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Showing 301-360 of 600 Results

Wet Willy Wanking: Suckling Mom's Tits video from PaintedRose

Wet Willy Wanking: Suckling Mom's Tits Step-Mom comes into the bedroom to find you sleepy on her bed and she starts to tuck you in. She's dressed in skimpy shorts and a see through tight t-shirt as usual and she knows it's making your wittle willy so stiff. Mom starts telling you how she sees you and your friend looking back when she breastfeeds. She admits that she likes knowing you touch yourself and get stiffies for her big Mommy tits! Storytime as Mom tells you to suckle on her nipple. Mom tells you to wank under the covers until she is curious and reaches under to wank your willy getting it wet with spit. This POV and interactive film is a Mommy fetish, Nipple and breast milk suckling, naughty horny cougar handjob, dirty talk fetish fantasy roleplay. Thank you for this custom video!

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Temptation: Your Own Mother video from PaintedRose

Temptation: Your Own Mother You innocently come to see Mommy because you need her and walk in on her doing something you've never seen before! She's touching herself and rubbing - you feel your private place swelling and so you start pushing it back down while staring at your own mother .. naked. All of a sudden she sees you and stops and is very startled. She explains what she was doing and that even if it feels good to touch yourself and watch her - that we must not do it. You ask why - because you are a curious boy and she says that's just the way things are but thinks that you're not doing it right and decides someone has to teach you. Mommy starts moving like she was before and then says you made her h-o-r-n-y and says she needs to.. fuck! Mom on top, doggy, missionary - Cum For Mommy finale. A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Blind Date: Mommy Needs A Fuckboy video from PaintedRose

Blind Date: Mommy Needs A Fuckboy Newly single Mommy is starting to date and so is her Step-Son. After some coaching from you, Mom decides she just wants to have some fun. She gets set up on a blind date.. and so do you.. Little do you both know, you have been set up to go on a date with eachother! After the shock, Mommy suggests you have a pretend date and you both laugh and go for it, why not? Before you know it, this pretend date feels really real - like the real deal. The deal is.. Shhhhhhh she says, "my Son can't find out, I want to sneak you back to my bed and fuck your brains out!" You both pretend to be strangers on a blind date with steamy POV lust, sex, dirty talk and the beginning of a naughty affair. A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Sissy's First Christmas video from PaintedRose

Sissy's First Christmas You're Mommy's Sissy Baby Good Girl who loves to be smooched on, cuddled, breastfed, and loved. Step-Mommy is a horny sweet cougar and gentle Dommy who is getting all ready for Christmas! It's Christmas Eve and so you have to get to bed shortly after your night night Mommy Milky. You're awoken by sexy Mommy and the sound of Santa's sleigh pulling away! You both run to the Christmas tree and decide to open presents right now! Excitedly you both open your presents to find unexpected gifts and instructions from Santa. I guess we made the naughty list in a nice way! This film features first time sissy training, MommyDomme's gentle but firm good girl slut training, dommy dick sucking, fucked by Dommy, Face Riding, Clitty Rubbing, Sissy-Gasm, Cum For Mommy! A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you! Please give this film a 5 star review, hearts and shares, follow and DM Mommy if you need me. Happy Holidays 2023!

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Homewrecking Cougar Neighbor video from PaintedRose

Homewrecking Cougar Neighbor Rosie has been having an affair with her very married and vanilla sex neighbor and spicing up his sex life by introducing him to different stuff when his pretty little wife is out of town with the fam. I call and ask my maintenance man neighbor to come over in five minutes. When he arrives, I am wearing not much more than fishnet tights and a collar. I am blindfolded and horny with a few sizes of dildos laid out. I tell him I've been bad. He rubs and massages my feet and body. He tickles my feet and sucks my toes. He moves down to my pussy and licks my ass, pussy, and uses toys on me until I orgasm! Then he puts a leash on me and leads me to his big dick. He has me suck his cock! Then I ask if I can fuck him and I ride him front and reverse cowgirl after he makes me squirt Gspot pussy juice to lubricate his cock. He fucks me hard doggy style and missionary and then cums on my feet! He fucks me more and cums again! I thank him. Introducing Prop Dick Guy Calvin. Thank you to Captain for his wonderful and naughty custom script!

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Little Cock Tease: And Denial video from PaintedRose

Little Cock Tease: And Denial I get home to find you waiting for me patiently. I can see your desperate gaze and know your every look begs me to put out your fire. I enjoy being a cock tease and every moment of your agony pleases me. Did I cause this painful erection? Awe Babe - I can relieve a little of the pressure. Just a little.. Thank you For This Custom Film.

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Twisted Torment: Submissive Slave Training video from PaintedRose

Twisted Torment: Submissive Slave Training You've been lured to your new neighbors house for a meet and greet. She can see that you're new to being out on your own and could really benefit from a Mother's guidance. She's a hot MILF and shows you her panties and so you're eager to get to know her. She has a present for you - a housewarming gift that she says you will really cum to love. Just then, she pulls out handcuffs and cuffs you to the chair which is bolted to the floor. She laughs and says it's just a game - she's obviously a twisted bitch, the kind that gets off on control. She says you lied about being too busy to accept her invitation and that you will be whipped for disobedience. She assist you to her lap where she spanks you repeatedly with a wicked laugh. You'll be controlled and kept in her cold dungeon - don't worry, you can earn a blanket. She has you strip down and laughs at your penis as she puts you in a chastity device to remind you that she controls your cock too. Your initiation and submissive training has begun. Your new mistress will break you until you serve Dommy with humiliating body worship with complete submission. This film features female domination and slave training, foot and ass worship, handcuffs, ball gag, cock cage and chastity, penis humiliation, cock and cum control, findom and task for slaves. You will submit to Mistress Rosie. 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.

