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Showing 1-60 of 596 Results

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

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

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Mesmerized: To Get Fucked and Eat Cum video from PaintedRose

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

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The J Files: Vintage Sensual GFE video from PaintedRose

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

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Sissy Sister Wife: Bull Cock Threesome video from PaintedRose

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

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Confessions Of A Cock Craving Cougar video from PaintedRose

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

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Home-wrecking Sister In Law Seduces You video from PaintedRose

Home-wrecking Sister In Law Seduces You Rosie isn't just your Step-Sister In Law but, your accountant. She saves you from owing taxes again this year. You start to discuss that your wife doesn't appreciate you or take care of you the way a man needs it. She tells you that she always liked you from the first time she saw you at that party years ago. She still likes you. Rosie seduces you with her mouth and body!

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ABDL: Quick Change and Cum w/ Mom 2 video from PaintedRose

ABDL: Quick Change and Cum w/ Mom 2 Step-mom notices you need changing. Equipped with all of the essentials, the clean up sweetly begins. When I notice how stiff you are...knowing that it hurts, I decided to playfully take care of that by rubbing and wiping until you make cummies. Loving, Sweet Mum / Step-son interaction and play time.

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Mom Consoles Son video from PaintedRose

Mom Consoles Son I come home to find a sad faced young man. I console you and remind you that girl was no good anyway! Mommy can do all the sweet things for you. I reveal knowing how much you're attracted to Mom and tell you that it's natural. Show Mommy that you love her. POV AP CFM

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

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

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Panty Party: Sissy Slut Girl Games video from PaintedRose

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

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Mommy and Son Help Dad CUM In Condom video from PaintedRose

Mommy and Son Help Dad CUM In Condom Step-Mom calls you in to start helping her Hubby in the family business. Step-Daddy has very special sperm/semen and supplies it and needs help cumming. Mommy will stroke and suck Dad today into the condom while you train to assist with holding supplies, getting needed items, and opening the condom wrapper, and then helping with packaging Daddy's semen to be mailed...Shesucks and teases Dad to get his big dick to full size. During Jerking Dad into the condom Dad need to squeeze Mom's boobs and he finger bangs her pussy (you can see his hand up her dress and hear splashing when he gives her a g-spot orgasm!) She continues sucking him off until he cums in the condom. Mommy cleans Daddy's big dick lovingly with her mouth. Then you learn how to package the condom up in the ice for mailing. Good Job SON!

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Body Swap Transfer: Mom Vs. Wife Fantasy 2 3 video from PaintedRose

Body Swap Transfer: Mom Vs. Wife Fantasy 2 3 You are laying in bed and waiting on your wife. Your Mom (Stepmom) walks in instead and starts acting provocative and sexy. You're freaking out. Mom Stop! Then she busts up laughing and says she is your wife and did a body swap with your busty, curvy mom to do a role play fantasy with you! She says she knows how you're attracted to women who look like your mom and thought you might want to try some big boobs - petite curvy body for a change. She changes into something a little sexier and comes back for a fantasy roleplay. She kisses you, rides you, fucks you, has you cum inside her shaved wet pussy! She reminds you how much you liked her boobs when you were little while you make them bounce around! She tells you to CUM INSIDE SON! You bust your whole sac inside of Mom ! POV Virtual Sex. This is a custom roleplay Fantasy!

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Aunties Pantyhose: Pussy Play and Fuck video from PaintedRose

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

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Rosie in Thigh Highs and removing for Footjob! video from PaintedRose

Rosie in Thigh Highs and removing for Footjob! Curvy Rosie starts out with heels, thigh high's and then they come off to a hot dildo foot job with oil and lotion!

