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There are strange but privileged moments in middle age when you can see certain values of your parents’ generation deservedly dying out, your own generation awkwardly snagged between old and new, and the values of the next generation barreling ahead, to hell with the elders. Nowhere does this play out more blatantly, for me, than in gender fluidity.

Case in point: I know a teenager, born male, who recently chose a new gender-neutral name and announced her preferred pronoun was “she.” Virtually all we adults flubbed it for weeks, forgot, used the old name, said “he,” corrected ourselves, got flustered, apologized. But the other teens? They didn’t miss a beat. She was she, and they adjusted with an ease that astonished me, chastened me.

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Yes, I thought: This is what the proud future looks like.

That future, and how we got here, is my subject today. And Jamison Green is my first invaluable guide. I felt less bad about stumbling with my teen friend after reading Green’s memoir/inquiry/analysis, called “Becoming a Visible Man” (Vanderbilt University, 2012, first out in 2004). That’s because Green showed me how green we are on gender identity. We’ve studied plants for a thousand years, he reminds, but human sexuality for barely a century. And the complex variations within gender are incalculable; 1 in 100 bodies differ from standard female or male, 1 in 1,000 babies are born with ambiguous genitalia.

Green also traces the evolution of how, culturally, humans signal gender. If a man donned a powdered wig now, for instance, many might call him effeminate. Three centuries ago, we’d call him a founding father.

Granted, Caitlyn Jenner and the Emmy-winning series “Transparent” have dramatically changed the conversation. But hearing Green speak to a roomful of college kids, in his book, hit me even more. “What’s more valid: your feelings and your certain knowledge of yourself, or your body, the thing that other people see which signals to them what they can expect from you?’’ this trans man asks them. “Imagine what it would feel like to live with that discrepancy.”

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I know the odd privilege of middle age, but Max Wolf Valerio knows the odd privilege of having lived like an “agent provocateur” in a woman’s world and a man’s world. And so to “The Testosterone Files: My Hormonal and Social Transformation from Female to Male” (Seal, 2006). What a raucous and insightful book this is. Valerio notes that there have been transgender people throughout history, but only now, since we’ve discovered the science behind testosterone and estrogen, has a person actually, chemically, been able to swap. “My life is one of the extravagant experiments of the 20th century,” he realizes.

Valerio’s physical changes are fascinating; someone born male has testicles that manufacture testosterone but, to become male, you take calibrated injections of the hormone. And so Valerio’s skin grows rougher; his pores get bigger; deeper creases appear on his knuckles; hair darkens his face; veins show up on his biceps (women have a layer of fat, enabled by estrogen, that cloaks veins on our arms). “I’m becoming my own identical twin brother,” he jokes.

The emotional and behavioral changes are even more remarkable. The first injections mimic the testosterone levels of an adolescent male. Consequently, Valerio’s face breaks out, and his sex drive goes into overdrive. He has much greater energy and gets more impatient. People also listen to him more attentively (see, ladies, we weren’t paranoid), and he has a harder time coming up with the right words, especially when he’s emotional.

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When Jennifer Finney Boylan transitioned in middle age, she felt euphoric, “like somebody who just got out of prison after 40 years for something she didn’t do.” Boylan, who now appears on Jenner’s reality show “I Am Cait,” came out when she was an English professor at Colby College, a married father of two, and best friends with novelist Richard Russo, who writes the book’s afterword. In “She’s Not There: A Life in Two Genders” (Broadway, 2013, first out in 2003), she is warm, wise, and witty; on her way to her corrective surgery, she sings “I’m Gonna Wash That Man Right Out of My Hair” and sardonically minimizes her change as switching “from regular to Diet Coke.”

But she is serious about how, for decades, she felt an “almost inexpressible degree of private grief.” As a little boy, she poignantly invented “girl planet” where anyone who breathed the air turned into a girl. Boylan’s marriage impressively survives the transition, but there is fallout elsewhere: Her sister severs ties, and Russo is disturbed by his rocky reaction “because it revealed an emotional conservatism in my character I’d have surely denied had anyone accused me of it.” Then there’s the be-careful-what-you-wish-for element; after Boylan begins her estrogen treatments and looks more feminine, a guy menacingly hits on her, and a bartender patronizingly explains baseball’s designated-hitter rule. Welcome to the Sisterhood, Jenny.

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Two more books really broadened my view. Susan Stryker’s “Transgender History” (Seal, 2008) taught me that, in the 1850s, as Americans left tight-knit rural towns for cities with more diverse lifestyles, anti-cross-dressing laws were passed in response. Also, one of the iconic Nazi book-burning photos features the destroyed Berlin library of Magnus Hirschfeld’s Institute for Sexual Science. Hirschfeld was one of the earliest researchers on transgenderism and knew a German endocrinologist named Harry Benjamin, who later collaborated with Alfred Kinsey, and is legendary in the transgender community for his kind humanity and scientific breakthroughs. Christine Jorgensen, once the most famous trans woman in the world, was his patient, and Benjamin’s standards of care for those transitioning are still largely followed today.

In “Trans Gender Warriors: Making History From Joan of Arc to Dennis Rodman” (Beacon, 1996), Leslie Feinberg chronicles “Two-Spirits,” as Native Americans called their transgender tribespeople. Two-Spirits were revered, not maligned; indeed, one commentator noted that at council meetings “nothing can be decided without their advice.” During the Civil War, some 400 soldiers were women posing as men. And Feinberg reminds us that Cupid’s arrows strike across the spectrum; that particular he/she was the child of Hermes and Aphrodite, thus the word hermaphrodite. Feinberg also chronicles how trans men and women have suffered unconscionable violence and discrimination.

I’ll move now to Janet Mock, a trans woman of color who describes her youth in Hawaii — she began her transition at age 15 — in her bestselling “Redefining Realness: My Path to Womanhood, Identity, Love & So Much More” (Atria, 2014). Experiencing poverty, abuse, sexism, racism, and family dysfunction — but also burgeoning empowerment — Mock honors her heroes (Maya Angelou, James Baldwin, Zora Neale Hurston) by showing that she is “full of that oldest human longing — self-revelation,” as Hurston wrote. A former survival sex worker, she’s now a writer and trans advocate based in New York. Her eloquent candor inspires; as she says, cadging the term from trans actress Laverne Cox, she’s not a role model but a “possibility model.”

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Mock is just 31. How were other young trans men and women doing, I wondered? To find out, I turned to “Gender Outlaws: The Next Generation” (Seal, 2010), an anthology edited by Kate Bornstein and S. Bear Bergman. Here, I learned that, within gender, the “taxonomies are endless” and that the T in LGBT can feel marginalized since the LGB community focuses on sexuality instead of gender identity. Likewise, many feminists reject those not pronounced female at birth. But there is rising power here: “I love that transpeople are now at a place, culturally, where we’re not just quietly grateful for being allowed to live,” as Bergman puts it.

By way of penance, I took the book’s “Cisgender Privilege” quiz (cis is the majority, the opposite of trans). It posed 50 questions like this: “Can you expect to find a landlord willing to rent to someone of your gender?’’ “Do other people consider your lifestyle a mental illness?” I have much to learn. But I’m convinced that future generations — future genderations — will transform our world.


Katharine Whittemore is a freelance writer based in Northampton. She can be reached at katharine.whittemore@comcast.net.