You can’t go out with some girl tonight, you’re supposed to spend the evening with step-Mommy! Well, if you insist on seeing this…tart, then step-Mommy is going to insist that you keep it in your pants, or rather — in your diaper! Now, drop your pants and show step-Mommy what she’ll be padding this evening. Wow. That is small! You should be grateful that step-Mommy is doing you the favor of pampering your petite penis, because I’m sure this girl would lose interest if she saw it. She might even laugh, and of course you know you can’t count on some girl to keep a secret, not like step-Mommy will.
Tag: Penny Barber
You little perv! You may very well be the filthiest, naughtiest client that has ever hired me. I can handle the highly inappropriate questions during my interview; I can even handle finding all the kinky ABDL toys you left around your house, but I draw the line at lowballing me! You clearly need a Step-Mommy-Dom to take you in hand, someone who can control you with her gorgeous, fat MILF breasts.
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?
You look nervous when Mommy asks you to help with the laundry, and rightly so. It’s not long before I find a VERY sticky pair of your boxers. You’re so embarrassed that you quickly lie and tell me it’s pee. Mommy thought we could be mature about this, but if you really want me to believe you’re having accidents then someone is going to have to start wearing diapers.
Hey there, couch potato. Think you can beat stepMommy at a game of basketball? If you win, I’ll buy you that expensive new gym bag, but if I win, you have to do whatever I say for a whole week. Game on!
I’ve been texting you for hours without a reply, and at this point I have to assume that you’re just not coming over. Whatever. Your step-mom knows how to entertain herself! Unfortunately you finally come home right as that entertainment is coming to a climax—all over the kitchen counter! I’m coming and squirting like a complete slut just as you walk in the door and I can’t seem to stop. I’m sorry you had to see me coming, sweetie!
So you lost the big game today and…kind of humiliated yourself. Mommy is still proud of you for trying. Please don’t give up, sweetie. Let Mommy take car of you tonight before you make up your mind. I prepare the bedroom and remove my silk robe to reveal a red micro bikini. After rubbing your sore muscles, I take my top off and show you what Mommy is willing to do after every game to keep you motivated. I lick your powerful cock while letting you know how badly I want you to be an athlete, and then—when you convince me you’re committed—I let you fuck my proud wet pussy to several screaming orgasms before you give me a hot cream pie. Good boy! XXX
Well, look at you all dressed up! Big plans today? You’re going to ask a girl out… okay. That’s fine. This is fine, but get yourself to school today.
I’m waiting for you when you come home. Apparently she said yes, which is… just great. Mommy recognizes that you’re all grown up and have new needs and desires. Why don’t you let Mommy help you indulge in those desires. We’ll start by smoking to calm your nerves. Isn’t that better? Now watch Mommy strip for you. I play with my big juicy tits and rub my pussy over my white lacy panties just to get you nice and hard.
Oh my god, you’re HUGE! That’s the most beautiful cock Mommy has ever seen. I’m going to make you feel so good, sweetheart. I kiss and worship your cock, taking as much of it as I can in my eager salivating mouth. I can’t wait to get it into my aching jealous pussy. Mommy will show you that she can take care of your needs better than any silly girl you meet. I ride you cowgirl to a to a long squirting orgasm before getting on my back and letting you take me as hard as you can. You fill Mommy’s pussy full of your cum. Now go get cleaned up, sweetie, before we take another “smoke break.” XOXO
I can’t believe you asked me for an advance on your allowance. You’re such an irresponsible young man. Now, give me your keys, Step-Mommy needs to borrow your car. I really need to get to work, honey, so just tell me what you want me to do. I give you all the money in my purse and ask you as nicely as possible before you make me strip for you and suck your beautiful cock. Despite my frustration, I let you know how much I enjoy blowing you. It makes me so wet that I agree to let you fuck me and cum in my pussy before you finally go looking for your keys. Thank you for helping Step-Mommy unwind before her big presentation today, sweetie! XOX
Penny is chatting with her friend Becky being a bit defensive about how she needs to get laid. The truth is it has been a long while and she is really needing dick. A call comes in Jenny (whose always over dramatic about something ) and Penny answers. Jenny is all worked up because she found a dicpic on her precious little Kaitlyn’s phone. Penny doesn’t see the big deal. Kaitlyn is 18 and old and not exactly an angel. Jenny then tells Penny the pic is from her stepson Jayden and sends the pic to her. Penny laughs as she looks at the picture until she gets a sense of scale. There is not way THAT belongs to her sweet Jayden. Penny says she knows it wasn’t Jayden and will prove it.
After hanging up Penny slips into Jayden’s room since he isn’t up yet. She sneaks up and looks under the covers and is stunned for a moment. Penny quietly leaves his room makes a plan.Maybe he’s a shower, suer it looked big but he wasn’t hard so she can’t be sure what it really looks like.
He only brought so much clothes with him to visit, maybe everything but some gray sweat pants can end up in the wash, Then a little massage and she can see the outline of his cock and know if it really is the same thick monster cock she saw in the picture.