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

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

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Mommy Blows Big Cock W/ Son Watching 2 video from PaintedRose

Mommy Blows Big Cock W/ Son Watching 2 cuckolding - big cock, little cock (Dildo)

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Mom's Masturbation Lesson: Edging / Squirting video from PaintedRose

Mom's Masturbation Lesson: Edging / Squirting Step-Mom accidentally caught you stroking... she didn't know you did that yet. Mom was so turned on that she went in her room and sensually and erotically touched herself thinking of your young cock. Later on you come and and have questions. Mom doesn't want you to learn it wrong so she decides to teach you about proper erotic masturbation. She teaches you about edging and squirting today. She says you can't fuck her yet, but you can masturbate with her for visual stimulation to learn how to edge. Mom wants you to have a huge volcanic eruption. She sucks on her little dildo in front of you and then starts showing you her tits and pussy. Mom fucks herself for you and encourages you to jerk to her and you two cum together. Mom has a little squirting orgasm and then a HUGE SQUIRT that sprays you with her very real and powerful properly edged orgasm! You cum with Mom and it's amazing, She kisses you sweetly after you're done cumming. Mom / Son Fantasy Roleplay, Taboo Fetish, Gentle Femdom, Cougar Mom, edging and squirting. Mutual masturbation.

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You're Mommy's Little Girl Now video from PaintedRose

You're Mommy's Little Girl Now Since I married Daddy and became your step mom, I've been thinking of ways for us to be closer and the only thing that will work is if you become my daughter. No more leaving the toilet seat up and muddy tennis shoes. From now one, you will be a proper young lady. I've already gone shopping and have some frilly pink things for you to try on. Go on dear. Try them on. Then let's discuss our afternoon teatime and shopping plans! I also do CUSTOM feminization videos, just message me :)

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

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

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Chastity Affirmations: Caged Cuckold video from PaintedRose

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

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

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

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Mommy's Little Helper - Sweet Kisses/BJ video from PaintedRose

Mommy's Little Helper - Sweet Kisses/BJ Step-Mom roleplay. Cougar Fantasy. Sweet Talking MILF. Mommy's cougar cub almost forgot his goodnight kiss. So he gets many many kisses close up and then Mommy bumps into your hard erection and notices it is hard. She can't help but want to touch and suck it. She kisses the aching penis to make it feel better and says that when he feels pressure to let her kiss it to make it better until it doesn't hurt anymore. We will do this more! Kiss. Mommy Loves You! POV Dildo BJ.

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Mommy Masturbates Too video from PaintedRose

Mommy Masturbates Too You go into Step-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, Step-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. Taboo Stepmom Roleplay Fantasy. POV.

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Why Mommy Wears Pantyhose video from PaintedRose

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

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Dommy: Bound and Beating video from PaintedRose

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

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Feminization Of Sissy Neighbor - Part 3 video from PaintedRose

Feminization Of Sissy Neighbor - Part 3 Rosie Checks in on Tyler, her neighbor in Sissy Training! She checks in on progress and adds new tasks to complete as great progress is being made in feminization training. The new tasks will be challenging but, rewarding! This Week Tyler must start growing and practicing fixing his hair feminine, Doing glute workouts to get a round tight ass, and begin practicing sucking on a dildo, and using his girl name STACY.

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

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

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Mommy's Girl Gets Changed, Story, BFeed video from PaintedRose

Mommy's Girl Gets Changed, Story, BFeed Now that you're my little girl, let's change, feed, and read to you! Mommy Reads part of Chapter 6 of Alice and Wonderland. It's about Humpty Dumpty and the song is even playing in the background! Humpty asks Alice her name. A name is very important. Mommy is going to give you your girl name and then breastfeed you until you sleepytime. Mommy Loves You.

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Taboo Mom Teaches You: First Time POV video from PaintedRose

Taboo Mom Teaches You: First Time POV (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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Curvy MILF Rosie Squirts multiple times video from PaintedRose

Curvy MILF Rosie Squirts multiple times Monday morning and remembering a hot moan session with you, I wanted more. I start playing with my big boobs and sucking your yummy dick. Then go to town with several toys and wet squirting orgasms...4 toward the end! Very Close Up!

