RolePlay Porn videos with Fantasy Sex

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The Curious Case of Casey Cumz, vol.1 - Casey Cumz Part 2 Dangeoncorp Middlebranch

Release Year: 2025
Studio: Dangeoncorp
Cast: Casey Cumz
Genres: BDSM
Video language: English
I have a collection of 50 anal dildos, Im very dominant, Im very tough...this woman was very reserved...the type of reservation that can only either be shyness or stoned coldness...we talked for a long time about the motivations behind the BDSM fantasies and the role playing behind the BDSM realities...she listened and seemed to totally understand everything I was saying...or was it going right through her head?...I couldnt tell...we talked so much, that when we got finished, we skipped the members interview and went right into the shoot...Bane wrapped her arms to vertical poles and wrapped her legs together with vet wrap...he toys with her for a few minutes before he gives her a big test...clover clamps right onto the nipple...she moans and it's real...she slowly recoils to deal with the sensation...Bane takes her right into flogging....then dragon's tails...this woman is tough...without a doubt...her poise impresses me...and when the vibrator goes on, she loss control...then lying on her tummy with her head and wrists locked into stocks...a spider gag in her mouth...her legs spread and held in place by steel cuffs...once again, we decide to see if Casey can walk the talk when it comes to her love of anal toys...we break out the fucksaw with a good sized dildo...first she moans and pulls against her binds...there's no room to move...Bane pulls the trigger and runs the saw faster and faster...until she is screaming with delight...Casey passed with flying colors for certain...but still, she is a peculiar woman...
Format: mp4
Duration: 11:50
Video: 1920x1080, AVC (H.264), 4292kbps
Audio: 309kbps



File size: 399.7 MB


DOWNLOAD FROM FILESMONSTER: The Curious Case of Casey Cumz, vol.1 - Casey Cumz Part 2 Dangeoncorp

Mom Swap Pt 4 Muir

Release Year: 2025
Cast: Lauren Phillips, Crystal Rush, Ricky Rascal, Carmela Clutch, Carmen Valentina
Genres: MILF, Mature, Big Dick, Big Tits, Cougar, Erotic Vignette, Family Roleplay
Video language: English
These sex starved MILFs are in for a big treat when they find out the young cocks they crave are right under their noses in Mom Swap 4. When things get hot, step sons make it hotter by turning this 4-way fantasy in to an all out mom swap.
Format: mp4
Duration: 2:48:59
Video: 1280x720, AVC (H.264), 2935kbps
Audio: 125kbps




File size: 3.7 GB


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Hogcuffed Complete Erotic BDSM Prison Shackle Roleplay part 1 Woodbine

Here you will find videos of girls in jail and in prison serving hard time. This isn’t your typical prison.
Format: mp4
Video: 768x576



Total size: 6.7 GB in 50 files.

DOWNLOAD FROM FILESMONSTER: Hogcuffed Complete Erotic BDSM Prison Shackle Roleplay part 1

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Hogcuffed Complete Erotic BDSM Prison Shackle Roleplay part 4 West Liberty

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: 6.3 GB in 47 files.

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Hogcuffed Complete Erotic BDSM Prison Shackle Roleplay part 2 Dille

It is run by Warden Lola Lynn who was once a prisoner herself. At the Hogcuffed prison the girls are always kept in restraints, even while in their cells.
Format: mp4
Video: 768x576



Total size: 6.9 GB in 50 files.

DOWNLOAD FROM FILESMONSTER: Hogcuffed Complete Erotic BDSM Prison Shackle Roleplay part 2

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Hogcuffed Complete Erotic BDSM Prison Shackle Roleplay part 3 Devils Elbow

You will see the girls get punished, forced to orgasm, and treated like the Warden’s little toys. The use of steel shackles,chains,cuffs and dental mouthspreaders and gags help the warden to keep the inmates in check.
Format: mp4
Video: 768x576



Total size: 6.6 GB in 50 files.

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Onlyfans Gwen Gwiz Scn. 33 Mountain Lakes

Video language: English
Onlyfans Gwen Gwiz excitedly approaches a dresser, talking to herself, saying 'I can't believe Scn finally gave me an empty drawer of my own at his place... Things are getting pretty serious with us...' But as she opens the drawer for the first time, a piece of paper, which must've been stuck to the roof of the drawer, falls down. Her excitement turns to curiosity, then confusion when she unfolds the paper and sees a list of women's names, including her own. All of the women's names, except her own, have been crossed off. She approaches her boyfriend, Scn Gamble, to eke the truth out of him since she's too meek to confront him directly. But all of her attempts fail as Scn brushes her off... until she suggests roleplaying a hookup between strangers (with her using a name from the list). Scn is intrigued and gives into having lustful sex, though he still seems oblivious to all Leana's attempts, giving up nothing. But just how oblivious is Scn, really...?
Format: mp4
Duration: 1:31:32
Video: 1280x720, AVC (H.264), 5859kbps
Audio: 156kbps



