A Story of Fitness and Transgender Identification

In 2013, I met John, a man who felt trapped in his male body, desperate to investigate and accept his feminine desires of expression and potentially transgender identification while improving his physical fitness. This is his story… ***
It’s 6 p.m. on a warm, cloudless Sunday in late May, and I’m hibernating on the couch, sprawled out with my dog as little spoon, entranced by the latest episodes of “Keeping Up With The Kardashians” and the Diane Sawyer special on Bruce Jenner and “her”. Because I’ve already gone to yoga and biked the pup around town, I don’t feel too ashamed that I’m missing this gorgeous afternoon; I absolutely must find out all the details of this latest disclosure.
I met John almost two years ago. He replied to my Craigslist ad for personal training. In detail, he described what he needed, his words peppered with apologies:
“I do not wish to offend but am interested in training and dream of finding a trainer who will motivate me through insistence and encouragement to workout in completely feminine attire.  Again, I have no wish to offend but this is a serious goal of mine and once I find the right trainer I know they (hopefully you) will have all the resources they need to keep me going and to become comfortable as I begin to get in shape and learn to get more in touch with my feminine side.”
I had the utmost respect for John. What an unbelievable thing to do: reach out to a complete stranger, from the internet of all places, and be honest about something that causes extreme anxiety.
From the start, I told him, “If we’re really going to do this, you are not John to me, only Natalie.”
We met a few days later. He rolled up in a US-made grey sedan and was dressed as John, his thinning white hair in a short buzz cut, his blue athletic shorts flirting with his thighs, wanting to expose more, but not ready yet.
We did simple fitness exercises: squats, lunges, a few laps, pushups, sit-ups, and it was excruciatingly difficult for him. I wrapped up the scheduled hour-long workout after 15 minutes. But I was hopeful within a month I could build up his endurance. He paid me cash and waved goodbye.
A couple hours later, we continued our email exchange, during which he further explained his predicament. At 61 years old, he had been a public figure in his community for his entire career. Educator was one of his most influential roles. His 6’3″, 250-pound frame is the antithesis of feminine. He’s sturdy, manly, and southern. “No one would ever imagine that I have this interest in cross-dressing. My appearance is quite masculine and that just frustrates my unusual interests even further.” But his insistence on his love for manicures and pedicures reminded me that, yes, this was a man trapped, part of a society that does not welcome nontraditional, (possibly trans) gender identity, particularly north of the city where he lives.
“Complete with bright polish,” he loved “the way manis and pedis look as well as the pampering from the salon visit.” But the joyful experience was ephemeral. Quickly, after each appointment, his “drab masculine appearance” would resurface, stifling all things female. The insurmountable courage it took, in addition to the overwhelming fear felt while requesting bright-colored polish was the reason it had been several years since his last appointment.
His fear of being found out was strong and real. It was tangible even through a computer screen.
Over the years, out of frustration, he’d “simply discard” his entire treasured female wardrobe. Finally, he reached out to someone for help to facilitate this growth and journey toward acceptance and health.
This someone was me.
“I continue to harbor these desires to dress and to be accepted if only by one person and perhaps, if lucky, by a few.  Hence my reply to your posting that I have been contemplating for a couple of weeks since I first saw one of your ads.”
John’s fitness goals focused on greater flexibility and losing weight. He assured me that he was unable to go to a public park dressed as a woman, “at least not yet, if ever.” I knew that would be our greatest challenge to overcome.
How to be a woman baffled him: how to buy clothes (where sales clerks and customers wouldn’t judge), how to put outfits together, how to apply makeup. He wanted a strict trainer who would require that he always dressed entirely feminine when together. As the physical training progressed, John, as I, was hopeful he would become more accepting and enjoy his feminine side.
At 27 years old, the challenge enlivened me. I can really help this person. I knew I could get him in shape, but could I break down his fear? Fear is the greatest limiter.
The next day, after asking for my fashion stamp of approval, he ordered a new outfit online through Target. The package was scheduled to arrive on his doorstep in a week. He also purchased a wig.
That week, he, as John, met me again, exercising for 20 minutes instead of 15 minutes. And then the following week he showed up as Natalie. Hot pink tennis skirt with spandex shorts underneath, a white tank top, a blonde, shoulder-length wig. I was taken aback some. This was new to me, too.
“You look great!” I exclaimed as she stepped from the security of her tinted car windows.
The small neighborhood park was quite bare except for the occasional runner passing through. I could tell the wig was itchy, and just like I do when wearing a skirt, she pulled on the seams at the bottom to readjust. “You look beautiful, Natalie, really.” She smiled, proud yet terrified, uncertain how happy she should feel.
We did a stairs workout. I watched dense sweat beads collect on her brow and roll down, one by one. I felt anxious about her wig getting dirty. I wondered how a person even cleans a wig; do you wash it like normal hair? Fifteen minutes later, I ended the session.
Because she wanted to work on being in public as herself, I thought the best place to start was a grocery store. She was 45 minutes south from where she lived; the store seemed safe. She hopped into her car, and I hopped onto my bike, and we both headed toward the supermarket a half mile away. In the parking lot, I had to practically pull Natalie from the car. “You can do this. No one knows you here. Seriously, no one is looking at you, people are way too concerned with themselves.” We took a deep breath together and she hesitantly walked toward the entrance. Inside, the chill from the air conditioning was refreshing, and again I thought about Natalie’s wig and how hot she must have been. I noticed, for the first time, how bright and exposing the lights were. I noticed how many people do actually stare you down, but no more toward she than they did me.
Ten feet in, Natalie ducked into the greeting card aisle. “I recognized someone, I recognized someone!” she panted. “I can’t, I can’t.” I noticed her 6’3″ frame shaking, uncontrollably, while scanning the aisle for all possible threats. She bolted back through the entrance sliding doors, barely avoided a passing car, and sought immediate refuge in her car.
“I can’t, I can’t.”
“You did really well, small steps. This was huge. No one recognized you. Heck, you
have a wig on.”
We both giggled a little.
When John first emailed, I was committed to getting him fit, feeling and looking good.
But within a week, my job description shifted toward support system, confidant,
therapist. I questioned my aptitude to undertake such a role. But then I thought
about every other client with whom I’ve worked. Every single person requires just as
much physical instruction as emotional support. Whether they are working to not
binge and eat mindfully, or drink less, or dress as a woman, there’s no difference; it’s
support all the same.
That was the last time I saw John or Natalie. He decided he wasn’t ready, decided driving 45 minutes south to meet me was too time consuming, decided he needed to find a support system in his town. He never did.
Sitting on the couch, a year and a half later, I think of John and Natalie, naturally. I reach out, asking how everything is, if he wants to finally schedule that makeup tutorial with some of my girlfriends we spoke about so long ago. He is appreciative and thankful. “Yes, yes, I would love that.” He asks me what I want him to wear: female or male attire? I tell him whatever is most comfortable. She decides on a skirt and blouse.
A week later, on a Wednesday, my friends ready for the tutorial, John emails that he can’t do it. “I don’t have the courage right now.” I don’t push too hard for him to change his mind.
Feeling trapped and imprisoned by societal limitations and ultimately your own is heartbreaking. I work in the fitness industry for similar reasons I am a writer: because it is a unifier, it is truly for everyone. People find their voices, their confidence. I hoped through fitness Natalie could find her voice and embrace her personal desires whether that was cross-dressing or transgender identification. For now she hasn’t, but maybe one day she will.
Did you relate to this blog post? Give it a share on social media, comment below your thoughts and questions, and subscribe to my blog!

