How did I start dressing? Who can say, for sure, why anyone
really starts doing anything? I am sure, as deeply as this is
rooted in my personality it is a need not a desire, that it was
something very early on as an influence.
The earliest thing I can remember that is remotely close
to actual cross dressing is an incident that happened when I was
about 10, because when I was about 11 we moved out of the city and
into the suburbs, and I remember this being in our old apartment
in the city. I was a boy scout in the suburbs and I graduated from
cub scouts at 11 years old.
We lived in an old apartment in the city, and there were
no closets in the apartment at all. The apartment had only one
wardrobe cabinet that held my father's suits and my mother's
dresses, our coats hung on pegs by the front door. Most of our
clothes were in dressers or, in the case of out-of-season clothing,
in a trunk in the storage the building provided in the basement.
It was a constant struggle, those years in the apartment
that I remember, for storage space. My mother was constantly
going through clothes to find clothes that should be thrown away
because they were worn or no longer fit. One day, while helping
her pack up some thing's, she took a rubber girdle (This was the
50's) and put it in the box. I stared at the "garment" as she
called it, not knowing what it was, there was nothing like it
in with my clothes.
I was at that age where I was first noticing the difference
between girls and boys, I hadn't gotten around to checking out
their clothing.
My mother caught me looking at the girdle and held it up
for me to see. I remember asking her what it was and she tried
to explain it, but then said "Here, let me show you." and she
put it on me. The exact words said on what date, I don't remember,
but I do remember the incredible feel of that girdle on me.
She told me that women wore them for hours and I should see how
it felt to have to endure wearing such a thing. Endure? I
was in heaven!
My mother was small, and I large for my age, so it fit me
much as it would her. All through the day it hugged me and clung
in a very odd feeling way for a ten year old. I have since learned
the descriptive word is "erotic". When it was time for me to take
it off just before my father came home, I remember feeling sad.
That was the first time I remember any sort of cross dressing
and since I still remember it almost 40 years later, it made a deep
impression on me. For a long time it was the only dressing I did,
since I had no real opportunities for sartorial exploration.
When I became a teenager I started spending some weekends
with my mother's aunt who lived closer to the city. She was a fine
old lady, but diabetes had robbed her of her sight and limited her
walking. It was good for her to have company, my parents thought,
and it gave them some weekends to themselves. It gave me fine
opportunities to dressup, so I certainly didn't mind.
She lived in a nice two story house that had four bedrooms
and two bathrooms, a mansion back in those days. Actually it was
an old farmhouse and the fourth bedroom had been a den on the
first floor, but Aunt Anna couldn't handle the stairs, so it was
now her bedroom. I had the upper floors all to myself. I say
floors because in addition to the upper story of bedrooms, there
was the attic with all sorts of old trunks and such.
Aunt Anna used to brag to people how wonderful I was
for coming over to visit and doing her housecleaning on the
second floor. Little did she know I did it all dressed up in
clothes I had gathered together. It wasn't her grand-nephew
that helped her, it was her grand-niece.
I remember one time that she was supposed to be
napping and I ventured downstairs to get a drink of water
without first removing my feminine clothes, she suddenly
appeared in the kitchen and asked me to make her some
tea. I knew she was blind, but to be standing there in
a dress with makeup on my face, her looking straight at
me, it was very unsettling. But there was nothing to do
but to get the tea and then she asked me to sit and talk
to her as she drank it.
That was the first time I ever shared the company
of another person while dressed, even though she didn't
realize anything was amiss, especially not me being a miss!
It was quite intoxicating to be sitting there with my aunt
being all dressed up, and her acting perfectly normal since
she didn't have any idea that I was dressed other than in
my jeans.
It became my regular practice when I went to Aunt
Anna's from then on to go and do my "housework" so that
I could spend the rest of the time with my aunt, or at
least that was what I told her. True, I did do the
cleaning but only after getting "All prettied up" as
I thought of it. Then my aunt and her niece would spend
a nice visit. I even began sleeping in a nightgown instead
of the pajamas I brought with me.
