June 30, 2025,

My wife sits down on the couch as I crack open a can of hard cider and set it on the coffee table in front of her. She cues up the latest episode of Taskmaster and I pop open a can of beer for myself. This is a standard ritual except for what comes later. I’m going to tell her that I may be, I am, or think I am transgender. My plan is half-baked at best but keeping this from her is eating me up inside. I can’t seem to find a good way to approach the topic, so I down my first beer and open a second. Perhaps after the show (and after another beer) a better opportunity will emerge to open this proverbial can of worms. I am procrastinating, just like the night before… and the night before that.

Let’s Back Up a Little

In the spring of this year something began to unravel. It started when I decided to confront my growing interest with a certain sub genre of pornography. Confront is definitely an overstatement because I really only sought answers that wouldn’t require serious introspection or corrective action. I thought a cursory search would provide some reassurance that it is totally normal to enjoy this sort of smut and there was no reason for concern; my fixation would probably fade as soon as something else piqued my interest or life simply got too busy. Initially, I found a couple of takes on this that told me exactly what I wanted to hear: pornography is performative, participants play roles and present fantasy. Enjoyment from sexual fantasy doesn’t necessarily indicate a desire of the viewer to engage in such activities in real life.

What a relief. One more corroborating source would surely put my concerns to rest, so I continued. I came across an article whose title summed up my query perfectly, “It’s Just a Fetish, Right?” by Amanda Roman. I was not prepared for what I was about to read.

To say the article struck a nerve would be an understatement; it was more like a lightning bolt to the prefrontal cortex. It described a pattern of behavior that I had engaged in, in various forms, since puberty. Here’s the part where the lightning hit:

“Turning my feelings into sexual urges made them easy to purge. Whenever the distracting thoughts arose, I could simply read a few stories about men transforming into women, get aroused, have a brief moment of release, and then move on with my life. And for 20 years, that’s exactly what I did.”

My early experience lacked the internet stories (as there was no internet) but I found inspiration where I could. In my pre-teens I colored my fingernails with craft paint so I could touch myself with girl hands, in later teens I would put on lipstick in private and squint at my reflection — until I saw the girl in the mirror, in my twenties (and throughout the next 20 plus years) began putting on my live-in girlfriend’s clothes when she was not home and more recently consuming unhealthy amounts of sissification porn. All of them involved envisioning myself in a more feminine form and getting off on it. These were a few examples of the behaviors that I compartmentalized, never recognizing them as a repeating pattern of the same underlying coping mechanism.

Subsequently, I did the most stereotypical thing a so-called trans egg could do; I typed into the search bar, “How do I know if I’m trans?” Actually, I typed numerous versions of this question into search engines, podcast apps, and YouTube.

During the course of this inquiry, I discovered that so many of the shameful secrets, confusing thoughts, nagging questions, and awkward situations in my past were not merely a series of isolated incidents and they were not unique to me. Over and over again, I found uncanny similarities reflected back to me in the narratives of transgender women. I came to realize those previously unexplained (and oddly unforgettable) incidents might be linked by a common thread called gender dysphoria (or gender incongruence or gender dissonance or some similar sounding term that I had only just discovered).

Here’s an analogy I don’t hate too much: after decades of looking at the stars and only seeing random points of light, I have learned to identify the ones that form ‘The Big Dipper’. Once you see it (at least if you live above 35 degrees latitude) you will always see it. It is relatively easy to identify and provides a reference point to help locate other stars, asterisms and constellations. You may not see it on an overcast night or you may simply choose not to look at it but the knowledge of its presence is undeniable. It has always been there. More than that, the two stars (Merak and Dubhe) that form the outer of edge of its bowl form a line that points directly to Polaris - aka the North Star. A nearly fixed point in the night sky, it has been used as a celestial compass for centuries. It provides direction in the darkest of nights.

The stars pointed me towards two immediate conclusions:

1. It’s time to seek professional advice.
2. I need to tell my wife.

After 22 years of marriage, almost 30 years together as a couple, Lynn knows me better than anyone. I trust her more than any therapist. I have also convinced myself that an old snapshot will help clarify my dilemma.

