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Showing 61-120 of 600 Results

Date Night Detour: Ordering In video from PaintedRose

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

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Condom Broke: Oops Taboo Impregnation video from PaintedRose

Condom Broke: Oops Taboo Impregnation This is a roleplay fantasy about stepmom being impregnated by stepson. You come in Mom's room to ask her if you can get in her bed. She half awake agrees and goes back tobed. You keep moving closer and something pokes her. She asks if this is going to keep her up all night and decides to, "take care of it" She says you have to use a condom because she can get pregnant really easy right now. She tells you to stick it in from behind. She rides you from the back. The a hot sexy missionary fuck where she tells you to cum inside (the condom). Afterward while enjoying the orgasm, she notices the condom is off...I guess it broke.

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Go Deeper For Goddess Rosie video from PaintedRose

Go Deeper For Goddess Rosie You want to go deeper, you need to and you will worship your Perfect Goddess over and over again. This is a Daily Devotional for seducing your mind and body with the most perfect Mistress that deserves daily spoiling. As I seduce you, you will worship your Goddess properly and repeatedly into a frenzied and earned cum session. You're Welcome. This film is 2257 compliant and a solo performed roleplay fantasy. 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 Gift Of Devotion: 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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Mommy's Pee Guzzling Boy Cums Inside video from PaintedRose

Mommy's Pee Guzzling Boy Cums Inside Step-Mommy calls you in and slowly teases and strips completely naked to tease you and tells you that you have to consume her piss and lick her pussy clean after she pees to be rewarded. You will do it. Look how you are getting hard. You comply with Mommy's demand and are then allowed to fuck her tight pink pussy until you cum inside. Close up long pissing into glass, made to guzzle pee, and visual close up of you cumming inside. Good boy.

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Girl Cocks: A Futanari Story video from PaintedRose

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

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Teachers Sissy Boy Detention video from PaintedRose

Teachers Sissy Boy Detention You are late for detention so now you will get a paddle. You like your teachers pantyhose and while bent over her knee, she feels your boner! So she decides to stop using her hand and use the wooden paddle! She spanks you harder. "You're Step-Mother should have done this at home"! Teacher then puts a stop to your boners with a chastity device. She humiliates you for having a sissy dick and teases you with her vibrator. Teacher tells you not to dare touch it! Teacher teases you into coming in your cage with a soft sissy dick but takes the vibrator away to ruin your orgasm for being a pervert in her class! See you for tomorrow's detention. Don't be late. Sissy Training, JOI, Cum Control, Ruined Orgasm, Chastity, Pantyhose and Teacher Fetish.

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

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

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Becoming A Man For Mom video from PaintedRose

Becoming A Man For Mom You're getting older and Mom is getting hotter and sweeter. You've really bonded as she has devoted her prime years to only raising and loving you and you can't help but notice her body with all of your raging hormones and primal urges. Since you and Mom have been working out together, doing yardwork together, and hanging out a lot - you're just the best of friends.. more than just a Mom and Son. You accidentally see Mom come out of the shower and later that day, she walks in on you and sees you in the shower. Later on, Mom is in her room touching herself and something just comes over you and you enter her room and tell her that you want her. She is so embarrassed and explains that Mom's get horny too and that it would be wrong for her to cross the line of lust with her boy. The bulge in your pants convinces her to forget about her morals and primally take her boys virginity on her knees as you enter Mom's wet pussy from behind, then she slobbers your knob with a wet, sloppy blowjob before cowgirl riding your young, stiff meat. The she stands over you and has you eat her pussy until she cums on your face. Then she tells you to fuck her in her tight Mommy hole until you cum like a man inside of her. This is a POV roleplay fantasy Step-Mom fetish with a nice build up to an even longer hot and horny FUCK!! Thank you for getting this video!

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Anything For My Son video from PaintedRose

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

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Mom's Pretty Sissy Girl video from PaintedRose

Mom's Pretty Sissy Girl Wake up everyday and remember who you are. Who is that? You are Step-Mommy's Pretty Sissy Girl. Repeat these positive affirmations with me - You're a pretty girl.. As much as you're a good girl, you know sometimes you're a teensie weensie bit naughty and Mommy likes our special naughty time to make you feel so special! Is that little pretty clitty swollen? Of course it is.. It's naughty time now pretty girl. This film is 2257 compliant and a solo performed roleplay fantasy.

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Pantyhose Therapist: Impotence Testing video from PaintedRose

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

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MommyDomme Initiation Sub Training video from PaintedRose

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

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Sensual Heel Dangling: Foot Worship JOI video from PaintedRose

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

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Taboo Duo: Stepmom Finds Your Porn video from PaintedRose

Taboo Duo: Stepmom Finds Your Porn You've recently moved back home since Stepmom is alone now. She uses your laptop to check her work emails and stumbles onto MILF porn. She can't help but wonder if you're into her like that. She's noticed how you look at her, your sweet touch, and your grown up body. She calls you up to discuss what she saw, she doesn't care but she needs to know. If you want her the way she wants you. She tells you to lay back for an experiment and she grinds and teases you. You're instantly hard. She proposes you either run away or stick it in knowing that you can't go back! Just then you stuff your big dick her her pussy and she starts to ride your thick growing shaft. She reaches back and squeezes your balls and tells you that her pussy is yours now and when you cum, she owns you.

