Alternative Schooling

Alternative Schooling

Chapter Two

As I pulled through the gate onto the drive to the house, I was rewarded with another reaction from Sarah.  Another in a series of them that had started with a belated "thank you" for the meal and a heartier "thank you so much" for getting her away from Billy.

I'd reserved seats on the latest possible flight back to Florida from San Francisco, so there was enough time to stop at a department store and pick up new clothes for her.  All of her things had been taken by Billy, except for the clothes she was wearing and he'd kept her in those for several days.  I'd offered to go get her things from him, but she declined, not wanting to see him again.  I sensed a certain reluctance to abandon them, though.  She'd probably lost some things of sentimental value, but didn't want to face Billy again to retrieve them.  I'd made a note to call Billy and have him ship the things to me -- her gratitude when she got them back would tie her closer to me.

She'd ooed at the first-class seats, falling asleep in exhaustion shortly after take-off, then aahed when I showed her to the Jaguar in the airport parking lot.

Now, passing through the gate onto the ten acres surrounding my house, she looked around in awe.  The tree-lined driveway curved and the house came into view, two-stories and two-hundred feet of frontage in the style of a Mediterranean villa.

“This is a school?” Sarah asked.

“It’s my home,” I explained.  “The school is part of it, there are only ten of you, after all.”

She was silent as I pulled the Jaguar around the circular drive to the front of the house.  As the car came to a stop, the front door of the house opened and a girl came out.

Rebecca, 5’-11" of statuesque blonde, looking more twenty-five than her real age of seventeen -- dressed, for purposes of greeting Sarah, in jeans and a t-shirt instead of her normal, student uniform.  I'd chosen her to greet the newcomer because of her open, friendliness and her older appearance; she'd seem to Sarah like an older sister, knowing and trustworthy.  Rebecca knew exactly what to do and, without a glance to me, she pulled open the car door and squatted to look Sarah in the eye.

"Hi!" she beamed, showing a mouthful of white teeth.  "You must be Sarah.  I'm Rebecca.  Come on, let's get your stuff and get you settled in."

With that, she handed Sarah out of the car, retrieved her new backpack from the rear seat and warmly wrapped an arm around the smaller girl as she guided her into the house. 

As I watched them go, I smiled, knowing that Rebecca would keep up a non-stop chatter of innocuous conversation as she showed Sarah to her room, virtually ensuring that the two became fast friends.  I thought wryly that I'd miss Rebecca when I lost her in a few short months -- she'd be leaving to attend Cornel, ultimately headed for their law school thanks to exceptional SAT and LSAT scores, plus a generous donation to offset the rather unorthodox nature of her high school transcript.

I entered the house behind the two girls and made my way quickly upstairs to my bedroom.  Once there, I opened a large wall cabinet and turned on the monitors for the house's surveillance system.  On the largest screen, I put the view from the dormitory, where Rebecca and Sarah would be entering shortly; on another screen, I called up the feed from the classroom to check on the remaining students.  As I expected, all was in order, the eight other students, three boys and five girls, each sat at a desk, studying whatever project they were currently working on. 

On the larger monitor, Rebecca entered the dormitory with Sarah, leading her down the middle of the room, past the two rows of bunk-beds, three on each side of the room.  I could see Rebecca gesturing and talking, explaining the setup to Sarah, but didn't bother to turn up the sound.  The two girls crossed the room to a door in the far wall which led to the guest room and bath.

The placement of the guest room was deliberate.  Putting it as part of, but apart from, the dormitory ensured the guest, the prospective student, would have to interact intimately with the other students in the dormitory; would have to cross the dormitory to go to and from the guest room.  This exercise gave the guest a sense of privilege, which would, in turn, engender a sense of guilt in the personality types I looked for: someone searching to belong to something, longing to be part of a group or family.

Where the guest had a private room, the students shared one, and each had a smaller bed than the guest received.  Where the guest had a private bath, the students shared a bathroom where the only privacy was in the toilet stalls, even the showers were an open, communal affair for both sexes.  Where the guest had normal clothes, the students all wore the same school uniform, except for field trips or when household duties required more protection.

All of this gave the guest privilege, but would also set her apart.  Feeling guilty that she had what the others did not and wanting to belong, she would soon be willing to give up the extras and join the group, which meant joining the school.

Watching Rebecca and Sarah chat as they put Sarah's few things away in the guest room, I glanced at the stack of mail on my desk where a collection of envelopes caught my eye.  SAT results from the last round of testing, and one in particular that I wanted to check.  I retrieved that one and opened it. 

Richard had been distracted for some reason on the day of the testing, so I expected his results to be disappointing.  As I read them, my suspicions were confirmed and I reached forward to trigger the intercom to the classroom.

"Richard, come to my room," I said.  I watched him rise from his desk and hurry from the room; less than a minute later the door to my bedroom opened and he entered.

