AI-generated image of a black dress in a closet full of boy's clothes
November 3, 2024

This is the story about the black dress that hung in my closet as a kid. It belonged to my mom and was the garment that kicked off my interest in dresses and skirts. As I recall, the dress was primarily made of cotton, had spaghetti straps and would have come down to mid-thigh if my mom had worn it. Oddly enough, I can’t recall ever having seen her wear it or it ever leaving my closet except for when I pulled it out.

When I say that it would have come down to mid-thigh, that is just conjecture on my part because the hem always ended up well past my knees when I put it on as a not-fully-grown preteen and teenager. By that time, the dress had been in my closet for years and I had seen it every day. Naturally, curiosity got the better of me and I eventually pulled it out to look at it.

At first, I would just spread it out on the floor or my bed and study it. I badly wanted to try it on and see what it felt like to wear a dress, but I was scared. At the time, I didn’t know why or what I was afraid of, but looking back on it with the gift of hindsight, I can say I was afraid of what I thought it would mean if I wore it and liked it.

As an inexperienced preteen, I thought that even just my interest in trying on the dress meant I might be gay and that if I tried it on and liked it, it would be confirmation of that. Unfortunately, it was a time when being gay as a young male was still something to be afraid of. While society in the part of the US I grew up in was becoming more tolerant, gay or “feminine” boys were still relentlessly bullied at school instilling a strong fear in them of falling into this category.

The concept of transgenderism wasn’t on my radar at all yet, so that wasn’t even a consideration. It would only become a topic later in my life, but I’ll write about that in another post.

Pulling the dress out, looking at it, touching it, feeling it, and resisting the temptation to put it on became an almost daily ritual that went on for at least a year. Then one day, I finally gave in and put it on. I can’t remember whether it was after school or on the weekend, but I do know that the fact that I was home alone played a big role in my decision to finally try it on.

I pulled the dress out, looked at it spread out on my bed, then rapidly stripped down to my underwear. I recall being so nervous that I was shaking and sweaty which in hindsight is ridiculous, but what I was about to do was a big deal to me in that moment. I then grabbed the dress and slipped it over my head.

The only way to accurately describe the feeling of finally wearing it is to say that it felt euphoric. I was nervous and afraid, but I somehow felt whole in a way I hadn’t before. It was as though a missing piece of me had finally been found and slid into place. From a distance of decades, that sounds rather absurd and melodramatic, but I remember the feeling distinctly. Even to this day, I still experience a much tamer version of it when putting on a skirt, dress or heels.

That day marked the beginning of a new, life-long passion for gender-non-conformity. At first, I would wear the dress only when I was home alone, but since we were a family of five, that wasn’t often enough for me. Eventually, I got brave enough to put it on and wear it even when other people were home, but only in my room which was pretty isolated in the basement.

This had the side effect that I began to withdraw into my room more and more which my parents just attributed to me being a teenager. Little did they know it was so that I could wear a dress. Of course, a lot of teenagers use the private space of their bedrooms to discover themselves and that is exactly what I was doing.

As with most things teenagers try to hide from their parents, there was a time when my mom very nearly caught me. I was sitting in my room playing PlayStation (the original!) while wearing the dress. It was winter and my room was somewhat cold, so I had a long sleeve shirt on underneath as well as a blanket over me which was fortunate. My room didn’t have a door, but it was in the basement which meant I could hear her coming down the stairs. I obviously didn’t have time to change, so I just quickly pulled my arms out of the dress’s spaghetti straps and pulled the blanket up to almost my neck so that it was concealed. I then kept playing my game as nonchalantly as I could muster.

Obviously, I was quite nervous but fortunately, nothing happened. My mom did notice the blanket pulled way up and the fact that I was acting a little strangely, so she asked if I was feeling alright. I assured her I was fine and that was the end of it. I doubt she ever suspected that I was wearing her dress under the blanket.

Years later after I had told her about my interest in skirts and even worn them in front of her, I told her I used to wear the black dress that she kept in my closet when I was alone in my room. She couldn’t even remember having one in my closet which explains why I never saw her wear it.

As a teenager, I frequently had friends over and we would spend time in my room and play video games for the most part. When I knew they were coming over, I wouldn’t specifically hide the dress as you might expect. Instead, I just left it hanging in its usual spot. No one noticed or asked, but if they had, I would have just told them a redacted version of the truth: it’s my mom’s and she’s storing it in my closet because hers is too full. None of them would ever have suspected that I actually wore it as often as possible.

I can confirm that because I am still good friends with my two best friends from school who came over all the time and I have since asked them. Neither one of them knew about the dress much less that I wore it. A fun twist is that one of them started to wear skirts too even though neither one of us knew about the other one doing it. It was only years later that we discovered we both had a common interest in gender-non-conformity. She later came out as transgender (MTF).

I don’t really know what happened to the dress unfortunately. When I moved out for college, I didn’t take it with me even though I missed it. I wasn’t about to have it in my dorm room which I had to share with another random guy and by the time I had a place with my own room, the dress had disappeared. I assume my mom took it back at some point and probably gave it away to Goodwill like she does with most of her old clothes.

That doesn’t mean I didn’t experiment in college once I had moved out of the dorms though. With what little money I had, I ordered myself a skater skirt with thigh highs (think typical femboy) that I wore every time I thought it was safe enough to. I still had roommates, but I did have my own room with a door I could lock. This went on for my entire college career until I packed up my things and moved to Germany to be with the woman I am now married to. I didn’t take the skirt with me and didn’t get another one until several years later.

It’s hard to say how much of an impact that black dress in my closet had on me and my current situation, but I can make a fairly confident guess that it was pretty significant. If it hadn’t been there, I may never have discovered the joys of clothing sold in the woman’s department. It started a real passion for it which is something that continues to this day.

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About the Author

Alex Seifert
In many ways, Alex is a typical man who just so happens to enjoy wearing skirts and high heels. He is married to a wonderful, supportive wife and has a young son. His hobbies include reading, programming, metal music, playing instruments, video games, cars, hiking and a number of other smaller things.

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