Freeing Up Deborah

When Dr. Roy Berkowitz-Shelton decided to live as a woman, he gambled that his marriage and medical practice would survive the change. In the conclusion of our two-part series, Dr. Deborah Bershel emerges and confronts her new reality.

Part 1: A Family Doctor's Journey From Man to Woman  |  PART 2
Dr. Deborah Bershel and her patients reflect on the practice after her sex change.
By Neil Swidey
August 19, 2007

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At age 52, Deborah Bershel made her first trip to the mall. It lasted nine hours. It was July 2006, and there was barely a rack of clothes in the Burlington Mall that she didn't comb through. The next day she headed to the Natick Mall and logged another five hours shopping. She was making up for lost time. In each store, her approach was usually the same. She'd march up to a salesclerk and explain, "I'm a transsexual, so I'm new to this." Then she'd ask her particular question, whether it be which cut of jeans would cover the top of her panties or which type of fabrics wouldn't cling to her arms. "I have questions that no 50-year-old woman should have," she said.

It was behavior so uninhibited it would have been unthinkable in her previous life. As a husband, father, and family physician, Roy Berkowitz-Shelton was many things – compassionate, dutiful, funny. But no one would have called him uninhibited. For years, he had struggled to understand the feelings inside him that made him question whether he really was a man and made him attracted to the clothes that went along with being a woman. Yet that struggle had been almost entirely internal.

A month before the maiden visit to the mall, he had gone public. He told his patients and colleagues what his family had known for some months: that he was a woman and would soon transition to live life that way. He stressed his hope that even after Roy Berkowitz-Shelton, MD, was gone, replaced by Deborah Bershel, MD, his patients, colleagues, and family would naturally become hers. Whether that would actually happen was anybody's guess.

On June 29, 2006, after more than a year and a half of taking female hormones, Roy Berkowitz-Shelton lay on an operating table while a Boston University School of Medicine plastic surgeon smoothed down his forehead, made his nose smaller and more upturned, lifted his brow and upper lip, softened his jaw line, brought his hairline forward, and performed what's called a "tracheal shave," removing the lump on the throat that is so identified with being male that it's named after the original one. Seven and a half hours later, bruised and drained, Deborah Bershel emerged.

She quickly found that more than her appearance had changed. As a man, Roy cared little about clothes, and a trip to the mall held all the appeal of a dental cleaning. As a woman, Deborah was surprised to learn that she genuinely enjoyed shopping. Of course, not everything had changed. She was still compassionate and well informed. And frugal. She blanched at the price tags on the designer outfits she saw at Macy's and ended up making many of her purchases at TJ Maxx. For one brown top, she splurged and plunked down $50, but that was an aberration. More common was her pattern of acquisitions at Payless: nine pairs of shoes for a total of $85.

In the weeks after surgery, everything was building toward her July 24 return to Davis Square Family Practice, the Somerville medical office she had run as Roy for nearly 18 years. Alison, who had married Roy a quarter-century earlier and served as the practice's office manager, had helped care for Deborah in their Newton home during the week immediately following her surgery. But the future of their marriage, like so much else, was uncertain. However supportive she may have been, Alison had made it clear there was a reason she had married a man. Deborah had agreed to move back into the Brighton apartment where Roy had lived during the months leading up to the transition and stay there until their daughter left for college.

The Saturday before her return to the office, Deborah spent hours organizing all her new clothing, by color. It was a move that Roy, who had been infamous for his clutter, would have resisted. It felt good to be packing up all of Roy's clothes, a ho-hum collection of off-the-rack suits, button-down shirts, and khakis. It was only when she came to a favorite colorful tie that she lingered. Roy had taken pride in his many vibrant ties, which were especially popular with his pediatric patients. Holding the tie, she felt a small pang of sadness, the same pang she'd felt at the supermarket when she spotted a young father roughhousing with his son on his shoulders. That scene, that tie, were part of the past now. There was a whole new life to be lived.

After all the buildup, the actual first day back in the office was a bit anticlimactic. No one on the staff said much about how she looked. Deborah couldn't tell if that was because they thought she didn't look good, or because they felt uncomfortable being positive about the new her with her pained wife sitting so close by, or because they were weary of all the distraction the transition had caused and wanted simply to get back to work.