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CEO Mom Shrinks Son: Wardrobe Assistant video from PaintedRose

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

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

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

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

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

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Seducing Son's Buddy video from PaintedRose

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

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Taboo Impregnation Stepmom Fantasy video from PaintedRose

Taboo Impregnation Stepmom Fantasy Stepmom Impregnation roleplay, POV, MILF with simulation virtual sex. Step-mom comes in to read a couple chapters of a novel to you. You're in the mood for something else and even though it is forbidden you reach out and touch her breast. She is shocked and decides to leave and tell you that it's not ok behavior. Stepmom actually has fantasies about you and wants more. Later on, Step-mom comes in dressed in lingerie and stripper heels. What? She tells you that after thinking about it, she decided she shouldn't have been so grouchy and she starts teasing you with her body before sucking on your dick. Mom leans back and uses a vibe to show you how you make her pussy throb with a close up, pulsating orgasm right in your face. Now you enter her shaved pink pussy and she tells you to get her pregnant and you cum inside but to be sure Mom takes you again from behind and rides your dick doggy style until you cum in her. Taboo Gentle Femdom Roleplay Fantasy. This is a custom video.

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Pick a Pair: Sissy Boy Panties video from PaintedRose

Pick a Pair: Sissy Boy Panties Step-Mom asks you if you were going through her panty drawer because you want to wear them and she already knows. She wants to play a game to figure out what kind of Sissy you are. Pick a pair of panties; 1, 2, or 3. Mom already guessed it and wasn't surprised at all! You're my Little Sissy Boy. From now on, I will parade you around in this little see through thong to let everyone see your little sissy dick in panties! In fact, let me take a picture right now to send someone who is eager to see the panties you chose. They will also be at the family reunion today - oh what reunion? It's more of a sissy boy coming out party! Maybe you should have a little sissygasm to calm your nerves - go ahead and stroke that tiny sissy-dicklette through the panty. This is an interactive fantasy feminization roleplay.

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Man Of The House: First Paycheck video from PaintedRose

Man Of The House: First Paycheck You finally get your first paycheck on your new job and haven't decided what to buy. Just then, Step-Mom is going through the mail and says she's gonna have to get a second job to cover the bills. You offer your paycheck and Mommy says no way will she take your money but you insist. You love your Mom and now that it's just the two of you, you can help out out you tell her. She begins to cry and thank you and she gets on her knees to kiss you. Mom tells you that you're man of the house now and that the man gets blowjobs, pussy, and ass. Stepmom starts to get horny and take off her clothes - she shows you and touches her pussy and begins to rub while you're on your knees and your face is in her pussy. Mom builds up a wet squirting orgasm that pulsates right in your face! She tells you to lick it up and then bend her over and give her a proper wet bang. Mom tells you that you bought this pussy and it's yours anytime you want as she rides your dick hard and fast! Mom tells you to cum inside and then she eats your cum!

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Keeping Step-Mom's Secret video from PaintedRose

Keeping Step-Mom's Secret One morning, Step-Mom hears you stroking off and can't believe she is turned on by you and your stiff young cock. When she notices you staring at her nipple slip, she says it's ok because nobody else is home. Later on after school she tells you how it turned her on to listen to you jerking and tells you that it's your turn to watch her do the same. Do you like this Step-Mommy Pussy? Step-Mom Tits? Ya, I know - it's ok - I won't tell. Later on You get a special sloppy BJ surprise for a great report card and then Step-Mom tells you that you're coming to bed in her room tonight. That night, she dresses up in lingerie and fucks you POV Virtual Sex - Cowgirl, DS, Squirting, Creampie Cum for Mommy Finale. Three Cum Scenes! A Rosie Original! Thank you.

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Perverted

Perverted "I" Pussy Boy JOI You are a good boy. A very good boy. Why is Step-Mommy wearing those panties you folded in front of you? The answer is because you're a perverted Mommy pussy loving boy! She's moving her body weird and talking so different and you like it, you love it.. you feel like it's a dream because nothing has ever felt this great! Lots of very taboo dirty talk in this Good Naughty Boy JOI! Curvy Naughty MILF Gentle MommyDomme Rosie! This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Classroom Cock Lock: Caged Confinement video from PaintedRose

Classroom Cock Lock: Caged Confinement Since this bad report card came home, it is time for gentle Dommy to take action. Your obsession with short skirts, womens curves, lingerie, hosiery, and fantasizing about sex is interfering with your concentration. Mom decides your punishment will be painful - penis pain with those constant boners from your bad little boy brain working overtime on the wrong homework! You need a little motivation to earn a release but for now this cage looks as cute as the helpless look on your desperate face. This film features white thigh highs, nude pantyhose, heels, stocking feet, lingerie, short skirts, cleavage, blowjob, footjob tease, stripping, pussy eating, female masturbation, tease and denial, chastity, cage, locked cock, face squirting, close up pussy cum, flirting motivation, and two twisted Femdom MommyDommes.

