RolePlay Porn videos with Fantasy Sex

[LMChallea]

Lets Keep It A Secret.. My Frustrated Stepmom Needs My Load Pierce

Release Year: 2025
Studio: Filthy Kings
Cast: Parker Sims, Andie Anderson
Genres: Blonde, Big Tits, Hardcore, Milf, Old Young, Family Roleplay, Pussy to mouth, Blowjob, Deepthroat, Big Dick, Creampie, Handjob, Cheating, Stepson
Video language: English
With no further ado anal pounding follows in such an intense way and with a variety of positions that the gorgeous babe gapes her hungry asshole.
Format: mp4
Duration: 32:38
Video: 3840x2160, AVC (H.264), 14657kbps
Audio: 125kbps



File size: 3.5 GB


DOWNLOAD FROM FILESMONSTER: Lets Keep It A Secret.. My Frustrated Stepmom Needs My Load

Filthy Kings - Lets Keep It A Secret.. My Frustrated Stepmom Needs My Load Hoisington

Release Year: 2025
Studio: Filthy Kings
Cast: Parker Sims, Andie Anderson
Genres: Blonde, Big Tits, Hardcore, Milf, Old Young, Family Roleplay, Pussy to mouth, Blowjob, Deepthroat, Big Dick, Creampie, Handjob, Cheating, Stepson
Video language: English
With no further ado anal pounding follows in such an intense way and with a variety of positions that the gorgeous babe gapes her hungry asshole.
Format: mp4
Duration: 32:38
Video: 3840x2160, AVC (H.264), 14657kbps
Audio: 125kbps



File size: 3.5 GB


DOWNLOAD FROM FILESMONSTER: Filthy Kings - Lets Keep It A Secret.. My Frustrated Stepmom Needs My Load

Ava Addams - Huge Tits Stepmom Fucks Away His Virginity Glenside

Release Year: 2018
Cast: Ava Addams
Genres: Feature, Couples, MILF, Big Tits, Titfuck, Hardcore, All Sex, Facial
Video language: English
Perfect giant tits stepmom Ava Addams sucks big dick and gets fucked in her perfect hole! Enjoy this exclusive family roleplay fuck with all lust and excitement!
Format: mkv (Matroska)
Duration: 39:46
Video: 1920x1080, AVC (H.264)



File size: 1.7 GB


DOWNLOAD FROM FILESMONSTER: Ava Addams - Huge Tits Stepmom Fucks Away His Virginity

[LMChallea]

The Sauna Myrtle Beach

Release Year: 2024
Genres: BDSM, Bondage, Tits Torture
Video language: English
"The Professor" and "Doctor Davis" are two separate clients who she encounters on her first day as a sex worker. Elise fulfills their fantasies with role play, hard punishment, bondage, anal and rough sex!
Format: mp4
Duration: 56:48
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 622.6 MB


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[LMChallea]

Sasha Grey Vinton

Cast: Sasha Grey
Genres: Handler ,Kinky ,Role Play ,natural boobs ,Sybian ,Bush ,shaped ,Hitachi ,Double Penetration ,Paddle
Video language: English
Sasha Grey is back for another go around with the machines. She warms up with an ass paddling from the Robo-Spanker that leaves her perfect bubble butt rosy red and gets her ready for the machines. Sasha has a pretty tight pussy so what she doesn’t take in size, she makes up for in speed. She gets stuffed on both ends with the Snake and it’s hard to say which end is hotter to watch get plowed - her mouth or her pussy. And be forewarned - Sasha lets out an orgasmic scream on the Sybian that is intense and well, loud!
Format: mp4
Duration: 32:15
Video: 960x540, AVC (H.264), 1366kbps
Audio: 122kbps



File size: 352.3 MB


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[LMChallea]

