Detention

Author's Note:

Mistress Pepper and Sophie are "anonymized" versions of me and my slave-girl. The real me. All of my stories are (or should I say will be) my memories of a session with a sub. Thus, they are true stories. Only in this version details have been changed to protect the sub. I do live in Mobile about 10 months of the year (the remaining two I spend in Nizhny Novgorod, Russia, where my father is from and lives), and almost all of my subs live in Mobile or a bordering county. I'm originally from Baldwin County, next door to Mobile. I moved across the bay to attend USA. As is/did Mistress Pepper. But I'm not a blond. And you'll most definitely have to guess at my bra size!

And remember, the names and such have been changed in this version to protect the slutty. Only Princess Lilly appears as herself. But she truly has no concept of shame.

Session Date:

28 September, 2020

This Story Released:

08 December, 2020

Detention

Prologue:

In case this is the first of my stories you've read, there are a few things I've skipped over in this story since there are several other stories I've written about this same sub. I tend to write a story after almost all of my sessions with my toys. But I publish very few of them online.

My name is Pepper Rodgers. I'm a 19-year-old Domme, living downtown Mobile, Alabama. I have a decently well-stocked playroom in the second bedroom of my fourth-floor apartment (most of my neighbors are corporate types who aren't always around, giving me a lot of privacy, even in the halls and elevators). I also have a decently stocked toybox. I prefer my toys to be older than I am, around 30-42 years old. I prefer men for myself, however not for my toybox. When it comes to toys, I find women and couples to be far more amusing. Single men tend to be needier, and often too clingy. But that doesn't mean I don't have a few of them in my toybox. I do. They just don't have the same chances of getting there as couples and single women do.

I'm petite. Actually more "tiny" that petite. I'm 5' 1.75" and 91 pounds. I'm not bony, though, I've curvy, like a small-sized woman. I have blond hair down to my shoulders and blue eyes. Oh, and my chest is the only place I'm not small. I'm a 32-D, and I'm very pert. Which makes me popular with the boys.

I'm also slightly bisexual. I'm attracted to men, not women. I would never choose a female partner for even a date, let alone for sex. But I'm not opposed to masturbating with a female toy. Sophie happens to be my favorite sex toy to pleasure myself with. Her tongue has two big advantages over my vibrator: one, it's very delicate and tender. Two, no matter how much I use it, its batteries never die at the worst possible moment! It's better than fresh bunny batteries, it just keeps going until I want it to stop. And I don't even have to hold it in place!

When I want sex I never use one of my toys. I never allow a toy touch, or even see, all of me. And I never bring a toy to my bedroom. Nor do I chose a woman. I pick a man, usually one I find in a club or cafe, or wherever. I flirt, dance dirty a little and if he meets my standards, I ask if he's interested in a one-time-only, no-names-exchanged, hook-up. I've never been turned down.

I have a few standards for my hook-ups. I never pick a guy I know or even just see around. And I insist on a cock between 7 and 9" long and 1.5" across, plus or minus a small bit. I won't touch a guy who isn't circumcised, either. I hate the way the foreskin feels inside me. I want to feel that fat head. The dirty dancing gives me plenty of time to tease a guy hard and feel for myself what he's got. It's the only way not to be disappointed. Guys always lie about their equipment!

Sophie is my 19-year-old live-in slave-girl. She's slightly petite at 5'4" and 119 pounds. She's pretty, too, with long honey-blond hair, green eyes, and a 34-B chest. Sophie is extremely devoted to me. So devoted, and so happy as my slave, that despite not being attracted to women, she's a virgin with men. She serves and pleasures only me, and those I give her to. And while I use her, even with my male toys, I won't allow any man to touch her pussy or penetrate her bottom. Those are mine. Only mine. I've owned her since she graduated high school, but I've known her longer. Since about two months after her 18th birthday, which was also about two months before she finished high school.

I have three BFFs, (Isabelle, Reagan, and Ellie) none of whom are into my little games. But all of whom occasionally creep into my stories. After all, they are my BFFs so they tend to be around. Luckily they're not offended by anything they happen to see. They're just not eager for me to put on a show on their account.

