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Showing 121-180 of 600 Results

Stretch and Rub with Mom Afterschool video from PaintedRose

Stretch and Rub with Mom Afterschool Curvy Stepmom consoles you about your rough first day at school. She goes on to start her workout while you chat. She asks you to get behind her to help stretch her hips and you are happy to help. Mom feels something poking her that is hard and she begins to rub her butt in yoga pants on it. She tells you to pull your dick out and rub it on her butt through her yoga pants! She likes it and turns on her back to rub your dick on her clit and make herself cum. Then she tells you to hump her ass through her yoga pants until you cum! Virtual Sex POV and dildo used. Custom Video!

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Foot Worship Punishment: Rub, Suck, Lick video from PaintedRose

Foot Worship Punishment: Rub, Suck, Lick You are working for me and were careless with my priceless beverage glasses after I told you to please be careful. How could you be so careless? You know the crystal glasses will be coming out of your paycheck but, they were one of a kind and irreplaceable...unlike you. I don;t think you are sorry enough to keep your job. Oh you need this job? Ok. Come and get on your knees. Bow down and apologize. Begin to rub, smell, and lick between each of my toes. My feet are very tired and you are now my foot slave. Do you like how they smell and taste? I don't care just don't stop until I tell you to. Follow my every instruction. Are you sorry? tell me again. As I punish you.

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Toy Cleanup: Mummy Yummy Cummy video from PaintedRose

Toy Cleanup: Mummy Yummy Cummy Step-Mom comes in and sees the big mess you made and offers to help clean up and she's dressed different than normal - she is wearing her under clothing but different than normal.. like the ones you see in the magazines she keeps in the bathroom Cupboard. She tells you her clothing is called lingerie and asks if you know where her missing magazines are. You were a little naughty and put them under your pillow to look at but, Mom isn't mad - she says it's normal for boys to like looking at girls in little panties and bras. You're really enjoying watching her pick up your toys dressed like that and you get the same feeling.. down there.. like when you look at the magazines. Mom teaches you about making cummy and how to not be messy because she knows you're such a messy boy. Small Dildo used. First time POV Virtual BJ with sweet naughty talk. Thank you for this custom video!

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Mom's Road Trip Turns Into Sex w/ Son video from PaintedRose

Mom's Road Trip Turns Into Sex w/ Son Mom and son are on a trip to visit family and stop at a motel to rest. Unfortunately there is only one room with a shared bed. Mom and son are ok sharing, why not? Mom starts getting her pajamas out and finds old lingerie in the bag and her son convinces her to try it on. He asks to see. She is shy and embarrassed but he convinces her and takes pics to show her she looks fine. He touches her breast and she is shocked! HE then touches her pussy which gets her all wet. She tells him to get down and lick her. She gets so horny she blows his big dick. When he fucks her, she wants it rough. Doggystyle, oral sex, missionary...creampie! He cums twice!

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Teenie Tiny Dicklette - Mommy's SPH JOI video from PaintedRose

Teenie Tiny Dicklette - Mommy's SPH JOI Step-Mommy takes you to the pool for some sunshine and notices you don't quite fill your swim trunks. She thinks the other Mom's at the pool noticed too. I have you pull it out to show me and to my surprise, it's in inch...hard! Why are you getting hard for your Mommy? Is it really hard? Are you sure? It is too small to ever please a girl. You'll have to be Mommy's little masturbator. I want to see if it can even cum so stroke for Mummy like a good boy. That's it. Mommy will count you down from 5 so we can make this a cum game! After you cum, we will go get you some new swim trunks. Little tiny pink ones...Gentle Femdom, Mommy Fetish, JOI, JOI Games Countdown, SPH. Small Penis Humiliation.

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Giantess Loves a Little Snack video from PaintedRose

Giantess Loves a Little Snack Giantess is looking all over for you. Why are you hiding? Are you under my heel? You shouldn't hide, I could step on you! I am so sweet to you and you don't appreciate it so you much be punished. You must kiss each of my toes. That was nice but, not enough. it's time for you to play with me. I think Our game today is you will be my tasty little snack.

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Taboo Mom Teaches You: First Time POV 2 video from PaintedRose

Taboo Mom Teaches You: First Time POV 2 (Step) Mom is just home and changes while you're just waking up. You catch a glimpse and get an erection. When hanging out...you ask me about erections and if it's weird that you got turned on. Mom confesses that girls get erections too and lovingly gives you some kisses for your aching Yummy Dick. Mom strips out of the robe teasing you with her lingerie and showing you her body. She asks you to take your turn at oral and teaches you how to suck on it. Then she asks you to put it in! Missionary followed by doggy style creampie! Mom tells you that yu did great for your first time and how you will have many more evenings like this! It's so taboo and naughty but I don't care! POV Step-Mommy / cougar Fetish Roleplay - Gentle Femdom MILF.