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Dommy's Degraded Sex Slave: Dirty Doggy Dick video from PaintedRose

Dommy's Degraded Sex Slave: Dirty Doggy Dick You've been patiently waiting to be needed and catch a glimpse of Dommy drying off after her shower. You can't help but stare and of course you get caught drooling like a a perverted pet puppy. Dommy has you crawl to her on all fours. "Normally, I would punish you" Today is a special day - the 1 year anniversary since you became my sex slave and degraded pet. Besides, you were just thirsty - open your mouth pet. Pussy free has been your agony that I have enjoyed inflicting but I want to breed and you're obviously full of virile slave sperm. I decide that you'll do for the job very nicely and you'll do it exactly how Dommy says. Dommy orders you to fuck all of her holes thoroughly and to breed and creampie her perfect puffy pussy. You are my forbidden fuck toy forever, Son. Happy Anniversary! Thirsty? This custom made film features; spitplay with swallow, leashed pet, orgasm control, pussy free release, switch control, breeding, toilet fetish, Taboo Femdom Step-Mom and submissive step-Son dynamic, MommyDomme pure slave agony and degraded humiliation. This film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. FemDommy KeyWords: Rosie, Painted Rose, PaintedRose, Goddess, Mistress, Step-mom, StepMom, Mom, Mommy, Mother, MommyDomme, Mama, Momma, Mom, Domme, Femdom, FemDomme, Sex, XXX, POV, Taboo, Taboo Sex, Roleplay, MILF, MILFY, Fetish, Depraved, Perverted, Kink, Suck, Fuck, degradation, verbal humiliating. cum control, orgasm denial, cuck, cuck-son, cuckolding, delicious FemDomination, spitplay, spit, squirt, leash, collar, pet, puppy, slave, slave training, agony, degradation, humiliation.

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Late For School: Mom's Sweet SPH Handjob video from PaintedRose

Late For School: Mom's Sweet SPH Handjob Step-Mom is getting your clothes out for the day when she looks and sees you masturbating your pee-pee. She is appalled and shocked and tells you to just hurry up before you're late for school - again! You're taking too long and ask Mom to see her titties to help you along and she decides to help because if you're late again she's gonna be the one in trouble. Mom shows you her boobies and butt while telling you to make that little thing cum. You're still taking too long so Mommy gives it a kiss for good measure and jerks it until you cum all over her tits and shirt. Thank you for this custom film. SPH, Positive Encouragement, Handjob, POV, Step-Mom Fetish roleplay fantasy.

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Wet Weekend: Step-Mom's Tease and Denial video from PaintedRose

Wet Weekend: Step-Mom's Tease and Denial Step-Mom has booked a mini vacay for the two of you and when you arrive to the hotel - the only room left is a big bed and Step-Mom refuses to let you lie down on the floor. She insists that it's ok to share and sends you to get your teeth brushed and pajamas on. When you come back you glimpse her just putting on her nightgown and can see her thong through it and you already are worried about managing your erection. Step-Mommy is cold and she cuddles you by rubbing her big butt into your crotch and you start to drip with an erection so hard you have to relieve yourself. You quietly start rubbing but, then she hears you and is shocked you would stroke it next to her.. for her. She feels bad when you confess it is the way she's rubbing and wearing a see through nighty. She tells you to hurry and finish because it's inappropriate and you're still taking too long so she begins to give you a handjob. Just when you're close, she decides she needs to cum - on your face since it's obvious you can't have real sex. She rides and grinds her sweet wet pussy on your tongue and lips and soaks you with an orgasm. She decides after that you need better control over your orgasms and tells you that you can not cum right now. She takes control by making you go to bed with an aching boner. Maybe she will ride your face again .. if you're a good boy. Thank you for this custom Film!

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Mommy Workout With Son - POV Fuck video from PaintedRose

Mommy Workout With Son - POV Fuck Mommy loves to workout and today you are here with her watching, drooling. Mom notices the bulge in your pants and asks if she can help. Mom gives you POV BJ, POV on top, POV doggy style. Mom tells you to CUM INSIDE! You also got in your workout today!

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Milk and Cookies: Hungry Good Boy video from PaintedRose

Milk and Cookies: Hungry Good Boy You're ready for your snack and so you go into Step-Mommy's room to find out what is taking her so long. She is changing and you've just seen everything. Her namkey Mommy body and you can't look away. She begins asking you what you saw and wants you to tell the truth. She tells you that you're a growing boy and it's normal for you to be curious about Mommy's Milky Jugs and Sweet and Yummy Cookie. Good boys love Milfy Cookie and you should have all you want because you are her special sweet boy. Thank you for being my very good boy. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Engorged: Milking For Step-Mommy video from PaintedRose

