Crossing The Line

Editor’s Note: This is, in fact, part 1 of a 4 part series. We hope you continue to follow through Jessica’s journey. Thank you.


A long time ago in a land far away, where songs like “Do ya think I’m sexy” by Rod Stewart were constantly being played on the radio, and there were gasoline shortages across the country, I was born a bouncing baby boy. March 3rd, 1979 to be exact. I was originally born in Annapolis, Maryland but my family moved to the giant metro area of Chicago in 1987, meaning this is where most of my childhood memories are from and where I declare my hometown to be.

I was born into a pretty conservative Christian family. I remember the pain of wanting to sleep in on a Sunday morning as a child, but then I heard the subsequent knocking on my door from my mother yelling, “James time to get up and get ready for church.” I dreaded this wake-up call and would try to give some lame excuse every time to avoid having to sit through the excruciating pain of a Sunday morning church sermon.


This was pretty much routine as a kid. Going to school every day to get picked on, being bullied by the neighborhood kids, and then going to church on Sunday to pretend to do what in their eyes was the ‘right thing’.


I had a rough childhood. Dressing up in male clothes filled me with hate and left me feeling like wearing a suit was how I displayed a religious belief in God. There are many days I can remember dreading going to school. Who would want to have to take that long bumpy school bus ride only to feel like you’re being tortured by other students just for being nice because that’s what my parents taught me religion was all about?


Many of my childhood friends were other kids who felt just as left out. A lot of time was filled up after school playing soccer and pretending I was good at playing basketball. It was obvious to me that I sucked because I was the kid who scored 2 points all season, and whenever I did score that basket I would jump around in jubilee acting as if I just won the NBA Finals.


Starting at around about 8 years old, I began to notice some interesting things about myself. Pretty things and more feminine-related toys like dolls had always attracted me, and I had always seemed to get along better with the girls on the playgrounds at the schools I attended. Maybe they felt awful for me because they saw all of the horrible damage the other kids were doing? Who knows. Dresses had always been beautiful to me and I wonder if that’s really where my curiosity began.

One day I precautiously snuck into my mom’s closet as she was working an overnight shift at the hospital to entertain my curiosity concerning the feminine side of life. I picked out this really beautiful floral dress and tried it on. Of course, I had to look at myself in the mirror and I couldn’t help thinking I look beautiful! It felt like my whole world turned upside down and it felt amazing! But I knew I had to quickly take it off and put it back where I found it so that no one knew I had been there. I was terrified about the potential consequences of my parents finding out what I had done but since then, I knew something was wildly different about me.


LGBTQ topics weren’t something openly talked about much back then; especially when one grows up in a conservative household. The big issues at hand were women breaking the glass ceiling and the AIDS crisis. This pattern of closeted cross-dressing continued on for years because of the feelings of amazement I gained from it.

Eventually, my parents found out about the extracurricular activities I partook in when they were not at home. I honestly don’t think they really knew how to deal with me; still, I felt terrified at what my punishment might be. In my mind, I hadn’t done anything wrong. My parents eventually decided to send me to Christian counseling to ‘fix’ the problem. At the time I had not realized I was exploring my gender identity; however, the thought of me being transgender was never brought up, not even in the counseling sessions. I am sure my parents would’ve denied thinking my gender is female. The counseling sessions were nerve-racking. I often shook in fear of not knowing what to expect over being forced to talk to a complete stranger about my behavior.

The counseling was, of course, ineffective. You cannot change who a person is. I continued down this path of closeted cross-dressing for years and when I tried on those clothes to the point that, some days, it even brought tears of happiness to my eyes because it felt so right to wear them.  But in the real world, I was stuck hiding that happy person and attempting to be a ‘normal’ kid, when normal didn’t even exist in my dictionary.

Years went by and I managed to survive the pain of high school; still feeling like I didn’t fit in anywhere. Yet I was the smart kid who loved science club, Astronomy club, NHS, and cross-dressing. I watched the Fresh Prince of Bel Air, Saved By The Bell, Salute Your Shorts all of those typical kid shows. But of course, I had not been aware of any cross-dressing or LGBTQ friendly clubs at the time. In fact, in the 90s as far I was concerned if a guy dressed as a woman and people found out about it, they laughed at him. This is probably why I constantly lived in fear of not knowing why it brought me happiness to wear female clothes. It’s because I knew the world, at least then, wouldn’t accept it.

When I finally graduated I was still hiding my secretive self. I went off to college away from home in Kansas because I really wanted to find myself and moving to what felt like a distant land far away from my conservative family and childhood bullies felt like the easiest way to go about doing it. I went to school for a few years at Kansas and studied meteorology, my most favorite area of science. Sadly, it didn’t work out and I transferred back to my new family home as they had moved to Milwaukee and finished my college degree at UW Milwaukee. It got quite expensive going to an out of state school. After I transferred to UWM, I once again attended church with my family and met a lady at the Pentecostal church my parents decided to go to. Her name was Sarah and as I tried to continue the game of life, she would later become my wife. Who could have ever guessed, what would happen next…



Jessica Katzenmeyer, 39, West Allis, WI

Currently self employed full time as a Uber/Lyft driver in Milwaukee, Events Coordinator for Erica Flynn for State Assembly, Emerge Wisconsin Alum, interviewed in “Why She Runs” film documentary, former host of “Be Yourself Show” LGBTQ+ podcast talk show for a few seasons, world traveler, has made several guest LGBTQ+ panels and speaking appearances, has musical stage acting experience in the Milwaukee area.

Editor Credits: Jennifer Nicholson and Veronica Spicer

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4 thoughts on “Crossing The Line

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  1. This was a very good read! I have a daughter that hates dressing as a girl. She tells me all the time she wants to be a boy or that she is a boy. She is 7, and I believe she is beautiful either way she chooses to go. I would love to read more about this subject. Keep up the great work!

    Liked by 2 people

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