The Headmaster's Office 01

Author's Note: All characters appearing in this work are over the age of 18 and are fictitious. Any resemblance to real persons, living or dead, is purely coincidental.

Chapter 1

I'm in my final year at a posh boarding school in Sydney. It's pretty cool in an old-world sort of way. As well as the normal business, science and humanities subjects, they include other electives that would be more at home in a Swiss finishing school, like deportment and etiquette. It's supposed to prepare us to be tomorrow's leaders of society; you'll never get the CEO's job if you serve him from the right instead of the left at a dinner party, or worse, you stand talking to his wife for half an hour with your slip showing. Hey, maybe there's something to it; I know I could stand to be a bit more lady-like. Most of the time it's pretty fun, but the teachers can be strict. Where other schools punish students for drugs and alcohol, our big problems are inappropriate language and bad posture.

The trouble started this morning at the end of second period when my teacher discreetly passed me a note as I walked out. Yellow card: bad news -- "Please report to the Headmistress at lunch bell." I knew what this was about: for academic problems, you see the Headmaster and disciplinary issues go to the school marshal, so I knew it wasn't either of those. "Headmistress" is technically an Assistant Principal; it's an honorary title that dates back to the last century when the school formed as a merger of an all-boys and an all-girls school. The headmaster is the boss of the combined school, so the Headmistress is reduced to perform one job that he can't handle: girls' uniform violations.

Let's get this straight up-front: my summer school dress is a little bit short. I finished growing at age eleven and now stand a petite 4'11'' and three-quarters. The Asian girls like to hang around me because it makes them look tall, but with my milky skin and blonde hair I stand out starkly against their tan skin and dark hair.

At just forty kilograms (88lbs), my size XS summer school dress was new last year and I expected it to be my last before I left school. I had no boobs to speak of, so in a desperate attempt to get boys to notice me, I took up the hem to a racy mid-thigh level.