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Mommy Girlfriend: Love.. Is Love Son video from PaintedRose

Mommy Girlfriend: Love.. Is Love Son Step-Mom comes home from work and tells you she interviewed for a second part time job.. because Dad left, she's going to really need you to be the man of the house and help out while she is working more hours. You love your Mom - she's the only person who is always there for you. You're very close... very very close. Mom gives you a kiss and it lasts longer than it should and you both give in to your lust and passion making love for the first time. You don't care if it's wrong - all you know is that it feels so right. This POV Style film is one of my fave on my naughty to do list.. A story of Love with kissing, a long BJ, Mom on Top, You on top, doggy, underboob, close up pussy, and some heavy romance. Thank You!

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Ms. Flowers Pants Problems - ENF video from PaintedRose

Ms. Flowers Pants Problems - ENF You arrive to your tutoring session to find Curvy Ms. Flowers having issues with her pants during the class. She is sweetly embarrassed as the pants fall down repeatedly to the ground. She asks you to look away if it happens and you try to but it's hard to focus and you do enjoy the view. Next day, you're late so you need to take the test make up after school. Today her pants are unable to button and she squirms and fidgets with her pants trying to keep her exposed thong out of view. She suspects you are touching yourself and starts being not so nice and sweet. You don't pretend to look away which only makes her upset with you. She catches and scolds you looking multiple times in this Embarrassed Nude Female Exposed Panty Custom Film! Naughty Boy! Thank you!

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Sweet Dreams: Taboo Titties video from PaintedRose

Sweet Dreams: Taboo Titties As you arrive home from school, Step-Mom has just gone bra shopping and asks for your male opinion about which bras look and feel the best. After seeing her modeling her breasts in the bra's, you can't get the images out of your head or your dreams! Titty teasing continues in and out of your daydreams and restless nights for days with different bra's and sexy scenarios of booby rubbing, bouncing, nippy slippy, jiggly wiggly juicy jug hugs around your stiff dick. Finally Step-Mom decides to put that stiffy to rest by teasing you with a tit fuck /cowgirl ride as she fucks you with her tight MILFY pussy draining your balls with underboob bounce until you beg her to take your cock milk!

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Mom's Granny Panty Prank: Satin Fuck video from PaintedRose

Mom's Granny Panty Prank: Satin Fuck Your Stepmom gets home and she asks if you want to hang out since Dad is out of town and of course you agree. Mom gets the bed cleared off by hanging up her piled laundry and each time she passes by you to go to the closet, you pants her and reveal her satin granny panties - which you love! She warns that you're gonna get a payback and when she does, she finds out that you're not wearing underpants and that you also have a stiff dick. Mom is embarrassed and so sorry for doing that to you. She offers to let you fuck her as an apology. She tells you not to cum inside while she rides your cock DoggyStyle. The satin panties touch your cock while she's fucking you and you explode inside - ooops. Thank you for this custom video!

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Make Cummies For Mommy video from PaintedRose

Make Cummies For Mommy You're standing there when Step-Mommy walks out of the bathroom naked and get a special feeling in your pee-pee. Mommy says you need to talk about it - that you're a very good boy and did nothing wrong at all. Sweet Mommy explains about her body, your body, and all about pee-pee boners and masturbation to make your little stiffy stop hurting. She's worried that you're not making cummies but in pain so she pulls out her big milky Mom tits and gives you pee-pee kisses, licks, and sucks. You like it a lot and still don't make the cummies and so Mommy takes off her pants and teaches you about sex... it feels so warm, wet and good and Mommy says she's cumming on your cock and then says she wants you to make cummies in her hungry mouth. You nod and do as she says and make cummies in her mouth - so much in fact that it drips all over her bouncy boobies. She starts rubbing your yummy cummy all over her tits and then tells you to have a taste of her mommy pussy. She starts rubbing it and then quirts all over your face and mouth. You lick it up like a good boy. A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Slave Sandwich: Hungry For Humiliation video from PaintedRose

Slave Sandwich: Hungry For Humiliation Right on time for your Goddess servitude and humiliation task. Today I'd like to reward you for always doing anything to please your Goddess. Today I will make a a sandwich - a slave sandwich! Oh - don't thank me just yet. I'd like you to watch me prepare it and of course I will feed it to you. You'll be enjoying the most flavorful piss, cum, feet scrapings, snot, and spit delicacy to please me. I am so proud of you. Thank you for this custom film.

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You Didn't See My Butt Did You? video from PaintedRose

You Didn't See My Butt Did You? Step-Mommy is putting away laundry and then doing jumping jacks in a bikini and she just can't keep her bottoms up. You didn't see my butt did you?

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Bikini Stripper: Face Fucking MILF video from PaintedRose

Bikini Stripper: Face Fucking MILF Rosie teases and sensually and erotically strip dances, face grinds, and rides for you in this blue shiny bikini. Thank you For this custom video.

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Step-Moms Sin-Our Pervy Pantyhose Passion video from PaintedRose

Step-Moms Sin-Our Pervy Pantyhose Passion Step-Mom's wears pantyhose everyday and you can't stop staring, getting turned on, and stroking with her hosiery. You get caught with a full hard on at Sunday school and the teacher calls home about this. When Step-Mom asks you about it, you confess your love of her body in pantyhose. Later she catches you with her pantyhose and then asks you to come into her room. She tells you how it's not your fault.. you got this from her! She has a kink for hosiery and that it has to be kept a secret dirty desire between the two of you. A week of you and her playing with hosiery together leads to her ripping a hole in the crotch of seamless nude pantyhose and fucking you before church! POV Step-Mom Roleplay Fantasy, cheating housewife, religious fucking sin, taboo passion, and creampie fills her sweet lust hole. Thank you!

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Caught Perving: Taboo JOI and Rosie Squirts video from PaintedRose

Caught Perving: Taboo JOI and Rosie Squirts You've been caught perving with Rosie's panties and sex toys. She asks one question. Why? She laughs and tells you it's taboo - it's forbidden and that you need to learn what those sex toys are meant to do to a woman's pussy. How they smell, taste, and feel. Pull that dick out, NOW! Show me how you stroke. Do it like I tell you. Watch me with this toy, like how I fuck it? I can't fuck you but, I can make you CUM. Don't cum yet, make this edge last. When I squirt, You may cum too. Can you squirt me with it?