File size: 3.9 GB


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Street Prostitute Little Chloe Gets 6on1 BBC Orgy With DAP & Rough Sex Stamford

Release Year: 2024
Cast: Little Chloe
Genres: Orgy, Gangbang, Hardcore, Anal, DAP, 0% Pussy, Golden Shower, Piss Drink, Creampie, Swallow, Mouthful, Roleplay
Video language: English
In this hot gangbang, lustful bitch Little Chloe gets a serious BBC lesson with airtight double anal penetration!
Format: mp4
Duration: 1:08:34
Video: 1920x1080, AVC (H.264), 7070kbps
Audio: 205kbps



File size: 3.6 GB


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Isis Love receives a submission from Katie Summers. La Fria

Cast: Isis Love ,Katie Summers
Video language: English
In this roleplay update Katie Summers plays a college girl looking to earn some extra cash. On a friends referral she comes to see Mistress Isis Love, but has no idea what she is really in for. Isis fucks Katie hard with her electric cock, clamps and zaps her tits, flogs her ass, and makes her cum uncontrollably. The more pain Katie takes the more money she will earn, but can Isis Love ever really be satisfied?
Format: mp4
Duration: 59:05
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 645.8 MB


DOWNLOAD FROM FILESMONSTER: Isis Love receives a submission from Katie Summers.

Bonkers MayDay Alverda

Release Year: 2020
Genres: 3DCG, Animation, Anal, BDSM, Creampie, Cumshot, Huge Cock, Oral, Sex Toys, Futanari
Video language: English
Valerie is back. And this time she's going to fuck Alice. "Mayday" is Alice's safe word. Will Alice need to use her safe word, as they explore some kinky role playing?
Format: mp4
Duration: 20:22
Video: 1920x1080, AVC (H.264), 9148kbps
Audio: 309kbps



File size: 1.4 GB


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Self Adoration Cassoday

Release Year: 2015
Studio: Fetish Artcore
Cast: Tigerr Benson, Madame Adore, Brianna Dane, Anita
Genres: Leather, Rubber, Fetish Sex, Dildo, Deep Fucking, Anal Fucking, Pissing, Sucking
Video language: English
Naughty teenage rubber schoolgirl slut Anita needs to be taught a lesson. And what better way to do so than spanking her bare round bottom and fucking all of her tight holes one after one until covering her cute pretty face with cum... Thank heaven for naughty girls.
Petit Brianna Dane knows how to pleasure herself. A powerful monster fucking machine and a magic wand will get her off and these machines know just what buttons to push and never get tired of pounding her tight little pussy.
Madame Adore knows how to mix things up. Schoolgirl rubber play showing off her tight body and teasing our interpretation of innocence. Finishing us off by pissing all over herself and into her mouth. School was never this good...
In this intimate and personal scene Madame Adore explores the pleasures of self fulfillment. With her rubber fixation, self enduced breath control, vibrators and the sybian, Madame Adore brings herself to tears of ecstasy.
Skoolgrrrl Adore is left alone to her own devices and enjoying her schoolgirl role play. So much so she can´t keep her fingers away from her bright pink dildo as she fucks herself while brushing her teeth. And to finish off she drenches the camera in hot Skoolgrrl piss.
Tigerr Benson is bound in beautiful bondage while being thoroughly abused orally, vaginally and anally by Sebastian Solo. Through several physically testing bondage positions Tigerr elegantly enjoys every sadistic treatment she is exposed to and ends the scene begging gratefully for a face full of cum.
Format: mp4
Duration: 1:34:28
Video: 1280x720, AVC (H.264), 2916kbps
Audio: 153kbps



File size: 2.1 GB


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Asa Akira submits to a woman for the very first time! Healdsburg

Cast: Chanel Preston ,Asa Akira
Genres: shaved ,humiliation ,fingering ,asian ,face-sitting ,lesbian ,latex ,bondage ,black-hair ,corporal-punishment
Video language: English
Famous pornstar Asa Akira subs for the very first time at WhippedAss! Asa has never been dominated by a women! In this sexy roleplay update Asa plays a high powered business woman looking for some extra curricular activities to forget about the stresses of responsibility. She hires professional dominatrix Chanel Preston to give her a night to remember filled with sexy lesbian fetish sex. Here is a chance to see Asa dominated by a woman for the very first time including, spanking, ass and pussy worship, humiliation, latex worship and fisting!
Format: mp4
Duration: 1:18:06
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 853.8 MB


