The English Teacher
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The English Teacher free porn video
The English Teacher
By Katherine Day
(Copyright 2008 by Katherine Day)
Chapter One
To the students, I was known as Miss Enright, although all of my friends
called me "Katie." What virtually no one knew, my parents had called me
"Kevin."
Yes, that's right. I was Kevin until I was 22 years old, and then after
spending most of my childhood and early youth trying vainly to be a boy
and then I man, I began living as a woman. By the time I was 25 I had
legally changed my name to Katherine Marie Enright, been to Thailand for
sexual reassignment surgery, had hormone treatment, completed hair
removal and gained breast enhancement to make me a woman.
I had never been happier. My youth had been full of humiliations as I
had failed at all attempts to become manly; my body itself should have
been a giveaway to my true gender, being relatively tall, slender and
with arms and legs as pretty and untoned as runway model. Now I was the
woman I was meant to be.
Being nearly six feet tall, and with flowing light brown hair, I realized
that I was now a beautiful woman. Whenever I dressed up, I never failed
to find men's eyes following me; other women, I could tell, were jealous
of my now trim 135 pound figure and my slender, lovely legs. My breasts,
now barely contained in 36 C bras, and my cute behind added to my beauty.
Oh, this must sound so vain, but I was as much a beauty as a female as I
was a failure as a male.
I remember hearing a woman say in a loud whisper to her friend as I
passed: "Wait 'til she has a baby, she won't have such a figure."
I smiled at that knowing full well I'd never bear that baby or face the
fact of a tummy growing heavy due to child-bearing. I also cried a bit
inside, since I would have loved to have been pregnant and to bear a
child. Thus, I sadly knew, I still was not a total woman.
After my successful surgery, I returned to college, completing classes to
get a teaching degree, with English and Drama my specialties.
I considered myself lucky to get a teaching position at a high school in
a mid-sized Southern Illinois community. As far as anyone knew, I was
born and raised as Katherine Marie Enright, from Chicago. I was so happy
to begin my career as a stranger and a woman in this lovely, but aging
city.
I taught 11th grade English and composition and 12th grade English
Literature, with a specialty on Shakespeare. For a few extra dollars, I
was hired as assistant director for the school's drama department,
basically being in charge of costumes.
I vowed to live a life free of any romantic entanglements for a few
years, as I worked hard to establish my ability to teach and to become
more comfortable as a woman. The last thing I wanted was to find myself
in a loving embrace with a man and beginning a serious affair in which I
would eventually have to reveal my past.
I was pretty successful at staying chaste, having been able to rent a
small upper flat in an old house from a retired spinster teacher, Miss
Emily Sparks. She and I hit it off famously, and we two became great
partners, traveling to see Southern Illinois University drama
performances and concerts at Carbondale, and even going to St. Louis for
a weekend opera trip.
Thanks to Miss Sparks, I could easily refuse offers for dates, which came
fairly frequently until the disappointed male faculty members finally
gave up with the belief I was indeed a lesbian. The gym teacher, Mr.
Jacobson, tried all sorts of gimmicks to get me to go out with him, in
spite of him being married to a city meter maid. Finally, in disgust, he
said: "You know Katie. It's a shame you're wasting such beauty on trips
with Miss Sparks. Don't you like guys?"
I remember mumbling something to the effect that I had been hurt by men,
and wasn't ready to date. Besides, I said, Miss Sparks was a good friend
and companion.
Yet, the truth was I needed sex. I had left an affair with a male friend
which continued for a year after my surgery, and the orgasms I had
experienced were plenty and heavenly. Now, I self indulged myself when I
needed such sexual relief.
In the fall of the second year of my teaching, my eyes fell upon Paul
Norris, a 6 foot, muscular young man who played tight end on the school
football team. He was in my senior English Literature class, held the
last hour of the day. In the seating scheme, he was in the front row, to
the right of center.
What first impressed me about Paul was the interest he showed in my
class; usually the boys from the football team hated English, but Paul
seemed to pay attention and offer good comments in class discussion.
