The Story of Dawn - Part 1
by Dawn Moore
This is the first installments 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 now 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 even bought some outerwear and shoes. Often I would be 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. You see, I am 5' 8" tall and weigh about 145 lbs. My features are neither masculine nor feminine, and I never have had a problem passing. 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, but I never reciprocated, that is until now.
Let's fast forward to a year ago. I met a woman named Sandy here in NYC and we hit it off right away. She 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 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 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, Chanel #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 dress me 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 moths 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 about this crush she had on a man she worked with and 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 1st 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. Guys often would 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 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 in my 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 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 Secrets 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 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 midtown hotel.
Well, when I met Sandy on Friday, 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 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 backed my bags. When I came out of the shower, she had laid out the cutest little silk red 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 grey sweater to match. 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 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"….
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