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Mom's Granny Panties: Cum Lube For Dad video from PaintedRose

Mom's Granny Panties: Cum Lube For Dad Step-Mom comes home from a day at the office and you talk about your day and that Dad is out of town. She begins to undress - in front of you and asks you if you mind. Mom tells you that her Granny Panties cover more than most bikini's anyway and that she just loves how comfy and silky they are. Mom says that after she cleans up the room, that you two can cuddle and watch a movie since Dad won't be here. As she's cleaning and you're watching, you decide to prank Mom and pants her - you really just want to see her backside. Mom does not think it is funny and warns you to not do it again - or else.. and so what do you do? You do it two more times until Mom is fed up - she pranks and pulls your pants down. Mom is shocked at your big, erect penis and tries to look away. She is curious and realizes that you like Granny Panties! Stepmom can't just leave you with that erection and offers to show you her 'wet spot' her 'fuck hole' to help you relieve yourself because she didn't mean to turn you on. She gives you permission to doggy fuck her but, you have to pull out son. Son, don't cum in me... This is a POV interactive Femdom, Sweet Step-Mommy roleplay with playful pantsing, granny panties, and doggystyle creampie cum lube cheating housewife. Thank you for this custom video!

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Mom's Sissygasm Training: Panty Princess video from PaintedRose

Mom's Sissygasm Training: Panty Princess Step-Mom noticed you've been in her panty drawer and she gets to the bottom of it.. She already knows so you ought to tell her. You love the feel of her soft panties up against your skin and tiny little penis. She makes you put on a pair in front of her and tells you that is your punishment for being a panty princess. Mom says it all makes sense to her now. You're a girl! Her new daughter who must be trained to be a panty wearing sissygasming princess. Mom's going to use you to clean her sex toys and teach you how to have intense sexual pleasure as a girl. No more jerking off like a boy. You will play with Mommy every night and ... lots of surprises for you young lady. This is a POV Sissy, ass pussy, sissygasm feminization video roleplay.

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Weiner Spanking Your Bad Boy Boner video from PaintedRose

Weiner Spanking Your Bad Boy Boner Step-Mom tells you that you need to have a talk and you already know you're in trouble but you aren't sure what bad thing she found out about. This time it was improper boners and she says that you must be punished because she loves you and she doesn't want you to be a bad boy. Mom says she is going to spank your weiner so take it out right now! She spanks your weiner but it just keeps getting harder with each smack. Mom decides to try rubbing it - with her tits out as an experiment and takes pleasure in continuing to throw in some slaps - a little pain with pleasure. She feels bad for being so mean - sort of and tells you since this isn't working she's going to spank your ass - with her dick - her strap on cock! She tells you how you're going to like it because she is going to continue rubbing your weiner until you cum! This is an interactive POV CBT Step-Mommy MommyDomme Femdom roleplay fantasy film. Thank you for this custom video!

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Simply Irresistible: Serve, Simp, Send video from PaintedRose

Simply Irresistible: Serve, Simp, Send When you need to let go, I'll be there to be in charge and give you relief. I love using my body to take you deeper into the mind fuckery that rules your body's need to serve me as your Goddess. Serve, Simp, Send. With this send - If you'd like, message me to tell me all about your specific needs as a submissive. I also have a formal application for you. Pleasing me is pleasing you. Send. You're Welcome. Goddess Rosie Rosie's Thank You Gift Options: Serve Dommy. Sweet Boy/Girl= $5, Nice Boy/Girl=$10, $25=Good Boy/Girl, $50=Very Good Boy/Girl, $100=MILFY's Favorite Boy/Girl Submissive Servitude Leaky Loser=$15, Jerkaholic=$20, Pussy Free=$35, Chastity=$75, Premature Ejaculation $115, Relapse Fee $250! Sissy Lover: DrippyClitty=$10, SissyGasm=$25, Slutty Pussy=$50, Dommy's Slut=$100! Appreciation: SweetSub=$100 SizzlingSub=$500 Super Duper Sub=$1000 TIP + Message to THANK ME for it. You're Welcome Darling.

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Lucky Cucky Foot Fucky video from PaintedRose

Lucky Cucky Foot Fucky Coming home horny to Dommy again? Always and especially when I am wearing seamless sheer silk hosiery and teasing you with my curvy Goddess body and sensual moves. These pantyhose were your favorite? Well they are your best friends favorite now too. He destroyed them while you were gone as he tore them while fucking me. It's storytime Cucky! You'll earn an allowance to cum only on my feet after you endure hearing about how your bestie came over and over and in your Dommy Mommy. This pussy can only be cummed in by his cock. On your knees and assume the position. This is going to be agony and I promise you will love it. This film features cuck-son, taboo roleplay, femdom, mistress Mommy, ripped crotchless pantyhose, beta training, submissive task, jerk off instruction, female domination and gentle humiliation. 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.

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Holiday Masturbation Humiliation Gift video from PaintedRose

Holiday Masturbation Humiliation Gift Merry Christmas and Happy Holidays! Rosie has a gift for you and I think it's something that you really need - tissues and lube! You're so pathetic, did you think I was going to actually let you touch me with it? I'd rather fuck this candy cane - and I do.

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Cuckold / Bull Switch and the Wife Swap video from PaintedRose

Cuckold / Bull Switch and the Wife Swap Rosie and her Husband are a hot, older Alpha couple. They made a deal: Husband wants to fuck and cuck a younger more submissive couple by dominating YOUR wife. Rosie wants to gently dominate a sub male and have him call her Mommy. Unknown to Rosie, you have a very stiff and big beautiful cock. Rosie's husband is so jealous to share her but the desire to dominate a submissive younger wife was too good of a deal to pass up! The cucks on him though, you're big, thick, young, and hung! Rosie gives you hand and mouth service while telling you to call her Mommy and thank her for the opportunity to please her. She rides you from the back doggy style and front missionary. She cums loud all over your big dick making sure her husband will hear it. Then she seductively and passionately counts you down and orders you to cum in her. This is a POV style, Cuckold / Bull Switch roleplay with homewrecking, cheating, partner swapping and gentle MommyDomme virtual sex.

