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Showing 1-60 of 485 Results

Big Dick Guy Ball busted by Cougar MILF 2 video from PaintedRose

Big Dick Guy Ball busted by Cougar MILF 2 Rosie's daughter's boyfriend comes over while she isn't there and Rosie decides..sit;s time he fixed her light bulb in her bedroom. She's dressed in black sexiness and removes her clothing while he is fixing the light bulb. He turns around to see her in seamless black hosiery, platform heels, and a bra. She decides she will seduce him. Why not? She starts gently dominating him with sensual seduction. What follows is a blowjob tease where he finds out that HIS BALLS BELONG TO HER NOW! Throughout fucking and sucking, Rosie has his by his balls literally. Squeezing, pulling, tugging, jerking. She tells him his cum belongs to her too. She blows him and jerks his balls hard for a HUGE close up facial. She let's him know he needs to be at her house tomorrow to move some boxes. Behind the scenes included. this is a custom video of gentle femdom and light ballbusting! Thanks! Biggest cumload PDG (Prop DIck Guy) has ever blown!!

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Mesmerized: To Get Fucked and Eat Cum video from PaintedRose

Mesmerized: To Get Fucked and Eat Cum Your Sex Therapist Rosie is working with you because you've been having some sexual issues and during the session we get to the root of the problem. After being put into a trance state of open minded readiness for reprogramming, Rosie tells you why your dick isn't getting hard. You need to get fucked...by a guy! Rosie brings out the different sizes of cock - smallest to biggest and discusses how you liked dick even when you were small. The locker rooms and college days were hell as you denied yourself the inner pleasure you desired. It's time to stop having those inhibitions and fear. Rosie reprograms you to be fearless and teaches you how to be anally stimulated, to suck a big dick, and to eat cum! You wake up from the trance only knowing that you are relaxed and ...ready. JOI, CEI, Mesmerize, Femdom, Masturbation encouragement.

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The J Files: Vintage Sensual GFE video from PaintedRose

The J Files: Vintage Sensual GFE Sensual J wants to seduce your body and mind with her sensuality and it's all in the eyes. I am so Juicy and on fire for you and your stiff, throbbing cock. Watching you watching me as I touch rub and feel your eyes burning back into me, I start to touch and fuck until I cum for you and then tell you to cum on my pink pussy. I knew we'd be hot together. This is a seductive duel masturbation where I virtually bring you into me bed and fuck you. Thank you!

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Sissy Sister Wife: Bull Cock Threesome video from PaintedRose

Sissy Sister Wife: Bull Cock Threesome Your best friend in the whole world invites you over for tea and to ask you an important question. You're a Sissy Girl and a femininely beautiful naughty sweet girl and Rosie knows you're attracted to her husband. Rosie tells you that the doctor told her that she needs to take it easy while pregnant due to hubby being a big wild bull with a thick juicy dick and appetite for lots of sex. Rosie says that hubby is attracted to you too and that she asked her husband if he would like you to be part of the family as a sister wife and he happily agreed to it. Rosie knows the pregnancies will keep coming and she wants her hubby to be happy and satisfied, you love being part of the fam and could be a second Mom and wife in the family. What do you think? If you agree we can go tell my husband right now! Hubby is so excited to hear the news that he can't hide it.. so we have a threesome and sexual loving initiation into the fam! This is a Sissy, CD, TG, Feminization love story and a .. happy ending! Thank you!

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Confessions Of A Cock Craving Cougar video from PaintedRose

Confessions Of A Cock Craving Cougar Mrs. Flowers sees you outside of the field house and stops to chat confessing how her daughter and all the girls have a crush on you. She tells you they voted you as the winner of the biggest 'Dick Print' vote at the party. She asks if you're busy and if you can swing by her house to move some furniture. Back at her place, she begins to flirt and asks if the rumors are true about you having a big dick. You're bulging and she confesses that her marriage is just for the fam and her hubby is out of town.. it's just the two of you and she's looking for a young man to teach everything she knows about sex. Before you know it, you're getting a blowjob and titty fuck and then she tells you to cum in her married mouth. It doesn't take long for her to get you hard again and she fucks you cowgirl, doggy, and missionary dripping creampie!

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The Deal: One Time and Don't Tell Anyone video from PaintedRose

The Deal: One Time and Don't Tell Anyone You walk in to see Step-Mom cleaning with no panties and a short skirt. She usually at least has panties on and now you can't hide your erection any longer. You tell your Mom why your face is red, you're embarrassed because of your erection. She feels terrible when you tell her that it's her outfits and that you tried to look away but that it is her fault. Step-Mom feels so bad that she tells you that you need to masturbate to feel better and get the erection to go down. You ask if she can help by letting you look at her posing for you and she reluctantly agrees as she knows now that she should have dressed more appropriate in front of you. Back in Mom's room she is deciding whether to go through with this and begins to dance in her lingerie and then you come in and talk her into helping you since you've never seen a real girl naked before. You ask Mom to pose, and then show her boobs, then pussy, then ass. You tell her you want to touch her pussy with your dick and she then agrees but before you know it, you are fucking Mom doggy style and then ask her to ride your dick like the girls do in porn films. You ask Mom if you can cum inside of her and she tells you that it's already gone too far and this will be the first and last time! Bonus Rosie scene at the end - long toy session and real orgasm. Hey I get horny filming lol! This is a POV, Stepmom, Mommy Fetish taboo roleplay fantasy video.

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Panty Party: Sissy Slut Girl Games video from PaintedRose

Panty Party: Sissy Slut Girl Games You're invited to this private party and uhm.. NO BOYS ALLOWED! Bring your cutest, slutty panties to play together in this girl girl panty party. We can start with trying on panties, shaking our asses, and talking about being naughty. I brought you a butt plug and I am going to wear one too! Panties, butt plugs, and dildos .. OH MY! Let's practice your sexy slut sissygasms by you sucking and fucking my dildo. You're so sexy when you shake it for me :) Let's play!

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Aunties Pantyhose: Pussy Play and Fuck video from PaintedRose

Aunties Pantyhose: Pussy Play and Fuck You walk in on Auntie at a dinner party back bedroom and she is masturbating and doesn't notice you watching. She orgasm squirts her pantyhose and then notices you there. She immediately starts sucking your cock and tells you not to tell your parents. She doesn't think you'd even know what to do and she tells you to prove you can fuck a real woman. Then she gets on and rides you cowgirl before bending over for some Doggy Style! Next you get on top to show her what a man you and she tells you to cum inside because she wants flooded and can't get pregnant. You fill Auntie full of cum and she thanks you for it! POV Step-Aunt Fantasy Roleplay with Gentle Femdom Rosie and her dildo..and you!

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Mom's Red Dress: Taboo Love Affair video from PaintedRose

Mom's Red Dress: Taboo Love Affair Step-Mom Rosie is getting ready for a date and can't decide which dress to wear and so her son offers to help. She changes behind the curtain into three dresses and has her son pick the dress. He can see through the curtain and saw everything, unknowing to Mom. He chooses the red dress and as Mom gets the call that her date is cancelled, she notices her son's erection! Mom confesses her attraction to her son too. She is overcome with passion and begins to suck her boy's cock and has him do the same to her. She teaches him what she likes and then climbs on him and fucks him with her tits in his face. He loves it and missionary creampies his mother and they confess their forbidden love. Thank you for this custom Roleplay scenario with Mommy Fetish, Fantasy taboo roleplay, gentle femdom, dancing, forbidden love in a POV style film.

