Date: Thu, 11 Sep 2008 21:45:47 +0000
From: A. B. <wildcard100@hotmail.com>
Subject: Jackies' New School

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This story is a work of fiction
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I was 12 years old and my parents were sick of me. Oh, they loved me well
enough I guess. They were just tired of seeing me come home beat up again
by the local bullies and having to go to the school and talk to the
Principal and argue with our neighbors to get them to keep their kids from
picking on me.

"If you'd stop being such a pussy and stand up to them...just once...take a
swing at one of them...maybe they'd leave you alone," my Dad said. "And I
don't mean that sissy slapping stuff. Didn't you learn anything in Tae Kwon
Do class?"

I just stared at the ground and shook my head. In truth, I hated Tae Kwon
Do. I hated just about every sport. The only "sport" I liked was swimming
and my middle school didn't have a swim team. I was hoping when I got to
High School I could try out but now it didn't look like I'd get the
chance. As I said, my parents were sick of me. They were sending me off to
a boardiing school. One, they said, that knew how to deal with "kids like
me".  I didn't hear anything else they said. The tears rolled down my
cheeks. My dad again called me a sissy and told me to stop crying but that
just made the tears come all the faster. All I could think of was how
horrible this place was going to be. I imagined it to be 100 times worse
than my own school. I had images of military academies and waking up at
5:30 am to march and hike and do parade drills. I imagined how much more
often I'd get beaten by "real boys".  I knew I was a sissy. I couldn't help
it though. I liked reading. I had a slight lisp that I couldn't get rid of
no matter how many speach thearpists my parents sent me to. I was thin and
not well muscled. I was scared of pain which made me frightened of being
pushed around and afraid to stand up for myself. My only friends seemed to
be girls and even some of them liked to push me down on the playground and
laugh at me.  But this was how I was and, as I said, I couldn't help it.

The day finally came and I was packed off to the boarding school. I won't
bore you with the details of my packing and pleading with my parents or of
the long drive and the introductions to the Headmistress. Its all pretty
much the standard stuff. The headmistress, Miss Stacy, was younger than I
expected (she looked to bein her early 30's) and less matronly. It turned
out that Papillon Academy wasn't a military school (thank goodness). It was
a simple boarding school. It consisted of a dorm, a building for the
classrooms, and a building that housed the gym/dining hall.  One other
building, a large old victorian looking house, served as the administration
building and housing for the teachers. In all, it was a lot smaller than I
envisioned.

Miss Stacy told us there were only 40 children at the school and 5
teachers, plus herself. My parents left as soon as they could, not even
bothering to help me get settled in in my dorm room. My room was pretty
spartan.  Two dressers, two beds, and a couple of night-stands.  The walls
were a pale peach color and not, as I had feared, some bare white-painted
cinderblock. My roommate hadn't shown up yet I was told, so I had my choice
of bed - a four poster I was surprised to notice.  I took the one closer to
the window.

Miss Stacey told me to come back to her office as soon as I'd put my things
away so in short order I was again in her office.  As I waited for her I
looked around. There were no photographs of her family. Her office was
comfortable looking and very feminine. A large overstuffed couch with a
pink flower pattern sat along one wall. Paintings of children, all girls I
noticed, adorned the walls. I looked closer at the paintings - there was a
ballerinia, a girl holding a basket of flowers, another of two girls on a
swing set (their skirt's flying up in the air) and one of a girl in a
yellow print sundress playing in a field withe some kittens. Not really my
type. Though I did think the ballerina looked very pretty and I thought I
could catch a glimpse of the panties of one of the girls on the swing
set. Strange, I thought to myself, that a painter would put that in a
panting.

Miss Stacy's desk was dark wood. It was bare except for a vase with some
flowers on the corner and a file that sat squarely in the middle. From the
paisely guest chair where I sat in front of the desk I could see my name on
the tab of the file.  Before I could look at anything more Miss Stacy came
in and sat down in the large red leather chair behind her desk. She opened
the file and flipped through it quickly as though she already knew what it
contained. I was nervous.  She didn't say anything as she flipped the
pages. Her mouth pursed. She shook her head once and I began to get ever
more scared. I couldn't help it. The emotions overwhelmed me and the tears
began to flow. When I sniffled Miss Stacy looked up from the file. She
looked at me like I was some disgusting bug that had crawled into her
office. "What are you crying for," she asked derisively.