It worked ... kind of. I dated a boy named Brad for more than a month shortly after I turned eighteen. We'd progressed from holding hands and stolen kisses to heavy petting and one awkward episode of dry humping. He left a note in my locker to sneak out of the senior girls' dorm after lights-out. I could guess what that meant and to tell the truth I was equal parts excited and apprehensive.

~~~

Technically, I wasn't a virgin any more: girls' boarding houses have the highest density of vibrators and dildos in the known universe. They get handed down through the years and just seem to accumulate. I lost my maidenhead to a short, slim, gold vibrator named Ernest. It is at least 30 years old and has an on-off switch instead of a touch-sensitive button. Ernest takes tiny little watch-batteries which have long since died and never been replaced; the newer vibes take triple-As and are much cheaper to run, so nobody has ever tried to buy him a new battery. Ernest is given to all of the new girls; he's small and harmless -- well, relatively harmless -- but excellent for beginners because he makes you learn technique rather than relying on vibration or size.

I was excited to try sex with a real boy so out I snuck at the designated hour. Brad and I pashed and petted in the garden behind the gym for a while until we were both well and truly stiff with anticipation. He didn't seem prepared to make the next move so I drew up my courage and took matters into my own hands ... literally! I was underneath so I raised my hips and with one hand pulled down my soaking cotton panties, and with the other I released his throbbing rod from the straining confines of his underpants.

I couldn't see his dick but it felt wonderful in my inexperienced hand, a bit thicker and longer than Ernest of course, about 6" and a nice handful around the girth. I was relieved that he wasn't too thick; I'm so tiny and the bigger dildos that the netballers like just hurt me. Still, I do enjoy a bit of length, and sadly I didn't think my cup would runneth over, but beggars can't be choosers so I shouldn't complain.

He raised himself up over me to make space and I started stroking his iron tool against my flat belly and down to the wispy blonde curls of my mons. I rubbed his cock back and forth against my skin and with each back-stroke moved it closer to my glistening labia. Finally, one downstroke brought the base of his dick into contact with my clit. Involuntarily, I arched my back and pushed down with my hand, ploughing his full length over my clitoris and along my burning wet labia, leaving his cock-head poised at my entrance.

It was too much for both of us. I gasped and tipped over the edge, shuddering as the orgasm washed over my body. His dick bucked in my hand and sprayed cum over my thighs. I was soaked, sticky and spent, but deeply unsatisfied. I wanted cock.

He was mortified. I don't think he knew I had come and he probably thought he had blown it all by himself (well, in one way, he had). He zipped up, apologised, and raced away; and that was the end of Brad. For my part, the experience had spoiled boys for me. I was determined that my "real" first time would be with a man who knew how to handle himself, and meanwhile I was going to practice controlling my own body to reward his skill.

Chapter 2

At the end of last year, I packed up all of my books and clothes in the boarding house store room and went home to Melbourne for Christmas. To my eternal gratitude, Santa brought me the present I had dreamed of for the last 6 years: boobs! I don't know whether it was something in the water or just a last gasp of puberty, but in November I went home wearing a 32AA bra and returned to school -- miraculously -- a 34C. Now C-cup might not sound like a heck of a lot, but on my tiny body, they look like double-Ds. I love them, and judging by the looks in class this year, I'm not the only one.

The fairy-tale turned into comedy last week when I unpacked my summer dress from storage. There's an expanding panel at the back of the dress, so I could still button it up ... just; the buttons gaped a little at the front when I breathed in. But the real problem was the length; my new rack just took more fabric to cover and it caused the hem to ride two inches higher on my thighs. My over-locked hemline (oh why didn't I just fold it under!) was now covering my panties by a meagre five inches. But that wasn't the worst bit: sitting down gave me only two inches of panty-coverage.

The other girls in the senior dorm enjoyed the joke and had fun teasing me in a good-natured way. Unfortunately, none were good-natured enough to loan me a dress until I could get the money from Mum for a new one. Last night we played Truth or Dare and my best friend Trish dared me to go the whole day at school 'commando'. That brings us to today: "No-Panties-Tuesday."

The uniform shop will be open tomorrow and Mum came through with a money transfer on the weekend, so I just had to make it through this one day in the tiny dress with my pussy a few inches from exposure and then the nightmare would be over.

Apart from all the giggling in the back of class, it wasn't actually that difficult to get through the day sans panties -- I just kept my laptop bag on my lap (where else!) giving me a new artificial hemline all the way to my knees. Easy-peasey.

The yellow-card summons to see the Headmistress was a bump in the road, but it was just going to be about the hem and maybe the bust, not the panties (that would be a red card). Everything would be fixed tomorrow so I wasn't really worried. I couldn't get back into the dorm for panties until after school, so when the lunch bell rang I walked off to the heads' office suite casually holding my hem flat in case of a wind gust.