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Mom's New Husband: Better Than Dad video from PaintedRose

Mom's New Husband: Better Than Dad Step-Mom Rosie comes home from work and you two discuss her job and life since Dad left. Mommy notices how much you've been doing to be the man of the house since Dad left her for a younger woman. Mom tells you how he didn't make her happy anyway. He didn't want to let her get pregnant, he didn't love her unconditionally, and he didn't even eat pussy! You tell Mom that she doesn't need him or another guy because she has you now and you will do all of those things. After telling Mom that you're man enough, she decides to put you to the test after teasing you with her body. She says you're amazing after she cums in your mouth and then tells you that you're getting something Dad never did - you get to cum in her mouth! After a long BJ, Mom asks you to meet her in her bedroom and when you arrive you fuck Mom in all positions. To your surprise, Mom has a proposal for you. As her husband you can have your wish to stay together forever and if you get her pregnant, you can finally give her what Dad wouldn't, making her pregnant. Thank you for this custom film! I loved making it. This is the ultimate Mommy fetish, wedding, love, impregnation fantasy roleplay POV interactive film with several cum scenes. Thank you!

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Chastity Affirmations: Caged Cuckold video from PaintedRose

Chastity Affirmations: Caged Cuckold You've started to get weaker and more desperate for release and Rosie is here to reaffirm for you why you need to remain in a cage until further notice. You came to see Rosie and soon realized what your little dick has needed all along - to be placed in chastity so that you can show your loyalty, love, and earn your Mistresses approval and eventual release to cum for her on your knees like a good cuck cum servant should. You don't have a release date because you are still in training and so you must do your very best to be considered to have earned the privilege of cum allowance. At this time you are caged only and it is time to go over your task checklist, reaffirm why you need to be in chastity, and given some encouragement to keep you going on the tough days and long lingering nights. On this day, Rosie makes it so sexy that you begin to drip in your cage - no touching or tugging - just your Mistresses torturous twisted teasing to tantalize your teeny tiny tot size dick into a frenzy of servitude. It'll be worth it when you've completed all of the tasks. Serving is your reward and cumming is letting you out of misery just long enough to make you beg for more. Thank you!

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Caged In Panties: Mom's Porn Addict video from PaintedRose

Caged In Panties: Mom's Porn Addict You've been watching porn and you're on a tight leash as you've been caught already. You also sneak and spy on Step-Mom when she's resting, showering, or changing. She walks in on you touching it again and watching porn and this time she is prepared! She comes back with a chastity cage and pink panties to teach you a lesson. You like watching MILF porn? How about if your MILF Step-Mom watches you?!? Put the panties on now and start jerking while Mom watches, objectifies, and punishes you! Mom makes you cum while yelling at you that she is going to change your pervy ways and that you will be under close supervision as she locks you in a chastity cage. For my Feeble Friend - Thank you for this custom film.

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The Pussy Cat Heist video from PaintedRose

The Pussy Cat Heist Rosie is a professional Pussy Cat Burglar who especially enjoys mind fucking her weak minded losers for their inability to resist her persuasive pussy power seduction. Whatever the prize, it's your perverted surrender of her cock controlling conquest that turns her on the most. She's been watching you and following your every move. Lights Out. This is going to be too easy... Thank you for getting this custom made film that features Femdomme / Submissive dynamic, Cat burglar theme, capture and bondage, blindfold, imminent corporal punishment for refusal of compliance, mind fuck, pussy control, pervert shaming, exposure and humiliation fantasy roleplay. This film is 2257 compliant and a solo performed roleplay fantasy. FemDomme Listings: Film Keywords: MILF, Cougar, Femdom, Cuckold, Cuck, Cucking, Goddess, Dommy, Mistress, MommyDomme, Gentle Femdom, Positive Femdom, Sensual, FemDomme, Rosie, PaintedRose, MILF Rosie, burglar, heist, cum control, pervert, humiliation, weak, submissive, pussy control, curvy, big tits, big ass, big boobs, bondage, rope, seduction, trickery. Film Hashtags: #MILF, #Cougar, #Femdom, #Goddess, #Dommy, #Mistress, #MommyDomme, #GentleFemdom, #PositiveFemdom, #Sensual, #FemDomme, #Rosie #PaintedRose #MILFRosie, #burglar, #heist, #cum #control, #pervert, #humiliation, #weak, #submissive, #pussy control, #curvy, #big #tits, #big #ass, big #boobs, #bondage, #rope, #seduction, #trickery.

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Why Mommy Wears Pantyhose video from PaintedRose

Why Mommy Wears Pantyhose The feel, the look, the arousal of Step-Mom's pantyhose is too hot to not look and you've been watching for years and today is about to be even hotter. Mommy arrives home per usual and you tell her that you'd like to go to dinner. She tells you to let her shower and change because she's been in these pantyhose and tight clothes all day. You tell Mom she looks great and you tell her you noticed her rubbing her legs in a sensual way. She reveals that you are old enough now to understand all the reasons why she wears hosiery. Step-Mommy discusses how she likes to seduce with her pantyhose adorned legs and you can't help but to also become aroused by this. Mom says you two can't just go out all hot and bothered and recommends a naughty masturbation game to see who will cum first. There can only be one winner - maybe. This POV seamed control top in suntan pantyhose video has handjob, blowjob, cum on pantyhose and lots of seduction! Thank you for this custom film.

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Goddess Worship: MommyDomme's Body and High Heel JOI video from PaintedRose

Goddess Worship: MommyDomme's Body and High Heel JOI You love all of Dommy's curves and love to worship all of her body on your knees like a good JOI boy. Today I come home from my date and am so excited to tell you about getting fucked while you jerk and stroke to my instructions. Today my legs in thigh high nude hosiery in sexy heels is just too much for you and I make sure that you make it to the end before you cum. Today Dommy wants you to spend the last couple minutes of worship to be focused on Mommy's sexy HEELS! This film is 2257 compliant and a solo performed roleplay fantasy. This film features; female domination, femdom, heels, pantyhose, thigh highs, hosiery, Goddess, Worship, POV, Dirty Talk, Tits, Ass Pussy, Curvy, Step-Mom, step-Mommy, Taboo, Jerk Off Instruction, FootBoy, FootSlave, Feet, Foot, Toes, Soles, Hose, Thigh High, Tease, Pantyhose, Worship, Goon, Gooner, Gooning, Goddess Mistress, Dommy, MommyDomme, Femdom, FemDomme, Cuckold, Cuck step-Son, JOI, Jerk Off Instruction! #Foot #FootBoy #FootSlave #Feet #Foot #Toes #Soles #Hose #Thigh High #Tease #Pantyhose #Worship #Goon #Gooner #Gooning #Goddess #Mistress #Dommy #MommyDomme #Femdom #FemDomme #Cuckold #JOI #JerkOffInstruction #Taboo #MILF #POV

