Punishment painfully porn Videos

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Featuring Chastity Lynn in her First Released Gangbang South Wayne

Cast: Chastity Lynn ,James Deen
Genres: Slapping ,Fisting ,Interracial ,Rough Sex ,Double Penetration ,Gangbang ,Noose ,Fetish ,Blonde ,Choking ,Corporal Punishment ,Chastity Play ,Blowjob
Video language: English
Porn starlet Chastity Lynn explores her fantasy of being tied up, taken down, and fucked hard by a group of ruthless hillbillies! This is her first released gangbang and you DO NOT WANT TO MISS IT!
Bobby and Cheryl take a day trip up into LA’s Tujunga canyon, where on an isolated dirt road a blow job turns into a public disgrace when two local rednecks catch our young lovers in the act! Their troubles continue when they try to leave and discover their car is out of gas. Cheryl stays in the car while Bobby must walk back to the highway to get gas.
Cheryl can’t do anything but sit and wait, thinking about those crude hillbillies in the truck. They got a real kick out of watching her suck her boyfriend’s cock. They could come back at anytime and in this remote, isolated canyon, anything can happen. Who knows what they would want? Who knows what they would demand from her? She would be helpless to resist.
Format: mp4
Duration: 1:11:51
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 785.5 MB


DOWNLOAD FROM FILESMONSTER: Featuring Chastity Lynn in her First Released Gangbang

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Assylum - Painal Yoga Perrysburg

Release Year: 2016
Studio: Assylum
Cast: Rain Summers
Genres: Ass fucking, Ass to mouth, Cum farting, Cum swallow, Cumfart eating, Facial, Foot licking, Gaping, Nasty cum play, Painal, Rough oral, Spitting, Crying, Nasty filth, Pain, Punishment
Video language: English
Real painful anal hatesex and hard face fucking -- that´s what this case file is about. Dr. Mercies already treated her with some slop yoga, so now Orderly Damian treats her with some painal yoga. This is 45 minutes of nonstop extreme ass fucking with Damian´s big cock. Poor Summer cries and screams, but it´s all for the sake of her therapy. In the end, she eats a bowl of spit and cum out of her gaping asshole. Then Dr. Mercies comes back and shoots another load all over her face.
Format: mp4
Duration: 47:59
Video: 1280x720, AVC (H.264), 2408kbps
Audio: 124kbps



File size: 893.1 MB


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Assylum - Punished Punk vol.2 Fort Laramie

Release Year: 2016
Studio: Assylum
Cast: Amelia Dire
Genres: Ass fucking, Ass to mouth, Asslicking, Cum swallow, Facial, Nasty cum play, Painal, Rough oral, Spitting, Bondage, Breast pain, Crying, Face slapping, Pain, Punishment, Pussy pain
Video language: English
20 year-old Amelia gets anally hatefucked, head-fucked, face-fucked, and treated at level 10 by Dr. Mercies in this extreme update. She cries from the spanking, cries from the twisted mind-fuckery, and cries from the giant stick rammed up her ass while she plays punk guitar in the air for the staff´s enterpainment. This scene is as hard, fucked-up, and REAL as it gets. You will not find anal BDSM with this level of authentic intensity anywhere else on the digital planet. Let´s hope Amelia relapses, because treating her was a doctor´s sadistic dream.
Format: mp4
Duration: 52:36
Video: 1280x720, AVC (H.264), 2275kbps
Audio: 125kbps



File size: 928.2 MB


DOWNLOAD FROM FILESMONSTER: Assylum - Punished Punk vol.2

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Assylum - 40,000 Years of Anal Tears North Hollywood

