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Paintedrose – Mommys Yoga Pants 1st Boy Boner HD 1080p
You and Mommy are having a stretch and tone afternoon and she’s wearing yoga pants with a thong! Mommy doesn’t know that you look at her butt when she is exercising and that you don’t really understand why you can’t look away. After some stretching, you tell Mommy you are hurting – down there and she is surprised but explains everything and how it’s ok. Mommy teaches you how to make it stop hurting by demonstrating a handjob and how to masturbate. She said it’s special between you that she be the one to teach you about your first time and then she starts acting different – flirty and ‘turned on’ as she called it. She says she can teach you lots of fun things and you agree as she’s popping off her top and yoga pants.
MILF, Mommy Roleplay, POV Sex, Taboo, Workout
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Your Mom’s A MILF Sharing Is Caring HD
You have a friend over for movie night and snacks from school and he’s really cool and older then you. While he’s finishing his pizza, you tell Mom that he said you’re a MILF. She explains your friend just think she’s a cute girl – no big deal. Movie night is awesome but you get sleepy and so Mom send you to bed. You heard a loud noise and woke up and saw then doing sex on her bed. They were licking each other’s private parts and he was putting his big pee pee inside of your Mom and she was making noises. Watching gave you a feeling of pressure and you started rubbing and pushing on your own penis. Just then, Mom comes out and is surprised to see you there. She asks if you liked what you saw and you nod yes. Mom begins sucking on your penis like a lollipop. She tells you she doesn’t want you to feel left out and that you have a beautiful penis. It’s not as big as his because you’re still growing. Mom asks you to watch her make your buddy cum again to teach you how. You give Mom a mouthful and your first facial.
MILF, Mommy Roleplay, Taboo, Virtual Sex, XXX Hardcore
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Paintedrose – Sissy Girl Clit Cuckolded by MomBull HD 1080p
Son’s Sissy Girl Clit Cuckolded by curvy Mom and Bull Cock – Mom Rosie accidentally walks in on her son masturbating and sees that his penis is only 3 inches hard. She calls him in to talk and tell him not to be embarrassed but realize he is a sissy. A Sissy girl with a girl clit cock. He isn’t a real boy, or man. Though reluctant at first, she teaches him to be her daughter with training and make up. Mom has his big cock friend fuck her in front of her new daughter to show her why she can never be a man. She makes her daughter lick the cum off of her tits after the big cock sprays her mouth and tits after a vigorous, dominant fuck. She wants her new daughter to get a taste for cum. Big Daddy cock cum. Her sissy daughter is so turned on from watching mom get pounded by a real man, that she wants to use her clit cock to fuck mom. Mom agrees because she loves her daughter. Mom can’t feel a thing, it’s comical the humiliating attempts of her daughter to have sex…making stupid faces and noises. Mom is insulting and humiliating while still being loving. Custom Video.
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MommyDomme Initiation Sub Training – PaintedRose HD 1080p
Mommy found out that you didn’t dump that girl at school. Surprise – Homeschool. Lies – Filthy lies 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 Mommy-Domme 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!
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Paintedrose – Do It For Dad: Taboo Impregnation HD 1080p
Mom comes in to find you tired and resting on the sofa. She apologizes for the noise from the squeaky bed. She tells you Dad has been trying to get her pregnant for months with no luck. She tells you a secret that she doesn’t think she will become pregnant because old Dad can’t stay hard and rarely is able to ejaculate. You wish you could help and just then, sweet Mom has a great idea that you should knock her up and do it for dad to make him happy. After all, you look just like your dad and he’d never have to find out and be hurt by it. You feel guilty but she pops off her top and starts to suck on your hard dick and becomes a wild primal lusting for your cock and cum. Dad can’t find out! She’s wearing a thong and pulls it to the side and rides your stiff one from the back – you’ve been fantasizing about this for years and now it’s happening! She wants you to breed her and lays on her back to take your taboo love seed and get pregnant. She begs and demands that you CUM inside of her. She suggest you be ready for more ‘trying’.
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Paintedrose – Mom’s Lesbian Sissy Daughter Training 4K
Mom Dommy walks in your room to ask you if you’ve seen her pink swimsuit.. but you’re wearing it and she sees your tiny private part poking out. Mom has a talk and tells you that she’s known about you wearing her cute panties, bra’s and sexy stuff for quite a while and she’s glad it’s finally exposed and out in the open. She tells you she is going to re-raise you as her sweet girl. Mom knows that you’re a virgin and will never be able to fuck a girl with that tiny clitty and that also you need to focus on becoming a girl and so she gives you a special gift – a chastity device! Mom puts it on you as she explains that this is the only way she can really raise you as her sweet girl. M-Dommy also explains how you will still have pleasure from your clitty with sissygasms once you learn to give Mommy orgasms with just your mouth. You’re Mom’s sweet lesbian sissy girl now and MomDomme sits on your face and cums all over your pretty little mouth. The cage is a little tight now and Mom pulls out some special presents while stripping and putting on her Mommy dick strap on to make your clitty feel better. This was a very fun film to make and I know you will love it sweet girl. Slightly humiliating and sweet as you step into the magical world of pussy power. Thank You for this custom video!