Engorged: Milking For Step-Mommy You and Step-Mom are taking a vacation together - you need some special one on one time. We can do anything you want for fun but, Step-Mommy needs to pump her breastmilk after such a long flight. I can't seem to get my milk to let down with the pump and I am getting so engorged with milk that my boobs are really hurting! Just then you walk in and when I explain what's happening, you offer to suckle to help out. After careful thought, what could be more natural then nurturing my sweet boy with warm sweet milk? I tell you to lean back on the sofa and I will straddle you to let gravity help the situation and because you're a bit too big for Step-Mommy's lap! You start sucking and my nipples get hard and begin to tingle. You enjoy Step-Mommys sweet milk and then I start moaning and accidentally have an orgasm from the nipple stimulation. Oooops - well thank you so much for helping me! A couple of days later, my big milk jugs are aching and so I climb over top of you and we begin to breast feed. When I feel your cock becoming erect under me, I slide you into my juicy, slippery Step-Mommy fuck hole for a double milking session. I hope I wasn't ovulating. 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. KeyWords: Step-Mother, Step-Mama, Blonde, Mature, Natural Tits, Fat Pussy. Phat Pussy, Thick, Juicy, Squirting, Squirt, Female Orgasm, Sex, lactating, Love, POV Sex, Horny, breastmilk, breastfeed, Kink, Suck, Fuck, Underboob, Curvy, Curves, Chubby, Big Lips, DSL, Rosie, MILF Rosie, Painted Rose, PaintedRose, Step-Mommy Milkers, Virtual Sex, Taboo Step-Mom, Cougar, Creampie, Cream Pie, perv, Sensual, Lover, Loving, Sweet, Seduction, Seductive, Sin, Sinful, Cunt, Step-Mommy Cunt, Fuckhole, Spit, engorged

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Cold Night Gets Hotter - Taboo Cougar Step Mom video from PaintedRose

Cold Night Gets Hotter - Taboo Cougar Step Mom This is a step-mom roleplay POV fetish fantasy . You realize the heat isn't working and wake Mom to ask her what to do. She is in bed and WOW her soft and warm skin looks so touchable! She wakes up and says she can't call the furnace guy until morning so you will just have to keep warm some other way. You ask to just get in her bed and she agrees and drifts off but seems to be having an arousing dream. She touches and rubs. Of course your dick is hard. You know you shouldn't watch but, you just can't look away. She arouses and is embarrassed. She was having a romantic dream and also notices your erection. After a thoughtful process, she asks if she can just see your dick. when she sees it, of course she wants more and you're ready to go anyway so when she teases you with her body, you innocently agree to let her ride it. She wants you to give it to her doggy, her on top, you on top, and then she wants filled and of course you're good to go and fill her up with a hot load of cum to warm her shaved, pink pussy. You both realize you stayed up fucking all night and lay down to cuddle some more. This is a gentle femdom roleplay pov virtual sex and custom video.

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Taboo Seed: Get Mommy Pregnant video from PaintedRose

Taboo Seed: Get Mommy Pregnant Step-Mommy starts telling you a story about how much she loved being pregnant and wishes she could get pregnant again! She tells you all about how she would need fertile seed to plant in her womb to grow a pregnancy. She tells you she would need boy sperm from a penis and how she only has a pretty pink pussy. Just then, she gets a forbidden idea and you're very curious about you might be able to help Mommy with getting pregnant. She says she would like to play a game to find out if you can breed her. She promises it's a really fun game and you will love as much as you love her. This film is a step-mom fantasy roleplay about breeding and impregnation, sex education, first time taboo, sweet loving experience with a side of filth talk. Slow burn edging to build a big first cum to impregnate Mommies fuck hole. Teasing, HJ, BJ, Creampie finish! A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Feminization Of Sissy Neighbor - Part 1 video from PaintedRose

Feminization Of Sissy Neighbor - Part 1 New neighbor visits you to return a mistaken delivered package - full of panties and frilly items. You deny being a sissy but, she gives you a task to start turning you into a sissy. Shaving, Wearing Panties, and jerking to hung daddy porn fucking sissies. We will check in for coffee in one week to monitor your progress.

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Time For Dick-Tation: Tease & Cum CD video from PaintedRose

Time For Dick-Tation: Tease & Cum CD Your new secretary walks in for her first day prepared to thoroughly do what you hired her to do and goes above and beyond your expectations from the get go. She tells you to pull it out because you're already stiff and she just knows what you need. She orders you to stroke for her lips, tits, ass, legs, and finally her mouth and tongue. At the end she counts down from 10 and sweetly orders you to empty your big load on her tongue. Who is in charge here? This is a feel good, light and fun, Jerk Off Encouragement video with Rosie sensually dominating you gently but firm. You're going to love it. Thank you!

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Little Dick Momma's Boy: Sweet SPH video from PaintedRose

Little Dick Momma's Boy: Sweet SPH You didn't ask to be born this way - as a little dick Momma's Boy. Step-Mom knows it's her job to tell you the truth after accidentally seeing your D-pics on your phone. You'll always be stuck living at home because you won't be able to keep a girlfriend ever with a penis that small. After making sure that you understand your place in the world of sex and humiliation for not.. measuring up, Step-Mom has some ideas about what to do with that tiny thing. SPH Small Penis Humiliation Affirmations, Humiliation, So sweet and so small.

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Secretary Revenge: Payback for Pussy video from PaintedRose

Secretary Revenge: Payback for Pussy You hired your secretary for more than her personal assistant skills unknown to her and you let her know what she has to do to keep her job. Later on she is sick of it. Your small softie, even with Viagra dick. Your arrogance and unfair demands. Your disgusting disregard for your wife or your secretaries feelings. Secretary Rosie is sick of your limp little cock rides and decides to end it and you. Your wife is going to divorce you when she finds out and you're gonna marry her. Don't worry, she might let you cum...sometimes. You're going to listen to Rosie now. She is controlling everything...your life, your finances, and your cum. This is a custom video. Gentle Femdom Roleplay. Financial Domination and Blackmail Revenge.