At sixteen, Richard was almost six feet and well-built thanks to the school's exercise regimen.  He wore the school uniform of a white silk shirt, collarless and short-sleeved, that fell to just above the bottom of his buttocks and loose, white cotton boxers.  He had dark hair and was tan from time spent at the pool and working outdoors on the school estate.

"I have your SAT results, Richard."

A look of trepidation filled his eyes and he bowed his head, shoulders slumping.  "I'm sorry, Sir," he said softly.

"Thirty points too low, Richard."  He glanced up at the piece of paper in my hands and swallowed hard.  "Get the chair, Richard."

He walked slowly to a corner of the room where a plain, wooden chair sat, lifted it and moved it away from the corner to the center of an open space.  Then he pulled the silk shirt over his head and drew off the boxers, leaving himself naked.  He faced the chair and bent over, resting his forearms on the arms of the chair and gripping the uprights of the chair-back tightly with his hands.

I left the security monitors and crossed the room to him, retrieving a rattan cane from the dresser top as I did so.  "Thirty, Richard."

"I'm sorry, Sir," he repeated, a quaver in his voice. 

There might be fear in his voice, but his body betrayed him as I saw his cock was already hard and straight.  Two years under my tutelage had blurred the line between punishment and pleasure, between reward and pain.  I laid the cane gently across his buttocks for a moment and said quietly, "I'm very disappointed in you, Richard."

"I'm sorry, Sir," he whispered again, and when I heard more shame and regret than fear in his voice, I knew he was mine.

I drew back the cane and sent it forward with a whistle to crack against the skin of his ass.

"One!" he yelled.  "I'm sorry, Sir!"

I drew the cane back again and took a moment to gaze at the red line drawn across the young man's buttocks, already raising in a hard welt.  I moved my arm for another blow, parallel to and lower than the first.

"Two!  I'm sorry, Sir!"

And a third, above the first.

"Three!  I'm sorry, Sir!"

The fourth blow I put more force behind, laying it atop the line of the first.  Richard's breath exploded from him a strangled scream and he lurched forward, quickly returning to position and inhaling to reply.

"Four!  I'm sorry, Sir!"

On the fifth stroke, his voice broke and by the eighth tears were streaming down his face.  The tenth stroke brought a full-throated scream of agony from him and he couldn't catch his breath in time, before the next stroke, so the eleventh became number ten in his count. 

He began whispering a litany of "i'msorryi'msorryi'msorryi'msorry" to himself, miserable and desperate not to miss counting another.

When the stroke he'd count as fifteen landed, his knees gave out and he collapsed forward, face pressed to the seat of the chair, mouth half open as he murmured, "Fifteen, I'm sorry, Sir."

"Up," I ordered.  "You don't get any breaks when it's a punishment.  Get your ass in the air or we start over."

He scrambled swiftly to his feet and as his ass reached the proper height I brought the cane crashing down hard.

"SIXTEEN!" he screamed, voice cracking.  "I'm sorry, Sir!"

After twenty, I paused.  Richard's ass was a mass of welts, covered in red lines and weals.  Tiny drops of scarlet showed where the skin had broken.

"Spread your cheeks, Richard," I ordered calmly.

Richard whimpered, hesitating, and I quickly leaned forward to whisper in his ear, "Now.  Or you'll start every morning this way for a week."

He moaned a low sound of despair, but took his arms from the chair to reach back and gingerly pull the cheeks of his ass apart.  Having to grip and pull on that tortured flesh must have been agony, but what came next was worse.

Now, faced with the white, unmarked surface of Richard's inner ass-cheeks, I used the tip of the cane instead of the length.  Sending it with a deceptively casual flick of the wrist to cut into that tender flesh.  Richard screamed afresh, struggling to stay upright without the support of the chair and struggling more to keep count of this fresh onslaught. 

Stepping from one side of him to another, so I could pay equal attention to each surface, I brought him to a count of twenty-nine strokes.

Then, taking careful aim and with a violent flick of my wrist, I laid the tip the of the cane directly onto his anus for the thirtieth. 

Richard let out a roar of agony and collapsed to the floor.  "thirty," he moaned in a hoarse, shallow voice.  "i'm so sorry, Sir, i'm so so sorry."

"We're not quite through, Richard," I told him.  "Have a seat."

Whimpering and crying, Richard struggled off the floor and gingerly sat.  Tears streamed down his face and he winced as he tried to find a way to sit that wasn't torture, but again, his body told a different tale: Richard's cock was full and engorged.  Even as the pressure of sitting on his abused ass sent fresh waves of pain through him, his cock throbbed to them.

"Would you like to take care of that?" I asked, indicating his cock with the tip of the cane.

Richard gasped in relief and gratitude.  "Yes, please, Sir, yes."

"Slowly," I told him. 

Richard's hand flew to his cock, grasping it and he began to slowly pump up and down.  His face relaxed in relief as this new sensation overrode the pain from his ass.  Within moments, within a few strokes of his hand, he moaned again and begged, "Please, Sir, may I finish?"

