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A family doctor’s journey from man to woman

Dr. Roy Berkowitz-Shelton’s life seemed to be the picture of stability: loving wife and family, successful practice. But to find his true self, he needed to risk all of that.

Part one in a two-part series. From 8/12/2007

ON MAY 22, 2006, MIKE FOSTER WAS SITTING on the padded exam table in his doctor's office, undergoing his annual physical. It was a familiar place. For 14 years, he'd been coming to see the same doctor in the same Somerville office a few blocks from the same two-family home that had been in Foster's family for four generations. And it was a comfortable place. Despite having to wear a hospital johnny that stretched to cover his 6-foot- 7 frame, Foster felt at ease, because of the doctor sitting across from him. Roy Berkowitz-Shelton, a soft-spoken, bald, middle-aged family physician a foot shorter than Foster, always managed to convey competence and caring at the same time.

Foster, who managed truck sales for a local Chevy dealership, looked younger than his 52 years, with his full head of light-brown hair just beginning to admit some gray. But his body, which had served him well during his days playing basketball for Somerville High School, was definitely showing its miles. Bad knees, bone spurs in his heels, a blood clot in his leg, and a back so bad it required triple fusion spinal surgery. Throughout it all, Dr. Berkowitz-Shelton had been his source of stability, coordinating care with other specialists.

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There was something else that made his doctor special. During visits, he always reserved ample time to talk about Foster's personal life, about his children, his marriage, his work, his level of happiness. They found that despite their different backgrounds, they had a lot in common: Both were 52-year-old, hard-working men devoted to their wives of 25 years and their college-age kids.

"He was a friend, a confidant," Foster says. "I felt I could talk to him about anything."

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But as this exam was winding down, it was the doctor who chose to do the confiding. Peering over the glasses resting on the tip of his nose, he told Foster there was going to be a major change in the practice in about a month. A letter would soon be going out to all his patients, but he wanted to give Foster advance notice.

From the seriousness in his doctor's voice, Foster sensed he was about to tell him he was moving to California or retiring early or leaving medicine. He had built up so much trust in the guy that he dreaded the prospect of losing him.

"I'm going to be transitioning to live my life as a woman," the doctor said.

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Foster was floored. He stared at Berkowitz- Shelton, and for the first time noticed that he was not just cleanshaven but now appeared to be devoid of facial hair. This was no joke. Foster struggled to come up with an appropriate response. But his first thought was how some of the tougher townies he grew up with in Somerville might have responded had they been sitting on the exam table, wearing the johnny. Would they have just punched him in the nose? Foster put that thought aside and said, "That's interesting. How are your peers taking the news?"

Berkowitz-Shelton replied that they were generally very supportive.

"So, do you think this is going to affect your practice?"

Berkowitz-Shelton said he hoped it wouldn't, but he knew he was going to lose some patients.

Foster regained his footing and cracked, "Well, you're in the Bermuda Triangle here in Davis Square between Brookline, Cambridge, and Somerville. Your business may actually go up!"

Berkowitz-Shelton chuckled. "I hope so."

Foster wished his doctor well and reminded him he would be back in a month for a follow-up.

But his mind was racing as he left the office. During his lifetime, he had seen a Davis Square once dominated by Italian and Irish families like his become transformed into one of the most diverse swaths of pavement in Greater Boston. No spot in the square captured this cross section as effortlessly as the pale-green waiting room in Berkowitz-Shelton's Davis Square Family Practice. Conservative and liberal, rosary-bead-clutching and atheist, rich and poor, infant and octogenarian, black and white, gay and straight, townie and foreigner, veal-loving and vegan - they were all here. The other physician in the office would often marvel at the single day when she had seen patients from every inhabited continent on the globe.

Foster was a traditional guy, but he had come to view the changes around him with a sort of amused acceptance - and a sense of distance, as though he were watching it all unfold on film. But this change he'd just been asked to accept was hitting much closer to home. My trusted doctor is a transsexual? To him, even the term was off-putting, conjuring HBO shows airing at 2 in the morning and tabloid headlines screaming about a convicted murderer trying to get the state to pay for sex-change surgery. That stuff had nothing to do with him. So he'd never had to think seriously about this issue of people who felt they were born in the wrong bodies.

Now, with just one sentence from his doctor, all his mental escape routes were closed off , all the distance was gone.

