Showing My True Self
I’m a trans woman. I did a boudoir photo shoot. In Florida.
There wasn’t much traffic as I pulled into the mostly-empty parking lot along Adams Street in downtown Jacksonville. I parked my rented Kia Soul in a space close to the building further up the street, jumped out to go pay the parking fee, then came back to my car. For some reason, I didn’t really want to stay exposed on the street for too long; perhaps I was self-conscious of not having worn makeup that day. Or perhaps too self-conscious of who and what, and where, I was.
I grabbed my phone and left the car again. It wasn’t yet 9:00 AM, but I walked over to the nondescript storefront with its white-covered windows and the sign hanging by the front door: “HYPE Girl Boudoir.” I snapped a photo of it, then went back to the car and posted updates to Facebook and Instagram:
And here I am…going where very few of us have gone before. This was the reason I came all this way. I’m confident that Tiffany and her crew will take good care of me! Time to make some history! 😍
And I waited until close to 9:00, then I left the car, took the small suitcase that I’d picked up at the airport baggage claim the previous day, walked to the front door, and stepped inside.
Ten years ago, I had only a vague conception of the person I would one day become.
Back then, I was a mere crossdresser, who was only barely getting herself out into the world, mostly to attend support group meetings at the Gender Identity Center of Colorado. I’d only come out to the woman who I was then engaged to the previous October, and had managed to grow a bit in that time. It was March when I started attending the support group meetings, at the suggestion of my online friend Bree Wagner (now Lt. Col. Bree Fram, USSF). Eventually, I would take over as the group’s facilitator…a path which would lead me in other directions entirely.
I had a presentation that was passable, having been called “ma’am” on several occasions by then. I had my name, albeit with a different last name from the one I was born with, to minimize the connection between my “selves.” I had a small presence online, via a Facebook account, a Gmail account, and a presence on the Crossdressers.com forums. I had a voice, unlike many of my sisters, which I’d practiced by singing with female vocalists on the radio. And I had a desire to function in society as a woman.
It took until 2016 for me to realize what was really going on, in an epiphany that hit me after having attended my youngest brother’s wedding as Amy: This is who I really am. And it took about ten months from that epiphany to my “Naming Day,” July 20, 2017, when I legally assumed the name and gender marker I use to this day.
Even then, I still had more growth as a woman ahead. I had started hormone replacement therapy the February before my legal transition, and, as time went on, it had its salient effects on my body and mind. Before transition, I had won one crown in the annual Pageant of Majestic Hearts of All Colorado; afterwards, I won another, and then the pageant owner, Phyllis Rogers, by then a close friend, appointed me to the organization’s board of directors. I had changed jobs, apartments, and cars; there were few regular reminders of “his” life left in mine now. And I had discovered a talent for karaoke, which gave me both minor celebrity status in the local community and a fun activity to engage in while traveling.
But this was something beyond all my previous experience.
I’d never seriously considered the idea of boudoir photography. How could I possibly measure up to the lovely images I saw displayed in their advertisements and VIP groups?
A friend of mine had added me to the VIP Facebook group of a boudoir studio in Fort Collins, but, one day, in response to a post on there, I expressed my doubt that I’d ever be a customer, and wound up leaving that group in tears. It would be at least a year before another friend, who I’d met through an online women’s wellness program, added me to another group, the “Hype Girl Boudoir VIP Babe Cave.” The studio’s owner and primary photographer, Tiffany Joyce, emphasized her studio’s inclusiveness: “Boudoir is for everybody. Every woman deserves to feel beautiful. Beauty is not one size fits all.” Neither she, nor any other woman in the group, objected to my status as a trans woman.
So, in December 2022, in response to her studio’s Black Friday sale, I took a leap of faith and put down my money.
Of course, the studio being in Jacksonville, Florida, and me being in Denver, Colorado, necessitated travel.
I was no stranger to air travel as Amy; I’d taken my first trips as my true self in 2019, a business trip to Boston followed closely by a trip to Los Angeles to participate in a summer-camp style competition for lesbians. Since then, I’d been several places by air, even Miami, where I’d gone in October 2022 for a cruise.
I’m well-prepared for air travel, with full documentation including a passport, TSA PreCheck, and good-quality Travelpro luggage. This would be a quick jaunt; I’d fly in the day before my session, then fly out the day after. Maybe I’d even be able to squeeze in some karaoke before I left.
I spoke to Marcella, Hype Girl’s highly efficient and friendly office manager. I booked my session for May 31, working around both the Majestic Hearts Pageant earlier in May and Denver’s PrideFest in June. I booked my flights on Southwest for the days around it, lined up a hotel room at a local Ramada and a rental car with Budget.
Then things started getting dicey.
