From Crossdresser to Sissy: My Journey of Self-Discovery and Embrace

When I reflect on my life and attach labels to myself, I view those labels as having more meaning to me as an adult than they did as a child. During my childhood, I identified as a girl and as a girlfriend. However, I would not have been a girl if not for my grandmother, and I would not have been a girlfriend if not for Steve.

When Steve enlisted, I still wanted to be his girlfriend. But as he was gone, I had no way to be a girlfriend. Our family moved back to Spokane that same summer, and I spent my senior year in a new high school. As is quite common for high school seniors, my focus turned more towards my future. I was one year from my eighteenth birthday, from starting college, from being my pursuit of a teaching career. It would also be the year I first learned of Christine Jorgensen and learned of a procedure which was called ‘a sex change’ at the time. And thus began my search for identity.

I Become A Crossdresser

While I could no longer be a girlfriend, as sex as a girlfriend was no longer an option, I turned to a life of crossdressing. I cannot say when I first came to know the term ‘crossdresser.’ I do recall referencing this secret pleasure of mine as ‘dressing up.” Without wanting to be definitive, I feel it is likely that I knew the term ‘crossdresser’ during my girlfriend years. I simply did not feel it was a term that applied to me. However, with Steve gone, I needed to find a new label for myself, and I came to think of myself as a crossdresser.

This new identity began to take shape in the summer of 1970. It solidified as my identity a few months into my marriage, around the fall of 1975. As mentioned, I had come to learn of sex changes during my senior year of high school. This singular piece of acquired knowledge would shape for life for years and decades to come. I wanted a sex change. But I also wanted to teach. The two goals were incompatible. After careful consideration, I decided I would have to put the sex change on hold in pursuit of my career goal of teaching. Without question, I have never been more confused about who I am and what I want than when I went through this decision-making process.

In the summer of 1971, while working in Yellowstone National Park, I fell in love. With a girl. It was not to be, and I returned to Spokane, where I started college in the fall. I was changed. I had started drinking while working in Yellowstone, and alcohol would shape my life for the next three decades. But I had also decided I wanted to be married. To a woman. We would raise a family. Have a home. Love our grandchildren. The only problem was I was crossdressing. I loved crossdressing. I was a crossdresser.

Crossdressing Is Not A Sexual Identity

Was it love at first sight? Maybe that only happens in the movies. But the day I met Amber, my life changed. Steve had died in Vietnam. My childhood years as a girlfriend were a thing of the past. I began to see a different future for myself, a future with Amber. Within six months, we were engaged. I lost my virginity to her — as a male. My life was on a different path. With only one problem, I was still crossdressing.

There are lies we tell ourselves, lies we want to believe even as we know they are not. Throughout our crossdressing, I often would crossdress. But I told myself the lie that everything would change once we were married. Marriage is a commitment, and once I made that commitment, I would find the strength to ‘cease’ my crossdressing. And I was right. For the first few weeks at least. However, in time, the allure of her half of our shared closet was too strong. I began wearing her clothes. As crossdressing is not a sexual identity, I told myself I could crossdress and still be faithful to Amber. It was at this time that I fully embraced the label of crossdresser. I convinced myself that as I was a crossdresser, crossdressing was not an option for me. It was something I had to do. Or I was simply not me.

My Life As A Crossdresser

Two years into our marriage, in early spring of 1977, Amber discovered she had married a crossdresser. While it would be five years before our divorce, our marriage ended with that discovery. Since 1977 until now, the number of times I have had intercourse with a woman could be counted using the fingers on one hand. Amber and I did occasionally get sexual , but it never went as far as intercourse, and my penis was never part of the experience. At the same time, crossdressing was not sexual for me. At least until 1992.

During these fifteen years, I struggled with my identity. During a time in Dallas, I felt that frequent visits to strip clubs and generous tipping of all but naked women made me a man, but I continued to crossdress. I found myself growing increasingly envious of these women. At home, I developed the habit — rather the compulsion — of writing letters to Penthouse. I never sent any letters to Penthouse, but I wrote (or at least began) hundreds, maybe even thousands of fantasy letters about life as a woman. Some of the letters were confessional, sharing secrets of my relationship with Steve.

During this time, I found myself yearning for normalcy. I wanted to be normal. But I also wanted to wear dresses and sexy lingerie. And in the back of my mind was the knowledge that as a transsexual, I could get a sex change.

Redefining Myself

In 1992, I was living in Dallas, and I began to consider going out as Veronica, which I had not really done since high school with Steve. This meant going to gay clubs for me, and Dallas seemed ‘too gay’ for me. So I decided to return to Spokane. I felt more comfortable with the idea of going out in Spokane. This is not to say I had come to accept myself as gay. There is a reason I did not want to go to the ‘too gay’ clubs of Dallas. I would come to self-identify as transgender at some time over the next couple of years. I learned a great deal about gender identity and crossdressing from the internet, which emerged during the nineties. In 2000, I attended the Southern Comfort Conference in Atlanta as a transgender woman.

By 2000, three decades of my life had passed since I first learned of gender reassignment surgery. There was never a time during these thirty years when I did not — at least as some level — want to have this surgery. But it was never a priority. I never made it happen. I did some research. I found out how difficult it was to be approved for the surgery , not to mention the costs. As much as I wanted to have the surgery, as much as I wanted to be a woman, for years I settled for the life of a crossdresser. During my clubbing years, I was not gay. I was transgender. However, somehow I was only transgender on weekends — and only went it meant going to a club, certainly to get drunk, hopefully to get laid.

Can’t Get Drunk, Can’t Get Laid

At fifty, I began living a sober life. I have been living a sober life for twenty years and then some. This is not to say I earned myself a twenty-year coin because I did occasionally drink. And I have gotten drunk a few times. Each time I have gotten drunk, I have done so before going out to a gay club fully dressed as Veronica to get laid — hopefully. I am talking about say ten times, maybe a dozen — but nothing I do more than one or twice a year — if at all. I mention this because once I got sober, I did not know how to get laid. I needed alcohol to find the courage to step out as Veronica and I never found a way to meet men elsewhere. [Craigslist was a solution for a brief time, but then it got very strict regarding ad postings.]

Around 2014, I was living in Washington State and came across a PDF on the Healthcare Rights of Transgender Washington Citizens. For the first time in my life, gender reassignment surgery was a viable option. I began hormones and counseling. Three years later, I was able to change my name to Veronica and my state ID gender marker to F. And yet nothing changed for me.

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