I handed the yellow card to the receptionist and she looked back up at me -- and my dress -- with a little smirk. She guessed what this was about too, and she was getting some small amusement from it.

"Sorry Belinda, Mrs Bingham has gone home with the flu," she smiled, knowing this would come as good news. "Can you come back tomorrow?" Even better! Tomorrow I would come back in a nice, modest school dress and she would send me away without a word.

A deep voice from the next office, "Send her in, Miss Strachan. I can deal with this."

Oh shit, the headmaster. I made silent, goggle-eyes at the receptionist and waved my hands in a warding-off gesture.

"But Mr Gallows, I don't think ..." she began.

"Nonsense! I'm not busy and Mrs Bingham could be home all week. Send her in."

She gave me a pitying smile. "Yes sir. In you go, Belinda."

I could get through this. Deep breath ... crap, button nearly popped! In I went.

Chapter 3 (Mf/Upskirt/Fingering)

Mr Gallows is really tall, about 6'4'', reed slender and kind of cute for an old guy (he's at least thirty-five!). He has a rugged outdoorsy look: short and wavy dark-brown hair, deep tan and beard stubble, but with straight white teeth and dimples that look a bit sexy when he smiles. He might have escaped notice from the girls except for one curious habit: whenever he thought that no one was watching he would reach down and adjust himself from the right to the left or back again. This is an endless source of amusement for teenage girls. We watch with mirrors when he stands at the back of assembly; we take bets on how many times he does it before the bell. Geez dude, go buy some comfy shorts.

There's no shortage of giggling and after-hours dreaming in the dorm about what he might be packing, and without fail it always ends with a wild rendition of a Led Zepplin's "Hangman", with a dozen teenage girls in nighties with air-guitars and hairbrush microphones, screaming like Robert Plant "Swingin' on the Gallows Pole, Swingin' on the Gallows Pole" and collapsing in gales of laughter. Sometimes I go back to my bed with Silver (after Long John, not the colour) -- an eighteen inch double-ended dildo -- still singing "Hangman" to myself and thinking about him.

"Shut the door, Belinda, shut the door." The two heads shared an office and he was bent over Mrs Bingham's desk searching for the counter-part of my yellow note that would tell him what he had so rashly volunteered to deal with.

He found it, held it up, and started reading to himself. He still hadn't looked up to see me yet, otherwise he probably could have saved some reading. "Aaaah ... right ... uh-huh ... I see," he mumbled as he read and then looked up, paused, and blinked a couple of times as his eyes wandered over the contours of my dress.

He cleared his throat after a pause that was a moment too long, "Won't you sit down, Belinda?"

"Actually, I'm comfortable standing thank you Sir."

"Yes, I see ... ah ... I mean, very well," he stammered. He steeled himself visibly, drawing up his enormous height and putting on the stern Headmaster-face. "Now it seems that one of our teaching staff has noticed that your dress is perhaps not in full accord with the school regulations," he announced formally in an ominous tone.

"Yes Sir, but I ..." I began.

"Now I normally step out while Mrs Bingham deals with these cases," he interrupted, "but I know the drill and I think we can probably sort this out without her help, don't you agree?"

"But tomorrow, Sir ..." I was starting to worry and tugging at my front hem to make it look longer in grim hope that this wasn't going where I feared it would go.

He pressed on without listening. "Regulations are very clear, Belinda. Your hem line must be no more than four inches above the knee, measured from the floor at a kneel."

My dress was higher than that even before the booby-fairy visited me. Now it was a subject way beyond doubt, but as he was saying it he reached back to his desk for a ruler. This was not looking good; both my hands were now frantically tugging at my hem and pulling my dress even tighter over my breasts. I couldn't utter a sound.

He came closer, towering over me with my head at the level of his elbow. "Please kneel on the carpet, Belinda, and we'll take a measurement."

How was this going to work?! If I kneel down one leg at a time, the dress rides up and flashes my panties-less pussy. I paused for a moment, thinking. Carefully, I bent both knees at once -- lowering myself slowly and keeping my hips straight to stop the cursed dress riding up. I got about half way down before the strain of the awkward position broke and I plopped forward onto my knees, hips in and back straight like a gymnast finishing a vault. Unfortunately, that's where the comparison ended as I toppled forward with the momentum of the fall.

The only thing in front of me was Mr Gallows' leg and I instinctively put out a hand to stop the fall. I got him open-handed on the upper thigh and as I pushed back to right myself, I felt the flesh beneath his suit pulse and heave beneath my fingers.

Oh. My. God.

I just grabbed the Headmaster's cock. And it was halfway down his pants leg. This guy must be hung like a horse!

He leaped back like he'd been stung by a bee; he looked down at himself, then hurriedly turned around and retreated behind his desk with the chair pulled in tight.

In a moment, he recovered serenely. "Perhaps over here would be better," beckoning to the space beside him. But then realising he wouldn't be able to reach me without pulling out from the desk and exposing what I now imagined must be a boner the size of a riding crop, he changed tack and cleared the leather-topped desk in front of him.

With colour rising in his face, he gestured to the desk. "Up here, please Belinda."

