Two Women Share Late-Life Gender Transitions

For Nicole and Kimberly, both now 73, their journeys couldn’t have come soon enough.

Kimberly LaGregor, left, and Nicole Brownstein both married and raised children. But from an early age, each felt she was a woman born in a man’s body. Photo by Ali Kate Cherkis

Nicole Brownstein lives in a 55-and-over housing development in Marlboro. Vinyl siding covers the three-story townhomes; a few rows of brickwork add a rustic panache. It’s the sort of suburban community a newly divorced man might find suitable. When Brownstein first scouted the neighborhood, it seemed like the right environment for a newly divorced man just coming out as a transgender woman.

Brownstein greets me at her front door wearing a black tank top, white capris and a gold necklace with black, teardrop pendants. The necklace seems too ornate for a tank top, but it matches her mood. She is beaming.

It took Brownstein about 65 years to become the woman she always knew she was. Her appearance is striking. She’s 5-foot-9 and stocky. Her shoulder-length blonde hair is noticeably thin. That shouldn’t be surprising. She’s 73. She’s gone through hormone therapy, countless hours of hair removal and five surgeries to reassign her sex, augment her breasts and make her look more feminine. “I consider my journey completed,” she says. “I am living as my true and authentic self.”

Brownstein has invited me for breakfast, along with her friend Kimberly Ann LaGregor, also 73, and also a transgender woman who transitioned late in life. When I arrive, LaGregor is on the couch, relaxing in a floral dress with a gold butterfly necklace and a frosted blonde wig. She frequently runs her hand along the front of her hair to keep the bangs out of her eyes. 

LaGregor and Brownstein met on a cross-dressing website 12 years ago and have been best friends ever since. Their trajectories are similar. Both went to college, started careers, married and raised children.

Both shared something else: From an early age, each felt she was a woman born in a man’s body. 

“I always had this desire,” says Brownstein, “to be inside playing with dolls with the girls, not outside rolling in the mud with the boys.”

Brownstein recalls learning as a child about Christine Jorgenson—a U.S. Army veteran, born George William Jorgenson Jr.—who in 1952 traveled to Denmark for what was then called a sex-change operation. Jorgenson returned to America an instant celebrity.

“I watched the news bulletin,” says Brownstein, “and my initial thought was, oh my God, there are two of us.” To that point, Brownstein had assumed she was the “only child born male who thought herself to be female.”

Growing up in the 1950s, this was not a subject to be discussed with family and friends. Brownstein went into denial. She overcompensated, joining the football and swim teams.

It wasn’t until Brownstein had raised two children—a son and a daughter—and retired from a career as an engineer for IBM that those innermost feelings reemerged. “I realized how miserable I really was,” she says. “When I didn’t have things to occupy the majority of my time, I focused on myself, and I presented more and more as a female.”

Though still married, Brownstein began going out dressed as a woman, always in secret. Once, wearing a skirt and heels in a local supermarket, Brownstein bumped into her wife, who did not recognize her.

After a while, cross-dressing wasn’t enough. Seeking help from a gender therapist, Brownstein came to understand she was transgender; that is, her gender identity did not correspond with her birth sex. 

LaGregor has a different story, with a similar ending. When she was about 10, she began dressing in her sister’s clothes and makeup while her mother was at work. Unsure about her feminine impulses, she started college, joined the Air Force, finished college on the GI Bill, and got a job as an associate engineer designing circuit boards for microchips for RCA. She married and had two sons, now 39 and 33.

For many years, LaGregor says, she ignored her thoughts of being a woman in a man’s body. She sometimes felt depressed. On occasion, she visited female prostitutes in a vain attempt to alleviate her pain and confusion. Then in her 50s, LaGregor began surfing the web for transgender women’s sites, eventually discovering

“I always thought of it as a porno type thing,” LaGregor says, “but these were regular people living out their lives doing what they felt they wanted to do, and I said, ‘Wow, this is me.’”