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Dommy: Bound and Beating video from PaintedRose

Dommy: Bound and Beating You awoke to MommyDomme in Lingerie wearing a stethoscope and realize you're bound and gagged. Mommy is in charge and straddles you looking into your eyes as she puts on her stethoscope and begins to listen as she grinds into your hopeless groin area. Maybe you have a stethoscope fetish she asks.. Maybe You just love your Mommy.. Maybe you like being Dominated.. You are helpless in between MommyDomme's thighs. Thank you for this custom video. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Step-Mom's Tease and Denial Games: 3 Days video from PaintedRose

Step-Mom's Tease and Denial Games: 3 Days To play along, you will need Dice, Cards, and a Coin. If you'd like - a chastity cage can also be applied at certain points. It's Game night and you and Step-Mom have a three day weekend of games and good times planned. During the game, you keep going to the bathroom to masturbate and hide your boners. Step-Mom figures out what the problem is and says that she can train you to have put a stop to the constant need to touch your penis and masturbate but that you will have to give her complete control. You agree - what choice do you have - this is Step-Mom and she knows what is best for you. The games are a game of luck and fate - no more and no less but the twist is when you win, you get to touch your penis and if you lose.. you can only watch as Step-Mom teases you. Each day you build up wins and on the last day it will come down to Cum, Don't Cum, or Ruin your orgasm! If you do not cum, the game begins again. Are you ready to play? Thank you for this Custom Film.

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Goddess Rosie: Serve My Every Desire So Sweetly video from PaintedRose

Goddess Rosie: Serve My Every Desire So Sweetly Never keep your Goddess Rosie waiting. It's important to earn the favor of my love with your every sending of worship to meet all of our aching desire. We begin with you on your knees and your only task is be ready to please as we begin with a full body tease. You may also play if you do as I say. My lips and hips, tits and ass, feet and toes but Goddess knows... You desire to taste and we proceed with much haste to the agony of my perfect pink pussy ruining you for only me. Your Goddess Rosie is SIMP-ly the BEST. This 2257 compliant film is a solo performed adult roleplay fantasy that features StepMom Fetish, First Time, Taboo, Roleplay, Dirty Talk, Curvy MILF. This film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate/comment this video highly with a nice review. DM me to order your own Custom video. Please follow and subscribe for all behind the scenes and so much more! Thank you SO MUCH! #Goddess #Worship #Simp #Serve #Send #Goon #MILF #Femdom #Dommy #Domme #Sensual #Domination

^$24.00 Add to Cart

Mom's Pantyhose Pleasure: Son's Surprise video from PaintedRose

Mom's Pantyhose Pleasure: Son's Surprise Step-Mom Rosie gets home from work and checks on you - you are resting in her bed so sweetly. Mommy is changing and dancing with her headphones on and doesn't hear you getting up. You can't help but watch her dance topless in those nude seamless pantyhose that you love so much. She's obviously turned on - you're Mom gets horny and you can't help to touch your stiffy. just then, she notices you aroused and touching and she freaks out! She can't believe what she saw - you with a stiff one and jerking it to your Step-Mother! The mood changes after she sees how good you look naked and she starts touching and teasing until the two of you decide to masturbate together. Cameltoe play and then after she squirts the pantyhose, she asks you to cum by rubbing your dick on her pussy through the pantyhose. Yummy!

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Cuck Life: Fuck Your Wife video from PaintedRose

Cuck Life: Fuck Your Wife It's so exciting - your first time swinging - a wife swap. You met a sexy couple at church who are super sexy and welcome you and your wife to get together for a fun time. The curvy and seductive female half of the couple has been flirting with dirty texts and promises you dirty hot sex. You eventually talk your innocent prude wife into it and the big night is finally here! Rosie takes you into her bedroom where you're still in earshot of your wife and her husband in the next room. Rosie begins telling you all about her husband and how he's had his eye on your wife's tight body for weeks and consoles you not to worry because she will be taken care of properly. Rosie knows you're expecting to fuck her and asks you to take it out for her and so you do with anticipation. She says that your wife will never be able to feel your average penis again after her bull husband is done fucking and filling her. What do you mean she's not on birth control? This was all too easy - stroke it while I tell you how your life will never be the same. This custom made film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. Femdom Keywords for this video: Cuck, Cuckold, Cucking, Cuckoldress, Cucky, Cuckhold, Femdom, Wife Swap, JOI, Bull, Average size, humiliation, Jerk Off Instruction, Beta, Submissive, Domme, FemDomme, Dommy.

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Sissy Bachelor Party: Brother's Sister video from PaintedRose

Sissy Bachelor Party: Brother's Sister You're really disappointed your Step-Brother doesn't think you will fit in with the other guys at his bachelor's party and Step-Mom, the party planner has a great idea! MommyDomme Rosie dresses you up and teaches you how to do the 'entertainment' as the stripper of course. You'll need a couple of lessons on how to be a slut first. Once you put on your sheer, see through sexy outfit, it is time to learn how to seduce, strip, and suck! This is a POV Sissy Slut Feminization Training Video! Let's have a Sissygasm with our cute little AssPussy, Shall we? Let's get to the party for the surprise finale!

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Mother-In-Law: Sperm Bank Blowjob video from PaintedRose

Mother-In-Law: Sperm Bank Blowjob Your intake nurse at the sperm bank looks a lot like your hot Mother-In-Law and you can't help but being turned on by her exam and the fact that she knows you're there to cum! Once in the playroom, you look up from your tightly gripped meat stick to see your Mother-In-Law dressed in sexy nurse lingerie and dancing / teasing you like never before. She says surprise as she assists you with some badly needed erotic visualization but soon suggests a hands on approach. Nurse Mommy can't believe her daughter sent you by yourself to jerk into a cup when a man like you deserve some very personal and oral attention. A stiffy like yours deserves to be slobbered and sucked on.. and she takes matters into her own hands and mouth and gets you off like a good nurse Mom-In-Law. Fetishes: MILF, Cheating, Handjob, Blowjob, Stripper, Step-Mom, Medical Play, Nurse, Mother-In-Law. Thank you for getting this film!

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Boss's Dick Gets Used by Busty Secretary video from PaintedRose

Boss's Dick Gets Used by Busty Secretary Rosie's boss, "Sir" loves watching her feet even though HE IS MARRIED! They work on business but he keeps looking at her arched feet in slip on shoes. She pretends not to notice and then starts teasing him by rubbing lotion on her legs and feet. She notices his huge bulge in his pants and offers to help him with it and he resists because he has a wife... Rosie Doesn't care. He tries to act like he is working while being a perv. He shouldn't be using her to look at when he is supposed to be working! She decides not to take no for an answer. Rosie tells him that he is not allowed to tease her from across the room. She uses his cock and doesn't even make him cum. She orgasms and then goes back to work...promising to not tell and leaving him wanting for more. POV Homewrecker cheating husband and wife.

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Valentines Day 2023 Live Date Subscriber CumShow video from PaintedRose

Valentines Day 2023 Live Date Subscriber CumShow Oh my gosh - we had a fun and naughty time.. Wheel Spins throughout and lotsa naughty dancing, Jiggles, and some wiggles. Thank you for all who.. came!!! Love to you o this special day. Thank you for showing me love so I didn't have to be alone. You made it so so special!

