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Subject: {ASSM} New from Waldo - Schooldays - Part 1 of 2 (teen tg)
Date: Fri, 16 Jun 2000 16:10:26 -0400
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Schooldays
All rights reserved by Waldo (mellin6695@aol.com). This story may be
freely distristributed on the Internet, posted on Web or BBS sites
where access to this story is free and doesn't require a paid
membership. Request that any WebMaster or BBS Operator who posts
this story on their site, drop me an e-mail letting me know where
the story is posted. In return, anytime that anyone writes me
directly requesting a copy of this story or other stories that
I've written, I'll send them to your site.
This story as in most of my stories concerns a transgender theme. It
wasn't written to entertain prudish minds or children.
Schooldays
By Waldo
Chapter 1 - Home alone
I'll never forget March 7th. It started out as a normal morning with
my mother giving me my lunch money and telling me "to have a
good day at school." I farted around getting to the bus stop and
somehow missed the bus so I had to return home. By the time
that I happily skipped back home, Mom was gone to work and the
house was totally empty. Gee, an empty house, an algebra test
scheduled for second period that I hadn't studied for and I missed
the school bus. What should I do?
Like all good young men, I decided to take advantage of the
situation and to enjoy a day off from school. Mom would never
know that I was playing hooky and it would give me the chance to
do a couple of things that I wanted to do in one of those special
times when I was the only one home. I was busily doing my
favorite pastime within the privacy of my mother's bedroom when I
heard the click of the bedroom door opening. Started by the
sound, I turned to see my mother quietly standing in the doorway
looking at me.
I was caught. Not only was I caught playing hooky from school,
but I was also caught playing one of my private games. At that
moment, I seriously wanted to instantly die but I knew that I
couldn't be that lucky. Although her voice sounded relatively calm
when she asked me "Roy, what are you doing?", I could tell that I
was dead meat no matter what I answered. For a second, I
considered lying to her, then looking in the bedroom's full length
mirror at the way that I was dressed, I knew that I couldn't come
up with an acceptable lie that could explain my current
appearance.
After all, I was dressed in my mother's clothes in her bedroom.
Yeah, I was wearing her pink chiffon dress and white high heel
shoes. Underneath the dress, I had on one of her bras which was
padded with a couple of apples wrapped in my socks to create a
realistic jiggle within the bra when I walked. Also I had on my
mother's panties and was wearing her pantyhose around my legs.
Around my neck was the pearl necklace given to my mother by my
grandmother and I had a couple of miscellaneous pieces of jewelry
on my fingers and wrists such as the turquoise rings that my
mother wears when she goes out on a date. I also had on that old
brown "Mary Tyler Moore" wig that Mom keeps in her closet for
those emergencies when she awakens too late in the morning to fix
her hair. And my lips were heavily coated with some of her bright
red lipstick.
Yeah, I knew that I couldn't come up with a lie good enough to
explain my awkward appearance. So I told her the truth. Or at
least it was something that I was hoping that she would accept as
the truth. "Uh, you see, uh, it's not what you think Mom, uh, I
didn't, uh, you see they are having a school play and like none of
the girls wanted to participate. So I was seeing if I could look
convincing enough to play the female lead. Sort of a gag role, you
know. Uh, what are you doing back home?"
Yeah, we were having a school play but I had no intention of being
in the stupid play, much less of wearing a dress on a stage in front
of any of my jeering boorish classmates. But it was the best lie
that I could quickly come up with, under the stressful
circumstances.
"When you weren't present for the 8:15 morning report, the school
secretary called me to make sure that I was aware of your absence.
It's the third absence since Christmas. I came home to see why
you weren't in school. So you're thinking about applying for a
female role in a school play, are you?"
"Uh, yes. After all, you keep telling me that I need to be a little
more involved in school activities."
The sucking sound of her work shoes clacking against the bedroom
hard wooden floors pounded loud in my ears as she walked toward
me and then moved in a slow circle around me as she examined
me. I stood still as she walked around me, knowing that my knees
were trembling so hard that I was afraid that I was going to faint.
Stopping when she was standing in front of me, she smiled as she
critiqued me. "Not bad. With your lithe body, you're very passable.
Next year when your shoulders have broaden a little more, you
wouldn't be able to get away with it as easy then but I think that
you could convincingly play that girl's role now. What's the name
of the play?"