A Brief Search For Clues

“The photograph must be around here somewhere,” I tell myself. It was taken sometime around late 1995 or perhaps sometime later in ‘96. It was not a dare, a lost bet, or a Halloween costume, and it was done at my request. It is a photograph of me in full face makeup (That’s totally normal, right?). My wife, then girlfriend, had some basic stuff. Her makeup routine consisted mainly of translucent powder and cherry chapstick but she did have some foundation, lipstick, and eye shadow. She went to work with a limited palette and a less-than-ideal canvas. For some reason, even though I didn’t generally like being photographed, we captured the moment for posterity. To the best of my recollection, the results were underwhelming. Nonetheless, I felt revisiting it now could provide a clue that would either affirm suspicions of trans identity or confirm this foolish endeavor as another manifestation of a midlife crisis. To be honest, I was rooting for the latter if for no other reason than to avoid an awkward conversation (and I will do anything to avoid an awkward conversation). Leafing through photos brought me back in time through Christmas cards, wedding photos, deceased pets, and old friends whose whereabouts are unknown. They are not organized; we have photos in a loose stack on the dresser, in keepsake boxes, and tucked in the back of desk drawers. Envelopes of 35mm prints jump back to a third-year college dorm with a repurposed toilet containing a tropical plant and Jane’s Addiction posters on the wall or forward to a niece’s Monster High-themed birthday party. Finally, I open a drawer containing a couple of envelopes of photos and some mementos from the mid to late 1990s: a Blockbuster Video membership card, the cigarette lighter from my old ‘86 Pontiac 6000, and the name tag from the second-rate department store I worked at from late ‘95 to ‘97.

That was a difficult time for me personally. My parents and I were no longer on speaking terms after Lynn and I moved in together; they called it “the situation” (not a reference to Jersey Shore). Despite earning a Bachelor’s degree, the best job I could find was at Ames Department Store, making only slightly above minimum wage. Benefits were nonexistent but at least they didn’t require short hair; there was no way I was chopping off my long blonde locks for a crappy retail job. It was only 10 miles away from the university I graduated from and Lynn was enrolled in but it felt a world away. I was not aware of how different the social environment was outside of college life. In this new context, my long hair and clean-shaven face, combined with the ubiquitous flannel shirts, blue jeans, and boots, conveyed farm girl more than it did grunge dude. I heard “Excuse me, ma’am” and “Thank you, miss” more often than “Are you working hard or hardly working?” Sure, getting misgendered was disconcerting at first but I understood that their mistakes were honest ones. Who could blame them? I wasn’t exactly projecting peak masculine energy and these mistakes mostly came from older folks who were exceptionally kind and polite. I stopped correcting them. It was just easier that way. People seemed nicer when they thought I was female or maybe it just felt nicer for me; correcting people only made the exchange more uncomfortable. As long as I pretended not to notice, no one felt weird or apologized— no harm, no foul. If they did notice, I was quick to reply with a “no problem, happens all the time.”

I flipped through every photo and still did not find the one I was looking for. If I still had it, this is where it would be. I made one more pass through pictures of old cars, dead pets, and the few that I failed to avoid getting caught in. I paused because even though the sought-after photo was not here, the answer was. I forgot how long and full my hair was, how thin I was, how straight and white my teeth were, and that I actually had a reason to smile. A voice whispered in the back of my head, “I would have called her ma’am, too.”

Back to June 30th…

It’s fast approaching midnight. I’ve just cracked into my third can of beer. Lynn is still on her second cider. I try to summon a matter-of-fact tone, “You know how they say gender identity is on a spectrum?” She nods while taking a sip, my voice wavers, “I don’t think I’m exactly on the… uh, cisgender end of that spectrum.” With an amused laugh, she asks, “You think you’re trans?” She is expecting a wacky story, perhaps even an emphatic denial to her question. I stammer “Y-Yeah… I think so.” Tears stream down my face as the amused expression drains from hers. She is not prepared to hear this or the explanation that follows.

I started writing this article in the first week of July as a means to help work through some shit. Since then, I have continuously rewritten, edited, and entirely discarded sections of this piece. Among the stuff that got cut out or I failed to find a way to weave in was: an anecdote about taking far too much time stocking the women’s hair color aisle, a dream about the coolest chick I ever met who happened be just like me only the girl version, how much I loved when the girls down the hall would braid my hair, and my overuse of the “lesbian trapped in a man’s body” joke.