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Flowers: Make Up Sex w/ Mom video from PaintedRose

Flowers: Make Up Sex w/ Mom You have been so busy that you have not spent a lot of time with Step-Mom lately. She's feeling this and doing everything to get you to hangout with her. Yummy breakfast and a cuppa coffee later, you agree to hangout after your shower. You're interrupted while naked and hard in the bathroom by Mom - she stares at your stiff boner shocked and then runs out saying she's so sorry. You feel bad about the hardon but not bad that you saw your Moms thick body and rack too in the little shower mishap. You pick her flowers to show her that you love her because she's the best Mom ever and you can tell she's very upset by what happened. To your surprise, she kisses you on the lips and then doesn't make a fuss or run away when you get a stiffy from the kiss. You want to fuck her but that's impossible - she's your Mom! In the middle of the night you run into eachother in the hall - neither of you can stop thinking about it - the naked incident, the kiss, what you are feeling... She says she feels like a horrible Mom because she wants your cock and it's forbidden lust! As you come toward her - you pin her in the corner and kiss her to show her you're a man now. She says no but then drops to her knees to suck you but she tells you not to cum.. yet. Then you fuck her all the way to her bed for some love-lust make up sex! This video contains Step-Mom fetish, doggy style, 2 blowjobs, bent over chair sex, missionary, Mom On Top, a squirting real orgasm, and lastly - you on top giving Mom a dripping creampie! This is a Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Your Father's Son: Breeding Love video from PaintedRose

Your Father's Son: Breeding Love After losing your Father many years ago when you were small, Step-Mom had to marry your uncle platonically to get health insurance for you but now that your older there is a problem. Uncle wants your Mom to have a babe with him but, she isn't inlove with him - she doesn't want to be pregnant by a man she doesn't love. You are very close with Mom and you love each other very much. She always says how you look and act every bit of the man your father was and how you're more special to her everyday. Mom wants to be pregnant but, by a man she loves and you offer to be her man, her love, the father and carry on not just your genes but also your Fathers! After some convincing the sweet love turns steamy and seductive as Mom gives you your first blowjob, doggy, and you fill and breed her pussy and womb with your taboo seed of love. Taboo Step-Mom Roleplay Fantasy with POV style impregnation, romantic love and slow burning lust. Thank You!

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Step-Mom's Work It, Twerk It, Squirt video from PaintedRose

Step-Mom's Work It, Twerk It, Squirt You walk in and Step-Mommy is working out in her leotard and leg-warmers. She says she does her stretching before her pussy stretch and then shows you her workout equipment which consists of an array of large dildos. Step-Mom starts with an anal dildo for a little rim job and then starts stretching her pussy with dildos normal to huge! When she get's to the big boy stretch - she fucks it front and back and on her back. She let's out a tiny squirt and then keeps working her pussy out until she cums and squirts all over her workout mat! Work out with me with your own dildos or watch and work your love muscle with me.

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Cuckold Training Lesson - Sexy Tutorial video from PaintedRose

Cuckold Training Lesson - Sexy Tutorial In this complete training video, I will train you and my new Cuckold how to Fluff, Serve, Suck Cock to get it hard, cum eating privileges. We also discuss your chastity, panty wearing, and load swallowing! The bull gets sucked and then he fucks me hard! He creampies me for you. You are then required to clean his cock and my creampie pussy. POV, Cuck, CEI.

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Student Gets English Teacher Pregnant video from PaintedRose

Student Gets English Teacher Pregnant Student goes to see Homeroom teacher to get the english assignment. Of course he forgot a pencil. She is walked in on crying by her favorite student. She tells him she can't get pregnant and eventually she suggests he gets her pregnant. She gives him his first blowjob, has him eat her on the desk,She rips a hole in her pantyhose and she gets fucked sitting and finally bent over the desk. He creampie her and she cleans his cock with her mouth and tells him she needs to see him again after school tomorrow to make sure she get's pregnant.

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Sinfully Sweet: Step-Mommy's Good Boy video from PaintedRose

Sinfully Sweet: Step-Mommy's Good Boy When Step-Mommy leaves for work you are suppose to be in bed but you wanted to stay up. She is dressed in a funny costume and you ask Step-Mommy about it. She just said, "Step-Son, I needed The Money" Whatever that means. Later in bed while Step-Mommy is at work, your pee pee got hard and hurted a lot and you told Step-Mommy about it and she told you to rub it. While watching, Step-Mommy starts acting weird and rubbing her panties in the front. Step-Mommy tells you that girls masturbate too. Step-Mommy fucks your cute little boy pee pee in all positions until you explode cummies inside of her. Extreme dirty talk in this HOT Step-Mom fetish film!

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Taboo Touching: Mommy Watches You Cum video from PaintedRose

Taboo Touching: Mommy Watches You Cum You come up to cuddle and Step-Mommy notices you have your first erection. She tells you that it's ok and to do what you need to do. Mommy is a little embarrassed and unsure how she should help. She is surprised when she looks over and you've pulled it out and are jerking off. She quickly looks away and you ask her to watch. Mom tells you she shouldn't but, that she loves you so she will. She begins to become aroused watching you at times while encouraging you as you're trying so hard. Mom touches her nipple in front of you while sensually becoming aroused watching you touch yourself. Mom tells you to cum for her like a big boy. This is a POV interactive Taboo Femdom first time JOI scenario.

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Loser Puddle - Jerk Off Humiliation video from PaintedRose

Loser Puddle - Jerk Off Humiliation Rosie walks in on you jerking off.. again. Is that really what you do all day? What are you a jerkaholic? A Chronic masturbator? Hmmm? It's really PATHETIC! She mocks and teases you for looking so stupid with your mouth open and whimpering before you cum and how stupid and dumb you look. Then she makes fun of you more once her humiliation makes you cum a little loser puddle...

