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A Day In The Life Of A Cheeky Student

You can’t believe you showed up late for assembly. You have friends who warned you it was a bad idea, but it was just so easy to hit the snooze button. One of the administrative assistants ushers you in with a disapproving look, but she doesn’t send you to join your classmates. You can see them, all eyes on Principal Hayes as he welcomes everyone to Cheeky Academy. A few of them look bored, but most appear a little anxious. You, however, are off to the side.




You hope you are pulling off a bored look yourself, but your stomach is in knots. A few of them glanced your way when you entered, and they’ve made the connection of your appearance with the empty chair in the second row.


You see Mr. Topper looking in your direction. He is eyeing you, and it makes you nervous. He wasn’t impressed when you were late to class during regular term, and he certainly doesn’t look pleased with you now. Hard to pull off nonchalance, but you do your best to act like you don’t notice.


The thing is, Mr. Topper knows how to make you notice him, if that’s what he wants. And apparently he does, because the moment the other students are released, he is right there next to you. Your mouth opens, ready to spill the usual excuses, but he stops you before you can start.


”I don’t want to hear it.”


Before you can blink he has taken your arm and turned you sideways, and his hand is landing hard on your backside. It hurts even through two layers of clothing, and more than that, it is embarrassing! Everyone is scurrying to class, and here you are being spanked before you’ve even had time to sit down.


He flips you up just as abruptly, and you take a minute to adjust your clothes as he scolds you – plus it’s easier than looking him in the eye right now. “I hope this isn’t a sign of how your day is going to go. I won’t speak for your other teachers, but if you put a toe out of line in my classroom, my belt is coming off. Is that clear?”

”Yes sir,” you mumble, grabbing for your backpack and heading to your first class as quickly as you can. He doesn’t stop you, for which you are grateful. You make it just before the bell rings, sitting a little too hard and being promptly reminded of what just happened. For once, you’re glad for a front row seat — the only eyes you have to meet are Ms. Lashes as she hands you your first assignment of the day


“Good morning, students. Glad to have you all here today. I trust you all completed your reading assignments, so the quiz I just handed you shouldn’t be difficult.”


A quiet groan rolls through the classroom, which covers your sigh of relief. You didn’t go to any great pains to complete your work, but you did look at the material. After a quick glance at the paper on your desk, you actually relax. You know most of these answers.


You’re aware of little besides the scritching of pens on paper in the next ten minutes, and then almost collectively it seems the class has finished. Another student collects the papers, a sweet boy with round cheeks who looks too good to be here. Before you have much chance to wonder about him, though, Ms. Lashes captures your attention once again. She has stopped flipping through the quizzes and is looking directly at you; her expression sends heat rushing up your collar even as you scramble to pinpoint anything you might have done wrong. Wait, no… no, she isn’t looking at you. She’s looking at whoever is behind you. She crooks a finger, and an incredulous voice says “What?!”


”Come here, please.”


”How do you know it was me?!” the voice exclaims again, and the girl sounds so shocked that you know without a doubt that it was her. No one innocent sounds that guilty before an accusation has even been made.


“I’m not going to ask again,” Ms. Lashes says sternly, and what turns out to be a pretty girl in a blue skirt lets out a dramatic sigh as she shuffles past you and to the front of the class. Ms. Lashes has taken a paddle from her drawer, and in short order the girl is bent over the desk and the paddle is cracking down on her backside. You aren’t even sure what she did, but you find out soon enough.


Ms. Lashes flips the student’s skirt up, and begins to scold as she paddles her. “There is no place in this school for vulgarity, especially in my class. I am un-amused with your answers and unimpressed with your lack of preparation.”


”Yes ma’am, sorry! Ow, sorry ma’am!”


That girl’s attitude changed in a hurry, and you can’t blame her. At least you didn’t have to show your underwear off to the whole class when you were spanked. She looks abashed when she is sent back to her seat, and you shift a little with sympathy pains. Still… better her than you.


Famous last words, you think when your name is called over the PA system in the middle of your next class. You actually try to negotiate with Mr. Rookwood– really, your time should be spent in class, not in the office! — but he asks if you want to explain to the principal that you were late because you had to stand in the corner for impertinence. You politely decline, grab your bag, and walk out the door. The hall seems more crowded than it should be, and you realize it’s because of the line trailing from Dean Kendrick’s door. You slow down, unable to curb your curiosity. The newest addition to the line is a girl sporting the most pitiful pout you have ever seen. She’s being scolded by another of the administrative assistants, who isn’t as impressed with the pout as you are. The girl is looking stubbornly away from the woman bending over her, and you take a moment to appreciate the contrast between the two.


The assistant’s black pencil skirt is form-fitting and professional, nothing like the girl’s plaid jumper and blouse. You blush a little, realizing that your own uniform doesn’t exactly make you look grown-up. At least you aren’t being scolded right now.