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Circumcision Decision: Penectomy Persuasion video from PaintedRose

Circumcision Decision: Penectomy Persuasion A Rosie Original. You've been referred to a specialist Doctor for a circumcision and when you arrive you are greeted by a the one and only Dr. Flowers. She begins setting up and dicussing the medical necessity of your procedure and how she will make it painless, precise, and the procedure that is best for her patient. She says that you need a full circumcision due to your circumstances and encourages you to consent and states that she won't even charge you more as it's her duty as a doctor to perform the procedure that is best for her patient. She's given you an antibiotic injection with a little something extra to help you relax. She grips your penis to begin numbing it and assisting with achieving a full erection - for the most precise incision. Her alternative methods are very pleasing and you sign your final constent. Let's get started, shall we? This film is 2257 compliant and a solo performed medical roleplay fantasy. This film features medical equiptment, gloves, injection fantasy, a slow build to increase the suspense, a real registered nurse experienced in many things - wink wink, penectomy encouragement, femdom, sensual domination, and an ending that will make you completely powerless to your doctors desires. #Penectomy #Circumcision #Femdom #Sensual #Domination #MILF #Humiliation #Medical #Fetish

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Panty Pervert Punishment video from PaintedRose

Panty Pervert Punishment You're a panty sniffing pervert and the kind that sniffs your own Step-Mom's panties. You've been caught and don't even try to talk your way out of it. How dare you go through my hamper and panty drawer for your own depraved desires for Mommy cunt? You will be banished to your room and punished for eternity as now you are forever completely owned and destroyed by the forbidden fantasies of this perfectly pink Mommy fuckhole and the delicious sex juice that my lovely cunt fills the cotton crotch with. You're going to to show Mommy how you jerk off with my panties while I tease you with my everything. Start jerking. NOW! Painted Rose Films and content is 2257 Compliant Fantasy Roleplay - Curvy Taboo Femdom MILF ROSIE! This flm contains: #Taboo # #Panty #Fetish #JOI #PantySniffer #JOI #JerkOffInstructions #Humiliation #Goddess #Mistress #Dommy #MommyDomme Femdom #FemDomme #Submissive #Training

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Ballbusting Inquisition: Feet and Defeat video from PaintedRose

Ballbusting Inquisition: Feet and Defeat Rosie's long inquistion and POV story mode describing the ultimate feet and defeat of a man's dignity. He thought he would mess with this petite MILF with tiny feet but she gave him what he didn't expect. FemDomme Foot Domination and the sacrifice of his masculinity as he gets ball busted into submission. After the defeat she is detained for explicit questioning and goes into great detail describing his suffering beneath her stilettos before he finally succumbs to her Foot FemDomination and Ball Busting CBT Punishment! Thank you for this custom video. This film is 2257 compliant and a solo performed adult roleplay. Please heart and rate my video 5 stars. Join my fanclub for thousands of free pics. vids, and behind the scenes exclusive Milfyness. Love, Rosie

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Homework Helper: Mom's In College Too video from PaintedRose

Homework Helper: Mom's In College Too You are starting back for Fall semester but this time, Step-Mom is going back to school and has a class with you. You come home early after your last class and accidentally see Mom getting out of the shower - she runs upstairs very embarrassed and apologizes later. You tell her you didn't see anything but, you did! You can't believe your own Mom is a MILF.. Some of the guys really like her and YOU don't like that. Mom even cancels her study date with this guy because you tell her he is a creep and so you and Mom decide to study together. You can't control that you keep getting turned on while studying - she's always dressed like a young Mom but now you realize how desirable her body is. Your friends can't have her, she is your Mom and best friend! When Mom sees your boner she tells you it isn't appropriate and laughs that you should masturbate or else you won't be able to rest well for class in the morning. After confessing how much it is hurting, your nurse Mom has a look and can't hide how impressed she is with your large, beautiful penis. She wants it and says she wants to be the first one to give you a blowjob. She lovingly kisses your cock and teaches you about how she likes being fucked and really gets super wet. Mom rides you back and front, underboob, on top, doggy style, missionary creampie. Real close up rosie-gasm where you can see how engorged Mom is as she busts on your stiff dick. Now it's your turn to cum inside homework buddy.. Thank you and I hope you love this taboo fantasy step-Mom roleplay film.

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The Wife Swap Scheme video from PaintedRose

The Wife Swap Scheme Your life long best friend and his curvy, sweet wife are frequent visitors with you and your wife. For years.. the secret looks, longing gazes, and burning desires to have your buddy's wife are driving you to scheme a plan with her. You both want eachother and begin to work on your spouses to make them think it is THEIR idea to couple swap.. and then you two can finally be together without the guilt or breaking up your family. This film has a hot building up of sexual tension, slow stripping, curvy, sweet fuck doll wanting your dick and you badly, slurpy blowjob, twerking doggy, titty bouncing, wet missionary pound and a cowgirl dripping creampie finish!

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Hot Summer Vacation: Auntie's Good Boy video from PaintedRose

Hot Summer Vacation: Auntie's Good Boy HD Only. You arrive at Auntie Rose's place for the summer and you've both changed a lot since last time you saw eachother. Auntie is married but lonely and so glad to have you come to stay. She says she runs a tight ship - no messes or bad boy stuff and she is not worried because you look like a good boy. Auntie's big titties are always on display and slipping out at home, the beach, or when she bends over to kiss you before bed and you can't help being turned on by such a sweet but no BS powerful woman. Little slip ups, naughty glances, staring too long into your needing eyes has you aching with sexual fantasies. You're having so much fun all summer all while falling inlove with her. You're caught of guard when Auntie spits in your mouth and tells you that you're going to be her new young man. She pulls out your dick and says it's much bigger than her husband and then she begins to suck and fuck until you almost.. No no no.. She didn't have a condom and doesn't want to get pregnant so she invites you to cum in her mouth... you cum all over her face - which she loves and licks it up. You taste like sweet boy cum. This video has Step-Aunt Taboo Roleplay, female led relationship, seduction, hot lust, underboob, doggy style, her on top, blowjob BJ, cum facial, nurturing sweet with spicy mama vibes.. Thank you for this custom video. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Honeymoon Homewrecker 4K video from PaintedRose

Honeymoon Homewrecker 4K (CV) You and your wife are in town for a wedding where she is very busy helping the bride and leaves you unattended. You meet up with your old flame Rosie after the wedding and it seems she's still got a thing for you. You're a little worried about your wife catching on that you're getting a little fucked up and flirting with an ex. Rosie still has those curves and remembers everything that you like.. and need. She knows what she's doing dancing like that and getting you all loosed up tossing some back and getting you plenty of refills. You're a little dizzy staring down at her bouncy natural boobs and remembering how her lips fit perfectly on your knob. Well one thing leads to a spill all over your suit and Rosie assists you as you stagger together giggling all the way to her room with a big bed.. and a lock on the door. Before you know it.. You're stripped and being sucked on - she's starving for your cock and you need this! You're the one that got away but not tonight. This film is heavily centered around curvy cleavage, nipple slips, Corset titties, 2 blowjobs or three.. a cowgirl fuck and you're on top for the finish. Quite heavy with sensually steamy seduction and the best fuck you'll ever have. Thank you for this custom film!

