My dad died earlier this year and please don’t misunderstand, but I didn’t care. I know that sounds horrible to say but he was a terrible, cruel, abusive person. I hadn’t had any interaction with him in over thirty years and he made no effort to be accountable for his abuse nor make any effort to contact me. I’ve had a lot of therapy to come to terms with that relationship and I realized that some people are just evil and their deaths do not warrant mourning.
Wow. Anyway,
I am now fifty years old and I experience a lot of things that people my age experience. I’m tired all the time and I am easily distracted (even more so than usual). Almost every week I learn of someone in my life, whether it’s a neighbor or a high school teacher or a parent of a friend passing away. My mom is pretty healthy for her age but of course we are starting to have uncomfortable conversations about her care and her health as time ticks on.
As people change, it’s not uncommon for the dynamics within that relationship change. They kind of have to, right? They kind of should. You begin to think about the conversations you need tor want o have. And as you’ve probably guessed, one of these conversations for many of us is about gender identity.

I came out to my mom over ten years ago, back when I identified as a crossdresser. Essentially I thought that all of *THIS* was about wearing girl clothes and didn’t realize how much of my identity was entwined with what I wore and how I felt. Since I identified as a crossdresser, that is exactly how I came out.
Looking back, it was strange how she reacted to *that* word. ‘Crossdresser’ is a word that comes with a lot of baggage and most people have a negative/distorted perspective on what it means. To most people, a crossdresser is someone who wears girl clothes for sexual/fetish/kinky reasons. Many people don’t really care to know about what arouses someone else, so when you come out as a crossdresser, it kind of sounds like you are telling someone else what makes you horny.
And to be fair, I don’t want to know what makes other people horny either, lol. But since the word ‘crossdresser’ comes with that weight we often have to clarify that crossdressing isn’t necessarily always associated with arousal.
When I told my mom I was a crossdresser I braced myself for THAT conversation. I was ready to deconstruct that interpretation of the word. But given her reaction, I don’t think she had ever heard the word before. I had to explain what it meant.
It was like “mom, I’m a crossdresser” and she responded with “Okay. I don’t know what that is.”
Which was a relief in a way. Oftentimes when we come out we have to first talk about what crossdressing ISN’T before we can talk about what it IS. Because of this, I could more or less dictate the narrative of who I was and why I am who I am (as best as one can).
Long story short she was… fine about it. She didn’t ask too many questions and we don’t talk about it. I’m glad I came out buuuuut I wish I had waited. What I mean is that it didn’t take much time after the conversation until I identified as transgender. I feel that if I came out as transgender I would have been able to have a very different conversation about my gender identity as opposed to just wearing girl clothes.
But that ship has sailed and it is what it is. I had thought that by coming out to her a lot of things from my formative years would have made more sense but apparently I was better at not getting caught than I thought I was.
Time gives us perspective and allows us (whether we want this or not) to reflect on what we should have done or not have done at different points in our lives. Sometimes we realize that we did or said the right thing, other times, well, not so much.
For the most part I like this. When I come to terms with moments in my life I feel like I am given a second chance to go back and have conversations with people in my life. Oftentimes these moments lead to an apology for what I said or did. I like making peace with people.
For good or for bad, our parents’ perspective and opinions and teachings (whether intentional or not) will shape us. And yes, we are often shaped by our parents’ beliefs when it comes to gender. I was raised in a home where BOYS DO THIS and GIRLS DO THAT. Some of these expectations were influenced by societal beliefs at the time (not that they have changed that much), but parents often pass on the generational teachings of their own parents.
It’s not happening fast enough but the world’s understanding of gender not being binary is evolving. I like to think that we are more enlightened than we were fifty years ago.
But back when I was growing up, it was very much BOYS DO THIS and GIRLS DO THAT. Even back then, I thought gender as a binary was silly and there didn’t seem to be any real reason why a boy couldn’t wear a dress. Yes, I know it wasn’t common but I didn’t think there was anything wrong with it. I did know that what I wanted to wear (and what I wore whenever I had a chance) needed to be a secret.
I didn’t have the maturity or experience or awareness to talk about who I was back then. It took a lifetime to gain that.
As my mom gets older (and as I do the same), I am thinking about what I wish I said to her during my childhood when it comes to who I was. Of course, I didn’t know then what I know now and I would not have been able to find the words to convey how I felt then in the same way I can now.
As I said earlier, I was apparently better at not being caught than I thought I was, but that fear was always there. I am fairly certain that if I had been caught wearing my sister’s dress it would have been very, very bad, especially if my dad was the one who walked in.
I also said that I feel that our perspective on gender is evolving and it’s my hope that a parent learning their son liked to wear dresses would have a different reaction today than my own parents would have likely had all those years ago. My assumption is that parents today would likely turn to the internet for clarity, guidance, and answers, in a similar way that our partners probably do when they learn about this aspect of us.
I wrote a very long post about the common questions our partners have when it comes to crossdressing and gender and I think a similar post about my experiences as a boy who wore dresses could be helpful to parents who have kids who are and were like me.
I do want to clarify that like everything else I write, all of this is from my own perspective, feelings, and identity. I feel that there are enough commonalities among non-binary people that what I write about is relatable to others like me, but I don’t think that I am the only or definitive voice when it comes to all of this.
Okay, let’s go.
I know I need to keep this a secret, but that makes me feel ashamed about a part of me that brings me happiness
I am new to this world and there’s so much I am learning. There are rules that make sense when you teach them to me, but some rules seem to exist “just because”
I don’t know why I wear dresses, I know I just want to and I like to
I don’t know if I want to be a girl. I am just a kid
A dress is just clothes. Why are you so angry?