Of course, he had a lean, angular body, and in the warmth of early
September, his sculptured body seemed to fill out a tight tee shirt,
arousing my attention. I felt weak at times, and tried my best not to
look at him directly, afraid I might orgasm right there in front of the
whole class.
Soon, I am ashamed to say, I took to wearing short skirts or dresses, so
that when I'd lift my arm to write on the board, with my back to the
room, my dress would rise up, exposing the backs of my thighs and
sometimes even the top of my thigh high nylons, showing a hint of soft
inner thigh.
I hated myself for doing this. Here I was 30 years old, and I was
becoming enamored with a 17-year-old boy. Not only was it against all
standards of education and a violation of my teaching contract, but it
was immoral and wrong. Yet, I could not help myself; I was a woman with
needs.
On the Wednesday before Thanksgiving, my desires could no longer be
throttled. I wore a single piece red dress with a scooped bodice
displaying ample views of my rather fleshy cleavage. The dress was
midthigh in length, and I wore a pair of thigh-high nylons with an
elaborate lace trim. In fact, Mr. Jacobson, the leering gym teacher,
accused me of being a slut that day in a particularly nasty way in which
he wondered what other woman on the faculty I was trying to seduce as a
lesbian.
The object of my seduction was my lovely, sexy student, Paul. As class
ended that day, I asked Paul to stay after school for a bit, that if he
was to stay eligible for the team, he had to do something about his
grades. I wanted to give him special help.
"But Miss Enright," he said, in a mild objection. "I should get home."
"Now Paul, I know you don't have football practice tonight," I said.
"You never go right home. Now, I'd like you to stay just a few minutes.
OK?"
"OK, Miss Enright, I guess I can."
I knew he wouldn't protest much; after all I had seen him eyeing me all
semester. He had the softest, light blue eyes, and full lips. Despite
being an athlete, there was a gentle softness about him that was so
alluring. The truth was I was infatuated with Paul Norris like I had
never been with anyone in my life.
"Now Paul, I want you to write me one paragraph on Hamlet. Tell me why
you think Ophelia loved him so much."
"Oh, Miss Enright, that'll be so hard."
"Paul, we just finished studying that. You need to concentrate more on
your studies. You can use your book to refer to the scenes.
"You've got 15 minutes. I want you to practice writing in complete
sentences, not like it's an email message."
Paul sat at his desk, not eight-feet from me, as I busied myself at my
desk, alternately standing up, and leaning on an elbow on my desk,
raising one leg behind me, exposing my slender legs. Sometimes, I'd
shift so that he couldn't help but see my cleavage.
All the time, I knew he must be in pain, probably holding back a hardened
penis, as he tried mightily to work on his paper. Even though I did not
look directly at him, I could sense that he was squirming in his seat.
I was being so mean to him, and it was causing me to begin to feel
sensations as well. Might I orgasm here and now, I wondered.
"Time's up," I said after 15 minutes. "Come up here, and let me see what
you wrote."
"Oh, Miss Enright, I'll just hand it to you."
"No, come up to my desk," I said sternly, knowing that he must be
experiencing the king of all hardons.
I had pulled a chair up next to the desk for him, so that we'd be seated
almost thigh to thigh as I pretended to go over the paper.
He walked, halfway bent over, as he approached the desk, one hand holding
his paper in front of his crotch.
As he sat, I leaned toward him, my cleavage showing openly, as I read his
paper. It was surprisingly well-written, and his point was that Ophelia
was a love-starved girl because she was kept in the castle without
chances to meet any boys other than Hamlet. Thus, it occurred that she
was in love with him. "Girls are often hungry for love when they are
lonely," he wrote.
"This is well-written. It shows what you can do, Paul."
"Thank you." I could see Paul had a hand in his crotch area, and he was
rocking slightly back and forth.
"But this line about lonely girls wanting love, Paul. Do you believe
that?"
