After your last punishment for spying on Step-Mommy, I told you to be on your best behavior for two full days. You promised me that you would be my good boy, but I had to know for sure before rewarding you with a full orgasm. Unfortunately, your browser history shows that you’ve been very, very bad. You’ve been watching all kinds of porn and jerking off without permission! This time, I’m not letting you off easy. I’m going to make you edge yourself to my naked body, then pump out a huge load of cum. But I’m not letting you stop then! You have to keep stroking hard and fast, rubbing the sensitive tip of your cock after you finish cumming. Maybe this harsher punishment will finally teach you that I’m the one who owns your cock!

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Having become something of a lazy, useless step-son recently, I command you to fix the broken toilet. But when I come back in to check on you, I find you’ve somehow managed to get your head stuck in the bowl. Unfortunately for you, I have an important meeting to attend today so will have to leave you there until tomorrow. But the following day, upon receiving your report card in the post, I’m far from impressed by your grades. Well, I need to use the toilet and as punishment for you, I’m going to do it whilst your head is stuck down there. Unfortunately for you, it’s a number two and it will likely end you as it’s a going to be a big one. And if it doesn’t end you, I’ll just leave you down there and keep using your face as my toilet until it does!

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How embarrassing to be called into your teacher’s office for a meeting. It doesn’t surprise me though you have always been a naughty boy.
I can’t believe what Miss Cox is telling me though, is this correct, that you’ve been watching BUSTY MILF PORN in class?
Luckily for you Miss Cox, has persuaded me to help her give you some discipline and not just kick you out of school! So, you sit there, and do exactly as you are told… Whilst we show you exactly what BUSTY MILF PORN is all about, and hopefully you’ll be able to get it out of your system!

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I’ve had my eye on your d a d the entire time we’ve been dating. He’s everything you wish you were. Hot, successful, funny, smart, and most importantly-rich. You were such a fool not to see this coming! When he invited us to the country club for the weekend I knew what he really wanted….. I just couldn’t resist fucking him! Now he’s making all sorts of promises to Me and I just know I’ll have your inheritance drained before he even croaks. You can call me Step-Mommy Valentina now!

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We need to have a chat, darling. I know you’ve been sneaking around and jerking off to me, but I’m not mad about it. I know how distracting I can be, especially since I mostly wear lingerie at home. I want to help you have a full release to let out all of that pent up frustration. Let Step-Mommy guide you through a rewarding jerk off session while I slowly strip naked. Are you ready to be Step-Mommy’s good boy? You just have to promise to keep this our little secret…. KEYWORDS: Taboo Roleplay, Taboo Fantasy, Step-Mommy, Encouraging Step-Mom, Sensual Domination, JOI, Jerk Off Instructions, Jerk Off Encouragement, Cum Encouragement, Nude Femdom, Strip Tease, Curvy Goddess, Tits JOI, Ass JOI, MILF, Lingerie

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You’ve been having problems with your Bully at school for a while now and because I felt bad I decided I would rather the Bully punish me instead of you, and he agreed to do it but only if you watched it the whole time. I start out explaining to you that I am going to sacrifice myself to save you the trouble because I know that men just need an outlet for their masculine aggression and I’d rather it be taken out on me than on you. He starts by roughing me up a bit before he collars and leashes me to take complete control. Once the collar is on he moves on to paddling and spanking me as hard as he can while I whimper and cry out, looking at you the entire time. After beating up my holes and ass he brings me to my knees in front of him to give him a rough and sloppy blowjob before he sits down and starts shoving my face into his ass. I’ve never licked a guy’s ass before so this was especially difficult for me but I did it because I want to protect you. He made sure I was really in there by pushing my head down with his hands and sometimes even his feet. After nearly 20 minutes of pleasing him that way he stands up and covers my face in a massive load that is bigger than any cumshot I’ve ever seen, and I mistakenly thought that was the end but he had other plans in mind. As I sit there utterly defeated, he then covers my face and dress in his piss while I hold back tears from being so humiliated. By the end of it I am soaked, bruised, and covered in fluids but it was all worth it to protect you from your Bully.

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You’ve come over to your best friend’s house and his mother greets you and invites you to sit in the kitchen while she cleans up. You’re going with your friend’s family on a weekend getaway, and your friend and his father are out running errands. While your hanging out with your friend’s mom, you can’t help but notice that she’s barely dressed, hard nipples poking through the thin fabric of her robe. After a few minutes of talking her big beautiful breast pops out and you can’t help but notice it. Your friend’s mom notices the bulge rising in your pants and starts asking about your experience with women. She’s actually quite delighted to find out you’re still a virgin, and muses about how much she could teach you. Well, she has a nice surprise for you on the weekend getaway…consisting of lots of closeups of her beautiful big tits, her wet, hairy pussy, and her moans of orgasmic bliss while she lets you cum inside of her! This is a virtual sex tape you aren’t going to want to miss.

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Sweetie, I wanted to talk to you about something… Since I’ve been living with you and your fâther, I noticed no girls ever come over to visit you. Is it safe to assume you don’t have a girlfriend? And that you’re maybe still a virgin? Oh that’s ok darling, you can tell your step-mommy. That’s what I thought, you’ve never had relations with a woman. I would hate you to stress about it and pursue girls, so I’d like to propose you and I enter a special kind of relationship – MOMnogamy. It’s a relationship where you stay my virgin boy forever. You seem apprehensive about it but I can see the erection in your pants, sweetie. Why don’t you just give it a chance, take your cock out, and stroke for step-mommy? You’ll love it, I promise.

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