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Simone's High School Adventure free porn video
Simone's high school adventure: by Simone Clark
I was a high school student in the mid-80s on the East Coast of the
United States. I love the fashions of the 80s, leather skirts, high
heels, dresses for the ladies and big hair. When I was in high school, I
was surrounded by teenage girls dressed in these clothes, and I
desperately wanted to be one of them. I am a cross-dresser, and have been
a cross-dresser since about age 12 when I first tried on my mother's
pantyhose. Being a teenager is hard enough, but being a cross-dressing
teenager is extremely difficult.
I was an average kid of average size, not too bulky like a football
player but not small and thin like a track star. I seemed to get along
well with just about everybody, and had friends in many of the standard
social groups. I was a happy kid, I had two parents that loved me and
took care of me and allowed me to grow at my own pace, in short,
everything a teenage boy could ask for. I dated occasionally, but I just
never really seemed to make a solid connection with any girl I went out
with. Of course, I was obsessed with their clothes, I loved watching the
girls walk in high heels I loved looking at their nylon clad legs going
up into a skirt or dress and how feminine and sexy they all looked. As I
said, I would have done anything to be able to dress like them in public.
One of my best friends was a girl named Elaine. She was bubbly and fun
and always up to go for a drive, go to the movies, or go out to eat as
friends. She had several male admirers who continually chased her
primarily due to her incredible body. She was a woman amongst girls, she
had a full chest, round, feminine hips and she dressed to accentuate the
gifts God gave her. Her favorite outfit, was a satin loose fitting,
leopard print blouse belted at the waist, black leather skirt, black
pantyhose in black high heel pumps. People often mistook her for a
substitute teacher due to her appearance. I considered myself lucky that
I was friends with her and attempted to spend as much time with her as I
possibly could. She was into bands like Siouxsie and the banshees, New
Order, Devo and other alternative bands of the day. My tastes are
similar, and I often shared my cassette tapes and albums with her. As I
hung out with her, I found my lust growing for her wonderful outfits. She
always seemed to be wearing high heels and a tight skirt or dress no
matter what the weather or temperature. I seen her in jeans a couple of
times, but I never saw her wear sneakers unless she was in gym class, it
was always pumps, boots, or some other feminine footwear.
One day she and I were at her house putting together cassettes for our
Walkmen and talking about issues of the day that teenagers felt were
important. The conversation got around to boys, girls, and dating and she
asked me who I liked in our class. I was in a tough spot, the wrong
answer given at this point in time could mean social isolation so I tried
to soft pedal the question and turn it back on her. She was too smart for
that dodge, and pressed me for a name. I finally relented, and named
Jenny McCloskey is my secret crush. This of course is not the truth,
because I did really like Elaine, but I was afraid that if she found out
about me and my tastes, it would be all over the school in a matter of
hours I would be socially doomed until I escaped my town.
Elaine said, "You know, when you try to bullshit me it calls our
friendship into question."
I was shocked at her response, and questioned her as to why she would
answer that way. Elaine then said, "We spent so much time together and
you don't even consider me one of those crushes?"
I knew I really screwed up, all along Elaine had liked me and never told
me, boy, I would never understand women (this is still true today). I
tried to repair the damage as best I could and agree with her that she
was in fact one of my central crushes. I don't think she believed me, so
I went out of my way to convince her that what I was saying was true. I
actually got on my knees, grabbed her hand and said, "Elaine, I do find
you to be very very attractive and I didn't think that I was in your
league, so I never acted on my desire for you, please forgive me."
She seemed satisfied with that answer but there was a strange look in her
eye, she said to me, "I always thought you were gay, I've noticed how you
looked at me when I wore certain clothes, and was wondering why you did
that. I thought you were one of those fashion queens I have to deal with
at Merry-Go-Round at the mall."