I also have a circle of five other women friends, all of whom are Dommes as well. Andrea (26), Janelle (35), Colette (39), Diane (43), and Olive (44). we usually get together every couple of weeks for coffee and a little chat about who's doing what to whom lately. We sometimes share, or loan, our toys to each other, but not that often. Sometimes we do a favor for each other, such as providing something different for a toy. Mostly we do what girls do: we gossip.

I get all of my toys through networking. It's almost always either one of the women in our circle who has a toy she doesn't want and offers to point it at another who is interested. Or sometimes one of my toys tells someone, who tells someone, and so on until someone asks my toy to introduce someone to me. Rarely it's someone I don't play with, but who knows what I'm into, who asks me to meet someone. I get plenty of emails inquiring about meeting me, and while I will email and maybe chat with a sub online, I haven't yet met any. I won't rule it out, but meeting online is risky enough that someone would have to convince me before I'd think about it. A girl's gotta be careful!

Chapter 01: The Set Up

I like doing "favors" for my Dom/me friends. It gives me the chance to play with their toys. Toys I wouldn't otherwise get to play with. And the one thing that I like more than almost anything else is variety in my playtime.

Dmitri is a Dom I know somewhat. He, and his wife (a fellow Domme), are friends of my friend Nikolai. Like Nikolai, Dmitri lives in Pensacola, not Mobile. It's not nearly as far away as it sounds. About 30 minutes, and that's with some traffic on I-10. The only thing between the two cities is Baldwin County, where I was born and raised.

Dmitri doesn't often ask for favors. I think this is the third time he's asked. He does have his wife to share his toys with. There's only one thing I have that She doesn't. Youth. I'm 20. His wife is in her mid-40s. Otherwise, my style and theirs are pretty similar.

The favor is Janette. Dmitri tells me that's she's a 40-year-old Baldwin County housewife. I know Baldwin County housewives rather well, at least as a type. He tells me that her husband is some sort of banker that Dmitri does "business" through. I know enough about Dmitri to know I'm better off not asking about it. I doubt he's doing anything illegal, he's too smart for that.

He tells me that Janette has been his challenge project. Humiliation is what arouses her. The worse she's degraded, and the more publicly it's done, the hotter she gets. The trick for him has been humiliating her both publicly and safely. By safely I mean where it won't affect her, or her husband's, reputation in the community. That, Dmitri tells me, would be devastating for them. I'm pretty sure he means for his business relationship, too.

He tells me that Janette is a cry baby. She always cries for him, as she's enduring whatever shame he thinks up for her. And she's a modest woman, at least in public. But lately, over the last several sessions, she's becoming comfortable with Dmitri, and with being nude in front of him. She also hates anything lesbian. She's never been comfortable with his wife touching her. Or any other woman.

Plus she has three kids, a 16-year-old son, a 10-year-old son, and a seven-year-old daughter. Those three have, as with most Baldwin County housewives, turned Janette into a soccer mom. Dmitri is confident that Janette will find it especially humiliating to be forced to submit to a much younger woman. Someone who could be the age of her son, or at least close to it.

Naturally, I agree to humiliate her. It's an irresistible offer for me. There's nothing that arouses me more than humiliating a "mom-aged" woman. I've just never figured out how I developed that little kink. I ask Dmitri what public humiliations he's subjected her to before, so I don't repeat anything. Whatever I dream up for her, I want it to be fresh.

And I want it to be a surprise for her. So far, she's known all of her humiliations were play. Sure, Dmitri has stripped her naked in front of strangers, but he's done it at his house, where Janette knew it was playtime. Thus, she knew it was "safe humiliation," that the audience, whoever they were, were also part of the scene.

My idea is to humiliate her in front of strangers, but this time, Janette isn't going to know that it's safe play. It will be, but she's not going to know it. It's a humiliation that will be far deeper than anything she's ever suffered at Dmitri's hands. Now she's not going to know that her audience is part of the scene. She won't know that her secret will be kept.

It's something that's not easy to arrange. There are a limited number of public places where I can control everything. But the hardest part of it is summoning the toy without letting the toy even suspect she's being summoned to a play session. At the least, the toy will figure it out when she arrives and finds her Mistress there.

But Janette is Dmitri's toy. She doesn't even know that I exist, much less that I'm a friend of her Master. Dmitri won't be present for this scene. It's my scene, not his. I have an idea. And if I pull it off right, Janette is never going to know this was just a scene. At least not until it's over.

