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Yes Sir

Tags: finger, cum
Getting the punishment I deserve
I sat on the cold wooden bench outside Mr. Anderson's office trying to control myself. I was shivering uncontrollably, not from the cold or because I was afraid of the punishment I was about to receive. I was shivering because I was so aroused at the thought of what I was about to do. I certainly fit the profile of a troubled teen but I wasn't one.

I was the unwanted child of a teenage mother, who had worked as a nurse at the local orphanage, which I now referred to as the town's "lost and found". Only she knew who my father was. When news spread throughout the community of her unplanned pregnancy she made a public declaration that she would raise me take responsibility for her actions. As was expected, two days after my birth she left me in an office with a letter.

Granny, as she was affectionately known, was the senior doctor at the orphanage who adopted me as her own. Granny was the matriarch of our affluent farming community and now eighteen years later she was the director of the orphanage and worked as a secretary at St Augustine's College, the prestigious private boarding school that I had attended.

An unknown benefactor paid my school and boarding fees as soon as I was old enough to enroll. Everyone assumed the mysterious benefactor must be my father. He called himself Montgomery Burns much to our excitement, until we realized there was no record of the name and were later informed that "Montgomery Burns" was in fact the full name of Mr Burns of the TV show "The Simpson's."

I was startled when Granny stopped typing and spoke to me as if from within my own thoughts. "You may go in now dear." She said without looking up, obviously not pleased that I had been sent to Mr. Anderson for the second time in 6 weeks. My legs did not seem to want to move, as I stood walked down the corridor to the door with the gold plaque that read "Principal".

I entered quietly. Mr. Anderson was sitting on the edge of his desk, his right leg crossed over the other, filing his thumbnail. It was not quite the whip-cracking, pistol-shooting, whore-fucking behavior the sheriff Anderson on my fantasies exhibited. I didn't know much about Mr. Anderson other than that he spoke with authority and commanded respect.

I assumed he was in his mid thirties; he was too old to be my big brother and yet not quite old enough to be my father. He was a little taller than average with dark brown hair and the kind of muscles one earned only through an honest hard days work. He taught the boys carpentry and coached the school's first team rugby side, which were ranked 3rd in the country. I always woke up early and stayed late into the afternoons, to watch him run around in his shorts, his hot breath like steam in the cold morning air. He must think I have a crush on one of the boys, and so too did some of the boys think I was there to watch them. I straightened those boys out by explaining simply that just because a stallion is a magnificent animal does not mean I want to ride one. In truth it was not a young stallion that I was after, but the more elusive, unpredictable old bull.

"Please sit," Mr. Anderson commanded, glancing at me for the first time as he rounding his desk and sat down.

I did as I was told and sat on the edge of the bulbous brown leather couch. I pulled my pleated tweed skirt taught across the tops of my thighs and opened my legs just wide enough that if he cared to look he would see my cotton panties. I sat up straight and arched my back pressing my nipples against the flimsy white fabric of my school shirt. My shiny black hair was tied in a ponytail in accordance with the school's dress code. I wanted to yank it free and toss it around before letting it tumble down to my breasts, like they do in shampoo ads on TV.

He started the speech that he had obviously prepared but I wasn't listening. I instead watched him and tried to figure out where he was looking. As he rambled on about attitudes and responsibilities I noticed he was slowly leaning back further and further, almost slouching, which was unusual for a man as disciplined as Mr. Anderson.

I spread my legs a little wider and almost immediately he sat up and changed his tone. "You know why you're here, and yet I don't. You're a beautiful, smart young lady..."

My heart skipped a beat and I felt the embarrassing heat rising in my cheeks as I blushed. I knew I was popular with the boys my age, that would do anything to squeeze a tit, but I'd never guessed that a man of Mr. Anderson's stature and experience would consider me beautiful. He also right about me being smart. I was first in every class I'd ever been in all whilst captaining the 1st Hockey team since grade 10.

