MOTHERS DAUGHTERS CONNIE DAWN
- 3 years ago
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The Story Of Dawn - Part 1 free porn video
The Story of Dawn - Part 1
This is the first installment of my transition from part time cross
dresser, to the "woman of my dreams". For once in my life I have begun
to really enjoy the "gal" inside of me, and you know what, there are
many friends that I have that enjoy her as well...
Let me begin where most gals like me begin. First of all my name is
Dawn, although some of my friends call me Dee. Like most gals, I have
always felt the urge to dress up in silky lingerie and women's
clothing, and I have vivid memories of dressing up in my Mom's
lingerie and dresses way back in Junior High. At first I thought that
I might be "weird", but that didn't stop me. I felt oh so good when
dressed, and I managed to have some special times to myself, often. I
even remember coming home from school one day, while my parents were
still at work, and quickly dressing up in some of my Mom's sexier
lingerie. I then went downstairs and left the drapes open and
pretended to be looking for a book in the bookcase, all the while
hoping that I might catch some man's eye as he drove by. I guess you
could say that even back then I was somewhat of a "tease"...
Well, in my 20's and 30's I started to put together quite a collection
of clothing and lingerie. I learned how to do my makeup and bought
some outerwear and shoes. Often I would be away on a business trip and
plan to take a day off and dress in my hotel room for a day out
shopping and going to the movies. My, how I loved those special
days... I would go to the movies dressed up and rarely if ever would I
be read. I would love to go shopping at the mall, try on clothes, eat
lunch in a restaurant, visit the ladies room, etc., in short, do all
the things any other gal would do on her day off... Often I would get
comments from guys who would try to hit on me. I was flattered and
even a bit excited, but I never reciprocated, that is until now.
Let's fast forward to a year ago. I met a wonderful woman named Sandy
here in NYC and we hit it off right away. She always loved to wear
silky thongs and matching bras and garterbelts. Always in matching
sets... And, she had the best collection of stockings, which she would
wear all of the time. Even when we were in bed... She was definitely
my kind of gal, and I was sooooo thrilled!!!!! The sex was great and
we really became quite good friends, even though we both knew that we
were not truly in love with one another.
Well, one day we were just lounging around in bed in her apartment.
She was wearing a silky black babydoll nightgown with a satiny robe.
Underneath she had on a black thong with a matching garterbelt and
stockings. Out of the blue she asked me if I would wear some of her
panties for her. I was stunned! She said that she thought that I would
look very sexy in them and that she would be quite turned on by that.
Well, I of course said yes, and the next thing you know I was wearing
a very sexy pair of red silk thongs and a red thigh length silk gown.
She swooned over me and said that she was amazed at how feminine I
looked. Then she said that she thought my outfit needed stockings. So,
she ran to get me a garterbelt and stockings and she stood back and
watched me as I put them on. Without thinking, I rolled the stockings
up expertly, just as I did most nights at home when I was alone.
With one hand on her hips, and a smile on her face she said, "This
isn't the first time you have done this, is it?"
Well, I confessed right there and then about my long time interest in
crossdressing. She came up to me and gave me the biggest hug and told
me to relax.
The she said, "What a great weekend we are both in store for."
I sat on the bed while she went into the kitchen and returned with a
bottle of wine and 2 glasses.
"Let's just relax and have a real girl's weekend together." she said
as she poured the wine. "Now, tell me what to call you, when you are
dressed like this."
I had never really thought of a gal name for myself, but I blurted
out: "Dawn, or maybe just Dee, for short."
Well that weekend, we took bubble baths together, powdered each other,
painted each other's fingernails and toenails, and brushed each
other's hair. Like most girlfriends, we also experimented doing each
other's makeup. We watched movies in bed, and of course tried on lots
of different lingerie outfits (fortunately, we are the same size). We
laughed and giggled all through the day and night, and of course we
had fantastic sex while dressed in similar, sexy outfits. Oh, what a
weekend it was for both of us!
When it came time for the weekend to end, she made me wear some of her
panties and stockings under my guy clothes for my walk home. She said
that it was one of the best weekends she had ever had and that she
felt that she now had the best of both worlds. A best girlfriend with
a little something extra in her panties for her to play with!!!!
"Next weekend, Dee, I want to go to your place and see all of the
clothes you have there."
So we arranged for her to come over on the following Friday night.
Well, Friday came, and I answered the door to let her in. I was
dressed in one of my sexiest outfits. I had chosen to wear a sheer
black robe with a matching sheer black nightgown underneath. Of course
I was wearing stockings and heels, and a very sexy red corset with
matching thongs. I had done my makeup perfectly, and had brushed out
my long brown hair in a very feminine style. To top it off, I had
sprayed on some of my favorite perfume, Channel #5.
"My God, you are beautiful!" she exclaimed and gave me the biggest hug
and kiss as we closed the door.
That was the beginning of our weekend rituals, and we became closer
and closer each weekend, but still only as friends. Eventually, she
wanted to take Dee out and go shopping together. She would have me
dress in every day casual clothing for our excursions, but always with
the sexiest lingerie underneath. Often, guys would try to speak with
us and pick us up, but we just kept to ourselves, just as if we were 2
very close girlfriends, out for the day together. Gradually, I was
feeling more and more feminine, as by now I was spending all weekend
long, and every night dressed up as Dawn. And boy did I ever love it!
