Sophia Sylvan

Our stepparents say we never play together anymore now that we're more grown up, so they made us hang out in my room. I'm annoyed and rolling my eyes, hanging out casually in a crop top, panties, and ankle socks. I ask what kind of game you want to play? I'm bored, so I decide to make things more interesting. I tell you that I saw you shoplifting the other day and I'm gonna tell our stepparents unless you do everything I say. I know men are gross pervs, are you grown up enough to be one too? I humiliate you by making you sniff and kiss my socks, and you reluctantly do as I tell you. Soon though, you get a stiffy. I was right, you are a perv! Nasty foot perv getting hard over smelling your step-sister's feet. See how many toes you can get in your mouth, step-brother. Now jerk off for me, you have to do everything I want. I peel off my sock and tell you to smell it before I let you worship my perfect toes. They're so soft and pretty, you can't resist jerking to your own step-sister, especially when she's so curvy, pretty, and undressed. You feel so shameful but so aroused as I instruct you just how to kiss and worship my perfect feet. I even let you put my warm, dirty sock on your cock to jerk off in, just like you do all alone in your room. But my soft step-sister sock feels so good doesn't it, little stepbrother?

This is a "your step-mama" style video where I talk trash about your step-mom and guide you through a jerk off instruction to her. There are versions coming up where you fantasize about using her other holes, at my direction. Looking to jizz in her mouth? Your Step-Mama: Blowjob Version

There is also this version Your Step-Mama: Creampie Version

You're late to our playdate and Mistress is not pleased. You were out helping your stepmom again, you're such a stepmama's boy it is ridiculous. I was going to grant you release today too. You start begging and pleading, you just can't help but do the bidding of a superior woman, stepmother, or Mistress. I'm starting to get annoyed and jealous. I tell you that I'm going to give you release but only on certain conditions. Strip naked and start jerking as you kneel, and I'm going to tell you a fairytale about a very dirty boy and his stepmother. Think of her face, and her body in great detail. Imagine her lips opening to suck your cock into her mouth. Imagine her tits and her ass, and her pussy. Now jerk off while you picture yourself eating her out til she cums hard in your mouth. I tell you that you're going to help me teach your stepmom a lesson about taking advantage of your time with her and being so selfish. I guide you through eating her ass, reminding you that my ass is better and you could be worshipping it right now if you weren't late. After you get her asshole nice and wet with your tongue I tell you you're going to have to fuck her ass. Is it loose or tight? How does it feel to fuck your stepmom's ass? Show her who's boss, be a man for a change. Fuck her ass, pump and dump in it, give her a present to remember you by, and then leave her full of your cum. Next time you better remember to treat your stepmother like this when you're supposed to come see me after, give her what she needs of you then hit the road!

This is a "your step-mama" style video where I talk trash about your step-step-mom and guide you through a jerk off instruction to her. There are versions coming up where you fantasize about using her other holes, at my direction. Looking to jizz in her mouth? Your Step-mama: Blowjob Version

You're late to our playdate and Mistress is not pleased. You were out helping your step-mom again, you're such a step-mama's boy it is ridiculous. I was going to grant you release today too. You start begging and pleading, you just can't help but do the bidding of a superior woman, step-mother, or Mistress. I'm starting to get annoyed and jealous. I tell you that I'm going to give you release but only on certain conditions. Strip naked and start jerking as you kneel, and I'm going to tell you a fairytale about a very dirty boy and his step-mother. Think of her face, and her body in great detail. Imagine her lips opening to suck your cock into her mouth. Imagine her tits and her ass, and her pussy. Now jerk off while you picture yourself eating her out til she cuts hard in your mouth. Visualize sliding your hard cock into your step-mother's pussy, fucking her missionary style while you have to look right at her, til you spill your seed in your own stepmother's cunt, possibly impregnating her! I trash talk her while you jerk off, talking about her used up loose pussy that you came out of, and etc.

This is a "your step-mama" style video where I talk trash about your step-mom and guide you through a jerk off instruction to her. There are versions coming up where you fantasize about using her other holes, at my direction.

You're late to our playdate and Mistress is not pleased. You were out helping your step-mom again, you're such a step-mama's boy it is ridiculous. I was going to grant you release today too. You start begging and pleading, you just can't help but do the bidding of a superior woman, step-mother, or Mistress. I'm starting to get annoyed and jealous. I tell you that I'm going to give you release but only on certain conditions. Strip naked and start jerking as you kneel, and I'm going to tell you a fairytale about a very dirty boy and his stepmother. Think of her face, and her body in great detail. Imagine her lips opening to suck your cock into her mouth. Imagine her tits and her ass, and her pussy. Now visualize sliding your hard cock into your stepmother's mouth, look at my body as you are denied access to me, and think of her instead. Fuck her face, and use her mouth as a cumdump, step-mama's boy!

Prefer another ending? Try Principal Step-Mom Punishes: Facesitting or Principal Step-Mom Punishes: BJ

You've been a very bad boy and got kicked out of yet another school. I tell you to meet me, I'm the principal at an all girl's school, in my office. When you finally arrive, I am very serious and stern. You have disappointed me so much, step-son, I have to keep a closer eye on you, so I'm transferring you to this school. In order to fit in, you'll have to dress to code, and that includes wearing a kilt, knee socks, a white blouse and regulation cotton panties. You'll have to wear a wig and do your hair in pigtails too. Now strip down and put them on, and henceforth you will be my step-daughter. Now sit over Principal Sylvan's lap, young lady, you're going to get a spanking! You've been a very naughty girl! You feel something hard? That's because step-mommy has another punishment for you, you're going to take this big dick with no warm up. That's what happens to naughty girls!

Looking to cum on my leather jacket? Leather Jacket Play with Step-Mommy

It's been a while since step-mommy wore fetish clothing to get you off, now it's time to change that. Step-son, get into bed with step-mommy and come gaze upon the sexiness of step-daddy's leather jacket. We both miss him when he's away so I'm wearing it for us to play with. Just don't tell him! Do you like my slutty nipple-cut out studded bra I picked to wear with it? I think it looks so sexy with jeans, heels, and his motorcycle jacket. Step-mommy will teach you all about how to appreciate it and make you into a real fetishists. Jerk off for me while I tease you and teach you all about the sensory delights of leather. The sound, the feel, the smell, it is all After you do a good job with your fetish lesson, and worshipping step-daddy's jacket, I tell you to suck my nipples through my peekaboo studded bra. Nurse on step-mom's tits before bed, that's a good boy. Now cum while you feast on step-mommy's naughty big nipples, and don't tell step-dad!

It's been a while since step-mommy wore fetish clothing to get you off, now it's time to change that. Step-son, get into bed with step-mommy and come gaze upon the sexiness of step-daddy's leather jacket. We both miss him when he's away so I'm wearing it for us to play with. Just don't tell him! Do you like my slutty nipple-cut out studded bra I picked to wear with it? I think it looks so sexy with jeans, heels, and his motorcycle jacket. Step-mommy will teach you all about how to appreciate it and make you into a real fetishists. Jerk off for me while I tease you and teach you all about the sensory delights of leather. The sound, the feel, the smell, it is all Step-mommy wants your cum to condition step-daddy's leather!

Looking for the strap-on blowjob version? Principal Step-Mom Punishes

You've been a very bad boy and got kicked out of yet another school. I tell you to meet me, I'm the principal at an all girl's school, in my office. When you finally arrive, I am very serious and stern. You have disappointed me so much, step-son, I have to keep a closer eye on you, so I'm transferring you to this school. In order to fit in, you'll have to dress to code, and that includes wearing a kilt, knee socks, a white blouse and regulation cotton panties. You'll have to wear a wig and do your hair in pigtails too. Now strip down and put them on, and henceforth you will be my step-daughter. Think this is your punishment? No. First you're going to apologize for being such a bad step-son, I mean, step-daughter, and kiss my ass, literally and figuratively. That's right, it's Principal Sylvan to you now. You're going to obey everything I say from now on, is that understood. What a slut you look like, you know what happens to slutty Bad things. I'm going to punish you by sitting on your face very strictly, you'll have to smell me, and be crushed by my weight, right here on my office chair. I think you will make a nice comfortable, warm seat. Just bend backwards a bit, just like that. You won't be able to move at all, you're going to be very vulnerable, strictly under step-mommy's control. I am not going to be letting you out of my sight anytime soon. Now let me get more comfortable and put my full weight on you...

You've been a very bad boy and got kicked out of yet another school. I tell you to meet me, I'm the principal at an all girl's school, in my office. When you finally arrive, I am very serious and stern. You have disappointed me so much, step-son, I have to keep a closer eye on you, so I'm transferring you to this school. In order to fit in, you'll have to dress to code, and that includes wearing a kilt, knee socks, a white blouse and regulation cotton panties. You'll have to wear a wig and do your hair in pigtails too. Now strip down and put them on, and henceforth you will be my step-daughter. Think this is your punishment? No, look under step-mom's skirt for your punishment. You're going to take step-mom's big dick while on your knees right here in my office, first lick my big cock over my pantyhose and tease it like the bad slut you are. Now open wide for step-daddy's cock, step-daughter, choke it all down, show me how good you can be!

This is part 2 of Cucked by Step-Mom and Step-Dad , or if you prefer, check out Cucked by Step-Mom and Step-Dad: Reversal Version , where you are cucked but then turn it around and make your step-dad a cuck when you fuck your step-mom.

I'm really good at dirty storytelling, and I know you taboo-loving perverts will enjoy how much I get into it as I paint a filthy picture of what happens when your frisky step-parents call you into the bedroom to play. First they cuck you and make you watch them have sex, in their bedroom this time. No more peeping on the Then your step-daddy makes you suck your step-mom's big tits while he fucks her and you jerk off. Next he's jerking you off...and you're face-fucking her...she's lactating, he fucks you, and makes you his gay bitch step-son. Tune in for all the juicy details! I strip out of my leopard print bra, and spread my legs, caressing my body as I get aroused from guiding you through this dirty taboo tale.

Prefer another ending? Check out Dress as Step-Mom for Therapy: Praise Ending and Dress as Step-Mom for Therapy: Humiliation Ending

I'm an unconventional sexologist who likes to try out new methods to help my client work on their shame issues and disturbing sexual fantasies. You're a client who has fantasies about his stepmother dressing him up, among other things. We agreed on a session focusing on lingerie and stockings, where as your sexologist I dress up in ways that resemble your sexy stepmother. I have a tight low cut dress on, with garter belt, stockings and heels. Once we begin I call you stepson and you call me stepmom or stepmommy, as I start teasing and seducing you, dominating you sensually. I show you my garter belt and tell you how I always wanted a stepdaughter and you're going to be one for me. I have you strip down then put you in some of my sexiest lingerie. I tell you how I know you have a thing for my stockings, as I sometimes find them sticky in my drawer. You've been very naughty and now you're going to be shown for what you are, a cross-dressing slut for stepmommy. I have you put on my pretty black sheer thong and rub your girlcock in it, making it nice and hard for your stepmother. Then you put on the stockings so we can match, step-mother and step-daughter. I tell you that now is the time to get more strict and I tell you that to complete your outfit we need some jewelry, a ring in fact. I bring out a large silver ring and tell you it's meant to go around your girlcock and balls. Then a cage comes out and I tell you of your fate, to be a caged step-son, no more use for that cock, only your holes that can be penetrated are useful to girls. Now get that boner stuffed in here and step-mommy will lock you up nicely, so you'll be a nice obedient step-daughter!

Check out the other versions: Homeschooled JOI (JOI Ending) & to come Homeschooled JOI: Ruined O Ending

I've been homeschooling you for a while now, since I like to be in control of your education. I dress up as your teacher for our lessons, to help us both take it more seriously. Today I have on a low-cut dress that hugs my figure and nylons. You are distracted and not following along the lesson well and I'm frustrated. I want my step-son to do well in school I decide a bit of a diversion from our normal lessons will help. I lean forward and ask you what's wrong, and your eyes can't stay away from your own step-mom's cleavage. I know hormones are to blame and I decide that a little sex education won't go amiss. I tell you that you're going to get a lesson in jerking off from your step-mother today. I tease you with my body without taking off my dress, with my cleavage, with my stocking tops and garters, with the information that I'm not wearing any panties. I have you stroke slow, then faster, and edge yourself. I name the different parts of the penis and have you stimulate them, showing you the pleasures of the body. I put my feet up on the coffee table and I'm in black stockings with no shoes. My soles and toes look so pretty and I tell my you, my step-son to kiss and worship my feet to show me that you're grateful for your lesson, and I allow you to come while I tease you with my cleavage you kiss my perfect MILF soles.

Don't miss the JOI release version and the JOI feet version!

I've been homeschooling you for a while now, since I like to be in control of your education. I dress up as your teacher for our lessons, to help us both take it more seriously. Today I have on a low-cut dress that hugs my figure and nylons. You are distracted and not following along the lesson well and I'm frustrated. I want my step-son to do well in school I decide a bit of a diversion from our normal lessons will help. I lean forward and ask you what's wrong, and your eyes can't stay away from your own step-mom's cleavage. I know hormones are to blame and I decide that a little sex education won't go amiss. I tell you that you're going to get a lesson in jerking off from your step-mother today. I tease you with my body without taking off my dress, with my cleavage, with my stocking tops and garters, with the information that I'm not wearing any panties. I have you stroke slow, then faster, and edge yourself. I name the different parts of the penis and have you stimulate them, showing you the pleasures of the body. I tease you with my stocking tops and give you detailed JOI instructions demonstrating on a dildo. Finally, I allow you to cum for your step-mother, while I jerk off the dildo showing you how I want you to stroke, but pay attention, step-mommy has one final instruction, you have to cover your cockhead when you stroke and ruin your orgasm! That's what you get for not paying attention in class. Maybe you'll learn next time.

I've been homeschooling you for a while now, since I like to be in control of your education. I dress up as your teacher for our lessons, to help us both take it more seriously. Today I have on a low-cut dress that hugs my figure and nylons. You are distracted and not following along the lesson well and I'm frustrated. I want my step-son to do well in school I decide a bit of a diversion from our normal lessons will help. I lean forward and ask you what's wrong, and your eyes can't stay away from your own step-mom's cleavage. I know hormones are to blame and I decide that a little sex education won't go amiss. I tell you that you're going to get a lesson in jerking off from your step-mother today. I tease you with my body without taking off my dress, with my cleavage, with my stocking tops and garters, with the information that I'm not wearing any panties. I have you stroke slow, then faster, and edge yourself. I name the different parts of the penis and have you stimulate them, showing you the pleasures of the body. Finally, I allow you to cum for your step-mother, while I pose showing off my whole body down to my stocking feet on the love seat to get a load off your mind so you can finally focus on your studies.

I'm an unconventional sexologist who likes to try out new methods to help my client work on their shame issues and disturbing sexual fantasies. You're a client who has fantasies about his stepmother dressing him up, among other things. We agreed on a session focusing on lingerie and stockings, where as your sexologist I dress up in ways that resemble your sexy stepmother. I have a tight low cut dress on, with garter belt, stockings and heels. Once we begin I call you stepson and you call me stepmom or stepmommy, as I start teasing and seducing you, dominating you sensually. I show you my garter belt and tell you how I always wanted a stepdaughter and you're going to be one for me. I have you strip down then put you in some of my sexiest lingerie. I tell you how I know you have a thing for my stockings, as I sometimes find them sticky in my drawer. You've been very naughty and now you're going to be shown for what you are, a cross-dressing slut for stepmommy. I have you put on my pretty black sheer thong and rub your girlcock in it, making it nice and hard for your stepmother. Then you put on the stockings so we can match, step-mother and step-daughter. I tell you that now is the time to get more strict and I start humiliating you for not looking more pretty in stepmother's clothes, for stretching out my panties with your girlcock, and for making my lingerie smelly. You look like a real queer and maybe you should get fucked in your ass or go out on the street and make stepmom some money. Endure stepmother's brutal humiliation as you rub your girldick and try to cum to the countdown to her ass.

I'm an unconventional sexologist who likes to try out new methods to help my client work on their shame issues and disturbing sexual fantasies. You're a client who has fantasies about his stepmother dressing him up, among other things. We agreed on a session focusing on lingerie and stockings, where as your sexologist I dress up in ways that resemble your sexy stepmother. I have a tight low cut dress on, with garter belt, stockings and heels. Once we begin I call you stepson and you call me stepmom or stepmommy, as I start teasing and seducing you, dominating you sensually. I show you my garter belt and tell you how I always wanted a stepdaughter and you're going to be one for me. I have you strip down then put you in some of my sexiest lingerie. I tell you how I know you have a thing for my stockings, as I sometimes find them sticky in my drawer. You've been very naughty and now you're going to be shown for what you are, a cross-dressing slut for stepmommy. I have you put on my pretty black sheer thong and rub your girlcock in it, making it nice and hard for your stepmother. Then you put on the stockings so we can match, step-mother and step-daughter. You look so pretty and sexy dressed as a girl. Stepmommy likes it, now kiss stepmommy's ass and say thank you as you rub yourself to orgasm in stepmommy's fancy lingerie.

Your stepmom is unhappy with you for being so careless and hormonal, leaving cum soaked tissues all over the room. So she instructed you to save a load of cum and to join her in her room for your punishment. Your step-mom is very strict and always thinking of creative and humiliating punishments, and you're nervous. You can't help but stare as her breasts are almost falling out of the black dress she is wearing. She tells you she knows a new mesmerizing technique to help train you to obey, and she begins. She tells you to look into her eyes, to submit and jerk off for her. You can't help but follow her instructions and jerk off like the horny young man you are, humiliatingly in front of your own step-mother. She tells you that you're going to surrender and do whatever she asks, and show her how good boys clean up their messes. She makes you edge a few times, and tells you that on the countdown you'll swallow the saved load. She takes her tits out and you fall deeper into obedience as she makes you beg to cum...

Your stepmom's best friend is watching you, she always dresses so slutty and tonight is no exception, as she lounges in your stepmother's bed with her tits hanging out of her black dress. She's wearing stockings too, and teasing you as she knows you were snooping and saw your stepmother's text to her. You saw something shocking and now she is explaining to you that since she got divorced, she is planning a gangbang for herself and your stepmother. She talks about the kinds of guys your step-mom and she are going to fuck and how she will fuck them. She can see you getting aroused and she touches herself and lets her boob spill out. You're going to have to keep this a secret, but maybe she can arrange some way for you to attend the gangbang...jerk off for your stepmom's best friend and she tells you what a filthy horny whore your stepmother is and will be!

Your step-mom is upset with you and she called you into her room to have a talk. She has to sit up on the bed with her. She's upset that you take her for granted and don't appreciate all she has done for you. After she grew you in her belly, and suffered as it grew large, and pushed you out of her vagina, stretching it out and damaging her body, you have the nerve to be a disrespectful step-son! She tells you that she's going to punish you for your own good, and makes you take off your clothes. She threatens you and you're terrified, and do as you're told. She is wearing a sexy outfit while she lubricates your butthole and you're so confused and you have strange feelings in your body. She inserts the hose of the aquarium pump and says it is perfectly safe, she's going to put air in your belly so you know what she suffered being pregnant with you. It slowly inflates and your step-mom is so good looking that with the pressure in your belly, you start to get a hard on. At the same time, your belly starts to cramp and you cry out in pain. Step-Mom tells you to stroke your dick, it will make it less painful, she's such a caring step-mommy. You do as she told and it distracts you from the air filling up your tummy. You get bigger and bigger and it's such a strange feeling, but arousing. She slaps your belly and even kicks it to simulate the kicks you gave her during pregnancy. You beg her to let you go and take out the air but she's determined that you'll look several months pregnant before she stops. You're so afraid you'll explode! But maybe you deserve it for being such a bad step-son. Finally she allows you to cum all over your big round balloon belly and takes the hose out after you promise to be good.

Originally a custom video commission. Looking for your own? Scroll up to my customs button for more info. This custom had the personalization edited out. To play along, have a chastity device, a photo of your step-mom, a toy and a pair of your step-mother's dirty panties ready.

I greet you in bed in black lingerie with fishnet ankle socks and stilettos. You're instantly turned on and feeling submissive with me dressed like this, especially wearing metal heeled pumps. I tell you that for amusement, I decided to manipulate you and get what I want by telling your step-mother about your perversions for her. She'll know all about how you lust after her and all of your nasty little secrets that you told me. I have evidence and I know all of her information. I'm going to use this to get you to do whatever I want. I taunt you about how your step-mother and I will dominate you together and punish you, once she knows what you're really like. We're going to make you worship our high heels, and lock you up in chastity. Then we are going to really use you and fuck your holes like the bitch you are.

**This clip is strict, but playful, not formal, and humiliating in tone at times but not extremely so.**