The Headmaster's Indiscretion Pt. 01

Day One -- Journal entry

Starting my new undercover assignment today. This one is going to be interesting, I expect. I will be posing as a 18 year old girl at Miss Priscilla's Boarding School. The chief says there have been some disappearances of girls from there and although the girls show up eventually, claiming to have run away...he thinks there is something fishy going on.

Good thing I look young for my age: 25 going on 18-- talk about a step backwards! My 'parents' are supposed to be dropping me off there today, bag and baggage. It was fun shopping for a teen-ager again although I wouldn't wear half the stuff normally!

Quite the outfits the girls have to wear: black-watch: tartan skirts, white blouses with peter pan collars, black knee socks, penny loafers and black blazers - always buttoned! Least that will hide my undies. No way am I giving up wearing my colourful satin flowered and matching undies for plain white cotton (to the waist) underpants and white, heavy (designed for aged matrons) bras!

For years, I have been trying to dress older, (sigh) Back to ponytails (yes, according to the 'Miss Priscilla's Book of Rules', 'if a young lady's hair is longer than shoulder-length, during the day it must be restrained in a ponytail up high on the back of the head worn with the school ribbon tied in a neat bow. Short hair should be worn with the school headband holding the hair back from the face.') Since my hair is long, down to my hips, it will be a long ponytail! At least I don't have to cut my hair or dye it like I did for the last assignment. Hated it black. I love the silvery gilt colour it is and it curls just enough. Restrained--hah! My hair doesn't know the meaning of the word...come to think of it, neither do I!

Not much point in packing a lot of make-up, Miss Priscilla's young ladies aren't allowed to wear make-up. Well, I'll keep it down to mascara, blush and some lip gloss: a girl can't run around naked!

Star

I arrive at the school in my 'parent's' limo and am dropped off. The Head Mistress, Miss Pringle, invites (commands is more like it) me into her office. I am introduced to my prospective roommate, Jennifer. She is a dowdy girl, with lank hair (pony-tailed, of course) and a sour look upon her face. She is dismissed to carry my luggage up to our fourth floor room and then I am introduced to Madame La Farge (French), Madame Pratt (maths), Madame Schuck, (science) and they all stare at me as if I were under their beady-eyed microscope.

I am told to report to breakfast at 6:30 am sharp and released to go find my room. Miss Pringle also said I'd meet the rest of my teachers and the Headmaster at dinner in half an hour. Finding my room, I surprise Jennifer nosing around my luggage.

"You sure have a lot of stuff! What's your name again? Stephanie? How long are you stuck here for? What did you do that your folks sent you here? I'm 18, how old are you? Are you a virgin? Where do you think you'll wear all those clothes?"

Her string of non-stop questions was driving me crazy! This was not going to be fun! I tell her that yes, my name's Stephanie and that I just brought everything because you never know what you might need and that it was none of her business whether I was a virgin or not! (I'm not, but, hey, I'm not really 18 either!)

We head down to din-din. Big fancy dining room with round cherry wood tables set for eight with linens and stem ware. I stand behind a chair, next to Jennifer and wait like the rest of the girls. It seems like there are a hundred in all although there are a few empty chairs when we sit down.

Mental note: one probably belongs to Tina, the girl who recently has 'run away' from the school.

At the head table, I see a few new faces and the girls at the table don't hesitate to fill me in! Talking in low voices, 'a lady always talks in soft, modulated tones' (blasted rule book again) they tell me to watch out for Headmaster Thaddeus Macleod. He is very strict and one didn't EVER want to be called to his office! The girls said he was called 'Cropper' behind his back because he always carries a riding crop even though he's never been near a horse close as they can figure! He wouldn't hesitate to slam it down on your desk if you weren't paying attention in class. I asked what subjects he taught and they told me English and History.

Damn, my two worst subjects. The things I do for the agency!

The Headmaster strides in. He is tall, perhaps thirty or thirty-five, dark haired (cut long and brushing his shoulders-- where's HIS headband, or for that matter, his pony tail!), slim to the point of emaciation and sports an impeccably fashioned goatee.

Dinner is served on fine china, (I know where part of the hefty tuition goes!) but dinner is tasteless, over-salted and generally disgusting. Well, I wanted to lose a few pounds anyway. The girls at my table all seem nice, in general agreement that they don't really like it here and then the discussion moves to Tina and how they doubt she ran away.

"She's such a mouse!"

"Timid."

"Good grades, does her work on time."

