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  • Writer's pictureJessica Jaymes Purdy

Finding My Womanhood: A Journey to Authenticity

You’ll Understand When You’re Older: Feelings I Could Not Put into Words


When I was young, I always gravitated to hanging out with girls. We enjoyed the same things. I understood them in a way that I didn’t understand boys. Being around other girls felt natural and comfortable. Back then, I couldn't quite put my finger on why I felt this way, but I knew there was something different about me.


"Why do I feel so much more comfortable around girls?" I wondered. "Is it just because we like the same things, or is there something wrong with me?"


I struggled to understand why I didn’t like hanging out with boys. I never quite felt like I belonged among them. Many of their interests and behaviors felt foreign to me. I tried to join in, but it always felt like I was pretending, wearing a mask that didn't quite fit.  Sports, fighting, hunting, fishing, none of that was me.


"Why can't I be like other boys?" I asked myself. "Why do I like girl's stuff more than boy's stuff? Why can't I just be normal? Why do I feel more at home playing with doll houses and cooking than I do watching sports and hunting?”


I just didn't have the words to express how was feeling, or the understanding to make sense of it. All I knew was that I was different, that I didn't fit in. As I grew older, these questions became more pressing. I watched as my male peers became more boisterous, more aggressive, more obsessed with proving their masculinity. They roughhoused and played sports, they talked about girls in a way that made me uncomfortable, they seemed to revel in a kind of macho posturing that felt utterly alien to me.


I tried to push these feelings down, to convince myself that I was just a sensitive boy, a gentle soul in a world of rough-and-tumble masculinity. But deep down, I knew there was more to it than that. I knew that my connection to girls and women was something more.


At times I would think to myself, "Maybe I'm supposed to be a girl. Maybe that's why I feel so different, so out of place among boys."


Jessica Purdy as a young child. Jessica looks like a boy with short blonde hair, and plaid shirt and a smile that isn't kind of like Mona Lisa's smile, maybe less.
Jessica Purdy as a young child.

But as soon as the thought entered my mind, I pushed it away. It was too frightening, too far outside the bounds of what I had been taught was normal and acceptable. I couldn't be a girl, I told myself. I had a boy's body, a boy's name, a boy's life. To even consider the possibility that I might be something else was unthinkable.


But even then, as a confused and lonely child, I knew that my comfort with girls and discomfort amongst boys was not just about what I liked and didn’t like. It was a reflection of something much deeper.


And so I kept those feelings, those stirrings of a truth hidden. I wasn’t ready to face them. In truth, society wasn’t ready to face them. I continued to go through the motions of being a boy, I was never really happy.


Teenage Hormones: Confusing Changes and Realizations


As I entered my teenage years, my body began to change in ways that felt foreign and uncomfortable. Hair sprouted in new places, my voice deepened, and my features became more angular and masculine. At the same time, social expectations shifted, and I found myself under increasing pressure to conform to traditional gender roles.


"Why do I feel so uncomfortable with these changes?" I wondered. "Why does it feel like my body is betraying me? All I’ve wanted is to be more like the other boys, to fit in, to belong.  Surely this will help.  But why, now that it’s happening, do I feel like I’m dying?”


I had the opportunity to dress in women’s clothes and makeup as part of a cross-gender fashion show at church camp. For a brief moment, as I looked in the mirror and saw a glimpse of the woman I could be, I felt a thrill of excitement and recognition. But as soon as I stepped out into the world, that feeling evaporated, replaced by a deep sense of unease and discomfort.


"How can I simultaneously feel like these clothes are for me and yet feel like everything about me wearing them is wrong?" I asked myself. "Why do I feel so much worse about myself and my body right now?"


A teenage Jessica. She looks like a young man.  She is cuddling with her girlfriend while two other female friends sit beside them.
A teenage Jessica with friends.

I watched as the girls around me blossomed into young women, their bodies softening and curving in ways that made me ache with a strange mix of jealousy and appreciation. I found myself staring at them, not with sexual desire, but with a deep sense of longing.


"I don't want to be with them," I realized. "I want to be like them. I want a body that feels like home. Am I gay?”


I knew I didn’t want to have sex with men, but my attraction to women was a tangled knot of emotions. I admired their beauty, their grace, the way they moved through the world with a sense of ease and confidence that I envied. But I also wanted to be them, to inhabit their bodies and live their lives.


"What does it mean that I feel this way?" I wondered. "Can I be a woman if I'm not attracted to men? Can I be a woman if I don't feel comfortable in women's clothes? Do gay men all feel like women on some level?”


These questions swirled in my mind, but I had no answers. I felt like I was falling in an abyss.  Like I was trapped in a dungeon searching for a way out, a path that would lead me to freedom. But everywhere I turned, I ran into dead ends and locked doors, unable to find my way to the answers I so desperately needed.