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Paintedrose – Matching Pajamas Your 1st Big Boy Boner HD 1080p
It’s Christmas Eve and that means you get to open one present! Guess What? Mommy got the same pajamas – let’s get changed and wait for Santa! You accidentally see Mommy changing and then your little pee-pee started to feel funny. In bed, when Mommy notices and asks if it’s ok she tells you you’re NOT on the naughty list and it is NOT your fault.. Sometimes these things happen when you see something that excites your cute little pee-pee. It’s hurting so Mommy teaches you to masturbate. She get’s so turned on that she crosses the line of no return and teaches you how to do sex.
Christmas, Dirty Talking, Mommy Roleplay, POV, Virtual Sex
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My Husband – My Sissy My Cuck My Wife HD
Your loving wife goes along with all of your roleplay ideas about her pretending to fuck and get She is shocked when you say you’re going to have a vasectomy and you want her to find a bull to get pregnant by. She needs time to think about it, she loves you. While doing household chores, Rosie stumbles upon your makeup, panties, and your porn history about cuckolding and feminization. Rosie realizes a loving wife will do whatever it takes to make her husband happy. Rosie beings the process of giving you special female hormone protein shakes without you knowing.. at first. She finally finds a nice big man to date and she brings him home to fuck with you watching – you must eat his creampie and clean it up. You spend your days and nights fluffing Rosie and her new Stud Cock. Your body is changing and Rosie reveals to you why you have these new curves and sexy body, she’s been sneaking you hormones. Rosie tells you that you will start wearing lingerie, make up, and how it will be – you will keep your dick so she can still fuck you, but you will be her wife and co-mom for the babe she is now pregnant with. Multiple wardrobe changes, M/F fuck scene, POV Feminization and cuckolding, Impregnation fantasy, Cum Eating, POV Virtual Sex.
#Cuckolding
#Femdom
#Feminization
#Impregnation Fantasy
#MILF
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Grandmas Cookies Fuck Boy Training HD
Your Mom sends you to live with Grandma because you were sexually aroused by her panties. Good thing for you, Grandma doesn’t mind you being a little pervert and in fact she loves it! Grandma let’s you watch her shower, and bake, and gives you used panties to sniff. You’re Mom has always been a prude but, Grandma truly understands and that’s why you’re her favorite. Grandma says in exchange for taking care of you, that you are going to take care of her too. She wants you to serve her sexually. Licking, sucking, and kissing all of her private parts at her command. You do want your good boy rewards, it’s a lot more than delicious cookies. This is a POV GILF Virtual Sex roleplay. In this film, you will train to be my sweetheart and be rewarded for good behavior.
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Bathtime Babysitter POV Washing HJ BJ HD
Rosie is your fun babysitter. Really FUN Babysitter. Really a bad babysitter…Rosie gets naked too since she doesn’t want to get her clothes wet. She notices you looking at her soapy jiggly breasts and has you touch them. You’re reluctant at first…but, Rosie knows how to make you relax. She tells you to move your hands so she can wash your penis. She says that you have a very nice penis and she likes it. It hurts when she is washing it, a new kind of pain and pressure so she gives you some kisses to make it feel better and then a blowjob with swallowing. She tells you this has to stay a secret and makes you promise not to tell. POV Cougar MILF video with use of small dildo.
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Paintedrose – Dads New Wife Blackmail Blowjob HD 1080p
Rosie is your new Step-Mom and she’s working out ok but, you have other ideas for her. She’s headed out for the evening while Dad is out of town and she asks do you need anything and has a little heart to heart chat about trying to be a good Step-Mom. She comes back late and you know exactly where she was – out dancing and not with her girlfriend. You catch her coming in late and try to blackmail her for a blowjob. Rosie is one step ahead of you. She tells you to show her your dick and if she likes it, she will suck it. Rosie gives you the blowjob of your life and then turns the table on you with news that she received your report card in the mail. Rosie orders you to her bedroom because she has plans to NOT tell Dad about your grades.
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Paintedrose – Mommy Masturbates Too HD 1080p
You go into Mommy’s room and see her touching herself and rubbing and making noises. You’re very surprised but, you keep watching. When she notices you watching, she is startled and has a discussion about it. You tell her that you do the same thing and that you feel like doing it now. She is surprised that you do this already and tells you to go ahead if you need to. Just then, Mommy asks if she can touch it. This leads into her putting her lips on you and teaching you about a blowjob. Next she teaches you to lick her..down there. Then she asks you how you would like to do it next. You want inside her special place and she let’s you and loves it.