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Holiday Tease and Denial JOI Game video from PaintedRose

Holiday Tease and Denial JOI Game Rosie plays a little game called, "Rosie Says" and it is a lovely game where Rosie tries to trick you out of your orgasm with a holiday spin on Tease and Denial. Christmas edging and teasing playfulness, Can you outlast Rosie?

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Sinful Sleepover: Moms First Threesome video from PaintedRose

Sinful Sleepover: Moms First Threesome You and your best friend are home from college hanging out and having a pajama party like old times. Your buddy tanks out early and you over hear moans coming from his Mom's room. Later on - you run into Mrs. Flowers in the kitchen and she invites you to hangout in her bedroom since her son crashed early. You guys chat a little when she starts getting flirty. What the hell, she's practically falling out of her tiny nightgown and you see her nipples. Next thing you know, she's sucking your cock but tells you her son can not find out! You promise not to tell. You're going at it, oral sex, cowgirl, doggy-style and then your buddy catches the two of you. Mrs. Flowers keeps fucking you and tells her son NOT to tell Dad! She tells him to join in for keeping the secret. You and your buddy fill up Step-Mom's lovely mouth and pussy with cum! This is a taboo threesome with POV sex and surprise scenes! Thank you!

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Horny Cougar In The Forest: Chance Meeting video from PaintedRose

Horny Cougar In The Forest: Chance Meeting Cougar MILF and newly single Rosie runs into her son's friend while walking a trail. They decide to walk together because he wanted her to be safe and he's always been fond of her. He compliments her on how she's looking and says he's missed her. She is very fond of him and he says he's never dated an older woman. She notices his dick print in his pants - It's big and it's not even hard! Three miles later they start holding hands. Innocent enough but, not really. She's so turned on! He carves a heart in a tree for her and confesses how much he wants her. They start touching and she grabs his massive cock and bends down on the ground and blows him for a few while. She takes him bent over in a couple of positions and then he lays her back on a rock and gives her a donut glazing and creampie!

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Mom's Tease and Denial: Three Days video from PaintedRose

Mom's Tease and Denial: Three Days You had the misfortune of breaking both of your arms and Stepmom has been caring for you for weeks. You've had to recover in her room to have closer access to the bathroom and so she's been changing her clothes with the curtain pulled. Does she know you can see everything? She's always dressing up and going out and coming back to undress and cuddle with you. It's driving you insane with a drippy, stiff cock. Mom notices your boner and each day she feels so bad that you can't jerk off and that you're in pain down there. Mom tells you she might let you cum tonight but that she doesn't know because she's your Mom. She brings you to the point of dripping precum which releases pressure each day but hasn't decided if she should let you cum all the way. Each day, you are in agony over the cock tease, blowjob, and denial. This is a POV MommyDomme roleplay scenario. Thank you for this custom video.

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Impulsive: Lose Yourself In Mom's Kiss video from PaintedRose

Impulsive: Lose Yourself In Mom's Kiss You're my whole world Step-Son and I can't wait to be with you when I get off my hospital shift. Let's spend some time together - oh you make me laugh and feel like a girl again my handsome young man. After a long day out having a blast, neither of us want this night to end. The long looks, shy blushing, flirting and blurred lines being crossed accidentally and then on purpose. I invite you to hangout in my room if you get bored and I'm not surprised when I turn around to find you looking at me with a boyish look of hunger in your eyes. I won't keep it a secret anymore - my forbidden feelings for you and my desire to explore your body with my mouth and aching body. Breathless. This film is a first time roleplay fantasy (step) Mommy Fetish video with lots of close up POV sex, dirty talk, real squirting Rosie-Gasm and a dripping creampie CFM. A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you! Did I make you cum extra good? Thank me with the tip? Sweet Boy= $5, Nice Boy=$10, $25=Good Boy, $50=Very Good Boy, $100=Mommy's Favorite Big Boy THANK YOU!

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Giantess Rosie and the Shrinking Serum video from PaintedRose

Giantess Rosie and the Shrinking Serum Rosie and her assistant are working on a shrinking serum and when she gets to the office, he is nowhere to be found. Then she sees him, TINY! He's been working after hours and cracked the code. He wasn't suppose to test the serum on himself, but Rosie thinks he is so cute and tiny. She picks him up and congratulates him on how much money they are going to make. She gives him kisses and decides to play with him. She licks him and puts him in her mouth. He is getting mad, which she thinks is super cute! She loves being so big and him so tiny and wonders what he would feel like in her pussy. She uses him to pleasure herself until she has a wet orgasm and little one is covered in her cum. He is NOT HAPPY. He asks again for the reverse serum...She realizes he's gonna be trouble for her and decides if he isn't around, she will keep all of the profit. She has an idea and tells him it will be quick and painless but, the serum has made him almost indestructible. Almost. Custom Video.

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Mom Does It Better Than Your Girlfriend video from PaintedRose

Mom Does It Better Than Your Girlfriend You bumped your head and go into a dream state and have a hot fantasy about your nurse stepmom. She wakes you while wearing a seductive outfit unlike her normal work scrubs and just when it's getting good, you are awoken by Mom in her regular scrubs. You tell her that you bumped your head while getting ready for a date with a girl. She realizes that you're not acting normal and does a full investigative exam on you and your penis - just to make sure everything is working as it should. Mom tells you she knows your body very well and how it works and bets she can make you cum faster than you jerking or fucking your girlfriend. Mom makes you cum three times! Too bad there is nothing left for your girlfriend. Bonus scenes at the end. POV Femdom MommyDomme Fetish, Nurse, Cheating, Taboo, Medical Fetish, MILF, Curvy, Mature.

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Impregnating Your Mother-In-Law video from PaintedRose

Impregnating Your Mother-In-Law Rosie, your Mother-In-Law, looks at her Step-daughter and her Step-Mother's sonogram pics and wishes she was pregnant too. She suddenly realizes that you're probably responsible for both pregnancies and comes up with a plan to seduce you into sex guessing that you love filling fertile pussies and making women pregnant! During seduction it's all about the fuck but, once your inside her 'Step-Mommy Pussy' the dirty talk is all about making one big happy house and keeping all three pregnant and properly filled with your fertile seed at all times! This vide has Cheating, Impregnation, Step-Mom, Breeding, Taboo, Pregnant, POV Sex. Thank you for this custom film!