"Was called to the Headmaster's office a few times for failing to identify an author of a quoted piece though'."

"What's that about?" I asked. The girls tell me it is his favorite thing to do: quote a piece from literature and ask someone to identify the work and author. Shit, I'm in for it now! I grimace and one of the girls, Gladys, I think, tells me that she hopes I'm up on my authors because as the new girl, he's sure to pick on me a lot! Double shit!

Dinner, finally being finished, something that I think was supposed to be tapioca (ugh) for dessert, we are told to go to our rooms. We were informed there would be a surprise inspection that evening. As I head up the four long flights to my room, I think that since I've just arrived, there shouldn't be any problems there!

Not five minutes after we finally reach the fourth floor, as I lay flopped on my unmade bed, our door flies open. I hear Jennifer's quick intake of breath, sounding something like a hiss and look up to see Headmaster MacCleod standing in our doorway. He's wearing riding boots and standing there filling the doorway, tapping his crop on his thigh.

"What? What is this?" He strides into our room and comes to stand at the foot of my bed. I'm still sprawled here although Jennifer is standing (almost) at attention next to her neatly made bed. His crop whistles as it lands with a thwack on my unmade mattress. Then, moving over to my opened luggage, the crop slides under a particularly satiny demi-bra and lifts it so that it dangles off the end.

"And this? I'm confiscating this as it isn't part of your uniform. Don't ever let me catch you wearing this sort of...of...(pause, healthy pause) Just don't let me catch you or you'll know what for!" With that, he turns on his heel and stomps out, slamming the door behind him.

I absolutely dissolve in giggles. The look on his face, his almost stammering.

"Guess I'll have to be sure you don't catch me then!" I choke out between laughs. Jennifer is looking at me like I've lost my mind.

"He'll have it in for you, for sure now, Stephanie!"

Journal Entry

I feel like a little kid sneaking as I write in my journal, under the covers, with a flashlight! Lights out at 8:30! I haven't been to bed this early since, since, since I was a kid! The Headmaster here is a trip. He seems to be out to scare the kids silly, but then, corporal punishment is allowed here, so, who knows! The missing girl, Tina, isn't sounding like the type of kid who would run, but then she had been in some trouble here. Have to ask more questions about her. (Mental note checked off)

Not even looking forward to English class tomorrow! Like I am going to remember my college lit classes! Of course I'd like to see Thaddeus just try and mess with me! Think I'll wear some make-up and my fancy undies tomorrow, hitch up my skirt and see what happens: should be good for a laugh!

Day 2

Journal Entry

Yawn. Now I know why bedtime is soooo early. Been up since 5am! I want some coffee! But no. From what Jennifer tells me, it is oatmeal, toast, juice and milk. Sigh.

My schedule was tacked to the door this morning when I woke up. English and History are my first two subjects. (ugh...what a way to start the day.) Glad I brought some make- up, need it this morning!

Star/Stephany

I find my way over to the Branford Tower for English. Up to the third floor. The class is in what used to be an old church, ivy covered grey brick and the room is in a rounded tower. No desks, but many tables across the back of the room. In the mibble are rows of straight ladder back chairs. These are what we sit on. Several rows of young ladies all seated with their notebooks in their laps, ankles crossed. I had hitched up my skirt so that it was several inches above regulation knee length and managed to walk into class a few minutes late. Headmaster Thaddeus Macleod pointed his crop at the only empty chair. It was dead center of the front row.

"Sit Miss Stephanie. Do not be late for my class ever again. Am I clearly understood?" I merely nodded in the affirmative as I sat down and was informed that whenever I replied to him the correct response was, "Yes, Headmaster."

He walked back and forth across the front of the room for a few moments, gazing at each of us in turn. Devouring is more like it: the guy is a lecher!

"I could see it hesitate;/ Then, in the middle of the open sheet/ Cower down in desperation to accept/ Whatever I accorded it of fate."

"Who can give me the author and source of this quote?"

I raise my hand. I cannot believe I actually

know this one!

"Miss Jennifer?"

"Robert Frost, Headmaster...from his poem 'A Considerable Speck' sir."

"Very good, Jennifer. Now this one."

"A goddess among gods, adored and served/ By angels numberless..."

I know this one too, this may not be as bad as I previously thought. One of the girls in the back was waving her hand madly.

"Yes, Miss Patricia?"

"Milton, Headmaster, Sir. From Paradise Lost; Book 9."