"So there I am with a professional, outstanding family physician that I had known for many years, who's completely changing his life," Foster would say later. "It was right up there with the day John F. Kennedy got shot when I was in the third grade, and all the other things in your life that you'll never forget."

Not long ago, the usual route of someone transitioning to a different sex was to move to a distant city and start a new life, alone. Berkowitz-Shelton told Foster he had contemplated doing exactly that, but he couldn't bear to leave the family he had at home and the family of patients he'd forged in his nearly 18 years of practicing in Davis Square.

But by choosing to stay put for his life-changing journey, the devoted doctor was thrusting a decision onto his family, his staff , and the nearly 4,000 patients in his practice. Would they choose to come along?

THERE'S THIS OLD CHILDREN'S BOOK CALLED The Story of Ferdinand. It's about a young bull in Spain who doesn't fit in with the other bulls. They spend all their time butting each other's heads, hoping one day to be picked for the bullfights in Madrid. But Ferdinand prefers to sit under a cork tree and smell the flowers. His mother tries nudging him to join in with the others, but Ferdinand demurs. Through a mix-up, he ends up in the bullfighting ring. But after refusing to fight the matador, he gets to go home to his cork tree.

It's a sweet story, and when he was a kid, it was Roy Shelton's favorite.

The boy grew up in a voluble Jewish family living in an apartment building in Flushing, Queens. He was short and not athletic, so he didn't like going outside to play ball with the neighborhood kids. His mother would nag him, "Why aren't you out there playing?" Roy loved rainy days, because he didn't have to apologize for wanting to stay inside.

His only sibling was a sister three years younger. When he was around 5, he loved pushing her doll carriage around the apartment. At the same age, he went into his mother's closet and tried on her shoes. They felt good. But these were the only outward signs of the somewhat odd feelings he had inside.

In school, he displayed no feminine behavior, though he sometimes imagined being one of his female teachers, whether she was young or a 65-year-old battle-ax. At The Bronx High School of Science, he was painfully shy around girls, spending most of his time with his bookish male friends. But he wasn't attracted to boys. If he saw a beautiful woman on the subway, he might fantasize being her, rather than being with her. But he figured this was just part of the confusion of the teenage years.

He once appeared at the cosmetics counter at a department store and nervously explained that he needed to buy lip gloss for his sister. But mostly he managed to keep things inside.

In 1979, while he was going to Georgetown University School of Medicine, Roy and his housemates decided to have a party. He went to the local market for provisions. The reserved 25-year-old woman behind the checkout counter seemed really nice. Her name was Alison, and she had an earthy quality to her. "We're having this party," Roy told her. "Do you wanna come?"

She didn't show. Three months later, he invited her to another party, and once again she was a no-show. But this time she called to apologize, said she had gotten sick. They started talking and fell into an easy rhythm. They went to the movies. "I felt immediately very, very comfortable with her," Roy would say later, "and she with me."

In 1981, Roy Shelton and Alison Berkowitz were married.

If he still harbored doubts about his identity, if he still thought longingly about the New Jersey rest stop on the drive between Georgetown and his parents' house where a vending machine offered embarrassment-free purchases of lipstick, the relationship with Alison provided the perfect opportunity to build a fulfilling life. He loved her, felt a deep connection with her. He would find satisfaction by being a good husband and a good doctor and find structure by following the rules of his Conservative Jewish faith.

The Army had paid Roy's medical school bills, and after his residency, he became an active-duty Army doctor at a hospital in Germany. By then, he had added Alison's maiden name to his own. One day, he mustered the courage to tell his new wife about his fantasy of dressing as a woman. She seemed uncomfortable. But as he remembers it, she tried to be understanding and even went shopping with him to pick out women's shoes and stockings.

Yet there's a difference between being open-minded and being interested. When he experimented with those stockings and shoes in their most private moments, his wife's discomfort was clear. So he pulled back, purging his cache of women's things.

Before long, there were new places to find fulfillment. In 1985, they had their first child, a son. Two years later, they returned to the States. In 1988, they had a daughter, and later that year, they moved to Newton and he opened his office in Davis Square.

He was building his life around faith, family, and his family practice. Eventually, Alison joined the practice as office manager.

"He had everything," says his sister, Amy Lembo. "A great family life, a practice that was phenomenal."

But inside there was confusion, a certain emptiness, and a lot of hiding.