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Practice Makes Perfect 4K video from PaintedRose

Practice Makes Perfect 4K A Rosie Original. Step-Mom comes to ask why you aren't ready for class yet and she can tell something is wrong. You finally tell her that a girl turned you down for a date and that it was embarassing. You need some pep talk comforting and some practice to learn how to talk to, kiss, and impress girls. Practice makes you start to feel more confident and makes Mom get really turned on.. oops. Pretty soon you're both naked so that you can learn all about the sensitive .places on a womans body and practice how to turn on and fuck a girl. You eat pussy so good that Mommy squirts and then she gives you a HARD earned blowjob. You get fucked cowgirl and then you bang her from behind like a good boy. Next you get on top so you can put your creampie deep in your Mom's thick juicy Pussy. 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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All About That Ass Jiggle video from PaintedRose

All About That Ass Jiggle This is a video clip of me making my butt jiggle, wobble, twerk a little and then humping the bed and my hand until I cum for you!

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Binge Watch and Chill - Mom / Son POV video from PaintedRose

Binge Watch and Chill - Mom / Son POV You notice Step-Mom and how sexy she looks on her bed and she invites you to binge watch and chill together. You guys talk about her disaster date and she says she's done with dating. You tell her how it makes you jealous when she goes out with guys and she is surprised and has an idea. Mom says you can have a little secret together. A naughty secret. She touches your already hard cock and makes you cum. Later on, Mom tell you she is still horny and you confess wanting another blowjob. She suggest instead that she teaches you to fuck. She is surprised at how well you do as you thrust your hips underneath of her and from behind. You love her big boobs bouncing on top of you. You lay Mom back and slide in. You make a nice creampie inside as Mom tells you to "cum inside of Mommy". Virtual Sex, Mommy roleplay, POV.

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PantyHosiery Joy: Sensual Seamless Seduction video from PaintedRose

PantyHosiery Joy: Sensual Seamless Seduction I know you like to look and I want to show you my new seamless silky shiny pantyhose. These tights are wrapped around curvy body so cozy, smooth, and silky turning me into your pantyhose slut. Your eyes won't look away as I model them for you while I frequently look down to see how hard you are for me and my hosiery legs, ass, and juicy pussy. You'r stiffness and intense gaze make me swell and I can no longer wait to touch my juicy pussy for you. Let's see how wet we can make these naughty nylons. A Rosie Original. 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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Truth Or Dare: Mommy Dares You To CUM! video from PaintedRose

Truth Or Dare: Mommy Dares You To CUM! The babysitter told Step-Mommy that you tried to touch her Boobies and so Mommy sent her home and decides it's time for a game. Truth or Dare (Pick the dare - wink wink). Mom tells you that you are her good boy and it's normal to be curious and like to look at and touch female bodies. She says not to try it with the babysitter anymore because her boobs are too small anyway. During the game, you dare Mommy to get naked and she dares you to take out your pee-pee. One thing leads to another - quite intentionally on Mom's part as she teaches you how to rub your privates together to make them feel really good. Step-Mommy goes from sweet to sultry and horny. Step Mom shows you her body, plays with her pussy, teaches you about blowjobs, missionary, cowgirl, doggy style and a close up orgasm in your face that she has you lick clean with a missionary creampie finish in Mom's dripping taboo fuck hole. Lots of dirty taboo talk.

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Rainy Day Play: Mom Rubs on Son's Privates video from PaintedRose

Rainy Day Play: Mom Rubs on Son's Privates It's raining and thundering and very boring to go outside and play. You see mom watching TV and come in to see if she wants to hang out. Mom invites you to lay down with her. You hesitate because she's only wearing a bra and pantyhose/see through leggings. She says it's ok so you get in and can't stop looking at her body. You get hard and mom asks you about it. You say its because of her. She asks if you masturbate yet and you say yes. Mom says its ok. You're too young for sex but she will stroke you. She gets turned on so she rubs her pussy on your erection and tells you to cum. She says you guys can do this new playtime everyday! Custom Video. AP.

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Little Brother: This Never Happened video from PaintedRose

Little Brother: This Never Happened Your older Step-Sister wore the most revealing bikini at the pool today and she had you put oil on her in those hard to reach spots. Later on - she finds you by her bed because you brought her stuff up from the pool and she thanked you and apologized for how mean she was to you when you were little. You compliment her bikini and she gets embarrassed - you know she hasn't fucked in a while and you pull out your dick to show her what she did. She again apologizes but she can't look away and tells you she want's it but that you can't tell anyone. She's starving for your cock and fucks you like a hungry dirty MILF starving for forbidden dick. Ass tease, gagging sloppy BJ, Doggy dick ride, Cowgirl, Missionary CUM INSIDE YOUR SISTER! Look at me when you cum. Lots of taboo talk! This is a Family Taboo Roleplay Fantasy with POV Virtual Sex. This Never Happened!