I won’t detail here the complete sins of Florida’s current governor, Ron DeSantis (aka “Ron DeSatan”); they’ve been amply documented elsewhere. Suffice to say that, in pursuit of the Republican nomination for President and desperate to steal mindshare from Donald Trump, he’s been pushing measures that make Florida a very unwelcoming place for LGBTQ+ people. So much so, in fact, that organizations like Equality Florida have issued a travel advisory for their own state. The Human Rights Campaign has also issued a travel advisory. On journalist Erin Reed’s Anti-Trans Legislative Risk Map, Florida shows in black, with a legend of “Do Not Travel.”
And here I was, ready to go straight into the Belly of the Beast.
This just fed into my sense of determination; in the process, I began to write down my thoughts in a document I called “Finding My ‘Why’.” I wrote some intro paragraphs about my original booking of the session, my background, and the current political state, then added:
That is, ultimately why I want to do this: To show the world that transgender women can be as beautiful as any other women. To humanize us in the eyes of others.
Yes, this is a political statement. But, in this day and age, let’s face it: My entire existence is a political statement.
This is why I want Tiffany to write about my session on her blog, complete with pictures, as she has written about other women who have had sessions with Hype Girl. When she does, I will publicize that far and wide. This may open me to criticism from the very people that are trying to persecute us; I accept that in advance, and trust that I will remain secure here in my home.
And I ended the document with a quote from Cameron Frye in the movie Ferris Bueller’s Day Off:
“I gotta take a stand. I am not gonna sit on my ass as the events that affect me unfold to determine the course of my life. I’m gonna take a stand. I’m gonna defend it. Right or wrong, I’m gonna defend it.”
Truth be told, my trek from Denver to Jacksonville was fairly uneventful. There was a brief layover in Nashville, so brief, in fact, that I had to step quickly to make the boarding time for the next leg. (Tennessee is also fairly hazardous, but I wasn’t there long enough to attract any attention.) And so, in Jacksonville, a lady in a casual dress and flats got off the plane, computer bag slung across her body, towing her flight case behind her.
As I walked towards the baggage claim area, I heard someone off to the side say, “Oh my God, look at her, she’s gorgeous!” I glanced left; there was a group of young ladies walking the other way, one of whom was looking straight at me. And here I was, travelworn from a long day, just trying to get my other suitcase and my rental car. Hmm…maybe there’s hope here after all?
Neither picking up my small suitcase — packed with the lingerie and other items intended for the photo shoot — nor claiming my rental car were particularly eventful. The Kia Soul pleased me; Phyllis drives one, and I’ve driven her car before, so I knew what to expect. I paired my phone to the car, set the radio to Easy 102.9 (a radio station I’d researched before the trip as being to my tastes), and headed off down I-95 to my hotel. Jacksonville traffic was kind of crowded, but no worse than Denver at that hour, to say nothing of the California freeways I’d learned on.
I did very little else that day, going out for a time to ascertain the studio’s location and see more of the area. I ordered a local pizza via DoorDash, which actually fed me for both the nights I was there. And I set my alarm to wake up early enough for the session the next morning.
Walking in, I was greeted by Tiffany, her hair and makeup team, and her social media manager, who was there as Tiffany and I had discussed at my consultation. They got to work on me soon enough, with me facing away from the mirrors, but towards a massive ring light and an iPhone camera. As the hairstylist worked on my hair, the makeup artist began preparing my face. It was a cheery session, which lasted about an hour. The makeup artist even glued false eyelashes to me; it was the first time I’d ever worn them, despite years of drag performance experience.
Then came the moment of truth; they handed me a mirror with which to examine myself. I was utterly amazed at the results, turning myself in the chair to see myself in the larger mirror. My makeup was perfection itself, and my hair had been curled in cascades sweeping off the sides of my face. I snapped a pair of selfies, and posted them to Instagram, captioning them, “Look at me! I’m all HAWT! 😍😍”
Then I opened the suitcase that I’d brought with me. Inside were a number of lingerie sets, each sealed in its own plastic zip bag. I’d spent time a couple of weeks before taking selfies of me wearing each one and getting my soon-to-be-girlfriend’s opinions on each; only the ones we both agreed were good actually made it into the suitcase. Also present were a pair of black Naturalizer heels found on eBay, several pairs of Hanes thigh-high stockings purchased on Amazon, and a Shure wireless microphone…one of my own, that had a damaged capsule from being dropped at the 2022 Majestic Hearts Pageant, yet was still usable as a visual prop.
I laid the outfits out on the bed, and Tiffany and I quickly went through them, whittling them down to three, plus two that we weren’t able to decide on. I had four outfits coming, but, if I used my free perks correctly, could stretch it to five. Meanwhile, we decided we’d start by using the other three. Tiffany locked the front door to the studio, and I unselfconsciously stripped down and found my first outfit.
Tiffany had me stand against a black background in the rear of the studio for the first set, in a red babydoll and thong that probably came from Shein. She also had me wear the heels, which was a bit awkward as I don’t usually wear heels much, and was a bit out of practice. For some shots, I held the microphone, making this kind of a “pop princess” photoshoot. She pulled in other props like a stool and a set of colored lights as needed, making it look like I was on stage. I complied with her posing instructions as best I could, and she snapped picture after picture with her professional camera.
