tagGroup SexThe Head Master and Mistress Missy

The Head Master and Mistress Missy



After the recent arrests and publicity concerning Spenser Wainwright and wealthy socialite Missy Ellsworth, known through his published works as the 'Head Master and Mistress Missy', the following manuscript came to light. Now that a settlement had been reached with the Crookshank Academy, this work of fiction can be published. Crookshank admits no connection or liability associated with any of the many acts of sexual excess and 'training' of the 18- and 19-year old students of Wainwright's fictional Academy depicted here or elsewhere.

Based on court testimony and stylistic comparison to Wainwright's own popular series of 'porn lite' confessionals centered on the ribald adventures of the Head Master and Mistress Missy, written under the nom de plum of Dexter Wayne, it can only be assumed that the unnamed male protagonist of this manuscript is the author himself. It appears to details his first sexual encounter with a young Ellsworth and Gertrude 'Trudy' Maxwell, the un-indicted co-conspirator named in government filings who serves as the Academy's admissions officer.

We hope the reader will find this an interesting light shone on how the notorious program, and the Head Master's sordid career, may well have begun, years ago.

Update: with the surprise tossing of all charges against the accused by District Judge Miranda Harkins, Wainwright is again Dean at Crookshank and Ellsworth has retaken her seat on the Board of Trustees. The Academy reports the recent publicity has almost tripled the applicants to their post-graduate 'finishing training' program.

The Head Master, A Beginning

- Unsigned, but presumed to be by Dexter Wayne

He slowed mid-step at the sounds of feminine laughter. Well, female laughter. One voice was feminine, a trilling of silver bells. The other, not so much. Loud, clear and distinct, it blended the honk of a goose with the bray of a cartoon burro.

Only one girl on campus had ever made a sound like that. She graduated last year and she had no business being in this dorm room tonight, the door closed. The entire floor should have been unoccupied. Except for last minute snowstorm and a canceled flight, he would have been the only resident in the sprawling brick building. And the single snow-stranded student with permission to be here would be the likely source of the silvery trills, not the barnyard horn blast.

Each wing of each dormitory, their pale pastel walls pocked with glassless doors like a cheap hotel hallway, ended in a faculty apartment. Most were occupied by families: couples, some with small children, primarily newer, younger teachers. His last minute hire at the college preparatory Crookshank Academy, mid-term nearly a year ago now, had included 'room and board' in the offer and he took over the two bedroom apartment previously inhabited by a couple with two kids, a mathematics instructor who had left on an abrupt academic sabbatical.

The dorm heat had been turned down for the ten day Christmas holiday. He had given the stranded senior, Missy Ellsworth, a small electric space heater from his closet before retreating to his apartment. A phone call from the Dean at just after nine that night inquiring about the unusual arrangement did not surprise him. Dean Kirby was a micromanaging busybody, but not one who would consider needlessly going outside into the bitter cold wind that carved the deep, powdery snow, still falling, into ever shifting drifts.

The call had left him with strict instructions to have the girl only use a specific ceramic heater to ward off the frigid winter night. Anything else would void the insurance or something. The apartment had come with such a heater, but of course it had not been the one he had found and plugged in for her.

Now he stood, motionless, approved ceramic heater under one arm, in the heavy grey sweatshirt he'd gone back to his apartment for as soon as the chill of the unheated hallways hit him. The unique familiar sound honing his awareness, he noticed a faint line of wet spots, loose footprints, trailing down the hall, ending at this room.

Through and under the wooden door, the familiar braying laugh came again. It brought to his mind a memory from last Spring, at the conclusion of the regional track championships. They had been held at the academy for the first time, showcasing the brand new athletic complex.

The school's 4x100 relay team had managed a surprise Silver medal. One of the four on the raised podium stood out. Shorter than her three teammates, she noticeably filled her nylon tracksuit, top and bottom. Trudy Maxwell had been unofficially dubbed 'Trudy wit da Booty' but 'wit da Boobies' was also heard around campus when no disapproving ears might catch it.

The tall, rather severe looking woman representing the regional athletic commission presented Trudy with her medal last. As the curvy girl bowed her head to accept the ribbon being placed around her neck, her short bob of thick dark brown hair had fallen forward, hiding her face.

