her sleazy landlord has caught her engaging in a little self-inflicted kink. He doesn't take lightly to her dirty ways and has a little punishment on tap for her. Once he's bound her he begins to toy with her mercilessly..
Format: mp4
Duration: 21:24
Video: 1280x720, AVC (H.264), 1221kbps
Audio: 156kbps

File size: 216.8 MB


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Roxy - Partners Punishment (2025) American Fork

Release Year: 2025
Cast: Roxy
Genres: Extreme
Video language: English
21yo Roxy returned more prepared for her second shoot. She held it together despite getting throatfucked balls deep and fucked in the ass mercilessly.
Format: mp4
Duration: 40:54
Video: 1920x1080, AVC (H.264), 15362kbps
Audio: 372kbps

File size: 4.6 GB


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[Bowezab]

The Squash Affair Bell City

Cast: Maitresse Madeline Marlowe ,Mason
Video language: English
Mason’s an embarrassed waitress who goes to the doctor to remove a zucchini stuck up her ass. Doctor Madeline punishes and fucks her with a strapon for being a slut. Mason then takes the doctors fist up her dripping wet cunts and erupts with intense orgasms!
Format: mp4
Duration: 1:01:45
Video: 960x540, AVC (H.264), 1365kbps
Audio: 122kbps

File size: 674.0 MB


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Susane getting bound mouth-stuffed tapegagged Lizton

Release Year: 2017
Studio: Submissed
Cast: Susane
Genres: BDSM, Big boobs, Fetish, Gagged, High heels, Spanking, Stripper, Submission, Tit play
Video language: English
For every thing she does correctly there is a heavenly reward. However when she gets it wrong the punishment is nasty.
Format: mp4
Duration: 8:10
Video: 1280x720, AVC (H.264), 6805kbps
Audio: 184kbps

File size: 418.4 MB


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Breastsinpain Archives – More Breast Punishment for Melanie from MasterT Heilwood

Release Year: 2021
Studio: Breastsinpain
Cast: Melanie
Genres: BDSM
Video language: English
After selling off the other trespasser, I need to keep Melanie restrained while teaching her a lesson at the same time.
Format: Windows Media
Duration: 31:43
Video: 1280x720, Windows Media Video 9, 3906kbps
Audio: 125kbps

File size: 941.3 MB


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Breastsinpain Outdoor Breast Punishment for spanish Girl Lilith K Tall Timbers

Release Year: 2021
Studio: Breastsinpain
Cast: Lilith K
Genres: BDSM
Video language: English
Even though emily received much attention the previous day, I am not going to leave her out of the fun, so I bind her tits with tape and whip hers as well.
Format: Windows Media
Duration: 28:19
Video: 1280x720, Windows Media Video 9, 3906kbps
Audio: 125kbps

File size: 840.3 MB


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Breastsinpain Archives – More Breast Punishment for Katharina from MasterT Huffman

Release Year: 2021
Studio: Breastsinpain
Cast: Katharina
Genres: BDSM
Video language: English
All the models that we shoot are good lookin women...and it's hard to estimate who is better lookin than who...and that's not my interest anyway....
Format: Windows Media
Duration: 28:52
Video: 1280x720, Windows Media Video 9, 1953kbps
Audio: 125kbps

File size: 442.0 MB


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Remote-control pain Pinsonfork

Release Year: 2021
Cast: Louise Von Salome
Genres: BDSM, Big boobs, Brunette, Curvy, Shaved, Spanking, Submission
Video language: English
You will find pictures and videos of needle pain, play peircings, severe breast pain, whipping punishments.
Format: mp4
Duration: 47:42
Video: 1280x720, AVC (H.264), 7776kbps
Audio: 309kbps

File size: 2.8 GB


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Subspaceland - Roughly Punished Newport Beach

Release Year: 2014
Studio: Subspaceland
Cast: Chelsy Sun
Genres: BDSM
Video language: English
This week we bring back Chelsy Sun, definitely a crowd pleaser for sure. Diana's a brunette beauty and we love her. She takes a good hard machine fuck.
Format: mp4
Duration: 22:03
Video: 1280x720, AVC (H.264), 889kbps
Audio: 156kbps

File size: 169.7 MB


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