Paul hesitated. "I guess. It just seemed to fit here."
My dress had risen up on my thigh now, and I saw Paul looking at the lace
trimmed nylon stocking and the hint of white flesh.
"Do you think I am a lonely woman?" I asked on a sudden impulse.
"Oh no Miss Enright. How could you be lonely? You're so pretty."
I was now totally enraptured with this boy. I could see his pants were
bulging and he was trying to hide that sight with his hands. I took his
hand from his crotch area, and placed it under my dress onto the soft
flesh of my thigh.
I then unzipped his trousers, and placed my hand onto his hardening
penis.
"Oh, you're so big," I said to him, as my hand wrapped around his
throbbing bit of manhood.
His fingers had moved up to my vagina and were entering, as I began to
orgasm. I panted so heavily, and let out a tiny squeal. "Oh my god,
Paul," I whispered while desperately trying to hold back an orgasmatic
scream.
I was trying so hard to be quiet; you never knew who'd be wandering the
halls then. I was in ecstasy now, not thinking straight and with my free
hand found a wad of tissue and covered his throbbing penis to collect his
ejaculation which was sure to come.
"Oh Paul," I said, looking into his soft eyes. "You're so lovely."
And I kissed him, leaving his mouth only to moan in sweet excitement as
he came into my hands and onto the tissue. But the ejaculation was so
powerful, it still wetted his trousers.
He removed his hands from my crotch and we held each other tightly.
The moment was suddenly ended, when we heard Mr. Johns, the janitor
whistling in the hallway as he swept it down.
We cleaned ourselves up, and I told Paul he passed his English test.
I drove Paul home, and we did not touch anymore that day. We both vowed
to never speak of this again, since I would be fired for sure and he
might lose his chance at a football scholarship at Southern Illinois.
We both knew, however, this was only a beginning.
Chapter Two
As was often the custom with my landlady, Emily Sparks, the two of us
shared dinner that night after my episode with Paul. Emily enjoyed
cooking and it was easy to accept her invitation after a long day of
teaching. The truth was, of course, I was very lonely, living alone in
the upper floor of her duplex in this strange new community; being a
stranger to the town, and still being wary of developing deep
friendships, I filled my nights with correcting student papers, curled up
with a mystery or romance novel and wondering whether I'd ever have a
Prince Charming to fill my life.
Emily had in a few short months become a friend; often, I thought of her
as perhaps an elderly aunt or even as a mother. My real mother had died
the same year I began living fulltime as a woman; I had loved her, and
she had early on noticed my girlish tendencies and, while not enjoying
the fact that her son was so different had soon accepted it, and seemed
to enjoy having a daughter. I cried many times after her death, thinking
of the great times we could be having as mother and daughter had she not
died so unexpectedly of a heart attack.
After supper, Emily and I baked pies together, chattering mainly about
her teaching experiences and my trepidations at whether I'd ever become a
successful teacher. I loved cooking with Emily; she was cheerful and not
too precise a cook, which made for some interesting taste results. For
an old spinster retired teacher, Emily could be a barrel of laughs. The
fact was we usually had a manhattan cocktail before supper and a glass or
two of wine during the meal; maybe the slight buzz we two girl friends
got was the secret of our enjoyment.
"Tell me, Emily," I asked after we put the pies in the oven and were
sitting on kitchen stools sipping tea. "Did you ever wonder whether the
kids ever learned anything you taught them?"
"Always, always, my dear," she said patting my hand.
"Didn't that bother you? Make you wonder why you went into teaching?"
"Oh yes, but by then it was too late," she said. "In my case, it was
either teach school or marry Billy Jenkins and go back to the farm as his
wife."
"Well, being a farmer's wife doesn't sound bad," I said.
"Billy was 15 years older than me, and he seemed to be the only bachelor
around then. Besides, he smelled. The only way to get off the farm was
to go to the two-year normal school and get a teaching certificate.
Which I did, and a few years later got a four-year degree and here I
ended up."
