You finally get to go on a date with me and things are…not going well. I show up in a gorgeous, slutty cocktail dress, but instead of taking me to a nice restaurant, we go to some burger joint. You can tell that I’m trying, but I’m just not
Every single time I take you around my friends, you completely humiliate me! Even when I tell you what to say, how to act, what to do, you still find a way to embarrass me. My friends are sophisticated people, okay? You can’t keep babbling about
I knew the little blonde baby doll named Ella that my husband had left me for was a clueless tramp but I did not realize she was an immature little brat as well. First, she couldn't even be bothered to put her phone down to answer the doorbell and
It seems Dr. Barber referred you to me for a diaper prescription and none too soon, since you appear to have wet your pants. You are already diapered and in plastic pants? You must be quite the little wetter to have soaked through to your clothes. I
I must say that you’re just as attractive in person as you were in your application. But do you really think you’re ready to be Penny Barber’s submissive? Strip for me and let’s find out! I pull out a pink trial collar and you immediately begin to
I really do enjoy tutoring but some little troublemakers need discipline to help them focus. I find diaper discipline to be very effective and my students find it to be very embarrassing. If your girlfriend, Kiki, can't stop flirting and flashing
When I show up at Sam’s place for a “meeting” he’s a little thrown off. Before I’m even in the door, I lay into him, listing all the things that he does that annoy me, telling him how he doesn’t even compare to my other employees. I rant and
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny Download FREE Diaper Fairy Sissy Potion - October 28, 2022 - 125.22 MB
You are the worst roommate! But you know what? I’m not going to stand for it anymore. While we play some video games you “accidentally” consume a diuretic or two in your (my) orange juice. Imagine your surprise when you start wetting your pants
I thought it was embarrassing enough that your Mom thinks you still need a babysitter at your age but then she explained that you need to be DIAPERED at night because you still wet the bed. It was so hard to keep a straight face while I promised to
As an agent for writers, you have to know when your clients need to be coddled and when they need a firm hand. As a rising young star, Ella Nova badly needs both. Luckily, I have the humiliating diapers and spanking skills to make sure she gets
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX Download FREE - Neighbor Makes You Her Diaper Stud - July 14, 2023 - 82.2 MB
I should have guessed what was wrong when I saw you staring at a ruler and crying but maybe your little thing isn’t as little as you think. Maybe Mommy should take a look for herself, just in case. Don’t be shy, I’m just going to take it out for a
I just got off of the phone with your teacher, sweetie, and she says you’re grades are slipping. She also told Mommy that you’ll need to have all of your distractions minimized from now on. I’m going to set up your widdle work station with a sippy
I am excited about all the fun we can have tonight but I do have a question about all this baby stuff I found. I don't see why your Step-Mommy would leave all these diaper changing supplies right here if she didn't want me to find them. A bedwetting
It’s here! Today is the day you wear your diaper in public. Mommy-Dom is going to take you to the Kinky Fair. Before we go, I dress you up in the girliest diaper and the girliest outfit in my collection. I love the way your little thingy bounces
I think it is so sweet that you guys are having one last rest over before college starts but your mom did send over some special supplies and instructions for you. Now don't be too embarrassed but I am going to need to diaper you so please strip and
I’ve been feeling very feminine lately, which means that I want to dress you up in the girliest, cutest little diapers I could find! Since I control your cute little cock, we both know that I can dress it up in whatever hyper girlie, soft, adorable
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX Download FREE Click, Click, Piss - August 05, 2022 - 99.4 MB
I’ve got a special night planned for you, sweetheart! I’m going to pamper your pretty little sissy bottom over an adorable diaper. You just lie back while Step-Mommy teases you with powder and special bottle before preparing your cute tushy — one
Watch the full clip in my store! XO Download FREE Mommy's Little Monster - October 19, 2021 - 223.83 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX Download FREE Soaking Each Other's Diapers - November 11, 2022 - 126.4 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX Download FREE Fucking With the Principal - January 13, 2023 - 131.6 MB
If you had known that the punishment for being caught with no less than THREE PAIRS of my panties would be diapering, being dressed like a sissy girl, and humping your pillow to orgasm while worshipping my feet, you would have done it ages ago! And
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 guess you’re out of practice, because Mommy
We’ve just been at each other’s throats ever since I married your father. Yes, I am a lot younger than he is and yes, I have noticed you constantly staring at my breasts and I’m reasonably certain that you’ve been pawing through my bras as well.
My gorgeous stepdaughter needs new photos for her portfolio, but the photographer informed me that the creepy neighbor boy—YOU—photobombed ALL her latest pictures. They’re ruined! Hell hath no fury like an angry stagemom. I hold you down and strip
