May 20, 2013 12:00 PM

It’s Saturday at the Boylan home in Belgrade Lakes, Maine, and Jennifer, 54, is tugging a chestnut-colored riding boot over a stubborn pant leg. “These are my Fluevogs,” she says, proudly indicating her designer boots. As for the unsleek trousers, “I guess these are my mom jeans.” Her wife, Deirdre, 53, looks over and laughs. “Jenny-pie,” she says, “I thought every pair were mom jeans.”

In the twelve years since she transitioned from male to female, Jenny, an English professor at Colby College, may not have become a fashionista. But by every important measure, her choice to step away from her identity as James to become the person she’d always felt she was has proved a resounding success. She’s infinitely happier “waking up and not thinking, ugh, I have to pull off this boy thing again,” she says. Her 2002 memoir about her transition, She’s Not There, was a bestseller. Most impressively, her marriage to Deirdre, a social worker with whom she has two sons (Zach, 19, a freshman at Vassar, and Sean, 17, a high school junior) not only survived but thrived, as she details in her new memoir, Stuck in the Middle with You. “Jenny’s mom’s motto was ‘Love will prevail,’ ” says Deirdre. “That’s been true for us.”

Though they weren’t always sure it would be. After their wedding in 1988, “the feelings of wanting to be female went away” for a time, says Jenny, who hoped “falling in love would cure me.” But in 1998, after dabbling with cross-dressing and repressing her true self for decades, she finally told Deirdre she was “having gender issues,” she says. By 2002 she’d undergone hormone therapy and gender-reassignment surgery. Reveling in her new body and changing sexuality, she experimented with pink nails and a black bikini, began “seeing men in a different way,” and started to feel like she was “living the life I always wanted.” Yet as Jenny flourished, Deirdre struggled. Though neither seriously considered leaving, “I wasn’t sure I wanted to be married to a woman,” Deirdre says. “I was angry and afraid.”

Then in 2002 Deirdre’s sister died of cancer, a loss that brought clarity. “There’s a difference between losing someone forever and having someone change genders,” she says. “I needed Jenny.” Slowly they found their way back to each other, reclaiming “intimacy,” says Jenny, returning to kissing and sleeping in the same bed. Ultimately Deirdre realized “Jenny was the same person, just more herself.”

Although Jenny’s biggest worry had been hurting her sons, they took the changes in stride. “It seemed as if I was doing something that would jeopardize their safety,” she says. Fortunately their small Maine town proved supportive, and “they were never bullied,” she says. “One mother turned her back on them, but that was kind of it.” Zach and Sean—who call their former dad “Maddy”—now say their upbringing made them better men. “Being brought up in an unusual family made me more tolerant,” says Sean. Adds Zach: “They showed us nothing but love. What else matters?”

Indeed, on a recent Saturday afternoon, the Boylans are the picture of familial bliss: two guys zoning out over video games, one parent making muffins, the other hatching a dinner plan. Next month Jenny and Deirdre will celebrate their 25th wedding anniversary. “We’re lucky,” says Deirdre. Adds Jenny: “We’re aware of the gifts we have. And that’s a great blessing.”

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