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Engorged: Milking For Rosie video from PaintedRose

Engorged: Milking For Rosie Engorged: Milking For Rosie - It's my first time leaving the fam since giving birth and I am a little worried about losing my milk supply and so I've brought a breast pump on the business trip. I called to see if you want to meet up while I am in town and can't wait to see you. When you arrive, I have a dilemma - I can't get my milk to let down with the pump and I'm really hurting and worried about a clogged milk duct. I don't know what to do so I ask you if you'd mind suckling to stimulate the feeling of breastfeeding and though you're reluctant because I am married, you agree to help. I straddle you so gravity can help and then you flick your tongue, lick, and suck my nipples. The milk isn't coming out but I am getting so horny that I accidentally cum. I am so embarassed - that wasn't cheating was it? A couple of days later you call to chat and find out I am leaving tomorrow night and you offer to bring over dessert to my hotel and help me again if I am still hurting. After sweets, we decide to try again because the pain is so bad. While we are trying to get my milk to release, we are both getting horny and your ready stiff cock accidentally slides right into my slippery sex hole.. ooops and we keep going because perhaps an orgasm can help save my milk supply. I tell you not to cum in me even though I am probably not ovulating yet.. Thank you for this custom video! This film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. KeyWords: Blonde, Mature, Natural Tits, Milk, Thick, BreastMilk, Squirt, Female Orgasm, Sex, Suckling, Love, POV Sex, Breastfeed, Kink, Suck, Fuck, Underboob, Curvy, Curves, Chubby, Big Lips, DSL, Rosie, MILF Rosie, Painted Rose, PaintedRose, Engorged, Cheating, suckle

^$14.00 Add to Cart

Rosie's Live Cam-Cum Show 7-12-24 video from PaintedRose

Rosie's Live Cam-Cum Show 7-12-24 We Chill, We Dance, We Get Naughty, We Fuck! Cum With Me! Missed the show? That's ok. I recorded it for you. We can still have ALL THE FUN! Free in my SUB CLUB along with all of the other camshows!! #Live #Cam #Camshow #MILF #Step-Mom

^$10.00 Add to Cart

Sissy Cuck Fuck Boyfriend Training video from PaintedRose

Sissy Cuck Fuck Boyfriend Training This is a Sissy Cuckold Roleplay fantasy. You have been waiting impatiently for your new girlfriend to give up pussy and she said she isn't ready for sex. So you've snuck off and jerked with her panties! Problem is she caught you and locked you in a cuckold cage. No she asked you to help her get ready and so you agree and as she gets ready she reveals a new and even smaller cock cage for your little dick. She continues getting ready and tells you she has a date because she is ready to get fucked by a real dick, a man size dick. You get on your knees to serve while she tells you all about how things will be from now on. She is going to sissify you in all ways, especially your asshole. She gives you a JOI. Will she ruin your orgasm by making you cum soft with a vibe on your cage?

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Seamless Obsession: Black Pantyhose Seduction video from PaintedRose

Seamless Obsession: Black Pantyhose Seduction You're completely helpless and under my control in these soft seamless pantyhose. Why do you think I am wearing them? You get weaker and become heated up in the agony of defeat. Complete body worship and for the finale, we focus on my beautiful seamless covered pussy. This Rosie Original film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. MILF Cougar, MILFY, Blonde, Mature, Natural Tits, Thick, Juicy, Horny, Insatiable, Depraved, Perverted, Kink, Suck, Fuck, Curvy, Curves, Chubby, Big Lips, DSL, Rosie, MILF Rosie, Painted Rose, PaintedRose, Virtual Sex, Femdom, Good Boy, Asshole, Sensual, Loving, Sweet, Seduction, Seductive, Sin, Sinful, , Facial, Cunt, Mommy Cunt, Fuckhole, Shaved, CumPlay, Spitplay, Cum, Tits, Titties, Tittys, Boobs, Boobies, Breasts, Nipples, Pantyhose, hosiery, seamless, tights, JOI

^$12.00 Add to Cart

Wittle Wee Wee Boy: SPH/SPE Diapee video from PaintedRose

Wittle Wee Wee Boy: SPH/SPE Diapee The date is going great and in fact you've got Rosie down to her lingerie making out and then you take down your pants to display your dick and everything stops. Rosie is shocked and tells you that it's too small and not big enough to please her and that she's completely turned off by the size of your baby-dick. In fact, Rosie apologizes for losing interest sexually and feels terrible. She says there is only one way she can keep you around and that's if you become her wittle baby-boy. She tells you she always wanted to have little ones and she likes you a lot and that if you become her wittle wee wee boy she can hug you and kiss you and feed you and change you. No cummies in the diapee - only pee pee allowed. Are you going to go pee pee or cummy in the diapee? She wants you to give her a special wittle warm spot in the front of your pants. What a good wittle boy - Mommy Wuvs you.

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Rosie's Assistant: Prop Girl Promotion video from PaintedRose

Rosie's Assistant: Prop Girl Promotion I am looking for an assistant - preferably a female that I can trust due to the adult nature of my work. My Stepson (You) is looking for a job and we decide that he can interview for the position. Step-Mom is looking for help with errands, promo and customer service, set prep and cleanup, wardrobe assistant and maybe more if it works out. I had really hoped for a girl but am glad to hire someone that I trust. Will it bother you seeing me nude and using toys? A week has gone by and you're doing so well that I'd like to see how you do taking and editing photos for me today! Amazing. It's a FILM DAY .. YAY! I'm filming a feminization video today and I could really use a real model - a sexy prop plaything in panties to take my strap on.. You'd be perfect! I've always known you were really a girl - this is the day you've always dreamt of. Go put these pretty pink panties on and let the fun begin! Thank you!

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Suck Fuck Cuck: Your Step-Mom and Your Bully video from PaintedRose

Suck Fuck Cuck: Your Step-Mom and Your Bully You arrive home from another rough day of getting turned down by girls on campus! Coming home to the comfort of your Step-Mom is all you want and need right now. What's that noise coming from the livingroom - is she working out? You walk in on her with your campus bully filling her Step-Mommy fuck holes! She is surprised to see you home early and tells you she invited him over to talk about the bullying and he explained his side of the story. How dare you be upset about him stretching my juicy Step-Mommy cunt when you clearly antagonize him in class! As punishment - you must stand there and watch what a big dick boy can do with his penis that you can't. You don't deserve to ever have your tiny dick sucked or fucked by any girl - you will be cucked. This film features, bully, bull, cuck, cuckold, sph, humiliation, masturbation humiliation, average penis size humiliation, mommy fetish degradation, blowjob, femdom, MommyDomme, verbal humiliation, cuck-Son training. Thank you for this custom video! This film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. ********** Dommy KeyWords: Rosie, Painted Rose, PaintedRose, Goddess, Mistress, Step-mom, StepMom, Step-Mom, Step-Mommy, Step-Mother, MommyDomme, Step-Mama, Step-Momma, Step-Mom, Domme, Femdom, FemDomme, Sex, XXX, POV, Taboo, Taboo Sex, Roleplay, MILF, MILFY, Fetish, Depraved, Perverted, Kink, Suck, Fuck, cuck, cuckold, cuckolding, sph, small penis humiliation, degradation, verbal humiliating

^$14.00 Add to Cart

Nurse Pants: Embarrassed MILF Pants Down video from PaintedRose

Nurse Pants: Embarrassed MILF Pants Down Nurse Rosie comes from the nurse agency to go over all of your new medications and do your assessments to help you recover at home. During her teachings her pants slide down 4 days in a row and she never believes you when you tell her. She thinks you are having visual hallucinations. On the fourth day you convince the nurse to look down and to her shock, her panties are exposed! She apologizes and runs out with her pants still down. This is a custom Video. Thank you.

