Crossing The Line (Pt. 2)

Editor’s Note: This is, in fact, part 2 of a 4 part series. We hope you continue to follow through Jessica’s journey. Thank you.


In 1999 on a day in early May my Dad and I completed the long 10-hour drive home. I was no longer living in the home I had known since I was a kid or bound to the walls of my dorm room. In comparison to Chicago; Milwaukee, Wisconsin seemed like a foreign land.

I was lonely, not knowing a single person outside my own family, and at times my feelings of being confused over why cross-dressing brought me so much happiness overwhelmed me. Summer break had just begun and I was in between transferring to a new college, UW Milwaukee. I looked at this change as an opportunity to start fresh in a new life.


My parents had started going to a new Pentecostal church in the area, so as any good Christian kid would do, I followed suit. Eager to want to meet new friends, I started attending several groups involved with the church. This was a pretty strict church with very conservative views, such as claiming it was a sin to listen to worldly music or partake in drinking activities. After some time, I met a beautiful blonde woman named Sarah. We seemed to connect on several levels and she appeared to be the perfect Christian.


Eventually, we began to pursue a relationship as more than just friends. Our first date consisted of going to a local diner, followed by a bit of bowling. The date set, what I thought was going to be, an amazing precedent for more to follow.


Time passed and she went off to college in Minnesota. To keep the relationship going, we both traveled back and forth once a month. Our relationship seemed to be heading towards the so-called American Dream; going to school, graduate, get married, have a job, and live in that suburban cookie cutter neighborhood with several kids. Nearly 2 years into our relationship, I took the next step and nervously proposed. While happy on the outside that I was getting married the real me was still hiding on the inside, fearing what may possibly happen if my secret came out.


Just days after graduation day, we got married in the Pentecostal church. Our first few years of marriage were great, but at times I felt like I was putting on a fake happy face because my habit of cross-dressing was once again in the closet.

It wasn’t long before my wife had found out about what was going on, causing our relationship to begin to crumble. One afternoon, a nasty argument resulted in her throwing a hairbrush at me. The pain of impact to my head was instantaneous and right away she quickly began to apologize while rushing to my aid. In confusion, I wondered how she could love me enough to try to comfort me but still reject my cross-dressing.

Eventually, another argument broke out over her finding that I had messed with her clothes while cross-dressing. The surprise of the reveal lead to her hitting me several times and while I didn’t attempt to stop her, I couldn’t fight back the terrible feeling of sadness her response left me with. While she locked herself in the bathroom to calm down, I continued to lay there for what felt like hours wondering what our relationship had turned into.

I had never considered that this would be her reaction and the fear of it getting out kept me silent.

Time passed and our marriage just became more and more strained. The fights continued to happen and I began to suspect that the wedge in our relationship had driven her to find someone else. Eventually, I realized we couldn’t live like this anymore and that something needed to change. My thoughts turned to suicide at some point and while I knew I would never act on them, depression gradually set in. I felt like I had reached rock bottom and despite still feeling like I wanted our marriage to work out I decided to seek a divorce attorney. This was the real way out, but part of me was so scared to really leave my wife and scared to face what people would think of us in the church. The church preached love, but our relationship no longer felt like it had any love left in it.


The days leading up to our divorce hearing were really challenging. We had a lot of debt between us, causing my ex-wife to do something I had never imagine anyone could do. She threatened to out my cross-dressing which led me to reluctantly sign an agreement to pay a majority of the debt we had incurred. I felt weak for giving in to the blackmail but still feared the outcome of coming out before I was ready.


The tragic end to our once happy marriage again caused me to experience suicidal thoughts. Fed up with the bigotry, I left the church and became more or less agnostic in my religious beliefs. I also hadn’t told my parents the truth about the reasons for the end of my marriage, in part due to fear of their reaction and because I had been forced to move into my dad’s house due to the debt I incurred from the divorce.

As far as I was concerned life was hopeless. Thankfully though something kept me going. Soon, I met a friend who identified herself within the LGBTQIA community and began to open my mind on many subjects. After some time, I confided in her about everything that had led up to the divorce. It was her that eventually taught me about what being transgender meant.


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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