Release Year: 2018
Studio: Assylum
Cast: Jessica Kay
Genres: Ass fucking, Asshole pain, Asslicking, Face fucking, Facial, Foot licking, Painal, Rimjobs, Rough anal , Rough oral, Spitting, Bondage, Breast pain, Breast slapping, Face slapping, gagging, Mind fucking, Paddling, Pain, Pussy pain, Screaming, Suspension, W
Video language: English
Beautiful, submissive sweetheart Jessica Kay is back for another sick and twisted epic. And of course, she´s brought her plump, hot ass back with her. This time, Dr. Mercies is in good spirits, because life´s been treating him well. But he wonders what it would be like to be an anal BDSM pervert in other times and places. So he takes Jessica on a crazy painal domination journey across 40,000 years. This session is surreal but also real. It includes painful anal fucking in a straightjacket, cave woman beating, witch dunking, and severe ass punishment in the scold´s bridle.
Format: mp4
Duration: 1:22:56
Video: 1280x720, AVC (H.264), 1780kbps
Audio: 122kbps



File size: 1.1 GB


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Assylum - Ass-to-mouth meat vol.1 Englishtown

Release Year: 2015
Studio: Assylum
Cast: Caramel Starr
Genres: Ass fucking, Ass to mouth, Asslicking, Facial, Rough oral, Spitting, Bondage, Punishment, Black girls, Two guys
Video language: English
Caramel likes ass to mouth, so we made her into a piece of ass-to-mouth meat. Orderly Patrick and Dr. Mercies did a very long session with various dildos and anal beads on her, and then the orderly pounded her ass. After that, Dr. Mercies made her eat his ass 100 times as he slapped her face and verbally degraded her. In part 2, she gets assfucked some more, then hung upside down with some sausages and anally tenderized.
Format: mp4
Duration: 48:08
Video: 1280x720, AVC (H.264), 2415kbps
Audio: 124kbps



File size: 898.6 MB


DOWNLOAD FROM FILESMONSTER: Assylum - Ass-to-mouth meat vol.1

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Assylum - Painal Doll Glen Arbor

Release Year: 2017
Studio: Assylum
Cast: Patient Kat Monroe
Genres: Ass fucking, Ass to mouth, Asshole pain, Asslicking, Cum in eye, Cum swallow, Facial, Nasty cum play, Painal, Pussy fucking, Rough oral, Spitting, Bondage, Face slapping, gagging, Pain, Punishment, Pussy pain, Suspension, Big ass, Brunette, Pornstar
Video language: English
Kat Monroe is a hot girl with a big, juicy ass and the spirit of a tough wench from bygone times. She´s the kind of girl you want to destroy and respect at the same time. This inspired Dr. Mercies, and he went to town on all her holes. He dressed her up like a voodoo doll and stabbed her mouth, ass, and pussy hundreds of times with long dildos and his cock. We´re talking about some rough gagging and ass fucking here--not the session you want to see if you prefer any sensual warmup. The good doctor blew his load in and around her eyes, then scrooped it up and drilled it down her throat with the dildos. Finally, he suspended her and vibrated her pussy in a mean way as a sort of half-reward. Kat was totally owned, but you have to respect her strength.
Format: mp4
Duration: 56:25
Video: 1280x720, AVC (H.264), 2266kbps
Audio: 121kbps



File size: 990.3 MB


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Jem vs. The Ballet Boots Southside

One simple job, that's all she had. Instead of cleaning my house while I was out she spent the time trying on shoes and outfits. When I returned I found her in nothing but some lingerie and ballet boots. What better punishment than to let her spend some quality time in the outfit of her choice! I put leather mittens and a gag in her mouth to prevent any objections and led her to the basement. Once there I attach jem's mitten to the ceiling and she's left with two options. Stand in the ballet boots or hang by her mittens. Either way, she's going to have a long... long time to think about it!
Format: mp4
Duration: 16:19
Video: 1280x720, AVC (H.264), 1925kbps
Audio: 122kbps



File size: 245.1 MB


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Hot Blonde Fucked and Humiliated in Public Mill Spring

