The Headmaster's Office

by

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Consensual, Heterosexual, Fiction, First, Oral Sex, Squirting, Size, Teacher/Student, .

Desc: Erotica Sex Story: It's hard to predict how your day will play out. For example, "No Panties Tuesday" started as a harmless school prank; I could never have predicted that by lunchtime I would be kneeling splay-legged on the headmaster's desk, his hand (innocently?) between my thighs just moments away from discovering my nakedness and arousal. And the day was only half over...

All characters appearing in this work are fictitious. Any resemblance to real persons, living or dead, is purely coincidental.

It's after midnight and I'm writing this by torchlight under the covers of my bed, holding an ice pack between my legs. I can't stop thinking about what happened after school today; hopefully writing this down will let me clear my mind and get some sleep. If anyone is reading, I don't expect you to believe it, but I swear every word is true.


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 2nd period when my teacher discretely 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 11 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 40kg (88lbs), my new 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 18. We had 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 AAAs 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. 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 am so tiny and the bigger dildos that the netballers like just hurt me. Still, I do like some length and I didn't think he was going to bottom out, 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 the full length of his cock over my clitoris, along my burning wet labia and leaving his knob 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 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.


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 6AA bra and returned to school – miraculously - an 8C. 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 returned to school for the new semester. It's February so 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 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's not the worst bit: sitting down gave me only two inches of 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 was getting some small amusement from it.

She said "Sorry Belinda, Mrs Bingham has gone home with the flu, 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.

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