Photo of Lorimer Schenher holding his book

Photography by Jennifer Fell / Cover courtesy of Greystone Books

Book excerpt: ‘This One Looks Like a Boy’

An inspiring and honest account of gender-transition in middle age

I’ve often made decisions based on intuition, and those few choices I’ve regretted were the result of ignoring that little voice. I’ve always known our kids to be three good, kind, sensitive, and infinitely loving human beings, qualities I attributed—and still do—almost completely to Jennifer’s love and skill as a mother and her dedication to nurturing their development. I wasn’t around much during my workaholic phase when they were really young. Even so, we forged a connection and as they grew older, it never seemed as though their interest in hanging out with us waned at all. Sure, we reached the point where they stopped holding our hands to cross the street, but I feel so lucky our kids never hit a period where they rolled their eyes at our every word or didn’t want to spend time with us.

As I contemplated physically transitioning, I thought of the damage friends had endured due to their parents’ actions: emotional or literal abandonment, suicide, alcoholism, drug abuse, infidelity, divorce. If I transitioned, would I be setting our children up for the same sorry adulthoods of endless therapy, toxic relationships, and unmet potential? Could I do this to them? Would “this” sentence them to all of that?

If I transitioned, would I be setting our children up for the same sorry adulthoods of endless therapy, toxic relationships, and unmet potential?

I decided to trust our kids. Sick of a lifetime of vacillation, I slowly began to open up to them about my lifelong struggle. They were two young teens and one preteen—it seemed the worst possible time in their short, fragile lives to live through the transition of a parent. That very reality felt like an added safeguard against me actually doing anything, and I opened up the discussion as a small step, rationalizing that it was a compromise instead of completely blowing their lives apart.

Jennifer and I had both enjoyed safe, secure, stable upbringings and we shared many details of our family lives and our own youths with our kids, unvarnished and real. We wanted them to understand the complexity of family. We each had experienced periods of great loneliness as teens and we wanted our kids to know that we were there to support them, no matter what challenges they encountered, especially in adolescence.

The tone of these conversations would feel familiar for any parent of teens or preteens. I explained the difference between sexual orientation and gender identity, relating them to myself and the life I’d lived, to which they each on different occasions responded with some variation or another of “well, duh.” I was able to point to transgender characters recently cast in some of our favorite television shows and presented in young adult novels the kids were reading to help start the conversation.

A young person in our social circle had begun a male-to-female transition in her early teens, which further opened the door to new insights and wholehearted acceptance from my children. Still, I told my stories of struggling with knowing I was “different” with a certain air of detachment, explaining to the kids that transition was something “that some people decide to do to deal with being different.” It wasn’t until one of them very casually asked, “why don’t you transition?” that I began to think they might emerge not only okay, but unburdened — that their lives might remain intact. The realization dawned on me slowly over several months. Our kids are pretty amazing people and they really do love me.

Suddenly, it seemed, I noticed that transgender stories were being reported on in the news and transgender characters were appearing on television dramas like Orange Is the New Black and Transparent, some played by trans actors. Laverne Cox’s portrayal of Sophia Burset in Orange Is the New Black struck me as groundbreaking, well before Cox—a transgender woman herself—was featured on the May 2014 cover of Time magazine heralding the “transgender tipping point.” These new trans characters weren’t shallow and undeveloped; they were regular people who formed part of a larger narrative, a greater story arc that didn’t seek to exploit them as freaks, twisted serial killers, or the butt of jokes, as had been the trend in mass media for so long. Seeing trans people on television or learning more about trans celebrities wasn’t the attraction for me; watching trans stories move from the fringes of society to mainstream visibility was. Seeing trans and gender nonconforming people’s stories daily online and bursting into the collective consciousness on the street and in coffee shop conversation blew open the doors of my closet. I felt safety in those numbers and wondered how much regret I’d feel later in life if I didn’t build up my courage and start to fully live.

Should I? Shouldn’t I? was replaced with How? When? Am I prepared? Can I convince Jennifer and the kids to join me on this journey?

As has always been my way when processing big decisions, I became withdrawn and insular during the year before my fiftieth birthday. When I imagined myself as an elderly person, every picture my mind conjured was of me as an old man, not an old woman. I didn’t make a bucket list for the second half of my life because I knew it would contain only one entry: stop being afraid and live your life. While I had previously pushed my desire to transition down and suppressed it through the coping mechanisms I’d employed throughout my life, many of my methods had ceased to work and I could not stop thinking about transitioning. Should I? Shouldn’t I? was replaced with How? When? Am I prepared? Can I convince Jennifer and the kids to join me on this journey?

These questions kept me up every night, and when I did finally fall asleep, I would awaken with a start—heart pounding—and my racing mind wouldn’t allow me to fall back asleep for hours. One night, as I anxiously paced the halls of our home in the hours just after midnight, I stepped into the boys’ room, breathing in every scent, sight, and sound. I stood there, watching their little chests rise and fall as they slept. Barry moaned loudly a few times, as he often did. Liam uttered a string of gibberish before rolling over. I ached with the familiarity of them. Will I have to throw this all away once I make my decision?

Some weeks, out of pure fatigue, I’d consciously force the idea out of my head, telling myself I was not going to transition, to stop thinking about it and envision a future life as a woman. I could push it aside for a few hours—far less than the day or two I could manage in my younger years—but I couldn’t visualize a female future and the thoughts would eventually burst forth again, rushing in with such force that I couldn’t resist them.

One fearful week, I’d lapsed back into thinking I could avoid transitioning, which made me tense and cranky. Jennifer and I were dressing for the wedding of some friends and, as usual, I agonized over what to wear. Finally, I chose a collared shirt and one of the custom suits I’d had made for the inquiry. When Jennifer saw my choice, she wrinkled up her nose and suggested I wear something else, selecting a black turtleneck. Resigned, I put it on with black pants; the monochromatic chic worked, but still I felt dejected. I had taken to wearing a chest binder—a tight heavy elastic undergarment that completely flattened my chest—but even that failed to make me feel more congruent. As we mingled during the cocktail portion of the reception, a striking, younger straight couple we knew well joined us. As we caught up with them, I stared spellbound at the man’s vintage black suit and coral shirt. Why am I not wearing a suit? That moment was pivotal. The prospect of transition had shifted from an “if ” to a “when”; I could no longer stop it.

The prospect of transition had shifted from an “if ” to a “when”; I could no longer stop it.

It was never about cool suits, or hair, or liking sports and cars. It was never about a fear of ambiguity or a preference for all things “male” over all things “female.” It was never about seeking an escape from the second-class citizenry experienced by women in the world. My experiences moving through the world as female had been resoundingly positive. My deepest sense of self was indisputably male. It wouldn’t be until I felt that first dose of testosterone—with its powerful sense of rightness—course through my body that I would know what had been missing, like a safe finally clicking open after the right combination of numbers was entered.

I longed to adopt more outward symbols of manliness: facial hair, clothing styled for men, my man’s body built by a lifetime of physical activity. For all the variability among every type of man there is, I just knew I was one, that in a binary world, I fit into the male box far more surely than the female one. Neither was lesser or greater than the other.

It just is. I just am. I’m a man.

This essay has been adapted from the book This One Looks Like a Boy: My Gender Journey to Life as a Man by Lorimer Shenher. ©2019. Published by Greystone Books. All rights reserved.