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Dad's New Wife: Blackmail Blowjob video from PaintedRose

Dad's New Wife: Blackmail Blowjob Rosie is your new Step-Mom and she's working out ok but, you have other ideas for her. She's headed out for the evening while Dad is out of town and she asks do you need anything and has a little heart to heart chat about trying to be a good Step-Mom. She comes back late and you know exactly where she was - out dancing and not with her girlfriend. You catch her coming in late and try to blackmail her for a blowjob. Rosie is one step ahead of you. She tells you to show her your dick and if she likes it, she will suck it. Rosie gives you the blowjob of your life and then turns the table on you with news that she received your report card in the mail. Rosie orders you to her bedroom because she has plans to NOT tell Dad about your grades. This is a Taboo Step-Mom, Blowjob, POV, Cheating Wife, Blackmail-fantasy, Femdom, MommyDomme, seduction video. Thank you!

^$12.00 Add to Cart

Body Swap Transfer: Gym Rat/Cougar MILF video from PaintedRose

Body Swap Transfer: Gym Rat/Cougar MILF You've got this cool app that allows you to body swap with a personal trainer to get better results. All of a sudden you're in some older chick's body and you're kinda freaked out but it's only for 5 minutes. So whatever you look down and go for a feel on the boobs and pussy. Wow. You find a mirror and check it out and can't believe you're in a cougar's body. A busty, curvy MILF! You call the app store and finally get an answer and they are working on it so it might be a while. That sucks but you're a fun guy and gonna make the best of it. You snoop in this chicks drawers and put lingerie on her body and find her dildo...no way. This is so weird. So you start touching down there and have your first female orgasm Wow so that's what it's like for a woman. You really want your muscles and penis back! You don't want to be in her body. You don't know how long this will take. This is a custom video.

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Pretty Panties Please: Dommy's Perfect Punishment video from PaintedRose

Pretty Panties Please: Dommy's Perfect Punishment Step-Mom gets a call that you're being fired from your job because you were peeping on women in panties in the changing rooms.. again. You've been caught and punished before and I thought you got this panty thing out of your system. It is time for a more permanent solution as Dommy can't keep bailing you out of these messes. You're being permanently transformed into a girl in panties so that you can obsess over sexy panties and as part of the punishment you will be put into chastity by me to endure hours daily of teasing and edging in agony. You will not be permitted to cum you very naughty girl unless you can cum from Dommy's Dick Strap-On. This film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate/comment this video 5 stars with a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. This film features, Satin Panties, Feminization, Sissy Training, Sissy Slut, Sissygasm, Girl-Pussy, Clitty, Boy To Girl Transformation, Light humiliation, Chastity and Release, Edging, Step-Mom Taboo Roleplay, Caught Peeping, Panties, Fullback, Bikini, Strapon sex, Cum Control, Orgasm from fucking femdom fetish kink. A Rosie Custom Feminization Gentle Femdom Film - Made for Wolfie. Big Hugs and Heart for my dear friend.

^$16.00 Add to Cart

Date Night Detour: Ordering In video from PaintedRose

Date Night Detour: Ordering In You arrive for your date night with Rosie but, she offers you a detour to her bedroom instead! She starts undressing and seducing you to fuck her. She strips, sucks, and fucks you Missionary Creampie but you're still hard so she finishes you off with some Doggystyle dick riding. You decide to order in and on the menu is MILF PUSSY! This is an interactive POV GFE, Cougar, MILF, Roleplay Video. Heels, Hosiery, Lingerie, Fellatio, Missionary, Creampie simulation, Doggy style Pussy Fucking. Thank you.

^$12.00 Add to Cart

Dommy's Degraded Sex Slave: Bound Beg Breed Training video from PaintedRose

Dommy's Degraded Sex Slave: Bound Beg Breed Training Dommy decides that you need a refesher on your leash, spit and swallow training. Say please and open your mouth like a good slave-step-Son. Thank Mommy for this gift as I lead you around on all fours where you get the pleasure of looking up at Dommys ass. You have been a degraded pussy free fuck toy used to feed Dommy's desire for cum and lots of it for so long and in agony! You are told to go wait naked in dommy's bed - no blankets, no dinner, no cumming today as your punishment for your failure as a breeding pet. You are startled as Dommy binds your hands and feet to the bed where you will stay until she is sure that you've gotten her pregnant. She begins slurping aggresively on her owned cock and balls with a starvation in her eyes that you haven't seen before. She's evil as she climbs on top and begins screaming at you to breed and fill her taboo Mommy cunt! She takes your cum again and again - you mumble that you're getting sore to which you receive cock slaps and spit in your face. How dare you try to get out of it cum slave! MOOOOORRRRRRRRE CUM for Dommy! This custom film features humiliating slave training, taboo Mommy and Step-Son dynamic, Leash and collar, spit and swallow play, breeding impregnation, dirty talk, 3 creampies, FemmeDomination, bondage rope play, a little cbt cock ball slapping for disobedience, a real squirting on your face rosie-gasm, and an awesome real thunderstorm! It was so crazy I even lost power while filming for a bit. This film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. FemDommy KeyWords: Rosie, Painted Rose, PaintedRose, Goddess, Mistress, Step-mom, StepMom, Mom, Mommy, Mother, MommyDomme, Mama, Momma, Mom, Domme, Femdom, FemDomme, Sex, XXX, POV, Taboo, Taboo Sex, Roleplay, MILF, MILFY, Fetish, Depraved, Perverted, Kink, Suck, Fuck, degradation, verbal humiliating. cum control, orgasm denial, cuck, cuck-son, cuckolding, delicious FemDomination, spitplay, spit, squirt, leash, collar, pet, puppy, slave, slave training, agony, degradation, humiliation, breed, breeding, impregnation, cum slave.

^$18.00 Add to Cart

Girl Cocks: A Futanari Story video from PaintedRose

Girl Cocks: A Futanari Story You and your MommyDomme have a very close bestie relationship and you even participate in her FemDomme performances! You told her about a clinical trial where you're getting all of this money to take an experimental medication. She could really use some extra cash too and so you decide to do it together. All is fine and the two of you plan to go out dancing - no side effects so far, but you're feeling abnormally extra horny! When you arrive, Mommy discovers she's grown a huge tripod of a cock and you surprise her by showing her yours! You both have big futa dicks and are hornier than ever! I ask you to stroke your big thick dick with me and we both get turned on that we start kissing like lesbians - chicks with dicks! Nothing feels better than a blowjob so we 69 it so that we can blow are loads of cum in eachothers mouth. After we cum, we have pussies and clits again but we're still so horny that we eat start eating eachother's pussies for a close up clit swelling good time! We're gonna have to get more of this medication! Thank you for this custom film! This film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie.