I assured her that I was not in fact gay, that I really liked women but I
also loved their clothes. I took a deep breath and confessed that I
wanted to dress in clothes similar to hers because I loved the way she
looked in them and I just had to know how they felt on my body. Elaine
just looked at me without mouth slightly open in a shocked expression. I
knew that this was the end of my friendship with Elaine I would soon be
dismissed from her home in my reputation at school would be ruined. Not
only that, my parents would find out about my tastes and I would be
ostracized for my family. At these thoughts, tears began to run down my
face. I took a gamble, and I lost. I was unsure how to proceed from here.
I began packing up my things for the inevitable dismissal from my former
dear friend's home.
Elaine asked, "What are you doing?" I explained to her that I would leave
and would never bother her again, but plead with her to take our past
friendship into consideration and not tell anybody about what I told her.
Elaine grabbed me by the shoulders, and hugged me tightly. It was my turn
to be in shock. I didn't know what was happening so I returned her
embrace and waited for the next shoe to drop. Elaine broke the embrace,
took me by the hand, and led me into her bedroom. I didn't know what was
going to happen next, but I knew it was going to be life-changing.
Once inside her room, she faced me and said, "If we are going to do this
right, you're going to have to follow every instruction I give you, do
you understand?"
I said, "Yes Elaine, whatever you say." And prepared myself for whatever
was coming.
Elaine told me take off my clothes to my underwear so she could see what
she had to work with. I follow her instructions, taking off my dirty
sneakers, socks, pants and shirt to reveal an everyday young man's
body..... not too muscular, not too skinny. Elaine walked a slow circle
around my frame touching my body in certain places and making noises to
herself. I was excited, embarrassed, scared and filled with anticipation
about what was going to happen.
Elaine stood in front of me and asked "what kind of outfit would you like
to put on?" I told her I absolutely loved her black leather skirt and
animal print blouse with the belt at the waist. I also confessed that
wanted to wear black pantyhose and put on a pair of her high heels if
they fit. Elaine appraised me once again and said that her clothes would
more than likely fit me, including the shoes. I was unbelievably excited,
here I was in one of my best friends bedrooms about to transform into a
woman for the first time. I could describe the feelings that were going
through me but I did know that all of the feelings were pleasurable.
Elaine said, "I just can't call you Jeff anymore, especially when you're
dressed as a girl, what is your favorite female name?"
I said, "I really like the name Simone, it sounds mysterious and sexy to
me."
Elaine said, "Simone it is then!"
Elaine directed me to sit down at her makeup table so she could begin my
feminization. She did not do any of the work herself, she introduced me
to each individual product, and demonstrated how to put on. Apparently, I
was a quick student and before I knew it my face had foundation on it I
was working on my eyes, applying eyeliner and shadow, along with a thick
coat of mascara for my eyelids. She showed me how to use blush, and
finally a heavy coat of lipstick for that 80s girl look that I so lusted
after. She left the room for moment and returned with a big wig that
would spill down my shoulders and give me a decided feminine appearance.
She then painted my nails a deep red and then directed me to blow on them
so that they would dry. Once my nails were dry Elaine said, "Let's get
your outfit on, I can't wait to see you in it."
She had me take off my underwear and handed me a pair of high leg panties
in cotton. I put on the new underwear and found it to be very
comfortable. She then handed me a brand-new pair of black Ultra Sense
pantyhose for my legs. For those of you who do not remember Ultra Sense
pantyhose, they were the most soft and comfortable pantyhose on the
market at the time, they came in great colors, and were relatively
inexpensive. It was a sad day for crossdressers like me when they
disappeared from the market. Elaine showed me how to put the pantyhose on
my legs being very careful not to run them. I followed her instructions,
but knew how to put on pantyhose already, so I humored her as she gave
her lesson.
Once my lower half was clad in beautiful nylon, she handed me a white
lacy bra and put two oranges and the cups to give me a set of breasts.
Elaine appraised me and said, "I think you're going to make a good-
looking girl Simone, are you interested in continuing."
I said, "Oh yes Elaine, I want to finish and be a girl for the afternoon,
thank you for helping me."