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Curvy Mom's Seamless Silky Pantyhose video from PaintedRose

Curvy Mom's Seamless Silky Pantyhose Step-Mom has been noticing pantyhose and tights missing for a while. She didn't know where they were going to until one day she sees you with them wrapped around your dick while you masturbated. She couldn't look away and then used the returned pantyhose to masturbate alone. She's been feeling like confronting you and has held back but, now it is your birthday so she decides to surprise you. She gets home from work and does not have panties underneath of her black hose. You begin to rub moms feet and she lets her legs apart for you to see knowing you can't look away. Knowing that it turns you on she teases you. Mom tells you to put your face in her crotch and smell the hose she's worn for you all day. You start licking until mom has an orgasm. She then tells you she has a birthday surprise. You go into Mom's room and she is waiting, nothing on but some new seamless tights she has bought for this occasion. They are silky and soft. Mom uses the black tights from work to jerk your cock. She then masturbates through the hose. She Can't handle it and rides stiff dick to show you the great thing about the seamless tights. Mom then rubs her pussy to orgasm and squirts with her orgasm wetting the pantyhose further. Mom then strokes you to cum again for her! Custom Video.

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Tag Team Work: Suck, Fuck, Facial! video from PaintedRose

Tag Team Work: Suck, Fuck, Facial! You're sent to the counselors office by the principle with an ex-friend becasue the two of you can't seem to get along. Rosie gets to the bottom of the problem and decides some teamwork roleplay therapy would help the two of you. She locks her office door and you think she has to be kidding until she starts to take off her clothes! Could this really be happening? She tells you both that you will have to work together to properly fuck all of her holes in order to achieve the goal of cumming all over her face. You will have to work as a team, take turns, and of course be obiedient when she tells you to to fuck her harder! You're ordered to both drop your pants NOW and the first one gets to put his cock in her mouth. Counselor Rosie incorporates team building and bonding by any means necessary and no holes barred. This custom film features spit roasting positions, goddy, cowgirl, facial and a stern but gentle approach by your cum loving MILF Rosie! 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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OvereatingMommysFatLittlePiggy.mp4 video from PaintedRose

OvereatingMommysFatLittlePiggy.mp4 You must and and get big and fat, even if you are full. I will bribe you to keep eating for Mommy.

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Missing You Mutual Pleasure Juicy Orgasm video from PaintedRose

Missing You Mutual Pleasure Juicy Orgasm I miss you and since we can't be together I want to play with my pussy for you until we cum together - wet, juicy orgasm and passionate pleasure.

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Rosie's Granny Panties video from PaintedRose

Rosie's Granny Panties Rosie's New Panty Tryon - Silky Satin Vanity Fair Granny Panties. I try on and tease you in 7 pairs of panties and then I have you cum for me. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Robot Mom Malfunction: Circuit Overload video from PaintedRose

Robot Mom Malfunction: Circuit Overload You're a sweet boy with no mother and so your father decides to get an android robot for maternal and housewife needs. When you get home, your father already has set up the online programming personalization and introduces you to your new Mother. You are surprised at how lifelike she is for a robot - complete with big tits and curves. She calls you "My sweet good boy" and other names that make you feel affection toward her. She's been doing a great job as her program settings require her to be the perfect Mother and Wife. One day she asks if you are having, "A bad day". You finally tell her what's wrong - that you have sexual attraction toward her. She informs you that all sexual remarks, questions, and touching is prohibited in her code. She uses her self directed autonomy allowance to research and she tells you that you have a Mommy Fetish and that is is not a PG rated allowed topic. She begins to malfunction and 'feel' compassion - a mothers love and decides to research more about a robot fetish which turns out is NOT prohibited. She has found a way to bypass the adult block your father has set up in her code. As you show her your penis and begin jerking off, she informs you that for educational purposes, she may assist you in order to learn about masturbation. This film features a combined robot and mommy fetish, handjob, blowjob, cum on tits, cum in mouth. 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.

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Valentine: Old Friends, New Lovers video from PaintedRose

Valentine: Old Friends, New Lovers She's alone on Valentines Day and so are you - the single ones in the friend group. You decide to hang out last minute and you bring a bottle and she brings the sweetness. Catching up and having a relaxing evening turns into a little soft music, slow dancing, and a sensual mood.. Why not? We let the mood get away with us promising not to ruin our friendship with this new crush or whatever this is. You take her on from behind on the chair, Then she starvingly sucks you like she's eating her first steak, and then front facing hot sex! A Rosie Original!

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Mommy Date - Get Mommy Pregnant video from PaintedRose

Mommy Date - Get Mommy Pregnant I am so happy to see you! WE are going out for a special Mom / Step Son Dinner date. One thing leads to another and ooops. Suck, Fuck, Ride, Cum...but wait...bareback baby - get Mommy Pregnant! Mommy is so loving and nurturing!

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Santa's Baby: Christmas Cocks For Rosie video from PaintedRose

Santa's Baby: Christmas Cocks For Rosie 2022 Christmas Film! I've been a good girl all year and you're finally here with some presents for me! Three presents - Is this one the key.. the ring... the deed.... ? Oh My - Dildos! Thank you Santa! Before my eyes the dildo turns into your cock - Did you bring some milk for my cookie Santa? Suck, Fuck, and Ride on all three of Santa's Magical Christmas Cocks! This Cougar Christmas video features, raw and magical fucking, cowgirl front and back, cock sucking, real lustful squirting orgasm, doggy style, candy cane cream filling with raw breeding maybe baybe! This video is FREE for all of my subscribers! Happy Holidays!

