Dress Code Violation

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A pervy principal punishes a pretty pupil during detention.
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sissy11
sissy11
1,520 Followers

It was Friday afternoon and I was ready for the weekend. As a high school senior, my life isn't that hard, but I still think I deserve my well earned rest at the end of the week. This weekend was bound to be special, too, because me, my boyfriend Sam, and a few of our friends were going camping. I wasn't a prude and Sam and I had already had sex, so I was excited to see what would happen on this unsupervised trip.

The last bell rang and I rushed to my locker to get my things and go. Bending over, I was sure that my ass and panties were peeking out of my short skirt, but I didn't mind. I actually liked showing off and purposefully pulled my skirt up high when walking the halls. But it wasn't my fellow students I was trying to impress.

I attended a catholic all-girls school which meant the targets of my promiscuity weren't the student body, but rather the array of handsome men who taught and watched over us. For some reason my school had an all male staff. They thought it imperative to have men teach us how to be proper young ladies, which I didn't understand because all they did was make me horny! So with my ass out and panties likely showing I wasn't surprised when I heard a deep voice behind me.

"Ms. Baker! I hardly think that skirt length is in accordance with our dress code. Why, I can see your bum! What is a harlot doing walking my halls!"

I turned and saw Headmaster Dorn, the intimidating despot who ran our establishment. He was in his late 30s, a tall and burly man who could still somehow slink around, a panther hunting for the next pupil to berate when she got out of his very tightly drawn lines. He was a notorious disciplinarian and I'd heard haunting tales about long-lasting detentions in his office. He also seemed to have a predilection for girls who'd just turned 18 like myself.

"Headmaster, I'm so sorry!"

I shimmied my skirt down to get it to regulation length (which was a homely 1 inch above the knee) but Mr. Dorn stopped me before I could finish. He gripped my small arm.

"Ms. Baker, this isn't the first time you've had a dress code violation. If I'm correct, this is the third time this week I've had to chastise you for your licentiousness! What have you to say for yourself?"

"Headmaster Dorn I'm sorry! I didn't mean to, I promise! But please, can we talk about this later? I'm going on a trip with my friends and can't be late!"

"No, Kelly, we're going to talk about this now; I'm tired of telling you to stay modest. Frankly, I think you may be going down the wrong path. And what is this trip you're talking about? Are you even old enough to go somewhere without parental supervision?"

"Yes, Headmaster, I just turned 18 last month! And my boyfriend and I are going camping in just a few hours so please can I go?"

"Just turned 18 you said..."

It seemed Mr. Dorn had only heard the first part of my outburst. I tried to scurry away but he held me tighter.

"Kelly, I'm afraid you're going to have to come with me to my office. You are clearly experiencing some new feelings right now that you're expressing through your whorish dress, and I don't think I can let you go until we've discussed your behavior in detention. Come along, missy, you can text your little boyfriend and tell him you're going to be late. I won't keep you long."

I wanted to run but his body was twice my size and he easily led me to his door. When we got in he locked it which made my stomach drop. This didn't feel right.

"Ummm... Headmaster? Please can I go home now? I promise I'll be a good girl until graduation."

Mr. Dorn chuckled and led me over to his large oak desk. I felt a lecherous hand "accidentally" swipe the underside of my left buttock as he walked by and his creepy grin made me shudder. I usually thought our Headmaster was a really handsome guy, sort of a Daddy type, but now I could only see him as a perv who had caught his prey.

"Since you're in here because of you're insatiable need to show yourself off, I think the appropriate way to kick this naughty habit is to give you an outlet. Give you a chance to see if you really like teasing men."

"Headmaster!"

"Quiet, girl!"

He rushed up to me and put his hand over my mouth. I looked up in fear and he stared down at me sternly.

"No more talking, okay?" I nodded. "Good girl," he grazed my cheek tenderly.

"Why don't you start by hiking up that skirt, Kelly. Pull it up slowly and I'll tell you when I think it's the right height. Go on now, I know you love doing this."

He had a point. I slowly pulled the waist of my skirt up until the bottom was mid thigh, half of my smooth, tanned legs now exposed between my long socks. I looked up and Mr. Dorn shook his head. He pointed his finger up so I pulled the skirt higher until the bottom rested at quarter thigh. My legs were trembling because I had on one of my sluttiest white g-strings, which was sure to set Mr. Dorn off in some way or another.