Like Brownstein, LaGregor went into therapy and at age 70 decided to have what’s now called gender affirmation surgery. This was followed by another surgery six months later to augment her breasts. She’s now living in Monroe with a man named Roger. They plan to marry.

LaGregor and Brownstein met on a cross-dressing website 12 years ago and have been best friends ever since. Photo by Ali Kate Cherkis

Brownstein and LaGregor have each been issued new birth certificates indicating their true genders. Still, I can’t help wondering if any of the old anatomical parts remain. The question, I’m told, is rude—no different than asking a woman what’s down her blouse.

“Suffice it to say that legally, socially, medically, physically, I’m a woman,” Brownstein says. 

Coming to terms with who they are was one thing. Telling their families was another. The first person Brownstein told that she was about to begin a gender transition was her daughter, who asked to see a photo of Brownstein dressed as a woman. “You look good,” her daughter said. She also asked what she could do to help.

Brownstein’s son had a harder time adjusting to the consequential changes ahead—or what those changes would amount to. “I definitely didn’t see this coming, even when he started to grow his hair out,” says Greg Brownstein, a 45-year-old IT architect living in Freehold. “I thought maybe it was a late midlife crisis, not what it ended up being.”

Initially, says Greg, “I took it in stride—or so I thought. About 10 minutes after he told me, I had an overwhelming feeling that I was losing my father, that he was dying, and it came out of nowhere. I began crying pretty hard at the thought, but we discussed it, and I felt better at the reassurance that he would always be my father and still, on the inside, be the person I’ve always known.”

Though Greg has accepted his parent’s new first name and identity, he finds he has to work at getting the pronouns right. Understanding his parent’s feelings can also be a challenge. At first, Greg had trouble preparing himself for the mood swings brought on by the hormones Nicole takes. But, all of this is getting less daunting.

“Once you realize this needs to be done for her to be happy, it becomes easy to do,” Greg says. “The hardest part, for me, is hearing about and discussing her dating men.”

Greg’s email address book still lists Brownstein as “Dad.”

For Brownstein, telling her wife was even more complicated. After several conversations, they decided to divorce, though she says neither of them really wanted to. But Brownstein needed to transition, and her wife did not want to be married to a woman.

“I have often said,” Brownstein relates, “that she and I would still be together and married if it weren’t for some bitch named Nicole.”

LaGregor’s family wasn’t as accepting. Her ex-wife and one son want nothing to do with her. I began to ask if there is a family member I could interview for this article, but LaGregor stopped me before I could finish the question.

Her diamond rings sparkle as she counts off on the fingers of one hand the people left in her life. “I have my sister, my niece and my son,” she says. “And I have Roger now, which is good.” (Her mother died in 2005, 11 years before her surgery.)

* * *

To live a whole life as one gender and late in the game transition to the other, seems highly unusual, but Brownstein says it’s not rare.

“I know many, many women who transitioned later in life,” she says.

Statistics are hard to come by in the trans community. About 0.6 percent of the U.S. population, or about 1.4 million people, identify as transgender or gender nonconforming, according to a 2016 study by the Williams Institute at the UCLA School of Law. A 2019 study in the journal Translational Andrology and Urology indicates that 0.5 percent of those 65 and older identify as transgender or nonbinary, meaning someone whose gender identity is neither male nor female.  

New Jersey’s most famous trans woman is Barbra “Babs” Siperstein, who grew up as Barry Siperstein in Jersey City, raised a family, and ran the family’s well-known paint store before transitioning in her 60s. She became an advocate for transgender individuals. Just days before her death in February, New Jersey enacted a law bearing her name that allows individuals in the state to change their gender identity on their birth certificate without proof of surgery.

There are several explanations for individuals transitioning late in life. “A lot of people wait until they retire to transition to simplify the earthquake that can happen in your life, because they may be rejected by literally every person in their life,” says Leigh Carrico Mann, a speech-language pathologist at Robert Wood Johnson University Hospital who works with transgender clients. “Or they know it will cause stress if they have children or grandchildren.”