Solo with mom roleplay, some pussy rubbing, virtual handjob, oral, she uses a dildo for virtual blowjob, some dildo fucking in missionary, ends with virtual creampie.
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Horny Cougar Squirts In Your Face HD
Church Friend Brother / Brother Roleplay POV with Up Close Squirting. I’m a widow but, I’m still a woman with naughty desires and carnal lust.. I know it’s a sin but, I’ve been masturbating while thinking of you. You feel guilty for even getting turned on, it’s a sin… I tease and tempt you with my body showing you how I masturbate while thinking of you. I pull my panties to the side and show you my wet, slick pussy. I then ask to see it, I’ve always wanted to see your dick. I suck you off and swallow like a pro. Then it’s your turn to orally please me until I cum. Very close up squirting gushing orgasm with pulsating clit contractions. This is a lovely custom video. Roleplay, Church, Brother, POV Oral Sex, First Time, Taboo, Femdom.
Category: MILF, Oral Sex, Religious, Squirting, Taboo
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Paintedrose – French Kiss: Your First MILF Pussy HD 1080p
Your best friend’s Mom runs into you right after your workout in the home gym and offers you a protein shake and some muscle building advice. She thinks you look great, so grown up and asks if you can help her move a heavy package. Afterward she wants to give you a tip but says she will have to give you a kiss instead since she doesn’t have any cash right now. She is definitely flirting and asks you not to tell her son and says you’re her favorite boy in the neighborhood. She goes right down to give you another kiss – on your penis! She says it’s a french kiss but you know what’s happening – she’s gonna blow you – and she does.
Cougar, MILF, Older Woman / Younger Man, Taboo, Virtual Sex
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Sinful Sleepover Moms First Threesome 4k
You and your best friend are home from college hanging out and having a pajama party like old times. Your buddy tanks out early and you over hear moans coming from his Mom’s room. Later on – you run into Mrs. Flowers in the kitchen and she invites you to hangout in her bedroom since her son crashed early. You guys chat a little when she starts getting flirty. What the hell, she’s practically falling out of her tiny nightgown and you see her nipples. Next thing you know, she’s sucking your cock but tells you her son can not find out! You promise not to tell. You’re going at it, oral sex, cowgirl, doggy-style and then your buddy catches the two of you. Mrs. Flowers keeps fucking you and tells her son NOT to tell Dad! She tells him to join in for keeping the secret. You and your buddy fill up Mom’s lovely mouth and pussy with cum!
Cheating Wife, MILF, Mommy Roleplay, Taboo, Virtual Sex
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Paintedrose – MORE TABOO Vids in POV HD 1080p
Secrets In The Dark Taboo Auntie HD
Auntie is house sitting while your parents are out of town. One late night of hanging out turned into passionate all night sex education all week and now your parents are coming home early and Auntie says she doesn’t know when you can be together again. You’re struggling to rest and Auntie comes in and asks if she can lay with you because her room is cold.. and.. and.. she misses you. You two decide to just cuddle but you start kissing and touching while spooning and then she sucks on your tongue like it’s your dick. Next thing you know you decide to just make out but you’re stiff as a rock so Auntie can’t resist putting you in her throat. She loves you – and your stiff cock. Auntie needs you inside and says that she has to be on top because otherwise your parents might hear. She tries to be quiet but the bed is rocking and you’re struggling to contain yourself while she has to cover her mouth to not holler out when you orgasm together with her on top!
Caught, MILF, Mommy Roleplay, POV Sex, Taboo
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Moms Red Dress Taboo Love Affair HD
Mom Rosie is getting ready for a date and can’t decide which dress to wear and so her son offers to help. She changes behind the curtain into three dresses and has her son pick the dress. He can see through the curtain and saw everything, unknowing to Mom. He chooses the red dress and as Mom gets the call that her date is cancelled, she notices her son’s erection! Mom confesses her attraction to her son too. She is overcome with passion and begins to suck her boy’s cock and has him do the same to her. She teaches him what she likes and then climbs on him and fucks him with her tits in his face. He loves it and missionary creampies his mother and they confess their forbidden love.
Femdom, Mommy Roleplay, POV Sex, Taboo, Virtual Sex
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Mommys Has A Date Sons Dick POV HD
Mommy has her first date in such a long time. She’s nervous and feels like she’s lost her confidence. Son 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. Mom has all the confidence with Jonathon her son date. Does she decides to cancel her real date!
