It was 5 AM before my wife, Terri, and I climbed into bed, and she asked me if I was tired, and how I felt after my first time out. In the few seconds it took me to compose my answer, the scene in “My Fair Lady” ran through my head where Eliza Doolittle returns from her first ball and runs along the stairway, resisting everyone’s attempts to get her ready for bed and singing “I could have danced all night”. And, in truth, that is how I felt. For, like Eliza, I had been transformed in only a few short months, from a closet crossdresser, surreptitiously putting on women’s clothes when there was no one else about, into Lisa, and tonight had been my first ball.

The rrrain in Spain falls mainly on the plain

Only six months earlier, my wife had finally been ready to see me dressed up. But in the following period, I only dressed up occasionally, late in the evening, with no thought of going out. We would sit and talk, and then a couple of hours later, I would undress again and we would go to bed. If I wore makeup at all, it was just a bit of lipstick.

A couple that we had come into contact with on the Internet suggested that we go to the Halloween party organized by one of the T-groups. At first, I automatically rejected the notion, but they both kept on telling us how much fun we would both have, and what a revelation it would be. The idea intrigued me. But I was scared. Scared of what? I couldn’t put my finger on it then, and I still can’t, but I was both terrified of going, and curious and excited about the idea, at the same time.

Two or three weeks later, Terri and I were out shopping together, and we saw a red skirt. I had been saying to her for a while, that I wanted to start developing a more colorful wardrobe, as most of what I had of my own was black or gray. When Terri would ask me what I had in mind, I would answer, “now, for example, I would love to have a bright red skirt.” And there it hung. As usual, being close to my size, Terri tried it on for me in the shop, and it looked great on her. But it was a bit dressier than I had expected, and I asked her, jokingly, “but when would I wear it?” And she answered, with a smile, “why, to the Halloween party, of course.” We both laughed, and we bought the skirt.

As we were walking out of the store, I asked Terri how she felt about the idea of going to the party, and she said that, in truth, she thought it would be good for me. She admitted that she, too, was apprehensive but curious. The seed was planted.

Just you wait, 'Enry 'Iggins, just you wait

Soon after that, the subject again came up again, and we decided to give a preliminary “yes” to the idea of going to the party. I had a whole list of conditions that had to be met, but if they were all met, I would gather up my courage and go. The first condition to be met, was that I would have an outfit that I felt appropriate for the occasion. Not too dressy, but not too informal. I already had the skirt. We looked through my limited wardrobe of tops, and Terri’s more extensive one, but could find nothing that pleased me. So, in the following weekends, a series of shopping trips ensued. First we found a beautiful zip-up vest with a fur-like collar, gorgeously feminine. Finally, not less than a week before the party, we came across a simple black top, in a soft, supple material, with a straight neckline. We topped it off with a silver belt across the hips. I would wear black pantyhose, and since I would have to stand on my heels all knight, I would stay off my high black stiletto sandals, but instead chose to wear my black sandals with a ½ inch platform sole and 3 ½ inch block heels, that I had bought at “Payless for Shoes.”

There is a story behind those shoes. I travel frequently for business, both in America and Europe. Back when my wife was not so accepting, it was always an opportunity for me to get out to the shops and look around for something. I particularly liked Payless’ shoes. They are inexpensive, they have a large selection in large sizes and they are very much a self-service shop; the shoes are arranged in pairs in boxes in racks, and so you can look around relatively anonymously. On the down side, though, their women’s sizes are not always as consistent as I would like them to be, so since it is difficult to try the shoes on there, it is a challenge to buy the right size. My usual technique is to find a pair of men’s shoes that fit, and then hold them next to the shoes I was considering and see if the lengths were identical. I have been in many Paylesses, across the country, before, but I came across these shoes at a Payless on the wrong side of the Mason-Dixon line, in the heart of redneck country. So, imagine my surprise while I was trying to decide between two sizes of this shoe, when the woman working in the shop just came up to me and said “why don’t you try them on?” I was flustered and turned beet-red, but stammered and said, “no, that won’t be necessary”, and put one pair back, paid the $15.99 for the other one and quickly left the store. Back at the hotel, I tried on the shoes, and realized they were way to big, but it was too late to go back, the store was now closed. So I went back the next evening, hoping she was working again, to exchange them for a smaller size. And this time, I would try them on. Unfortunately, another person was working that evening, so I just exchanged them for a smaller size, and left again. The size I have is still probably at least a size too big.

I am still such a coward when it comes to that. Recently, we were out shopping and were alone together in a boutique. It was a bit of an alternative style, but had a lovely Chinese-style dress that Terri thought would look good on me. We were all alone and the girl working was dressed in such a manner that you could tell that she would be cool about it, so Terri said “why don’t you try it on.” But still I chickened out.