When she performed an annual physical on a male patient, his only complaint was that he had overheard the front-office staff referring to Deborah as "him." Another patient reminded Deborah that the front window of the practice still carried Roy's name. Still, through the day, many patients did what the office staff had not: complimented Deborah on how good she looked. Even if some aspects of her presentation were still very much a work in progress – her gait remained more Roy's than Deborah's, and her voice was not where she wanted it to be – the overall change made her look a decade younger. Patients took note. One woman in her late 50s purred, "You look gorgeous!" before turning to someone else on the staff and saying, "I want that surgery – I want to look like her!"

The praise moved Deborah, because it affirmed what she felt inside. "When I look in the mirror, I'm happy with what I see. As Roy, I was only sad. No one ever said I looked good. Here I am, a half-baked woman, and everyone compliments me. What are they seeing? They're seeing my essence. I feel like a whole person now."

Deborah stood on the bimah, or elevated platform, in her Lexington synagogue during Yom Kippur services in October. It was the rabbi's custom to kiss each woman on the cheek before she stepped down from the bimah and to shake each man's hand. When it was Deborah's turn, the rabbi kissed her cheek. Deborah was delighted. Roy had made Judaism central to his life. Deborah wanted the ability to do the same. Her Conservative Jewish faith offered no easy answers on transsexuality. But with that one kiss, Deborah felt her rabbi "was giving permission to the entire congregation to treat me the way I'd like to be treated."

In November, Deborah's parents met her for the first time.

Not long after arriving at their home in Florida, Deborah went for a stroll along a boardwalk with her mother. Instinctively, she took her mother's hand. "It was the first time I can remember that happening," she would say later. "I felt closer to her than I think I had in my life." They went shopping. Her mother came into the dressing room with her, chiding her, "You're taking your top off like a man!" They laughed. That night, when her mother was lying down in bed, Deborah went into her room and said, "I just want to tell you what a great time I had today."

As Deborah recalls it, her mother replied, "I had a wonderful time with my daughter today, too."

Her father was also trying to be supportive. He said he felt horrible to learn his only son had grown up with so much pain. But he was upset that so much had been hidden for so long, to the point where his grandchildren had been made victims of these circumstances. He and his wife had always told their children they could confide anything in them. Why hadn't Roy told them growing up? Deborah tried to explain that for most of the time as Roy, he didn't know exactly what was going on.

Back home, the news was bleak. After their daughter left for college, Deborah had given up the Brighton apartment and moved back in with Alison. The understanding was they would try living together for one year. But after a few months, everything changed. Their daughter returned home for other reasons. And Alison asked Deborah to move out. Deborah began hunting for a new place, telling people, "Alison is not interested in a marriage to a woman."

A few months back, when Roy's sister had warned him that going through with the transition would mean sacrificing a long, loving marriage, Roy had dismissed that prediction. From the moment he first began meeting with a gender therapist more than two years earlier, he had been unambiguous about his twin priorities: sorting out his gender and maintaining his marriage. As clarity arrived with the first priority, he genuinely believed it would help in achieving the second. He was feeling unburdened by finally being true to himself and hoped this new enlightenment would help Deborah begin a new, deeper, more honest life together with her family. But it would be hard for them not to view the decision to transition, on some level, as a rejection of the life they had already built together.

Deborah was upset that, after 25 years of marriage, her wife felt it had to end. But she knew her own struggles had thrust the decision on Alison. "She's innocent in all this," Deborah said. "She really is."

They fanned across the conference area of the Burlington Marriott and filed into its windowless rooms with the familiar blue and green floral rugs and retractable tan walls. It could have been a conference of Rotarians. In fact, appearing right below their event on the hotel's list of functions for January 19, 2007, was the weekly Burlington Rotary Club meeting. No doubt there were Rotarians in this mix of 600 souls, as well as lawyers and programmers and mechanics. But most of them weren't wearing their usual attire. It was "First Event," the 27th annual conference for the transgender community run by a support group called the Tiffany Club of New England. For many, the weekend offered a rare opportunity to be out and about as their true selves. There was someone with a protruding stomach and a 5 o'clock shadow who wore a loud dress and a cowboy hat over long, curly hair. There was a lithe, younger woman with runway-model looks, a transsexual whose transformation was so convincing she could go "stealth." And there were examples of everyone in between.

The conference spoke to both the diversity within this little-understood segment of society and the power of capitalism to understand any market where there's money to be made. There were booths peddling services to add hair, remove hair, and offer peace of mind when driving with somebody else's hair (Gender ID Cards: "Don't drive dressed without one!"). There were workshops given by credentialed surgeons that sometimes felt uncomfortably like sales calls, since transitioning patients typically pay tens of thousands of dollars for procedures that insurers refuse to cover.