I didn't know what to say. Emily, by all appearances, should have been a
sad, old lady, but she was spirited and intelligent and still full of
life. She must have had few men in her life, I guessed.
Emily must have sensed my thinking, interrupting the silence by
continuing:
"Don't feel sorry for me Katie. I've had a happy, full life. And every
so often, I'll see a former student of mine who will tell me how much she
enjoyed my teaching, or how I helped her find her way in life. You never
know dear."
"I guess," I said in agreement, adding quickly. "You seem very happy,
Emily, and right now you're the best friend I have in this town."
By then the pies were done and we removed them from the oven, the smell
of cooked crust wafting through the carpeting and ancient woodwork of her
100-year-old house.
"Emily, sometimes I feel the boys are there only to look at me. They're
eyeing me all the time."
"Well, Katie, you're about the prettiest sight there is to see in this
town. Certainly, you're the best looking teacher there."
I blushed with that; I had become a terribly vain women, always soaking
up praises to my beauty. In a sense, I could dress far more plainly and
probably not attract so much attention. I really believed that we
transgendered women tend to dress far more chic than genetic women do;
perhaps we had always envied women's clothes so much we went overboard
when we started wearing them.
I know I had just that morning dressed in my sexy way mainly to attract
the eyes of Paul; I knew he had been looking at me, and that he must have
found my slender legs most fetching. I think I must have in an effort
overcompensate for any remaining male motions acted in a most feminine
manner, perhaps even exuding a bit of sluttiness.
I had always had a soft girlish appearance, even when I was male, and I
presumed I must have exuded femininity, which pleased me tremendously.
My thoughts as we chatted in the kitchen often went to Paul, to the
dreams that I'd be in his arms, like the defenseless woman I was,
caressing his strong arms and legs.
"What are you thinking about, my dear?" Emily asked, interrupting my day-
dreams about Paul.
I didn't answer right away, but my thoughts moved to Emily herself, now,
as I imagined that she, too, must have been very pretty when she was
young; even now, in her early 70s she was a striking woman with curly
grey hair and a trim figure. Despite some varicose veins developing on
her legs, she still had lovely legs.
"I imagine the boys liked to look at you, too, Emily," I said.
She smiled. "Oh, I guess I was pretty enough, Katie, but I was never the
beauty you are."
I suppose I blushed. The truth was: I adored her and wanted her approval
in the worst way. Even though some four years had passed since my
surgery, I still wondered each day whether I would be "read," that is
being seen as a male who transitioned into womanhood. I don't know why
that persisted, since I had always acted and looked more like a girl from
childhood on. It pleased me to know that Emily, who knew me about as
well as anyone, never thought of me as anything but a woman.
That night, before I went to bed, I imagined Paul was waiting in my bed
for me; it was absurd, of course, but he felt to real now. I took a long
bubble bath, something I rarely did anymore, but I loved laying there,
thinking of Paul, and how excited he'd be, seeing me in the tub, slender
and soft and pink.
I even put a few drops of perfume on before I stepped into a pink, silky
chemise I had bought just the other day in expectation that some night I
could wear it for a handsome lover.
Was I not being ridiculous? Or, was it natural for a lonely woman to
dream so graphically of wooing a handsome man and of feeling his warm,
affectionate hands caressing her?
Oh, Katie, I told myself: you're so wrong to be so full of lust (yes
that was the right word, wasn't it? Can't women lust, too?). For being
with Paul, your student, you could be fired from your teaching job and
never be able to teach again; worst yet, you could be jailed. I relieved
my pain somewhat by doing what I had been doing almost nightly recently:
I used a device to induce an orgasm. Actually, I had several before I
feel asleep, still thinking of Paul.
The weather was mild that Thanksgiving weekend, and I was able to go
jogging each day. Friday was so warm I wore only a pair of sweat shorts,
short white socks, pink running shoes and a light tee-shirt. I tucked my
hair back thru the back of the baseball cap, tying it in a bob so that it
bounced as I ran.
