I’ve been enjoying keeping you all locked up and I just can’t resist the urge to tease you during your morning diaper change. I’m mean, but sweet, baby-talking to you and reminding you that I’m in charge of you, your diapers, and your cute, little

A Penny Barber Fantasy. Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny Download FREE You Belong in Diapers - December 09, 2021 - 222.45 MB

I was thinking it would be fun to humiliate you in a big, puffy diaper but then I had an even better idea. It would be so much more humiliating to use little dolly diapers for your little dolly dick. The adorably tiny diapers are the perfect size

I come in the interview for a babysitter job, but I don’t exactly look like your other applicants. I’m wearing a hot pink bodysuit, hot pants, and thigh high stockings. I talk about how I usually work nights and am usually really good with people.

Mom helps you to be an obedient boy and you always enjoy our wanking sessions more when you are nice and comfortable beforehand. As long as you stroke it exactly like I tell you, then you will get to see Mom’s big beautiful breasts before your

I am so proud of the strapping young man you have become but you will need more than good looks and a winning personality to be a success. That’s why I am implementing a sexual reward system to make sure your academic record matches your potential.

Watch the full clip in my store. XOX Download FREE Before You Go to College - March 05, 2021 - 144.74 MB

You’re in diapers whether you like it or not, completely. But it isn’t all bad. I’m going to show you just how sensual being my widdle diaper boy can be, but giving you a warm, soapy enema and sucking your cock silly! Plastic pants will ensure that

It was so fun to go out as Batgirl, and you looked GREAT as Batman. You fill out that costume nicely, sweetie, but Step-Mommy could still take you in a fight. Let’s go! Did you get an erection from wrestling with me?! It’s sooo…big. Straddling you

Why did the little cucky boy run away from his babysitter after bath time? Are you embarrassed to get diapered by me or is there another reason you ran off to your Mommy's room all naked? I wonder if it has anything to do with the pair of panties

Smells like somebody is burning something besides firewood wood over. I knew my darling boy couldn't go away to camp without getting into trouble so that is why I decided to be a chaperone on this trip. Now if you do not want me report this to the

Your father finally had me served with divorce papers, so you have a very tough decision to make: do you want to live with me or with your dad? You show me exactly where your loyalties lie with a 90 minute fuck fest on our white leather couch. We

This is the moment we’ve been working towards for so many years. I open and read your acceptance letter and…you got in! I prepared something special to celebrate this moment. Can you guess what it is, sweetie? Recounting all the sacrifices you made

I catch my naughty little step-son sneaking around my room and finally confront him about playing in my panty drawer! I saw him with his hands down his pants in here once already and I suspect he has been messing with the old baby things stored in

Seems that Mommy tried to get into a dress that was a little too tight around the shoulders and now I’m STUCK! Unable to get into or out of the dress, I really need your help sweetie. Don’t worry about the box of sex toys on my bed or the kinky

I really, really need a diaper change, Daddy. I am totally soaked and I am afraid my little skirt is going to get wet if you don't change my diaper soon. I will do anything to earn a fresh diaper. A blowjob seems like a fair trade if that's what you

Good morning, sir, rise and shine. Looks like a certain business baby absolutely soaked his overnight diaper. We better get you changed fast or you might be late for your first meetings. I was thinking about letting you wear some thinner diapers so

I guess somebody may have had a little more to fun than he could handle last night. Does Mommy need to help her hungover little man get himself sorted out? Oh wow, looks like your friends may have had a little fun with you last night because you are

I have always been your biggest fan, Batman, and I am just so grateful to meet you. I would do anything to become your new Batgirl and I mean anything. All of my holes are yours to use and I would consider it the highest honor to have you cum on my

Oh, honey! Mommy is sooo glad you’re home. There’s something I’ve been meaning to ask you since your dad left and — now that I’ve had some liquid courage — I’m ready to just ask: would you satisfy Mommy sexually for your allowance instead of doing

Good morning, sweetie! I got up early to make you breakfast since you have such a big day of activities ahead of you. Are you alright? You have the strangest expression on your face. Wait — do you have an erection?! What’s that from? There is

Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny Download FREE Mommy Catches You, and Helps - December 02, 2021 - 224.46 MB

It’s BBQ season again! That means I get to tease and torment you at all the family gatherings, slinking around in a slutty little bikini and making sure that you see my tits, ass, and FEET, adorned with sexy, little gold toe rings and a sparkly

I know these diapers are embarrassingly babysish but they were the only ones I could find big enough for you. I wish there was another way to deal with your bedwetting but I think it is time to accept that you need diapers. It won't be so bad, no

I am very happy about your report card but it is silly that you think I will believe that dirty story about your tutor. Maybe I should call Ella right now and ask her if she really got naked and sucked your cock to help you study harder. Well, that

Okay, sweetie, I’ll stay home sick from work if you promise to take care of me. I ask you to grab mommy some blue cold medicine and something to nap in. You pour from the wrong bottle—which I take without checking—and bring me some slutty lingerie

Another day started with persistent little kisses all over my thighs but before I can even get my glasses on or even say "Good morning" I feel my legs spread open and my nightgown pulled down. My darling boy is getting a little too with his