I could only shake my head and shrug my shoulders.  Suddenly a sound like a
shot rang out and made me jump. She'd slammed her hand on the desk. I
looked up at her. "You will look at me when I speak to you and you will
answer me with a complete sentance when I ask you a question," she shouted.
"Is that clear?"

I nodded again, not trusting my own voice. She slapped the desk again, "IS
THAT CLEAR!

"Y-yes Ma'am"

"I'm not a Ma'am! You will address me as Headmistress or Mistress Stacy. Do
you understand?"

"Y-yes Headmistress."

"Do you know why you're hear Jackie?"

I was a bit taken aback by her use of the name Jackie. My name is Jack and
only the bullies at my old school had called me Jackie. "Baby Jackie. Sissy
Jackie. Jackie-wackie" Things like that. But the way she said it, as though
it were my regular name. Like a girl's name. There was just something
different about the way she said it.

"Because my parent's can't stand me anymore, Headmistress. They're sick of
me getting beat up all the time. I guess they want me to learn how to
become a man."

"Wrong. They've given up on you ever becoming a man Jackie. So they've sent
you to me to learn how to become a girl."  I looked at Miss Stacy with
confusion in my eyes and saw a wicked grin spread across her face as she
nodded. "The's right. You're a sissy. A pussy. You're worthless as a
man. And if you can't be a real man...then your only option is to become a
girl. Stand up!"

I did as instructed and stood. Miss Stacy also stood up and walked around
her desk, walking around behind me and to the front. Appraising me. Looking
me up and down. "Yes. You'll make a very pretty girl, Jackie." She moved
closer and ran her fingers through my hair. "You've got such lovely blond
hair. It'll be gorgeous once it grows out," she said. "And we'll get those
ears pierced tomorrow," she said as her fingers traced the outline of my
ears and pinched my earlobes.  I looked into her eyes, not believing what I
was hearing. Her smile grew even wider as she sensed my growing
comprehension and discomfort. "Oh yes my pretty little sissy Jackie.  Get
used to the idea. You're going to be a girl.  Right now, as we speak, all
your boy things are being thrown out. We have your sizes and when you get
backt o your room you'll find pretty panties and some training
bras. Dresses and stockings and garter belts and high heeled shoes and
strppy sandals," she giggled gleefully.

"B-but...but...I don't want to be a girl, Miss Stacy" I stammered, the
tears flowing yet again.

"Shut up!" she yelled.  "Look at you! You little faggot. You worthless
excuse of a boy. Crying there. You're pathtic. You're a little sissy fag.
Everyone knows it. All the kids at your old school knew it. You're parents
know it. And the only way you're ever going to be of any use to anyone is
as a pretty sissy girl.  Now strip."

I wasn't sure I heard her corretly and I just stood there. Suddenly she
slapped me across the face. "I said STRIP!"  The sting in my cheek felt
like fire and I cried even harder. I slowly pulled off my collared
t-shirt. "Move it," Miss Stacy shouted.  I unbuckeled my belt and unzipped
my fly and slid my jeans off. "Everything!"  I blushed a deep red as I
hooked my thumbs into my white jockeys and slid them down. I kicked off my
sneakers and pulled off my socks and stood before her naked. I was so
frightened that my little cock had shrivelled up as small as my balls.  I
tried to hide it with my hands and I suddenly felt a sting on my thigh as
Miss Stacy smacked me with a riding crop that seemed to have appeared out
of nowhere. "Drop your hands you little sissy."

She walked closer to me and roughly grabbed my little cock and balls at the
base with one hand. She squeezed firmly enough to make me wince but not so
hard as to cause me any real major pain. Then she tugged on them, again,
firmly but not so hard that I felt any real pain although I thought for a
second that she was going to pull them right off my body.  She snickered as
she fondled me and looked down at my little penis and balls in her hand.
She tugged them to the left and right and up and down inspecting them as
though looking at a piece of meat in the supermarket.