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Ex-adult performer Kirsten Price endured a violent Douala

Cast: Aiden Starr ,Kirsten Price
Video language: English
Former Wicked contract star, beautiful? Sure. Tough as nails? You’ll have to see it to believe it! Welcome Kirsten Price to Whipped Ass. Not only is she drop gorgeous but she loves BDSM. In this kinky lesbian roleplay Kirsten is a new recruit for the military but they have other plans for her training. Kirsten is subjected to tough caning, single tail, evil clothes pins ripped from her tits with water and then made to cum. She’s put in back bending bondage spanked and fisted to orgasm then wrap in medical wrap and double penetrated and cums from anal penetration!
Format: mp4
Duration: 1:11:37
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 782.9 MB


DOWNLOAD FROM FILESMONSTER: Ex-adult performer Kirsten Price endured a violent

The Most Deliciously Forbidden Parsonsfield

Cast: Ramon Nomar ,Simone Sonay ,Chastity Lynn
Video language: English
In this forbidden fantasy role-play Simone and her step Chastity become sexually acquainted with each other through Simone’s boyfriend Ramon. Chastity’s constant flirting with Ramon has taken it’s toll and she finds herself playing a kinky game where she is tied up, punished and fucked in the ass right along side her step mom!
Format: mp4
Duration: 1:16:16
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 833.8 MB


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Dee Williams, Sonny Mckinley - Roleplay With Me My Cartoon Crush 1080P Part 2 Spotsylvania

Video language: English
2 Dee Williams and horny lesbians bring out their favorite toy.
Format: mp4
Duration: 42:30
Video: 1920x1080, AVC (H.264), 4549kbps
Audio: 187kbps



File size: 1.4 GB


DOWNLOAD FROM FILESMONSTER: Dee Williams, Sonny Mckinley - Roleplay With Me My Cartoon Crush 1080P Part 2

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Dueling MILF Secretaries Pentress

Cast: Syren de Mer ,Holly Heart
Genres: redhead ,fingering ,slave ,strap-on ,femdom ,lesbian ,pussy-eating ,lezdom ,rough-sex ,role-play
Video language: English
Welcome back super MILF, Syren De Mer, and evil MILF domme, Holly Heart, to Whipped Ass. In this kinky lesbian role play Syren plays a secretary looking for a new job in Holly Heart’s office where she has been the secretary for Mr. Dickinson for over 6 years! It’s obvious Holly runs this office and she will stop at nothing to keep it that way! Hot MILF on MILF lesbian domination and rough sex with fisting, spanking, pantyhose and deep strap-on anal sex!
Format: mp4
Duration: 1:09:07
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 757.6 MB


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Role-Playing Game With A Sexy Milf - Holly Halston Kanorado

Release Year: 2014
Cast: Holly Halston
Genres: Anal, Uniform, Cuckold, MILF, Huge Tits, Raven, Wife, Blowjob (POV)
Video language: English
Holly Halston was dressed up as a sexy cop, ready for a little roleplay with her husband, who was supposed to be waiting for her at home. So imagine her surprise when the burglar she confronts in her bedroom isn't her husband at all!
Holly quickly takes control of the situation, telling the burglar Keiran Lee to take his dick out for her. She gives that fat cock a nice sloppy deepthroat blowjob, and then bends over so he can fuck her deep in her tight pink pussy.
Finally, Holly takes that big dick in her juicy ass, giving the horny burglar all three of her holes while her big tits bounce and she cums over and over on Keiran's big dick. One facial later, and Keiran is a free man... this time!
Format: mp4
Duration: 32:38
Video: 1920x1080, AVC (H.264), 11665kbps
Audio: 124kbps



File size: 2.8 GB


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Dap, tap for russian beauty rita with gaping butthole! Drayton Plains

Release Year: 2012
Studio: BoundGangBangs
Russian babe Rita plays the victim in this fantasy role play home invasion update! Double anal, double vag, triple penetration, sensory deprivation, bondage, fisting, squirting, and hardcore gangbang action!
Format: mp4
Duration: 1:08:32
Video: 1280x720, AVC (H.264), 4882kbps
Audio: 122kbps



File size: 2.5 GB


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Helpless in Russia: Rough Sex Fantasy Role Play Oslo