This was not going well. I still had tingles from the fleeting feel of his manhood in my hand. I was starting to get moist as I awkwardly stood up, and I could feel the lips of my vagina sliding deliciously against each other, making me wetter still.

Mr Gallows respectfully looked away to study a painting on the wall, and I nimbly hopped up onto the desk on my knees. The desk was antique and unfashionably low, so even with him seated I was now only a head taller. My breathing had quickened, straining the buttons open a little over my bust, and my rock hard nipples now pressed though my bra against the taut fabric. Right in his eye line!

He turned his head back around -- copping an eyeful -- and I saw him visibly reel back and flush. He should have called an end to this charade long ago, but now it was a matter of pride and authority, so he gamely pressed on, taking up his ruler.

He stood the twelve-inch ruler on the desk in front of me and I swear the top of it barely made it up to my hemline. I quickly moved my knees apart a little to bring the hem closer to the desk, but I was still easily double the regulation four inches. And now -- how did this happen? -- I was kneeling splay-legged with barely a thin sheath of cotton separating my dripping, bare vagina from the face of a guy whose enormous cock I had just groped through his suit pants. This could not be happening.

Disbelief became denial. I knew the rear hem was a bit lower because my new, improved C-cups -- now standing proud like cherries on big scoops of ice cream -- had only really caused the front to ride up.

"But Sir," I blurted. "Mrs Bingham measures the rear hem." I have no idea where I was going with this; I could hardly duck-walk around on my knees and anyway, there is no way the rear hem was anything like four inches from the desk. Not that I even cared! I was getting a new dress tomorrow!

Before I could work out how to back-pedal this desperate ploy, he reached around and stood the ruler behind my butt, then realising he couldn't see it from his higher angle, he scootched down and -- incredibly -- reached between my open thighs to swap hands on the ruler.

His face was now just inches from my aching crotch, surely he could smell me, but maybe he had a touch of Mrs Bingham's flu. He twisted his wrist a little to get a better look at the ruler, which amazingly he was still watching, bringing his cuff link into contact with my throbbing twat. The cuff link was cold and my engorged lips felt like they could melt it to scrap in a few seconds. I let out a tiny moan of pleasure and he quickly startled from his study of the ruler, dropping it and withdrawing his hand, sliding that wonderful cuff link through my open slit and making me shiver with pleasure.

He looked up at me, my eyes almost closed and biting my lower lip. Then he looked down at his hand, the cuff now dark and moist from my juices. He paused in a silence that seemed to stretch out forever, and then he sniffed it, confirming perhaps his darkest fears.

Very quietly, "Belinda, do you see any way that either of us can escape this moment and retain any dignity?"

"No sir," I whispered, my heart pounding. "I don't think so. Except ..."

"Except?" He looked up from the shameful pussy-stain, a look of hope in his eyes that there might be a way out of this where he gets to keep his job.

"Except, sir," I gulped. "I feel that ... I feel very strongly that you should finish ... you know ... what you started."

He stared at me for a good ten seconds, but I held his gaze, trying to tell him telepathically what I wanted.

Gaining composure, he slowly reached between my thighs again. "Like I was saying, I'm fairly sure, Belinda, that this dress is in violation of our school regulations." He picked up the ruler and tapped it lightly against my bottom setting off more shivers of pleasure. "But I'm not absolutely certain. Shall I measure again?"

"Yes please, Sir" I whispered.

"Very well." And then, with infinite gentleness, he raised his hand higher. This time the knuckle of his thumb nestled in the pleasure centre between my thighs. He added some light pressure, opening me up even further. "Yes, I can see the problem now. My thumb was in the way of the ruler and blocked my view. Shall I move it out of the way?"

"Yes, yes."

He straightened his thumb and positioned the tip at my dripping entrance. Then slowly, gently, and in one continuous movement he pushed into me. The pleasure was excruciating. Stroking his thumb in and out, he picked up an increasing rhythm and said, "Belinda, you realise that Miss Strachan is still in the outer office."

"Yes, Sir" I was starting to build up to a climax, which he was telling me had to be silent.

"I want you to do something for me."

"Anything," I whispered.

"There are a great many things to learn about becoming a woman that even this school does not teach in the syllabus. Even so, I am very well versed and would be pleased to tutor you. Would you like that?"

My eyes were now squeezed tightly shut as he increased the pace and pressure of my very first thumb-fuck. "Oh, God yes," I whispered. I was seconds away.

"Excellent. Please come see me here after school for your first -- no, your second lesson," he said. "Please don't feel you must return to the dorm to get changed; you can come just the way you are." As he said this last sentence, he thrust his thumb deeply in to the last joint and pushed back against my G-spot, using his giant open hand to grasp my inner thigh for leverage. My orgasm exploded outwards from my G-spot and I was coming like an out-of-control freight train. I bucked my hips against him but he held me with the one hand on my thigh and the other pressed against my belly. Biting my lip harder to avoid crying out, explosions racked my tiny body as I writhed in his powerful grasp.