“I hate being on the phone,” says Sarah, who handles computer networks for a company on Long Island. “I hate leaving voicemail. I hate meeting new people. I hate my voice. It sounds so male-ish.”

So every Saturday morning, Sarah (not her real name), who has been living as a woman for the past nine years, shows up at Garbo’s door for a 45-minute lesson on how to make her speech more feminine.

Sarah spends most of her waking hours carefully watching how she speaks. She feels that if she slips up, the $100,000 she has spent to shed every trace of masculinity—at a doctor’s clinic in Scottsdale, Arizona, to reshape her genitalia; on estrogen shots to adjust her hormones; on electrolysis to get rid of the hair on her face—will count for nothing.

* * *

Today, a thin line of black eyeliner marks Sarah’s eyes, setting off the tint of blue eye shadow on her eyelids. A pink pendant dangles from a gold chain over her bright blue turtleneck, which is tucked into her slim-fitting dark denim jeans, topped off with a black leather jacket.

Sarah has come a long way from her earliest days living as a woman, when she says she smudged more mascara over her face than on her eyelashes, and had to spend two hours every morning staring at a pool of colors in her wardrobe before she could put together an outfit.

She has come even farther from the days she spent casting envious glances at girls in her school in Nassau County, Long Island.

“By second grade, I knew I was in the wrong body,” Sarah says.

“I tried to tell my parents in the fourth grade, then seventh grade and 10th grade,” she says, but “every time I would change the subject, thinking things would go badly.”

Sarah held on to her secret as she finished school, rode on the dot-com boom in the late 1990s to make money as cofounder of a tech firm in Philadelphia, and lost everything at the turn of the century.

All the while, “I was going crazy,” she says. “I had to tell my parents”—both for her own sanity and so that she could finally begin the transition process.

On a frigid February morning in 2000, as Sarah, then 25, sat beside her mother in her parents’ Volvo, the car jerked to a halt at a busy intersection on Old Country Road.

“My mom lost control of the car when I told her I wanted to transition,” Sarah says. “We almost had an accident.”

Sarah’s mother went into therapy two days later; her father joined a support group for families of transgender people.

“You’re going to be a freak,” Sarah recalls her father’s words. He suggested that Sarah see a psychiatrist to change her mind.

She waited six years for her parents to come around. “I wanted their acceptance” before having surgery, she says. Eventually, they warmed to the idea, and Sarah scheduled the procedure for the spring of 2007.

Even before she underwent her gender-reassignment surgery, she knew she had to sound like a woman. So in 2006, at the recommendation of a friend from her support group for transgender people, she turned to Garbo.