Crystal's StorySite

This is an autobiographical account of the first time I went out as my alter ego.


My First Night Out

by SandraB


I had been a closeted crossdresser since I was a little boy. I remember sneaking into my mother's drawers and closet every chance that I could to try on her things. As a teenager, this became an obsession and the focal point of my fantasy life. I knew I was different from most teenage boys. Most of my friends, when they saw attractive girls, would comment about how hot they were and wondered aloud what it would be like to be with those girls. I looked at those same girls and wondered what it would be like to be them, to be that pretty, to receive so much attention from guys (and from jealous girls!).

When I was in college, I had no outlet for my secret obsession. I tried to bury it, but to no avail. Perhaps, it was a catalog, or something that would catch my eye at the mall, or even just the sight of a very attractive girl….something always seemed to make me dream of being that very special girl once again. And once again, my fantasies became more important to me than the realities of my life.

When at home on a school break, I discovered a weekly "alternative" newspaper. As I read through the classifieds, one jumped from the page and grabbed by attention. Her name was "Cleo" and she offered a makeover service for crossdressers. She even offered weekend packages, shopping, and nights on the town! My heart skipped at the thought and began to wonder if my fantasy life could in some small way, become a part of my reality.

I had a part-time job while at school to pay for "extras". I soon was saving every penny for my real makeover experience. When I finally had enough money and had finally gained enough courage…I made the call. She actually answered the phone and I stammered with the right words. It was as if she had been through this a million times. Cleo asked all the right questions and guided me into telling her all about myself. She was as sweet and kind as I could have ever hoped. We set up an appointment for me to receive my first makeover on a Saturday afternoon.

Cleo's home was a little hard to find. She lived in the suburbs of Atlanta in an area that had not yet been fully developed. Her home had a "country charm" to it and was warm and inviting. I nervously knocked on the door. I small, 50ish aged woman with an engaging smile opened the door and made me feel immediately at ease. She was as friendly in person as on the phone and we soon sat down for a nice chat.

Cleo asked me what my "femme" name was. In my fantasies, I had several names that I would alternate on a frequent basis. That night, I replied to her that my name was "Kristen". From that moment forward, she always called my Kristen. Oh, how I loved hearing my new name!

She took my back to her studio. There were closets of clothes, wigs, shoes, and a make-up table. I was in heaven! Cleo spent two hours with me doing my make-up (and teaching me how), changing clothes, swapping wigs. I had hoped that I could look like a real girl and I was pleasantly surprised when I looked into the mirror. Cleo said I would have no problem "passing" as long as I worked on my mannerisms and removed hair from my hands. She said she could hide the hair everywhere else, but I needed to swap my "hairy" hands for smooth! She even took several pictures of me for me to take home. We enjoyed girl-talk as I looked through Cosmo and Glamour magazines. It was perhaps, the most enjoyable evening I had ever spent. I promised Cleo that next time I wanted to go out in public as Kristen.

It was several months later when I finally had the money and the time to give Cleo a call. I made an appointment to meet Cleo at 5 p.m. on a Friday night. It was a week and a half away and I could hardly wait.

When I arrived, Cleo gave me a big hug and said that I was now one of her "girls". We had a cup of coffee and got ready for my big night. I had a surprise for Cleo – not only had I removed the hair from my hands, but I removed all of my body hair. We immediately began to work on my make up and finger nails. After that, I had many dresses and outfits to choose from and tried on several of them. I had always wanted to wear a "little black dress" out on the town so when I saw that she had one just my size, my eyes lit up. It was perfect. It had a high collar and long sleeves. It was form fitting and had a short skirt. If you can fall in love with a piece of clothing I certainly did! The only problem was that the dress was so tight that I had a hard time hiding my arousal. So after some maneuvering and some tricks that Cleo shared with me, I was ready for the next step. Cleo pulled out several wigs for me to try and the decision was quite difficult. I chose a wig that matched my own natural brown hair and brown eyes. The hair style was short and wavy and I was amazed at how natural it looked. After complimenting the outfit with some jewelry and some black boots, I was ready to roll. I still had some work to do on my mannerisms, my voice, and my ability to walk in heels, but I joked that if I could just remain still and not talk to anyone, no one would think I was anything but an attractive young woman!