The bell rings, and suddenly the building is swarming again. You take your time, looking through the crowd until you spot the pouting student again. You can make out some of the words from the assistant’s lecture over the din of everyone changing classes; something about “not here to be social,” and being “awfully eager to see the dean of discipline.” The girl in the chair gets sulkier by the second. That last part actually makes you snort. Who would ever be eager to step foot in that office?


As if on cue, the unmistakable sound of a spanking begins, fast and rhythmic and echoing down the hall. Whatever hapless student is across the dean’s lap makes no attempt to be quiet, either, and a refrain of “please, please, stop, I’ll be good!” joins the swatting noises. You keep walking, embarrassed but so curious. You pass several other students who are siting outside of the office. You notice a boy fidgeting nervously, and a tall girl with a pretty bow in her hair sitting next to him. She has her legs crossed and one foot is bouncing; she’d look relaxed except for that bouncing foot. The student closest to the door is not sitting on her chair, but kneeling, bare bottom on display, and you are immediately embarrassed for her. As you pass the office, you glance in as discreetly as you can.


You mostly know what you will see, and still it comes as a shock. There is a boy in the corner with his hands behind his head and his pants pulled down; he’s clearly just been punished. Dean Kendrick has a student across her lap, and a bathbrush in her hand. A bathbrush. No wonder the girl being spanked is so loud! Her underwear are all the way down her knees, just above a jumble of cloth that could be pants or a skirt, you can’t tell. Her legs are kicking furiously, but the dean doesn’t seem to notice or doesn’t seem to care. She brings the round head of the brush down relentlessly; her other arm encircles the girl’s waist and seems to effortlessly hold her in place.


“Not a good place to be distracted.” The voice of a third assistant — you think each of the deans must have one — shakes you out of your open-mouthed stare. Heat immediately fills your cheeks. So much for a discreet glance. “Sorry, I…” you stammer, and then pause. You know this woman. This girl! She used to be a student here, but you didn’t recognize her at first. You didn’t really know her, but you knew of her. Everyone did! She was the reason schools like Cheeky existed! “What’s up, I’m...” you start, but she doesn’t let you finish.


“I’m not here to be your friend. I’m here to escort you to the Principal’s office, since you seem to have gotten distracted.


Your eyes widen and before you can help yourself, you say “Are you kidding me? You are like the mouthiest person who ever attended here!”


Her expression says, no, no she is not kidding at all. So does the firm grip she suddenly has on your ear. She releases you right outside the office door, and you glare at her reproachfully as you rub your ear. She looks at you sympathetically, but certainly not apologetically.


“I spent more time than I should have thinking funny was enough. I’m still funny, but now I’m so much more,” she says quietly. After a brief pause, she continues abruptly, “You need to learn how to be a smart-ass without being a dumb-ass. They are actually trying to help you, and you should let them.”


You’re shocked by her candor, but she leaves before you can reply. You don’t know what you would have said anyway. Your knee-jerk reaction is to downplay her words, write her off as some uppity graduate but…another part of you wonders if she’s right.


Whatever, you think, brushing it off. You don’t have time to psychoanalyze yourself right now. You realized that the office door is opening, and the principal’s assistant is suddenly there, clipboard in hand as she holds it open for you. You freeze, and she moves her head in an expression of disbelief. “What are you waiting for? Go in.”


You take a deep breath and do as she says, walking past her and into Principal Hayes’ office. There is already a student in here, just like in the dean of discipline’s office. This time it’s a girl, one you recognize from your second class. You’re immediately embarrassed that you do, since you recognize her from behind — and her behind is something to behold right now. Her underwear are up, but they don’t do much to hide a very obviously spanked behind, and they do absolutely nothing to hide her very obviously spanked thighs. You actually saw her get sent out of class; you remember her being so defiant about it. That was this morning though. This must be her second visit here. Ouch.


Principal Hayes is behind the desk, thumbing through a file folder. His fingers cover part of it, but you can make out enough letters to know that it’s your name on the tab. You feel sweat begin to form along your body; you instantly feel guilty and you genuinely don’t know why. What is in that folder?!


“Just a moment,” he says, glancing up and making brief eye contact before he is re-engrossed in whatever is contained in that file. You look around the office, hoping to distract yourself, but there is little that brings comfort. He has not one, but two hairbrushes on his desk. Two. And you bet neither one of them has every been used bristle-side down. After several more tense seconds, he closes the folder and stands. He walks past you, and you hear movement just outside of your periphery. He is fixing the skirt of the girl in the corner. He doesn’t try to conceal the conversation they’re having.


“Do you understand why you were in trouble today?”


“Yes, sir.” Her voice is small and nervous, nothing like the brash girl from this morning.


“And now where are you expected to go?”


“To…” She hesitates, and you have strain to hear her whisper, “to the dean’s office.”


“Exactly right. Skip the line.”


The next thing you hear is the door opening and shutting again, while you are trying to imagine taking another spanking on a bottom so swollen and obviously sore. You should probably stop worrying about her, though. Principal Hayes is walking back around, and he’s undone the cuff of one shirt sleeve and is rolling it up to his elbow. Your stomach flops. You want to tell him that you haven’t done anything, you swear, but the truth is you aren’t sure. You have a bad habit of making rash decisions and paying for it later. He reaches for one of the brushes, an oval one that looks incredibly…solid.