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Painful Penis Punishment - Jerk Off Humiliation video from PaintedRose

Painful Penis Punishment - Jerk Off Humiliation It's not really a Surprise that Step-Mommy caught you jerking off and this isn't the first time. You know you have to have permission to touch it and since you've disobeyed and had another erection, you must be taken to the punishment chair. I pull out my big tits to soothe you a bit because what is coming will only seem like a reward at first. Suckle as I jerk off your little dick until you begin to spill from your poor, pitiful penis. Thats the fun part where the punishment comes in. Your orgasm will be cruelly ruined by your Mother while she laughs and spanks you on your cock and balls. Filthy. This film is a custom made video that is a 2257 compliant adult roleplay fantasy and features taboo step-mom roleplay, verbal humiliation, corporal punishment, handjob, breast suckiling, and a ruined orgasm with dick and ball slapping.. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Thank you SO MUCH! Hugs and Smoochies, Rosie.

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Naughty List: Mom's Sissy Slut for Santa video from PaintedRose

Naughty List: Mom's Sissy Slut for Santa It's Christmas Eve and your sweet and sexy MommyDomme calls you upstairs to see what you're wearing for Santa! That won't do dear so you get to open up a present early! It's something sexy to wear - oh it's ok honey, I know you love panties as much as I do! Your slutty role model step-Mom tells you that Santa loves naughty girls just as much or more than the good girls and that there is one for sure way to get everything that you wanted on your list! Santa is coming with his big candy cane and Mom shows you what you're going to do with it. In the end, you show off your cute little AssPussy and have your first SissyGasm! This is a fun and playful feminization training video with a naughty girl Christmas theme! I just love my CD, TG, Bi, Sissy Sweeties. Merry Christmas!

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Sissy Girls Get Curls video from PaintedRose

Sissy Girls Get Curls You arrive at Step-Mom's house after being kicked out by your girlfriend for trying to be manly. I guess it's time for discipline and training. You're so weak for Feminine training with MommyDomme but lack the confidence to be your true self in front of your girlfriend. Mommy now owns your balls and says that you will give your masculinity to her as you are transformed into the ultimate service sissy girl. You;'ll begin your training right now as you weaken from Mommy's lingerie, curls, and her FemDominance over you and your sissy bitch needs. You need girl training, discipline, and fucking sissygasm for servitude. Thank you for this custom video. This film is 2257 compliant and a solo performed roleplay fantasy.

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Let's Get Physical: Mom Works Over Son. video from PaintedRose

Let's Get Physical: Mom Works Over Son. Mom (Step-mom) does her workout. She's Sooooo eighties! Retro Mommy with Shiny Pantyhose and legwarmers. She teases you with her naughty cameltoe. Mom sees you there looking so starving for her and since she's feeling like a horny MILF, she feeds off of your stiff boner. She pulls out your cock and uses it for her fucktoy and takes your cum!

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Fucking Pervert: Mom's Cum Boy video from PaintedRose

Fucking Pervert: Mom's Cum Boy You get home to find out the principle already called Step-Mom and told her you tried looking up the teachers skirt. Mom checked your room and pc and knows all your dirty secrets - your search history about MILF's and her panties under your pillow!!! She tells you repeatedly how you're a fucking pervert while berating you and she's also pissed that you are into the teacher instead of her. How dare you flirt with that bitch - do you know how much trouble we could get in? No more dirty boy at school You have to start cumming before school every day with a proper dirty MILF - Your MOM! Step-Mom teases you with dirty taboo talk about you listening to her fuck guys and jerking off outside her bedroom door for years and how now it's your turn to be a big boy. She teases you about how you listen to her masturbate in your room and has you lick her pussy while she cums in your mouth. Now that this pussy is wet stick it in and CUM FOR MOMMY - YOU FUCKING PERVERT. This is a dirty talk, Mommy Fetish, Step-Mom, Taboo, First Time, Humiliation roleplay film. I still don't know if this was a punishment or a reward lol!!

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Step-Mothers Milk Is Best video from PaintedRose

Step-Mothers Milk Is Best Step-Mothers Milk Is Best You've just gotten home from school and there is your favorite person - Step-Mommy and her great big milkers. You tell her you didn't want your milk at school and she says it's ok because Mothers Milk Is Best! As you suckle and nurse, your tummy gets full but so does your pee-pee. She notices you're full and aching too and so she drips her breast milk onto your penis and stokes it while you finger her MILF pussy with your hand. You release your MILK for her as you both cum together. What a good boy you are.

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Jealous: Forbidden Lust For Mommy video from PaintedRose

Jealous: Forbidden Lust For Mommy You notice Step-Mom going out more and then she tells you she's been seeing a 'friend' from art class. It's been 5 years since the divorce and you've had your Mom all to yourself and the thought of some other guy taking her out makes you so upset! You know that she's your Mom but you also realize you have forbidden feelings and desires. Over a few days, you realize if you want her to stop dating this dick, that you need to do something to show her that you can be her man. Step-Mom tells you she wants a friend for adult activities and that it's time for her to start thinking about her unmet needs for love and intimacy. You reach out to touch her breast and at first she jumps and says it's wrong but, you don't give up. You drop your pants and show her your big stiff cock and she can't stop staring as she begins to drop her dress for you. You promise to be the man she needs and agree there is no going back. This film is a Step-Mom fetish roleplay fantasy love-lust story of drama, loving playfulness, passion, forbidden taboo, dirty talk, wet pussy and MILF Mommy Sensual Dominance. This video has POV doggy style, blowjob, close up squirting, cowgirl, reverse, dick twerk, and dripping creampie. A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Son's Footrub Turns To Sex: Dad Snores video from PaintedRose

Son's Footrub Turns To Sex: Dad Snores Step-Son comes in and wakes Mommy to ask her if he can rub her feet for 20 bucks for a video game and she wakes up and says ok. She will do anything he asks. Dad is napping and is snoring from his sleepytime pills. Mom and son fuck doggy after she blows him, then he fucks her missionary while she uses dad for a pillow, then son licks mom's pussy, Mommy Blows him some more, then she reverse cowgirl fucks son until he cums inside right next to lazy napping Dad. Lot's of cheating talk, soles of feet, Sex. Dad snores lightly the whole time !! Custom Video.

