Date: Thu, 31 Jul 2003 18:04:53 -0500
From: J
Subject: Headmaster's Punishment & Reward

Headmaster's Punishment & Reward [M/b]
by Anonymous

DISCLAIMER: This is an entirely fictional story involving sexual contact
between an adult and underaged youth - obviously illegal in most countries.
This does not endorse sexual relations between adults and underaged youth,
but represents a long-time fantasy of mine.


I was terrified.  As a tenth grade student, fourteen years old, I'd never
before been sent to the headmaster's office for punishment -- an incredible
feat considering that most of my friends were 'regulars.'  Punishment at
this British-inspired, New England prep school for boys came in three
degrees.  Least dreadful was punishment by a dormitory supervisor, but only
for offenses committed in the dorms.  The supervisors were senior-aged
students, allowed to assign detentions, bathroom cleaning duty and writing
lines.

Teachers were permitted to punish students for minor offenses committed in
the classroom like talking or sending notes to a friend, but primarily for
homework and assignments which were incomplete.  They could assign
detentions, rewriting homework and assignments, and writing lines.

An appointment with the headmaster was reserved for only those students who
had committed the most 'heinous' offenses.  Failing an assignment was the
most frequent reason, however, other offenses included ditching class,
swearing at or talking back to a teacher, fighting with a fellow student,
smoking cigarettes or doing drugs, drinking alcohol, or gambling.  He held
absolute authority to punish in any way he deemed proper.  From my
companions, I had heard the headmaster favoured corporal punishment.  He
would rap boys' knuckles with a ruler, whip boys' hands with a strop, and
spank, paddle or cane boys' buttocks.  From the tears and welts I had
witnessed on other students, I realized the headmaster was devoted to his
duties.

I had often been punished by my dormitory supervisors and teachers.  Mostly,
I was caught talking after 'lights out' at 11:30 PM or was talking in class.
I was a pro at writing lines.  I learned that using a black pen, two
sheets of white paper, and carbon paper allowed me to complete two full
pages simultaneously!  I also had my fair share of detentions, often twice
or three times a week, for either half an hour or an hour.

But this time I was in too deep.  I had failed a history test, having
decided studying was not as fun as playing poker.  Though I hadn't been
caught gambling, I had failed my test.  The thrill of committing one offense
led me to actually commit another offense.

At 4:00 PM, when classes finished, the roll call of appointments with the
headmaster were read over the intercom system, so all could hear.  The
public shame was intended to act as a deterrent.  Having received my history
test results early in the day, during second period, I had an early
appointment.  I was expected to report to the headmaster's office at 4:45
PM.

At 4:40 PM, I arrived at the office, seating myself on the bench outside the
headmaster's door.  The secretary took my name and notified the headmaster I
was waiting.  I heard him say, "I'm nearly finished with Mr. Locke . . .
another five minutes."

I sat waiting.  For the past forty minutes, my roommates had been telling
tall tales of punishment.  Rick told about his paddling, and I recalled his
rosy red butt cheeks.  I joked that his ass was prettier than mine, so
perhaps he wanted to go in my place.

"No way, Johnny.  Headmaster Baker will beat your cheeks, pound your mounds,
hit where you sit!"  Rick laughed hysterically.

I replied, "Thanks, Rick.  You're an inspiration because you make it sound
fun.  Have you considered a career in advertising?"  Then I asked him to
leave me alone to prepare to meet 'Ass-breaker Baker', as we had nicknamed
the headmaster.

The secretary pulled me out of my day-dreaming, "Headmaster Baker called you
in."  Indeed, my classmate Mr. Locke -- Paul -- stood just outside the open
door with tear stains on his cheeks and puffy eyes from crying.

As I approached, he whispered, "Good luck, Johnny.  I think he's in a bad
mood."

"Thanks, Paul.  How'd you get it?"

"Paddle," he whimpered.  "Twelve times."  He limped away.

I heard the headmaster's deep voice call out impatiently, "Mr. Hogan, I'm
waiting!"

I hurried into the office, closed the door gently, and stood stiffly in
front of the impressive, antique mahogany desk.  I stared at the floor, more
out of fear than shame, noting the faded, thread-bare Persian rug.  To my
left, I could see the shelf of which I had been warned.  The instruments
were laid out in order: rulers, strops, paddles and canes; from smallest and
lightest to biggest and heaviest.  I only saw the choice as one of redness
or bruises or welts or open wounds . . . of pain or more pain.  I was
completely unaccustomed to spankings, as my parents had clear objections to
corporal punishment.

