The Headmaster's Indiscretion Pt. 01

I slowly make my way to my desk and sit where I can watch her. I let the silence drag out and study its effect on her. Some have been known to burst into tears after thirty seconds of silent appraisal, not this one. After a minute, I can see tiny signs of nervousness, but decide to proceed.

"I must say, Miss Stephanie, that I am more than a little disappointed in your performance here so far. In less than twenty-four hours at Miss Priscilla's, you have flouted the dress regulations and then added to this misbehavior by demonstrating a woeful lack of knowledge of both English and History. I am afraid that—"

At this point the little baggage has the temerity, the gall to try and interrupt me.

"But HeadMaster,"

Enraged, I hiss at her, "Silence girl! You will speak only when specifically asked, do you understand?" I wait until I see the head nod and notice the lips trembling a bit. Excellent. "I was about to tell you that I am afraid you will have to be chastised and you have only made things worse for yourself by interrupting me. In all my years of experience teaching I have found that there are other ways of getting knowledge to the brain. In the case of girls like you I have found another path is via the posterior." I continue in a softer voice, "Come Stephanie, lay yourself across my lap for a spanking, a most well deserved one."

I watch the shock and horror work their way across her face, seemingly struggling with other, less obvious emotions. I watch her open her mouth to protest and snap, "There are far worse things than a spanking young lady, as you will find out if you don't get over here right now!" Remembering her reaction in the class room I ask, slyly, "Would you prefer the crop perhaps?"

Again her face betrays her and I remember the damp scrap of fabric in my blazer pocket, her moist knickers. I also recall the look of genuine surprise when she took them off and found them wet.

Something about that situation, the crop, the public humiliation or perhaps being forced to submit had certainly turned her on. Was she perhaps that rarest of gems, a natural submissive? I felt my heart quicken and my cock start to stir as I contemplated the possibility.

Star/Stephany

My mind is spinning at full warp. I think of and reject endless possible reactions, words, threats and indignant replies. I don't even like this...this is way out of control and it certainly was not a subject in my agency manual! I want to slug that worm of a HeadMaster, but if I break cover now—shit.

One section of my brain tells me to be a good agent, be strong and handle it, to control my emotions. The other side is being slyly female wondering why I am finding this thrilling, exciting, the feelings of being in a situation beyond my control. Either way, I have to do something. I walk slowly over to him.

He has pushed the chair away from his desk, his bony legs forming a horizontal shelf of a lap. There doesn't seem to be anyway to gracefully lower one's self to be spanked! I haven't been spanked since that time my dad gave me the belt as a 10-year-old when I forgot to shut the barn door and all the animals got out.

Lying there, my head and arms hanging down, my hands on the floor, bent at the hips with my bum raised obscenely, my feet touching the floor on the other side of the chair.

Headmaster Thaddeus Macleod

Again I pause, to build the tension, for her and for me. I can feel this lovely young thing trembling in my lap as she waits. This is the part I almost love the best, regardless of what comes after. Carefully, delicately, I take the hem of her skirt and lift it up, revealing an ass that is just as exquisite as I had imagined. Two perfect, firm globes, lightly goose-pimpled with just the hint of girlish down that I love so much. The shadowed crevice between hints at other delights, but I must have patience. I raise my hand and instruct the girl, "I want you to count each slap now, Stephanie," as I bring my hand down hard on her right buttock.

The first blow causes her ass cheek to quiver and draws a noise that is half grunt, half sigh from the helpless girl. A perfect print of my hand quickly reddens on her bottom, so I add an exact twin to her other cheek. After six more slaps I pause for a heady moment. Her ass is a uniform pink and she is wriggling in my lap. This, and her moans at each spank, before she counts them off, are making my cock harden. I stop for a second and ask, 'How many was that girl?"

After a few seconds and a few ragged breaths, I hear her whisper, "Eight."

"The correct number, but the wrong answer. It seems you need some more intensive education. The correct answer is, 'Eight, Headmaster.'" I take her knickers from my pocket and pinch her nose until she opens her mouth. Then I force the damp and fragrant undies between her lips.

Make-shift gag in place, I take my riding crop from my desk, I bring it whistling down across both cheeks. I am rewarded with a muffled scream and more writhing. Five or six more stripes make a beautiful pattern on her quivering ass. I was about to continue when I feel some moisture on my leg, wetting my trousers. I run my hand up the inside of the girl's leg, starting at the ankle. Rather than resist, as I half expected, her legs part to allow me easy access. At the end of my hand's journey I find a pussy that can only be described as positively dripping wet. Her cunt juices are so copious that they have run down her thighs and soaked through my pants.

With my voice cracking with lust I whisper, "You love this don't you?"

Headmaster and Star/Stephany

No, I do not, Stephany thought. You slimy-assed bastard, her mind screams through clenched teeth and betraying body.

"Don't you, you little tart?" Hearing no answer, he jammed two fingers between her pouting, puffy labia. They slide in without resistance, producing an exciting wet noise. He asks again, "Do you like this, Stephanie?" Another blow from the crop; another stripe. "Do you enjoy having your ass tanned?" Twisting his fingers deeper inside her wet cavity, another slice from the crop. "Do you?"

No I most definitely do...not! She was in such a quandary. He wants me to say that I love it! That it is getting me off. He is such a sick puppy! Oh blast! I hate this! Like a dam bursting, she wails, "Yes Headmaster, I love it."

Delighted, he continued fingering her. "And this isn't a virgin cunt, is it Stephanie? This is a well fucked slut's cunt isn't it?" Whilst waiting for an answer he squeezed a third finger into her wet hole.

"No, Headmaster. Yes, Headmaster, Sir."

"Tell me what you are!" She understood the question.

"I'm a well fucked slut, Headmaster."

Pleased, he moved on to the next, obvious question. "Would you like me to fuck you, Stephanie?"

Not until Hell freezes over, she thought, biting her lip.

Just at that moment the phone rang. The Headmaster nearly erupted in anger. My knows secretary to hold all my calls. As a graduate of Miss Priscilla's herself, she knows what will happen if she displeases me. Then he realized it was his private line, only used for calls of the most urgent kind. He ordered the girl off his lap.

"Stand with your back to me against the wall. Hold your skirt up so that I can see your ass."

Once he saw that she was obeying him, he picked up the phone.

Standing there, facing the wall, like a little girl standing in the corner, Star seethed. Hold your skirt up so that I can see your ass, his words echoing in her mind. Who the hell does he think he is?

She heard him murmuring ... but all she could make out were a series of Yeses and Oh, reallys. She also could hear a muted giggling from outside in the hall. Little brats! I wonder how long he is going to keep me standing here? Oh, shit, he's finally getting off the phone.

"Miss Stephanie, come here!"

She dropped her skirt and walked over to the desk. "I'm leaving your office now, Mr Headmaster, Sir! I trust you have had your sadistic tendencies fulfilled for the day. I have homework to do!"

With that, she walked over to the office door, hearing the scrambling of feet as she reached for the door knob. She heard nothing from the beast, except for a strangled intake of air. She walked out, leaving the door open behind her.

Journal

Day 2, continued

I want hazard pay! Nowhere have I ever read that agents put up with this kind of crap!

(The following paragraphs were written, then scratched out)

And I don't even know why my blasted body reacted as it did! My ass hurts and yet I was dripping wet! That my body could betray me so! How could any of that have turned me on? Taking a crop to ole Thaddy boy ... Now that, that would be a trip! Yeah right. Sigh.

(Return to journal after scratch outs)

I can understand why students would run away from here, but not the fact that they often come back and appear to be happy here. Unless, unless that pamphlet has something to do with it! Maybe I should act up tomorrow in English. Hmm Oh my aching butt. All in the line of duty, sigh.

Two weeks--the girls go missing for about that length of time. I might have something here. Drat, here comes Jennifer et al...

Star/Stephanie

"Are you ok? What did he do to you? Did you get spanked? We warned you!" Their voices sounding excited and caring and something else I can't quite put my finger on.

"You are the new girl, he always does that to them. You didn't stand a chance!'

Gee...how nice!

"C'mon...it's lunch time!"

Headmaster Thaddeus Macleod

Thaddeus sat at his desk making a call.

"Yes, Dickon please ... oh yes ... Hello, Dickon. Just got a call from Ms Winthrop over to the agency. ... Yes, seems like she's the new Head over there! ... Yes, amazing isn't it, what our graduates can do. I have some news for you. She's just fired the chief investigations man over there and called to inform me we have an intruder here. The new girl, Stephanie, eh what? ... Oh yes, she does actually, quite a nice fanny, indeed! At any rate, she isn't a student. The agency put her here to investigate our school.

"I think we should arrange for her to be brought to ... yes, tonight would be good. ... Actually? She's an excellent candidate, feisty little thing. Her real name's Star or some such. What? ... Oh no, pity, really. I was just getting ready to blister that fanny of hers when the call came through. Soon enough though. Yes, she'll be begging before too long. They all do, eventually, don't they? ... Yes ... yes, okay then, you make the arrangements. She's the bed on the left. Tonight then, excellent! ... Yes, I'll see you tonight."

Sometime after midnight a door on the fourth floor opens and two men creep in quietly. Going over to the bed on the left, one of the men shoves a sweet smelling rag over Stephanie's mouth and nose and she quickly relaxes in a state of unconsciousness. One of the men picks her up, throws her over his shoulder and exits. The other grabs some of her clothes, her bag and then notices the journal and grabs that as well. As the door shuts behind him, Jennifer rolls over in her bed, heaving a sigh of relief before falling back asleep.

Star/Stephanie

I wake up feeling like I do after a night of too much to drink at BG's, our local pub. I try to move, but I can't. My eyes begin to focus. I shake my head. Oh oh, bad idea, ouch! What in the hell? I can't move. My hands and feet are tied, spread-eagled on what feels like a table in my doctor's office! Something's tied across my eyes, blindfolding me. Where the? Oh this is not good at all. As a breeze moves over me I realize I'm naked.

I hear a door open and some people come in.

"Well, Dickon, what do you think? Think Miss Stephanie, or should I say, Star, will be our new rising star graduate?'

NOT! Crap! Somehow, they know. That voice belongs to ole Beasty boy himself.

"Hmm, guess that is up to the young lady here, isn't it?"

I feel him run his hands over my breasts, flicking each nipple with thumb and forefinger --hard! Hardened before, due to the chill in the room, I can feel them harden to puckered point. I feel him take each nipple between thumb and forefinger. He twists, pulls, and releases. I'm sure they are watching with interest the expressions which fly across my face. I do my best to school them into a blank expression. Running his hand further down my body, he reaches the nest of curls above my pussy.

"These will have to go," he says, pulling at one of my silvery gilt curls. Dipping his hand lower, he runs a finger down along my clit, causing me to jump and him to comment, "She's positively dripping! Oh we have a live one here, alright!"

"So, HeadMaster, what is next for our, ah, new star pupil?" asked Dickon with a low laugh.

"The primary exam, of course. The Doctor will be here in the morning. I hear he has several new "Doctors-in-Training" that will be here too. He will report to me after her initial examination."