"Such a shame you have this pathetic little thing. You would have been so
much better off had you been born with a pretty pussy. Oh well...time for
your first lesson." She let me go and went back to her desk and opened a
drawer and pulled out a pair of red nylon panties. They were bikini cut
with lace trim around the waistband.  She tossed them to me and told me to
put them on. I looked at her but saw her slapping the riding crop into her
hand like some Nazi in an old World War II movie so I quickly complied and
slipped the panties up my legs, covering my tiny little sissy
cock. Unbidden, my bare little boycock reacted to the satiny feel of the
nylon and began to get hard, tenting out the frontof the panties. This did
not go unnoticed by Miss Stacy and she looked directly at my cocklett and
snickered. "Oh there's a suprise," she said sarcastically, "the sissy is
turned on by wearing girls panties. You'll be easier than I thought."

Miss Stacy pressed a button beneath her desk The door on the opposite side
of the room opened and in walked a man of about 25. He was naked from the
waist up and wore only a pair of jeans. He was well muscled with a flat
stomach and six-pack abs. He appeared to be over six feet tall and his arms
were strong from hard work, not bulked up merely from lifting weights. He
had a dark tan and only a light dusting of chest hair on his pectorals
leading down to a t"treasure trail" the disappeared below the waistband of
his jeans. His hair was cropped short and was a dark brown with eyes to
match.  His square chin and chiseled features were reminiscent of the
Adonis's that graced the covers of so many romance novels.

"This is Master Paul," Miss Stacy said. "He's your physical education
teacher." I blushed again, completely humiliated and embaressed to be
standing in front of this man wearing a pair of girl's panties.

"Ok you little wimp," Master Paul said, "We're going to start your phys ed
training right now. Get on your knees." I had expected him to tell me to do
push ups and began to get into position when I felt the sting of the riding
crop across my back. "He didn't tell you to lay down you silly girl," Miss
Stacy said. I looked up at them both in confusion. I was on my knees as
Master Paul moved in front of me and looked down at me.

"Here at Papillion Academy," he explained, "physical education is not about
excersize you stupid little twat.  Its about educating in the physical
aspects of being a girl. And the most important physical aspect of being a
girl, is learning how to please a man." While he spoke, Master Paul
unzipped his fly and pushed his pants down. He stood in front of me wearing
white jockey shorts and I could see his cock growing beneath them. My mouth
dropped open - whether from the shock at the size of the bulge in his
underwear, or the sudden understanding of what they expected me to do, I
didn't know.  But Master Paul said, "Good, keep that pussy mouth open like
that....you're going to need it."

He moved closer and told me to pull his cock out. I was about to refuse
when I heard the slap of the riding crop against Miss Stacy's hand and I
reached up to grip the waistband of Master Paul's underwear. My hands shook
as I I slowly lowered the underwear and his 8 inch cock sprang out and
slapped me in the face. He chuckled at that and said, "Good. Now take it in
your pretty little hands and stroke it a bit."

My hands were cold and his cock was hot. He moaned as I took that massive
tool in my little hand and slowly stroked the foreskin up and back. I was
crying as I realized what I was doing. I may have been a fag and a sissy,
but I never thought of myself as a homo. I liked girls and had gotten
turned on whever I caught a glimpse of a girl's panties under her skirt or
when I'd sneak a peek at my dad's Penthouse and Playboy magazines.  Yet,
here I was, wearing girl's panties and stroking a man's hard cock.  I'd
never touched another boy's cock before. It felt so different from my own
the few times I'd tried masterbating.  It felt silky and smooth and hard
and hot in my hand. I could see a drop of pre-cum oozing form his piss slit
and I was disgusted and humiliated with myself.