As he walks back around you, he begins to speak, so this time you turn your body and your eyes follow him. “I can only assume that you do not know why you are here. Is that correct?”

You nod.


He nods back. “This makes sense. It makes sense because a student as bright as you would certainly have remembered reading that all students who turn in their registration forms for Cheeky Prep late would be given a thorough hairbrush spanking when they arrived.”

Your eyes widen; you are incredulous as you blurt out “I don’t remember that!”


“I’m sure you don’t. I don’t believe you have, up until this point, been taking this program seriously. We forget the things we don’t take seriously. Your records indicate to me that you have ended up here precisely because you refuse to take things seriously. Your education. Your behavior. Your future.”


Your squirm under his gaze; he has crossed his arms so the brush dangles ominously beneath one of his elbows. He continues to lecture you.


“Now if I were you, and I had been sent to a reform school, I would have taken the threat of a hairbrush spanking seriously. And I would have sent my registration in on time. Come over here, please.”


For a moment you can’t move. Your mind is whirring with options. Can anyone get you out of this? No, anyone you could call would only lead to more trouble. Physical escape? No, he’s blocking the only exit. Fire alarm? Is there a fire alarm you can pull?!


“And if I were you, I wouldn’t make my principal wait any longer.” The sternness in his voice manages to loosen the grip of the floor on your feet, and you take the few steps over to him. That, and a small memory you wish you could bat away, the words on a form your best friend had shoved under your nose, and the way you had rolled your eyes at it…


He sits on the couch and seems to pull you over his lap in one smooth motion. You hear the brush clatter on the small coffee table in front of you, and he adjusts your body slightly. Then his hand is landing on your backside, and you understand at least one thing with perfect clarity: he is taking his part in this very seriously. Every single swat hurts.


About the time your feet start to kick involuntarily, he decides it’s time to spank with one less layer of protection. You still have your underwear, but they don’t seem to be doing any good. You wiggle here and there, and you can’t help the small noises that seem to leak out, especially when he concentrates on your sit-spots. Before too long, he pulls your underwear down, too, and you bury your face in the couch cushions.


He glides his hand gently over your sore bottom, assessing the state of things, you are sure. You hope to heaven that he’s going to deem you all spanked out, but you know this won’t be the case. You know it for sure when you feel him reach over and grab the hairbrush.

When he starts spanking you again, you almost immediately throw a hand back from pure shock. He snatches up your wrist and pins it to your back, never breaking his tempo. It burns and stings and just plain hurts! All of this over a registration form??


As if reading your thoughts, Principal Hayes begins to lecture you again as he spanks. A man of many talents, you think in spite of yourself, but it isn’t funny enough to distract from the bite of the hairbrush, or the bite of his words.


“This is, of course, not just about your registration. It is important — let me be clear about that. You are old enough to assume responsibility for such a simple task. But this is also about identifying a pattern of behaviors. This is about recognizing your ability to change some simple things about your life that will both help you grow as well as help you stop inconveniencing those around you. It is time to stop taking adults for granted, and become a responsible adult yourself.”


You are full-on kicking right now, unable to keep still over his lap and worried than in another minute you are going to fly right off of it. And about another minute later, you are almost right; luckily he stops spanking you and puts the brush down again. He releases your arm, and you tuck it under your head as you try to catch your breath. Principal Hayes rubs your back in a comforting way, and it does work, even though you can feel the heat radiating from his palm. You’ll understand if I don’t feel sorry for you, you think at him dryly. Your bottom throbs along with your heartbeat. You feel embarrassed and small and very very sorry. He made his point well — this really all could have been avoided. Facing your own poor judgment is painful, but now you have paid for it at least. Maybe and then some, you think with a wince.


He offers words of comfort, too, in his firm-but-reassuring way. “I expect better from you because I know you are capable of better. I expect I will see you again in this office at some point, but it better not be soon.” You squirm; the lack of judgement in his tone is somehow embarrassing, as if it is a given that you need spankings to behave yourself. You vow to yourself to prove him wrong. Which in another way, would prove him right, you guess.


You’ll have to think about that one later. For now, he is helping you re-dress and then giving you a hug and a few more words of advice and encouragement. You aren’t eager to face your classmates, yet again with a freshly spanked bottom, but then, aren’t you all in the same predicament? Cheeky Academy is nothing if not thorough. You grab your bag, wince at the half bend you have to do to pick it up. You walk to your next class, noticing some turnover in the line to the dean’s office. The door is closed now, but you hear someone in there squealing, wonder if it’s the girl from the corner, and move a little faster. This time, you slip into your chair gingerly, but still you flinch. It’s going to be a long afternoon.


If you enjoyed reading this vivid narrative, the Cheeky Staff highly recommends you visit this blog for more stories!

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