Following this, I changed into a black lace bodysuit from Torrid, and added a pair of black stockings. We moved to a large leather chair in the studio, where I was posed in a variety of positions, including lying “backwards” on the seat with my legs up on the chair back, and seated on the ground leaning against the chair. She then had me change into a delicate pink babydoll set and move to the bed for a variety of positions sitting and laying down.
As we came to this point, we were both so enthusiastic, I decided that I would go for the extra-outfit option, and we’d use both of the outfits we were having trouble deciding on. My fourth outfit, a babydoll with a multicolored floral bodice and pink skirt, served for a series of photos around, and in, a large iron bathtub. Finally, I donned a black babydoll set with an iridescent bodice, from Cacique by Lane Bryant, and we took pictures up against the teal wall of the studio, as well as a few last photos seated on the foot of the bed.
After changing back to my regular dress, I gave Tiffany time to edit the photos and walked a couple of blocks down Adams to a restaurant called Jumpin’ Jax House of Food. The atmosphere reminded me of a couple of restaurants in Boulder where I’d eaten lunch while working at my office there. I ordered a chicken Caesar salad with light dressing and a Coke Zero, then ate while skimming my social media. Finishing my meal, I dropped a $5 bill into the register-side tip jar, then walked back to the studio. I felt more at ease outside with proper makeup, and no one I passed commented on me at all.
When I came back to the studio, it was time for “the reveal.” Tiffany set up her laptop to display a gallery of my images, and handed me control so I could page through them, with the display echoed onto a larger screen in her back room.
I was simply amazed! The images were more than I’d ever dreamed I was capable of! I paged through them, pose after pose, and saw that Tiffany had made me look as gorgeous and sexy as any cis woman. My goals had been met, with flying colors!
I had elected to purchase a full digital gallery plus downloadable copies of the images, and, as another free perk I was entitled to, opted for a retro viewfinder (just like the old View-Masters) with a photo disc containing eight of my best photos, as a gift for my girlfriend. We made the final arrangements, and I departed the studio for my car.
The rest of the day was a bit more of an adventure. I dropped in at the headquarters of Beeline, the company I had worked for at the time of my transition. I had hoped to see CEO Doug Leeby, who had been so nice to me when I transitioned, but, sadly, he wasn’t there, so I left word I’d dropped by. That evening, I changed into a fancy Torrid skater dress, then headed for Mc B’s Lounge, where nightly karaoke was an attraction. The bar was kind of divey, reminding me of a bar in Las Vegas I’d sung at. I sang five songs there in all, including my “signature” number, Sade’s “Smooth Operator.” I also spent much of the evening with an older gentleman sitting next to me, and clearly trying his best to hit on me. I stayed gracious and polite the whole time, never letting on that I was trans or a lesbian, even agreeing to dance with him a couple of times. He walked me to my car as I retired for the evening, and I kissed his cheek before I left. He had played his role well that evening, as I played mine.
The following day, I flew out from Jacksonville. While on a layover at Chicago’s Midway Airport, I received word that my photo gallery was ready. I set my laptop up with a wireless connection through my phone and opened the gallery page. All the photos were there, over 160 of them. I scrolled back and forth, looking at the photos, thinking to myself, “You did it…you crazy bitch, you actually did it.”
Sadly, my girlfriend broke off our romantic relationship before I could receive the viewfinder I’d ordered, which now sits in my closet awaiting another use, possibly another girlfriend. But I still had all the photos, downloading archival copies soon after I got home. I used some of them to revamp my standard profile picture and my social media pages, especially the “pop princess” ones. And, as promised, Tiffany released an extensive blog post of my session, which I promptly publicized far and wide. I kind of wish she could’ve mailed a copy to DeSantis’ office, with a nice big “f**k you” from me.
Much of the text Tiffany used in her blog post was written by me, including my overall observation at the reveal: “It’s unbelievable. I think I’ve actually accomplished what I set out to do. I’m as beautiful and sexy as any cis woman that ever stepped through these doors.” And Tiffany added some good words of her own:
Hype Girl Boudoir has always promoted the mindset that boudoir is for everybody and everyBODY. We’re here to make you feel beautiful, powerful, and worthy EXACTLY as you are. We’ve also always been LGBTQIA+ allies and have been advocating that love is love, everyone is deserving of happiness and acceptance, and that everyone WILL be loved and accepted at our studio.
Would that more Floridians had her mindset.
Would I ever do it again? Possibly…but before I do, I’d like to have my gender confirmation surgery, just so I feel even more authentic going in.
Would I recommend it to other trans women? Without question! If there’s one thing worth braving the travel advisories against Florida for, it’s this. It’s certainly an adventure I’ll never forget.
