When Did I “Know?”

One of the most common questions I get is: “When did you know you were transgender?” It is usually asked right after the question “So since you and Jenni are staying together, does that make her…… ?“

=)

There is a short answer and a long one. The short answer is that I came out to myself, and committed to transitioning in the summer of 2016.

The long answer is obviously more complex than that. The earliest memories I have of myself that stand out to me as being different, start when I was in middle school around the time puberty started to set in. Somewhere in the 7th grade. I would sneak into my sisters closet when no one else was home and see what I could fit into. She was younger than me, so all her clothes were smaller. I remember though she had a couple skirts my mom had made her that had an elastic waistband. They would fit me and I loved it. I had so many feelings that would run through me when I would sneak in and try on her skirts. I was beyond elated, confused by my own actions, absolutely terrified, and horribly ashamed all at the same time. I just couldn’t help myself though. I had such a strong pulling urge, a deep burning desire to dress like a girl. I remember those few short lived moments seeing myself in the mirror in a skirt. It was euphoric. I was so happy to see myself reflected back at me. Then the terror of being caught would slowly start to creep in. What if someone came home and found me? That feeling was followed by the confusion of why I was doing it in the first place. Finally the shame for having snuck into my sister’s closet would overrun the bliss of being dressed as a girl. The scenario would always end with me quickly putting everything back where I found it, careful to leave no trace, and leave the room with my heart pounding its way out of my chest.

I have since recognized that feeling as gender dysphoria, but that word and idea was not part of my world in the early 1990’s. I was living in a small rural town. I was never exposed to anything other than straight romance, and cisgender people. I had never even heard of drag at that point. The internet was just starting to be born.

As puberty started to take hold around that time, and my body started to change, I grew unhappy with the way I looked and my own reflection. Top that off with the hormone changes and problems associated with being a teenager in general. I really started to hate seeing myself in pictures. I started wearing baggy shirts and not putting a lot of effort into my looks. At the time it was all attributed to ‘part of growing up.’ Looking back now it is easier to see it all as gender dysphoria.

Those feelings stuck with me. I moved from middle school to high school. I would replay the same scenario over and over. The opportunities became fewer as my siblings and I grew up, but I would relish the rare chances I did get. It was a vicious cycle of shame, repressed feelings, building to an overwhelming urge, resulting in a binge, followed by a purge brought on by shame.

Even in college. There were even fewer opportunities to indulge. First in the dorms, and later in apartments with roomates. However the cycle still held. I even remember several times I would make an online order from Victoria’s Secret. My heart would be pounding out of my chest the whole time I was making the order. Then almost immediately after finalizing the order, the fear would set it. I don’t think I made it more than an hour after clicking “Submit Order” before the fear of being discovered was so great I would cancel the order even before it was processed.

You would think I would have gotten a clue at some point, but it still was not an option. The word transgender did not exist for me.

Move past college. I met the love of my life, my soulmate, my other half. Admittedly I didn’t know it at the time. I have always loved her with all my heart, but I never knew how truly right for eachother we were, until this last year. We got married right after college, and started our family and living our lives together.

It was really early in our marriage when, after drinking a lot, asked Jenni if I could wear one of her babydolls to bed. She was surprised at the request, but didn’t dismiss it out of hand. We talked about it. I just admitted that I liked the idea of wearing them. Time passed. I accumulated some feminine pajamas, and a couple more risque items for the bedroom. It became our norm. Only we never really talked about it much. There was an unspoken agreement to never let anyone know about it. We even had some disagreements about what I could wear around the kids as they got older and more aware. It was always feminine, but we tried to keep it from being “too” obvious. My favorite pajamas around the house were lavender silk pants with girl cut shirts.

The beginning of the end, as it were, came when I got a new job that let me work from home. The job sort of fell into my lap. I quickly discovered though that it would give me the opportunity to wear whatever I wanted to during the day. I expanded my wardrobe with a couple pieces here, and a couple pieces there. Almost all purchases online. I got a few skirts, a couple dresses, and a top or two. I completed them with a couple pairs of heels and a couple ballet flats. The first couple years on the job I loved it. There was an initial period where I had to work from the office part time, and I impatiently chafed at the restrictions from being able to work from home. When I finally got the go-ahead to work from home 100% of the time I was in heaven. Each morning I would love getting up and planning my outfit for the day. As soon as Jenni and the boys left for school and work, I would shower and get dressed. Then I would happily work from my computer.

After a couple of years went by I started to become depressed. I dreaded the time that my family would come home more and more. It meant I would have to put on boy clothes. It was a very slow slide down the depression slope. I didn’t notice it. I was so hyper focused on the time I got to spend dressed as the real me. Jenni pointed it out a full year before I saw it for myself. I didn’t believe her when she made the observation. It even started to strain our marriage. I hit a fairly low spot. It didn’t help that the job changed into something other than what I signed up for. I went through 3 supervisors in 4 years. I enjoyed the people I worked with a lot, just the job itself changed into something I didn’t enjoy.

So I left that job and went back to one where I worked in a physical location with face to face interaction. Which meant I had to say goodbye to dressing in what I had grown comfortable with. It was a difficult decision. I was really hesitant to give up working from home, even knowing how depressed I was with the job.

Never-the-less I made the change. I liked my new work environment. It was a positive and supporting environment, with great people. I was happier with the job itself, but really doing some serious self exploration.

Up to this point I still had not asked myself what my desire to dress and act like a woman meant. I was still very much ashamed of that part of myself, while at the same time always looking forward to the next time I could indulge that side of myself. It was very conflicting and confusing.

The big catalyst came as I was transitioning to my new job. Jenni came out to me as Asexual. She was really worried about telling me. Actually I was relieved. I knew something was up, and was really worried that it was the way I dressed and acted in the bedroom that had caused it. Finding out that it wasn’t something wrong with me was actually a relief. I accepted her for who she was. As I was processing what Jenni told me I did a lot of research on what exactly Asexual was and what it meant. That led me to really research LGBT in general. For the first time I really began to explore the concept of transgender people.

Holy… Shit…

It was like my entire life started playing back to me, but with a whole new perspective. I was seeing everything through a brand new lens. My vocabulary was expanded and I was able to articulate things I had never been able to express, even to myself.

It was like I had never been able to see the color red until that point in time. However once the ability was gifted to me, every memory of my existence was replayed in my mind, only now with the color red standing out that much more for having been unnoticed before. It was always there, I just couldn’t see it until now. Now it stood out with blinding clarity.

I started to really research transgender people. It did not take long for me to identify as transgender, and only a little longer to admit outloud to myself that I am transgender. That was only a couple months after Jenni had come out to me. This happened in the summer of 2016.

So that is when I “knew.” =)

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Sarah
I started transitioning (mtf) in my mid-thirties after being married for 11 years and having two awesome boys. My wife has been, and continues to be my biggest supporter. We are more in love now than ever. We are continuing our lives together as a happy family!

About Sarah

I started transitioning (mtf) in my mid-thirties after being married for 11 years and having two awesome boys. My wife has been, and continues to be my biggest supporter. We are more in love now than ever. We are continuing our lives together as a happy family!
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