It would be years before I finally understood the truth about my gender identity, before I could put a name to the feelings that had haunted me for so long. But even then, as a confused and lonely teenager, I knew that something was different about me, that the expectations and assumptions of the world around me didn't quite fit. I just didn't know how to make sense of it, or how to find my way to a place where I could be my true self.


Don’t Ask, Don’t Tell:  Figuring Out How to Do Gender.


Jesica Purdy in Army Dress uniform with a tight buzzcut. She looks like an unhappy young man.
Jessica the day she graduated from bootcamp.

When I arrived at my first duty assignment, I was warned not to hang out with the lesbians. But the moment I met them, I felt an instant connection, a sense of belonging that I had never experienced before. They welcomed me into their circle, and for the first time in my life, I felt like I could be myself.


"These women understand me," I thought. "They see something in me that I've been afraid to acknowledge, even to myself."


As I spent more time with them, they began to show me a glimpse of the person I could become. They encouraged me to express myself, to explore my identity, to push against the rigid gender roles that had always felt so suffocating. For a brief, shining moment, I felt like I had found my place in the world.


But then I was stationed in Korea, and everything changed. Suddenly, I was cut off from my emotional supports, from the only people who had ever made me feel truly seen and understood. I was vulnerable, alone, and struggling to make sense of the feelings that had been stirred up inside me.


"How can I be a woman if I don't feel comfortable in women's clothes?" I asked myself. "How can I be a lesbian if I have a penis?"


I tried to push these questions down, to bury them beneath a facade of masculinity. I grew a mustache, hoping it would mask the ways in which I didn't fit in as a man. But at the same time, I found myself unable to cut my hair or trim my nails, small acts of rebellion against the gender norms that felt so oppressive.


I also found myself struggling with a new and confusing desire: the desire to spend time with men in a way that wasn't just about being one of the guys. I didn't understand what it meant, and I was terrified to explore it further.


The question of my discomfort in women's clothing lingered. "Could I be a woman if I didn't enjoy wearing women's clothes and wasn't attracted to men?" The concept of being a lesbian didn't even cross my mind back then. I couldn't fathom how someone with a penis could be a lesbian. It took me a long time to find the answer, mostly because being discharged under "Don't Ask, Don't Tell" pushed me so deep into the closet that I crossed well beyond the borders of Narnia. I found myself lost in a world of self-denial. I buried my feelings and tried to conform to society's expectations of who I should be.


Looking back, it's clear that I was experiencing gender dysphoria – the distress a person feels due to a mismatch between their gender identity and their sex assigned at birth. It's a feeling that many transgender individuals, those whose gender identity differs from the sex they were assigned at birth, grapple with throughout their lives.


Jessica Purdy wearing a black trench, black and white flannel. Her hair is swept back and has a weak mustache.  She looks a bit like Sam Smith in their music video, Stay With Me.
Jessica Purdy on a subway in Seoul, Korea.

But at the time, I had no framework for understanding what I was going through. I had no language to describe the disconnect I felt between my body and my sense of self, no way to make sense of the yearning I felt to be seen and recognized as a woman.


And so I pushed those feelings down, deeper and deeper, until they were buried so far beneath the surface that I could almost pretend they didn't exist. I threw myself into my work, into my relationships with women, into anything that would distract me from the gnawing sense that something was fundamentally wrong.


But the truth had a way of bubbling up to the surface, no matter how hard I tried to suppress it. And as the years went by, I found myself increasingly unable to ignore the voice inside me that whispered, "You are not who you pretend to be. You are not the man everyone thinks you are."


It would be a long and difficult journey to finally confront that truth, to find the courage to embrace my identity as a transgender woman. But even in those early years, when I was still so deeply in denial, I knew that something was different about me, that I was searching for a way to be my authentic self, even if I didn't yet know what that self might be.


A World Destroying Divorce: Reconsidering Closeted Life

For years, I had built a life based on the idea of what it meant to be a man, a husband, a provider. I had carefully constructed an identity around the expectations of masculinity, molding myself into the shape of what I thought a young man should be. I worked hard, I provided for my family, I played the role of the strong, stoic, unflappable male.


But when my wife left me for one of the most masculine men I knew at the time, my entire world came crashing down. The life I had so carefully constructed and maintained, the identity I had crafted for myself, suddenly felt like a hollow shell, a flimsy façade that had been ripped away to reveal the truth beneath.


Jessica Purdy looking like an unhappy man.  She's has a full goatee and is wearing a ballcap, flannel over shirt, a henley tee, and a choker necklace. On the wall behind her are prints of the four seasons and just in front of her left shoulder is a bamboo plant.
Jessica Purdy just before the economic crash.