She then went to her closet, and pulled out the animal print blouse,
black leather skirt, wide patent leather belt, and her favorite pair of
black high heel pumps. She handed me the blouse which I put on. There was
some slight confusion as women dressed in a different direction so I had
trouble finding the buttons for a moment. Elaine giggled at my difficulty
and showed me how to button the blouse. Once button to my neck, Elaine
handed me the black leather skirt which I stepped into, buttoned and
zipped the back over my hips and let the blouse hang over the waistline
of the skirt. Elaine and handed me the wide belt which I buckled over the
blouse giving the illusion of an hourglass figure.
Elaine placed the high heels on the floor in front of me and said, "Step
into the shoes from behind, the nylons will do the rest."
I did as she said, and my feet made a slight "shoop" sound as they slid
into the leather shoes, suddenly I was much taller, and balanced in a
very strange way on the balls of my feet. I nearly fell over several
times as I stood there in Elaine's high heels but with a little bit of
practice in Elaine's encouraging, I was able to take my first tentative
steps in feminine shoes. After about 20 minutes of coaching, I was
walking like I was born in high heeled shoes. It was such an exhilarating
feeling that I almost passed out from the pleasure couple of times.
Elaine and had me sit on the couch and cross my legs in a feminine
fashion. I found it was very easy to do in my nylon clad calves rasped
together giving me yet another example of how women's clothes felt.
Elaine told me to wait where I was and announced that she was going to
change in disappeared into her bedroom. I sat and waited on the couch and
found myself turning my ankle as I saw other women do when wearing high
heels shoes in public. As I sat there, I took stock of my situation. I
could taste the lipstick on my lips smell a hint of perfume that was
spritzed on to me by Elaine, and enjoyed the feeling of the pantyhose
rubbing against the lining of the leather skirt. I shook my head slightly
enjoying the way the wig cascaded down my shoulders and slightly obscure
my vision from side to side. I then examined my new feminine nails,
painted bright red and shaped with a file to a decidedly feminine angle.
I heard Elaine emerge from the bedroom and walk down the hall. I heard
the tap of her high heeled shoes on the hardwood floor, and waited with
anticipation to see what she had dressed in. I was not disappointed,
Elaine stood in front of me in a black cotton dress with a diagonal
zipper that went from the hem to the shoulder, suntan pantyhose, and a
pair of leather knee-high boots with 4 inch heels and pointy toes. She
stated "well Simone what do you think", and a slow turn on the toes of
her boots. I told her that I loved her outfit and was extremely jealous
that she was wearing such lovely boots. Elaine did a small curtsy and
said, "Thank you Simone."
Elaine then said, "Come on sweetheart, we are going for a ride in my
mom's Corvette."
A white-hot bolt of fear struck me, I could not go outside in public
dressed like this, I knew I would be discovered in my life would be over.
Despite my protests, Elaine got me into the garage and seated in the
passenger seat of her mother's black Corvette. We drove around town for
about an hour, since it was mid afternoon nobody took too much notice of
us. I was extremely relieved upon arriving back to Elaine's house after
our little jaunt.
The afternoon wore on and I experienced many wonderful feminine feelings
surge through my body and mind, and never wanted to take these clothes
off. I knew some part of me had awakened fully and now needed the full
light of day in order to survive. Elaine also enjoyed herself coaching me
on how to walk, speak, and move like a young woman. I enjoyed her
coaching and fell fully into the role of a high school girl playing
dress-up with her friend. Before we knew it, night had fallen and was
getting toward 9 PM. I had to go home, but I didn't want to not after all
that happened to me on this very special day.
As I removed Elaine's outfit, I felt a great wave of sadness wash over
me. Elaine noticed this and hugged me and said, "you're such a beautiful
young girl Simone, you're always welcome here to try on anything you
like." I was overwhelmed by her generosity and you will be returning for
more high school adventures as Simone the budding young lady that was
born with the help of my dear friend Elaine.
We had a few other ventures before high school ended if you'd like to
hear about them please leave a comment for this story.
Dottie
- 27.10.2022
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