I hoped this would be high enough but when I looked for confirmation he, of course, commanded me to raise my skirt even more! With a tear forming, I pulled it up until the swishing pleats were resting just above my cheeks, the bottoms of my plump globes poking out. My panties were thankfully covering my freshly-waxed, teenage pussy which was starting to feel funny next to this older man.

"That looks to be the right height, don't you think, Kelly? Now you get to show off those incredible legs just like you always want to."

"Umm.. yes Mr. Dorn, thank you..."

I'm not sure why I thanked him for his compliment, but with no power in the situation it felt like the right thing to do. I'd pretty much do anything at this point just to get out of here.

"You know, Kelly, it's not just legs that men like to see. No, we like much more than that. Why don't you undo the top button on your blouse, girl. I've seen you do it before, so I know it won't be our little slut's first time."

He read me again and seemed to know all about my habit of unbuttoning my shirt, especially around certain teachers I thought were hot. I'd tease my history and math teachers by sitting front row and pulling my skirt up. I'd spread my legs under the desk and unbutton once or twice to let my full breasts pop out. Young Mr. Stephens could hardly contain himself while teaching trigonometry.

"Another button, girl."

I'd now undone the top three and my matching white lace bra was showing. I noticed that Mr. Dorn had, too, begun to expose himself by taking off his tie and undoing the top of his shirt. His chest hair flowed out which made me bite my lip. To my embarrassment, I loved hairy men. My friends all thought they were gross and preferred the sleek, toned bodies of theirs and my stud teen boyfriends, but I secretly craved a hairy beast. The strict contrast of big, manly bodies against my smooth, curvy figure was a prominent fixture in my fantasies. And now it was happening in real life.

"So, you see why your outfit choices have been inappropriate lately, correct? You see just how much of a whore you look walking down my halls, begging the fine men of this institution to stumble and fall prey to your seduction. Do you think a girl like you ought to be allowed to do that without consequence? Do you think she can show herself off to red-blooded men without them taking advantage of her sweet, vulnerable body?"

He'd gotten up close and was almost holding me as he raged. His hands were firmly planted on my ass and I tried to squirm free but couldn't. I relented slightly and soon found myself wriggling, but in a different way. The big hands cupping my cheeks were squeezing and prying, his probing fingers getting closer to my pussy. Mr. Dorn was much bigger than my boyfriend and it was comforting to lean into him, his wide frame easily supporting my petite body. My panties were moistening and I snapped back to reality and jerked away. Mr. Dorn grabbed my wrist.

"Can I please go home now, Mr. Dorn!" He laughed.

"Did you really think that was all your punishment, little girl? You broke my rules and you are going to pay the price. This little strip tease was just for your benefit, with your voyeuristic tendencies and all."

My benefit! The perv just wanted to see some tits! He pulled me over to his desk and bent me up against it.

"Hold onto the side now, girl, I don't want you moving too much while I punish you."

Moving! What was he going to do?! My knuckles went white gripping the edge of the desk as Mr. Dorn came to the left of me. He lifted my skirt and inhaled sharply when he saw my naked ass. He was so close to me and I was tired of fighting him off so I just stood as his meaty hands groped my buns.

"Such a beautiful bum, Kelly. So fresh and pert. Just begging for a few wallops."

"Wallops???" I tried to jump back but he held both my wrists in one hand.

"Quiet! Certain girls with behavioral issues like yours need special attention to fix them. Since you've been so insolent as of late I've decided that the only way to straighten you out is give you a firm spanking with my bare hands."

His other hand was swatting the bottom of my cheeks upwards in anticipation, making them jiggle. All this touching around my butt and pussy got me warm and wet and I was terrified that Mr. Dorn would see my physical reaction. I tightened my legs to hide my dripping honey.

"Yes, girl, I'm going to give you a bare-bottom spanking and afterwards you're going to follow my rules to the letter, lest you want to spend more time over my desk. When I give you each spank I want you to think about what you've done, and think about why you're in this room. I also want you to think about why your little pussy is getting so wet for your Headmaster, Kelly."

I gasped at his statement and he smirked before gripping a cheek, shaking it, then slamming his hand down onto it.

"Ahhh!! Mr. Dorn!"

"Quiet, Kelly! I know what I'm doing. This isn't the first time I've had a slut in this position. Now I'm going to redden those cheeks until you respect my wishes!"

SMACK SMACK SMACK SMACK

He alternated left to right, still holding my wrists tightly. The spanks hurt but in between each he'd rest his hand and manipulate my bubble butt. His fingers would twiddle against my panties and every tap made me leak more until they were sopping. The spanking continued and Mr. Dorn leaned down to tell me something.