Seeing Red: Red Hot Reunion Del Rio

Release Year: 2019
Studio: Seeing Red
Cast: Jayden Cole, Scarlett Mae, Jayme Rae
Genres: Redhead, Threesome, Natural Tits, Fingering, Teen, Tattoos, Facesitting, Family Roleplay, Tribbing, Lesbian, pussy eating
Video language: English
Jayden Cole enters the basement and seems surprised to find her second cousins Jayme Rae and Scarlett Mae already sitting there with their faces in their hands. They make small talk for a moment, chatting about how bored they are at the family reunion making awkward chit-chat with relatives they barely even know.
'As if a bunch of 20-somethings like us care about 401ks and kitchen remodelings and all that other crap!' Jayden mentions. The trio shares a laugh which quickly dies into awkward silence.
As they sigh with boredom, the girls make attempts at small talk until Jayden suggests that they play strip blackjack. The other two are a little shyer but ultimately agree.
As hey play blackjack, more and more clothes come off as the girls gradually warm up to each other, Jayme and Scarlett in particular becoming less and less shy. With fewer and fewer clothes on, the girls also become more flirty with each other, making saucy comments and stealing glances at each other's semi-nude bodies.
Eventually, all three girls are sitting in just their panties, the atmosphere increasingly sexually-charged. A mischievous look comes over Jayden's face and she suddenly reaches over to Jayme and playfully tweaks her nipple. Jayme is shocked.
'Hah, sorry! I couldn't help myself. It was practically at me. But that was mean. You can totally flick nipple back if you want! Actually, you guys can even give my boobs a little squeeze if you're curious. Not gonna lie, I wouldn't mind giving both of a little feel too!' Jayden says.
Jayme and Scarlett are hesitant, but ultimately can't resist the temptation.
They compare and touch each other's breasts. As the breast touching becomes increasingly erotic, the atmosphere takes on a strong sexual charge. Feeling the vibe, Jayden lowers her mouth to lightly lick Jayme's nipple. Jayme is a little reluctant at first, but swept up in the eroticism of the moment, she lets Jayden continue to tongue her hard nipples. It doesn't take long for Scarlett to join in, getting her own mouthful of Jayme's perky tits.
Format: mp4
Duration: 34:06
Video: 3840x2160, AVC (H.264), 12275kbps
Audio: 125kbps



File size: 3.0 GB


DOWNLOAD FROM FILESMONSTER: Seeing Red: Red Hot Reunion

The maid Holly

Release Year: 2022
Cast: Nimue
Genres: BDSM, Brunette, Curvy, Fetish, Piercings, Role play, Sex toy, Spanking, Submission
Video language: English
In other words - it´s all about the world of BDSM displayed in pictures and the most severe BDSM videos.
Format: mp4
Duration: 36:50
Video: 720x576, AVC (H.264), 4840kbps
Audio: 309kbps



File size: 1.4 GB


DOWNLOAD FROM FILESMONSTER: The maid

Filthy Kings - Stepsis Just Wants To Help Corolla

Release Year: 2025
Studio: Filthy Kings
Cast: Juan Loco, Blaire Johnson
Genres: Brunette, Big Tits, Fingering, Tattoos, Family Roleplay, Interracial, Stepsister, Pussy to mouth, Blowjob, Deepthroat, Cumshot, Cum in Mouth
Video language: English
Her supple young body is gorgeous but her piercing blue eyes mesmerizes. With a mischievous smile, her face was stunning to look at as she deep throated my cock.
Format: mp4
Duration: 35:08
Video: 3840x2160, AVC (H.264), 14645kbps
Audio: 125kbps



File size: 3.7 GB


DOWNLOAD FROM FILESMONSTER: Filthy Kings - Stepsis Just Wants To Help

[LMChallea]

Busty Milf Gigi Dior in Unforgettable Step Family Vacation Imabari

Release Year: 2025
Cast: Cory Chase, Gigi Dior
Genres: Pornstar, Hardcore, Big Tits, Anal, Blowjob, Creampie, Big Dick, Blonde, Mature & Milf, Bubble, Butt Ass, Double Blowjob, Cunilingus, Fingering, Straight, Caucasian, Stepmom, Family Roleplay
Video language: English
I (Luke Longly) walk into my step-mom's bedroom, where Cory Chase has a towel wrapped around her, and Gigi is completely naked on the bed. Cory drops the towel to the ground and Cory shakes her big tits to tease me. Cory lies down on the bed in the missionary position, and Gigi Dior starts to eat her pussy out in the doggystyle position. At the same time, I am fucking Gigi from behind. I move my cock into Gigi's ass, before she flips over into the missionary position. Then I go back to fucking Gigi's pussy while Gigi is sucking on Cory's tits. Cory climbs on top of me next and she starts to ride my cock with her pussy. It doesn't take long before she moves my cock into her ass hole. Gigi is licking and sucking on Cory's nipples while she's riding my cock. I move my cock from Cory's ass to pussy, back and forth, in no particular order. The two MILF's move into the doggystyle position next to each other, and I take turns fucking all of their holes. They both move into the missionary position and I continue to fuck all of their holes in no particular order. When I am ready to cum, I allow my cock to explode inside of my step Aunt Gigi's pussy. A creampie, just like she wanted!
Format: mp4
Duration: 25:44
Video: 1920x1080, AVC (H.264), 5155kbps
Audio: 187kbps



File size: 1.0 GB


DOWNLOAD FROM FILESMONSTER: Busty Milf Gigi Dior in Unforgettable Step Family Vacation

Lady Phoenix The Fantasy Curator H265 part 2 Rayland

I am an experienced creative roleplay specialist, an erotic aesthete and a full service dominatrix.
Format: mp4
Video: 1080x720



Total size: 2.7 GB in 42 files.