"Please look directly at me, Mr. Hogan."

The headmaster sat behind his desk, in an majestic, throne-like leather
chair.  He sat at attention, his back rigid, wearing a formal three-piece
tweed suit.  He was a little past middle-aged, perhaps in his mid-fifties.
Gray hair slowly replaced the black hair of his youth, and his eyebrows were
thick and bushy.  Small, oval eyeglasses rested on his thin, piercing nose,
framing the penetrating gaze of his hazel-green eyes.

"Would you care to explain why you are here?"

"Yes, sir.  I failed my history test."

"How unfortunate.  Having reviewed your file, Mr. Hogan, I note you have an
immaculate record with satisfactory grades and agreeable comments by your
teachers.  In fact, I've never before enjoyed your company.  How do you
explain it?"

I was nervous, searching for words, "I guess I became careless, sir.  I felt
too confident."

"Well, Mr. Hogan, I will have to adjust your attitude, eliminate your
carelessness.  I will explain two things because you have never before been
sent to my office.  First, I do not take pleasure in punishing naughty boys,
as all your classmates assume.  I do this as one of many duties, hoping that
no such offenses be committed.  Hence, when I finish, I will remind you to
avoid any and all offenses.  Do you understand?"

"Yes, sir," I responded.

Headmaster Baker continued, "Second, as this is your first visit, any
spanking of your buttocks will be by hand, as I reserve more severe
punishments for habitual visitors."

"Thank you, sir."  I shuddered, knowing that even that 'minor' punishment
would sting my sensitive backside.

"Let's finish our business, shall we?  I have decided that failing your
history test is punishable twofold.  You will have to rewrite that test,
achieving a passing grade.  But, for the moment, I will deliver twenty-five
blows on your bared buttocks as a reminder of your misdeed."

"Yes, sir."  I could now feel a stirring in my loins.  I was developing an
erection, as usual, at a most inappropriate time, like when I changed for
gym or saw the results of Headmaster Baker's punishment of my friends who
let anyone see their fleshy asses as proof of their 'bravery.'  Rick even
let everyone touch his painful posterior, enjoying the sensation of the cool
hands.

"Drop your pants, Mr. Hogan."  I did as he demanded, fumbling with my zipper
due to my nervousness.  I stood only in my dress shirt and boxer shorts,
with my pants around my ankles.

"Now drop your boxers."  I gulped, repressing my apprehension.  Hooking my
fingers in the waistband, I slowly pushed down my only protection, stooping
to the floor.  When I stood straight, the headmaster would see my four-inch
prick and my hairless, wrinkled ball-sack, as I had only recently hit
puberty . . . but what could I do?  Nothing.

As I stood, I realized Headmaster Baker was gazing at my crotch.  "Please
come around my desk."  I did, waddling with my pants and boxers around my
ankles, and the headmaster rolled his chair backward, and turned towards his
left.  I saw that his pants constricted a substantial mound.  But, in my
innocence, I assumed that was just his full-grown, limp manhood.

Gently, Headmaster Baker reached out, pulled me to his right, and directed
me to lay across his lap.  After I bent over, he grabbed my right hip,
holding me tightly in place against his body.  I could now feel his erection
poking my left hip, realizing he was stimulated by this too!

Before the spanking commenced, the headmaster lifted the tail of my shirt to
completely expose my smooth, rounded buttocks.  I felt the headmaster's hand
resting on my buttocks.  He then began to rub gently in a circular motion.
It felt strange, but pleasurable.

"Sir?" I asked, wanting to get underway with my punishment.

"Have patience, Mr Hogan," he whispered, as if in a trance.  I felt his
finger probing between my butt cheeks, slowly and deliberately, until he
found my asshole.  He touched it, making my body jump reflexively.  He
withdrew his finger.

"Ready?" he half-asked and half-warned.

"Yes, sir," I croaked, my eyes shut to block out the pain.

Immediately, the headmaster began, delivering blow after blow, alternating
his blows: right, then left.  He was slow, allowing himself time to raise
his hand, aim carefully, then strike with maximum force.  The first few
blows hurt greatly.  I was breathing deeply, as the impact of the spanking
took me by surprise, knocking the wind out of me.

Tears flowed freely by the fifteenth blow, as I felt heat radiating from my
buttocks, a result of overlapping blows.  My head, drooping down, was
flooded with blood which clouded my thoughts.  The pounding on my behind,
ground my hard-on against the headmaster's lap, introducing an element of
pleasure to this intentional injury.

