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Thursday morning arrived with golden sunlight streaming through my bedroom windows—a beautiful day that belied the butterflies in my stomach. I stood before my oversized suitcase, each carefully chosen outfit representing a different facet of the woman I hoped to become over the next few days. The massive bag seemed to mirror my own situation: overflowing with possibilities, yet somehow still not quite enough to contain all my nervous energy.
My hands trembled slightly as I folded another blouse, tucking it between layers of skirts and dresses; this wasn't just packing for a trip, it was preparing for my first real adventure as Katie. Each item carried the weight of anticipation: Would I pass? Would I be accepted? Would I finally feel like myself?
The drive to Sacramento was punctuated by stops at beauty stores for what I called my 'confidence pit-stops'— first Sally's, then Ulta—each small purchase a tiny act of self-affirmation. Every swipe of my credit card felt like a declaration: I deserve to feel beautiful, I deserve to be here. By the time I reached Davis, my stomach was growling and Black Bear Diner beckoned like an oasis.
As I slid into a booth, memories of college days with my roommates flooded in; back then, my most treasured secret was a pair of sky-high black platform heels, hidden away from judging eyes. Now, here I sat, fully presented as Katie, about to interact with a waiter, as a woman, for the first time.
The cute waiter approached, and my heart raced. "What can I get for you, Miss?" he asked with a warm smile. I ordered the meatloaf, my voice higher than usual but steady. After he left, I excused myself to freshen up in the restroom, eager to check my appearance. Standing before the mirror, I smoothed my high-waisted jeans and adjusted my crop top beneath my long-sleeved denim shirt. I had to laugh at my morning's contouring attempt—it wasn't quite Instagram-worthy, but it would do. "At least the lighting in here is forgiving," I muttered to myself. I wondered if the waiter found me attractive.
*******
Arriving at the hotel in Sacramento, I marvelled at the speckled pattern on the marble floor—a beautiful complexity that seemed to mirror my own journey—but that moment of peace was shattered at check-in when the attendant asked for my ID. I handed over my license, the male photo in stark contrast with my current appearance. My heart pounded so loud I felt sure everyone in the lobby could hear it.
"I'm here for a transgender event." I blurted out, my voice a mix of pride and apprehension. The attendant's puzzled frown sent a wave of anxiety through me, but after what felt like an eternity of hushed consultations with a manager—the last thing I needed after a long day of driving—I was finally given my room key and a cookie—a sweet but somewhat hollow, consolation prize.
As I made my way to my room, exhausted and doubting myself more with each step, a question echoed in my mind: "What does it mean to be transgender?" The answer, I was beginning to realize, might be more complex than I'd ever imagined, but as I caught my reflection in a hallway mirror—tired but still unmistakably Katie—I knew that whatever the answer was, I was on the right path to finding it.
The next evening, I stood before the mirror again, this time admiring the flowing polka dot skirt that swished around my legs. It was a far cry from the jeans and crop top of yesterday—this outfit was pure feminine fantasy, straight out of my childhood dreams. I twirled, watching the fabric billow, and for a moment, I was that little boy playing dress-up with my sister, finally free to express the girl inside.
"You've got this, Katie," I whispered to my reflection. "Remember, you can always leave early. Just be yourself and have fun."
The bar at which we'd chosen to meet was a riot of neon and nostalgia, movie star faces beamed down from every wall. As I sipped my Malibu Barbie cocktail—a drink that felt perfectly on-brand for the evening—I found myself opening up to the diverse group of women around me.
"I first discovered Katie when I was playing dress-up with my older sister," I shared, the words flowing easier with each sip. "From that day on, I was obsessed with fashion. I'd dream about wearing gorgeous gowns and sparkly heels, imagining myself at fancy parties in far-off places." I paused, remembering the confusion and loneliness of those early years. "It was hard, you know, being a boy but feeling like there was this whole other person inside, waiting to come out."
Jane, a retired veteran with perfectly coiffed silver hair, nodded in understanding. "The '70s and '80s were a different time," she said, her voice tinged with both nostalgia and a hint of old pain. "In my line of work, being trans wasn't just unheard of, it was dangerous. It took me years to find people like us, to build this community." She gestured around the bar, her face softening. "That's why I come back every year. It's beautiful, isn't it, seeing all of us living authentically?"