"Uh, I don't remember. I had decided just before you came home
that I probably won't even try out for it. After all, I need to spend
more time studying to improve my grades before I get involved in
any extra activities."
Putting her hands on my shoulder, she turned me so that I was
facing the full length mirror again. Standing behind me, she
stared over my shoulder at our images in the mirror. I was
surprised when she adjusted the bangs of the wig with her
fingertips as she looked at me in the mirror. For the first time, I
noticed the light coating of sweat on my forehead and that my
lower lip was trembling slightly.
"Too bad. School plays have a way of displaying talents that are
usually kept hidden. You know, you should have been born a girl.
You've always had the longest eyelashes and prettiest lips."
I felt the wave of red embarrassment burn through my face and I
didn't have to look at my face in the mirror to know that my cheeks
were blushing at her comment. I started to unbutton the dress to
take it off and Mom stopped me by putting her hands on my
shoulder and pushing me toward her makeup table. "When you
were just a wee, wee, wee little baby still within my belly, I
wondered if you were going to be a boy or girl. Back then, I wanted
to have a daughter so that I could have someone that I dressed up
and went shopping with as we talked silly girl talk to each other. I
was very happy when I discovered that you turned out to be a boy
but I've always wondered what it would be like to have a daughter.
Sit down for a moment."
"Uh mom, I just remembered that I've got an algebra test this
morning. If I change into my clothes quickly, you can drive me to
school in time so that I could probably still take it."
Her hands pressing against my shoulder guided me into the chair
at her makeup table. As she flicked the lights on so that it brightly
illuminated my face, I felt two different emotions. One emotion
was that I was scared and wanted to go rub the lipstick off and to
change into my normal clothes so that I could run to school to
escape this awkward situation. The second emotion was that I was
feeling aroused by my mother's unexpected cooperating attitude
over my unusual appearance.
"The school's already marked you absent for today and I took
annual leave to come home to see why you weren't in school. So
we're both here. We have the same interests where we want you to
participate in school activities and you're already dressed in my
clothes. This will just take a minute to give you some professional
help and then we can both see what you would like if you had been
born as a girl. Then you can make up your mind about trying out
for that role in the school play."
I opened my mouth to politely turn down her suggestion but never
got the chance as she began removing the lipstick from my lips
with some tissues. "Roy, too much lipstick makes anyone look like
a drag queen. Let's take this off and I'll do it right. Now shut up
and watch what I'm doing. You will have to know how to correctly
do this if you're serious about trying out for that part. Putting on
your makeup so that you look more realistic can help give you a
girlish attitude so that you appear more natural and relaxed."
As my mother's hand kept mashing against my mouth to remove
the lipstick, I wanted to shout. I wanted to scream to release the
mixed joy and terror that I was feeling from her calm reaction to
finding me wearing her clothes.
I didn't say anything and just stared at my face in the mirror as
she applied foundation to my face covering up my couple of pock
scars. Then the softness of her fingertips spreading the blush over
my cheeks created rosy cheekbones, blended highlights and soft
shadows that totally changed the shape of my face making it softer
and more feminine. I had to shut my eyes as she applied eyeliner
and mascara although she described everything that she was doing
as she did it. But as she worked on one eye, I would open the other
eye to watch the way that she changed the total look of my face
with her skillful application of makeup.
In less than three minutes, she changed my face so much that I
didn't even recognize myself. Instead of an acne-faced boy's face, I
now had a realistic looking girl's face. A beautiful girl's face. A
gorgeous girl's face. All right, I was slightly biased but my face did
look pretty with the makeup creating cheekbones and highlighting
my eyes.
Using some small scissors, she slightly thinned my eyebrows
giving me a Brooke Shields type look so that they weren't so
heavily thick but at the same time weren't so thin that I would be
embarrassed later by my fellow classmates. After she applied the
lipstick and had me blot it on a tissue, she picked up a brush and
began working on the hair.
As she teased the wig and made it look a little more natural, I
stared at my new face in the mirror. I couldn't believe the
difference that a little correctly applied makeup made in my
appearance. I was beautiful. I looked just like a real girl.
I was memorizing everything about my new look when I was
startled by the strong smell of perfume. My mother smeared some
of her perfume on my neck while she commented. "Seeing as how
you aren't going to school today, we might as well make this a total
experience for you. This is my favorite perfume that I wear only on
special occasions. How do you like it?"
I couldn't tell her how I really liked it. After all, how do tell your
mother that the wonderful delicate smell of her sexiest perfume on
your body was giving you an erection?