Mann says some individuals who would transition if not for concern for their families express their gender in limited ways, like cross-dressing in safe or private places. “They want to shelter their family from everything a transition would mean.”

The majority of people over age 50 who visit gender-identity clinics are trans females, meaning they were assigned a male identity at birth but transitioned into a female identity, according to a 2016 study reported in the Journal of Sexual Medicine. It can take them a decade, on average, to fully transition, possibly because of employment or familial responsibilities. More than a quarter of this older trans population had obtained hormone treatment via the Internet without medical advice.

While there are numerous reasons individuals transition later in life, one stands out almost universally. According to a 2014 study described in the Journal of Gerontological Social Work, many older individuals take the leap because of an acute awareness that they have limited time left to embrace their authentic selves.

While liberating, transitioning later in life can unleash emotional upheaval. 

“For a younger person, it’s not as traumatic, because they really didn’t identify with a specific [birth gender] role their entire life,” says Gloria Bachmann, a professor of obstetrics and gynecology at Rutgers Robert Wood Johnson Medical School. “But,” she continues, “for those transgender individuals who affirm their gender later in life, many say it’s almost like they had a passing of that individual, and the new individual has emerged.”

Bachmann says people as young as age three can can begin to behave in ways not traditionally regarded as part of their birth-gender role. If, after a full screening, everyone—including the medical team and parents or guardians—is clear this is the right decision, hormonal affirmation treatment can commence during puberty.

Not everyone fits that mold. 

“Babs Siperstein made the decision later in life to pursue the gender that she felt was her,” says Bachmann. “Everyone does it at the age that works for them.”

* * *

Most people undergoing gender transition undergo hormonal affirmation treatment; some have what’s termed upper surgery or top surgery. “Bottom surgery, where the genitalia are changed, that’s a very difficult procedure,” says Bachmann. “There’s lots of morbidity associated with it.” She notes that all surgeries are risky, “but the risks are not as great as with bottom surgery.”

Some young people will take hormone-affirmation treatment, but avoid surgery. If taken during puberty, hormones can stop some naturally occurring gender-related changes. Surgical procedures can follow once these individuals have reached the age of consent, explains Bachmann.

Beyond surgery, there are other serious risks, particularly for those transitioning late. In epidemiological studies, trans women (and possibly trans men) appear to have an increased risk for heart attacks and death due to cardiovascular disease, possibly related to hormone therapy. 

Trans women on estrogen also have a significantly increased risk for venous thromboembolism, or blood clots, which often start in the leg but can break off, go to the lung, become a pulmonary embolus and prove fatal.

Researchers say more study is needed on the effects and risks of hormone therapy in older populations and on the safest forms of estrogen therapy. 

“The main issue, from a medical standpoint, with people that transition later in life, let’s say after age 50, is that there are gaps in knowledge regarding potential risks of hormone therapy [on that population],” says Dr. Michael Irwig, an endocrinologist and professor of medicine at the George Washington University School of Medicine and Health Sciences. “We don’t have a lot of scientific data, so we don’t know what the best regimen is, what the best dose is, what the safest regimen is. We don’t know what potential risks could be. When you’re in your 70s, you generally just have a higher risk of things like heart attacks and strokes, and so we don’t really know how hormone therapy could affect that.”

Every medication, he adds, has risks and benefits. For a transgender woman transitioning later in life, the benefits could be an improvement in mental health, including reduced stress, depression and anxiety. 

HIV is another risk among trans women, in large part because of workplace discrimination. With employment opportunities difficult, some—especially younger, lower-income individuals—go into sex work to make a living. 

Mann, of Robert Wood Johnson, teaches individuals of both sexes who have undergone a gender transition new speech and voice patterns that fit their new gender expression. It’s not just about pitch, she says. Women tend to elongate their syllables and speak with more inflections, rising and falling through the sentence. A man’s voice, she says, is flatter and less melodious.  