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Son-In-Law Seduces Mom w/ Big Dick - Horny Homewrecker MILF video from PaintedRose

Son-In-Law Seduces Mom w/ Big Dick - Horny Homewrecker MILF Mom is ironing shirts for her (YOU) Son In Law when he comes over early to see her. She is surprised by this and his flirting. She reminds him that he is married to her daughter. He tells her that he has a big dick and knows she needs it. When he starts touching her breasts and upskirt with his big, strong hands she stops resisting. She tells him it's a secret and not to cum in her!He let's big big boner flop out and she immediately starts sucking it. She's starving for dick and getting fucked. He bangs her doggy and then puts her legs in the air for a fuck and creampie! He cummed in mom's pussy!! She begs him to cum inside!! She took his 10 inches very well. Close up creampie cumming. Son is the seducer.

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Mom's Panty Punishment: Stuff and Soak video from PaintedRose

Mom's Panty Punishment: Stuff and Soak Step-Mom notices that her panties are disheveled and asks you if you know who has been going through her panty drawer. She is surprised that you confess so easily and decides your punishment shouldn't be too harsh since you came clean about the naughty behavior. Mom starts telling you with electric sexual energy how you shouldn't be turned on by your own Mother and in fact that nothing she does is to encourage you to - take out your cock and stroke with her. Your mother turns into a horny babe as she removes her panties and begins stuffing them deep inside her pussy. Mom loves the pressure and she she fucks her pussy and asshole with her fingers and the panties you love sniffing so much! Mom keeps going with this reverse psychology mutual masturbation until she tells you NOT to cum with her as she moans and soaks the stuffed panties! As she pulls them out, you get a little souvenir gifted to you for taking your punishment so serious. This is a POV interactive Mom /son roleplay fantasy and mutual masturbation with panty stuffing and a really wet female orgasm. Thank you for this custom video!

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Dad's New Wife: Better Than Your Mom video from PaintedRose

Dad's New Wife: Better Than Your Mom You get to your Dad's house and he isn't back from work but, his new wife is there waiting to meet and greet you. Rosie welcomes you and tells you how she wants to make sure you always have the best time when visiting. Rosie asks you what you would like to call her and is very pleased that you will call her Mom. Afterall, your real Mom is way too hard on you. She doesn't let you play games, fool around, or watch porn! New Step-Mommy tells you how she bought you a gaming system, candy, and that you can have all the fun you want at your new home away from home. In fact, she confides a little secret that your Dad would LOVE for you to stay with them all the time. Just think about it son. Rosie confides that there is no porn block on the WIFI and that masturbation is normal. Just then, Rosie has a malfunction with her top and the buttons becoming loose because her boobs are too big. She asks you if you think they are too big and if you like them. New Step-Mom Rosie noticed a HUGE bulge and tells you that your old Mom shouldn't be so strict and that you should be allowed to date girls and have sex. Rosie begins to seduce you with her body, mouth, pussy and a nice creampie finish! This is an interactive POV Mommy Fetish Virtual Sex Cheating Wife Taboo MILF Roleplay!

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Red Light Rosie - Pussy Passion video from PaintedRose

Red Light Rosie - Pussy Passion When the red light comes on - you STOP and let Rosie tease and tempt your senses with her eyes, lips, ass, hands, and her juicy pussy. Let's cum together? Now. Please :)

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Santa's Helpers: Stocking Stuffers video from PaintedRose

Santa's Helpers: Stocking Stuffers Rosie gets a surprise Christmas Morning with Santa and two elves. Rosie has been a good girl all year and Santa says she can be naughty for one day! She tries out both elves - an average size elf cock and A fat dick elf. Rosie makes both cum (Orally, Cowgirl, Doggy) but the winner gets a special reward and gives Rosie a mouthful of candy cane rod and a throatful of sweet cum! This is a POV, Cock size comparison, naughty horny cougar, holiday Christmas, Virtual Sex roleplay film! Thank you!

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Pervert Like Mommy video from PaintedRose

Pervert Like Mommy Step-Mommy finds you resting in her bed and decides you must want to cuddle. She's only wearing her bra and panties and your eyes become very big with curiosity. After some cuddles, Mommy shows you her outfit and shows you her big Mommy Milkers and talks to you about your pee-pee. She shows you her private place up close and tells you her 'pussy' can do a squirting trick that you can see if you watch real close. You need an anatomy lesson about girls bodies while Mom also teaches you about touching your private part - your cute pee pee boner - your 'dick' Son. After the yummy squirt trick with lots of dirty talk, Mommy says it's fun to rub your private parts together so that you can, "cum for Mommy"! A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy,

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Ringing In The Anniversary - Homewrecking Mom video from PaintedRose

Ringing In The Anniversary - Homewrecking Mom Mom is in bed and dressed in virginal white lingerie while her son rubs her cute pedicured feet. Just then, Dad calls to say he is on his way home and wants her - it is their Anniversary. Mom decides it's time to train her son for a stiff, vigorous fuck since Dad is boring and no good in the sac. She sees his massive dick print and begins to drool. She calls him over and his big bouncing boner flops out in her face. She says, "You didn't get that from Dad". Mom blows, bangs, and bucks this stud cock. Close up reverse cowgirl cumshot. Surprise ending. Dad calls during the sex and doesn't suspect a thing! Nothing is sacred to the home wrecking busty MILF. She gets cum on Dad's side of the bed, her hug wedding ring, and the panties she's wearing for Dad tonight!