Yeah, I had an erection but couldn't do anything about it. I just
wished that Mom would leave the room for a second so that I could
adjust it within her borrowed panties so that it didn't feel so
uncomfortable. Knowing that I couldn't adjust it without attracting
her attention to it, I tried to ignore it.
So I just blurted the only thing that came to my mind. "Smells
peachy."
"Peachy? I hope not. This is supposed to invoke mental images in
a man's mind of wild passionate sex, not of some peach orchard."
My mother said the "sex" word to me. But I didn't have time to
think about her choice of words and rattled off a quick
explanation. "Uh, no. Peachy is just an expression. Peachy keen,
you know. The perfume has a smell that I can't really describe."
With one tug on my wrist, she pulled me to my feet and turned me
so that she was facing me. Standing in front of her while wearing
her borrowed high heels, I noticed that we were at eye level with
each other. She stared at me with a funny little quizzical smile on
her face as she examined my face. Winking at me as if to share a
secret, she laughed as if this was fun for her to dress me as a girl.
"I know what was missing. You need some ear rings. I know, my
small gold hoops would be perfect for you."
Leaving me alone for a moment, I watched her as she turned her
back to dig through her jewelry box. I used that moment of
distraction to tug at my erection and to arrange it within the
panties so that it was sticking straight up instead of out at an
awkward angle. By the time that she came back to me with the ear
rings, my groin looked more normal under her dress.
As soon as she clipped the earrings onto each of my ears, she
stepped back so that she was able to easily see my whole body and
whispered, "If I didn't know better, I would swear that you were a
real girl. How does it feel to be my beautiful daughter instead of
my gangly son?"
"Uh, I don't feel any different. After all, it's just clothes and a little
makeup. And I'm only doing it so that I can make up my mind
about trying out for that play."
Stepping toward me again, I was very surprised when her hand
grabbed one of my make-believe breasts and adjusted it as she
laughed. "This boob is lopsided. What do you have in there?"
"Apple. Apple inside a rolled-up sock."
"Well, you're going to have to frequently look at yourself in a mirror
to make sure that you're not lopsided again. Boobs are supposed
to be parallel, not horizontal. You sure do look nice."
"Thanks mom. Well, now that I see how I look as a girl, I don't
think that I'll try out for that play after all. I'm going to change
clothes and ....."
"Nonsense. I don't care whether you try out for that play or not,
but I don't want you to change clothes yet. I want to see what it's
like to have a daughter for a day. I want you to remain dressed
like that and to pretend to be a real girl all day long. I won't make
you wash dishes or do any woman chores, but I just want you to
pretend to be my little teenaged daughter today. Will you do that?
For me? Pretty please?"
I wanted to scream "YES" but tried to keep my voice flat and
monotone when I answered. "Uh, if you insist."
Clutching my hand tightly, she pulled me toward a blank wall. Her
bedroom has several pictures hanging on the wall but she had me
stand against a bare section of the wall. Stepping back from me,
she adopted her familiar pose where she stood with her left hand
supporting her right elbow and her right hand supporting her chin
as she studied the way that I looked. "I'd never noticed before how
much we look alike. I knew that you had my lips but you've also
got your father's nose. But with that wig and makeup on, you look
just like a younger version of me, Roy. Roy? That doesn't like
right for a pretty girl. Would you mind if I called you Tonya? That
was what I was going to name you if you had been born a girl.
Tonya Marie Duff was going to be your name. Instead you wound
up as Roy Wayne Duff simply because you had the cutest little
itsy-bitsy pee spout between your legs. Yes, you're going to be my
Tonya today."
I didn't know what to say. Fifteen minutes earlier, my life was
ending when I had looked up to see my mother unexpectedly
standing in the doorway. And now she was standing a few feet
away from me so that she could see her "new daughter" and she
was proudly calling me Tonya.
Moving to her bed, she sat down on it as she opened the
nightstand and removed a pack of cigarettes. After lighting one,
she looked at me still standing against the wall. I was still too
stunned to do anything but stand there like an idiot. Blowing a
small cloud of smoke, she further surprised me by speaking to me
in a girl-to-girl tone of voice similar to the one that my Aunt Cathy
uses with my Cousin Nancy. "Tonya, looking like a girl is only half
of the feminine mystique. The other half is creating an undeniable
image of being a girl. Girls stand differently than boys who only
know how to slouch and lean against walls. Girls use their body
language and constantly changing facial expressions to emphasize
their words. But before we get into that, let's start with the basics.