"Not yet," I ordered and his hand froze.  His face contorted in a rictus of concentration as he fought to stop, his breath coming in shallow gasps.

"Keep your hand on your cock," I told him as I raised the cane and brought it down atop his lower thighs. 

Richard's body convulsed, jerking in the chair and that movement slid his cock through the hand grasping it.

"Oh, god, please, Sir, please, Sir, please, Sir."

"Not yet," I told him, bringing the cane down again, higher on this thighs this time.

Richard was keening now, a thin, high-pitched squeal the only sound from him as he fought for control.

I raised the cane again and brought it down, harshly ordering, "Now!" as the cane landed across the top of Richard's thighs, high enough to catch a bit of his ball sack and draw a line of pure fire across it.  Richard jerked with the impact, threw his head back and howled in ecstasy and agony combined as his cock exploded, shooting come into the air.  He arched his back, supported only by his heels and his head against the back of the chair, then his body spasmed and he howled afresh, collapsing to the floor where he curled on his side and moaned.

I looked back to the security monitors and saw that the guest room was empty.  Quickly scanning through the cameras, I found Sarah’s image in the guest bathroom, just stepping into the shower, and put that feed on the largest monitor.  I’d been right about her figure: small breasts, a B-cup, at most, and with a narrow waist and hips.  As she adjusted the water temperature, putting her back to the shower, I enjoyed the view of her ass, which was small and tight, anticipating the first time I’d feel those cheeks under the palm of my hand as I punished her.

Richard moaned again and I turned my attention to him.  He’d taken his punishment well and it was time for reassurance, so I knelt down beside him and placed a hand gently on his hair.  At the touch, he reached out to me, hands grasping my hips and pulling himself toward me to rest his head in my lap.  I pressed his face firmly against my crotch, feeling his hot breath on me through the fabric of my pants and wrapped my other arm around his shoulders, drawing him nearer.

His body shook with sobs for a time as I rocked him gently, then calmed.  “I’m so sorry, Sir,” he whispered.

“I know, Richard,” I told him.  “It’s okay now.  I know you’ll do better next time.”

“I will, Sir,” he agreed, holding me tightly, then he moved one hand from my hip to the waistband of my pants, clutching at them.  “Please, Sir?” he asked in a tiny voice.

I smiled at this further sign of how completely he was mine.  Ass bruised and bloodied by my blows, his thoughts were only about regaining my approval and pleasing me, seeking comfort and reassurance by filling his mouth with my cock.  I raised up a bit in silent approval and his hands flew to undo my belt and pants, sliding them down to mid-thigh.  Hungrily his mouth engulfed my cock, sucking hard, tongue swirling desperately, his arms wrapped around my waist and pulling him tightly against me.

On the security monitor, Sarah was in the shower, facing the camera and working shampoo into her hair.  With her head tilted back and arms raised, her torso was stretched, breasts pulled tight.  I groaned in pleasure, a combination of Richard’s mouth working on me and anticipation of having Sarah stretched like that for other purposes.  Her arms and legs bound, her breasts stretched and tight, waiting for my ministrations with teeth and clamps and wax.

Roughly, I grabbed the back of Richard’s head and thrust forcefully into his mouth.  He immediately adjusted his position, stretching his neck and opening his throat to take the full length of me.  With both my hands entwined in his hair, I thrust again, grinding my pelvis hard against his face. 

I glanced at Richard’s ass, lines of raised welts covering it, starting to turn dark now with bruising.  I wondered what Sarah’s reaction would be when she saw her first caning here and how she’d take it when it was her turn. 

Looking again at Sarah’s naked image on the monitor, I decided that Rebecca would be her first female encounter.  The girls were very different physically and the thought of the contrast between Sarah’s petite figure and dark hair with Rebecca, full-figured and blonde, excited me.  It was only a question of when to arrange it and whether it would be forced or seduction.  Both scenarios had their attractions: Sarah with hands bound behind her back, helpless while Rebecca spread her legs and struggling against me as I forced her face into the blonde-girl’s pussy, smothering her there until she licked and sucked as ordered; or, something more private and gentle, with the older, trusted girl taking advantage of that trust to seduce her and teach her the pleasures of another woman. 

With those image in my head, I began thrusting over and over into Richard’s mouth, fucking his throat hard and fast.  With a groan, I thrust deeper one last time and held it there, flexing my cock as I crushed his face to me and filled his mouth and throat with my come.  Richard swallowed quickly, over and over, locking his lips around me to capture every drop.

Without warning, I reached out and brought the palm of my hand down on Richard’s abused ass with a resounding smack!  His body spasmed at the sudden pain and he screamed hard around my cock, the vibration of his cries sending fresh waves of pleasure through me.  I squeezed the cheek hard and released it several times, enjoying Richard’s pain and the sensation of him expressing that pain around my cock. 

Giving him a final squeeze and pulling out of his mouth, I patted his head gently. 

“Get cleaned up and back to your studies, Richard.  You’ll be retaking the test next week.”