I appreciate everyone here who has been so supportive and thoughtful in our conversations. If you are one of those people, you probably know that I am still on the fence and the fence is getting shaky. Thanks for reading.

Coming Out To My Wife As Trans was originally published in Lost In Transitions on Medium, where people are continuing the conversation by highlighting and responding to this story.

It was a cool spring morning when I left the house to see my friend, Eric. Our backyards were nearly adjacent, making it a quick walk from my family’s home to his. Upon arrival, Mrs. C called my mom to let her know I was there and promptly directed us to the basement as she had important things to do.

Confinement to the basement was not punishment in any way. We had a ping pong table, numerous games, toys, and a ton of sports equipment. Everything a couple of 8-year-old boys could want. We fumbled around with the hockey and football gear, trying on various combinations of oversized helmets, shoulder pads, gloves, and cleats. Nothing fit but we were having fun nonetheless. We punched the boxing heavy bag with everything we had — it hardly budged. Then something else caught my eye, far away from the sports gear, two pairs of stiletto-heeled leather boots.

Eric protested as I reached for the boots, “Those are my mom’s. I don’t think we’re supposed to touch those.” I ignored his plea, slipped on the black boots, and slid the long zipper up. “Fits pretty good, you should try those ones” pointing at the other pair. He relented and pulled on the brown pair. We tried to be quiet as we giggled to ourselves, first nearly falling over with each step but slowly becoming steadier, eventually becoming adept at maintaining our balance on the smooth concrete floor. After a while, I think we just forgot that we were wearing them and resumed other activities. We didn’t hear Mrs. C come down the steps. She started to say, “Hey guys, I’ve got a snack for…” her words trailed off as her jaw dropped a little. She looked at us, down at the boots as we then looked down at the boots as if we too were surprised to see them and back at her with wide eyes. We got busted!

I expected a stern tongue lashing but instead, Mrs. C adeptly changed gears from a ‘wtf’ look to a smile and a little laugh. “Let’s take off the boots and come upstairs, you two have been so good playing quietly down here that I prepared some milk and cookies for you.” She had us at milk and cookies. We were careful to put the boots back where we found them and clean up the rest of the mess we made. As we sat down eating our cookies Mr. C entered the house, he gave Mrs. C a hug and kiss, Eric a hug. Mrs. C pulled him aside and spoke in a hushed tone as she pointed to us, to the basement door and then to her feet. I thought we were in big trouble now. Instead, Mr. C laughed and nodded as the two hatched a plan. There was more whispered conversation between them and then Eric’s mom smiled and said, “How would you boys like some REAL boxing lessons?” We looked at each other and lit up like it was Christmas morning. In a flash, Mr. C had changed out of his suit and tie and into some proper sweatpants and an old t-shirt. He was in full boxing coach mode and we were like a couple of little Rocky Balboas. He outfitted us each with a pair of practice gloves to use on the bags. He gave us tips on form, showed us how to punch the speed bag at different rhythms and how to hit the heavy bag without hurting our wrists. To top it all off, Mr. C taped up our hands and properly fitted the big red boxing gloves. Those things were the real deal, some serious Wide World of Sports stuff. (Before you think it — No, we did not fight each other for the amusement of the adults.) We went out to the backyard where Eric’s dad staged some boxing poses while his mom snapped photos to capture the moment. Boys being boys…

The fact that this day ended in smiles and fake punches stands in sharp contrast to subsequent ones when I failed at adhering to expected gender norms. Like the time I couldn’t stop crying in the 3rd grade. Classmates called me a crybaby and a sissy and the teacher sent me out to the hallway “until I could act like a boy”. Or the time in 6th grade when I accidentally wore my sister’s shirt to school and a group of boys recoiled in horror like they’d seen a monster.

On a spring day all the way back in 1980, I learned a little something about pugilism and power, balance and grace. My divergence from cultural norms was not beaten down by shame or ridicule. I was punching above my weight…in high heels and dungarees. Years later, I could still work the speed bag with some degree of rhythm and precision. I found I could still work the heels too.

Boxing Lessons For Sissy was originally published in Lost In Transitions on Medium, where people are continuing the conversation by highlighting and responding to this story.