Girls certainly walk different. You're at the age where you've
noticed the way that they walk. Let's see you walk like a girl.
Walk toward the bathroom door."
The sound of my feet in my mother's high heeled shoes clicking on
the hard wooden floor sounded too loud to me as I walked. In the
silence of the bedroom, I also heard another sound. The
unmistakable sound of my mother's pantyhose around my legs
swishing as my thighs rubbed as I walked.
"No, Tonya. You look like you're a Bull Moose walking. Here,
watch me and walk behind me. Move your hips and arms the way
that I move mine."
I followed her five times across the bedroom before she was
satisfied with my walking style. "That's great. You're picking it up
very good. You're a natural in high heels."
I stopped myself from biting my lip as she hinted that she thought
that I adapted too quickly to walking in the high heels. I prayed
that she wouldn't ask me if I had ever dressed in her clothes
before.
My prayers were answered as she moved on to the next subject.
"Now, let's work on your facial expressions. Girls have very
animated expressions. They pay attention to whoever is speaking
by maintaining eye contact and using their eyebrows and lips to
encourage the speaker to open up more. And girls are very
expressive with their facial features when they talk. Tonya, tell me
what you did in school yesterday but pretend that you were also a
girl yesterday. I'm your mother and want to know about my
daughter's day in school."
I made something up. I told her about cooking class and having to
learn to bake bread. She made me go through the same story four
different times and each time, she corrected me. She was right
about how girls talk differently. The first time was just a simple
description of sticking some dough into an oven where I arched my
eyebrows a couple of times. The second time of repeating my make-
believe school day, I followed her corrections and gave a more in-
depth description of the recipe ingredients and threw in a lot of
body language and facial expressions. "Too much overkill" was her
comment and we tried again. This time, she talked back to me as if
we were two friends discussing the homework and I talked "my
friend through baking some bread in class". By the fourth time, I
feel more relaxed speaking girl talk and adding facial gestures and
slight hand movements to emphasize my words. Mom laughed that
I was getting it.
The next hour was just a continuation of my lessons in how to
pretend to be a girl. Mom would show me how to do something and
I would do it over and over until she was satisfied. Then she would
have me repeat the other lessons and tie them all together into one
smooth routine. By that time, I was able to walk into the room as if
I was a real teenage girl just coming home from school, greeting my
mother as if I hadn't seen her all day, and then describing my day
with appropriate facial expressions and body language while I
brushed my thick mane of hair and freshened my lipstick.
Then she began working on my voice. "Softer." "Say the sentence
again but giggle at the end." "Slightly higher tone and inflection in
your words." "Not laughing enough, Tonya, make your discussion
friendly and fun." "Put some personality into your words and
expressions." "Be a little silly sometimes. It's permitted for girls to
be silly." "Giggle more."
By the end of my lessons in basic posture and speaking, I was very
pleased with myself. I actually felt like a real girl. That's when
Mom scared me with something that I didn't expect.
"Stand against the wall again, dear. That's it. Now smile while I
take some Polaroid photographs of you, Tonya."
"Uh, mom. I don't think so. You've showed me what it's like to be
a girl and now I know that I know what it's like to be a girl, I don't
want to try out for that play. Let's not take any photographs."
"Nonsense, Tonya. Photographs will help us remember this day.
Years from now, we'll look at these old photographs and laugh
about what great fun we had today. Now stand over there and
smile. Look pretty, dear."
I couldn't talk her out of it. She made several photographs of me
and kept taking them as she made me walk around the room and
repeat some of the things that she had just taught me. Then we
examined the many photographs. I really liked the realistic way
that I looked in them but I couldn't tell her that.
Putting the camera away, she scared me with her next request. "I
see that it's almost eleven o'clock. Go check the mail."
ME GO OUTSIDE DRESSED LIKE THIS!!!!!!! No fucking way!
Two minutes later, my knees were shaking as I stepped out onto
the front porch. I lost another argument with my mother. She had
argued that it was impossible to recognize me, especially the way
that I was dressed and my face changed. If any of the neighbors
saw me, they would just think that I was a cute cousin.