"C'mon," Miss Stacy said, "Get a move on. I have other students waiting."
Master Paul moved his hips forward so the tip of his cock brushhed against
my lips. The pre-cum wetting my lips as though applying lipstick.  "Open
wide my little sissy bitch," he said. My whole body was shaking. I did as I
was told and felt the head of his cock slip into my mouth. I closed my
eyes. Part of me wanted to throw up but another part of me felt an
acceptance of my fate. A willingness...no...a desire...to please Master
Paul. Perhaps it was fear of being hit with the riding crop. Or perhaps it
was a desire to get it over with as soon as possible. Or perhaps....there
was something else inside me that said, "Yes...this is what we were made
for. To please our man."  whatever it was, I felt my mouth stretched wide
open.  I felt more of his cock going inside my mouth. I couldn't help but
move my tongue around and I tasted his salty pre-cum. Master Paul began to
thrust his hips back and forth. Each time shoving more of his shaft into my
mouth and throat before pulling back just before I would gag.

"Cup my balls my little cocksucking cutie" he said. I did as I was told.
Rubbing his large nutsack with the palm of my hand. I almost threw up then,
whether from disgust or from his cock hitting the back of my throat. I was
only able to take about half of him inside and Miss Stacy commented on
this.

"That's ok," Master Paul said, "She'll get used to it. Most of them can't
take much more than that their first time. She's doing fine."  I looked up
into his eyes and he smiled down at me. His use of the pronoun "she" sent a
chill through me but when he smiled down at me I felt... pleasure?
Yes...pleasure. Pleasure at his compliment and at his obvious enjoyment of
my mouth. Pleasure at the fact that I was the one making him feel
good. Pleasure at being awarded his smile rather than the sting of that
bitch's riding crop. I wanted Master Paul's approval. For the first time in
I couldn't remember, someone...anyone....was giving me some small sign of
approval. My so-called friends never gave it to me, my parents never gave
it to me, and certainly Miss Stacy hadn't given it to me. Yet here was this
beautiful man. A real man. A manly man. Smiling at me and telling me I was
good. I was pleasing him. And, disgusted and humiliated though I was...deep
down I was also happy.

"Look at her go," I heard Miss Stacy giggle. "She's really getting into it,
the little slut."

"I told you she would," Master Paul said. The passion making his voice
throaty.

I caressed his balls harder. I began to bob my head in time with his
thrusts. I bathed his prick with my tongue and flicked the drops of pre-cum
ozzing out of his piss slit. I could smell his scent. Soap and salty musky
sweat. And I sucked. Ohhh....how I sucked. I sucked his cock. I was a
cocksucker. All the names that I'd ever been called came flooding back into
my head. Sissy cocksucking fag queer-boy sissy sissy cocksucker...yes yes
yessssss...I thought to myself...."yes...I'm a cocksucker....I'm a fag....I
don't care...just be nice to me...just don't hit me anymore...I'll do what
you want....I'll be a girl....I'll be a good girl...just be nice to me and
I'll be nice to you...I'll suck your cock and let you fuck my sissy
mouth..."

I sucked him hard and faster. He fucked my face with that big cock of
his. I sucked the soft spongy head and tried to get more of him down my
throat without gagging. I could feel it throb in my mouth and I felt his
balls tighten in my hand. Suddenly I head him goran and he grabbed the
sides of my head and thust his cock down my throat till my nose was buried
in his pubes. I almost choaked but then I felt him shooting his cum down my
thorat and in my mouth and I instinctively swallowed. I swallowed his cock
and that stopped the gagging. I could feel his hot sperm flowing down my
throat and into my belly and I swallowed some more. He pulled back and I
felt another load of creamy salty cum fill my mouth. I could taste the
sticky spunk on my tongue and again I almost gagged from the sudden
realization of what was happening and what I was doing. I was tasting
cum. I was swallowing and eating his load like a girl.

But then I heard Master Paul moaning, "Oh....yessssssss....Oh yeah baby
doll.....Oh that's so good....mmmmmmmmmm.....oh yeah baby....that was
great...."  The disgust faded and, with it, the nausea. He pulled out of my
mouth. Cum dripping down my chin. I looked up at him and he smiled down at
me. "That was great sweety," he said. and, despite myself, I smiled.