As the night wore on, I found myself mesmerized by the beauty and diversity around me. Women of all ages, backgrounds and stages of transition, each with their own story, their own journey; I wasn't alone any more, far from it. Here, in this neon-lit bar, I was part of something bigger, a celebration of femininity in all its forms.
Yet, as I revelled in the sense of belonging, a flicker of uncertainty remained. As a cross-dresser comfortable with both my identities, I wondered where exactly I fitted into this spectrum. Was I transgender? Did I need to be? The lines I once thought clear now seemed beautifully blurred.
As I made my way back to the hotel after the event, my skirt swishing with each step, I realized that perhaps the beauty lay not in the labels, but in the freedom to explore, to express, to simply be; tonight, under the Sacramento stars, I was simply me, and for now, that felt like more than enough.
Katie -
Thank you for sharing your experience and story. I found it to be an inspiration and hope for others.
Personally I've only been out dressed twice - once in college many years ago for Halloween and the other about 5 years ago to attend a support group meeting (I changed when I got there and again before I left). Both times I was nervous. The first time was fun fueled by liquid courage. The second was interesting but felt awkward as I was the only one in a dress and heels and not transitioning. I have done some therapy sessions dressed but get dressed at my therapists office. I do go out in public wearing earrings with gel polished nails, occasionally I'll wear a pair of ankle boots with knee high stockings. My hope is to one day be brave enough to go out like you did.
I hope you have many more opportunities to be out as your true self.
As to the question of where you fit in on the spectrum - you fit in where you feel you do. For each of us the answer is different. I think it is how you feel inside, not what you look like, what you wear or whether you're in some phase of transitioning. I have a femme side that I express in many ways, some obvious others more subtle. Bottom line you be you.
XOXO
Suzanne
Today, I took a deep dive in the other end of the pool. I went to a "chick flick"...as a chick! It was extraordinary-tears running down my cheeks, free of embarrassment... "We Live In Time". For the unsteady who'd like to venture out, this was a Sunday afternoon matinee-cheaper and less populated-practically a private screening, and the hallways were basically deserted. I wasn't gauging reactions, but, by the same token, nobody did anything overt or to interfere.
A beautiful writing Katie. I remember your writing a bit in public photos and admiring your words. I found, in this writing it was very easy to "feel" what you were experiencing. It's so freeing when we get to be out and be alive. Like the mannequin girl from "Twilight Zone's, The After Hours". I hope you will continue writing as It's easier for many of us to find ourselves and be comfortable in ourselves, when we see similar feelings in others like us. Thanks for sharing Katie.
Bonjour Katie...merci for sharing such an inspiring tale. You travels through getting ready, hitting the shops and spas along the way, is so sweet. Suspsence of the ID must have been a "interesting" moment. So much of you story had me rivetted as I keep taking bigger bites of spending more time out as Kyra in the world, (and that event sounds divine). I am, seeking and would love to attend such an event, keep looking for event near by, or where I may be traveling for business/etc.
J'adore your courage & I understand, as without my gf, I'd have much more difficulty going out to a private AH's clubs etc to dans! Will be reading 'it' again: many aspects relate to my shifting life right now despite this isn't new to me, yet I am reaching a new place, new choices. Situational items abound from your words! I look now to how my lifestyle as I am is transtioning to. I marvel at your spirit and strength. It will be sometime I will be in & out of the "androgenous male" mode for certain things I do but am taking bigger bites at being Kyra more, as she is a side I do not wish to hide. Your femme nature shines bright!
Merci for your service and for your comments that relate to our girls side, of caring for our self & making those choices to do so. You look amazingly pretty and I am happy to see your successes in so many ways. The challanges we face in trans, to live out, your story helped me look once more at many aspects of living authentic to us.
Merci beaucoup, ma soeur, portez-vousbien! L'amour, Kyra, ox
Thank you so much for sharing your experience. You do seem to be searching for who you really are, I think you are finding the answer. When I read stories like this it makes me wonder if I could have choose a much different path in life. I am in my mid 70’s, and back when I was young the world was not even close to being receptive. I hope you have a wonderful life.
