Chapter 05 ~88.6 miles

The Transgender Pride Flag
Created by American trans woman Monica Helms in 1999, and first shown at a pride parade in Phoenix, Arizona, United States in 2000
click here to learn more

March 29, 2018

I get a lot of questions about my marriage and especially about how my wife is taking my transition. We were married while I was still presenting male, but my wife has known about my feminine side since we first became friends. We met each other after we had each been in bad relationships with bad breakups. We had each taken a sabbatical about the same time to California (me in the Bay Area, her in Pasadena), and we had each returned home to the Milwaukee/Chicago area with a better understanding of ourselves. Our retreats had been in finding out who we were and what our wants and hopes were. We had both been working at an outdoor environmental theater venue for 10 years by this point but hadn’t met until our individual returns back from California to that venue. We came home to the social group that we shared. Over the years that group had dwindled and changed, and got smaller and smaller, and so we finally met after a performance day in a local restaurant. At first neither of us was looking for a relationship. We became fast friends over a similar upbringing. Our parents were older, and our cultural references were very similar.

She was living in Chicago and I in Milwaukee but we saw each other on the weekends at the venue where we worked. On one particular trip driving her home to Chicago (she didn’t and still doesn’t drive) I revealed my feminine side, my dressing in secret. We shared our history of failed relationships. She told me of her relationships with both male and female partners. After about a year of intense friendshipness (yes, I just did that though the computer wanted to auto-correct it to “friends hipness” which I kind of like!) I told her that I had a crush on her. We lived a somewhat long distance relationship for about a year. 88.6 miles, that was the distance on my car’s trip-o-meter. I would watch those digits click past every Friday night as I made my way down to her Rodger’s Park “Garden” bachelorette pad, decorated all pastel blue and purple with hand-painted leopard bathroom walls and leopard upholstered futon. We were in love and spent many hours in and around the Clark and Belmont neighborhood visiting the hip shops like The Alley and Hollywood Mirror, and eating sushi at Nohanna on North Broadway near Briar (now closed). It was the late 90’s and by late 2000/early 2001 she had moved up to live with me in my cramped, 1-bedroom Bay View apartment. The decision to move her to Milwaukee was due to the simple fact that I had a good paying job.

I remember several occasions where she would ask me if had thought about transitioning to becoming a woman full-time. At that point I wasn’t yet identifying transgender. I had not thought about that. I just knew that I had a partner that accepted my quirks. She would often say that she wished we lived somewhere where I could dress and go out, and it wouldn’t be odd. She would talk of places in the US or more specifically in Europe, where she had travelled quite a bit, where it was accepted that some men would present female at times. We lived in that cramped and wonderful space for 10 years growing, marrying, and thriving despite a bedroom with her clothes and two sets of mine, a living room that doubled as a guest room, a dining area that doubled as an art studio and sewing space, and one tiny bathroom. Eventually we bought a 1920s Milwaukee Bungalow where we continue to grow and change in the way that people do with time.

When I first announced that I was transgender and my intention was, over time, to transition to living full-time as a woman my wife began to get all sort of messages and questions of “Oh my! How are you taking this?” and “Are you two splitting up?” or “Are you OK?” Those people didn’t know that we are a very healthy couple. In fact we have never had a fight. We realize that if we enter a discussion with aggression it is most likely due to being tired or hungry, so we eat first and then talk. Others may like to duke it out but not us. We are open and honest with each other.

A few years ago she had seen that my daily life was getting more and more stressful. I had originally attributed it to workplace stress but after making the realization that I was more than just a casual evening and weekend crossdresser, and that my personal growth was stagnating, I needed to get help. I first spoke to a relative who is a retired therapist. It was safer for me to talk to them than begin the process of finding a paid professional. This was in the autumn of 2015 and by the following April I was in regular therapy sessions with a local therapist whose client base is LGBTQIA+. This therapy was initially for “workplace stress” but eventually for gender dysphoria.

To help herself, my wife joined a few “support groups” for spouses of transgender individuals. She said that the typical group member was in the situation of “Oh, my god! My husband of 20 years just told me that he’s really a woman and I don’t know what to do!” But we weren’t and aren’t like that. We’ve been able to talk about this and other things in our 20 year relationship. We support each other and share some incredible adventures together. And those adventures have been in beautiful locations like Venice and the Lake District of England, but also in places like Muskogee, Oklahoma and right here in Milwaukee, Wisconsin. She is my best friend and the only person I want to see when I’m at my worst and need comfort. She’s my travel companion, my navigator, my guide. She makes me laugh all the time. We have stupid phrases that require a specific call and response that reference some of the most inane things. She is by far the most intelligent person I’ve ever met. She can spell any word, and she knows music. Boy does she know music! Her lexicon spreads from Renaissance music through to the current electronic genres. She does have a blind spot for country and western though, except for Hee-Haw, another cultural similarity between us from our upbringings. We can be in a grocery store and an 80s song will come on the overhead speaker and she will name the title, group, producer, where it was recorded, and usually some miscellaneous fact about it. Then we’ll be at a department store and a classical song will come on and she’ll do the same thing, composer, which version it is, the conductor and even the first chair violinist! Why she isn’t a music curator yet I don’t know. She’s written two books on human interaction, edited and published them herself. She is a DJ and will soon be celebrating 5 years on the air (internet radio) where she hosts a live audio/video show of house music (and other genres). Her side projects include foreign language voice-over work (she speaks Italian, Spanish, French, Some German and Dutch). She is hired occasionally as a corporate trainer. And on top of all of this she is manger of operations for a municipal call-center. But I know her as my best friend and the person that charmingly gets her “right” and “left” directions confused.

After I had begun my transition I posted on social media one day that I would take any questions that anyone had. My intention all along was that I wanted to make this transition about educating those that don’t know a transgender person. I want to dispel the myths and help normalize this. I was very surprised at how many people asked about how we deal with our intimacy. This is one of those things where you certainly wouldn’t ask a cis-gender couple about their sex life, and is kind of a no-no, but I did open up to any questions. My response is this, when we married we didn’t marry the other gender, we married the other person. There is so much more to a relationship than sex, and if that defines anyone’s relationship I would be concerned about the stability and longevity of that union. Also, this is one of those questions that you just don’t ask. It’s not polite. Just like asking a transgender person about the state of their genitals, or whether or not they are going to, or have already had bottom surgery (often referred to as “The Surgery”). I know it’s difficult to navigate the “do’s and don’ts” of the etiquette. It’s best to either investigate on the internet or use common sense. If you wouldn’t ask a cis-gender person, wouldn’t want it asked of you, or if you wouldn’t ask your grandmother, then maybe it’s not appropriate. There are great resources online like GLAAD – the Gay and Lesbian Alliance Against Defamation (, or FORGE (, or simply Google “transgender ally resources”. There is a lot out there to help everyone educate and support each other and be a better ally.

For now, for me, I’ve got my own personal ally. She’s willing to physically defend me if she has to. She’ll protect me when I’m frail, She’ll comfort me when I get sad from being  publicly misgendeted. And she’ll sit by my side while I recover from the surges that try to make me whole. And best of all we no longer have to travel 88.6 miles to do it.

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