My eyes darted right and left as I stood in the doorway and I didn't
see anyone. Remembering my mother's coaching to act positive
and to keep my head high, I tried to put just the right amount of
swing into my walk and to move my arms the way that Mom
taught me. Normally I get the mail by running down the sidewalk
as I pretend that I'm dribbling a basketball and I'm back within the
house in ten seconds. The tight fitting skirt, high heels and
mother's instructions to take many small steps resulted in a one
minute walk. Thankfully there was some junk mail in the mailbox
so that I didn't have to walk back empty handed. Having
something to hold in my hands made it easier to keep from
breaking into a mad run as I came back to the safety of the house.
As soon as I stepped inside, Mom grabbed me and hugged me as
she congratulated me. "Perfect. You were simply perfect. How did
it feel, Tonya?"
My heart was still beating a mile a minute and I tried to keep most
of the excitement out of my voice as I responded in my new soft
voice "Great. I just did as you told me."
Handing me one of her spare shoulder-strap purses, she picked up
her purse as she scared me with her new plan. "You did so great.
Now, it's time to go just a little further. You and I are going to walk
to the corner store and I'm going to buy me a pack of cigarettes. If
anyone looks at you, just smile. If they say something, answer
them but remember your lessons on talking like a girl."
"Buuuuuuuuuuuuuuuutttttttttttttttttttttttttt Mom?????"
Three minutes later Mom and I were standing on the corner
waiting for the light to change. I had made it the whole block so
far walking beside Mom. Then a car stopped in front of us and the
driver waved. My mom responded "Hi, Mrs. Jenkins."
Aghhh. The nosiest busybody on the block was looking at me
dressed like this. I wanted to pee in my panties. Then Mom
scared me even more. "Mrs. Jenkins, have you met Roy's cousin?
Tonya's from out of town and will be staying with us every once in
awhile for the next several months. Tonya, this is Mrs. Jenkins."
I put a fake smile on my face and tried to keep from grimacing as
the old battleaxe greeted me with her throaty old woman's warble.
"No, I haven't met your pretty niece yet. I could see by the strong
resemblance that she's definitely related to you. Welcome to our
neighborhood, Tonya. Oh, gotta go. The light's changing. Nice to
meet you, dear."
My heart was pounding so hard within my temples that I thought
it had somehow moved to my head. As the neighbor drove away,
my mother whispered. "If you can fool her, you can fool anyone. I
put some money in your purse. After I buy my cigarettes, I want
you to buy some candy from the clerk. Remember to look him in
the eye and to smile. He's going to flirt with you but he does that
with all girls."
I reluctantly followed Mom into the store. I could feel the clerk's
eyes on me as soon as I walked through the door. Following Mom's
directions, I went to the candy selection and pretended to be
making a selection. I didn't care what I bought. I just wanted to
get out of there. Mom told me to wait for my turn to go to the
counter until after she paid for her cigarettes and was standing
where she could watch me.
So I waited and tightly clinched my thighs together as added
insurance to keep from peeing in my panties because of my fright.
As soon as Mom was finished buying her cigarettes, I rushed to the
line with a pack of chewing gum. But a couple of construction
workers beat me to the counter with a six pack of beer and some
sandwiches. While the guy in the front of the line was taking more
time buying lottery tickets, his buddy turned around and "checked
me out."
Yeah, he checked me out. As if a pretty teenaged girl would be
interested in a man twenty years older than me, with a pot belly, a
ripped t-shirt, a two-day-old beard and a toothpick dangling from
his lips. I ignored his hard stares at me and pretended to be
interested in reading the headlines on some of those magazines. I
barely heard my Mom's voice when she unexpectedly asked me to
do something for her. "Here, Tonya. Purchase this for me."
Trying to keep from making eye contact with the man who was
staring at me so hard, I locked eyes with my mother and silently
begged permission to immediately leave the store. One glance at
her unwavering eyes and I knew that I had to continue or bear her
wrath. Looking at the box that she shoved into my hands, I felt my
heart stop when I saw the words "Junior Absorbent Tampax."
God, she did this to me on purpose. Dressed me up like a girl, put
me in front of a horny construction worker and made me hold a
box of Tampax. Is it possible to will yourself to die? I tried to die.
A second later when I was still alive, I knew that I had to do it or I
would somehow be revealed as a boy. Holding my head high, I
looked the construction worker in the eye as I stood with my
shoulders pulled back proudly as if I had real tits.
He surprised me by nodding "good day" and then turned around to
do his purchase. With his back turned to me, I looked at my
mother who gave me a wink. It was actually working. My
masquerade was working.
Continued in Part 2
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