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

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

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Mommy's Love: Teaching You Sex video from PaintedRose

Mommy's Love: Teaching You Sex Step-Mommy notices you were quiet at breakfast and takes you in private to talk. You just had a rough day and needed some extra Mommy love to make you feel better! You have your first big boy boner after some smoochies and Mommy teaches you how to "Jerk off" like a good boy. You're doing so good that you cum on Mommy's big milkers. She starts acting weird! Mommy rubs the white stuff all over her big boobies and her private place and then she asks you to lay down on the floor because you are going to "get hard again" for Mommy's Pussy Fuck. She puts your pee -pee in her mouth and sucks it - she says she's cock hungry for you and wants to make you a big boy today. Your sweet Mommy sits on your "little dick" and bounces from the front and back before cumming on your dick and begging you for a dripping creampie. Very Taboo Dirty Talk in this Roleplay-Fantasy. This is a Rosie Original. This film is 2257 compliant and a solo performed roleplay fantasy. Thank you!

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Sissy Bachelor Party: Brother's Sister video from PaintedRose

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

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

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

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

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

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Valentines Day 2023 Live Date Subscriber CumShow video from PaintedRose

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

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Lonely Single Mom: Taboo Temptation video from PaintedRose

Lonely Single Mom: Taboo Temptation Step-Mom and you are hanging out and discussing evening plans and of course she is bored and you help her set up a dating profile online because you think she is lonely since her divorce from Dad - She's still wearing the wedding ring and staying home a lot. A couple of hours later, Mom already has a date and she's wearing lingerie and a sexy dress - you've never seen her like this! She asks you for your opinion on the dress and tells you that she is nervous because she hasn't been on a date in years and asks you to help her practice. She pretends that you are your date and even begins flirting as she warms up! You tell Mom not to fuck her date and then you tell her you don't want her to go on the date. Mom tells you that she was kind of hoping she'd get laid tonight - and so you offer... Mom says it's inappropriate and asks if you're 'Man Enough' for the job! Next thing you know she's slobbering and sucking your dick, riding your stiff cock - woah - this is your Mom! This is her PUSSY and ASS in your face! It's so wet and tight and she rides you until she tells you to cum for her. You never knew Mom was nasty - why did Dad divorce her? Mom will probably delete the dating app right? This is a POV Stepmom roleplay taboo fantasy with interactive POV style virtual sex, seduction, behind the scenes bloopers, and an all around awesome taboo fuck! Thank you!

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Cuckolding Best Friend w/ Big Cock video from PaintedRose

Cuckolding Best Friend w/ Big Cock Koreen and Dave are the best of friends. They share everything - except sex. Koreen teases Dave with all of her HOT and DIRTY sex stories for the week about all the dicks she sucked. He would never ever think of stroking to her. Never, right? I use a HUGE DILDO while Cucking you in this video!

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Ballbusting Inquisition: Feet and Defeat video from PaintedRose

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

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Curvy MILF Home Alone Orgasming w/ Toy and big tits! video from PaintedRose

Curvy MILF Home Alone Orgasming w/ Toy and big tits! I was all alone and being the weekend, no privacy. I snuck upstairs to bust one out, like a dude for real! sometimes a girl needs it!

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Mom's Sensual Massage: It Hurts Momma video from PaintedRose

Mom's Sensual Massage: It Hurts Momma You're a student staying with Momma Rosie and her husband. Rosie is your fill in Mom and notices you're not feeling well. You tell her about your Back pain and she tells you she was a masseuse before marrying her husband and as a Mom it's her duty to make you feel better - in all ways while in her care. She tells you that in order to save your clothing from the massage oil that you will have to be nude and she provides a towel while reassuring you that it is ok. During your massage, Momma Rosie gets very hot and begins removing clothing. You can feel her tits and pussy pressed into your body as she rubs you sensually. It's time to turn over - and you have a very stiff erection that Momma needs to work around. She decides that she should give you a full massage - down there too and begins to rub oil on your stiff erection. You can tell she likes it but her husband is downstairs! She decides to make you ejaculate during the massage with her mouth and begins giving you a blowjob! After a bit, one thing leads to another and your getting your cock ridden by your Step-Mom with her ass in your face until you cum hard inside of her. Rosie gives you the towel to clean up and tells you to get dressed before her husband comes up! Thank you for this custom video! This is a POV roleplay fantasy femdom MommyDomme video.