In the summer of 2000, he asked his wife if she would be OK if he shaved off the beard he had worn for years. Even after she agreed, he waited nearly two years before taking the razor to his face. "I just really wanted to please her, and I know she liked it," he would explain later. "But I think I also was afraid that it was going to be the start of this journey, and I didn't really know where it would end."

THEY HAD JUST FINISHED shopping at a Whole Foods in Newton. It was January 2004, and Roy was 50. He and his wife had put the bags in the trunk and were getting into their seats when he blurted it out. "Alison, I feel I'm a woman," he said. He was crying, and soon so was his wife.

He obviously hadn't planned things very well. Who delivers earth-shattering news in a supermarket parking lot? But things had been building for so long. Ever since Germany, he had kept his confusing feelings to himself, indulging in cross-dressing only when he was alone. He would buy stockings and wigs and then purge them. He could never purge the feelings.

Given his close bonds with his patients, over the years many had opened up to him about their own internal struggles. Some came out as gay after decades of denial. He wondered to himself: They're being true to themselves. Am I?

He needed to tell Alison, that much he was sure of. But he was just as sure that he wanted to save his marriage. He loved his wife, his kids, his life.

Eventually, his wife told him he had to figure out who he was before they could determine what it meant for the marriage. He went seeking information and was stunned at how little he knew. He learned that "transgender" is an umbrella term applying to people whose feelings don't match the sex the obstetrician cheerily announced in the delivery room. But it's a big umbrella. It includes cross-dressers, who derive pleasure or comfort from wearing clothing opposite their assigned gender, and transsexuals, who feel their gender identity is opposite what they were assigned at birth and choose to live full time in their new gender, with or without surgery. He learned that gender identity - who you feel you are - is completely different from sexual orientation - who you're attracted to. He knew that many religious conservatives view transsexuality as an abomination against God, but he learned researchers were still trying to figure out what causes it.

Roy knew his desire to be a woman was potent, but he wasn't sure where he fit on the spectrum. If he could be content being a woman only in the confines of the bedroom, that might help keep his marriage intact.

In April 2004, he met with Brookline gender therapist Ellen Rottersmann and laid out his twin priorities: sorting out his gender issues while saving his marriage. Early on, she invited him to "present" as a woman for their weekly sessions, if that made him feel more comfortable. He accepted, bringing women's clothing with him and changing in the office before and after the appointment. He called his female self Jessica, so that's the name Rottersmann used.

That summer, he read She's Not There, a memoir by Jennifer Finney Boylan, a transsexual and Colby College professor. The book led to an epiphany. At one point, Roy put it down and said to himself, "Oh, I guess I'm a transsexual."

He began taking female hormones. Near the end of the summer, he shared his secret one evening with Carol Dansky, who had been his physician's assistant for a decade. When Alison found out, she was upset. She made it clear she wanted him to keep his soul-searching private, to protect their kids. But in other ways, he says, she was incredibly supportive.

For his 51st birthday on October 24, 2004, Alison gave him a red journal embossed with gold. On the first page, she inscribed a passage from James Baldwin. "No one can possibly know what is about to happen: It is happening, each time, for the first time, for the only time."

A few weeks later, Roy wrote this entry: "My conviction, my inner conviction, of being a woman is very strong. . . . I'm hoping not to be abandoned by my family when I come out to them. . . . I want to be looked at as a loving, caring, normal human being - which is after all how I view myself. I've just made a big mistake in covering up who I really am all these years."

The next month saw the biggest leap. Alison agreed to accompany Roy as Jessica for a weekend in Newport, Rhode Island. For him, it was liberating, even if Jessica's appearance drew stares. Recounting the trip in his journal, Roy wrote: "I felt totally comfortable with my female visage even though I didn't pass. Perhaps there was some emptiness because Alison felt so disassociated from the experience. She was very pleasant but there was an uneasiness about her."

Back at home, Roy took steps to increase his chances of passing in the future. He began meeting with a voice coach who helped him adjust his male-typical, "throat-focused" voice to find a more feminine sound. He also began laser hair-removal treatment on his face. Finally, he changed the name of his female self to Deborah, which was more common than Jessica in nurseries around the time of his birth.