"From now on, Kelly, I'm giving you a new dress code. Since you want to act like a slut, you're not going to wear your skirt modestly like the other girls. No, I'm going to let you be the whore you obviously want to be. You're going to pull your skirt up high, nearly to the cheeks, showing all your male professors what they've been missing out on. You're going to unbutton a few times, too, and you're always going to be in matching panties and bras to make sure you look your best. Do you understand me, girl?"

The pain of the spanking and utter humiliation of the experience had set in and I cowed to the desk pathetically.

"Yes, Mr. Dorn I promise! I'll do what you say I swear! Please, please, please can I go home now!"

My legs were jelly and the desk was holding me up. Mr. Dorn walked behind me and pushed his crotch up against me, lewdly pumping it up against my butt. Between the desk and Mr. Dorn I wasn't going anywhere so I lay and let the bizarre pleasure of this huge man humping me take over. I may as well get something out of this, too. I felt myself lightly pushing back against the firm bulge in his suit pants. Unfortunately, my reciprocation came off as eager and he didn't like me trying to take charge.

"Little whore," he grumbled before yanking me back up off the desk.

With tears running and my disheveled skirt barely covering my reddened ass I tried to button up and run out but Mr. Dorn stopped me again.

"Uh, uh, uh, little girl. You've been very bad and I think it's time we give your mother a call."

"Stepmother!" I corrected him.

I hated my stepmother and I'm sure he knew that. Ever since she married Daddy she started taking all of his attention and left me to rot. Daddy was so enamored he went along with it, saying "ask your mother dear" and shooing away any complaints I had. "Mother" (I never called her that) was rude and thought I was getting in the way of her life with Daddy. She wanted me out of the house so he wouldn't spend time and money on me. She was a real bitch and I hated her.

"No don't call her! Please!"

"Silence! I'm going to tell her all about your little misdeeds. Come. Sit with me."

He sat in his throne-like desk chair and pulled me into his lap. I wrestled out for a second but he easily held me with an arm around my slim waist. I stopped fighting and put my two hands delicately on his hairy forearm that was exposed from his rolled up sleeve. He looked like such a man and all those naughty feelings came flooding back. Mr. Dorn picked up the phone and began dialing; he put it on speaker.

"Hello. Mrs. Baker speaking." I rolled my eyes. She loooved calling herself Mrs. Baker.

"Hello, Mrs. Baker. This is Headmaster Dorn from St. Peter's School for Girls."

"Oh! Mr. Dorn! For what do I have the pleasure of speaking to you?" I scoffed again. She was always obsequious to men in power.

Mr. Dorn moved his hands to my chest and began undoing my blouse. I gasped when he pulled it off but he just hushed me then moved onto the bra, unclipping it deftly from the back. He yanked that off, too, and I tried to cover up, but he scolded me quietly and replaced my hands with his. He was tweaking my pink nipples while he spoke.

"Unfortunately, Mrs. Baker, I have some bad news to relay. I've caught your daughter violating our dress code three times this week and had to take her into detention this afternoon."

"That little skank!" My stepmother broke her charming veneer. "What did she do this time? That girl is trouble, Mr. Dorn! Always doing the wrong thing, I tell you! I'm so sorry you had to take her in, I hope she didn't cause too much harm."

"No, no, Mrs. Baker, there's nothing to worry about. She's a fine young lady, just a bit... attention-seeking."

He moved one of his fingers from my nipples and put it over my panties. He slipped it under and began rubbing circles all around my clitoris. I held his veiny arm with both my hands while his assertive rubbing made me moan.

"What was that, Mr. Dorn?"

He muted the phone and admonished me.

"I said quiet, girl! Unless you want me to get you into more trouble with your stepmother and Father!" He covered my mouth with his non-molesting hand.

"So sorry about that, Mrs. Baker. But as I was saying, your daughter has been a habitual violator of our dress code, pulling her skirt up for all the good male staff at our school to see. I hate to tell you this, Mrs. Baker, but your 'innocent' daughter even wore a g-string to class today, and many of her professors reported that they thought she was trying to flash them. I'm so sorry I have to tell you this."

"WHAT!!" My stepmother exploded. "That SLUT!! When I tell her Father about this!"