But those who previously lived as men quickly learn the baggage that comes with communicating as a female. “When older people who were established in their lives transition toward the feminine side,” Mann says, “they do often start to experience discrimination and being talked over, and having to argue their point, when they never experienced that before.”

Some experts say discrimination and prejudice are less a problem for trans men. “Trans men can also pass much more easily,” says Irwig. “Once they masculinize, you often don’t even know that they’re transgender. They just look like a shorter guy who is wearing baggy clothes, whereas for transgender women, they may have more difficulty passing because they may still have an Adam’s apple, they may have a deep voice, and these physical characteristics give it away more easily.”

It can be easier to transition when young. If puberty is blocked in trans girls (assigned male at birth), says Irwig, they won’t develop an Adam’s apple or a deep voice, and it will be easier for them to be seen as female. 

But, warns Irwig, transitioning young brings a host of other issues like stress, difficulties in school and a lack of grounding that may make it hard to deal with the social and emotional issues that arise during transition.

Despite the health risks in transitioning, there’s also danger in not making the change. The global suicide-attempt rate among transgender individuals is 32-50 percent. Forty-one percent of transgender persons in the United States attempt suicide at least once in their lives, according to a 2016 study reported in the Indian Journal of Psychological Medicine. In the general U.S. population, 4.3 percent of adults in 2017 had suicidal thoughts, based on National Institute of Mental Health data.

Researchers attribute the high rates of suicide attempts among transgender individuals to everything from gender-based victimization to discrimination, bullying, violence, and rejection by family, friends and community. Almost 50 percent of those with gender dysphoria (discomfort with their sex assigned at birth) experience thoughts of suicide, according to a 2018 study at Spain’s University of Oviedo.

Both Brownstein and LaGregor say they contemplated suicide before transitioning. Brownstein was emotionally pained by the disconnect between how she looked on the outside and what she felt on the inside.

“It’s difficult to describe,” she says, “but it’s basically not being able to identify with the body you’re occupying. It’s sort of like getting up in the morning, walking in front of a mirror and looking at yourself and saying, ‘What is that thing doing there? That shouldn’t be there.’” 

* * *

Brownstein’s gender therapist once asked her whether, if she could go back to being 20 years old, she would transition at that age. She said she would not, because being a woman now, having sired and raised children, continues to make her life worthwhile. 

Then the therapist asked, “Okay, same question, but if you could go back to when you were 20 years old, without knowing anything about the future,” would she make the change? Brownstein didn’t hesitate: “If I did not know what was in the future, I would’ve gone back to 20 years old and transitioned then, and spent the rest of my life as Nicole.”

Finding happiness late in life seems enough. “The person that I have become in the past five, six years, I am happier and more self-satisfied than I was in the entire 65 years prior to that,” she says.

Brownstein’s advocacy and support work also brings her happiness. She’s served two terms as president of the Pride Center in New Jersey and runs a family-support group at the Proud Family Health Clinic.

Happiness comes at a cost. Operations like LaGregor’s vaginoplasty (construction of a vagina) have a five-figure pricetag. Breast augmentation costs additional thousands. “That’s a lot of money for someone on a minimum-wage job,” says LaGregor.

Brownstein spent more than $30,000 on two surgeries “down below,” plus a facelift, a brow advance, a scalp reduction, cheek implants and cosmetic work on her eyes and nose.

“And then I went in and had a revision,” she says. “That’s because everything didn’t come out the way we foresaw it, on my face.”

Both have paid thousands of dollars for hair removal. Laser treatments and electrolysis can cost $70-$110 a week and can go on for years. But to Brownstein and LaGregor, it’s worth it.

“I wanted to be able to walk down the street with my head held high, looking straight ahead and not looking down, and have people just ignore me,” says Brownstein. She has achieved that.

Still, at least one ingredient is missing. Now that she’s living as a woman, she wants to find a man. She’s met plenty of eligible men, she says. She just hasn’t found Mr. Right.

“I have a very, very simple desire,” Brownstein says. “I want to find a guy who was me before I transitioned.” 

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