^$15.00 Add to Cart

Twisted Torment: Basement Boy video from PaintedRose

Twisted Torment: Basement Boy I hope you're enjoying your new dungeon dwelling and diet of bread and water. You will be tormented in my twisted training torture basement boy. It was cold and wet last night and clothing or blanket would be too much for a miserable maggot like you. The only comfort you get is the painful swelling you'll feel while cock caged, shackled, bound, gagged, and blindfolded from smelling your Mistresses cunt! Don't be sad, I've brought you a gift of a shiny new toy and you'll be happy to know it is playtime. Thank your evil Goddess. This custom made film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. FemDommy KeyWords: Rosie, Painted Rose, PaintedRose, Goddess, Mistress, MommyDomme, Domme, Femdom, FemDomme, Sex, XXX, POV, Taboo, Taboo Sex, Roleplay, MILF, MILFY, Fetish, Depraved, Perverted, Kink, Suck, Fuck, degradation, verbal humiliating. cum control, orgasm denial, cuck, cuck-son, cuckolding, delicious FemDomination, spitplay, spit, squirt, leash, collar, pet, puppy, slave, slave training, agony, degradation, humiliation, Ballgag, blindfold, leash, collar, buttplug, humiliation, cum slave.

^$14.00 Add to Cart

The Pretend Fuck: Report Card Reward HJ 2 video from PaintedRose

The Pretend Fuck: Report Card Reward HJ 2 You are surprised when Step-Mom says you can have a reward for such a good report card and so you tell her you'd like a strip and for her to dance in her lingerie for you. At first, she says NO WAY! She offers some other ideas but you tell her that's the one thing you really want. Mom agrees and after she does it, she seems to loosen up a little from her normal prudeness. Mom tells you she feels bad because now you have this erection and she says she JUST CAN'T have sex with you even though she wants to because now she is turned on from watching your body. Mom has an idea, a handjob but you have to close your eyes and pretend that she is fucking you! Are you're eyes still closed? Do you feel Mom's warm, wet pussy sliding down on your stiff cock? Do you want to come inside my pussy son? Thank you For This CUSTOM video! Stepmom Fetish POV Handjob with imagination dirty talk to simulate real fucking. Don't peek lol :)

^$12.00 Add to Cart

Eat It For Goddess - CEI Drip video from PaintedRose

Eat It For Goddess - CEI Drip You've never wanted to please your Goddess like this before but you're lacking the confidence and need some loving guidance and motivation to go through with it. You want to please Goddess don't you? You can do anything we set your mind and Mistress will instructs you in the art of submission. Painted Rose Films and content is 2257 Compliant Fantasy Roleplay - Curvy Taboo Femdom MILF ROSIE! #CEI #CumEatingInstructions #Cum #Femdom #CumPlay #MILF #Goddess #SubmissiveTask #Mistress #Edge

^$7.00 Add to Cart

ToosDay BoobsDay Chillax With Step-Mommy Rosie video from PaintedRose

ToosDay BoobsDay Chillax With Step-Mommy Rosie It was a super long day today wasn't it? My day was good and how was yours honey? Is it ok if I undress in front of you? I got some new panties! The satin pajamas feel so good on and I am so sick of this tight bra and jeans. You can get your PJ's on too. Let's cuddle? I also want some kisses and I hope you also like Step-Mommy really close to you like this. Oh did you see that? My Titty accidentally fell out. You didn't see anything did you? Oh you did?? Uhmmmmm well I see you have a hugenormous boner - a stiffy !! Ooops, now I am horny too. Well.. we shouldn't be doing this but Step-Mommy can't help wanting you.. Do you want Step-Mommy too? It's SO TABOO. I Love YOU! Painted Rose Films and content is 2257 Compliant Fantasy Roleplay - Curvy Taboo Femdom MILF ROSIE! #TIts #Ass #Pussy #Boobs #MILF #StepMother #StepMom #Roleplay #DirtyTalk #Taboo #Sex #Blowjob #Creampie #Femdom #Findom #Dommy #StepMommy #Custom

^$7.00 Add to Cart

Becoming Her Man - Taboo StepMom Roleplay video from PaintedRose

Becoming Her Man - Taboo StepMom Roleplay You're getting older leaving for college and stepMom is getting hotter and sweeter. You've really bonded as she has devoted her prime years to only raising and loving you and you can't help but notice her body with all of your raging hormones and primal urges. Since you and Mom have been working out together, doing yardwork together, and hanging out a lot - you're just the best of friends.. 2257 Compliant Roleplay Fantasy.

^$13.00 Add to Cart

Anything For My Son video from PaintedRose

Anything For My Son Good Morning - How about coffee with Step-Mommy this morning? First of all, what is your Mom wearing and why is she tempting you without a bra on! Doesn't she know what she's doing? Of course she does.. In between accidentally seeing eachother naked and hanging out together, your sweet Mommy is making sure that you won't want to ever leave home. Step-Mom Taboo Fantasy Roleplay Scenario, Nip Slips, Masturbation, Love-Lust, Doggy style, Missionary, Cowgirl both ways. Doggystyle followed by Mom On Top back to back cums with dripping pull outs. Anything For My Son - A Rosie Original!

^$15.00 Add to Cart

Pantyhose Therapist: Impotence Testing video from PaintedRose

Pantyhose Therapist: Impotence Testing You have not been able to maintain an erection with your partner lately and decide to see a professional. You schedule your first session with a guidance professional who specializes in male impotence and sexual health who will perform several tests on you to determine your overall sexual health. For the testing, you undergo Rosie putting you through the ringers as she uses her seducing skills to determine your virility, endurance, and stamina. What's the verdict? This is a POV roleplay fantasy involving seamless pantyhose, mind fuck, mental manipulation, virtual sex and cheating - ooops. Thank you!

^$12.00 Add to Cart

MommyDomme Initiation Sub Training video from PaintedRose

MommyDomme Initiation Sub Training Step-Mommy found out that you didn't dump that girl at school. Surprise - Homeschool. Lies - Filthy lies step-Son and now I will punish you as your MommyDomme Bitch Mistress and train you into submission. You will regret letting that girl turn your Sweet-Mommy into a MommyDomme Bitch - I promise! Stripped. Penis Whipping. Ball Gag. Handcuffs. Buttplug. Tease and humiliate into an erection. Another penis spanking. Caged into chastity. The real training begins now! Thank you for sponsoring this film my 'Feeble' friend. Rosie's Cum Free Relapse Addict Fee: $100. Double Each Time You Come Back! Rosie's Drip and Cum Tax: DrippyBitch=$10, Jerkaholic=$25, Pussy Free=$50, Chastity=$100! TIP + Message to THANK ME for it.