Onto this scene arrived Deborah, wearing a teal top, jeans, and a leather jacket. Many, if not most, of the other attendees – including the married father of two who organized the conference – would be returning at the end of the weekend to life in the gender they were assigned at birth. This year, Deborah would still be herself come Monday.

She knew she was fortunate. She had the money to afford a full transition – she'd already spent $24,000 on her facial feminization surgery, roughly the same amount on therapists and cosmetic treatments, and she was seriously contemplating another $20,000 or so for sexual reassignment surgery. And she was self-employed, so she didn't have to worry about being summarily fired for coming out, a fate that has befallen other transsexuals, who generally operate with little of the employment protection offered to minorities, people with disabilities, or gays and lesbians.

Many of the therapists, doctors, and consultants leading workshops were the same people who had helped guide Deborah through her transition. During a presentation by Boston University School of Medicine surgeon Jeffrey Spiegel, Deborah looked up at the screen to see a photo of someone who had just had undergone facial feminization surgery. "Oh, that's me," she said. The 37-year-old Spiegel offered fascinating thoughts on how males evolved to have narrow eyes under heavy brows, to protect them from enemy punches, while women evolved to have large, open eye areas to advertise their femaleness.

During another workshop, the daughter of a transsexual explained how she had worked through her discomfort to draw close to her father as a woman. Deborah could only hope that her own daughter, who wasn't speaking to her, would someday be able to say the same thing. She was grateful that at least her 21-year-old son seemed more accepting.

The next morning, Deborah sat in a darkened conference room listening to a presentation on sexual reassignment surgery by Pierre Brassard of Montreal, who wore a smart suit and spoke with a thick French accent. While some of the other surgeons gave softened descriptions of the procedure – one filled her PowerPoint presentation with slides of her children – Brassard pulled no punches. His sometimes gory slides took the audience, step by step, through his procedure for inverting the penile skin to create a vagina, including the removal of the testicles.

As some audience members shifted uncomfortably in their seats, Brassard apologized, "I hope this isn't too graphic."

Deborah cracked, "As long as I'm asleep during the surgery!"

Several audience members emerged from the room with all the color drained from their faces, but not Deborah. As a physician who had endured graphic lectures during medical school, she respected Brassard's candor. She no longer had any doubts about whether she would have reassignment surgery or who would do it. Wearing a wide smile, she said, "I need to have this done now!"

It wouldn't be that easy.

Andrew was feeling anxious. The 46-year-old, who works in real estate and asked that his last name not be used, had been coming to the medical practice for nearly a decade. Having chosen Dr. Berkowitz-Shelton partly because he felt more comfortable with male doctors, Andrew wasn't sure he'd be able to handle the new arrangement. Now, on February 27, 2007, he would find out. As he sat in the exam room, waiting for Deborah to arrive, Andrew wondered to himself, "Is it going to have a freaky Provincetown vibe?"

When it was over, he was relieved to learn that it didn't. "It felt like your middle-aged aunt coming in to do your physical," he said.

Seven months after Deborah had returned to the office as a woman, some patients were still experiencing the change for the first time. Others were surprising themselves at how much more normal things seemed to get with each visit.

The range of patient reaction on this one February day alone was telling.

While Andrew underwent his physical, Neil Callendar stood with his 3-year-old daughter in a nearby exam room. When he had first received the doctor's letter announcing the transition, he figured the easiest route would be to transfer his two young daughters to another practice. "But I thought that would be cowardly," said Callendar, a 41-year-old who teaches African-American literature at a community college. "There was no reason to do it except irrational fear." He and his wife struggled to prepare their 5-year-old daughter for her first visit with Deborah, but the girl took it in stride. "Oh, he was a boy, and now he's a girl," she said, before moving on to what was really worrying her. "Am I going to have to get shots?"

In yet another room, the parent-child fears were reversed. Lilly Ricciardi, a 35-year-old Revere woman, said that when her mother told her about their family doctor's plans, her first question was "What's Daddy going to do?" Now, sitting in the office for her own visit, she was still marveling at how her dad – an old-fashioned, "off-the-boat-from-Italy" guy – had responded. "After he went to see her," Ricciardi explained, "he said, ‘He looked good.' I never thought my dad would come back, but he didn't want to go somewhere else."