"Good, good. The last quote of this class will be for our new student, Miss Stephanie. Hmmm. let me think on it a minute, ah yes."

"Some that have deeper digged love's mine than I,/ Say where his centric happiness doth lie;/ I have loved, and got, and told,/ But should I love, get, tell, till I were old,/ I should not find that hidden mystery."

Huh? I don't have a clue. Figures. swell, here he comes.

"Well, Miss Stephanie? Do you recognize this? You should if you've half a mind!"

"No, Headmaster, I'm afraid I do not."

The crop lands on the edge of the ladder-back chair, the sound of it hitting the wood reverberating around the room.

"Love's Alchemy...John Donne! Try this one, I'll give you another chance. Stand up, girl. Straighten that posture! Finish the quote and identify it."

"Music hath charms to soothe the savage ________/To soften rocks, or bend a knotted oak."

I know this one!

"Beast, Headmaster, Sir!" Suppressing a giggle at the aptness of my comment, I continue, "Shakespeare!"

"NO! It is breast.' THWACK! The crop lands squarely on my backside! How DARE he?

"Breast!" THWACK!! I move, but he grabs my arm in fingers of steel.

"Music hath charms to soothe the savage BREAST! And it is NOT Shakespeare, but William Congreve in 'The Mourning Bride.' Act i. sc. 1." THWACK!

He launches into a tirade about how totally ignorant I am.

When the bell rings, I figure I am safe from his anger for at least another ten minutes before History.

If girls DO run from here, I am not one bit surprised! Rubbing my backside, I exchange glances with the other girls, all of whom, it seems, are happy that they got off lightly today!

I arrive in history class to find there are no empty chairs. I stand leaning against the wall. The Beast strides in a moment later and calls me to the front of the room. He tells me has to give me an oral (he slides slowly over the word) history test to be sure I am caught up with the rest of the class. Swell!

"Stand facing the blackboard," he says, "face away from the class."

He assigns them some reading and a 1500 word essay due tomorrow! Then he starts firing questions in my direction, all the while walking in circles behind me.

"What year did Socrates drink hemlock?"

Who cares? "Um, '399 BC?"

THWACK! The crop slashes on my legs just where my skirt brushes the backs of my thighs. Damn that hurts! It isn't hard enough to cut the skin, but I'm going to have bruises!

"Yes, but it is 399BC, Headmaster! Why is your skirt SO short?' I pull it down in a hurry; so much for THAT brilliant idea!

"When did Julius Caesar cross the Rubicon?"

Gee, don't guess it is another 399 BC...uh..."69 BC? Headmaster, Sir?"

THWACK! This time the crop lands even higher on my legs! Do I really have to take this?

"No! 39 BC!"

"The term "cult of domesticity" refers to what?"

How the hell do I know? Here we go again and I brace for impact.

"I don't know, Headmaster, Sir."

"It is the idealization of women in their roles as wives and mothers during the early nineteenth century! Don't you know anything? Bend over and put your hands on my desk! NOW!"

I don't like this. The agency is going to hear about it.

THWACK! THWACK!

"OOOOOOOWWW!!"

I want hazard pay!

"One last try to redeem yourself. Or are you answering my questions wrong on purpose? Hmmm?"

NOT!

"Nnnnnnnnnno Sir!, Headmaster, Sir!"

"What did the Bulgar Khan Krum do with the skull of Emperor Nicephorus I of Byzantium?"

Oh shit! Who actually knows this stuff? He couldn't ask when America was discovered or Where the Battle of Bunker Hill was fought? (Breed's Hill...btw)...shit...shit...shit!

"Um... Had it bronzed?"

"No!" THWACK! THWACK! Damn...biting my lip to keep from doing some serious screaming here. I hear a smothered giggle.

"He had it" (as he lifts my skirt over my back revealing my skimpy silk and lace undies to the whole class) THWACK! THWACK!

"Coated in silver and used it as a drinking cup!" THWACK! THWACK!

Ok bub. You and me are going to mix really soon!! Blast, don't dare break cover.

"Seems you had best report to my office, young lady! You are obviously in dire needs of some intense behavior modification. You know underwear like that is expressly forbidden! Take it off. Yes, right here, right now!"

What? Here? "Fine!" I reach up under my skirt and pull it down my legs. As they slide over each mark from the riding crop, I feel each mark burn again. I wad them into a ball. What the hell? They are soaked!!??! Huh? Hmmm. I hand them to the Beast and he manages to sniff deeply of them before putting them in his blazer pocket.