One time my aunt did surprise me, however, she had
ordered pizza for dinner, so I had to take the pizza from
the man and pay him while dressed. I had no idea he was
coming, so when the bell rang I was surprised, my aunt
never had visitors. She smiled at me and said that she
decided to have a pizza party with me, a food that wasn't
really on her diet. My hands shaking, I paid the man, and
he just said "Thank you, miss." and left.
We sat down to our pizza and I began to eat it very
carefully, I didn't want to get any sauce on whoever's dress
I was wearing. I looked over at my glass and got a small
thrill from looking at the lipstick marks on the rim.
We had a lovely evening, and I went to bed in my favorite
nightgown. It was a lovely weekend.
This went on for some time, me dressing up, my
great aunt not knowing a thing. Then one day I came home
from school and my mom told me that Aunt Anna was in the
hospital, her diabetes finally got the better of her.
She had died in her sleep the night before. I cried
myself to sleep that night, and I have missed her ever since.
Shortly after Aunt Anna died, I entered high school.
I dressed up regularly through high school, since I got a regular
a baby sitting job for a couple my parents knew. I baby sat for
them every weekend through high school, a very nice job, since I
was basically paid to do my homework. Very nice, also, since the
wife was about my teenage size.
Exactly how it started, I don't now know. At some point, however, I
began trying on the wife's clothes. It felt good, and of course, there was the
"forbidden fruit" aspect of it. Over the years there were some very close
calls.
One outrageous night the couple had said they would be late, so I
really went all out. The kids were no problem, they always slept the night
through, once put to bed. With the promise of a long night ahead, I dressed
completely. I had on makeup, nail polish, hose and heels. God, how I loved
her heels. She wore size 10 heels, which fit me perfectly, and she had a
couple of pair of very tall heels, one red pair of sandals, one black pair of
CFMP's. Of course, on this night, I wore the Come Fuck Me Pumps.
I remember sitting in the living room, drinking a glass of wine,
admiring the red lipstick marks on the glass and the cigarette butts in the
ashtray. The sight of my stockinged legs jutting out of the bottom of the mini
skirt and the tight feel of the corset kept giving me a tightness in my
pantyhose. I smiled as I looked down at my femme body. The smile
disappeared as I saw the growing wet spot on the red miniskirt. Now I had
laundry to do!
I put the load in the washer, and while it washed, I took my makeup
off, and got the lipstick evidence of my perversion out of sight by washing
the wine glass and emptying the ashtray. While I switched the load to the
dryer, I straightened up the drawers where I had gotten the clothes in the first
place. The clothes were barely out of the dryer when I heard the car pull into
the driveway. I put the still warm clothes in the dresser and closet, praying
they wouldn't notice. As I closed the drawer, I noticed I still had red painted
fingernails!
Luckily, they were very tired from a long night, and I was clumsily able
to hide my nails as they paid me and I hurried home, thankful my parents
would be in bed already. I ran upstairs, as quietly as possible, and into the
bathroom I flew! It was as I was searching the cabinet under the sink that I
realized my mother didn't wear nail polish, we wouldn't have any remover!
I spent a very sleepless night wondering how I would deal with the
problem, and I left the house in the morning before my parents were even
awake. The only good thing going for me was that it was a holiday Monday,
or I would have to deal with this and going to school. I kept my hands in my
pockets as I went to the drug store and bought some nail polish remover. I
don't know if the clerk believed me when I mumbled something about a prank
played on me by my sister, but I knew one other thing. I was once again
incredibly excited. The fear/excitement adrenaline flowing through me was a
powerful feeling indeed.
Over the course of my high school years there were a lot of incidents of
cross dressing fun, but when I went into the military, I buried it. I buried
it deep. Two recruits were caught sharing mutual masturbation and the platoon
of goons I was in basic training with gave them a blanket party. Don't ask.
There were no balloons and no cake, suffice to say. They didn't enjoy the
party, and I didn't want one in my honor.
Thus ended my adolescent dressing experiences. There was a gap,
as I said, in there while I was in the military, and when I got out of the army,
I got married and settled down, but that starts the adult part.