You knew it was small, of course you did…but…so small she’d break up with you? Ok, maybe she broke up with you because of the fact that you also came in your pants…dammit.
Tag: Small Penis Humiliation
Could a phone number on a mysterious flyer typed to a telephone pole be the answer to your stepmother’s prayers? Sure! You’re such a brat that your stepmom is willing to pick up the phone and call me, adult babysitter Penny Barber. I specialize in naughty, willful boys like you. There’s always an underlying issue that causes such sassy behavior and once I’ve stripped away every last, uh, defense it’s painfully obvious what yours is: a tiny, little baby-sized dick!
And I don’t shy away from the issue either. We do all the things that a babysitter and her ward should do, just with a special emphasis on how tiny your pee pee is! After getting you in the tub, I give you the most humiliating handjob of your life, complements of Mr. Tubby the Duck. Then it’s time for a crinkly, humiliating pull-up diaper. Since you’re really good at snack time and don’t fuss about your bib too much, I even let your cute little thingie get lost in my glorious cleavage for a peek-a-boo titty fuck. After all, shouldn’t a baby-sized dick be as much as possible?
The bottom line is, I promised your stepmom that your behavior would be drastically improved by the time she gets home and no matter what I have to do—diaper you, humiliate your small penis, or even make you eat your own cum—I always deliver. Do we understand each other, little dick boy?
I see you brought all your friends over for game night! Well, you are in luck, I’m going to join! Oh come on honey, I already have a great game in mind… spin the bottle! What do you mean it’s going to be so much fun, and I’m going first! Oh come on son, all your friends know me well, they know I’m a good sport. I’m going to take them behind the couch as not to embarrass any of your friends… or YOU! Watch as I take all my son’s friends behind the couch and plant a “kiss” on them. All these boys are so excited to have their turn, except my son… this might just be the cuck play you need to get your little penis hard!… enjoy me, xo
When the neighbor finds her neighbor is into big dicks and Step-Mommy encouraged bi porn on the internet she decides to be her neighbor’s new Step-Mommy, with her big perfect tits, making him her faggot, sissy slut who takes cock while jerking off his TINY little peepee!
It’s been a few weeks since the last clip and we’re about to go on a f amily vacation. You’ve called me into your room to show off the new bikini you’ve bought for the trip. As you tease me with your perfect body and long hair you tell me to take out my cock and start stroking to your perfection. You tell me I was such a good boy for M ommy when my D ad was away, always following yours and my bully’s orders and you say I deserve a reward. You get closer and closer to me as if you’re finally going to touch me but just at the last second you deny me and put me in chastity. You laugh at me and tell me a fat loser like me will never be touched by a perfect Goddess like you, not even out of pity.
It’s been a couple of weeks since the last clip and step-son has been forbidden from touching himself since. When step-daddy goes away on business I take the time to give My fat and pathetic loser step-son some extra attention.
My D ad is a rich CEO. You were his secretary but now you’re my new Stepm om. Since you’ve moved in you’ve noticed how obsessed I am with you. You tell me I’m just as obsessed as my D ad and you show me how you seduced him at work, teasing him with your perfect face, long hair and tight body. You would “accidentally” drop a file and pick it up in front of him or lean in extra close to give him his morning coffee. Eventually he had to give in and cheat on my M om with you. You tell me these are even the clothes you wore when you first fucked him. You tell me about all the times you two would fuck at work while my M om was at home unaware. Eventually she caught the two of you “working late” and you tell me how she was so shocked she just stood there as you kept fucking my D ad’s big dick. After you had finished he served her the divorce papers right there, leaving her penniless. You can see by the small tent in my pants how turned on I am. You taunt me with your perfect body that my D ad gets to enjoy. You order me to jerk to how you own my D ad’s big dick and his big fat wallet. You say how much smaller I am than him and how a fat virgin loser like me will never be a real man like him. You tell me that you’re going to start leaving your bedroom door open at night so I can hear every moan. Suddenly, just as I’m about to cum, you change your mind and tell me to stop jerking. You say that my cock belongs to you now and I can only cum when you say so.
You are my son and you’ve asked me to come checkout your penis since you’re concerned that it might just be too little. You have no idea that I’m actually a size queen kinda girl, but that doesn’t change the fact that your penis is actually… really, REALLY small. I let you down lightly. with love. I try to make it get bigger, maybe you’re a grower!? But nope. That little willy is staying small. I try with both my mouth and my two fingers but, wow, you really did not luck out in this department! I’m so sorry sweetie. Women love big cocks, and I feel badly for you, so I decide that the only way you’re ever going to see a woman’s real, pleasurable reaction to a cock is if you watch my suck and deep throat my favorite dildo! Its huge, its realistic, and its SUPER fun for me to suck! I LOVE sucking this thing! I compare your tiny cock to my big dildo by opening my mouth wide and demonstrating how my big dildo fills up my whole mouth while yours barely even touches the sides. I am loving but factual in describing the size of your small penis, comparing it to carrots and vienna sausages. Not in a mean way, but with compassion. Eventually I allow you to jerk off (demonstrating with my two fingers) and tell you to release your cum while watching me suck on my giant, favorite dildo!
![Goddess Willow Bouvier – Homework with Step-Mommy [SPH & Tease and Denial]](https://www.momroleplay.com/wp-content/uploads/2024/05/Goddess-Willow-Bouvier-Homework-with-Step-Mommy-SPH-Tease-and-Denial-720x405.jpg)
NB: This was a custom clip and the name “Eric! is used throughout. This contains gentle, teasing, humiliation and some small penis encouragement
You have found the perfect place to do your homework, on the floor, right at step-mommy’s feet; I can keep an eye on you and you get to look up at my beautiful legs and even get a little glimpse of my my panties when I cross and uncross my legs..You start getting hard, fumbling and blushing and in your efforts to hide your boner, you end up dropping your drink all over yourself. I command you to strip, and I am reminded of how little your cock is. Awww it really is a dinky one isn’t it? But don’t worry sweety, step-mommy loves you all the same!
Hey sweetie…oh! Wow. Sorry hun, I didn’t realize you were…jerking off. Oh sweetie, your penis is so small. I didn’t realize. It’s okay you don’t have to be embarrassed…but..wow that is pretty embarrassing. And funny, I can’t help but laugh. And what are you watching? Big booties? Stop. That’s a joke right? Your penis is way too small for those big butts. Look at my booty, it’s even bigger than those. Look how tiny your penis is compared!