^$14.00 Add to Cart

Cherry On Top: Step-Mommy Takes Your Virginity video from PaintedRose

Cherry On Top: Step-Mommy Takes Your Virginity Step-Mommy noticed you seem to be sad and were also really hungry at dinner. Dessert is in order - a sweet treat to brighten your day. You confide that you're having a lack of luck with girls and are still a virgin and StepMom comes up with the idea of a little roleplay so that you can practice. The roleplay went so great that as you sealed the deal with a kiss - BOINK! Do not worry, All boys have crushes on their Mothers and maybe I have one on you too. Must have been how sexy and sweet you are or maybe it was the kiss! Maybe and just maybe we've wanted this forbidden filthy talking first fuck all along. It's ok if we are just practicing to get you more experience with girls - don't worry. StepMommy gives you your first blowjob but you're still hard after cumming and so you slide into her forbidden fuck hole for a creampie filling so sweet that you're still hard as a candy cane for her. She decides to take your Cherry ON TOP and cowgirl rides you until she cums on your hard cock repeatedly. Still hard? Feed me that cock milk and glaze her cupcakes with your sweet creamy good boy goo. I Love You. This is a Rosie Original that is 2257 compliant and a solo performed fantasy roleplay. #MILF, #Femdom, #Goddess, #GentleFemdom, #Mistress, #PositiveFemdom, #Sensual, #FemDomme, #Tits #Ass #Pussy #Rosie #PaintedRose #StepMom #MILFRosie #Mommy #Taboo #Dommy, #MommyDomme #Blowjob #Creampie #BigAss #BigTits #BigBoobs #DoggyStyle #Cowgirl #CumOnTits

^$22.00 Add to Cart

Sensual Heel Dangling: Foot Worship JOI video from PaintedRose

Sensual Heel Dangling: Foot Worship JOI I am going to seduce you with my feet and heels very thoroughly. I love provoking your senses with my feet, legs, and my whole everything. Sexy lace pointed toe heels and feet worshipping for a powerful mutual orgasm. This is a shoe dangle, Arched Soles, Pedicured Toes, Heels, Barefoot, POV style, interactive foot, leg, toes worship with a JOI - like mutual finish!

^$12.00 Add to Cart

CEO Mom Shrinks Son: Wardrobe Assistant video from PaintedRose

CEO Mom Shrinks Son: Wardrobe Assistant Boss Mom calls you to her office to discuss your 'Promotion' because the current position just isn't working out. Boss straightens out your attitude real quick and then promotes you to Senior Executive Wardrobe Assistant! Snap a picture - oh it isn't a photo - it is a shrinking app! Boss Mom shrunk you to be little so she can place you in small places to examine her worn panties and get really close up to private places. Your first assignment is to help Boss Mom pick out a swimsuit for the company BBQ. You decide to try your best and do well in your position. Boss Mom tells you not to peek when she is changing. Of course you didn't look, right? Thank you for this custom video!

^$12.00 Add to Cart

Cuddles, Curlers, Cum With Gran-Mommy video from PaintedRose

Cuddles, Curlers, Cum With Gran-Mommy You find Gran-Mom (Older Mom) resting and snoring in her bedroom and want to cuddle. You climb in and curiosity gets the best of you as you lift up her big nighty. Gran-Mommy is curvy and naked under there! Upon awakening, You get gently scolded and talked to and Gran-Mommy says if she is gonna be naked, you are too. While suckling from granny's breast, she begins touching you and then tells you to lay down as she gently mounts you and begins to ride. Am I too big, am I hurting you Son? This is a POV first time, MILF GILF roleplay. Thank you!

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About Last Night: Forbidden Filthy Fucking Mommy video from PaintedRose

About Last Night: Forbidden Filthy Fucking Mommy My Wettest Mommy Fetish Movie To Date - a Rosie Collaboration and Creative Cum Conquest in this 3 part seXXX crazed bundle. 10 minute prelude, 2 hour movie, 20 minute Bloopers and extra scenes. From FORBIDDEN to FREE USE Filthy Fuck Fest! So Much Sex and Cum. Your Feature Presentation! Please DM after purchase if you would like to download this movie in 4K. (Too large for upload here). You've moved home with Step-Mom after going through some life changes and she could not be happier to have her sweet favorite home again. You notice she's struggling with her zipper and are ready with your big strong hands. What is she wearing? It's a see through top and gorgeous lingerie underneath. You don't mean to notice how hot she has become - is this the same woman who raised you? She invites you on her business trip and upon arriving find out that there is only one bed. She assures you the bed is big enough for the both of you and goes to get changed. You catch a glimpse and can't believe as your cock gets instantly hard and won't go back down. You're nervous when she climbs in bed and wants to kiss you good night. What the hell is she wearing to bed? Did she do that on purpose??? A sexy silk nighty and where did those tits come from. As she is tossing and turning her tit falls out of that too tiny nighty and then her ass swiped accross your engorged, dripping dick just as she awakens and grasps onto it with a firm grip. She thinks you're not awake and jumps up to run to the bathroom. What happens next is a forbidden filthy fuck fest of fornication. This Rosie collaboration film is a taboo POV roleplay with sex throughout the entire film. Multiple sex scenes with lots of wet sloppy slurpy blowjobs, her on top, you on top, sexy lingerie, undressing scenes, really forbidden dirty talk, shower scene, car blowy scene, doggy style - cum on ass, tit fucking and cumming, Close up female orgasm, cumspray, facial cum, tit cum, cum play, cum hungry, pussy play, upskirt, heels, daydream sequences for extra fun, bonus scenes and behind the scenes, ass twerking on your cock and cum cum cum cum and more cum! Painted Rose Films and content is 2257 Compliant Fantasy Roleplay - Curvy Taboo Femdom MILF ROSIE! Hashtags: #Dommy #Creampie #Blowjob #Taboo #Missionary #DirtyTalk #PussyEating #Roleplay #MILF #Cougar #Femdom #Curvy #Step-Mom #Step-Mommy #Fetish #CustomVideo #GoodBoy #StepMom #Taboo #MILF_Rosie #Rosie #XXX #POV #Panties #Panty #Goddess #Dommy #MommyDomme #Movie #Porn #Love-Lust #A_Rosie_Original #MILFY #StepMom #PaintedRose #Painted #Rose #Sex #Titties #Boobies #Tits #Boobs #TitFuck #Cumbath

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Cub Meat: Cougar Step-Aunt Takes Your Cock video from PaintedRose

Cub Meat: Cougar Step-Aunt Takes Your Cock Step-Auntie arrives to go party at the cougar den with your StepMom but she isn't home. StepAuntie hasn't seen you in a while so she decides to wait and visit with you. She immediately begins smoking in your StepMom's house and doesn't care - even offers you to smoke with her as you're old enough now.. She starts quizzing you on secrets and asks if you've been with an older woman.. Do you like cougars? She confides in you how much she likes young cub meat and seducing young cock. This naughty talk leads to her stroking and sucking your big boner and then telling you to take your pants off and fuck her on our Mom's bed. Doggy, Cowgirl, Missionary - Don't you dare pull out.. Creampie!

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Seducing Son's Buddy video from PaintedRose

Seducing Son's Buddy Virtual Sex after Seducing Son's Best Friend.

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