Related Post

Why Taking Medication Can Be A Good Thing "If you do not take the antibiotics, you will die," the doctor proclaimed from the foot of my hospital bed. A lineup of physicians—a urologist, an ...
Show Me The Money: How Much Are You Worth? How much are you worth? When I was 7, I started working at my dad's company during school vacations for $3.75 an hour. I'd file, copy, count invoices...
Women Who Date Men Who Don’t Treat Them Well... I used to think women who date men who don't treat them well don't have enough self-worth. I used to think these women don't believe they deserve b...
Not All Who Wander Are Lost Two weeks after my memoir was released, a month before Christmas break, I booked a flight to San Diego, so I could hop on a train for the border, cros...
  • Danielle Krasman
    Posted at 15:49h, 18 August Reply

    Reading aloud to Adam during a road trip. We love how you take us with you through your writing. Xoxo

    • Sabrina Must
      Posted at 23:51h, 18 August Reply

      <3 <3 <3

    • Sabrina Must
      Posted at 20:55h, 20 August Reply

      Love this! Thanks, D and Adam!

  • Dedra Zimmer
    Posted at 12:30h, 26 July Reply

    This is what just what I was looking for. THank god I stumbled upon your website.

  • Php News Script
    Posted at 20:32h, 21 September Reply

    I’m impressed, I must say. Actually rarely should i encounter a weblog that’s both educative and entertaining, and without a doubt, you may have hit the nail to the head. Your concept is outstanding; the catch is something that not enough people are speaking intelligently about. I am happy i always came across this around my seek out something relating to this.

    • sabrinamust
      Posted at 16:38h, 29 September Reply

      Thank you! Keep following along. 🙂

Post A Comment