After about 6 months of this, we started to talk more intimately, and
eventually the talk gravitated to the subject of men. I guess this was
only natural, as I truly was identifying myself as a Dawn. She told me
in detail about this crush she had on a man she worked with. We
giggled like 2 schoolgirls and plotted how she might get him into her
bed. Then she suddenly asked me if I ever thought about going out with
a guy. I told her all about my experiences years ago, when men would
try to pick me up, and she became obviously quite turned on by this.
"God, I would love to be a fly on a wall when you go out on your first
date." she said.
Little did she know how soon that would be!
You see, the next week, I happened to be in one of the chat rooms that
I frequent. I had just taken a nice long bubble bath after work and
was relaxing in a silky floor length purple gown, panties and
stockings. This was my usual attire after work and what I always wore
to bed. Guys would always try to hit on me in the chatroom and often I
would play along and tease them with some sexy chat.
This time, a man by the name of Charles asked me to private chat with
him. I said sure, and we started to chat away. He told me that one
fantasy he had was to have a gal like me model lots of outfits for
him, so that he could choose which one I would wear out on a date with
him. He then said that he would love to take me shopping and would be
so turned on by knowing what lingerie I was wearing under my dress and
by watching me go into the changing room to try on clothes.
Apparently, the thought of our little "secret" that I had tucked in my
silky panties turned him on. His fantasies were so much like mine that
I started to get a stirring in my panties and a bit lightheaded. The
longer we chatted, the more I became infatuated with him, and for the
first time in my life I actually thought about meeting a man for a
date.
We chatted the rest of the week. It turned out that he was from
Brooklyn, and wanted very much for us to meet up. I told him that I
thought that would be nice, but that the first date would be strictly
to get to know one another. I suggested that we meet in a hotel room
some morning the next week and that we have a cup of coffee while I
model some outfits for him. He could then choose what he wanted me to
wear that day. After that he could take me out for lunch and then some
shopping. I told him that if he played his cards right maybe we would
end up in Victoria's Secret and he could join me in the dressing room
while I tried on some lingerie. I guess I was doing a little bit of
teasing, but I was getting very turned on by the thought of us being
together. Besides, he seemed to love the whole idea! We exchanged
pictures, and it turned out that he was just gorgeous. I gave him my
cell number and we chatted for a while, and he sounded ohhh so sexy,
but yet quite the gentleman! We agreed to meet the following Monday
morning in a hotel that I knew in the city.
Well, when I met Sandy on Friday, evening I told her all about my week
and the date that I had made with Charles for Monday. She was so
excited, that she started to run around my apartment, picking out
clothes for me to model for Charles. I swear she was more excited than
I... I made a reservation at a little boutique hotel that I know in
Chelsea for Sunday and Monday night. It turned out that they upgraded
me to a suite, as it was a quiet time of year. Sandy was also quite
busy. She made an appointment for me to get my haircut at her
hairdressers on Sunday afternoon; something I had never done dressed
as Dawn before. She also made sure to book me to get a manicure and a
pedicure, at the same time.
Saturday morning we awoke early and dressed casually (still with sexy
lingerie underneath, as always) for a trip to the outlet mall that was
outside of the city. We shopped all day, tried on tons of clothing
together in the dressing rooms, and found a couple of cute dresses,
some skirts and tops, new shoes, and of course some sexy new lingerie
outfits for me. We had so much fun! That night she was all over me as
soon as we walked in the door and said that she had to "drain me"
before my date so that my little clitty would not show under my
clothes. She knew just how excited I would be when I would meet
Charles on Monday!
Sunday morning we woke a little later than normal and just cuddled
together in our lingerie in bed. Around eleven she said "OK girl, it's
time to get ready for your big day!" She threw back the sheets and
told me to hop into the shower and shave myself clean while she packed
my bags. When I came out of the shower, she had laid out the cutest
little red silk thongs and bra outfit on the bed. Next to that was a
new package of gray opaque stay ups from Wolford. I asked her were all
of this had come from, and she said that they were a present from her.
I am such a lucky gal!!!! I dressed in them, and they felt oh so good.
She also had laid out an adorable little pleated black wool skirt and
a darling gray sweater to match. Next to the bed was a pair of black
leather calf high boots with 3" heels. Just perfect for my appointment
at her beauty parlor...
Just as I was putting the finishing touches on my daytime makeup, she
came out of the shower and quickly dressed in similar lingerie and
holdups and a beautiful, but simple jumper that I had never seen her
wear before. She grabbed a weekender roll bag, as well as a garment
bag that appeared to be just chock full of clothes. We threw on our
coats and grabbed our purses and we headed out the door. We were off
for the beauty parlor and then to the hotel. I knew that she was going
to stay the night with me in the hotel and then help me get ready for
Charles in the morning. There was no way I could keep her away...
Well, sweeties, be sure to check back for Chapter 2, "My First Date"
Mara
- 17.01.2022
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