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MY DAY AS ANGELA
I watched a talk show on television that reminded me about my
childhood experience. It was a Jenny Jones show entitled Honey,
spend a day in my heels! It was about wives and girlfriends
getting their guys to spend a day dressed as a girl and go
shopping or to work as a girl. Most of them went shopping for
different things but one guy had to spend the day working as a
waitress. As I said this reminds me of an incident that
occurred when I was sixteen. My sister and I were arguing back
and forth over whether or not it was harder being a boy or being
a girl. My argument was mainly that girls had it easier because
they had easy jobs, they never had to pay for anything when they
went on dates, all they had to do was look pretty. My eighteen
year old sister argued that boys never had to do housework or
work as a waitress like she was doing and put up with having
their butts pinched or their tits grabbed. Boys could go out
and play games all day and when they took a girl out, they may
have paid the money, but the girl had to pay a price too. She
had to go through all the hard work of looking beautiful for
him. She had to kiss and maybe more with him. Well, as you can
guess, this led us to a little competition and I was challenged
to spend a day as a girl.
Wearing her clothes would not be a problem as we were about
the same size and they fit me quite well, including her shoes.
The real challenge was learning to walk in heels and acting like
a girl. I had to learn to sit in a skirt without exposing
myself, how to use a ladies' room, and how to flirt as a woman.
I agreed to spend a Saturday as a girl and work at the
restaurant with my sister as a waitress, then go on a double
date Saturday night. I also agreed to let her do all the
transformation on Friday night. She had me shave my legs, chest
and underarms as well as put my longish hair up in curlers.
Once I was dressed she began teaching me how to act, walk and
sit as a girl. She deliberately had placed me in her shortest
skirt and her highest heels to teach me to master them, knowing
that I could handle all her other outfits with ease if I could
handle the worst scenario she could think of. I think the most
significant factor in this endeavor and the scariest for me was
that when she had me dressed, I did not look like a boy in drag,
I was a very pretty girl and could pass on the street in the
daylight as one. Even mother had to take a second look to make
sure it was me in the skirt and not one of my sister's
girlfriends. I made the best effort I could to learn all they
were teaching me about being a girl as I was determined to prove
to them that being a girl was not such a big deal and that being
a boy was indeed tougher. Although, I must admit that through
the dressing stage and lessons, I was beginning to have my
doubts. Mother decided she would also help my sister teach me a
few lessons about being a girl and decided to have a
mother-daughter talk with me about boys and sex. She also
decided that we were going to put some of the lessons to an
early test as she took my sister and I out to get an ice cream.
Since my hair was in curlers they decided that it would be more
appropriate for me to wear some slacks, but I would still wear
heels to walk in, but a little lower heel than what I had been
practicing in.
We had a nice drive to the ice cream stand, and I felt a
little self conscious as we stood in line at the counter to
order our ice creams. Surprisingly, noone pointed or stared
other than to notice me as a female and I did notice a couple
younger boys looking me and my sister over but not laughing or
knowing me as a boy. They even let out a whistle at us and
though It flustered me a bit, it was kind of nice to know that I
could be attractive to them. Mother noticed my blush and said
that being whistled at was part of being a girl and that if I
was spending more than a day as a girl I would have to get used
to it as I did appear to make a very pretty girl. I just
blushed a little more.
We ate our ice cream and returned home. I was then dressed
in one of my sister's baby doll pajama ensembles for the night.
They left the curlers in so I could see how uncomfortable a girl
remains in order to look beautiful to the world. The next
morning I was awoken and made to help out in the women's work
around the house. Mother had always believed in a separation
between men and women's roles, therefore I had always been
excused from doing the housework, but today I was one of the
girls and had to do my share. Once the work was done, I was
dressed for my day as a waitress and accompanied my sister to
the restaurant. I was introduced to the owner. He had been
told about our bet and was more than happy to have me work for
him, especially on his busiest day. I was given instructions on
the basics of being a waitress and just what I was to do. I
took a few orders with my sister before being assigned my own
set of tables to wait on for the rest of the day. It was kind
of fun and noone except the three of us knew I was a guy. I was
shocked and actually let out a little scream the first time one
of the male customers at the counter grabbed a piece of my butt
as I walked by him. I wasn't sure how to act or what to say, so
I just tried to recompose myself and continue on ignoring it.
It continued throughout the shift. I guess by the end of the
shift I had become immune to it and actually felt disappointed
if they didn't pinch me as I went by. I was quite tired as we
finished our shift and headed home. I jumped in the shower
thinking that the day was over, but was reminded as I stepped
out of the shower that I had a date to get ready for. I was
tired and she was having us go to dinner and out dancing.
I, not only had to get through the date but getting ready for
it was no piece of cake as I had to apply makeup, wear an
evening dress and heels, and add the appropriate accessories as
well as do my hair. A girl has a lot of work in preparing
herself. She coached me in getting ready but refused to help me
with doing any of the work. It took me several attempts to get
my makeup to look just right. The guys she had arranged the
dates with had no idea we were not sisters nor that I was not at
least eighteen years old. My sister had given me one of her
college IDs to use at the club entrance. We figured that they
would not notice that we had the same first name as well as the
last name, that they would mostly be looking for the date of
birth and even though they would be the same they would think of
us as twins. We looked close enough alike to pass as twins
anyway. The boys escorted us to their car and drove us to one
of the best restaurants in town. Dinner was simply delicious.
The guys were really nice guys. They were easy to talk to and
we had a lot of things in common. we were right about the night
club, and they let us all in without blinking an eye. The guy I
was with liked to dance and did not take no for an answer. I
felt like I was on the dance floor all night long. I was glad
when the night finally started winding down and the guys
suggested that we leave the club. They drove us to Sunset Lake
and found a secluded place to park. It was beautiful. I was
just glad that we remained in the car and I didn't have to go
walking around in the high heels again. The guys were gentlemen
and did not force themselves upon us. I did have to give in and
do some hugging and light kissing with my date, but that was as
far as he seemed to ask for on a first date. We stayed there
for an hour or two before going home. They walked us to the
door and gave us a kiss on the porch as they said goodnight.
Mother was waiting up for us when we came in and wanted to know
all the details of our date.
My sister did not leave out a single detail. I was asked
what I thought about being a girl now that I had spent a day as
one, and I admitted that I was going to be glad to go back to
being a boy. Being a girl is much harder and I'm glad I didn't
have to go through another day as one. I prefer the simpler
life of the male.
Sincerely,
Richard D. Jackson
"Angela"