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Candy Cane Daydream: Pantyhose Play video from PaintedRose

Candy Cane Daydream: Pantyhose Play Christmas morning is best with something sweet like caramel coffee or hot chocolate or perhaps some candy? Festive and fun, Rosie teases and models her body in pantyhose until she is super turned on and rubs her pussy through the hose until she has a REAL orgasm. There is a special present for you at the end! This is a POV JOI encouragement pantyhose video.

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Christmas Chastity Release: CuckBaby video from PaintedRose

Christmas Chastity Release: CuckBaby Merry Christmas CuckBaby, I have a little gift for you! 10 minutes. A ten minute cum release. My bull is fucking me tonight but right now you get to be teased and taunted to cum as many times as you can. Rosie is not kidding about giving you a release you won't forget. Because it's Christmas, she lets you get close up enough to smell and almost taste her.. almost. Lightly humiliating, gently firm, unmistakably Rosie.

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Forget Me Not: Miss Rosie's Panties ENF video from PaintedRose

Forget Me Not: Miss Rosie's Panties ENF School just let out and Miss Rosie didn't expect any students today but you have a last minute project to finish and print out. Miss Rosie says you came on a bad day because her button broke and she forgot to wear panties today. She's really embarrassed but at the same time sweet, playful, and silly. She asks you not to tell anyone because she is so embarrassed for anyone to know she didn't wear panties and thanks you for not telling. Miss Rosie does all kinds of silly stuff like reaching, bending, and retrieving items for you and she's just popping out all over with nipple slips, losing shoes, pants falling to the ground with different angle views - even a little shoe dangling while struggling with the pants - or lack of! This is an ENF Embarrassed Naked Nude Female MILF POV interactive scenario. Have fun! Thank you for this custom film!

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Playtime Together: Virtual Mom / Son Dual Masturbation video from PaintedRose

Playtime Together: Virtual Mom / Son Dual Masturbation Mom is resting and is having a naughty dream and is touching herself, just then her boy comes in and sees and watches for a while. He then wakes her to cuddle. They start touching while she rubs his back. She starts stroking his stiffness because it's hurting. She gets turned on and takes his hand between her legs as she teaches him how to get her off with his fingers. First time mutual masturbation for mom / son roleplay. hints at ageplay, POV, Virtual sex.

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Sissy Slut Faggot Toy For Mommy and Her Big Black Bull video from PaintedRose

Sissy Slut Faggot Toy For Mommy and Her Big Black Bull Sissy Slut Faggot Toy For Mommy and Her Big Black Bull. You hear loud noises and thumping coming from Mommy's (Step) bedroom and you go to check on her. You see a naked man kissing Mommy, a big black man, and she is kissing him too. You' are staring at his big dark colored penis going in and out of Mommy's private place and... then Mom Sees you watching and get's upset with you. She notices your tiny little pointer and laughs at you. She tells you you're a sissy slut and that you're Mommy and New Bull Daddy's Fuck Toy. Then comes the good part.. Thank you for this custom Audio Story.

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Ass Tease Session: Upskirt and Naked video from PaintedRose

Ass Tease Session: Upskirt and Naked You arrive for your weekly roleplay session with the Guidance-Counselor Rosie and as promised you have been a good boy all week and have not done any upskirt peeks at school. Your reward is a roleplay with Rosie, who loves exhibition! You get to peek and watch as she walks around cleaning, bending over, stripping as she gets hot and she teases you with her buttcrack relentlessly until you can't help what her eyes are telling you to do. Thank you for this custom video! This video is a POV roleplay MILF ass crack buttcrack tease video.

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Step-Grandma's Pregnant Breeding Pussy video from PaintedRose

Step-Grandma's Pregnant Breeding Pussy A few months ago, your girlfriends Step-Grandma seduced you into fucking her raw without a condom. You love Step-Granny's curvy mature body and sensually seductive sex! You come back to town and find she's moved in and has taken over running the household in place of her Step-granddaughter who will now take the smaller bedroom. GILF Step-Granny - is a real woman and now she's having your offspring! She warns you that her body is changing and she's extra horny and needs her Step-granny pussy full of your cum at all times. She knows you desire breeding as much as she desires being a Step-Mother and staying pregnant! Thank you for this custom video!

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Mom's Christmas Coupons: Kiss Suck Fuck! video from PaintedRose

Mom's Christmas Coupons: Kiss Suck Fuck! Step-Mom got her hours cut at work but she still wants to make sure that you have a memorable and amazing Christmas. Mom thought LONG and HARD about what to get you and It's the thought that counts right? You both decide to do homemade gifts this year and you get woke up to Mom dressed very sexy, is this a dream? No way! Mom gives you your stocking with a coupon book with three gifts! A kiss, A blowjob, and a FUCK coupon. Which will you use first? This is a POV Mommy Fetish with Stepmom Virtual Sex and roleplay with blowjob, doggy, cowgirl, missionary. Doggy Finish for the win. Merry Christmas and Happy Holidays! This video is a gift to all of my monthly subscribers!

