Photos by Caroline Sinders

On an unusually sunny and crisp autumn afternoon in November 2010, a family gathered in Saints Peter and Paul Church in Manorville, Long Island. There were about twenty of them, cousins and brothers and uncles and aunts, packed into the quaint white chapel, which began its life as a chicken coop before it was renovated to serve the area’s booming Catholic population in the mid-20th century. The Centrone clan was there to celebrate a baby girl’s christening, but hers was not the only naming the family discussed that day.

Afterward, during lunch at an uncle’s house nearby, the baby’s eighteen-year-old cousin, Vanessa Rose Centrone, a college freshman, asked for her mother’s permission to change her own name.

Cathy Centrone, a 54-year-old elementary school aid, looked at her daughter, and said, “You can change what I gave you, which is your name. But you can’t change how God made you.”

*   *   *

Jacob Centrone, now 20, and more than a year into the physical process of reassigning his gender, scoffs at his former name.

Jacob Centrone
Jacob Centrone


“Vanessa Rose,” he says, shaking his head. “It was the girliest.”  Jacob is five-foot-three and has short-cropped brown hair, a chinstrap beard that frames his angular jaw, and big blue eyes that peek through a pair of black rectangular glasses. Though he can be anxious and fidgety, Jacob’s confidence grows the longer you’re around him.

His bedroom in Middle Village, Queens, where he lives with his mother and stepfather, is an eleven-by ten-foot space with a low bed covered by a plush blue comforter. Above the bed hangs a corkboard splashed with quintessential twenty-year-old sentimentality: photos of Jacob and his friends, old love notes and concert stubs. On top of his bookshelf, like an afterthought, dangles his high school graduation photo. In cursive gold, it reads: “Vanessa 2010.”

In Jacob’s bedroom; Middle Village, Queens
In Jacob’s bedroom; Middle Village, Queens

Jacob pulls a black zippered case off his dresser and sits down on the bed. He takes out a syringe and attaches an eighteen-gauge needle, then picks up a vial of testosterone and disinfects the top with an alcohol swab. He pulls back the syringe’s plunger, then pushes the needle through the lid of the vial. He hikes up his shorts to reveal a pale thigh dotted with coarse hairs. Jacob takes another swab and disinfects a small circle of skin, and then, with his index finger, he draws an X.  To prevent too many scars from developing, Jacob prefers to keep his injections around the same area.

“You see the scars from other ones,” he says of previous injections. “I don’t like to go too far away.”

Jacob hesitates, needle poised over thigh. “The whole thing can be over in five minutes,” he explains. “But it’s usually a fifteen-minute process because half the time I’m freaking out about stabbing myself.”

“Ready? OK. I got this, I got this.”

Jacob administers his own testosterone injection
Jacob administers his own testosterone injection

With a slight shudder, Jacob jams the needle into his skin and forces the plunger down. When he draws out the syringe, it makes a small popping sound. Staring down at the injection, he notices a drop of translucent testosterone alongside the rising red blood. “I’ve never seen it separate like that,” Jacob says, smiling.

*   *   *

Jacob’s parents divorced when he was very young, and his biological father lives in Florida.

“He knows, but I don’t know how he feels about it,” Jacob says, referring to his new gender. “I don’t care how he feels about it, to be honest.”

The youngest of five siblings—two brothers and two sisters—Jacob (then Vanessa) was always a tomboy growing up. Vanessa was interested in playing dress-up — but only to pretend she was a boy.

“In the third grade, I did my communion and I had to wear a dress,” Jacob recalls. “I fought with my mom up until a week before. ‘Fine! I’ll wear the dress,’ I told her. But I didn’t like it.”

Aside from a few casual flings with boys whom she was more interested in being best buds with than actually dating, the young Vanessa was always interested in girls. She began dating girls in junior high, and in high school chopped off all of her hair and stopped shaving her legs, a move that just seemed natural to her.

“I tried making myself as manly as possible without actually becoming a man,” Jacob recalls, “because I didn’t think it was possible yet.”