Baldwin County is the wealthiest county in Alabama, which, I know, isn't saying much. But it's not an especially populous county. It's more the ritzy suburb of neighboring Mobile, Alabama and Pensacola, Florida. That means it doesn't have that many schools in it. There are three high schools. And I have a toy that's a teacher in one of the three. It doesn't me much to figure out it's the same school that Janette's son attends.

I wonder if Janette knows Felicia, my teacher-toy. It's definitely possible. She teaches English, and that's a class everyone takes all four years. There are several English teachers, though. But it is his third year taking those classes, so it's entirely possible that one of the five semesters, she's been his teacher.

I call Felicia and ask. I'm hoping that she can at least convince one of his teachers to help out and summon Janette for something like a meeting. A meeting that the teacher will not be attending. But Felicia surprises me. Not only does she know the student, but he's also in her third-period class this semester. She doesn't need to lean on one of her teacher friends. I can just lean on her.

But I don't have to. Felicia is a fairly obedient toy. When I tell her to summon Janette for a parent-teacher conference at a time when we can be assured of privacy in the classroom, she simply says "yes, Ma'am," and suggest 4:30 on a Monday afternoon. According to Felicia, that's a time when the building will be mostly empty. The time when the fewest extracurricular activities are going on, and most of the teachers will have finished whatever conferences and detentions they have and left. I tell her that will be fine. I can be there.

Then I tell Dmitri what I have in mind. He loves the idea and agrees to my one condition: that nothing at all be said to Janette. Not even that he's "loaning" her to another, much less to me. Janette is to think this is a real parent-teacher conference. She's to have no idea that anyone knows she's a toy. And even less of an idea that she's going to playing.

I have Felicia set it for a week from Monday. That gives her plenty of time to schedule a conference with Janette. And it gives me time to set up for it.

Now that it's Monday afternoon, I arrive at the high school just before 4:00, when I told Felicia to be expecting me to arrive. The halls are already almost deserted. Perfect. There's always security at the front door, where visitors have to sign in and out. If security is gone, the doors are locked. But there's never security at the teacher's door. I call Felicia and have her come let me in that door. That way, there won't be any record of my being here.

I have a few friends with me. I didn't tell Felicia to expect them. I have my BFF #1 Izzy and her boyfriend with me. I have Paige, my 18-year-old live-in slave-whore with me. I have two other girls, Allie and Kate, who are freshmen at USA with me. I have another boy, Danny, a freshman at Bishop State College where Sophie, my 19-year-old live-in slave-girl and handmaiden, and Paige, are students with me. They all have two things in common. First, they're at least eighteen. Second, they look young, and they're dressed as high school students would be.

Felicia looks surprised to see the group with me. I hadn't told her they were coming. But I never tell my toys anything. Felicia should be used to that by now. She quickly walks us to her classroom. It's clear that she would prefer no one see any of us. I can't blame her for that. I would too. It would only necessitate explanations later.

No one sees us. The halls are that empty. And the walk is fairly short. Plus we avoid the main hall, the only one that likely has anyone in it.

As soon as we're in Felicia's classroom, I tell her to sit at her desk. I don't have to say anything more. She takes the seat behind her desk, crosses her legs, and folds her hands in her lap. She sits up straight. It's the position I expect when I tell my toys to sit. And Felicia has been around enough to know that disappointing me guarantees her a swift punishment. She stays silent, too, something else I demand of my toys.

I tell the others to help themselves to the student desks and to mix it up. I don't want the boys sitting together. I want them scattered in with the girls. "Gawd, I never thought I'd be sitting in one of these desks again," Izzy giggles as she pulls her boyfriend to sit beside her.

All of the "students" know that they're participating in one of my scenes. They all know that it's going to get "interesting" and do so fairly quickly. My scenes always do. They also know they're never to speak of it. I trust they won't. I picked people who have all been in an audience before and kept the secret. To most of them, it's just a show. Like reality TV. Like the proverbial train wreck. How low will this woman go? How far will she allow herself to be humiliated? It's as entertaining as the Kardashians! Only this is one hundred percent real.