One finger then two were slipping their way into my pussy and liquids flowed onto Mr. Dorn. Stuck on his hand, he moved me to the side to unzip his pants and free his cock. It poked out under my skirt and I saw it was much bigger and meaner looking that my boyfriends. My insides churned thinking about how well it would fill me up, just like his fingers. He placed both of my hands on his penis and it was so big I could barely wrap them around. I was in awe at how much larger it was than Sam's! It made me surprisingly horny. Maybe I am a slut...

"Yes, Mrs. Baker, it really was inappropriate of her. But there's nothing to worry about, I'm giving her a special detention right now to straighten her out and I'm sure your daughter will come home with the right mindset."

He was moving me back and forth over his cock, rubbing my wet cunt along it to soak it. He began tapping his rod lightly against my mound, then violently smacking it against me. I shook and writhed from the clitoral stimulation as he lifted me to dip his tip into my tight hole. The head breached.

"That whore isn't my daughter. Do what you want with her."

My stepmom ended the call abruptly and I looked back to see a grinning Mr. Dorn. Still holding me on the tip of his cock with my feet off the floor he said devilishly, "You heard her, girl, I can do what I want with you."

Slowly he lowered my body onto his cock, stretching my tight lips over his engorged mass. It was so much thicker than my boyfriend's and the decent felt much different. Painful, but strangely fulfilling. I pushed up against Mr. Dorn's thighs to break away but he held me by my waist and impaled me further.

"Oh! Mr. Dorn, please! It's so big! Please, please stop!"

"Why stop now, Kelly, you seem to be enjoying yourself."

He had one hand pinching my erect nipples and the other back on my clit. His circling fingers were relentless and the two-pronged approach blew everything my boyfriend did out of the water! The stimulation was overwhelming and I couldn't help but pant and gasp in Mr. Dorn's lap.

"Not used so something so big, huh? I bet that little boyfriend of yours isn't much of a man, is he, Kelly? I bet your little pussy doesn't get nearly this wet when he fucks it."

He sloshed his fingers through my lips to prove his point. It's true, I really don't get this wet with my boyfriend. Even though I didn't want Mr. Dorn to fuck me, I had to admit that he made my body feel so good. He made me feel weak and controlled, like he could do whatever he wanted with me, and something submissive inside me was yearning to please him. I wanted my boyfriend to do things like this: to take charge and fuck me when he wanted to, when I made him so turned on that he couldn't stop himself, but he just wasn't that kind of guy. Mr. Dorn obviously was, though.

"Oh! Oh! Oh!" I yelped in staccato as his cock drove deeper with each bounce.

"I won't make you admit it yet, Kelly, but I know you like this. I can see how your body is reacting and it's perfectly natural. You're just doing what any beautiful girl your age would do on a man like me's lap. You're spreading your legs and opening yourself for me. Such a good girl; feel me take you over."

He planted himself firmly to the hilt and I swore I could feel his cock brushing my cervix. He was SO much deeper than my boyfriend had ever been and his girth pushed my walls to their limit. He was right, though, it felt amazing. So much better than Sam's noodle. Mr. Dorn was pistoning in and out at such a rapid pace I knew my orgasm was coming. I held my hands on top of his and shut my eyes, ready to ride the wave, but suddenly he pulled out and held me over his cock.

"No, Mr. Dorn! Why!!"

I quickly covered my mouth. Shit! I practically just begged him to keep fucking me! I looked back and saw my satisfied Headmaster.

"I knew you liked it, you little slut. Admit it! Tell me! Tell me you like it and I'll put it back."

He lowered my pussy til it was just above his tip and rubbed it over my clit and lips. He dipped the tip in the hole, taunting me. But it just wasn't enough and I knew I needed more. I needed to be full again. I cried.

"Please Mr. Dorn..." I sniffled, "pleeeeaase, just put it back in me. I neeeeeed it..."

"There, there, Kelly, don't cry. I've got what you need. Daddy's got you."

I didn't like that he called himself Daddy but when he reinserted his penis I stopped caring. I was just happy he was back inside me. He lowered me back down and let me bounce happily again.

"Oh Mr. Dorn..." I breathed out dreamily after a particularly pleasing poke.

I lay my head back against his chest and closed my eyes. He hugged me tightly and leaned his head down to me. I opened my eyes and saw him watching me with a gentle smile. He placed his lips over mine and we kissed. First slowly, then more passionately, until I could feel microabrasions forming around my mouth from his scratchy beard. I didn't mind and kind of liked the feeling; even his face dominated mine! Everything about him just screams "I own you" and I can't help but accept it.

sissy11
sissy11
1,520 Followers
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