In February 2005, Roy went to lunch with Bari Brodsky, the other physician in the practice. They had previously discussed her moving from employee to partner after two years on the job, and she was about to hit that milestone. They shared an approach to medicine, but in other ways were different species. Brodsky kept all her spice jars at home alphabetized. Roy's office was so covered with piles of files that it was hard to find his desk. Brodsky was sure they would be discussing partnership, so she prepared a detailed list of questions. When Roy shared the real reason he had asked her to lunch, she was impressed with his courage but confused. "This has nothing to do with all these financial questions I have on my list."

In a way, it did. Roy explained that if he transitioned to live full time as a woman, he had no idea how many of his patients would stick around.

He had been making friends through an Internet site for the transgender community, and in April 2005 ventured to New York to meet them, as Deborah. A few days after returning, Deborah sat in Rottersmann's office, finishing up the weekly gender therapy session. As was the routine, Rottersmann was about to leave so her client could change out of Deborah's clothes and back into Roy's. But this time, Deborah broke down. "I don't want to take off these clothes. I feel so good as Deborah."

From then on, there would be plenty more tears and doubts, but no turning back.

On September 27 came this journal entry about feeling like Deborah at work, even while dressed as Roy. "I'm not angry at Roy. He was an okay guy. . . . He tried to cover up Deborah because she just didn't fit into any construct that we usually know. I'm so glad that I finally found a way to free up Deborah."

In December, after their daughter had submitted her college applications and had a chance to exhale, Roy and Alison sat her and their son down in their Newton home and broke the news. At the beginning of 2006, they flew to Florida to tell Roy's parents. "First of all," Roy said, facing his parents as they sat in their den, "I want you to know that I'm not dying. I don't have cancer. But what I'm going to tell you is going to seem horrendous." Not long after that, he traveled to New Jersey to tell his sister and her husband, as they sat in their finished basement.

There was shock all around. But some of the reactions surprised him. He had expected his daughter to be more accepting than his son, but it was she who reacted with hurt and anger, while his son seemed more open. His mother had an easier time with it than his father.

His sister, Amy Lembo, said he had her support and love, but she admitted that she just didn't get it. Roy left to meet some friends and returned later that afternoon, having gotten his nails done. It was an image Lembo would never forget. "Red nail polish. Oh, my God. It turned my stomach."

Afterward, she told her husband, "You think you know somebody all of your life, and then 50 years later, this."

AFTER MAKING THE DECISION TO LIVE FULL time as a woman, Roy made the related decision that he wanted to look more like one. There are two primary surgery options for male-to-female transsexuals: facial feminization surgery, to change the appearance of the face in subtle but important ways; and sexual reassignment surgery, or SRS, to change the genitals. People can do one, both, or neither, although surgeons usually require that patients live full time in their new gender for a year prior to SRS.

Roy scheduled facial surgery for June 29, 2006. Then he carefully mapped out how he would tell his patients, staff, and medical colleagues. He wrote a detailed letter, set up a website (davissquareinfo.com), and scheduled a series of question-and-answer sessions at his office.

But planning can only get you so far. He had no idea how many patients would return when he did, in late July, after recuperating.

In May, his synagogue bulletin carried this note: "Mazel Tov to Alison and Roy Berkowitz- Shelton on their 25th wedding anniversary." The couple let the date, June 7, pass without celebration. Roy felt exhilaration mixed with some apprehension about what lay ahead in his new life. But he felt anguish at the pain he knew he was putting his wife through.

His sister called and told him, "You should really rethink this." He was upset. This wasn't some whim. He knew what he was risking. Many transsexuals report having been suicidal before transitioning, but that wasn't the case with him. He had a choice; he could have gone on living as Roy. But he feared how empty he would feel at the end of his life if he did. "I don't care what I have to do," he told his sister. "I just know I want to die as a woman."

What about his wonderful marriage, his sister asked. Was he willing to sacrifice that? Roy said he was confident Alison would stand by him. "Are you for real?" his sister replied.

Something triggered a memory of Ferdinand, the children's story about the bull who didn't fit in. He ordered a copy. When he read it, with the distance of nearly half a century, it produced fresh tears. He finally understood why he had loved the story so much as a child.

In the beginning of June, he mailed out his letter to patients. "After almost 18 years of practicing medicine in Davis Square," it began, "I am looking forward to many more years as your family physician. There will be only one major change that will occur in July - I will begin practicing medicine as a woman, Deborah Bershel, MD." The new last name was a combination of his old hyphenated name, Berkowitz-Shelton.