DOWNLOAD FROM FILESMONSTER: Lady Phoenix The Fantasy Curator H265 part 2

Office persecution Millburn

Release Year: 2020
Studio: ThePainFiles
Cast: Ellarna
Genres: Female Sub, Fetish, Role play, Spanking, Submission
Video language: English
ThePainFiles is by far the most insanely perverted web site on the internet.
Format: mp4
Duration: 45:14
Video: 1280x720, AVC (H.264), 7784kbps
Audio: 309kbps



File size: 2.6 GB


DOWNLOAD FROM FILESMONSTER: Office persecution

[LMChallea]

Home Invasion yoha Moriches

Release Year: 2011
Studio: BoundGangBangs
In this fantasy role-play update Yoha dreams of having her house invaded by a pack of horny men who tie her up and use all her holes for their pleasure. She struggles as she is taken down and tied up, but eventually she succumbs to the cock and cums so hard she squirts all over the floor. Sex in bondage, hard anal pounding, double penetration, and cum covered faces await you inside!!!
Format: mp4
Duration: 53:52
Video: 1280x720, AVC (H.264), 4882kbps
Audio: 122kbps



File size: 1.9 GB


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Fat cunt destruction Petaca

Release Year: 2020
Studio: ThePainFiles
Cast: Slavegirl Emma
Genres: Female Sub, Fetish, Fingering, Role play, Slapping, Spanking, Submission
Video language: English
Warning: Hardcore Pain and SM Material! Don´t go any further if you don´t love extreme BDSM.
Format: mp4
Duration: 39:49
Video: 1280x720, AVC (H.264), 7761kbps
Audio: 309kbps



File size: 2.3 GB


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[LMChallea]

The Unfaithful Hindsboro

Cast: Dia Zerva
Genres: BDSM, Submission, Bondage, Blowjob, Ball Gag, Domination
Dia Zerva finds herself victim of blackmail when her secret love affair is caught on video tape. Blackmailer John Henry demands sexual favors when she comes up short with the cash. This is a very erotic role play performed beautifully by Dia and John with great submission and super hot bondage sex including anal and hard iron restraints.
Format: Windows Media
Duration: 1:01:54
Video: 1280x720, Windows Media Video 9, 1464kbps
Audio: 125kbps



File size: 741.8 MB


DOWNLOAD FROM FILESMONSTER: The Unfaithful

Sibling Rivalry Searsboro

Release Year: 2021
Studio: Yummygirl
Cast: Sofie Marie
Genres: MILF, Hardcore, All Sex
Video language: English
Role play screne. Sibling rivalry a taboo tale alex is home from school and finds his mom in the laundry room, and one thing leads to another, and sofie sucks off alex, and then he fucks sofie on the washer/dryer and cums in her wet pussy. Rion is sniffing his mum's panties and masturbating when sofie catches him! Rion is super embarrassed but sofie assures him that it's really normal for a young man to be turned on by the scent of a woman's panties. They both agree not to tell papa, and sofie offers rion a fresh pair to smell right off her body! He takes a deep smell and sofie goes down on him and sucks his young cock. As rion is overwhelmed by the sites and smells, and sofie climbs on rion and starts riding his hard cock. They have sex in many different positions until rion mistakenly cums in his mom's pussy! Sofie cleans herself and then puts on the panties to collect his jizz. She offers to wear them all day and leave them on his pillow tonight! Alex comes home from school and sees sofie resting in the bed, and he has a devious idea. Maybe i can slide it in her and she won't wake up! Alex slides it in her ass! Sofie eventually wakes up from her nap and alex and sofie have hot anal sex, since its better for birth control! Rion and alex are home from school, and they are comparing their sexual exploits. In a typical game of brothers trying to one up another, they each confess that they have had sex with their papa's wife sofie! After a verbal battle of who the parent likes better, the boys rush into sofie's bedroom to have her settle the tie. The catch her right out the the shower and confront her. She is stunned that the boys didn't keep their dirty secret, but eventually she warms up to the idea. As a typical parent, she can't pick favorites, so she has them compete for her lustful affections. She blows them both, and then they take turns skewering her, in different positions, then she lets them take turns double penetrate her- one in the pussy and one in the ass! Still undecided, she tells them to cum on her face and the first one to cum wins!
Format: mp4
Duration: 1:25:27
Video: 1920x1080, AVC (H.264), 4489kbps
Audio: 184kbps



