Roadmap To Transition - High School and Beyond

When I was a Senior in High School in Albuquerque all my friends wanted to go out drinking all the time. And of course, I did my share of that, too, as long my family was home and I didn’t have a chance to dress up. If they were gone, I preferred to spend my time alone, well, except for Lin’s closet. I was working at a fast food place then. Once the rest of the family went up to the lodge, our vacation cabin on the Pecos River that my family built. They were to be gone a couple of days and I couldn’t get the time off to go with them. It’s true, I couldn’t get off, but I wasn’t too broken up about it. It gave me the whole weekend to myself. One of those nights I went to the movies on base. What nobody else knew was that I was wearing one of Lin’s light georgette sheath dresses under my regular clothes. As I was walking home a car load of my friends drove by, both girls and boys, and they wanted me to go out with them to party. I declined because I knew that if I went, something would happen. Either I, or one of the girls, or both would be a little tippsy from wine or beer, we’d start getting a little frisky, and she would see or feel Lin’s dress and I would be found out. That was also the year that we had “Hippy Day” at school. I borrowed a pair of Lin’s purple velvet hip-huggers and wore one of my own pink and purple flowered shirts that went well with the pants. I was on cloud nine all day knowing that I was wearing girl’s clothes to school, even if it was just pants. I felt great wearing girl’s clothes to school and nobody cared.

It was in H.S. that I realized that when I dressed up I didn’t just feel like I was Chuck in a dress. There was more to who I was, who I am. It didn’t seem right to look at myself in the mirror wearing a pretty dress and say, “Chuck, you look pretty.” The girl in me needed a name that was female. That’s when I chose the name Lindsay. That was long before my niece was even a thought, so I didn’t name myself after her. Lindsay is still who I am now, who I have always been. Then I thought that I was Lindsay just when I dressed as a girl. I would later realize that I have always been Lindsay, regardless of what I wear. I am not Lindsay because of what I wear. I am Lindsay because of what is in my heart and mind.

In college I continued to dress. Most of the time I had my own room, even though I had house-mates, and I managed to keep my secret. My best friend back then was Rick. His girlfriend was Debbie. When I moved into the apartments that Deb’s father managed, I worked security there. Rick and Deb and I had a friend that was getting married and we went to a party for the Bride & Groom the week before the wedding. While we were mingling Rick and Deb had gone off someplace to visit with friends and a girl I didn’t know approached me. She introduced herself and told me that she had been to the apartments to visit one of her friends who lived there. Her friend was a male and she had a female friend with her that night. She and her girlfriend had talked the guy into letting them dress him up as a girl and they had taken him out driving around. They were all giggling and having fun when they drove back in and I checked them at the gate. I knew that something was going on but I also knew they had been in numerous times visiting the friend and had never caused any problems so I let them in without knowing the third girl in the back seat was the guy. When she was telling all this at the party I remembered the night she was talking about and thought that the guy didn’t make a half bad looking woman and I told her so. Then she floored me. She told me that I would make a good looking woman also and she could help me like she and her girlfriend had done to that guy. It took me by surprise and all I did was blow her off saying I was too ugly to make a pretty woman. She said “your loss” and walked away. Regret #3. I wished that I had taken her up on her offer. But, if I had, I probably would have found a reason to stay in Albuquerque, I probably would not have moved to Texas, and I wouldn’t have met my future wife, Diane, and I wouldn’t have a beautiful daughter, so even though it seemed like a regret at the time, it seems that I made the right choice.

When I moved to Texas and met Diane, I thought being married to a beautiful woman would cure me of this curse. Regret #4. I didn’t tell Diane, my future wife and soul mate, that I thought I should have been a woman. I fell in love with her pretty quickly. At first I was afraid that she wouldn’t be able to handle me being femme, and I was sure she would leave me. Then I found out about Michael, her first husband, and how hurt she was finding out that he was gay. Me hurting Diane like that was the last thing I wanted to do. I was already in love with her and knowing about Michael only made me feel MORE GUILTY. I couldn’t tell her then, that would have crushed her. So, I didn’t tell her. I should have. Making the arbitrary decision not to tell was, in retrospect, selfish. She should have been given the information and had the chance to make the choice to either stay and marry me and my femme side, or run for the hills. I didn’t give her that choice. I took that choice away from her because I was afraid that she would leave me if she knew. That was selfish. I was hoping Diane would be my salvation, and in a way, she has been. Just not the way I thought at the time. I did stop dressing for a while. I was, am, that much in love with her. I was willing to give up the thing that had given me so much pleasure, and pain, over the years. The thing that made me feel whole. It wasn’t until well after we were married that I realized that this is not something you get cured from, it’s part of who we are.