Thank you telling us your wonderful story.
I love one of the last things you say, "perhaps the beauty lay not in the labels, but in the freedom to explore." This is how I experience dressing. The going back and forth, switching between "guy" and "girl" modes, as I like to say, is part of the fun. I envy you your trip, and wish I could have been there.
Hi Kate, I don’t know if you remember me from that weekend / I’m Jill and we talked a couple of times Friday night at the dinner and I think we just said hi at the Sparkle event.. I remember you well and how scared you were to be out. I thought you looked beautiful and yes you were among friends that weekend and we are all like family. I’ve been going and part of the Gems family for 6 years now and I was just like you when I started to go out all dressed up. Thank you for your story and for having the courage to come out dressed. I have made so many friends here. You will have to go to Vegas next May for Viva Las Vegas, Wildside.. it’s a week long and I stay dressed for the hole week / amazing time
It was nice to meet you & hope to see you at another event
Jill XOXO
Beautiful photo Katie!
I enjoyed reading your post. Thank you for sharing your adventure. Being out and about takes so much courage. It's nerve wracking, and fun at the same time. Congrats on getting out there!
Marvellous story Katie, I hope one day to be able to do the same, a trip of discovery and empowerment, I’m so happy for you
What a wonderful story. Thank you so much for sharing it. It struck so many chords with my own apprehensions when first meeting and enjoying the company of other transgender/crossdressing women. I've never looked back and now have a wonderful circle of friends who share their personal journeys with each other.
Robyn
Hi there KK - This is an interesting story for me on a couple levels. First, I know that hotel you were at in Sacramento very well, having stayed there numerous times in my career in outside sales. I may even have stayed while there was a Trans event going on as I seem to recall spotting a few “girls” here and there when I was a guest. Which I thought was very cool🥰.
Your check in experience seemed pretty routine. No matter how anyone’s dressed you’ll be asked for your ID. Many times they check with another manager and have hushed consultations. Nothing out of the ordinary. And you are in California after all. There can be repercussions for not complying with proper gender pronouns and other things. People can become unemployed there for the smallest of things. Then you got your key and cookie, Your “somewhat hollow, consolation prize.” Yet, the experience you described was identical to one I went through every time I stayed there. In fact I used to stop there weekly even if I wasn’t a guest, and use their nice restrooms and grab a coffee. Once - security asked me - “I see you here every Monday…are you a guest?” I told him sometimes but not now, just restroom break and buy a coffee. He said have a nice day sir. As I got in my car I thought: This place is really on top of things. It gave me a good feeling.
I guess what I’m curious about here is this: When we girls go out in our femme modes - what do we expect? What should have happened different at check in for you Katie? Because I don’t see how your experience was anxiety inducing in the least. Surely we all expect we’re going to be a little nervous at the idea of going out in public? You ate at Black Bear dressed before you checked in…that’s a way bolder move to me.
It was a very well written piece about going out into the maddening crowds. It helps us realize what things we may encounter while out. But it did make me think about what is it some of us girls are expecting from the public? I’m of the mindset that most of the working stiffs out there are trying to do the best they can at their jobs. Most of the time their job is probably pretty routine and boring. A crossdresser or Trans individual entering the premises is certainly going to be a break from the usual and really stand out. That’ll be the dinner time conversation at home that night. “Hey, a trans person came in today….” Shouldn’t we expect that to be the case, allow for it and be okay with it? I know I would be.
Heck, I can imagine myself checking in there as Grace and at the first hesitation where they’re doing a double take when checking my ID telling the person: “Yeah, I’m a dude trying to look like a lady. And then cracking up laughing!”
GP
Great story Katie!
I know the group that put on the event and they are WONDERFUL! Been to a couple of their events, but didn't make it to Sparkle this year. Between the girls on this site, and the group in Sacramento, I have found so much wonderful advice, and courage to go out and just be Nikki!
Thank you for sharing your adventure.
Wow that sounds like a beautiful day Katie!!! I admire your bravery!
-Nat (: