Sophia Sylvan

In this video from 2012, I am your big step-sister who you share a bedroom with. I find out that you've been watching me while I masturbate! I get annoyed and tell you to stop, then proceed to play with myself in my sheer white bikini panties. After I cum hard I find out you didn't stop watching me you little brat! I lean back and try to cover up my breasts and scold you for being such a little pervert. I tell you that I decided things are going to change around here, no more jerking off in my panties anymore, you're going to wear them if you like them so much! I'm going to make you into my sissy step-sister!

I greet you looking like a voluptuous goddess in my sheer bodysuit, red lips, long blonde hair, and heels. You're you're hard for me, and you're weak. I want some entertainment, and I am in the mood to humiliate you through your turn ons. I know you love older women, so I make you get a photo of your step-mom that you like and I describe in shocking and delicious detail you watching your step-mom be a slut, and then you participating too. I tell you how much your step-mom craves young cock, and how she set up a gang bang so she could get her old holes used by hard young dick. You show up by surprise to the party and fuck her and cum in her too. Now I want you to blow all over her photo! I tease you with my body throughout the video as well as my words, to keep you on the edge and filthy and weak for me in your humiliating task.

I'm your step-mother and you asked for something to eat...I'm so neglectful I only have been getting takeout and making instant noodles for you, and I'm always more concerned with my phone, my outfits, my makeup, my boyfriends. You're sad and lonely and starting to be horny all the time too. I'm in a leopard bra and panty set as I putter about the kitchen boiling a kettle and preparing your noodles. You dare to complain, and I quickly put you in your place. There will be no ingratitude and no attitude in my house, young man! You'll learn some respect. I notice your boner and humiliate you by making you get down on your knees and kiss my ass. You'll go without your dinner tonight to teach you a lesson. I can't put up with this sassiness so I have to take it a step further. You will literally kiss my ass. That's right step-son, so exactly as I say while I remind you who your step-mother is. You'll obey and respect, and you'll tongue my asshole if I tell you. That's right, lick it little pervert, and cum for your step-mother! If you don't cum on command, after you finish eating ass for your dinner you'll eat your load too, so get stroking and cum! 10, 9, 8....

Originally a custom video commission. No names were used. Want your own or to find out more? Scroll up to find my CUSTOMS button! This is a sequel to The Catburgler vs. the Superhero

I am a homeowner who enters my bedroom to find a strange man in spandex (you) resting in my bed. My house has been ransacked and items have been stolen. I try to wake you up in vain. I look at your ensemble and realize you're that new superhero in town people have been gossiping about. Well, looks like you failed! I wake you up and demand to know what happened, but you're groggy and ashamed. I look at the security cam footage on my phone (you can hear the last episode in this series playing). It shows a curvy latex-clad villain robbing my house and you come to save the day but are distracted by her huge ass in latex, and end up getting a hand job! I am outraged and decide to punish you. I put you over my knee and spank you as you watch me and my cleavage in mirror. Audible slaps are heard as I scold you for being so weak. You get hard for me and I know that you're secretly a submissive. Then I strip off my blouse and decide that since you have a Step-Mommy thing, I'm going to give you a hand job while I make you call me Step-Mommy. I'm turned on by your surrender and tell you that you need to learn to be a better superhero for me, and to go find my stolen items. After you cum, I make you eat me out as an apology.

It's Valentine's Day and I'm not happy at all. You made Valentine's for your teacher and all of your classmates as everyone else in your class did, but you didn't do anything for me! You just showed up nude as if your hard dick is a gift. I'm really offended, I thought I raised you better than this. I wore this special outfit and bought these faux garter red tights to surprise you, but you ruined it all. You really think that the thing I can have any minute of the day is a gift? The thing that gives YOU pleasure? Hardly! It's just any other day. I need to be more firm with you again. You're going to get on your knees and beg forgiveness while you kiss step-mommy's ass. That's right and while you're down there kiss my boots too. I've been wearing this under my work outfit all day and it's uncomfortable now. I remove the sweaty synthetic boots while I make you grovel on the floor, jerking. Breathe in my foot stink, step-son. My nylons got dirty in the boots and need some cleaning, but first breathe deeply. My foot stink is your Valentine, enjoy! I guess you can cum...if you can.

Your sexy, curvy step-mom comes in your room without knocking, as usual, but she's looking like a knock out in a skimpy bra, tight shorts, black pantyhose and the highest heels you've ever seen her wear. You instantly get a boner but your hopes are dashed when she announces she has a Tinder date coming over soon. Your step-mom and you have a...unique relationship and she's taken to disciplining you erotically, with humiliation and other punishments. Trouble is, you've started to enjoy these times and she's started to enjoy the boner they give you. She even went so far as to let you fuck her once, but that didn't go over well, you were so excited you came in two minutes. So she's rubbing it in that she has some stud coming over, asking how she looks, and telling you all about how she can't wait to get fucked by someone experienced. It's tough being a single step-mom, and there sure aren't many boundaries between you. She puts you in your place, making you get on your knees and kiss her heels and even makes you humiliatingly suck them like long, slender cocks. You can't help but get turned on by your sexy step-mother, even through your embarrassment, and your shame that what you two do surely isn't normal. Is that why it makes you more hard than anything else? She makes you lay on the floor and jerk your cock while seeing if her feet smell. She's been wearing these pantyhose all day at work, and no time to change them now. They do stink? Why are you hard then? She has to air them out for her lover, who is texting her audibly as you're trying to cum, making you inflamed with jealousy. You surely will hear them have sex. Your step-mother smothers you with her feet over your mouth and nose as you climax, then slips her elegant size 7 feet back into her impossibly tall heels and says goodnight as she closes the door behind her.

I tease and seduce you in my sexy lingerie with stockings and heels, getting you hard and telling you I know your secrets. You love older women. You love thick, juicy MILFs like me. Not only that, you've always had a thing for your sexy step-mother. You crave her big tits and fat ass, and her hairy MILF pussy, or whatever she looks like. Jerk off to me while I make you jerk off to her picture. Follow my perverted instructions and play along as I tease you for your kink and make you push it further than ever before in a fantasy where I make you dream of fucking your step-mother and doing the most depraved taboo acts with her. While you stare at her face and cum all over her.

You picked out a Halloween costume for your step-mother, doing a bit of a trick or treat thing, and a nasty trick in that you got your thick and curvy step-mother a very tight skimpy outfit! You're going to a family costume party for her work and you picked out the costumes. You're the only step-son and she's a single step-mom and you're a bit closer than most moms and sons, you get naked in front of each other despite your age, etc. You've always had the hots for her but she lacks confidence and doesn't dress very sexy, always covering up her big butt and fat titties. So you're ecstatic, trying to cover your boner in your Robin costume as she strips off her satin robe and starts putting on her pushup bra, garter and black leotard. She catches you staring at her cleavage as she bends over to clip on the knee socks. She puts on the wig and the witch hat and looks amazing, your boner is aching but you feel so confused and guilty. She notices your boner and is nice about it, then gets on the bed to lace on her high heeled booties you picked out. Once she's dressed, something changes...your step-mom is different...dirty...assertive. She tells you that you can't go to the partner in such a tight outfit with a boner like this so it must be taken care of. She tells you to take it out and jerk it for her, and makes you clean the rental heels with your mouth, taunting you in such a forbidden way! She's sexual with you, and very dominant, and you can't do anything but exactly what she says, which includes worshipping her ass, sucking her heels, being called humiliating names, and more.

Originally a custom video commission, but the name was edited out. Curious about customs? Scroll up to my CUSTOMS button and drop me a line!

I know how much you crave your curvy step-mommy with her huge ass and fat titties. Go on, jerk off for her, dirty boy. You're such a slutty step-son, so horny, peeping on her in the shower through the keyhole. Do you think she knows you're watching and spends extra time soaping up her big tits and ass, knowing you're jerking off? Wouldn't you love to see her stripping off her clothes, like this, and showing off her hot, mature body? That soft tummy, those big hanging titties, they get you hotter than anything, so jerk off to your step-mom like you're jerking off to me. I talk about how you would worship her body, her tits, her big ass, her step-mommy pussy. Imagine her getting a BBC gangbang, taking all those extra large, long cocks and loving every inch. I describe in filthy detail your step-mother being a huge whore for big black cock and taking all their loads, you'd love to cum to that.

You've been home for the pandemic and not only do I have to work, since I'm an essential worker, I have to find time to teach you as well! I'm so tired, working for a pervert boss who has me in tight shiny pantyhose and heels all day long, working as a receptionist at a doctor's office. But it puts food on the table and you need to be grateful! I kick off my heels and decide to teach you a lesson, how to massage my feet and legs. My legs are strong, thick and powerful and my feet have a strong aroma. I notice you reacting, and I laugh and make you smell them. They got stinky like this by working hard, you little bastard. Smell step-mommy's feet! While you're at it, kneel for me, you need to learn obedience and discipline. Now, you need to always respect your step-mother and you haven't submitted your homework yet and a Zoom meeting is coming up with your school board! Kiss my ass! For real, do it! Now I'm going to lift my skirt and you're going to smell the sweet fragrance of Step-Mommy's sweaty asshole and pussy before you go off to your room to jerk off...I mean...do your homework.

Originally a custom video production, but no names were used. Curious about your own? Scroll up to my CUSTOMS button!

You're a and your step-mommy hosted a special event party at a rented location and I'm looking after you while she's in the bathroom. Your party is all over and it is time to clean up this mess. You have dozens of balloons, and I start popping them with my heels. The noise is so loud and you're scared and I tease you. I pop them with my heels, my nails and scissors. I soon realize you're getting a boner, and I tease you about that too as I pop your party balloons. Are you sad that I'm popping them? They're garbage now! I gather up the latex shards and put them in a garbage bag. I tease you further by popping one under my butt by sitting on one accidentally, then between my pantyhose-clad thighs. Soon I decide to make the game more fun and give you a special birthday present. I remove my bra and stuff it in the couch, and show you my tits while I pop them maliciously and throw the balloons in the garbage. You're watching me, fascinated, as I walk around in my tight outfit, bending over, my huge ass fixating you. You are transfixed, and you can't even take care of your little boner, poor boy, your step-mommy will return any moment. I finish making all of your balloons garbage and tell you to jerk off about me tonight.

We've been quarantine a long time, and it's stopped me from going out and picking up guys like I normally do. So I've grown out my bush, because who is going to see my pussy? But it's been a while, and I'm getting really horny. I decide to start up our taboo relationship again, for the time being at least, and have you jerk off for me. I show you my hairy pussy under my lingerie, and sit on the couch, spreading my legs. I rub my clit while you get naked and approach. Lick my hairy pussy, step-son! Eat my hairy cunt! After a while, I realize I will only cum if I take control, so I have you lay on the floor and stand over you, dominating you. Your thick step-mother is the hottest woman ever to you, and you are in heaven, desperately trying to hold back your load. I am topless, gorgeous and my pretty brown bush is a thing of beauty. I sit down and grind my wet cunt all over your face, using you and finally cumming hard on my own step-son's face. Then I let you look at my tits and eyes as I keep grinding and order you to cum for your step-mother.

Since your step-father passed away, I've been your sole guardian for a whole month, you've comforted me well, and I've comforted you, right? You got to service me with your young cock and mouth, but I'm bored of you now. I have a new boyfriend, and things are going to change dramatically. People are saying I ended your step-father, I know, but that's just rubbish, why would a sexy young widow eliminate her rich elderly husband after only one year of marriage? So ungrateful, haven't I been a wonderful step-mother to you? Come, suck on step-mommy's titties one last time, step-son, stroke your young boner and I'll let you taste me if you're good. I make you lick my heels to amuse me, laughing at your pathetic submission. I know you love me in stockings, but I'm not wearing them to arouse you. You love sitting on your knees between my thick thighs and servicing step-mommy's hairy pussy don't you? Get to work, I'm going to get comfortable and get this stocking off, don't worry, isn't it soft and silky around your neck? I use the stockings as reins as I slowly you. Step-Mommy's legs are strong, you're not going anywhere...I'll have your inheritance, every last penny, you amused me for a time but now it is time for you to end just like your step-father did...

Since your step-dad passed away tragically a couple of months ago, you've been left in sole guardianship to your step mom and when you come out of your room from crying you find her in just stockings, bra and panties. You're shocked but...distracted. She tells you that it's time to stop being sad, and time to feel good. She's been lonely since your aging step-father passed on, and she knows you have a hard young cock to provide. You can't resist your step-mom when she acts like this and you do everything she says...including kneeling to kiss her ass and pledge your devotion. What choice do you have, but to be her slave? When she has your trust fund under her grasp. You're not an adult yet, and she says you'll be staying close for a long time to come. She could use a man in the house, and between her legs, and you'll do just fine. She has you fuck her right in the chair in front of your step-father's urn until she cums on your young cock and you cum inside her, your own step-mom and sole guardian. She says there will be a lot of this sort of homeschooling in your future, and that you can rest in bed with her tonight.

You come in my room to pester me again, my annoying little step-brother. But I'm mad at you, because when I was picking up laundry I found my dirty sports bra and thong from when I last went to the gym hidden under your pillow! I know you were up to something perverted with them, admit it! Have you been feeling horny in your pee pee as you get older, step-bro? Well I'm going to teach you a lesson. Strip down naked. What's this? Little pervert has a boner! Nasty! Are you just so horny and desperate for attention? Well since you like my bra and panties so much you can put them on or I'll tell step-mom and step-dad! Were you sniffing the crotch and sweaty pits? I always wanted a step-sister...so I'll make you one. Much better than gross boys. I subject you to teasing and light humiliation, and sissification as I make you up with lipstick, blush and powder. Once you're done up pretty I get turned on and let you lick my pussy, lifting my skirt to show you my camel toe in matching pink panties and then pulling it aside to make you lick your own step-sister's pussy til she cums.

Your step-mother has you laying on the ground, looking up at her. You can almost see up her dress, but you're enjoying the view of her dark brown stockings and the glimpse of lace tops, she's trained you to love her feet and the look, smell and taste of her nylons. She tells you, as usual, what a disappointment you are as a step-son, and lifts her glorious foot for you to sniff between her sweaty toes. Humiliated and broken, but so aroused, you obey. Nothing you do is ever enough for this woman, and she always has you at her mercy, waiting for a moment of reward or affection, and you always try to please her, now. You know what will happen if you don't. She sits on the sofa and has you crawl over and worship her thick legs in her smooth espresso stockings, and you are in heaven. The scent of her, the way the nylon highlights her skin, the warmth of her body under your lips. Graciously, she allows you to pleasure yourself. She promises to let you lap the new trimmed bush she's grown, if you are a good boy. You crave to pleasure your step-mother that way, she is always so wet and horny. Higher and higher you only dare put your mouth where she bids you, on her powerful calves, her sumptuous thighs, and finally, on the creamy skin above the lace. You feel driven out of your mind with pleasure when she finally allows you to worship between her legs, baring her breasts and moaning into your mouth. She cums, and it is a wonder, yet she makes you beg, reminding you of your place, desperate for her approval and your release.

Your step-mother comes in to tuck you into bed, and you know trouble is coming when you see her in a skintight, unbelievably low-cut jumpsuit, makeup and heels. She tells you that you have school tomorrow, but she's going out to get dick. Young, college dick at one of the clubs young men frequent to get laid. Your step-mom is a horny slut, and she often makes use of your hard, young cock, which hardens at the mere sight of her now. But your cock isn't enough, she needs fresh young cock, and regularly. You used to be jealous, but now you're just turned on by what an insatiable nympho she is, and you can hardly think straight as she shows off her outfit, caressing her luscious body and showing off her ass as she tells you her aims for the night. She wants some freshman cock in her big tight ass, and multiple loads at that. She hopes to be brought home to some guy's dorm room, and fuck his roommates too in a big gang bang. Your step-mother is such a slut. She tells you to jerk off for her, and that when she comes home, she'll sneak into your bed and suck you awake. Your step-mother totally owns your cock, you can hardly think of anyone else, and you're such a cuck to her slutty ways. You won't be able to rest thinking about her seducing young men and taking their dick like a filthy whore, raw and creampied. She has you lick her ass to reinforce your submission and warm up her hole before she pulls her jumpsuit back up, without panties of course, and heads out on the town.

*No gay stuff in this one!*

Well, it is Christmas Eve, and I'm dressed to celebrate with my Mrs. Claus nightie and my bedroom decorated, but what do I have? A step-son who has been naughty all year. You lied to me so many times when I asked for help around the house, saying you had homework, but I found out you were spending most of your time in your bedroom masturbating. Now you're going to suffer the consequences. Present your bottom young man! Step-Mommy is going to beat some respect into you. I'll redden those cheeks into Christmas colours with this wooden spoon. Now turn over, I'm going to put these clothespins on your nipples, tongue, balls and cockhead. This body belongs to me! And I'll beat them off now, just like you beat yourself off, haha! How about some scented wax from my festive candles? Oh does it hurt? Poor baby. Now turn over and hump step-mommy's bed while I fuck you in the ass with this big carrot, lubed only with a little of step-mommy's spit. When perverts masturbate too much, things always escalate, it is important for you to see what happens, now lick it clean, I need this carrot for Christmas dinner!

You know you're in trouble when I call you into my home office and I'm wearing the leather motorcycle jacket you humped and came on. As your step-mother, I reserve the right to always know what my step-son is doing, and I put a in your room as I suspected you were borrowing my clothes to sniff or worse, and I was proved correct! Imagine my horror at the footage of you jerking off on my leather, sniffing it and humping it and calling it step-mommy! You are really such a pervert. You want to make out with my things? Smell them? Jerk off into them? You'll ask me first. But now, you're going to have to lick your poorly cleaned cumstains off my beautiful leather. What is it you love about it? The smell, the creaking, the texture? Jerk off and put on a show for step-mommy while you worship my leather jacket. Then hump it while I hold it on my lap and you kneel in front of me like the leather slut you are. You really wish it was your step-mother you were humping, don't you?

See Pantyhose Payback 1 for the first part of this series.

Your step-mother is really unhappy with your behaviour. She decided to work from home most days for a while, to keep you in line. Your disrespectful mouth must really be corrected. She sits on the sofa in her home office, scolding you with crossed pantyhose-clad legs and high heels. She makes you kneel, and strip, remembering to always obey your step-mother. She you to open her mouth and worship her dirty, smelly heels to prove your devotion, saying you can move out if you won't obey. Something about your step-mother's haughty dominance always makes you give in, and you are soon getting a boner as you suck her heels like a cock. She decides to fuck your ass with the heel too, telling you that your body is hers to do as she pleases with. You're made to jerk off for her, worship her pantyhose, kiss her ass and more as once again she reminds you that you're beneath her and under her control. You're starting to go mad for the erotic scent of her nylon clad feet in these humiliating, perverted discipline sessions.