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Dommy's Degraded Sex Slave: Obedience Training video from PaintedRose

Dommy's Degraded Sex Slave: Obedience Training Today, Domme Mother tells you that it is time for your obedience training and you are ordered to take off all of your clothing and kneel on the floor in front of her. Pets have no use for clothing, hobbies, or education other than what Dommy provides. Your purpose is to serve and obey your owners every wish as a beloved pet and speak only when told to. Open your mouth pet - Spit, Swallow, Repeat! Now that your mouth is open you must train to suck my cock and cum like a good pet. Crawl away in shame for loving Dommy Dick so much! Lay on Dommy's bed and wait naked with your legs open anticipating the next time I will use and degrade my humiliated dick slave. You've earmed your collar and now I will have my way with you pet. You are powerless under my Dommy control as I take ownership of all of your begging holes with my strap on cock and mouth. Beg? Spit, Swallow, Repeat! Good Pet. This film features spitting into your mouth and making you swallow, cock sucking training, obedience school for pets, femme domination, leash and collar, slave training, pegging with strap on, blowjob, rimjob, cum on Dommy's tits finale. This custom made film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. Dommy KeyWords: Rosie, Painted Rose, PaintedRose, Goddess, Mistress, Step-mom, StepMom, Mom, Mommy, Mother, MommyDomme, Mama, Momma, Mom, Domme, Femdom, FemDomme, Sex, XXX, POV, Taboo, Taboo Sex, Roleplay, MILF, MILFY, Fetish, Depraved, Perverted, Kink, Suck, Fuck, cuck, cuckold, cuckolding, sph, small penis humiliation, degradation, verbal humiliating, spit, spitplay, pegging, strap-on, strapon, peg, leash, collar.

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Naughty Nurse Stamina Test and JOI Teachers Sissy Boy Detention video from PaintedRose

Naughty Nurse Stamina Test and JOI Teachers Sissy Boy Detention The nurse comes from the agency to perform your stamina test and right away tells you to get naked. Part of the test is the nurse stimulating, and assisting you to edge out and then count you down to cum with her once you've passed the test.The nurse starts by removing her scrubs and checking you for firmness and stimulating an erection. From there, it's her teasing you with her body, shaved pussy, and ass to edge without blowing too soon. She gives you very specific instructions for the jerk off part of the test. Once you've passed, it is time to have her count you slowly from 20 down to 0 to cum WITH HER. Nurse Rosie is hoping you can shoot far enough to hit her bullseye. JOI, Mutual Masturbation, Nurse Fetish, MILF, and Gentle Femdom Scenario.

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Pick a Pair: Sissy Girl Panties video from PaintedRose

Pick a Pair: Sissy Girl Panties Step-Mom asks you if you were going through her panty drawer because you want to wear them and she already knows. She wants to play a game to figure out what kind of Sissy you are. Pick a pair of panties; 1, 2, or 3. Mom already guessed it and wasn't surprised at all! You're my Sweet Sissy Girl. From now on, we will do everything together like girl best friends, including rubbing our sissy clit for a sissygasm! This is an interactive fantasy feminization roleplay.

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Mommy's Big Boy - Wittle Wee Wee JOI video from PaintedRose

Mommy's Big Boy - Wittle Wee Wee JOI Jerk that cute wittle wee wee for Mommy (step-mommy). What a cute little baby dick. You want to cum in your diapee don't you? Mommy shows you her boobies and butt for fun. JOI countdown. SPE. JOI. Mommy Roleplay.

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Doctor Cougar and the Physical Exam video from PaintedRose

Doctor Cougar and the Physical Exam Doctor Rosie has a new patient come in for a college physical. She decides he needs a very thorough physical exam. Sure, the usual stuff but, let's make sure the sexual health is normal. She starts with a shot to help him relax and ... medicinally assist in an erection. Shhh... He doesn't know why he is getting aroused. He is embarrassed. Doctor Rosie has him lie down and when she comes back, she is wearing just lingerie under her lab coat. She manually stimulates him to measure his erection but, the gloves aren't helping so she removes them. The Rosie decides he needs visual assistance and she shows him her breasts. Once fully hard, Rosie hops on and cums on his dick to measure optimal stiffness. Yes, he will do well on this exam. She realizes she can't send him home with a boner and decides to now drain him with a hand / blowjob. In the end she jerks his big volcano until he has a full eruption!