On a Wednesday afternoon in the middle of June, Roy was walking in Davis Square when he bumped into one of his patients.

"Hi!" Roy said warmly. He was wearing a brown blazer, a dark tie, and charcoal slacks. On his shoulder he carried a hanger that held a patterned silk skirt and a teal short-sleeve top.

The patient, an older guy, looked down at the ground and mumbled, "I got your letter." He studied the ground some more. "I guess I'll get used to it."

Other reaction coming in was more supportive. Two patients sent flowers. Others stopped by the office to offer encouragement. The night before, when he held his first of three Q&A sessions, about 60 people showed up, many lavishing praise. His sister's oldest daughter wrote a heartfelt note apologizing for her initial discomfort, promising support. Margaret Connolly, a 75- year-old patient who'd been coming to the practice for 14 years, wrote him a note comparing his decision to her own nearly a decade earlier, when she left religious life after having spent more than 30 years as a nun. "There will be some difficult times ahead," she wrote. But in her own case, she realized, "if I did not act I would not have been true to myself and would lose some life within."

Yet he knew this early reaction wasn't necessarily representative of his larger patient pool. It seemed likely that the patients who were most upset would skip the Q&A sessions and register their response with nothing more than a written request to have their records transferred to another practice.

Around 5 o'clock on that Wednesday in June, he reminded the staff to meet in the waiting room. Roy had promised a preview of Deborah, to make the first day back after facial surgery easier on everyone.

Ten minutes later, Deborah emerged, wearing the outfit Roy had been carrying on a hanger. A black wig covered his bald scalp and scraggly graying hair.

"Well," Deborah said tentatively, in a feminine voice. "How do I look?"

There was a burst of chatter.

"Whoever said I look good gets a 10-cent raise," Deborah said, to laughs.

Paula Mahoney, a 41-year-old no-nonsense Somerville woman who worked the front desk alongside her daughter, said the real changes were deeper. "Before, when we had a stressful day, you'd get cranky. But that first day after you told us your news, it was wicked, wicked busy, and you were popping around all smiley."

Her daughter, Carolyn, piped up, "You're still you."

THE FOLLOWING TUESDAY, JUST BEFORE 6:30 p.m., Walter Lowry Jr. walked into the waiting room. "Mr. Tambourine Man" was playing softly on the office sound system. A Boston native of Italian and Irish blood, Lowry was a 50-year-old former Marine who worked in airline operations at Logan Airport. He wore his dark-brown hair slicked back and his short-sleeve shirt open to midway down his chest.

In his 15 years with the practice, Lowry had faced some serious medical problems. He felt that Dr. Berkowitz-Shelton had been there for him all along.

When he received the letter, he could hardly believe it. He decided to attend a Q&A session, not to bathe his doctor in encouragement, but to gauge where the doctor's head was. "I wanted to know this wasn't some fluke," Lowry explained later. "I wanted to make sure I wasn't putting myself in harm's way because of someone else's midlife crisis."

Shortly after Lowry and a half-dozen other patients showed up for this second Q&A, Roy passed around a photo of Deborah to help prepare them.

When the photo landed in his lap, Lowry took one look at it and allowed a nervous chuckle. He tipped it upside down for comic effect. But then he studied the photo, and his face grew serious. It dawned on him then just how tormented his doctor must have been to be making such a radical move, to be putting his family through all of this. A wave of compassion washed over Lowry. This was more than just a picture of someone in a wig and a dress. This was real.

"I am so comfortable as Deborah," Roy told the patients. "In a year, I bet no one will remember me as a man."

But as Alison's inscription in the journal said, "No one can possibly know what is about to happen." Would most patients find a way to stay, or drift away? Would the marriage survive, or become a part of Roy's past, to be packed up with all his blazers and ties? Would life as Deborah feel fulfilling enough to compensate for the anguish it took to release her?

All Lowry could control were his own actions. Going forward, he could make no promises that he wouldn't flub up on names and pronouns, or experience some anxiety before his next physical. But as he left the waiting room, he could promise this much: He would be back.

Part 2: A Year as Deborah

Neil Swidey is a staff writer for the Globe Magazine. E-mail him at swidey@globe.com.

Scott LaPierre and Ann Silvio of the Globe Staff contributed to this story.

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