I’m not confused, I am trying to figure out who I am
Please don’t tell anyone. I know a lot of people will think that I’m weird
I don’t know if I’m gay. I’m just a kid. I’m probably not anything yet. I don’t know if I am transgender. I’m just a kid. I don’t know that word yet
Please don’t be angry. I’m not who I am to make you angry
Sometimes I don’t want to be who I am, but this isn’t going away
Please understand I am embarrassed right now
I know this isn’t “normal”. Believe me, I know this
Please don’t tell dad
I don’t know what this means either
You can tell me to stop, you can punish me, but I will never stop wanting to be true to myself
I know you probably don’t like this but this is a part of me and it’s the same thing as not liking who I am
I’m sorry that I am this way. It’s not easy for me either
Regardless of someone’s gender, we are all on a journey. We are forever learning and adapting to different expectations and rules and norms. We are reminded of this whenever we start a new job. We learn how things are done and who we need to report to and we learn about the office culture and the hierarchy. So many things at a new job seem arbitrary and pointless until we learn WHY things are done that way. When we learn the WHY of anything the written AND unwritten rules make sense, even if that rule is “we do things this way because that is how we’ve always done things” or, even worse, “we do things this way because the boss likes it when we follow his seemingly pointless rules”.
When I was discovering this part of myself there were so many things I was taught (directly and indirectly) about gender. I still remember the complete confusion I felt when I was told that boys don’t wear lipstick. I was only five and I was accustomed to rules based on age, such as I wasn’t old enough to do something, but lipstick? That was the first time I wasn’t allowed to do something because I was a boy.
Again, I was never “caught” when I was a kid and that has seemingly been the case throughout my entire life. To be clear, it’s entirely possible someone knows about all of THIS that I am not aware of, but if so, they’ve never told me that they knew. Perhaps they have the awareness to know that I would prefer to keep this side of me to myself.
When I say “caught” I mean that no one has walked into a room and saw me trying on a dress. And for the record I HATE saying “caught” as it implies I am doing something illegal or immoral or just wrong.
Since I have knowingly never been caught I have no experience in what I would do or say in a moment like that. I suppose like most things my words and actions would be based on that person’s reaction. I would likely react differently if they laughed at me or if they were too stunned to speak. Who that person is, and my relationship with them would also likely be a factor.
I’ve no idea what my life would be like now had I been caught. Again, it would likely be shaped on who caught me. My dad catching me would have been a very different experience than my mom, I think. My dad would waste no time ridiculing me (and worse) and my mom would do everything to keep it a secret from my dad and really, REALLY, make it clear that I can never do it again.
I’ve never felt ashamed about who I am, but I think I would be susceptible to that. Again, if my mom caught me I think the shame would have been intense.
To be clear, my mom always did her best with raising me. She raised me decades ago when the world was different when it came to gender identity. She also lived in fear from my dad and I think she would have looked at keeping my wardrobe preferences as a secret to protect me from him. She knew that she had to keep a ;pt of things from him that would send him into a violent rage.
I don’t know if I had the mindset back then to “predict” what would/could happen if I was caught. All I knew for sure was to keep this a secret for many of the reasons I listed above. I suppose if I had the capacity to do so, I would have hoped for support and love, the same things we hope for when we come out to our partners.
I suppose we don’t really change in that regard. No matter where we are in life or in our journey we just want to be loved and not made to feel that who we are is wrong.
Kids don’t look at THIS the same way parents likely do. They see their son in a dress and they start to wonder (and possibly worry) that their son wants to transition and/or they are gay. Kids probably aren’t thinking about what THIS means in the same way their parents are. I never thought about whether or not I liked boys or girls when I was six years old. I certainly never associated who I was attracted to with what I wore.
So, how should a parent react? I don’t know. I will never experience learning that my son wears dresses so I can’t talk about this from my own experiences. I can only talk about what I wanted and needed and knew when I was young.
Additionally I know how certain reactions would have likely shaped me as I grew up.
Here’s what I know for certain:
No matter how my parents reacted to this, I would have NEVER, EVER stopped being who I was.
They could have punished me, they could have shamed me, my dad could even have beat me, but I would have never stopped. Sure, I may have been more careful and resisted as much as I could, but I promise you that as soon as I moved out I would start/continue wearing whatever I wanted. Afterall, that’s exactly what happened. After I signed my first lease I bought a bra and matching panties before I bought any other household essentials.
Well, I thought they were essentials.
The only other thing I know for certain is that I would have resented my parents if they had “prohibited” me from crossdressing.
If you have a son or a nephew or a cousin or sibling or a friend or even a partner who is like me, they are probably going to be who they are for the rest of their lives.
Sure, they may not grow into someone who is like me. Not every boy who wears a dress will identify the same way that I do, but if I could tell parents one thing is that this is (probably) not a phase that your son will grow out of.
And I don’t think they need to. Regardless of societal norms, kids and adults should be who they are. I wish I had grown up with parents who believed that. I wish that the only thing I knew for certain growing up wasn’t that I need to keep this a secret. I didn’t know WHY I was who I was (and am), all I knew was that no one can ever know.
How we are raised and what we are told will shape us for the rest of our lives. There are still facets of my personality that I can link to an element of my childhood. Parents do not have an easy life and they face moments that they are not prepared for. I don’t know what it’s like to raise a child like me and for those who are doing this very thing I know discovering this about your kid isn’t going to be easy. I know you want to do the right thing but the parenting books probably aren’t helpful. You are raising a kid in a scary world that insists on arbitrary gender norms that don’t make sense to people like me.
But.
Knowing this about your kid is getting to know your kid on a level that is personal and special to them. They are going to be who they are anyway.
Love, Hannah