Cast: Ash Hollywood ,Lorelei Lee ,Mark Davis
Genres: Sub ,Corporal Punishment ,BDSM ,Domination ,Submission ,foreskin ,Anal ,Blowjob ,fake boobs ,muscular
Video language: English
Lorelei Lee and Mark Davis make Ash Hollywood their slave for the day. Ash is groped and used by video store customers, hooded and clamped and made to suck cock on the store counter while strangers fill her holes with dildos! Lorelei shoves her feet in Ash’s mouth and pussy, using her slobber for lube. Covered in cum, spit on and labeled an A+ cunt, Ash becomes the store’s new window display.
Format: mp4
Duration: 56:19
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps



File size: 615.4 MB


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Dizzy Sex Training At Orange Garden Duck River

Release Year: 2021
Genres: 3DCG, Animation, Anal, Big Ass, Big Tits, Creampie, Cumshot, Femdom, Futanari, Huge Cock, Masturbation, Oral
Video language: English
Tina knows sombody is watching her, she is a teasing sluty girl. And of course she can not resist the biggest cock she saw in her life. But how long is it going to take before Nino realised her dominant potential and shows a real anal punishment for Tina's depravity.
Format: mp4
Duration: 28:46
Video: 1920x1080, HEVC, 10981kbps
Audio: 190kbps



File size: 2.3 GB


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19 Year Old With Big Natural Tits Gets Dicked Down by 5 Older Men Darlington

Cast: Lizzy London ,Mark Wood ,Jack Moore ,Jay Crew ,Blake Palmer ,Otto Bauer
Genres: Corporal Punishment ,19-Year-Old ,Big Natural Tits ,Role Play ,Older/Younger ,Athletic ,socks ,BDSM ,Brunette ,Rough Sex
Video language: English
When 19 year old Lizzy London with her big natural tits comes in to audition for a gangbang 5 older men take her down, tie her up, and have their way with her.
Format: mp4
Duration: 1:01:25
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps



File size: 671.1 MB


DOWNLOAD FROM FILESMONSTER: 19 Year Old With Big Natural Tits Gets Dicked Down by 5 Older Men

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Edith Howard Redmon

Release Year: 2010
Studio: DeviceBondage
Cast: Edith Howard
Genres: BDSM, Humiliation, Torture, Bondage, Pain
Video language: English
The Fellows in Ache masquerade ball is the brilliant setting for the glorious Domina Tory Lane to instruct Her encounter a lesson on making sure She cums first.The 2 creep off into the private basement to fulfill all of Tory’s sexual dreams and to punish Her guy for being selfish and unworthy. Tory uses wordy humiliation, a wrist suspension and a biting cane to hit and mind plumb Her submissive. After a lengthy sesh of cootchie licking and sex, Tory prizes Her marionette permitting him to cum.
Format: mp4
Duration: 21:10
Video: 1280x720, AVC (H.264), 2929kbps
Audio: 122kbps



File size: 473.6 MB


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Sgt Major vs Casey Calvert Morland

Cast: Sgt. Major ,Casey Calvert
Genres: Pain ,Caning ,Tattoo ,Domination ,Ball Gag ,Submission ,Corporal Punishment ,Anal ,the wall ,Fingering
Video language: English
Casey Calvert submits to well known bondage rigger Sgt Major on HogTied. The Sarge torments this super hot brunette super uncomfortable bondage. In scene one, this bitch is stripped of all her clothing and bound with her arms spread standing and a nice neck rope. Sgt squeezes cum from this cunt and rewards her with an intense crotch rope predicament that pulls her hot cunt far away from the wall. Second, she is bound on the y frame face down. Sgt gives her ass and feet a nice caning and adds an anal hook. Her tight cunt is then stuffed tight with a dick on a stick. Third, Casey is bound face down and pleasured with the vibrator on her sensitive clit, but clearly its pleasure before the pain. Sgt Major transitions her bondage into an intense ankle elbow chest hogtie and all she can do is suffer. Finally she is bound in a simple but effective steer tie. The Sarge pushes her with corporal and then hoists her bondage up, exposing her amazing ass. He then goes after her cunt and clit until she can’t take it anymore.
Format: mp4
Duration: 48:02
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps



File size: 524.6 MB


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Lucia Rossi - Valentine's Domination (2025 feb 14) Hackensack