File size: 2.9 GB


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[LMChallea]

Office slut Brainard

Release Year: 2025
Studio: ThePainFiles
Cast: Katerina , Satine Spark
Genres: BDSM, Female Sub, Femdom, Fetish, Lesbian, Redhead, Role play, Spanking, Submission
Video language: English
This particular website the Pain Files has probably the largest collection of Fetish pics along with sickly BDSM ever created. Every bondage type and torture is featured in this case. You might invest weeks exploring this large website. Have a look, you will not be disappointed. Warning: Hardcore Pain and SM Material! Don´t go any further if you don´t love extreme BDSM.
Format: mp4
Duration: 48:23
Video: 1280x720, AVC (H.264), 7781kbps
Audio: 309kbps



File size: 2.8 GB


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Slave Contracts and Financial Domination Wagener

Cast: Penny Barber and Ella Nova
Genres: Domination, Submission, No Sex, Humilation
Video language: English
Ready to kick your D/s up a notch, or even try it full-time? Here's what you need to know about consensual contracts, binding your partner into service to you, including guiding their spending habits. Penny Barber and Ella Nova demonstrate Slave Contracts as tools of negotiation and service. They also discuss and demonstrate how to use Financial Domination for deepening engagement with your submissive on a full-time level as well as money-oriented games and role playing.
Format: mp4
Duration: 33:44
Video: 1280x720, AVC (H.264), 4828kbps
Audio: 122kbps



File size: 1.2 GB


DOWNLOAD FROM FILESMONSTER: Slave Contracts and Financial Domination

[LMChallea]

Taboo Heat - Rebel Rhyder in Championship Season Step Sister Gangbang Kevil

Release Year: 2024
Studio: Taboo Heat
Cast: Cory Chase, Brickzilla, Jonathan Jordan, Rebel Rhyder, John Long
Genres: Blonde, Big Tits, Girl on Girl, Hardcore, Masturbation, Anal, Fingering, Milf, Facesitting, Family Roleplay, Tribbing, Interracial, Stepsister, Facial, Blowjob, Deepthroat, Cumshot, Double Penetration
Video language: English
Cory Chase is sitting down on the weight bench in the gym, and she is lifting weights. Her step-sister, Rebel Rhyder, walks into the gym, and they start to chat. It doesn't take long before Cory stands up and she wraps her arms around her step-sister's body. She begins to kiss Rebel's mouth, and then Cory lifts up her t-shirt, exposing her big tits. Cory takes her shirt off and then she lifts Rebel's shirt up as well. Cory begins to lick and suck on her step-sister's nipples. Rebel gets completely naked before she lies down on the weight bench with her legs spread. Rebel starts to finger her own pussy, before Cory takes over and finishes her off. Afterwards, Cory pulls her shorts down and she moves into the doggystyle position on the weight bench. Cory flips over onto her back and she spreads her legs for her step-sister. Rebel eats her pussy out while fingering her at the same time. After Cory cums, the two MILF's get into the scissor position and they rub their clits back and forth on one another until they both cum again.
'Are you ready for a bit of a challenge?' Cory Chase asks Rebel Rhyder. Cory tells Rebel that they have a new team member named Brickzilla, who happens to have a very big cock! 'Do you think you'd be able to fuck three team members today?' Cory asks Rebel. Rebel is excited to try and take on three cocks at the same time! But first, they want to start to Brick. They call him into the room and he appears, with one of the biggest cocks Rebel has ever seen! Rebel gets down on her knees and she starts to suck on his huge cock. The other two teammates (John Long and Jonathan Jordan) walk into the gym and they're eager to join Rebel and Brick, while Cory is watching. Rebel starts to suck all three cocks, one right after the other.
Brick starts to fuck Rebel in the ass, while she is sucking the other two cocks. She does double penetration next, while Cory stands behind her cheering her on. While Rebel is being D.P'ed, she has the third cock in her mouth. Two of the giant cocks fuck her asshole at the same time next, and Rebel enjoys every moment of the double anal penetration! When they are ready to cum, they take turns jerking their cocks off on her face, and into her mouth...
Format: mp4
Duration: 49:32
Video: 1920x1080, AVC (H.264), 4999kbps
Audio: 187kbps



File size: 1.8 GB


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Dueling MILF Secretaries Ranger

Cast: Holly Heart, Syren De Mer
Genres: BDSM, Bondage, Anal, Fisting, Big Tits, Humiliation, Dildo, Lesbian
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: 1280x720, AVC (H.264), 4903kbps
Audio: 122kbps