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Boy Next Door: Daydream: Don't Cum In Me video from PaintedRose

Boy Next Door: Daydream: Don't Cum In Me The boy next door sees his MILF neighbor checking her mail and he begins to daydream. He goes over and knocks on the door to pick up a tshirt that his mom bought.. (A tie dye that Rosie made). Rosie thinks he ought to try it on to be sure it fits. Rosie immediately begins to seduce him by rubbing his arm and touching him. She tells him that she saw him looking in her window with binoculars. She told him she wouldn't tell. She begins to ask him why he was looking and if he liked what he saw. She continues to make him feel uncomfortable by touching his hard penis. He is afraid his Mom will find out. She swears not to tell. She tells him, "Just don't cum in me" She blows him and has him pull he jeans down. He sticks his massive dick inside and fucks. She praises his efforts and tells him how good he is doing. She lays on the bench and he begins to fuck her harder and faster...Then...

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Grounded: Earning Mom's Ungrounding video from PaintedRose

Grounded: Earning Mom's Ungrounding You got yourself grounded you naughty boy and now you need to get Step-Mom to let you free for the weekend before Step-Dad gets back from out of town. Step-Mom says you could earn ungrounding if you do something for her to make it worth it to go behind Step-Dad's back.. You come to an agreement, Step-Mom needs dick and you need pussy - it will be a Hot and Hard weekend! Step-Mom seduces you with her body and says she will teach you to do dirty sex. Sloppy Wet BJ, Ass tease, Doggy Style, Step-Mom fingers her pussy to squirt cum on your cock to make it really wet for your turn to missionary creampie her shaved, pink fuckhole. Cum For Step-Mommy. Thank you for checking out my film! Please message me if you have any needs at all. Thanks!

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Big Boy Bedtime Boner video from PaintedRose

Big Boy Bedtime Boner You and Step-Mommy are having a happy play day and after being outside you come in and then get changed. You walk in and see her in bra and panties but she quickly closes her robe and then you feel a funny feeling in your pee-pee. Step-Mommy thinks you must be afraid to go to bed in your room so she says after story time, you can go nighty night in her room. After the story it's tickle time before getting tucked in and Step-Mom sees that you have your first big boy pee-pee boner. She's really proud of you and gives it a kiss to make it stop hurting. Lots of kisses and then she shows you her panties and bra. You like it so she shows you her p-u-s-s-y and teaches you a dirty secret word and then how to do sex. You even get on top and show her what a big boy you are. You're my very Good boy! Step-Mom Roleplay Fantasy with Dirty Talk and POV sex with small dildo. Thank you for this custom Film!

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Class Boner Paddle and The Extra Credit video from PaintedRose

Class Boner Paddle and The Extra Credit Rosie calls you into her office after class to inquire why you have been skipping class! You're now failing for missing assignments. You admit it's because you were getting boners in class and tell her it's her fault for dressing provocative. She says there is no excuse and asks you what the consequence is for skipping. You already know it is five wacks. Rosie decides you didn't feel the test whack and pulls your pants down. She leaves a nice red mark and she turns you around to see if you're crying but, instead you have a boner. She says she is telling your parents that you're going to fail her class. You beg and so she says you can earn extra credit by giving her a taste of big dick. You also give her the hard fuck from behind that she needs and bang on her desk. She sends you back to class but, you can't go back with THAT DICK HARD so she sucks it and you cum in her mouth and all over her tits which she rubs all over her breasts! Huge Load of cum. Did you pass the class?

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Paid Loser Date: Findom JOI Humiliation video from PaintedRose

Paid Loser Date: Findom JOI Humiliation You bring Rosie in from the dinner date expecting sex, afterall you've paid twice this week for playdates and for tonight's dinner. Surely she is more than an escort. She seems to really like you. She had amazing orgasms and said you 'rocked her world'. You're running low on cash and so Rosie turns you down for sex and tells you that you're a paypig, human wallet with a loser dick. She continues to berate you for wasting her time and makes you take out your wallet and charge some sexy heels for her off of her wishlist, hand over the cash in your pocket, and give her your watch for ruining her night. She tells you to pull down your pants and start stroking and as a thank you for the shoes you can look at her tits and pussy. The punishment for making her ask for the money is that she berates you the entire time you're stroking off. She's so bored so she decides to play a JOI game. If you can shoot four feet and hit her shoes with cum, she will let you have the cash back. Can you do it? This is a POV and interactive Financial Domination Femdom JOI Humiliation.

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Heaven In Heels: Forbidden Pointed Heels video from PaintedRose

Heaven In Heels: Forbidden Pointed Heels Rosie comes in and wants you to help her choose which heels to wear. She seductively teases you to enjoy the view and gives you the blue pair to hold onto while she tries on the black. You both get so turned on that you cum together with the pointed heels. Thank you for this custom video. Pointed heel Shoe Fetish and High heel with a side of highly arched feet, Shoe smelling, MILF, Cougar, Heels JOI, and Seduction.

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Dirty Movie: Mom's Favorite Film video from PaintedRose

Dirty Movie: Mom's Favorite Film It's Step-Mom's turn to pick the next movie and she offers with Dad being out of town that you could watch something a little more adult - maybe even her favorite dirty movie. You're up for it and Mom wants to go down on you. She says that you can do to her what the guy is doing with his step-Mom on the XXX movie. After your first wet blowjob, you get schooled on fucking. Doggy, Cowgirl, Missionary Cum Inside. Ya.. Rosie totally planned this!! Dirty Talk. This is a roleplay fantasy scenario with Cheating MILF and Cougar Step-Mom Fetish. Thank you!

