Taking the Next Step - Goals and Challenges for 2020

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 2020?

Love, Hannah


13 comments


  • Stevie

    Hannah I love you articles! For me 2020 my goal is to keep moving forward in being true to myself; moving forward with my desire to dress the way i want when i want if i want. I m a closet dresser but i dress in some femme garment everyday, last year I added make up.
    I dont go out “dressed “ but i do wear womens jeans sweaters and panties and bras. I wear toenail polish .
    Thats as far as I want to go. It fits my
    Demisexuality perfectly
    Thank Hannah
    Wear something pretty today I am


  • Paullette

    I came across your website entirely by chance a week or so. I was impressed by the quality of the clothing and the sincerity of the information under the Learning Center tab. In solidarity of this community I have purchased a few items.

    My life's path is very similar to what your members have reported. I have been dressing for close to 55 years and have experienced the ups and downs as others have mentioned including the dreaded purging of precious articles of clothing and accessories. In the day to day routine of daily life, I am a 'good old boy', husband, father,…. Over the course of my life I have really wondered/struggled about the uncontrollable urge to dress, the associated guilt and the euphoria related to the process of shopping, dressing, sanity of all of this, etc.

    A few months ago, after a particular nasty purging process I came to understand that my feminine nature was truly a permanent fixture. Since that time I have come to the realization that for me my feminine side is just who I am and I have decided to absolutely embrace her (I mean, whats not to like?) I believe that a big help in my acceptance of this is the information available these days through the internet which shows that our community is fairly common and widespread (but underground). I wish this information had been readily available in my younger years as I would have pursued my femininity more seriously than I had. My advice to younger folks is to follow this passion whole heartedly and to enjoy all that it brings.


  • Hannah

    @scott

    Thank you! You are always the right age to be who you are and to wear what you want.

    Love, Hannah


  • Hannah

    @wilbur

    We all have different journeys and we will all do different things when we are ready to do so. You may not be ready now, and that's okay. It's important not to rush into something you're not ready for. You'll get there and I'm proud of you!

    Love, Hannah


  • Wilbur

    I'm just starting out and I've wanted to do this year's ago but I don't know if I will be able to go out yet I have seemed like I should have been a female baby girl ever since I was born . But I grew up and made a family of my own and having 10 children 5 boys and 5 girls only one knows about me how I am feeling to be and she gives me her love and tells me as long as your happy dad .I did play dress up with my brothers and sister when we were Young and life wasn't as judging as it is now but anyway I have always wanted to be


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