Cast: Savannah Secret
Genres: BDSM, Anal, Double Penetration, Fisting, Submission, Domination
In this BDSM fantasy update, Savannah is out on her own in the streets of Saint Petersburg looking to meet up with a friend when she gets lost and her cell phone battery dies. She meets a stranger on the street who offers to charge it at his apartment close by which she agrees out of desperation. Inside the apartment, she finds herself helpless and at the mercy of two strangers who wrestle her to the ground and tie her up. Her darkest fantasies come true as she is manhandled and fucked very rough. Then she is tied up in the bathtub and given a humiliating so that her asshole can be fucked! The intensity ramps up even higher as she endures painful clamps all over her body and she is fucked in the ass while her pussy is fisted. However, all this leads to powerful orgasms that she cannot control. Savannah is then double penetrated by the strangers and then hogtied in a hot sauna where they come on her pretty face and leave her there to bake.
Format: Windows Media
Duration: 1:09:40
Video: 1280x720, Windows Media Video 9, 1464kbps
Audio: 125kbps



File size: 834.8 MB


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Anal Jesse - Cheerleader Roleplay - Ass To Mouth And Cum Swallowing 1080P Part 1 Denver City

Video language: English
Cheerleader Roleplay had been dating a married man who has no interest in leaving his wife. Cheerleader Roleplay decides to surprise him at his house. She pretends that she's a neighbor and tries to make friends with his wife. He breaks up the little party and calls up Scott. He tells him that she needs to be taught a lesson. He pretends that her lover has sent flowers but the real reason why he's there is to punish her!
Format: mp4
Duration: 19:11
Video: 1920x1080, AVC (H.264), 7829kbps
Audio: 294kbps



File size: 1.1 GB


DOWNLOAD FROM FILESMONSTER: Anal Jesse - Cheerleader Roleplay - Ass To Mouth And Cum Swallowing 1080P Part 1

Homewrecker 2: The Rancher's Daughter Ploiesti

Cast: Dee Williams, Natasha Blu
Genres: Rough Sex, Anal, Deep Throat, BDSM
Small Hands is back to do some more backwards ass ranch hand wreckin' in this weeks Family Role-play Homewrecker 2: The Rancher's Daughter. Stepmother Dee Williams has been stockpiling money from her rich husband and plans to skip out under the radar. But Blonde cutie step-daughter Natasha Blu wants to botch that plan and take the money for herself so she reigns in the help of trusty ranch hand Small Hands. Ms Blu saunters over to him wearing high heels and a teeny tiny mini skirt that shows off her smooth round ass. She seduces him with a super hot blow job that would convince anybody to steal for her. With her perfect natural tits bulging out of her shirt she plays with her pussy and gags and gargles on his huge cock. Will these young lovers get away with their devious plan? Lo and behold step mother Dee Williams barges in on them with her huge tits busting out of her dress and Small Hands has a change of heart. He can't resist…after all he's always been a “tit man”. He dominates the situation and before running off with the money himself he has to get a piece of these two lovely ladies. A crazy step-mom/daughter fest of rope bondage, flogging, blow jobs, zappers, fucking and pussy eating ensues. Small Hands ties Dee to the bed in a squatting position with her pussy exposed and tits roped up. Natasha is tied up tight on a table with a ball gag stuffed in her mouth and her skirt pulled up for easy action. First he crams his cock all the way down Dee's willing throat and gives her a good throat fucking. With his dick nice and wet he fucks Natasha's pussy and plays with her clit until she cums hard. Small Hands unties Dee and sets her mouth loose on Natasha's pussy. Hands gets his dick sucked while Dee voraciously eats her step daughters cunt. Time for some serious ass fucking. He ties them both up in doggie style and fucks Dee's ass until she squirts and cums all over his cock. Ms Blu cleans her step mom's cum off Small Hands cock with her lusty tongue and then he fucks her tight ass. Both Dee and Natasha get a good hard pounding in all their slutty holes. Now they are both tied up on their backs connected with rope at the ankles. Small Hands has his way with Dee and then Natasha and back again, ass to pussy to ass to mouth and back again until they are loosing it. Small Hands knows how to fuck with that big dick and he gives it good to these hungry squirting sluts until he shoots his hot ranch hand load all over their sweet faces. Wrecked!
Format: mp4
Duration: 51:40
Video: 1280x720, AVC (H.264), 4859kbps
Audio: 122kbps



File size: 1.8 GB


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Anal Jesse - Nurse Roleplay - Anal Jesse Treats Blue Balls 1080P Part 2 Hunker

Video language: English
Nurse Roleplay alisha - 19yo babe with big natural tits first monster cock in anal.
Format: mp4
Duration: 13:25
Video: 1920x1080, AVC (H.264), 7828kbps
Audio: 310kbps



File size: 800.5 MB


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