File size: 2.5 GB


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Annalese Reno, Molly Little - Molly Casts Annalese Reno (2025) Atwood

Release Year: 2025
Cast: Annalese Reno, Molly Little
Genres: Threesome
Video language: English
In part two of this month's Nubile podcast, we watch Molly Little help Annalese Reno dive into one of her fantasies with Juan Loco dressed as her stepfather. Role playing Analese's best friend, Molly comes over to help Annalese seduce her sexy stepdaddy. Without any further pretense, the girls ease Juan down onto the couch so they can flank him and have their way with him.
After peeling Juan out of his robe, Molly and Annalese get on their knees to blow him together. They stroke and suck in tandem, enjoying everything about Juan's fuck stick. They get him laying down so that Molly can mount his hardon in cowgirl and Annalese can ride Juan's tongue.
Switching it up so that Molly is on Juan's face and Molly is bouncing on his dick, the girls put their stepdad through his paces. Molly gets on her knees to eat Annalese out while Juan fucks her in doggy. They wind it down with Molly cradling Annalese's shoulders as Juan dives nice and deep to make her moan. Pulling out, Juan covers Annalese in his jizz right on her cute little tan lines.
Format: mp4
Duration: 25:17
Video: 1920x1080, AVC (H.264), 9175kbps
Audio: 191kbps



File size: 1.7 GB


DOWNLOAD FROM FILESMONSTER: Annalese Reno, Molly Little - Molly Casts Annalese Reno (2025)

[LMChallea]

Penny Barber and Ella Nova - Slave Contracts and Financial Domination West Chester

Release Year: 2025
Cast: Penny Barber, Ella Nova
Genres: Domination,Submission, No Sex, Humilation
Video language: English
Ready to kick your D/s up a notch, or even try it full-time? Here's what you need to know about consensual contracts, binding your partner into service to you, including guiding their spending habits. Penny Barber and Ella Nova demonstrate Slave Contracts as tools of negotiation and service. They also discuss and demonstrate how to use Financial Domination for deepening engagement with your submissive on a full-time level as well as money-oriented games and role playing.
Format: mp4
Duration: 33:44
Video: 1280x720, AVC (H.264), 4828kbps
Audio: 122kbps



File size: 1.2 GB


DOWNLOAD FROM FILESMONSTER: Penny Barber and Ella Nova - Slave Contracts and Financial Domination

Airi Mashiro - Fun GF Experience Sex With Airi (2025) Parmele

Release Year: 2025
Cast: Airi Mashiro
Genres: Asian
Video language: English
So many of you dream of dating a pornstar. And we love to bring you immersive POV date videos through which you can feel like that’s finally happening to you. The pornstar of today’s GF experience POV movie is Airi Mashiro. She was recently featured in a roleplay office sex adventure on our site, and everyone loved her for how obedient and nympho she can be at the same time. She came so many times in the previous scenes. And if you think she is awesome in such roleplay scenes in which she is used, you should see her in this scene in which our guy is a true gentleman and focuses only on her pleasure. He offers her a nice date experience over tea and teases her with compliments and by showing how turned on he is by her beauty. He then made her spread those sexy legs and started exploring her perfect pussy with his fingers. It didn’t take long for this skinny hot babe to cum all over her new lover’s hands.
Format: mp4
Duration: 59:15
Video: 1920x1080, AVC (H.264), 7799kbps
Audio: 125kbps



File size: 3.4 GB


DOWNLOAD FROM FILESMONSTER: Airi Mashiro - Fun GF Experience Sex With Airi (2025)





Exclusive Circle of Girls Clarinda

Cast: Maitresse Madeline Marlowe ,Mckenzie Lee
Video language: English
Porn Star Mckenzie Lee makes her debut on WhippedAss in a fantasy roleplay about a nosy co-ed snooping around in places she shouldn’t be. Mckenzie finds herself in deep shit at the hands of bad girl Maitresse Madeline in the locker room after class. With no one left to hear Mckenzie’s screams Madeline woman handles her gigantic breasts, slaps her pretty face, spanks her cute ass till it’s bright red and rips orgasms from her cunt. Her nipples are tormented and she’s made to lick ass. She’s fucked in bondage with a huge strap on cock in both her holes till she can’t help but admit what a dirty little slut she really is.
Format: mp4
Duration: 53:43
Video: 960x540, AVC (H.264), 1367kbps
Audio: 122kbps



File size: 587.1 MB


DOWNLOAD FROM FILESMONSTER: Exclusive Circle of Girls