I also dabble in gymnastic but just for fun, and to watch the boys blatantly gawk at my supple body. I pawn the medals I win for cash.

Mr. Anderson had stopped talking. I looked up at him in time to see his eyes glimmer with intent. "You know what to do," He said sternly.

"Yes sir," I replied almost too enthusiastically.

That was my cue. I was supposed to stand and place my hands flat on his desk where he would then slap my knuckles with his cane. That however is not what I did. I took my punishment like one of the boys, not as an act of rebellion but because it was what I wanted, what I craved. Since he hadn't stopped me last time, I stood and walked around to the back of the couch while he snapped open the ornate ivory case that he kept his cane in. I stood with my hips against the back of the couch, only this time, I hooked my thumbs into the delicate ribbon and lace waistband of my sheer baby blue cotton panties and slid them halfway down my thighs. I then bent forwards, flipped my skirt up over my arched back and with my head resting on the seat of the couch presented my toned, supple eighteen-year-old bottom to the sky.

Mr. Anderson stood watching, mindlessly stroking his cane. My mouth was open and my breathing was fast and heavy. My mind swirled with arousal and I imagined David Attenbourgh behind a pot plant in the corner of the room describing my behavior.

"This fertile young female is obviously in heat as she assumes a submissive posture and presents her genitalia in the hopes that the Alpha male will stuff her full of cock"

Maybe not that last part. My whole body was trembling and I could feel the warmth in and around my pussy. I can only imagine the sight that greeted Mr. Anderson as he positioned himself to administer his first strike. I keep the soft back hairs of my bush neatly trimmed but had shaved my labia bald especially for the occasion. Thwack!

I felt the sting instantly and my eyes began to water. Mr. Anderson wasn't holding back Thwack!

He timed his strokes with precision, so that just when the pain began to fade the next one hit. Thwack!

I would have regretted my decision if the numb throbbing had not begun to kick in. Thwack!

The pleasure was now starting to out weigh the pain as I felt the familiar aching build-up in my abdomen. All I needed was one more to send me over the edge. Thwack!

It wasn't immediate but it was coming, I was Cumming. By now my pussy was pouting and my wet pink flesh dribbled pussy juice like a ripe fruit. I wished I could reach back and rub my clit. My pussy squelched as it throbbed, my orgasm radiating through me in hot waves of pleasure. If I hadn't been so aroused I might have been self-conscious about the milky secretions trickling out of my hole, running down my lips and dripping off my clit into my panties.

"Are you all right?" Mr. Anderson asked his voice softening.

A breathy "Yes" was all I could muster.

Mr. Anderson gently placed his hand on my still trembling ass cheek and stroked it, careful not to touch the still sensitive red welts that striped my ass. The rough skin of his palm barely made contact with the soft smooth skin of my bottom. He paused for a moment and then pressed his hand firmly into my flesh, squeezing it as he spread my cheeks apart so that he could get a better look at my wet gaping entrance.

I pressed my ass back into his hand, affirming his actions. He released his grip and I feared that I might have acted too soon. I dreaded the thought of him telling me to tidy myself and leave. I waited for a moment, and was rewarded with the slightest touch between my drenched hole and my anus, which twitched in response.

It was a finger, as I hadn't heard a belt buckle or zip.

He placed his left hand on the small of my back and slid it under my shirt and up my spine. When he reached the back of my neck he stopped and squeezed gently as if choking me from behind, before sliding his hand back the way it came.

Meanwhile his finger meandered along my slick sticky slit.

I could guess now that it was his thumb, the one he'd been filing earlier. I wanted it in me, but he continued to tease me, sliding it up, down and around the length of my opening. His left hand returned to stroke the hair away from my face.

"All you aright?" He repeated, now looking me in the eyes.

"Yes Sir" I replied. My burning blue eyes begged him more than any words could.