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Step-Mom's Maid Service: Cum Cleanup video from PaintedRose

Step-Mom's Maid Service: Cum Cleanup You're a dirty and messy boy according to Step-Mom and she's really grouchy about cleaning up your messes and insists that she is not our personal maid - blah blah blah is all you hear and then walks in your dream Step-Mom in a sexy maids uniform catering to your every need and uhm.. cleaning up your messes - with her holes! Finally she does something useful with that mouth. This is a step-Mom / Cougar Film with dancing, blowjobs, fucking, tit bouncing, ass twerking on your dick, and finally a blowjob swallow finish! Thank you!

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Delicious Cherry: Step-Moms Forbidden Fruit video from PaintedRose

Delicious Cherry: Step-Moms Forbidden Fruit Step-Mom tells you that she is going out dancing with Auntie and is dressed sexier than you've ever seen and models her outfit and heels for you to get your opinion. You get a call from her later on asking you to pick them up because they got a little too wild and watered. You are helping her to the bed and you get a little grabby because her tits are slipping out of her dress and she scolds you and tells you that you can't take advantage of the situation and she is upset with you but also realizes she shouldn't be dressed like this in front of you. You continue to try to get in feels and touches knowing she's horny and this is your only chance to seduce her. She gags and slobbers on your big hard dick after seeing your big boner and you fuck her tight juicy pussy and all the ways you've fantasized about. She yells at you to pull out before you cum so you spray your load on her dress and face and then she eats the cum off you stiff one. HD/4K. Thank you for this custom film.

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Mrs. Flowers Favorite Step-Son video from PaintedRose

Mrs. Flowers Favorite Step-Son You're spending the night with your buddy and things aren't so great at home. Mrs. Flowers tells you that you can stay forever as long as you are a good boy and agree to the house rules. Behave, Do as you're told, and come to Mommy's bed when her husband is out of town. You're her new favorite son but it's a secret just between us. Subtle flirting, secret glances, burning desire to sneak passionate fucking now that you're the fave. You get to spend the night in Mommy's bed tonight and I'm going to teach you how to fuck this Mommy pussy boy. Step-Mom Taboo Roleplay Fantasy with MILF, Cheating, Blowjob, Squirting, Doggy Style, Twerk on Dick, and a Cowgirl Creampie! 2 Cum Scenes for you in this Rosie Original!

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MommyDomme's Sissy Lesbian Lover Training video from PaintedRose

MommyDomme's Sissy Lesbian Lover Training It's really strange that my lingerie company sent me a maid's uniform by mistake, isn't it Son? I am not so sure it was a mistake because I've noticed some things going on with your behavior lately. You're going to try this on for me, it just happens to be YOUR SIZE! I will be punishing you in all sorts of ways for lying to Mommy. You will clean on your hands and knees in this maid's uniform and when you finish all of the chores, you will begin your training to be my Sissy Lesbian Lover! First things first, you'll wear this clitty cage so that you stay focused while you you do your Cinderella chores. Feminization training for a sissy slut begins with a Dommy Dick Sucking Lesson on your knees young lady. POV, Oral, Strap-On Sex and more surprises! Thank you to Wolfie for sponsoring this very Dommy Film. Rosie's Thank You Gift: Serve Dommy. Sweet Girl= $5, Nice Girl=$10, $25=Good Girl, $50=Very Good Girl, $100=Mommy's Favorite Girl Submissive Servitude DrippyClitty=$10, SissyGasm=$25, Slutty Pussy=$50, Dommy's Slut=$100! TIP + Message to THANK ME for it.

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Dump Your Girlfriend For Mom's Creampie video from PaintedRose

Dump Your Girlfriend For Mom's Creampie Stepmom is calling you because you're late...the third time this week and wants to know where you have been. Through questioning, Jealous Mom finds out you have a girlfriend! You don't need a girlfriend son, you have me....I can do anything she can do...better. Dump her son...and I'll fuck you, I'll give you your first blowjob. I don't want to lose you to her......Mom get's sensual and turned on telling you how much she wants you. She sees you're hard and takes it...She slow teases and sucks you with a wet sultry blowjob and ask you if you'd like to try doggy style. Next you bend her over and she has you give it to her from the back. That's Mom's good boy. You climb on top of mom and give her the creampie filling that she's begging for. POV Stepmom First time. Mom's seduction.

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Cheating Spouses: A Passionate Affair video from PaintedRose

Cheating Spouses: A Passionate Affair I met you when you began delivering packages and so I kept ordering more so that we can keep having excuses to have lusty, dirty wet sex while our unknowing spouses continue ignoring our needs for passion. It's been going on for months and today my husband walks in and catches us but we keep fucking. Nothing will stop us from being together.. especially your wife. You leave your door unlocked so I can sneak over with only lingerie under my jacket and fuck you while she snores next to us. My moans and rocking that dick wakes her and I tell her to watch while we fuck and breed our primal passions. This is a POV, Cheating, Roleplay with Blowjob, Sneaking, Caught, Reverse Cowgirl, Her On Top, Creampie Breeding. Thank you for this custom video!

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Mommy Date - Get Mommy Pregnant Again video from PaintedRose

Mommy Date - Get Mommy Pregnant Again Mommy loves to spend time with you and she hopes she got pregnant the other night but, just to be sure...let's try again. Mommy loves you and how stiff you are. I love feeling you inside throbbing and getting ready to fill me up with sperm. Mommy loves you! POV Virtual Sex.

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Satin Passion: Mom's Horny Honeymoon video from PaintedRose

Satin Passion: Mom's Horny Honeymoon Step-Mom and Dad just got married and they took you along on the honeymoon. You're relaxing and minding your own business when Dad's new wife comes to you're room to see if you're still awake. She says Dad is not awake and you can't help but notice she is wearing a satin nightie and thigh high's with lace trim. You instantly get hard! Dad is suppose to be banging this HOT MILF but he is snoring...Mom asks if you want to touch the satin fabric and then she starts to wrap the fabric around your hard dick and jerk you with it! It feels amazing and then she blows you long and wet. You love it and then she says she wants you inside of her. She sits right on your cock and her pussy is warm and wet. She bounces a bit and then leans back so you can see her pink clit swollen on your shaft. Then Mom Teases you with her body and ass. You want to fuck her hard and she tells you not to worry and just bang her raw and make her tits jiggle and so you creampie mom and she kisses you for it. She asks you to keep it a secret from Dad so you guys can keep doing it! POV Virtual Roleplay.