So, we had the outfit from top to bottom. I was going to borrow Terri’s pearl necklace, and we had found nice pearl clip-on earrings to go with them, and fake pearl bracelets.

Next was the makeup. I certainly did not know how to do it, and Terri, who is beautiful in her own right, and only needs to wear a little makeup to look stunning, did not think she could do a good job. But there would be professional makeup artists at the party who would make up anyone who wanted it free of charge. Still, I needed convincing that I would not look ridiculous. So, in the next couple of weeks, Terri experimented on me, trying to give me as feminine a look as possible. Finally we found a look that we were both pleased with. I have no illusions that I will ever be a great beauty, but I could look myself in the mirror.

The last piece was the hair. I don’t have a good wig, yet. But my hair is fairly long, and could be fashioned perhaps into a woman’s style. So we began experimenting with that. I bought a red hairband to wear in my hair, and Terri played around with her curling iron. We finally thought we had something acceptable. So we contacted our friends and said that it was on. Starship Lisa was about to be launched. Still, though, the butterflies were fluttering in my stomach. Then I remembered, that I had hidden away somewhere a cheap black wig that I had bought for $29 in one of those shops along Eighth Ave. in New York that sell cheap wigs, makeup and beauty supplies. The one-size-fits all is a bit too small for me, but we dusted it off, brushed it into shape, and I was ready.

The Sunday before the party, I started my preparations. Terri helped me paint my toenails bright red, since I would be wearing open sandals. Before taking a shower, I put Nair on my legs and removed all the hair on it. On Halloween itself, I decided to work only a half a day, and to do that from home, rather than go into the office. I got up early, got dressed, plugged in my laptop, and worked until around 1 PM. Then I put away the computer, took a shower, and started shaving and shaving and shaving again, until I had gotten my face smoother than it had ever been. I put on my “underneath” clothes, a pair of panties, and sheer black sandalfoot pantyhose. I packed up the outfit that I would wear, since I would change at the party. Terri came home early from work, showered and got into her party clothes. She wore a long, leopard-skin skirt with a black lace top. She put her blonde hair up, finished her makeup and looked gorgeous, as usual. Our internet friends had offered to accompany us there, so that it would not be so terrifying, so we drove over to them and picked them up.

The party was held at a private club housed in an old mansion in a small town in the countryside. I had selected the CD’s I would have in the changer, just for the occasion, and pressed the button for the next CD and on came Shania Twain with “Man, I feel like a woman” – “the best thing about being a woman is the prerogative to have a little fun.” We arrived and walked in the dark towards my debut. My heart was pounding so loud that I could hear it. Terri looked back at me and gave me a smile, grabbed my hand and squeezed it. We were among the first to arrive, so I ran upstairs, took off my sweater and put on the black top, ran downstairs again and waited for the makeup artists to do their magic on me. And they are truly artists. Mixing and blending colors, my face was transformed. Terri watched as her husband turned into Lisa before her eyes.

Wouldn't it be luvverly ...

I looked in the mirror, amazed at what I saw. Then, I told Terri to get herself a drink, while I went upstairs to complete my transformation. In the meantime, people continued to arrive, and we were a merry group in the dressing room as we changed into our party clothes. After the skirt, I carefully arranged the belt, put on the shoes, bracelets and necklace. The last piece was the wig, which took a lot of effort to get right. I came downstairs and was ready to make my entrance. There were T-girls and partners all around me, there was music playing and noise everywhere, but for a second, it seemed like the world stood still as I walked into the room. For the first time, I was walking among people dressed as I had wanted to be dressed for a long, long time. Perhaps it is my imagination, but I could feel that I was being watched as I had never been watched as a man. I imagined that people were looking at me the way men and women look at other women, to judge what they’re wearing and how their makeup looks. I searched the crowd for Terri, who was sitting in a corner with her drink. She looked back at me and smiled, and everything was all right.

That evening, I met a number of other girls whom I had corresponded with on the net, or chatted with.  We talked to strangers. I received a number of compliments – a girl can never receive enough of those. The party went on, we relaxed some more, and when a golden oldie from the disco years was played that we were both fond of, we made it onto the dance floor and started to boogie. There I was, in my heels, dancing to the sounds of the seventies. I could see in my shadow, how the skirt hugged my legs and gently rocked. 

I wished the evening would never end, but of course it did. We went back to our friends’ house, and had some coffee and talked about the evening. Finally, it was time to put this magical day to bed. And as I climbed into my bed, I started humming “I could have danced all night, I could have danced all night, and still have begged for more ….”