The premium patients place on having a trusted doctor, and not wanting to have to wander into the medical wilderness to try to find a new one, helped many get over their initial discomfort. They decided to give Deborah a chance, even if they knew they might stumble on pronouns along the way.

"A good doctor is a good doctor," said Yanick David, a 65-year-old longtime patient originally from France. "I accept him, but I would not wish to be his wife. Can you imagine?" Still, she said she couldn't fathom the reactions of others. Once, when she was at Somerville Hospital and identified her primary-care doctor, she said the staff members behind the counter cracked jokes. "I get so angry," David said. "How low-class."

When Roy first began mapping out the transition, he had no idea if his practice could survive. As late as June 2006, after receiving a round of supportive comments, he figured he would still lose about 10 percent of his patients. But, now, as Deborah ventured into a closet off the waiting room where the "dead charts" of former patients were stored, she could take comfort in knowing that only about 70 patients – around 2 percent of the total pool – had left the practice in response to her transition. Many of those were children whose parents had made the decision for them. Some patients who liked the practice but didn't think they'd be comfortable being treated by Deborah began seeing the other physician or the physician's assistant on staff. But some others who stayed with Deborah reported finding the doctor to be even more effective, if only because she seemed more comfortable in her own skin. The transition also attracted some new patients, such as Kendrah Raye Whyte, a 64-year-old transsexual who had showed up for a checkup on this same February afternoon. The dead-chart closet held the files of almost none of the patients Deborah had originally feared would bolt the practice, such as the 79-year-old Greek immigrant who, instead of leaving, soon resumed his habit of sharing mild locker-room jokes with his trusted doctor.

But there were a few surprise departures. One folder contained a typed letter from a longtime patient who had come to view the doctor as a confidant. It read: "After long consideration I have decided to seek my medical attention elsewhere. I must commend you and your staff for several years of exceptional care and counsel. Best wishes to you on your undertakings in your personal and professional life."

It was signed by Mike Foster, the 6-foot-7 truck sales manager with whom Roy had previewed his transition plans. Foster said later that he had struggled with his decision for half a year. "I just realized that I was going to have a lot of trouble taking him seriously. I guess I refuse to accept that he was a woman."

In March, Bari Brodsky, the other physician in the office, told Deborah she was leaving. It had nothing to do with Deborah becoming a woman, or at least not directly. Brodsky, who'd been with the practice for about four years, had voiced her enthusiastic support for the transition. But because it had put off earlier plans for her to progress from employee to partner in the practice and boost her income, she began to explore advancement elsewhere.

As it turned out, the year had been a difficult one financially for the practice, and Deborah wasn't able to hand out raises. That wasn't because of patient defections, but rather because of unrelated reductions in insurance reimbursements. Had she focused more on improving billing practices, Deborah might have been able to offset some of those losses. But she had always paid more attention to treating patients than increasing revenue.

When Brodsky was offered the chance to run her own shop as medical director of a health center in Cambridge, she took it. Deborah was happy for her. But she was also concerned that many of Brodsky's patients might follow her out the door, bringing a new round of uncertainty to the practice. And she worried that the move would force a delay in her plans to undergo sexual reassignment surgery, since the recuperation would require that she be out of the office for up to a month.

On the second Monday in April, Deborah sat down with Carol Dansky, her physician's assistant of 13 years, to discuss how they would go forward following Brodsky's departure. She sensed a certain distance in Dansky, so about 15 minutes into the conversation, she asked her, "You're not thinking of leaving, are you?"

Dansky admitted she was. Dansky had also been extremely supportive of Deborah's transition, so it wasn't that. It was just that she was 61, her income – with no raise and a smaller bonus – was going down rather than up, and she had grown tired of commuting every other weekend to her second home on Cape Cod. She had decided to live on the Cape full time and work there.

The one-two punch of these exits left Deborah feeling dazed. She asked herself, "How many more blows can I take?"

The practice would surely see a financial hit. (It was her family's sole source of income, since Alison had stayed on as office manager.) Deborah's surgery would probably have to be put on hold indefinitely. She explained that, back when she first announced her transition, "I was hoping that by making this huge change in my life, I would give my patients the courage to make changes in their own lives, to leave an unfulfilling job or a bad marriage or just make a major change they had been contemplating for a long time. I was hoping my example would help them get unstuck. I just didn't expect it would be my staff."