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Hot For teacher - She's So Mean 4K video from PaintedRose

Hot For teacher - She's So Mean 4K (CV) You're interrupted for your horny boy daydream by Ms. Flowers smacking a ruler in your face and humiliating you in front of the classroom for not paying attention and getting an F in her class! You're inlove with her and enjoy her being mean to you as it makes your big boy boner ever harder everytime she scolds you. You go to her house to make up the test but instead you pop the question with a 3 carat diamond and offer all your money and servitude. She could have anyone she wants and she wants a hubby who will pay all the bills, worship her body, and make her a spoiled stay at home Goddess Mommy. She tells you to impregnate her now and if you make her cum, she will agree to your proposal. POV includes teasing, humiliation, blowjobs, doggy style, cowgirl and reverse, missionary dripping "breed me" creampie. Thank you for this custom video. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Tired Feet: Hose Footrub JOI Countdown video from PaintedRose

Tired Feet: Hose Footrub JOI Countdown Getting home from work with tired sore feet and the one thing that always makes me feel better is your foot rub. Your strong hands rub and massage through the hose. You like how I spread my toes and paddle my feet back and forth in front of your face. You love the smell...a lot. When I see you getting hard I tell you to focus on the smell and kiss them and use your hands on your dick now. Stroking for my feet. I countdown. 10...9....8........This is a custom video.

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Confessions Of A Cock Loving Nun: Boy Cum video from PaintedRose

Confessions Of A Cock Loving Nun: Boy Cum Confessions Of A Cock Loving Nun: Boy Cum. Forgive me Daddy - I've been a BAD GIRL. Sister Rosie confesses that she has been tempted into lust .. again. She's wearing sinful lingerie underneath of her clothing and begins touch herself after dismissing the Sunday school class. Her favorite student comes back and catches her and he gets his first penis erection and is scared and sister Rosie panics and touches his pee-pee and then calms him down with a cummy little cock handjob. She then prays and masturbates to the thought of his cute cock and messy cum still on her hand. She decides to pray and repent but the next day - he has another erection and.. The temptation of the flesh is too strong and they give in to lust with a playful handjob, sexy fellatio, horny little cock ride, and finally an open mouth cock milk dripping spray in her cum hungry mouth. She lovingly tells you that our sins are washed away.. if we just pray. Forgive me Father.. Thank you - A Rosie Original.

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Peeking Perverts video from PaintedRose

Peeking Perverts You can't help notice your Step-Mom's curves especially when she walks around in short skirts and push up bras all the time. You know it's wrong but couldn't look away when you woke up early one morning and she was in the kitchen in her hot little panties and bra. Does she know what it's doing to you? You're beginning to think she's doing it on purpose!! She loves the carrot cake you made for dessert and so she serves you up some pie - well pussy pie.. and tells you how sweet "Mommy Cunt" is! She tells you that she sees you looking and maybe she's been doing it on purpose and walks away with a smile. Later on, she practically bumps into your boner coming back to from making some tea - she's having insomnia and so are you. You can't believe your ears when she says she loves giving blowjobs and she doesn't want you to have to keep masturbating alone. She's horny too so she says you're going to learn how to tongue fuck pussy and fuck. You're Mom's Peeking Pervert now. This film features Step-Mom roleplay fantasy, Taboo Dirty Talk, Seduction, Loving Kisses, Sultry Sex, Doggy Style, Missionary, Blowjob with cum spit facial, Pussy eating, Cowgirl dick riding close up and full view with underboob and a dripping cream pie. A Rosie Original.

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Package Delivery: Curvy MILF Raw Fuck video from PaintedRose

Package Delivery: Curvy MILF Raw Fuck Package Delivery: Curvy MILF Raw Fuck - Busty MILF Rosie and the delivery guy. I am trying on lingerie when I hear a knock at the door, it is the delivery guy. Right on time! I get a lot of packages but this is a new package delivery guy. He's nice and tall and tells me that he has a heavy and large package for me. Hmmmm how convenient. I ask him if he can bring it in to me since it is so big. Positioning myself on the bed, I apologize for being scantily dressed but, of course he doesn't mind. Chit chat leads to flirting leads to skipping the first and second date to get right to the third date and finding out about that dick. I get right to telling him I want to see his whole body. It's been months since I've had a man after my divorce and I'm starving. What is under those work pants? I can't believe my eyes and get right to slurping on it. Then I back my ass up on that dick for some doggystyle and more sucking. Some reverse cowgirl and cowgirl is definitely what Rosie ordered! The delivery driver has some skills of his own banging that pussy and making me squirt the entire bed and floor with some G-spot finger banging! He licks it up like a nasty dog hungry to get his cock off. Lots more blowjob and him on top until he's ready to cream pie me...not just once but he pulls out to cum on my clit 5 times up close. I tell him I will order more packages if he promises to deliver...and he agrees with a smile. This video combines POV shooting with Story mode filming in HD and available in 4K.

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Dildo Saleswoman: Indecent Exposure video from PaintedRose

Dildo Saleswoman: Indecent Exposure A day in the life of Rosie the dildo saleswoman. She starts off in the morning sunbathing and then gets ready for her third day on the job. She started as a dildo saleswoman and so far had not sold any and so today she has some new demonstration ideas. She pulls out all the stops and sells the whole box after sucking and riding each one for a woman's husband. She gets a call from her boss who then fires her saying she has not sold enough dildos and that she can't use her cleavage and unprofessional methods to get the sale. She is upset but gets an attitude and tells her boss to fuck off. Then Rosie confronts her husband as she knew he would start a fight with her over her losing a job so instead she kicks him out. She doesn't need a man and so she gets out a sex toy and has a delicious orgasm. Just then, the phone rings and it's a job interview. She rushes off and tries to use her body to seduce the interviewer into giving her the job. Do you think Rosie gets the job? POV Femdom Gentle, Goddess, Cleavage Fetish, tease and seduction.