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Sweet Dreams: An Illicit Affair video from PaintedRose

Sweet Dreams: An Illicit Affair It's bedtime and also time to cuddle up and watch a Movie with Step-Mommy. You pick out a movie that's a little naughty and Mommy asks if you're embarassed to watch that stuff in front of her as he nipple slips out. She smiles and tells you that she really likes watching dirty movies with you. You've had a lot of sexual stimulation tonight and when Mom reaches over to put a blanket on you, her arm bumps into your very stiff erection. She explains that it's healthy and normal and asks if you get hard a lot. She says she'd better behave by staying on her side of the bed because she's really turned on after everything. You both start to drift off and then you feel her rubbing on your big meat while she writhes her body back and forth. She startles and says it must be a dream because she'd never ever touch her own Son's dick or take her tits out for him as she straddles you and drops rubs her Mommy pussy on your boner. She starts stroking and then sucking you slurping your precum like a thirsty naughty Mommy. She says you're still hard and she must have your stiff young meat inside her dripping Mommy cunt. She slides you in and rides it cowgirl and reverse doggy style while twerking on your hard on. She turns back around and cums a squirting Rosie-gasm on your dick and then takes your creampie inside raw. It's just a dream.. Isn't it? A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Christmas Cuckold: Big Boy Battle. Cuck vs. Bull video from PaintedRose

Christmas Cuckold: Big Boy Battle. Cuck vs. Bull It's present time and Step-Mom calls you both in for your gift. The only problem is Mom can't decided who gets which gift. Mom decided to make it a game. She tells you to both take out your penises so that she can decide who will be the Big brother and who will be the Little Cuck Brother. There is a clear cuckold winner and it is you! Step-mom goes on to tell you all about your new roles and has you release a few drops of cum before she locks your little dick in a cage. Big brother makes a nice pile...for you to eat. This is a POV Cuckold CEI, JOI Bull / cuck roleplay fantasy. Gentle Femdom Cuckson Virtual Simulation.

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Bad Girl For You - Cumming Together Video video from PaintedRose

Bad Girl For You - Cumming Together Video I am so horny and I want to be a bad girl for you and fuck this yummy pussy and us cum together so hard!

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A Good Boy's Storytime video from PaintedRose

A Good Boy's Storytime It's Storytime with Step-Mommy. This is a taboo tale of twisted tickles and touches. It was just the two of us and a cold night that turned into a heated horny all night novel of short sinful sagas. Chapter 1. Curiosity and Mommy's Cunt. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Classified Photographs: Mom / Son Mixup video from PaintedRose

Classified Photographs: Mom / Son Mixup Step-mom answers a classified ad for posing for lingerie modeling from a guy who says he has a small penis and just wants some pics to jerk off to. Mom needs the money and she does this sort of thing regularly although her son and hubby do not know. She tells the guy to meet at her secret place for doing her dirty deeds. To her surprise, it is you, her son! What? My son has a tiny sissy dick? Okay I need the cash so I will do it but your dad can't find out, do you have your camera?... I start posing and you offer to pay more for full nude, I agree. I pretend your not my son and start getting naughty. I'll still need to punish you, you little pervert. I need to go...so you want to watch and I make you do more than watch. We take more provocative pics and you get a little tiny erection. I still love you even though you have a tiny penis son. As your punishment.....You have to........... Gentle Femdom roleplay sissy boy small penis humiliation, JOI, CEI. This is a custom Video.

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Nurse Mommy: Stethoscope Heart Racing HJ video from PaintedRose

Nurse Mommy: Stethoscope Heart Racing HJ Step-Mommy gets home from her job at the hospital and starts stripping down not realizing you're in her bed. She thought she startled you and so she was checking your apical pulse with her stethoscope your heart rate increased even more! Mommy realizes you have an erection, a boner and asks you if it hurts. Since it is hurting, Mommy gets the lotion and jerks off your cute little winky and then tucks you into bed. Sweet-Dreams Love.

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Depravity: Fucking Perverts video from PaintedRose

Depravity: Fucking Perverts You walk in on Step-Mom touching herself and can't stop watching.. until she catches you with a boner for her. Later on, she tells you Dad is a prude and would never understand why you watched and jerked it to Mommy and says nothing else must happen. You're there around every corner with a hard on and sex deprived and depraved pervy Mom wants to make you chill out so she gives you a handjob and tells you to cum fast! Later on - again but a blowjob. She says this has to STOP! You can help yourselves - you're both depraved fucking perverts. You walk in on her in a nighty and she seduces you to bed her while Dad is out of town. Lots of HOT SeXXX follows with a creampie! A Rosie Original! This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Mom's Guidance: Sissy Daughter Training video from PaintedRose

Mom's Guidance: Sissy Daughter Training Step-Mom calls you in to say good morning and tell you about her wonderful idea to transform you into a beautiful, sweet daughter since you are already obviously feminine and she can see it was meant to be. You decline at first but, Mom talks you into doing it to spend more time together, bond, and become your true self. As I begin to unveil your gifts, it becomes clear as you feel complete as you begin your daughter and sissy training. In the end, you get a shiny pink buttplug for your sissy pussy. This is a gentle femdom, loving, guidance roleplay video.

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Prop Dick Guy For Step-Mom video from PaintedRose

Prop Dick Guy For Step-Mom You accidentally see Step-Mom setting up between scenes. It's just you and Mom and she had to start doing adult work when Dad left. Things are hard but she's always doing her best to take care of you. Today she says she's having trouble getting the right angles with her new camera and asks if you could hold the camera - since you already walked in and saw her in lingerie. You are excited to help especially because it means you can spend time with Mommy and secretly you don't know why but you really like looking at her in her work costumes. She is shooting something called a, "Mommy Fetish POV" and so you have to hold the camera close while she backs her butt up close to the lens - she says to just hold the camera and try to not laugh at all the dirty words she's saying. She starts talking about "Fucking her own Son" while twerking and you can't help the feelings that are happening down there and then her fat ass bumps into your stiffy and... Thank you for this custom video! This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Ransom and Self-Hostage Bondage Humiliation video from PaintedRose

Ransom and Self-Hostage Bondage Humiliation Rosie Hijacks Chris's whole life of sissy secrets through his PC. She sends him a self kidnappping kit. He is manipulated, blackmailed, and must comply with her orders to wear girl panties and a bra and urinate on himself as punishment for noncompliance. He didn't know it was being live broadcast to all of the internet. Custom Script and Video by Chris (pantyprisoner). Thank you!