As far back as the fall, Alison had made it clear to Deborah that she would not remain in the marriage. She had been as understanding as she could be, but she simply wasn't interested in being married to a woman. As they continued to meet weekly with a couples therapist, Deborah held out hope, improbably so, that her wife would change her mind. By early spring, it was obvious she wouldn't, so Deborah decided to try to move forward.

At one of their therapy sessions, she asked for Alison's permission to date other people. After getting the OK, Deborah decided to post ads on a few dating sites. But what kind of ads? Was she interested in meeting men or other women? Roy had never been attracted to males. But after taking female hormones, he began to feel flashes of attractions to men. Still, he had to wonder: Was that the estrogen talking, or something more deep-seated? There were no clear answers, since gender identity and sexual attraction are completely different forces, and some male-to-female transsexuals find themselves attracted to males, some to females, and some to both. Now, 10 months after transitioning, Deborah found herself attracted to both. After having spent so much of life suppressing uncertain feelings, she decided to keep an open mind.

On April 1, Deborah stopped by her old house in Newton, scooped up her family's cocker spaniel, and headed over to a dog park in the Auburndale section of the city. She had learned about a dog-walk event on the "women seeking women" section of Craigslist. At the park, she met a dark-haired woman in her late 50s named Berni Zisserson, who had showed up with her Yorkie. Afterward, they grabbed coffee and bagels at the nearby Bruegger's and fell into an easy conversation. Deborah felt a strong attraction to Berni, a spunky psychiatric social worker who had been out as a lesbian since she was 25. And the feeling seemed mutual. They exchanged numbers.

Deborah couldn't stop thinking about Berni, but she didn't know how or when she would tell her that she was a transsexual. Tell her too soon, and she may close down before really getting to know Deborah. Wait too long, and she may end up feeling Deborah had misrepresented herself.

Around 9 p.m. on the same day they'd met, Deborah picked up the phone. "I have something to tell you that is unusual," she said, tentatively. "I am a transsexual."

"I knew it!" Berni replied.

Deborah asked what gave it away.

"Watching you eat a bagel," she said. "No woman would ever eat in such a grabby way in front of others like that!"

They talked for more than an hour. "I don't think I slept that night," Deborah said later.

On a Friday evening three months into their relationship, Deborah and Berni went out to dinner in Needham. Nearly two hours into the meal, Deborah peered over her green rectangular glasses and mentioned, almost offhandedly, "Today's my one-year anniversary, by the way, of being Deborah."

"It is?" replied Berni, whose turquoise top matched her long earrings. "We should celebrate."

Deborah explained that some transsexuals make a big deal of the day they first started living full time in their new gender, considering it their new birthday. But Deborah did not attach the same significance to the day. She had experienced some real lows during the first six months after her June 29 facial feminization surgery, none more so than the dissolution of her marriage and the breach in her relationship with her daughter. She wished she could have found a way to be true to herself without bringing her family such pain. But there had also been plenty of highs. She felt liberated from the lies of her old life, felt gratified by all the support she had received from her patients and even her son, felt relieved to know her practice would survive. Then, in the second half of the year, reality set in. Losing two trusted colleagues in the office, facing financial strain, having to put off her plans for sexual reassignment surgery because the office would have to be closed during her absence – all this had taken its psychological toll. Deborah was holding hands with Berni when she said, "Aside from my relationship with you, the last few months have been really stressful."

Yet the fact that she could emerge from this rough stretch with absolutely no regrets about her decision to live as a woman was perhaps the most reaffirming message of all.

In recent weeks, she had hired two friendly, bright nurse practitioners to replace her departing colleagues. Earlier that day, she told Berni, she spoke to the more experienced of the two, to ask if she would be comfortable overseeing the practice for a few weeks if Deborah left for surgery. "No problem," the woman said.

With that, Deborah felt confident enough to reserve a tentative date in the late fall to undergo sexual reassignment surgery. "I feel like it's an important part, for me, of being Deborah."

Yet subtle changes, in some ways, meant more. That very day, she had performed a physical on an 85-year-old patient whom she hadn't seen in a year and a half. Until recently, she felt it necessary to reserve some time during exams to ask patients if they had any concerns about the experience of seeing her as a woman. But during this visit, she felt no need to bring it up, and the patient seemed completely fine with it.

"It's remarkable how ordinary it is for me now," Deborah said.

And that, she said, was worth celebrating.

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