Sidedressing
- 4 years ago
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Dressing free porn video
Dressing
Janet L. Stickney
The inability to express oneself is one of the worst things I can think of.
Myself, I didn't know that boys were not supposed to wear dresses until I showed
up at the dinner table completely dressed as a girl. I was about 5 or 6 I guess.
I can remember my dad going ballistic, and right after dinner mom had me change
back into my own clothes while she told me it was wrong for boys to dress as
girls. After that I was always careful so as not to get caught whenever I
dressed up. I always thought I was beautiful, but then, I was always looking at
the ideal in the mirror rather than the reality. My name is Tim Grant, I'm
currently 5' 5" tall, weigh about 125 pounds, with green eyes with brown hair.
My mother was just five foot, Claire my sister 5' 2", and dad was 5'6". I sort
of fell in the middle, and didn't expect to get any taller. I knew I wanted to
dress as a girl as often as I could and by the time I was 15 and starting high
school, I was well aware of men who dressed as women. In fact I had found a lot
of sites on the Internet that catered to them, and had printed out a lot of
information, from how to make your own breastforms and padding to how to do
makeup and hair. Experimenting, I made some birdseed breastforms and had cut
some foam rubber into ovals to pad my hips and let my hair grow out until it was
shoulder length, all in preparation for my debut this coming Halloween. It was
the one time of the year I could dress as a girl and `get away' with it so to
speak, and I had planned for that night very carefully. Claire had moved to
college, but she had left behind a lot of clothes, and I had carefully tried on
every item, and now I had several complete outfits, including shoes. My biggest
downfall was hair. No matter how hard I tried I was never able to manage a truly
feminine hairstyle. I managed to get close, but I was always unhappy with the
results and usually put my hair in a ponytail.
As Halloween drew closer, I knew that I would have to confide in my mother
because there wasn't anyway around it, so one day right after school I told her
that I was going to the school Halloween party as a girl. To my surprise, she
asked me if I finally figured out how to be a girl! "What do you mean figure it
out?" "What I mean is have you figured out how to become a perfect young lady."
I was at a loss for words! "Tim, you cannot possibly believe that I don't know
about you dressing up in private do you?" She knew! I was dead! "If you want to
dress as a girl I insist that you let me help you get ready. Do you have
everything you need?" "I borrowed some of Claire's things mom, I have several
outfits." "Show me" Was all she said.
In my room I showed mom what I had selected to wear, all of it, and all she
said was "adequate"! "I have to go to the store on Saturday anyway, so why don't
we get you dressed and let me see what you look like, and if you need anything
we can get it then. I'll even do your hair for you." "Dad." "Won't be here all
weekend. Now plan on getting dressed right after breakfast On Saturday." It was
a very long two days as I wondered just what mom had in mind, but I was not
about to let this opportunity slip by, and on Friday night I made sure that I
didn't have one stray hair anywhere on my body. Right after breakfast mom and I
went to my room where I slipped on a pair of panties, then as she watched I used
the foam pads to make my hips rounder. I slipped on the pantybrief and reached
for the bra, but mom stopped me. "Lets do makeup first Tim." I walked into my
sister's room and sat at her vanity while reaching for the foundation. Mom sat
next to, and slightly behind me watching, but not saying anything as I smoothed
the liquid foundation evenly on my face. I started to reach for the eyeshadow,
but mom stopped me. "Let me show you something Tim." She dabbed at my face with
some loose powder, letting it set for a moment before she brushed away the
excess, leaving my skin looking smooth and soft, and all one color.
Mom watched as I added a bit of earth tone eyeshadow, then a soft plum over
that, highlighted with black eyeliner on both upper and lower lids. I used a
rose silk blusher on each cheek and was reaching for the lipstick when mom told
me to wait. She sprayed my hair with hairspray, and began to curl my hair with a
curling iron. As she worked I watched her carefully so I could do it myself if I
had to, or had the chance. She left my hair all curled up, telling me to finish
getting dressed. I slipped the bra on and added my birdseed breastforms to the
cups. I now had a full `A' cup. Sitting on the bed I slipped on some pantyhose,
then went to the closet to get the dress I had planned to wear to the party. "Oh
no, not that Tim. For shopping you'll want a skirt and blouse." "Shopping?" "Of
course! You'll have to try on anything we buy, and I'm sure that you would
rather look like a girl trying on clothes rather than a boy!" "But I thought. I
mean. what if someone sees me!" "Then they will see a pretty 15 year old girl!