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Get A Clue: Mommy Edition 4K video from PaintedRose

Get A Clue: Mommy Edition 4K Step-Mommy has a new game for game night and it's called, "Get A Clue: Mommy Edition" Sounds fun right? Little do either of you know, it is a taboo mystery game. Mommy is so playful and says that you both need to finish the game and taunts you that she's going to win. You take turns rolling the dice and guessing. " Cougar Mommy in the Living Room with a Missionary Creampie" ?? Oh the suspense! How will it end? There are four complete POV Step-Mommy scenes! Sweet Mommy In The Backseat with BJ and Reverse Cowgirl and missionary creampie! Mean Mommy in the Den with Pussy Eating, Handjob Tit Spray. Cougar Mommy in the Living Room with a Missionary Creampie and BJ! Last but not least.. Horny Sexy Mom in the bedroom with all the positions and another delicious dripping creampie! A Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

^$16.00 Add to Cart

Home Sweet Home: Step-Mother's Vagina video from PaintedRose

Home Sweet Home: Step-Mother's Vagina You must be in Step-Mommy's bed for a reason? I was looking for you to give you a kiss goodnight. Without Step-Mommy's loving hugs and kisses you might not have sweet dreams so pucker up buttercup. You like my kisses don't you? I already know because your little guy (your cute penis) is standing straight up - waiting to come home - to Step-Mommy. Home sweet home to that special warm place that feels so safe, wet, tight - like a bearhug between Step-Mommy's thighs. MommyDomme is so proud of you for getiting such a big and stiff erection and in fact that penis belongs to Step-Mommy.. just look at how hard you are for me. You won't be permissted to touch it or let other girls touch it becasue only bad boys run away from home and my Step-Son is NOT a bad boy, is he? No, of course not. Do you understand the rules Step-Son? The punishment / reward for a big boner is for Step-Mommy to take it away inside of her vagina. Watch this trick as I make your stiffy cock disappear inside of my perfectly pink Step-Mommy hole. Look at how nice your penis fits inside going up and down up and down.. Do you like my big Step-Mommy milkers hovering over you bouncing?Just let it all go Step-Son. Step-Mommy knows. This custom made video features POV taboo roleplay, MommyDomme Fantasty, Cum Control, First Time Sex Ed, Underboob, Cum Inside Creampie, Dirty talk game, curvy body teasing, kissing, mind fuck, Step-Mommy Fetish Introduction and addiction. This film is a solo performed adult roleplay fantasy that is 2257 compliant. Please rate this video 5 stars and please leave a nice review. DM me to order your own Custom video. Please subscribe and follow for all behind the scenes and so much more! Thank you SO MUCH! Hugs and Smoochies, Rosie. *************************** KeyWords: Step-mom, StepMom, Step-Mom, Step-Mommy, Step-Mother, MommyDomme, Domme, Femdom, FemDomme, Blonde, Mature, Natural Tits, Fat Pussy. Phat Pussy, Thick, Juicy, Squirting, Squirt, Female Orgasm, Sex, Step-Mommy Fetish, Romantic, Love, Drama, Story, Bundle, POV Sex, Horny, Insatiable, Depraved, Perverted, Kink, Suck, Fuck, Underboob, Curvy, Curves, Chubby, Big Lips, DSL, Rosie, MILF Rosie, Painted Rose, PaintedRose, Goddess, Mistress, Virtual Sex, Taboo Step-Mom, Cougar, Femdom, Nurturing, Cum for Step-Mommy, Good Boy, Step-Mommys Good Boy, Creampie, Cream Pie, Lingerie, Sensual, Lover, Loving, Sweet, Seduction, Seductive, Sin, Sinful, , Facial, Cunt, Step-Mommy Cunt, Fuckhole, Shaved, Cum, Come, Big, Tits, Titties, Tittys, Boobs, Boobies, Breasts, Nipples, Suck, Cock, Dick, Swallow, Step-Mama, Step-Momma, Step-Moms, Cowgirl, On Top, From Behind, Caught, Panty, thong Panties,

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Taboo Touching: Claiming Mom's Pussy video from PaintedRose

Taboo Touching: Claiming Mom's Pussy You and Step-Mom have been flirting with Taboo play ever since she saw your erection and when Mom asks you what you'd like to do tonight she is not that surprised at your answer. You tell Mom that you want to FUCK and CLAIM her PUSSY as yours tonight! She tells you that she can't, it's ... taboo ... You continue to convince her why she should be the first to feel your stiff cock and you guilt her with the, "Don't you love me Mom" line. Mom decides that if you're going to claim her pussy that you need to be trained to do what she wants and how she likes it! Mom teaches you to fuck her better than any man. She tells you to smell and taste it, fuck it from the back, and she rides you until she demands you to cum inside. This femdom fetish film is an interactive fantasy role play of Mommy Fetish, Taboo, POV Virtual First Time sex.

