It’s Never Too Late

“I wish I had done this sooner.”

We hear this a lot. We SAY this a lot.

*This* can be a lot of things. For some of us we wish we had transitioned sooner. For others we wish we had come out earlier or accepted this side of ourselves years ago.

It’s easy to think this. This side of us, whether we are taking estrogen or wearing whatever we wish to, does come with a lot of anxiety, stress, and tension. And! It also gives us happiness, peace, and joy.

Wishing we had done *this* (whatever *this* may be) sooner is often triggered by thinking of the time lost when we could have been who we are. For myself, living full time identifying and presenting as one gender isn’t the right decision for me. I can’t imagine ever wishing to transition, or wishing I had done so.

I have always tried to be true to myself, even though I’ve had to suppress and hide this side of me for most of my life. Although I’ve gone back and forth on this, ultimately I don’t regret coming out to more people throughout my life. I am content with how I live my lives.

If anything, I wish I had been… hm, well, braver isn’t the right word, but maybe it is? When I was in my late teens I had a freedom that I never had before. Once someone gets their driver’s license and has access to a car their world opens up. I could go anywhere. I could go to any store. And I did. It didn’t take long for me to start buying my own panties.

Although I was mainly drawn to lingerie when I was younger, beautiful dresses were still irresistible. In high school I would listen to my girl friends (girl friends, not girlfriends) talk about prom or another formal dance. They would go shopping together looking for their dress or which heels they would wear. This drove me crazy. My imagination, my jealousy ran wild.

Oh, how I yearned to be a part of that.

Please don’t misunderstand. I never felt like I was born in the wrong body. No, I just felt anyone should wear whatever they wanted to. And my God did I want to wear a beautiful, floor-length gown that glittered. Waaaay more fun than renting a tuxedo.

High school prom and graduation came and went. These are two of the first significant milestones we experience. High school graduation is the unofficial start of our adulthood. We may go out to college, we may enter the workforce, we may finally move out of our childhood home. Moments become memories and we finally understand the saying “you can’t go home again”.

It’s natural to look back and daydream about how different things could have been if we had only done something, said something than what had actually happened.

When I graduated from high school I realized that any chance of being crowned Prom Queen was gone. I mean, I didn’t think it was even a remote chance, but still, I had fantasized about shopping for a dress and the perfect matching heels. Strutting into a ballroom and feeling like a princess.

I still fantasize about this.

In college my world opened up a little more. I was in a new school with hundreds of people I had never seen before. I met people with very different backgrounds and experiences than I did. For some people, college is the first time they are no longer living in the town they grew up in. There’s a freedom, a reincarnation, a rebirth with starting to live the life you had dreamed of. And college can do that.

Sometimes on campus I would see two girls holding hands, or a boy with nail polish. These sights aren’t that uncommon in the year 2022 but in 1994 it wasn’t something you didn’t see every day. But the impact on me was significant. When I was in high school gay people were cruelly mocked and ridiculed. But in college people didn’t really seem to care. I suppose some of my classmates were too hung over or stressed about an exam to give someone else a second thought. 🙂

Naturally I had started to think that maybe being a little more open about who I was wouldn’t be the world-ending experience I had always feared it would be. Maybe it wouldn’t be that big of a deal if I wore a skirt on Halloween at my college.

But like my high school days, soon college was behind me. I was never Prom Queen, but I was also never a princess on Halloween.

And yes, a lot of THIS is about clothes.

We are about halfway through April and when I am at the mall I am seeing teenage girls going from store to store looking at prom dresses.

My God that sounds so creepy to say that.

I can’t help but think those days are gone. I mean, there’s really nothing stopping me from buying a prom dress now, but I think you know what I mean.

It’s… normal for a girl like us to experience a kind of… hm, I don’t want to say puberty but I think for some of us we go through a period of buying clothes that are MAYBE a little too young for us. Clothes we wish we had worn when we were teenagers.

As a middle-aged t-girl I do my best to dress for my age. And I think I do well most of the time. Of course there’s also the mentality of ‘wear whatever you damn well want’ but I digress.

In college it was normal to see “sexy schoolgirls” on Halloween. And goodness did I want to be a sexy schoolgirl on Halloween. And yes, I COULD still be a sexy schoolgirl on Halloween (or any holiday, really) but… that look isn’t really ME, if you know what I mean. If I had the confidence then that I have now, then yes I would have totally been a sexy schoolgirl, but I wasn’t ready to be who I am back then.

I don’t have any regret or misgivings about my gender identity or the decisions I’ve made. I do wish I had the perspective and courage then that I have now.

Love, Hannah

P.S. On the plus side, I couldn’t afford a beautiful floor-length gown when I was twenty but I can now, lol.

5 thoughts on “It’s Never Too Late

  1. I wish everyone felt free to dress however makes them feel comfortable, happy, strong, beautiful, glamorous, fun – whatever it is that clothing and style means to them. It’s so unfortunate how we feel the need to box and confine people with something as personal as how they express themselves, which doesn’t affect anyone other than the person choosing how to dress. I hope it’s okay to post this here, I did a podcast on my friend Charlie, who was so beautiful and dressed in diamonds and tiaras – and he taught me to be fabulous and comfortable in my skin. It’s a tribute to him, and how sad it makes me when people don’t accept others as they are, as I learned his family hadn’t accepted him (after he died).

    Liked by 1 person

  2. Well let me just say as someone who’s gender fluid and works for an open an diverse company I do dress feminine many days
    I don’t wear dresses to work or skirts but I do wear makeup and jewelry and almost always gender neutral female clothes
    So yes I do wear whatever I want and it is freeing
    Sure I get a few looks and most likely talked about behind my back but I’m 61 now and I really don’t care,
    I am who I am and will not look back


  3. I often look back at what I might have done, but more often my regrets derive from the real life consequences of some impulsive and ill-advised choices and actions. Wistful thoughts of what might have been don’t merit regret. We have only so much time and most often we must live within circumstances beyond our control. But we cannot undo the consequences of bad choices and destructive acts. At best we may learn from such regrettable episodes.


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