Lucia Rossi makes her debut on Kink with Christian Wilde to explore her BDSM limits for this Valentine’s Day special! Lucia and Christian are enjoying a nice Valentine’s day dinner together when they decide to try some bondage in the bedroom. Christian throws Lucia on the bed and feels her up before stripping off her top to play with her nipples. Testing her limits Christian slaps Lucia’s face and tits before applying some nipple clamps. Christian then has Lucia strip her skirt then he spanks her feet, impressed by her toughness and wetness. Pressing Lucia’s face to his crotch Christian presses the Hitachi to her pussy. Then he makes Lucia suck his cock while Christian continues the pressure, only to have her cum without permission. Christian disciplines Lucia by spanking her pussy before stuffing his cock back in her mouth and making her endure the vibrator until he finally gives her permission to cum. Next up Lucia has her wrists bound to one bedpost and each ankle to another face down ass up giving Christian a great spanking target. He wastes no time and stuffs his hard cock in Lucia’s soaking wet pussy and applies the vibrator to her clit while he fucks her, withholding her orgasm until he sees fit. After some hot fucking Christian breaks out the flogger and really starts reddening Lucia’s supple ass cheeks as he keeps the vibe pressure constant. Soon Christian mounts Lucia and fucks her to his perverted hearts content. Then Christian puts the Hitachi beneath Lucia while he fucks her her hard into the toy, always making her wait to cum, which he finally allows after she begs him. After cumming again Christian dismounts Lucia and fucks her swollen soaked pussy with two fingers and the vibe draining even another orgasm from her. Finally Lucia has her wrists bound behind her back but is otherwise free for Christian to toss around, and he starts by lying her on her back and slapping her tits before spreading her legs and making her beg for him to fuck her, which he generously obliges. After some nipple pinching and tit slapping Christian reapplies the Hitachi while he continues to fuck her, letting Lucia cum again. After requesting Christian slap her stomach harder Lucia cums again, but without permission, so as her punishment he fucks her hard until he cums all over her pussy!
Format: mp4
Duration: 1:03:52
Video: 1920x1080, AVC (H.264), 9776kbps
Audio: 156kbps



File size: 4.5 GB


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Kylie Ray - Panties Still Wet, Horny for More (2025) Kusterdingen

Release Year: 2025
Cast: Kylie Ray
Genres: BBW
Video language: English
I had the wildest night…my underwear is still a mess after such a raw encounter, and I have no intention of washing it, as I don’t want the sweet remnants of my kinky night to wash away, but let me tell you the whole story from the very beginning. My name is Kylie, and I am what many guys at school call “a dork.” I blame my conservative parents, who often punish me for trying to experiment outside my comfort zone. My parents are control freaks and won’t let me be. When they discovered I had been chatting with a guy online named Juan, they punished me hard, trying to prevent me from seeing him. I tried to be a good girl, follow their rules, and log in one more time to tell Juan that things were over, but he persuaded me to meet in person. He came to my house that night, and I secretly let him in, not knowing that this would be an unforgettable evening.
Format: mp4
Duration: 46:07
Video: 1920x1080, AVC (H.264), 3124kbps
Audio: 125kbps



File size: 1.1 GB


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Obedience training kyra part 5 Aldenville

Release Year: 2020
Studio: Graias
Slowly Kyra is becoming a real obedient girl and she learns to accept whatever comes from her Master. Nice to catch this surrender, however her pain threshold is still not at best. She still starts to weep just after a few strikes Dr. Lomp puts on her gorgeous bottom. Lomp is aware of this weakness, enjoys this, and doesn't seem to let her go before getting her blue eyes turning red. Who knows, maybe Kyra also enjoys these punishments, that she doesn't show any hesitation to kiss the hands which hit her brutally.
Format: mp4
Duration: 17:38
Video: 4096x2160, AVC (H.264), 9779kbps
Audio: 309kbps



File size: 1.3 GB


DOWNLOAD FROM FILESMONSTER: Obedience training kyra part 5