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

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

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The Wife Swap Scheme video from PaintedRose

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

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

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

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Honeymoon Homewrecker 4K video from PaintedRose

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

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Engorged: Milking For Rosie video from PaintedRose

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

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Sissy Cuck Fuck Boyfriend Training video from PaintedRose

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

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Therapist-Fantasy: Mesmerized to Cheat On Your Wife video from PaintedRose

Therapist-Fantasy: Mesmerized to Cheat On Your Wife You've been seeing Rosie for a couple of months, a Sex Specialist knowledgeable in working with people who are having problems in the bedroom. The sex with your wife has only decreased and you don't know why, but you love having these Mesmerize sessions with Rosie. She's been mind controlling you to not be attracted to your wife and to cheat on her with Rosie! Rosie is erasing good memories with your wife and rewarding you with her pink shaved pussy. Rosie allows you to orally please her and then gives you a manipulating handjob. When Rosie snaps her fingers, you will remember none of this and only know that you want to please her.

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Curvy MILF Squirting MULTIPLE times!! video from PaintedRose

Curvy MILF Squirting MULTIPLE times!! A personal video of me pleasuring myself until I cum multiple Gspot and clitoral orgasms with several episodes of squirting orgasms!

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Therapist-Fantasy: Mesmerized to Divorce Your Wife video from PaintedRose

Therapist-Fantasy: Mesmerized to Divorce Your Wife You've been seeing Rosie for a couple of months, a Sex Specialist knowledgeable in working with people who are having problems in the bedroom. Your sex life has gone from low to nothing with your wife but you continue to see Rosie three times a week. You feel so relaxed and happy when you leave and you love paying for the longer sessions and paying up front. The session begins and Rosie begins controlling your mind and replacing memories of your wife with her. Rosie has you get on your knees and lick her. You are under her complete control and you only want to please her. Rosie tells you to hire an attorney ASAP to divorce your wife...so you can be inside of her pussy. Not a moment sooner. Rosie manipulates and instead of a handjob, today you get a blowjob (dildo not shown). Rosie tells you that you won't remember any of this but that you will leave her office ready to divorce your wife to be with her. 3, 2, 1. Snap. Good Morning.

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

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

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Rosie's Assistant: Prop Girl Promotion video from PaintedRose

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

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

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

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Nurse Pants: Embarrassed MILF Pants Down video from PaintedRose

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

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Cuckold Chastity Release & JOI Countdown video from PaintedRose

Cuckold Chastity Release & JOI Countdown You've been locked up and horny and now I can give you permission to unlock and release your pent up frustration with a special release and JOI Cum Countdown!

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Dad's New Wife: Blackmail Blowjob video from PaintedRose

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

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Sleepytime Mommy Shares Vibe w/ Son video from PaintedRose

Sleepytime Mommy Shares Vibe w/ Son Step-Mommy awakes in the night and son is not awake next to her, so she decides to masturbate with a vibrator. Mom is startled by son who she accidentally wakes up. Son loves when Mom shares the vibrator. Down with his undies and they share the vibe on their private parts. Mommy let's him orgasms several times before she does. It's always a happy ending in Rosie town. Mommy is very nurturing and loving.

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

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

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Summer Camp: Care Package From Mom video from PaintedRose

Summer Camp: Care Package From Mom You're away at camp for the summer and loving Step-Mom misses you so much and decides to make you a very special care package. She gets the usual stuff that you need but, adds in something special - a video letter and her panties. Thank you for this CUSTOM VIDEO. This is a POV masturbation panty fetish Ste-Mom taboo roleplay fantasy video.

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Cuckolding Marriage Therapist JOI CD SPH video from PaintedRose

Cuckolding Marriage Therapist JOI CD SPH You accidentally sent your little dick pics to your therapist. She calls you to her home office right away to address this little situation. This must be the reason you are having problems with your wife, How did you even get her to marry you? You will have to make her happy by any means necessary to keep her. You will have to start bringing in bigger dicks, you will have to serve. I want to see if you also have a small cumload and so I count you down in a humiliating way. JOI, CD, SPH, Cum Countdown, Chastity, Cuckolding.

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