Taking the Next Step - Goals and Challenges

I know its a cliche but I love a fresh start. I love being able to begin again, I love starting over. I love a challenge, I love setting goals.

I love taking the next step. In stilettos, naturally.

It doesn't seem like that long ago when I would go to the mall and avoid glancing over at the lingerie sections of a department store lest someone figure out my secret. I am not sure when I found the courage to do so, or where that bravery came from, but one day I bought a pair of panties and never looked back. I never thought I would do anything more fearless than that, but fast forward a decade (or two) and, well, here I am.

I look at my photos and I look at my wardrobe and it all looks so easy. These days I never think twice about walking across a parking lot to a salon for a makeover. Strutting through the mall in four inch heels? Easy peasy. Bra fitting? No problem.

But what's next? Ten years ago if I looked at what my life is like today I would have thought I wouldn't want anything more. As I become more confident and comfortable living a double life (if you will) and having two gender identities, I've wanted to do more "everyday" things. At one time going out en femme meant visiting a LGBTQ+ bar or a drag show. Then progressing to a coffee shop owned by a trans woman. Soon I was attending support groups for transgender women. Going out en femme meant going to places where a girl like me wasn't unusual. But after limiting myself to these types of places for a while I began to grow restless. I wanted something new. My confidence grew, I was comfortable being out in the real world, and I wanted to experience more than what I had already done.

I started to list all the places I would go if I were brave. Shopping at the mall, getting a makeover, that cute store in Minneapolis that sold amazing dresses, having coffee, going out to dinner. And then one day in June... I just did it. The first time I went out en femme during the day was an experience I will never forget. Too excited to sleep, I woke up early and got dressed. I wore a cute pastel tank top, a black cardigan, a skirt with a floral pattern, black stockings, and black stilettos. As nervous as I was, my eyeliner looked amazing despite my trembling hand.

Before I had a chance to talk myself out of it, I was in my car and on my way to a coffee shop. I drove about twenty miles away from where I lived to hopefully avoid anyone I knew. I parked my car and walked about two blocks to get my coffee. I will never forget the sensation of my heels on the sidewalk, the wind through my long, black hair, the rising sun warming my body. It was a new day... in more than one way.

I took a deep breath and walked through the door of the cafe. The baristas smiled at me... and it was sincere. I ordered my coffee, gave my name(!), and waited with the other early risers for my latte. After getting my coffee, I realized I had accomplished something amazing. Yes, this was something I did many times in male mode, but this.... this was different. It was a high heeled step into another world.

Bursting with pride and confidence and acceptance, I walked into the small upscale grocery store next door to the cafe. My heels clicking on the floor, the clerks looking at me (but not staring at me), and everyone (including me) just going about their day. It was bliss. I had been so afraid to do this, but strolling through the produce section of a grocery store on a Friday morning felt like a new beginning. I was afraid of people staring, rude comments, pointing, harassment, and worse. But it was a beautiful morning.

Bolstered by the uneventful moments, I decided to make my early morning coffee run into a day of running errands. By the time my day was over, I had visited two malls, two large department stores, more coffee shops (not that I needed more caffeine) and had lunch. I returned home just... glowing. I felt like I had climbed a mountain. I had crossed so many things off of my wish list that day but as the days and weeks passed, I dreamed up more things I wanted to do. And eventually, one by one, I crossed those off my list. Museums, plays, lingerie shopping, dinner at expensive restaurant, Pride festivals, photo shoots...

But as the new year settles in, I am started to daydream once again. What's next? What is left on my wish list? I would love to be a bridesmaid at a wedding. I would love to attend a fancy gala. I would love to fly and travel en femme.

These days I feel I have the confidence to go anywhere en femme. The goals listed above are things I'll do, but just haven't gotten around to doing. These dreams feel... easy. But I love a challenge. I love to push myself in many aspect of my life, and half of my life is the life I have en femme. The idea of going through airport security and hopping on a plane and going to a new city feels like a breeze compared to other goals I have, namely my immediate family knowing me. All of me. Both of me. I have come out to my mom and siblings, but that was years ago. I wasn't who I am then. It's true you can only come out once, but as my gender identity evolves and as I understand myself (and herself) better, perhaps coming out again is the next challenge.

What are your goals for this year?

Love, Hannah


  • Hannah


    That's wonderful! I think it's important to be a part of a community, whether it is trans or cis. We are all women (when we chose to be, that is).

    Love, Hannah

  • Hannah


    I'm glad it helped! Please keep us all updated on your journey. We're all excited for you!

    Love, Hannah

  • Scott

    Hello Hanna! I sooo enjoy reading your articles!! You really inspire me! Wish there was someone like you when I was younger! Keep up the good work and thank you!

  • Hannah


    Amazing! It sounds like you are living your best life!

    Love, Hannah

  • Amyrakunejo

    Actually, I only have one goal. To get far in game development.

    Of course, that alone has little to do with the topic at hand, though the main character (whose name is also the title of the game and the title of the short story the game is loosely based on) is a femme that is proud to have a penis. However, her life is not based on multiple gender identities, but is based on a struggle to defeat the system of hatred and religious debauchery, or at the very least, escape it. Her name is Ramsey, and I expect to have the first demo up on itch.io very soon.


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