Jennifer Wise, the fastest member if the team and Trudy's good friend, gave a sudden loud honk. It didn't have the resonant quality of Trudy's reverberant laughter, but it had still carried. And it was answered.

Trudy was popular and friendly and uncruel, the last being a bit too unusual among her peers. The remaining two relay team members had not been alone when they added their own imitation of the distinct laugh. A chorus of affectionate hoots had come from dozens in the crowd.

The brunette's broad, bright smile when her head popped up in shock, catching the medal's ribbon at an awkward angle on one ear, had showed she didn't mind the public teasing. Then the official and Trudy had both reached for the ribbon at the same time, the pursed frustration pinching the tall blond's face a marked contrast to the short girl's beaming, infectious joy.

There'd been a tangle of hair and ribbon and hands before Trudy lost it, granting the assembled crowd a lesson in laughter.

Braaaay. Honk. Bray. Honk honk honk. And repeat.

As the crowd joined in, the official had finally managed a brief smile before a final, petty adjustment of the ribbon near Trudy's shoulder.

He could still clearly recall the way the small tug had brought his eyes and many others to the suspended medal it shook, swinging free in the sizable crevice between the girl's round, full breasts, bouncing freely under her stretchy top with each hearty laugh.

Those full firm breasts. Pushed hard against his chest. That's what the sound of that laugh brought back most. Pushed tight against him as she stretched up on her toes and kissed him, tears in her eyes.

Track season had ended. Graduation, a week away. Trudy had knocked on the door to his office, already ajar. Her fade was tight with fear.

"What's wrong, Trudy?" He saw the thick sheaf of typed paper in her hand, knew this was not a term paper issue. Though final versions were due Monday.

"My..my dad. He's...somebody shot him!" The tears released.

"What? Is he..." He knew Ellison Maxwell had recently been appointed Ambassador to Somewhere, reward for being a top campaign 'bundler' in the last presidential election.

Her lower lip was pushed out, nose running. "They don't know if he'll make it."

He'd stood when she rushed in looking scared. His arms wrapped around her without a thought when she leaned into him, shaking, after she dropped the sheaf on his desk. He'd stroked her hair, tried not to think about the breasts nestled under his own chest. The firmest, most resisting breasts he could remember feeling. "Shhh."

She had looked up at him, face a smear of grief, his hand still alongside. "They shot my Daddy!"

He'd opened his mouth to say something. Something reassuring, comforting. Instead, Trudy kissed him, hard. Tongue, doubts, lips, fears, all unleashed in one fierce kiss.

Then she had run, pausing at the doorway. Her words came out in a streak, muffled by the back of a hand wiping at her nose and eyes. "Gotta go the airport. I'll have the paper edited when we get back I hope. Thank you."

"Thank you." He didn't say it loudly, or before she was gone, and he was back in his seat, alone. He traced his lip with a fingertip where she had kissed. He could taste her still, feel how she'd pressed into him.

But Trudy had graduated last year; the kiss had been last spring. He had seen her at graduation, heard her father would survive, but they hadn't spoken more than a few public words. She was attending some small college in New England. Dartmouth?

He hesitated outside the door. As the resident faculty, he had the full right to simply open it without warning. The key was in his pocket though students were instructed to not lock their doors as part of the school's deeply engrained Honor Code.

He knocked. "Missy? Dean Kirby insists we switch out your heater."

He heard an immediate rustling as he spoke, low panicked sounds of motion and furtive shushings. The universal code for "Quick! Hide!"

He turned the unlocked knob and entered.

Trudy Maxwell, she of the distinctive honking laugh and pneumatic chest and unexpected kissing, had graduated. Other than himself, he knew that the only person authorized to be in this dorm tonight was Missy Ellsworth. Her flight home for Christmas break, already delayed, had been cancelled due to the snow storm. Now the roads were closed too, with drifts almost burying some cars.

The Dean had told him there was nothing to be done until the streets were cleared. Missy would have to stay in the dorm, and as the teacher couple who supervised the girl's wing was away with family, he was responsible for her. He was solely responsible for Missy Ellsworth, all four foot, ten inch blond bundle of gymnastic, scholastic and sarcastic dynamite.

Missy was sitting up in bed, face flushed. No one else in sight. He could see her oversized Dartmouth shirt rise and fall with controlled breaths, like an athlete calming herself before a performance.

On the desk chair, a hooded down jacket, damp with snowmelt, hung crumpled above a pair of rubber-bottomed, leather-topped 'Bean' boots. Water puddled on the old hardwood floor, forming a narrow moat around each boot. A few stubborn clumps of slushy snow still clung to the stitching connecting leather to rubber.

Her nervous, wide blue eyes were on his as he looked back at her, away from the wet gear.

He raised the heater he carried and his eyebrows, smiling. "The approved model. The Dean was adamant."

As if on cue, the heater to be replaced buzzed to life, the red glow of the elements quickly appearing through the front grill. He could smell the somehow stale smell of the ozone, like it killed any freshness in the air.

He grimaced. "This one should smell better, at any rate."

He stepped toward the glowing heater on the floor next to her bed, where he had placed it earlier today.

"No!" He jerked to a stop, the ceramic heater, a smaller, sleeker package, suspended in both hands.

"Ah, um, can you put it over there?" A tiny hand pointed to the corner near her desk.

"Okaaay." He stood, looking at her, the desk area, back to her. "I'll need to clean up the water on the floor first. And I'll need to take the old heater, of course."

She made a involuntary, nervous glance down toward the floor by her bed. He had used the plug in the wall covered by her footboard, reaching under the bed when he'd turned it on earlier.

"Oh. I can get that..."

He cut her off. "Were you out in the storm recently?"

"What? No way."

He set the new heater down on her neat desktop, stood next to the damp coat and boots and crossed his arms.

"Are you sure?" He paused until she opened her mouth to respond, then cut her off. "Remember, you and I are both bound by the Honor Code."

The sweet innocent little girl came out. The lower lip pushed forward, the outside of her eyes drooped as twin moist shimmer told of tears beginning to form. The response that had probably kept her out of all kinds of trouble with her daddy, Parker Ellsworth.

"Isn't your father on the Honor Board?" The pout deepened. The pout that might not be so effective on Daddy when he's sitting on a board to hear charges against his little girl. Even as he said it, he realized Eleanor Maxwell, Trudy's mother, was also on the Board. By the changing look on the blond gymnast's face, she shared his realization.

"So think about your answer for a minute. And get your story straight in your head. I don't want to hear any lies from you, because that would put me in a very awkward situation. One in which I'd have no choice but to refer you to the Dean and the Board."

He picked the heater off the desk, stepped toward the foot of her bed. "I'll just switch out the heaters while you think things through."

Two girls made sudden sounds of protest, the second one being much fainter and clearly from under the bed. That sound registered only dimly though, as his eyes had caught a glimpse of something else.

Missy had risen up on her knees when he moved toward the glowing heater. Immediately, she sat back down, pulling the Dartmouth shirt down around her tiny hips. She was wearing no underwear and he had seen a flash of thin, tangled hair, darker than on her head, and of a small indented groove below, spaced evenly between where two strong, lean little thighs began.

It took an inward shaking of his head to focus again on the noise from under the bed, his thoughts reluctant to let go of the image of the little gymnast's exposed crotch and flat lower belly, followed by the hard points of two nipples stretching the t-shirt as she pulled it down, too hard, to cover her upper thighs.

"Did you hear something?" He said it casually, but loud enough for anyone hiding to hear.

"Like what?" Smart girl. Answering a question with a question couldn't be a lie.

"Like someone hiding under a dorm bed, near where I need to plug in the new heater." At least neither made a sound. He waited. "Should I look?"

Blond hair vibrated at the tiny shake of her head. The tears threatened.

"Are you scared, Missy?" The nod was smaller than the shake had been. One tear rolled down her cheek after catching, stalling on the upper edge of her high cheekbone.

"I don't want to scare you." He raised his voice. "Trudy. Come out of there. Now."

Missy's mouth opened in a 'O' and a distinct squeak leaked out from under her.

"Trudy?" He impressed himself with his deep growl, exuding the mature authority he could still be made to tremble under.

"I can't." The voice sounded defeated.

"Do you need me to help you?"

"No!" Both girls cried out.

"Then come out here now, before this gets worse."

"She can't!" Two tiny fists pounded the mattress.

"Why not?"

Missy pressed her lips tight, struggling to frame an answer, unwilling to risk a direct lie that could put her in front of her public father.

"I'm naked." The reluctant answer from below. Resigned. "Could I at least have my shirt?"

He resisted a smile. "What's it look like?"

"Grey. It says Dartmouth in big green letters. It should be right there."

He looked at Missy, let the smile out. "Missy? Could you help Trudy with her shirt?"

Her pretty blue eyes bugged wide. Then they hardened. Not with anger, with determination. She set her small jaw with its cute little almost pointed chin.

Hands that had recently stretched the shirt down tight over her hips, now pulled it up and over her shoulders and head in one practiced crossed-arm motion. For an instant the young gymnast seemed to pause, the Dartmouth shirt stretched over her face and arms, her back arched, her nipples pointing out, hard and alone on her muscled but flat chest. Her abdominal muscles rippled, not simply the six pack down the center, but also the shifting moguls forming over and below her ribs.

He stared. She was gorgeous, a fantasy of fuckable fitness he had never been able to fulfill. The shirt came off. She held it in her lap, her chest exposed, and stared back at him, strong and defiant. Leaning over the edge of the bed, she tossed the shirt under it.

"Here ya go." The confident look disappeared in a deep shiver. The room was bitter even with the heater running. She slipped down, pulling the covers up to her chin, shivered again.

With a grunt, Trudy's dark hair appeared. Followed by shoulders, hands, arms. Another grunt when her full chest squeezed out from under the low wood bed. Her curvy hips required another wiggling push. She gave a single bray of laughter at she slipped free.

He got a quick glance of her bare bubble butt before she stood, pulling the shirt down much like the smaller blond girl had, facing him. On the bigger, curvier girl the attempt to cover up accentuated her breasts and called more attention to her smooth, naked legs.

He certainly hadn't forgotten Trudy's breasts, but in her absence it was easy to suppose that memories were faulty and subject to exaggeration. Not in her case.

With her college shirt stretched tight over them, he flashed to last year, Track singlet bouncing over the almost overfilled orbs. Many girls - well, some girls, and most of those didn't run sprints - had bigger breasts, but Trudy's were different. Like a ball inflated past the recommended range, the bounce changed. Not bigger, but stretched tight, full and extra firm in a way nature didn't often provide. A bra would impede their motion, their fluidity and bounce, might change their shape, but could not supply any additional loft or lift. The lift was built in.

Currently, stitched-on letters "ART" and "OUT" each reshaped one breast, compressing it, managing to make them look even fuller as they met in the middle under M, while curves of Fibonacci-like grace formed past D and H. Even in the cold only the mere slightest of bump for each nipple showed, almost a shadow.

The nipple-shadows, and the resilient flesh around them, shook as a shudder passed through her. Bare feet shuffled in an almost-dance on the cold hardwood floor.

"Are you cold?" He had to say something, to take control. Too many times he had cum these past months, picturing this girl, remembering her pressed against him, her tongue eager against his. And, more recently, picturing the little blond now staring at him. At his crotch. At the uncomfortable bulge newly grown there.

Trudy nodded. Her teeth almost chattered. "Uh. Huh."

"Where are your clothes?"

A violent shudder past down her body, starting at her shoulders. The reflexive movement was enough for him to glance down and see dark hair in a small dim triangle for an instant. She looked around the small room. "They're..."

"For god's sake, get in here. You'll freeze." Missy lifted the side of the thick comforter and sheet that covered her. She made an effort to hide her naked body from him, but kept her attention on the girl. Trudy turned, listless, unsure. Missy's arm came up. "Come here, baby. Let me hold you."

Trudy slipped into the bed, into the smaller girl's arms, under the fluffy down. Missy held her, kissing alongside her brown hair. Her blue eyes looked up to find his. "Isn't this what you always wanted? To catch the two of us in bed?"

She lowered her eyes. Shifted down enough to kiss at Trudy's throat. For someone with such a harsh laugh, the cooing, purring sound of satisfaction she made was a surprise. The curvy graduate rolled onto her back, following Missy's nudges. He saw what could only be Trudy's knee moving the comforter toward him, legs spreading under the covers.

The small gymnast leaned over her, reaching one arm down in the direction of the region Trudy's knee had revealed. He had no trouble imaging details when the cooing sound rose in pitch, her face tightening at new, stronger sensations.

Blue eyes flashed back up. "Aren't you going to stop us? This should be reported immediately to the Dean."

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