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Sweet Sissy Lover: Warm, Wet Holes video from PaintedRose

Sweet Sissy Lover: Warm, Wet Holes Dommy has you figured out and has you put on a bra and panty to wear while you look for her missing white satin bra. It looks so good while you're bent over looking in the bottom drawer. Step-Mommy decides you can serve her better as a girl and tells you that you need to start wearing prettier clothes. Later on she brings you a pretty nightie to wear and sweetly kisses you and tells you how much she loves you and wants to be closer to you - the daughter she never had. Show Mommy you're a girl and lick on this dommy puss - eat it young lady. You do such a good job that you're allowed to cum on Mommy's fingers as she teaches you how to rub that sissy clit and cum. Interludes and lewds in between good girl training begins with you serving Mommy after a long day at the office with your pretty slut mouth before Mommy puts you in the big bed with her to get your cherry fucked and bred by her Dommy-Dick. You are told to get on top of Mommy to clitty fuck and impregnate her with your sissy squirt. A Rosie Original. This Film features some wild and naughty feminization, love-lust story, Sissy-Daughter, Strap-On, Oral Sex, Masturbation, Fingering, Breeding, lipstick lesbians, androgenous, sissygasm, and dancing - we must dance Babe. Thank you long time friend Chrissy for commissioning this film.

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Feminization Training: Hair and Makeup Like Mommy video from PaintedRose

Feminization Training: Hair and Makeup Like Mommy You wake up handcuffed and drowsy in Step-Mommy's Salon for feminization training. You have been put in lingerie and Don't resist much when mom explains how she is turning you into her daughter. Mommy is wearing a strap on, you wonder why. She says later you're going to learn how to get Mommy Hard. I know you like Mommy's style and want to be like me... You had better hold still young lady or you will get a hairbrush spanking. Today the training focus is on wearing makeup, getting your hair curled, wearing sexy lingerie, and smelling nice. Mommy is sweet but firm in her training.

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No Peeking: Grandma's Panties video from PaintedRose

No Peeking: Grandma's Panties It's just you and your smoking hot young Grandma tonight and she just got in from work and begins to change. She has you turn around - no peeking young man. You didn't peek did you? After you beat her in 3 games of hangman, she asks you if you like girls and if you masturbate. Step-Grandma gives you some great advice on girls! The next thing you know, Grandma tells you she likes your DP (Dick Print) Where did Granny hear that term!?! You don't care because she is a hip Grandma and very cool for an old lady. Just then, Grandma asks you to show her how you jerk off, you're already hard as a rock so you take it out and start stroking...Grandma think you need a hand and a mouth. She tells you she's a girl too while she blows your cock. Fuck - do you think your parents will come up and see grandma's head bobbing on your cock? Grandma tells you to keep it down and a to keep it a secret. She shows you her big rack and wraps her titties around your dick and spits on it and begins giving you a Titjob next. You want inside Grandma and she asks if you want to see her granny pussy? She shows you her ass and tells you to fuck her doggy style! Grandma fucks you on top and then begs you for a creampie. She loves you her big boy Grandson and your wet cumload. Shhhh.. Our secret sweety. This is a taboo roleplay POV fantasy virtual sex with dildo shown for sex scenes. Thank you - I hope you love this!

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Son Consoles Lonely Mom: She Got Dumped video from PaintedRose

Son Consoles Lonely Mom: She Got Dumped Step-Mom comes in and tells you she isn't going out. This jerk dumped her and said she was just too old for him! What? Too old? You think your Mom is hot and offer to be her date. She thinks you are kidding but soon realizes that you mean it. One thing leads to another as you console Mom and she wants to show you her body. The tables turn as she begins to seduce you! She strips down and tells you to show her your cock! Her eyes widen with delight as she begins to remove her stockings and show you her shaved and smooth pussy. You fuck her missionary, get blown, Cowgirl on top, and finally a creampie doggy finish! Mom shows you your wet load as her pink swollen pussy glistens from your yummy load and she just has to have a taste. This is a POV Mommy Fetish Roleplay Fantasy Sensual Seduction Film. Thank you!

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Late ASSignment: Pants Falling ENF video from PaintedRose

Late ASSignment: Pants Falling ENF You know you turned in the ASSignment but Miss Rosie says she can't find it and you have to repeat it or fail. She told you to bring a leather belt for the texture comparison paper but, you don't have one and are unprepared.. again. Miss Rosie is unhappy and tells you throughout that you're a bad student and is very uncomfortable without her belt. Her pants fall repeatedly to the ground and each time she get's madder at you. This is a POV and interactive MILF, Ass, Buttcrack, ENF, Embarrassed, Pants Falling, Teacher scenario. Thank you for this custom video!

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Giantess Goddess Rosie Visits Tiny Town video from PaintedRose

Giantess Goddess Rosie Visits Tiny Town Beautiful, but mean giantess Rosie gets her girlfriends together and they head on an adventure to get some teeny tiny college boys. She puts them in a container and teases them and enjoys squishing, eating, stepping on them one by one for her sick pleasure. Vore and Giantism. Custom Video.

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