"You look so cute today," Emily said as I left the house to begin my run
down the tree-lined boulevard.
I was never athletic, having been told numerous times as a kid, "you
throw like a girl," and "you run like a girl," which I did, of course. I
am no more athletic now, but I found my short two-mile jogs (sometimes
not much more than a fast walk) always therapeutic, helping to clear my
mind and bring comfort to the demons that often seemed to rule my soul.
The joy of the run, the fresh air blowing in your face was always so
restful; I often thought about nothing during those runs, other than
making sure I didn't stumble on the uneven sidewalks.
"Miss Enright," I was suddenly startled in my run by a familiar voice.
"Oh Paul, I didn't see you," I stopped, still maintaining my job by
running in place.
He was standing before me, having come from a side street. He too was
dressed in what appeared to be a running outfit, a pair of short shorts,
a white tee shirt and his New Balance running shoes. He had the most
well-developed thighs and strong calves. What a lovely young man!
Mostly, however, I saw his sweet light blue eyes and his full mouth.
Oh my God, I was infatuated with this boy!
"May I run along with you, Miss Enright?" the sweet lips asked.
"Errrr ... ah ... oh ... yes, of course. But I'm probably too slow for
you."
"Oh no. It's an honor to run with you, Miss Enright."
We began running down the sidewalk, and sometimes when the sidewalk
narrowed, Paul would hang back and let me run ahead; I imagined he was
looking at my behind and my legs. I hoped he liked what he saw.
We said little during the run, since these bits of exercise seemed to
always exhaust me so, and I had to concentrate on the run. Finally we
completed the loop and returned toward my home, stopping at a small
neighborhood park a block away. I found a bench and collapsed onto it,
Paul sitting next to me.
I was all sweated and I must have smelled badly. This embarrassed me so,
since I really wanted to have Paul see me as I was last night at bedtime,
all pink and soft and perfumed.
"I'm afraid I'm not much of a runner, Paul. Sorry to have slowed you
down."
"Oh Miss Enright, I enjoyed this so much."
I smiled. It was apparent this boy was as smitten with me and I was with
him. This was a dangerous situation.
"I wanted to run with you," he said. "In fact, I had seen you run this
way yesterday. I live just a few houses from that corner where you saw
me."
"Oh?"
"And I waited for you today, hoping you would come."
"Oh Paul, you shouldn't have done this."
"Miss Enright, please. I think you're so cool."
Oh, this was going all wrong. I wanted right now to place my sweaty body
next to him, and kiss his lovely lips.
"Paul, darling," I said, realizing I had used a term of endearment. "We
can't meet like this. Teachers do not have relationships with students."
He looked sad for a minute. I wanted to take back what I said, and tell
him that I wanted to love him and to be his woman.
Finally he smiled: "I know, Miss Enright. But I think we could friends,
at least."
"I guess so, Paul," I said.
"I could help you out with chores at your house," Paul said suddenly.
"Well, I don't have any need for that. I rent the upper flat from Miss
Sparks."
Paul smiled: "I know that."
"You do? How?"
"You told me when you drove me home the other night."
"Oh yes, so I did."
"Maybe Miss Sparks will need some help, like with leaf raking, snow
shoveling, lawn-mowing."
"Maybe she does," I said. "I'll check with her."
"Oh Miss Enright, you're so cool."
"Paul, I need to get going now. You go home and I'll see you Monday in
class."
"Can't I come home with you now? And we can see if Miss Sparks needs
help?"
"No, Paul. That can wait, and I can check with her and tell you Monday."
I started to get up to walk the block to my home, but Paul grabbed my
arm, saying: "You're so special Miss Enright."
"Paul, you and I better not get too involved here, you know that?"
"Oh Miss Enright, I guess you're right. I'll see you tomorrow when you
go out for your run."
I smiled as I jogged slowly up the block, knowing his eye were upon my
retreating form. It was so sweet being a woman, I realized.
(To be continued)
Charlize
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