As the last blows were dealt, my body sagged like a dead weight on the
headmaster.  I sobbed loudly, like a newborn incapable of expressing wants,
needs or discomfort in any other way.  My backside was throbbing.  My heart
pumped fresh blood to heal my tender buttocks and to maintain the stiffness
of my cock.

Finally, Headmaster Baker stopped, having dealt all twenty-five blows.  His
hand rested on my buttocks, as it had before the spanking commenced.  After
a minute of silence, the headmaster spoke softly, "Mr. Hogan?"

"Yes, sir," I choked.

Again, the headmaster rubbed my smooth, rounded butt cheeks.  This time,
however, I was more responsive to the stimulation -- a mixture of soreness
and satisfaction.  I groaned, humping the headmaster's leg, feeling the need
to ease the escalating tension in my groin.  Again, I felt the headmaster's
finger prodding at my asshole, and again, I felt the headmaster's prick
jabbing my left hip.

The headmaster whispered, his throat dry from exhilaration.  "Please stand,
Mr. Hogan."  I felt his hands clutch both my hips, and gently help me up.
Accidentally, my left hand on his right thigh slipped, pushing against his
erection, confirming the headmaster's sexual stimulation.  I stood next to
the headmaster, my dick nearly parallel with the headmaster's gaze.

"Mr. Hogan, you seem to have a . . . problem."

"Sir, may I return to my dormitory to relieve myself?"

I was fully expecting the headmaster to consent.  Instead, he replied, "No,
Mr. Hogan," as he stood up from his chair.  "First your going to relieve
me."

"Sir, am I not finished with my punishment?"

"Yes.  Now get on your knees," he commanded.

"Sir?"  I  asked innocently, not knowing what he intended.

"Now!" he hissed, increasingly impatient.

I did as he demanded out of fear, not curiosity, awkwardly kneeling down
because my pants and boxers were still around my ankles.  I said nothing
further, realizing that any protest would only invite further discipline.  I
had no desire to get in trouble, and did not understand I could lodge a
complaint.

The headmaster was breathing heavily, muttering about what a gorgeous lad he
had found.  He hurriedly unhitched his belt and unzipped his pants, and I
realized what he intended.  He pushed his pants to the floor and I laid my
eyes on the huge rod in his boxer shorts, tenting out the material.  There
was a moist spot on his shorts resulting from his dream about this moment.

Though he was married, with three children, Headmaster Baker had felt
increasingly attracted to the young lads who shuffled in and out of his
office for their punishments.  When he began in this post, all punishments
were just simple detentions.  But, within a year or two, he had suggested to
the Board of Directors that traditional corporal punishment should return to
this private, British-style boys preparatory school.  He pleaded with them,
asking, "How else can we teach these boys honour, respect and, most
important, discipline?"  The Board of Directors agreed, reinstating the
headmaster's right to administer corporal punishment.

Without further hesitation, the headmaster directed me to pull his boxers
down to his ankles.  I did, and was faced with his enormous erection.  At
the time, when my own hard-on was only four inches long, the headmaster's
seven inches was astonishing.  I noticed the headmaster had been circumsized
neatly, and I admired the thick pubic hair at the base of his cock which
also covered his low-hanging, swollen ball-sack.

"Lick it," the headmaster ordered.

I felt dreadfully nervous, my heart pounding, my prick painfully stiff from
excitement.  I wrapped my hand around the base of the headmaster's throbbing
erection, pulling it downward a little, into a horizontal position.  Slowly,
I leaned my head forward, as the headmaster watched wide-eyed, lasciviously.
  The first contact was heavenly bliss for Headmaster Baker.

I was surprised that the skin was as soft in my mouth as it had felt in my
hand.  The scent of masculinity and virility, wafted from the headmaster's
crotch, filled my nose, drove me closer to the edge.  There was a drop of
pre-ejaculate in the slit which I tasted.  I enjoyed the warmth and the
slick sweetness.  I slowly enveloped the knob of the headmaster's cock.  I
proceeded to envelop more, another inch, of this manly erection.

Meanwhile, Headmaster Baker had closed his eyes, feeling the hot, tight lips
and tongue of this angelic lad slowly engulfing his dick.  A high voltage
energy wave seemed to surge from his head to toes, outward from his crotch.
His skin was dotted with goose-bumps, and the hairs on the back of his neck
stood on end, as he became increasingly sensitive to this physical
stimulation.