"Okay, everyone!" I announce. I glance over my shoulder at Felicia, "you, too, bitch." I turn back to the students. "Here's the scene. You six are here for detention. You naughty students were caught talking in class, or whatever, it doesn't matter. For detention, you'll be given an assignment to complete. I don't care if it gets done, or not. I don't care how good of a grade you get on it. I'm not even going to bother grading it! I just want you all to look like you're hard at work on it.

"Felicia, that's the teacher bitch up here, has a parent coming in for a parent-teacher conference at 4:30. When the student's mom gets here, you are all to be diligently working on your assignment or at least look like it. From then on, pretend you are real students and act accordingly. High school students. It hasn't been so long that you all can't remember high school."

None are still in high school. Although three of them graduated only a few shorts months ago, including Paige. Only Izzy and her boyfriend are 20. The rest are sophomores, so they're 19. There is no way I would have used actual students for this. The risk, should they gossip, would be too high. But I don't tell Felicia that. I'll just let her assume whatever she assumes.

I hand out some textbooks and "assignments." It's on grammar, something appropriate for an English class. It's a long and fairly advanced assignment. It's one I downloaded from the school board's website. One that Felicia should use in her class. The textbooks are from Felicia's stock in the classroom. The same ones her students have. Anything else would be an inconsistency that should be a clue for Janette. Should be. I doubt she'd actually pick up on it. But always better safe than sorry.

The first sight I have of Janette is when she tentatively comes through the door of Felicia's classroom. I've seen a couple of pictures of her before now, courtesy of Dmitri, but I've never seen her. I couldn't have. It would spoil the setup. She'd know I was a friend of her Master.

Janette is average in height, around 5'5". She's also probably average in weight, I'm guessing around 140 pounds. Today she's wearing a turtleneck sweater over loose-fitting jeans that I can already tell have a high-end designer label on them. Probably the sweater, too. I can see it's cashmere. It's not snug-fitting either, as all of my sweaters are, but loose enough that it obscures the shape of her body. But even still I can tell that her body is not going to be heavy. It will be, as Dmitri said, shapely.

Janette has a slightly rounded face with soft features. There's neither an ounce of extra weight on it nor a sharp or angular feature to be seen. She has green-gray eyes that sparkle. She has a slightly long, smooth nose. She has a slightly narrow mouth framed with a pair of very plush and full lips that are a medium shade of pink. It's all framed by long, straight hair that hangs down to her shoulder blades. Her hair looks like it's naturally dark brown, but now it has so many blonde highlights in it that it looks to be two different colors, brown and blonde, all mixed up together. Except at the bottom, from her jaw down, where it's dyed all blonde. It's a fairly unique style, in that she does little with it besides brush it out. It hangs close to her face, and down to cover about half of her forehead.

Of course, now most of that face is covered by a "cutesy" purple mask with a picture of a very adorable poodle on it. Welcome to the new reality. No one leaves home without a mask. Not even for school. For now, my "fake students" have on generic plain masks, except for Paige and Izzy. Paige always wears a pink mask with frilly white lace trim that I got for her. Izzy seems to never wear the same mask twice. Today's is bright pink with random-colored polka dots on it. Felicia has a yellow and blue mask, the school's colors. Mine is crimson with a giant Alabama Elephant on it. It is football season, and a girl should support her teams!

"Hi, I'm Janette Morris, Tony's mom..." Janette introduces herself to Felicia. It's still early enough in the school year that they haven't met yet. The traditional parent-teacher night is still a couple of weeks away, and now it's going to be so uncomfortable for Janette!

I'm sitting beside Felicia. Today I've worn one of my professional business suits. And like most of my stuff, it has a designer label. A girl has to look good! But more importantly today, I want Janette to notice my youth, but also to project a professional image. Felicia introduces herself, then she introduces me as "Ms. Rodgers, her teaching assistant." Janette won't know the difference. But I see the little smirk flash over Paige's face, even with that mask on.

I signal Izzy with my hand. It's just a little motion, but Izzy is watching for it. Janette couldn't possibly see it. I use the desk to hide my hand from her eyes. Izzy quickly raises her hand and waves it around to get Felicia's attention. "Ms. Miller, could you please help me with this? I swear there isn't a single gerund anywhere in this paragraph!" Izzy tries to sound desperate and frustrated. I nudge Felicia with my foot, telling her to go help, Izzy.