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Mommy's Has A Date - Son's Dick video from PaintedRose

Mommy's Has A Date - Son's Dick Step-Mommy has her first date in such a long time. She's nervous and feels like she's lost her confidence. Son Jonathon gives opinion that her nipples are too easily seen through her shirt. She realizes that the shirt may be inappropriate she doesn't want to give off the wrong message. He offers to rehearse a date since she is so nervous so they do this. It loosens Mommy up and she starts asking more provocative. Finally rehearsal turns real with a simulated kiss and she invites her, "date" back to her place. "Cum For Mommy"

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Feminization of Sissy Neighbor - Part 4 video from PaintedRose

Feminization of Sissy Neighbor - Part 4 Our weekly training session is also a new beginning. Now that your Sissy training and transformation is almost complete, I brought you an outfit and help you get decked out with make up and some Hot spicy red panties. I have a surprise for you honey, I set you up on a blind date! Well it's a double date and I won't leave you unless you ask me to. He's a hot long Dadddy with a Dadddy Dick to match. Don't worry, you are his type! I'm so excited about my new girlfriend and our special night out!

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Taking Sneaky Sexy Video On Your New Phone video from PaintedRose

Taking Sneaky Sexy Video On Your New Phone You've been watching your Step-Mom tease you for weeks and then you usually jerk off thinking about her. Today - your new phone came in the mail and when you got home - Step-Mom had it all activated and ready to go. She said she took a funny video for you and laughs as she walks away to run a hot bubble bath.. The film begins as you open the video and see Step-Mom stripping out of her clothes, sexy dancing, sucking a fat dildo, twerking, removing all clothes, fingering herself, sensually teasing you, up close orgasm in your face and then cum inside of Step-Mommy.

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Photoshoot with Hung Stepson Turns XXX video from PaintedRose

Photoshoot with Hung Stepson Turns XXX Rosie has a photo shoot with Her step-son photographer when Dad is out of town. They’ve gotten too close. Her top slips and he fixes the strap but can’t resist to start to squeeze the tits his dad loves! This young man becomes her secret intimate lover on this day. Very steamy and romantic. Many sexual positions and finally a long 69 cumshot scene for both. You can hear the liquid squirting on his face while he finger bangs G-spot and eats my pussy with me sitting on his face and then he cums in my mouth! Squirting, blowjob, Doggystyle, 69, oral sex on banister, cowgirl...Shooting is not POV rather, different angles that give you HOT views of the Romantic Sex. Male doesn't Talk Much, He FUCKS for POV Virtual HOT Sex.

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Don't Go: Stay With Me Mom - Son's Lust video from PaintedRose

Don't Go: Stay With Me Mom - Son's Lust Rosie has a date tonight and her son doesn't like her outfit (It's too revealing) and in fact tells her he wants her to stay with him. She says she needs a man's touch. Son tells her he can do anything her date can do and more. She says she loves him and he's special to her but she is going. She hugs him but then feels his huge hard on in his sweats and and when she looks at him, they start to kiss. She then gets so turned on and starts to blow him. She gets on top and rides his stiff boner. She loves it. She gets so dirty telling him how to fuck her wet pussy. She tells him to lick her pussy until she cums in his mouth! Instead he fingers her gspot and makes her squirt before letting her orgasm in his mouth. She sucks his fat dick again! His cock is aching to cum in Mommy so he beds her over and bangs her hard and cums inside while her tits sway back and forth. Ending in creampie close up! She cancels her date. POV Son / Mom Roleplay!

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Blue Persuasion HD video from PaintedRose

Blue Persuasion HD The 4K version of this video being an hour long was too large of a file for APC.. but if you would like 4K after buying this, I can send you a DL link. This is a fantastic film. A Rosie Original Script and performance. It's just been you and Step-Mom for three years and you're closer than most couples. You're testosterone is making things really.. blue - blue balls while you're Mom can't stop from being persuaded by you're huge boner in sweatpants. She decides to try to masturbate more and you go to your room to stroke off due to yet another accidental nip slip. It isn't working.. it's like eating an apple when you really just want some cake. You come to the conclusion together rather frantically that maybe if you jerk eachother off that you can get it out of your systems. You end up cumming all over your Mom's huge tits which she licks it up and says you shouldn't do it again. That night, you come up to lift weights and what the fuck is she wearing?!? Her sexiest dress which she drops and tells you to get on your knees to please her pussy with your mouth as a punishment for not taking off those gray sweatpants! You do so good at making her pussy drip that she blows you and takes a facial before telling you it has to be the last time. You don't care - this has already gone too far to ever go back - she's ruined you for other girls. Later on, you stand before her - throbbing cock and a determined young body eager and ready to please her and learn every inch of how she feels, smells, and tastes. The Fuck Finale with eating pussy from the back, doggy style, reverse and front cowgirl, missionary, both on top, underboob, tit cum play, cumspray, oral, facial, Mom squirting, and 2 blowjobs finish her. Surprise ending. 1 hour long with 10 minutes of Behind The Scenes!! 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.

^$19.00 Add to Cart

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