Femdom, MILF, Mommy Roleplay, POV, Taboo
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The Deal One Time And Dont Tell Anyone HD
You walk in to see Mom cleaning with no panties and a short skirt. She usually at least has panties on and now you can’t hide your erection any longer. You tell your Mom why your face is red, you’re embarrassed because of your erection. She feels terrible when you tell her that it’s her outfits and that you tried to look away but that it is her fault. Mom feels so bad that she tells you that you need to masturbate to feel better and get the erection to go down. You ask if she can help by letting you look at her posing for you and she reluctantly agrees as she knows now that she should have dressed more appropriate in front of you. Back in Mom’s room she is deciding whether to go through with this and begins to dance in her lingerie and then you come in and talk her into helping you since you’ve never seen a real girl naked before. You ask Mom to pose, and then show her boobs, then pussy, then ass. You tell her you want to touch her pussy with your dick and she then agrees but before you know it, you are fucking Mom doggy style and then ask her to ride your dick like the girls do in porn films. You ask Mom if you can cum inside of her and she tells you that it’s already gone too far and this will be the first and last time!
Femdom, MILF, Mommy Roleplay, Taboo, Virtual Sex
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7 Days Moms Taboo Tease And Denial HD
You recently spent time with casts on your arms and Mom had to take care of you for the last three days. She was constantly teasing by changing behind the sheer curtain and occasionally stroking you to release some tension – not enough to cum. Now you got your Casts off! Wait – you don’t want this to end. You’ve enjoyed this little game with Mom. When Mommy notices that you’re sad, she has a plan and an idea on how to continue. She tells you that the only way she can continue to tease and touch you, is for you to wear a chastity cage and she will continue when and how your cock is allowed to be erect or cum. Shall we say 7 days of teasing and a surprise at the end?
MILF, Mommy Roleplay, Orgasm Denial, Taboo, Tease & Denial
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Mommy Girlfriend Taboo First Time HD
Mommy is working out and has you join in and gives you a smaller set of weights. She’s impressed with how strong you are and asks to touch your muscles to see how hard they are but, then Mom notices your hard penis! Mommy tells you to not worry and that it’s normal. She suggests if it is hurting to start rubbing and shows you how. She resumes her workout but as she gets hot, she begins removing clothing and you get to see it all while she is doing various poses and movements. Mom encourages you to keep rubbing the pain away but then she gets closer and watches you with delight. Mommy tells you that she’s going to be your first girlfriend as gives you a handjob. Then she leans back and has you stick it in the special love hole. Mommy teaches you how to fuck and cum inside with taboo dirty talk and a wet shaved pussy.
Femdom POV, MILF, Mommy Roleplay, Taboo, Workout
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Moms Pantyhose Orgasm Cougar Bait HD
Mom returns from divorce court wearing her wedding shoes and seamed suntan pantyhose. It’s final – that bum is out of our home Son and I promise there will be no more dudes here besides you! You’ll have to start helping out with some things around here like helping Mom with personal chores such as making her pussy orgasm 5 times! Mom begins to undress and leaves on the heels and hosiery. She rubs and plays and squirts for you telling you that she’s doing it for you and she wants you hard for her. These pantyhose are for you son – have a taste of the gousette.
MILF, Pantyhose, Mommy Roleplay, Taboo, Squirt
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Moms Dirty Panties Creamy Wetness HD
After a long day at the hospital, mom walks in and sees you with her panties wrapped around your.. your penis. What’s going on son? I didn’t know you were turned on by me. A very devoted Mom suddenly realizes her son is a man. She’s been walking around in panties and bra in the hot summer not realizing she’s giving her son boners and a panty fetish. She realizes it’s her fault and she decides to remedy the situation by taking care of her boy in all ways. You like panties, smell these ones I am wearing instead. In your face Mom shows you how she rubs the lace and gets them all wet. She takes your dick and sucks it and tells you to take her to the bed like a man. Cowgirl, doggy, missionary creampie! Mom is orgasming throughout from your stiff penetration. She eats your creampie off of her fingers and gets so turned on that she fingers her pussy until she cums one last time for you and makes YOUR panties ever wetter for you.
Cream Pie, MILF, Mommy Roleplay, Panty Fetish, Taboo
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Moms Christmas Coupons Kiss Suck Fuck HD
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?
Christmas, Femdom POV, MILF, Mommy Roleplay, Taboo
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Mom Does It Better Than Your Girlfriend HD
You bumped your head and go into a dream state and have a hot fantasy about your nurse mom. She wakes you while wearing a seductive outfit unlike her normal work scrubs and just when it’s getting good, you are awoken by Mom in her regular scrubs. You tell her that you bumped your head while getting ready for a date with a girl. She realizes that you’re not acting normal and does a full investigative exam on you and your penis – just to make sure everything is working as it should. Mom tells you she knows your body very well and how it works and bets she can make you cum faster than you jerking or fucking your girlfriend. Mom makes you cum three times! Too bad there is nothing left for your girlfriend. Bonus scenes at the end.
Femdom, MILF, Mommy Roleplay, Nurse, Virtual Sex
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