He has a funny look on his face as he says, "Go NOW and wait for me there!"

Journal Entry

Taking a few moments to jot down my thoughts before that Beast of a Headmaster can leave the class. The guy is beyond a lecher, he is a self-absorbed, holier-than-thou cretin! He has some unusual ideas of punishment and correction that I find...I find...shit. Perverse? Strange? Intimidating? Exciting? Huh??? Scratch that. I um, well, don't EVEN know why I got wet before. But I think it was the power struggle. Yes, of course that's it! Couldn't possibly be anything else.

Don't totally know what to expect in his office, but more of the same, I expect. Damn, but my rear is sore!! Feels kinda weird walking around with no undies on. Well, here goes...

Mental note: Absolutely putting in for hazard pay.., and a half!

Headmaster Thaddeus Macleod

Leaving the classroom, I stop a short way down the hall then lean back against wall, suddenly tired. What are today's young women coming to? I wonder to myself, not for the first time. The strain of trying to ensure that things are done properly must be starting to tell. Sometimes I feel like the only person in this school who cares about Rules and Decency.

Miss Pringle did her best. But I had worked with Miss Priscilla, I knew what was expected. Ahhh, there was a woman who understood Discipline. All I could do was try and live up to her exacting Standards

"This new girl is perfect example of the problem," I say aloud, as is my habit. "I can tell she is a Bad Apple. Jennifer is a decent enough girl, but she is easily lead. I think this Stephanie could be a corrupting influence on little Jenni, with her short skirts and her, her, ahh, lingerie," I continue my musings, remembering the undies clutched in my hand inside my pocket. I raise them to my nostrils. With a long, shuddering breath, I inhale her scent from the lacy material. "This one must be watched closely. She has that dangerous combination of intelligence and spirit," I whisper to myself. "Any Corruption must be nipped in the bud."

Stephany/Star

I push open the door to the Headmaster's office. Now I know for sure where the tuition money goes! Large oaken desk fully twenty-four-foot square. Leather chairs, huge fireplace, some sort leather workbench or weight bench - hmmm don't see any weights though - a closet, uh... hmmm ... locked. Books are everywhere. I look at titles: Marquis De Sade, The Punishment of Marisa, How to Chastise, Everything You've Always to Know About Domination, But Were Afraid To Ask, Much Ado About Whipping...

Sheesh...some library! In any other state this would all be against the law, but no, I have to live in a progressive morality state-- a state of confusion is more like it!

From a highly polished coffee table that reflects like a mirror, I pick up a brochure: "The Finishing School: A Private Organization for the Refinement of Obedient Women."

Seriously? Damn! I look out the window and see no sign of our local beasty, so I sit and begin reading.

"The Finishing School is a privately funded school for the training and teaching of behaviors desirable in the Perfect Woman. In our secluded facility, women are taught by the use of various forms of behavior modification to serve and present themselves as per our specifications.

Graduates of our facility are of the 'total obedience' mind-set that we, as proprietors of T.F.S., find so totally lacking in today's society and therefore, seek to remedy.

Two weeks, that's all. In just two weeks we will mold, fashion, sculpt and remake your basic everyday obstinate female into a pliant, accepting, worshipful, obedient example of womanhood. Our strategies include total domination, nakedness-acceptability training, pain avoidance stimulation, aversion therapy, preliminary body invasion tactics and more! All enrolees are given the most up-to-date and pervasive health exam possible to ensure their ability to reach our high standards and to inform us of additional steps that might, medically, be deemed necessary for them to become the ultimate in the female posture. These might include injections to assure proper nipple presentation or to increase sensitivity of specific areas.

Bring your woman in today for a pre-evaluation examination."

Hearing footsteps, I drop the pamphlet on the table and stand up in front of his desk, reaching that position just seconds before the door swung open.

Headmaster Thaddeus Macleod

As I enter the room, my mind races, as I contemplate the challenge before me. How to bring this little trouble-maker to heel, how to break this skittish filly to my will, my rein. She's needs to be bridled.

I can tell by her flustered appearance that he has been reading the brochure for 'The Finishing School', just as I had expected, and wanted her, to do. Does she suspect that she has already made herself a candidate for our 'especial' establishment? I have a feeling that two weeks may not be enough for this one. I sense a steely determination and strength in little Stephanie, So much more interesting than that little mouse Tina. Less contemplation, Thaddeus, I say to myself, time to impose some discipline.