I was forced to confront the ways in which masculinity and my body didn't align, the ways in which the expectations of manhood felt like a prison, a cage that I had willingly locked myself into. I realized that I had never truly felt at home in my own skin, that the body I inhabited didn't feel like it belonged to me.


"Why don't I like wearing women's clothes?" I asked myself again, as I had so many times before. But this time, the answer came to me with startling clarity: I didn't like wearing women's clothes because it made it impossible for me to ignore the fact that my body didn't fit. It didn't feel or look the way it should.


Suddenly, a thought struck me: "I could transition." I had heard about treatments and surgeries that could help align a person's body with their gender identity. If my body looked and felt like home, I realized, I would love to wear women's clothes. I would feel comfortable and confident in my own skin, free from the constant sense of discomfort and unease that had plagued me for so long.


I also realized that I didn't actually like most men's fashion. While it could look good on some men, I felt uncomfortable wearing it, as if I were pretending or acting, playing a role that didn't fit me. The realization was both terrifying and exhilarating.


But wait, I thought, I wasn't gay. I didn't want to have sex with men. I’m still couldn’t fathom the idea that a person with a penis could be a lesbian. And yet, as I examined my own desires more closely, I realized that I only really had sex because it was what was expected of me, what my partners desired. My own needs and wants had always taken a backseat to the expectations of masculinity.  “Oh, shit.  I’m asexual!”


As I grappled with these realizations, the economy was cratering around me. I felt trapped, both by my financial circumstances and by my own fear of embracing my true self. How could I possibly transition, I wondered, when I was losing everything? How could I face the social stigma, the rejection, the upheaval that would come with living authentically as a woman?


But even as I tried to push these thoughts aside, to bury them beneath the rubble of my shattered life, I knew that I couldn't ignore them forever. The truth had been revealed to me, and there was no going back to the way things were before. I had to find a way to move forward, to build a new life that was true to who I really was, even if I didn't yet know exactly what that would look like.


Betrayed By My Body: Needing to Live as Myself

In 2014 I was showing the first signs of a movement disorder. My arms and torso began to move uncontrollably, shaking and bobbling as if they had a mind of their own. I staggered and stalled, my movements becoming increasingly erratic and unpredictable. My hands trembled, making even the simplest tasks a challenge. , I felt like I was losing control of my own body.


When I finally received my diagnosis, it was almost a relief. At least now I had a name for what was happening to me, even if the doctors couldn't say for sure whether it was Parkinson's, MS, Lewy body dementia, or something else entirely. But with the diagnosis came a crushing realization: I had lost control of my own body, and there was no going back to the way things were before.


The news hit me like a ton of bricks. I felt like I had been handed a death sentence, like my life was suddenly measured in months or years rather than decades. I thought about all the things I had never done, all the experiences I had never had, all the parts of myself I had never fully explored or expressed.


"Fuck," I thought. "I have never really lived the life I was meant to live."


But even in that moment of despair, I felt a flicker of determination, a spark of hope that refused to be extinguished. I made a promise to myself, right then and there: as soon as I could get my body under control, as soon as I had a handle on my symptoms and my prognosis, I would become the person I was meant to be. I would embrace my true self, my authentic identity, and live the life I had always dreamed of living.


I knew it wouldn't be easy. I knew there would be obstacles and challenges, moments of doubt and fear and uncertainty. But I also knew that I had no choice. I had been given a wake-up call, a stark reminder of my own mortality, and I couldn't waste another moment living a lie.


And so, with a newfound sense of urgency and purpose, I threw myself into my treatment plan. I worked with my doctors to find the right therapies, the right strategies for managing my symptoms. I focused on my physical health, determined to get my body back under control so that I could focus on my mental and emotional well-being.

At the same time, I began to explore my gender identity more deeply, to confront the feelings and desires I had buried for so long. I read books and articles, I joined support groups and online communities, I talked to other transgender people about their own journeys and experiences.


Slowly but surely, I began to piece together a new understanding of myself, a new vision for my life. I realized that I didn't just want to survive my diagnosis – I wanted to thrive in spite of it. I wanted to live my life to the fullest, to embrace my true self and all the joy and fulfillment that came with it.


It hasn’t always been easy. There have been ups and downs, triumphs, and setbacks. But to know me now is to know that I have found true joy, peace, and purpose. I am who I was always meant to be.  I am a woman.  I am wholly and unabashedly me.



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1 Comment


franrodriguez45
Mar 16

Jessica, my heart is overflowing with so much joy & pride for you, woman!! I’ll never forget the first time we met during the YWCA’s virtual panel discussion. It feels like a lifetime ago and I’m grateful to call you a friend.


Thanks for sharing your story of courage with the world💐


With gratitude,

Fran Rodriguez

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