"More," the headmaster hissed through his clenched teeth.  He thrust his
hips forward, forcing another inch into my mouth . . . then another inch.
At last, I felt the knob resting against the back of my throat.  (I noticed
there were still two more inches of penis to the base, but five inches was
all I could tolerate.)  Breathing through my nose, I began to bob my head
back and forth.

The headmaster guided my head with his hands, as he began thrusting his hips
vigorously to meet my forward plunge.  This forced the last two inches into
my throat, making me gag, pressing my nose into the depths of his bushy
pubic hairs.  I tried to relax my throat, to stop myself from gagging.

With my hands free of Headmaster Baker's cock, which slid in and out of my
wide mouth, I grasped the headmaster's right ass cheek with my left hand.
This way, I was pulling him forward to increase the pace.  Also, to
intensify the effect of my sucking and his thrusting, I held and gently
massaged his enormous balls (which had been slapping my chin).

Headmaster Baker was loosing control quickly.  I could hear his ragged
breathing, sense a weakness in his knees, detect an urgency in the
escalating speed and power of his thrusts.  With no warning, except a
resonant, throaty moan of satisfaction and exertion, an orgasm assailed the
headmaster.

A viscous wad of cum spurt to the back of my throat.  I gulped it down in
anticipation of more, completely engulfing Headmaster Baker's prick by
burying my nose in the sweaty pubic bush.  I was rewarded with three, four,
five, even more globs which shot straight down my throat.  I withdrew from
the spent dick, licking the tip clean of one last drop of cum.

The headmaster leaned backward, collapsing into his leather easy chair.  His
breathing was laboured and his mind was dulled (or lulled) by the multitude
of pleasurable sensations which accompany a long-awaited orgasm.

I stood up, intending to hastily pull my boxers and pants up, however, I was
halted by the headmaster.  "Wait," he gasped, "I see we still have to solve
your problem."

"That's unnecessary, sir.  I shall return to my dormitory."

"No!  Come here."  He gestured for me to sit on his lap.

I waddled to him, my boxers and pants around my knees, and he helped me into
his lap.  I sat facing away from him, leaning back against his chest, with
his limp, wet prick between my butt cheeks and his arms around my waist.  He
gently fondled my ball-sack with his left hand.  I could feel the tightness
in my balls, and I desperately needed release.

The headmaster encircled my virgin cock with his right hand and leisurely
stroked in rhythm, up and down.  When a drop of precum formed on the tip, he
squeezed it onto his finger, putting that finger in his mouth.

"Mmmmm, Mr. Hogan . . . you taste sumptuous, like a sweet Burgundy or
sparkling Champagne."  He resumed masturbating my dick.  He began kissing
and licking my ear lobe, as he mumbled faint words of adoration.

My whole body shuddered in delight because of this erotic stimulation of
which I was certainly unaccustomed.  I felt hot, as my breathing became
erratic and my pulse increased.  I could sense the impending explosion of my
balls, as the headmaster pinched and twisted my smooth sack.  His soft
stroking became more firm: yanking upward, pounding downward.

I moaned, closing my eyes, dreaming of some other time and place, as my
orgasm approached.  I was nearly . . . nearly . . . at the edge.  "Ungh!"
My cum -- hot, slick and pearly white --streamed out of my cock-head.  I
thrashed about, as the headmaster embraced me tightly, confining my arms at
my sides.  The countless spurts formed a puddle just above my crotch and
below my navel.  The crashing waves of my orgasm subsided, leaving me
lethargic, incoherent and dazed.

Headmaster Baker asked, truly concerned, "Are you OK?"

"More than OK, sir!"  I gasped for air to clear my mind.

"Good!  Now let me taste that boy juice."  He swivelled me around on his
lap, so I lay across his lap, on my back.  My mid-section, with the pool of
my cum, was completely exposed.  The headmaster leaned forward, slurping up
my semen.

"Well, Mr. Hogan," the headmaster spoke loudly enough for his secretary
outside to hear, "I am satisfied that I have completed your punishment."  He
winked at me.

I smiled at Headmaster Baker, understanding what he expected.  I whined as
loudly as possible, "Yes, sir.  I'm sorry to have taken so much of your time
with my naughtiness."

Quickly, we both stood up and snatched up our boxers and pants.  We zipped,
buttoned and buckled.  I turned to leave, but the headmaster stopped me.  He
gripped my shoulders from behind, leaned forward, and whispered softly in my
ear, "Mr. Hogan, I never did this before, but I enjoyed it.  You really
should visit me more frequently.  But make a regular appointment instead of
being sent here for punishment!"

"Yes, sir!"