He tucked the hair behind my ear and then grasped my ponytail and pulled firmly enough for me to understand. I lifted my upper body off the couch, and with my hands on the edge of the couch supported my self with my arms. He adjusted his grip and pulled my head back forcing me to arch my back. Then he slowly pressed his fat digit into my slippery folds.

He pressed so slowly that his thumb felt as though it was the size of a coke bottle. As he pressed deeper and deeper my pussy clenched repeatedly squeezing his thumb tighter every time. When he could go no deeper he cupped the rest of my pussy with his hand and with his palm rubbed my exposed clit.

It wouldn't take long now, I pressed myself back onto him wanting him to fuck me with his thumb, but instead he just held it inside me. Then as slowly as he had begun he started to slip his thumb back out and without warning jammed it back in to the hilt. It sent shockwaves down my legs and up my spine.

My head would have flopped forward if Mr. Anderson wasn't gripping my ponytail like a bitch in a bar fight. He pressed down hard on the spot Dr. Grafenberg had found and began manhandling my pussy. He rocked his thumb vigorously in and out of my eager hole, rubbing the pad of his thumb firmly against the spongy ridge inside my vagina, while his fingers slid back and forth over my clit. I rocked my hips back and forth to meet his hand. I could feel the wonderfully uncomfortable pressure aching in my abdomen again.

"I'm Cumming!" I gasped, not sure why I had said it or to whom.

I held my breath, my back tensed and my face flushed pink as my body began to quiver. I thrust my pussy back and was almost standing up straight with my legs slightly bent trying to get as much of Mr. Anderson into me as possible. Not knowing what to do with my now free hands I grabbed frantically at my heaving breasts in search of a nipple to pinch.

Mr. Anderson refused to release the fistful of my hair in his left hand. If my eyes hadn't been closed I would have been looking right at the antique ceiling fan. My pussy contracted violently on Mr. Andersons thick thumb as he continued to rub my flooding insides. I could hear my pussy spluttering as it squeezed his manly poker. And then I came all over his hand; pussy juice streamed out of my gaping pink hole and ran down my legs stopping only briefly at my panties before continuing to the wooden floor.

Mr. Anderson finally released his grip on my hair and removed his thumb from my twitching slit. My milky ejaculate dribbled down my legs following the same path my pussy juice had taken. He stood behind me now, wrapped his arms around my waist and pressed himself close against me. I could feel the bulge in his pants just above my still exposed ass.

I suddenly became aware of my hands; the left was still grasping Mr. Anderson's firm ass, the other had released and was still clasping my left breast, with a swollen red nipple between the index and middle fingers. As casually as possible I relocated my hands and wrapped them over Mr. Andersons. His thumb was still moist when I interlocked my fingers with his. I rested my head back against his chest and looked out the window, it was starting to get dark. It felt like he held me like that for hours but it was probably just a minute or two.

Mr. Anderson lifted his chin, which he had been resting on my head and I turned to face him. Again he gathered the hair away from my eyes, tucked it behind my ears and then held my face in his hands. "Are you OK?" He asked, now smiling warmly.

"Yes Sir" I purred, now more comfortable with him than I'd ever been with anyone in my life.

"You'd better head back to your dorm," He said before reaching down and sliding my damp panties back up to my hips.

My skirt was bunched up around my waist, and so he tugged it down and rearranged it while I adjusted my bra and did up the buttons that had some how come undone. I tucked in my shirt and then let my hair down, and tossed it around trying to be as sexy as possible without being too obvious. I then gathered it into a neater ponytail than the one it was in when I arrived.

Mr. Anderson stood staring at me, and then as if waking himself from a daydream said, "I think it would be best, if you were to visit me on a regular basis from now on. Perhaps once a month, just to make sure that you don't slip back into trouble again!"

I nodded.

"And call me...Mr. Anderson," he added.

He took a step back and with a swing of his arm, motioned towards the door.

I adjusted my skirt once more, smiled at Mr. Anderson and opened the door, relieved that I wouldn't have to think up another scheme to get myself sent here again.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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