We were ready to go and I was excited and frightened at the same time. Cleo insisted that I bring my "male" clothes just in case we need them. She gave me a small purse in which to keep my essentials – lipstick, money, identification, and cigarettes. Okay, cigarettes are not an essential and strangely enough, as a male, I do not smoke. However, as a female, I found smoking to be terribly sexy and exciting. I explained to Cleo that smoking was my only vice, which actually was not true – it was just a turn-on. She said that she did mind at all. So, I sat in the passenger side of Cleo's car with my heart pounding through my chest. Cleo said she would take me to a gay bar that had drag shows because it was good place to go for my first time. She said that I would be very comfortable there. At that moment, I questioned whether I could be comfortable anywhere. I had gone from be frightened to being terrified. I almost asked Cleo to turn the car around, but I resisted.

We pulled into the parking lot of the club and I asked if we could just sit for a moment for me to "gather myself". Cleo actually suggested that I smoke a cigarette to help calm my nerves. So, we sat and talked while I smoked. When I finished my cigarette, I opened the car door and I walked with Cleo toward the club. Looking back now, I can laugh at my exaggerated, sexy walk. I think I was trying too hard to play the part!

Once inside, we immediately headed to a table near the bar. I scoped the scene as we sat down. I soon realized that the most peculiar thing about this place is that I was not all that peculiar myself. I saw guys who looked like they belonged in a gay bar. I saw guys that looked like they belonged at the Republican National Convention. I saw guys in drag that were obviously guys in drag. I saw women who could have been rugby players. I saw women who could have been models. And I saw some that I could not decide if they were women, men, or somewhere in between. This was an exciting place, and I began to relax.

Then a remarkable thing occurred. A woman approached me and asked me my name. I told her that my name was Kristen with a smile. She looked at me kind of funny and apologized. She had actually thought I was a real girl. From that moment on, I felt free to be who I wanted to be. I was also beginning to attract attention from some of the guys, and that was something that I found exhilarating.

Cleo and I ordered a drink and a bite to eat. While we ate and enjoyed our drinks, we watched a man do everything he could to impress a crossdresser at the bar. She obviously was not overly impressed with him and his attention soon when elsewhere – to me! He looked at me and smiled. He walked over to me and asked if I was a "special girl". I replied yes and that at the moment I was busy talking with my friend. I was actually too scared to say much more. He did not give up right away, but he soon took the hint and began his prowl again searching for another innocent "victim".

A seat opened up at the bar and I asked Cleo if she minded if I went to it. I was feeling brave and confident. I sat down at the bar and ordered a glass of wine. Within moments I had two guys hitting on me. These particular gentlemen did not interest me a whole lot, but I have to confess that I did enjoy that fact that they found me attractive. There was however, a handsome fellow couple of bar seats away from me that I could not keep my eyes off of. He looked to be a just a little bit older than me. He was dressed like a young business man. He was also looking me over. He gave a little smile as I smiled back at him. I kept thinking, "Why won't he approach me instead of these goons?" Finally, I decided to try something. I pulled out a cigarette and placed it on my lips. I pulled out my lighter, but I "accidentally" dropped it on the floor toward him. Taking my cue, he picked up my lighter and came toward me. He ignited the flame and held it out in front of me. I leaned forward and lit my cigarette. I thanked him for being such a gentleman and introduced myself. His name was Gary and He motioned me toward an empty table. We sat down together and I told him about myself and that this was my first time in public "dressed". He told me that when he first saw me he assumed I was a lesbian and that I was way too pretty to be a crossdresser. Of course, I was thinking that he must have lost his contacts on the way in but instead of making a sarcastic remark, I simply said, "Thank you". We enjoyed small talk for quite a while. He was so nice and it became obvious to me that he was interested in a lot more than just talk. I was excited and attracted to him, but also frightened. I had never been with a man and did not know what to do with his advances. In a moment of panic, I told Gary that I had to go because my friend was waiting for me. I made eye contact with Cleo and motioned toward the door. Gary seemed disappointed but asked if he could escort me to the car.

Cleo went ahead and sat in the car and waited for me. Gary held my hand as we slowly walked through the parking lot. Gary asked for my number, but because of my roommate situation, I told him it would be better if I called him. I did not have a pen, so I said his number over and over again out loud and told him I would not forget it. He leaned in and kissed me. It was a sweet, simple, and completely romantic. I truly believe my heart skipped a beat when his lips met mine. Within a moment that simple kiss became a deep and passionate kiss. We embraced and I repeated his phone number many times and told him again that I would not forget it.

He helped me in the car and we said our final good-byes. As Cleo and I returned to her home, I recounted the evening with her. It was more than I could have ever dreamed. There was only one thing that went wrong – before I could find a pen, I had forgotten Gary's number.

I look back on that night as a milestone event for me in many ways. I have also wondered what could have happened between Gary and me if I had the courage to give him my number or if I had just been able to remember his. I have lived and relived that night so many times since and it always leaves me with a smile and sometimes a tear or two.




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