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Little Step-Sisters Keeper: Tits and Ass video from PaintedRose

Little Step-Sisters Keeper: Tits and Ass Newly divorced Rosie asks her older Step-brother if he can come and take a look at her work tablet. They are very close and he lives nearby with his bitch wife who doesn't appreciate him. He's arrives like always to assist his little StepSis. Rosie is dropping stuff and bending over, having nipple slips that she doesn't notice, and her lip gloss is bubblegum pink. He tries not to look and then she notices you noticing and you notice that she doesn't seem to mind. After you finish fixing the device, she confesses that you're both miserable and lonely and that her young crush on her big stepbro has never gone away. She asks why it's wrong and says she doesn't care because she needs you.. she leads you to her bed after planting one on your lips and offers you a slippery titty fuck. You do as your told and drop them like a good boy with a big stiffy. After the Tit fuck comes a wet blowjob, doggy style, missionary, squirting orgasm, a little cowgirl missionary with a dripping creampie! Lots of taboo dirty talk. Step-fam roleplay fantasy. Thank You For This Custom Film.

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Training Step-Mom's Free Use Pussy video from PaintedRose

Training Step-Mom's Free Use Pussy Step-Mom is always falling out of her clothes with her big tits and ass, teasing your dick when Step-Dad is not home. You can't take it anymore and decide your going to seduce her with your stiff young meat. You start by saying she made you hard and that you just need to see her granny panties to masturbate to. Then you ask to rub on her panties - she reluctantly complies. Then you say you need to see her butt.. and ooops you slide right in and fuck her while she scrubs the floor and fill her married MILFY pussy. You've been fucking her all week in random places and next you get her to suck your dick and take a pussy fill as step-Dad pulls into the driveway. Step-Mom comes to you saying she is worried about getting caught so you show her your big boner and she can't resist and asks you to breed her MILF pussy on Step-Daddy's bed! She is dick whipped and now you have trained this Free Use Pussy. Thank you for this custom film.

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Cum-Cakes: Special Recipe CEI video from PaintedRose

Cum-Cakes: Special Recipe CEI You've arrived to Rosie's kitchen for a baking and Cum Eating Lesson. You need guidance and motivation and Rosie is just the Mistress to help you out. She sensually and seductively guides you to cum in a glass while the cupcakes are baking. Tempting you with a taste of her pussy and boob flash on cumpletion of the class - Rosie has the ingredients she needs to finish up the icing on the Cum-Cake. Yummy! You can do this with Rosie's seductive motivation to eat your own cum. This is an interactive fantasy CEI roleplay. Thank you!

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MILF Rosie's Cummed In Panties For You video from PaintedRose

MILF Rosie's Cummed In Panties For You I have a present for you. It's my panties. First, I want to cum in them for you. I tease you with my body, lips, pussy. I stuff these hot red panties in my wet pussy and rub my swollen clit for you. I gently pull and tug on the strings while telling you how and when to cum for me. Message me about me mailing my panties to you...Get yours today!! I have a present for you. It's my panties. First, I want to cum in them for you. I tease you with my body, lips, pussy. I stuff these hot red panties in my wet pussy and rub my swollen clit for you. I gently pull and tug on the strings while telling you how and when to cum for me.

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Brownies For Dad: Son's Sweet Revenge video from PaintedRose

Brownies For Dad: Son's Sweet Revenge Dad won't let you watch cartoons - he's so grumpy and so Step-Mommy asks you to help her make brownies to cheer him up. Mommy looks around but, she is missing a special ingredient for the icing and asks you to help her. You don't understand how you can help and then StepMommy asks you to take your penis out and she starts sucking on it. Mommy keeps consoling you for Dad being being by telling you that you're her special boy and Dad is a meanie and we have to cheer him up with something sweet. Mom shows you her sweet spot and fucks you cowgirl and doggystyle and then strokes you into a cup to make the icing for Dad's Cum Brownie! I am so proud of you - let's go surprise Dad with this Sweet Revenge! This is an interactive POV Cheating Wife, StepMom Roleplay Fantasy. Thank you!

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Giantess Persuasion Ass-ignment video from PaintedRose

Giantess Persuasion Ass-ignment You've been detained and have resisted cooperation on the top secret project and so they have decided to call in Rosie, a psychoanalyst and world renowned chemist who has her ways of making men like you cooperate using her shrink serum to make you powerless. You've heard of waterboarding right? Being 'trained' into cooperation by Giantess Rosie and her Asstounding methods is pure torturous mind fuckery that even you will suc-cum to. Thank you for this custom film which combines Giantess, beta humiliation, feet / shoe / pantyhose toe play. Squashing and roughing up. Ass play and butthole winking (head first mostly for air depravation) and ultimately your complete cooperation or extermination - you decide.

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Teacher's Pets: Cuck and Bull Timeout video from PaintedRose

Teacher's Pets: Cuck and Bull Timeout Miss Rosie thanks your for the love note and flower and tells you that if you want to be her Teacher's Pet that she will have to see if your penis is big enough. After dropping your pants, she informs you that it's not big enough yet and that she has an idea to work with you and another student for some special tutoring. She calls her first pet back to class and it's obvious that she's infatuated with his ginormous dick and compares the two of you. Miss Rosie teaches you about what it will mean to be her Bull Pet and her Cuck Pet. She offers you special prizes for participating in this opportunity that you can't refuse. She attempts to see if you get bigger by sucking Big Boy's cock right in front of you while giving you permission to touch your little dick but not to cum quite yet. As she taunts you by praising Big Boy, she gets hotter and plays with her tits and pussy while blowing him until he cums in her mouth. She spits the entirety of his big dick juices into a little cum and tells you that if you want her to ever suck you that you will have to swallow his cum as a growth serum. She pours big boys cum down your throat and wanks you until you cum as a reward. You will be required to complete the cuck program to graduate to be her Teacher's Pet. This is a cuck and bull roleplay fantasy in a classroom scenario of favoritism, naughty puns, and submissive servitude. Thank you!

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