Now find a skirt and blouse and lets finish getting you ready."
I selected a pleated green skirt and a white blouse with a round neck collar,
and as soon as I had them on mom finished brushing out my hair. I stepped into
the black flats and mom handed me a soft red lipstick. In the jewelry box I
found a pair of gold hoop earrings and slipped them into the holes in my ears
after I took out the studs I usually wore. Mom was grinning at me as she picked
up some perfume and gave me a spritz. "I think that will do it for now, except
for a name. I can't call you Tim now can I?" Mom wanted me to tell her my
deepest secret, and as much as I wanted to tell her, I was afraid! I was
standing in front of the mirror looking at someone else. It was me, but
different, like I was my own sister, and I was afraid to tell her the name I had
chosen for myself. "Tell me Tim; I'll bet it's a pretty name." "Gail." I had
blurted it out quickly, and mom smiled when she heard it. That's a very pretty
name! Find a purse Gail, and lets go shopping!" I was rooted to the spot until
she took my hand and led me out of my room, stopped and picked up her purse, and
continued out to the car.
I had never been outside the house dressed as a girl before and I was very
nervous as we drove down the street. She reprimanded me twice for slouching
down, and when we got to the mall she parked as far away from the doors as she
could, even though there were places closer. Before we got out of the car she
turned and looked at me. "You are a very pretty girl Gail, and going into the
mall is exactly what you need. If you act like a girl, walk like a girl, and
watch your mannerisms, nobody will know who you are. Actually I was counting on
some of your friends being here, because that way you'll have to be doing your
very best or be discovered." With that, she got out of the car and waited while
I did the same. Standing next to the car I felt a breeze run up my skirt and
held it down as mom just giggled. "Come on then Gail, we have a lot to do
today."
We went through the food court, and sure enough, standing right in the middle
were some kids I knew at school! I stayed close to mom and we walked right on
by, and they never gave me a second look, like they knew who I was! Out of
earshot, I mentioned it to mom and all she did was smile. I walked beside her as
she veered into a huge department store, and then into the lingerie shop. "We
should get you some bras and panties of your own Gail. We'll start with a half
dozen panties and two bras I think." Please note, she did not ask me, she told
me. I selected two bras I liked and some nylon panties, but she said cotton was
better, so I got the bras and cotton panties in assorted colors. "This party, is
it fancy?" "It's a Halloween party mom, not the prom." "A pity." "Huh?" "Oh,
never mind dear, I was just wondering, that's all. But you should have something
to wear that would help foster the illusion; why don't we go in here?" And in we
went, to a store that catered to weddings, proms, and so on. Almost all of the
girls in school bought their dresses here, and in fact two of them, Kelly and
Jessica were there!
All I could do was act as if I belonged there, and mom and I sorted through the
dresses until she found one she said was just perfect for me. Believe me, I was
nervous as hell when she took me into the changing area, which was essentially a
single huge room. I quickly put the dress on, but it didn't look very good on
me, and I took it off and convinced mom that we had to leave. She didn't like
it, but agreed when about five girls came in just as I was ready to leave.
"Maybe at Sares we can find something for you Gail, but you're simply have to
relax! You look fine!" I tried, and almost did relax once we got into Sares.
Once inside mom picked out a pink suit, a sheath style dress and a jumper for
me, plus several blouses before we left for the car. "When we get home I want
you to try on all of the clothes, especially the suit. Save that to last, and
wear the pink heels with it." I did as she asked, and the new bras made me look
a little more pert I guess, and all of the clothes fit me just fine. The suit
was unlike anything I had worn before. It had a short, straight skirt, which
hindered the way I walked. The jacket was shaped to accent a feminine waist and
only made me look better. I walked out to show mom, and dad was standing there!
He looked at me and I waited for him to erupt, like a volcano held in too long,
but he didn't! "Howard, this is Gail, and she will be staying with us for a few
days. She has a party to go to next Saturday, so we did a little shopping
today." Then he floored me. "You. look very nice Gail; are you going to dinner
with us tonight?" I looked at mom, and before I could answer she said "yes of
course she's going with us!"
Trisha
- 07.07.2022
- 21
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