Jacob has been “Jacob” since Thanksgiving of 2010, just a few days after he first floated the general idea of a name change to his mother. He began by asking his friends to use the new moniker, then insisted his family follow suit. By the time he had it legally changed on April 13, 2011, it already felt normal.

Jacob (then still Vanessa) in middle school, holding a nephew; age 18, a senior at Frank Sinatra School of the Arts in Queens (Photos courtesy Jacob Centrone)
Jacob (then still Vanessa) in middle school, holding a nephew; age 18, a senior at Frank Sinatra School of the Arts in Queens (Photos courtesy Jacob Centrone)

“This is an embarrassing story,” Jacob says, when asked where his adopted name comes from. “So, um, my ex-girlfriend and I—when she got her first dildo, we were thinking of a name and the name Jake popped up. Whenever I wore it I became Jake. I like being called Jake. It was a nice name, and I liked being called this manly name, so I just stuck with it.”

In addition to “becoming Jake” during moments of erotic intimacy with his then-girlfriend, Aimee, Jacob also occasionally took to wearing the purple five-inch dildo outside the bedroom.

“We used to have this strap,” Jacob remembers. “You could use it for fucking, but you could also just use it to wear. I used to literally put it under my boxers and walk around with it on. You could tell there was a bulge, and when my friends noticed, they’d be like ‘Oh my God! Can I touch? Can I feel it?’”

Jacob has since given up “packing,” or wearing an appendage to give the impression of having male genitalia.

“It did get uncomfortable after a while,” he explains.

*   *   *

It all began in a mandatory human sexuality course at LaGuardia Community College, in 2010, when Jacob first discovered the concept of transgender.

“I always just thought I was this butch lesbian,” he says. “I had never heard the term [transgendered] before, but as soon as the professor explained it, everything just clicked. It sounds crazy to say, but she described my whole life.”

“Everything started to make sense—me feeling more comfortable and more manly made sense,” Jacob continues. “But at the same time, it was difficult to understand. I was born female, but it feels all wrong.”

The professor covered transgenderism for a week, and each day Jacob excitedly discussed his new ideas with Aimee. Toward the end of the week, though, she had had enough.

“Her exact words were: ‘You’re still talking about this?’” Jacob recalls. “As a friend, she could support me one hundred percent. But she didn’t know if she could do it as a girlfriend because she was gay, and I wouldn’t be considered a female anymore.”

Though no longer dating, Jacob and Aimee have chosen to remain close. “We try to hang out at least once a week,” Jacob says. “We also speak on the phone almost every day.”

After they broke up, Jacob decided to keep his transgender revelation to himself. He was especially worried about how his family would react.

“I was happy that I was realizing this,” Jacob says of his newfound understanding, “but I was also scared because I’d sit there and wonder, ‘Well, do I want to go through hormone therapy and surgeries? Would I rather just stay as a girl and not do anything? Will people still love me? Will people still care? Will they think I’m weird?’”

Despite these feelings, Jacob chose to press forward, and a few months later, in January 2011, he told his extended family (though not his mother) about his plans. To spare himself the trouble of having to explain his decision to each of his relatives individually, Jacob wrote two mass Facebook messages: one to his aunts, uncles and cousins; and another to his brothers and sisters—the only difference between the two being a string of passionate curse words in the latter.

“I was born female but will start identifying as male,” began the message, in which Jacob laid out the basics of transgenderism and hormone therapy. “It’s not something that is really a choice, more something that I have to do because it feels right. The only choice with this is deciding to do the transition from female to male…This is who I am and who I will always be…I know this isn’t easy for you guys but it’s not for me either.”

Jacobs explains, “I told them that if they couldn’t accept it, that I was sorry, but that I’m going to do it anyway.”

His extended family was shocked, but still, his aunts and uncles responded with a wave of genuine warmth and support. The response from his immediate family, however, was more mixed.

“Penis or no penis, I love you,” Jacob’s brother Eric wrote in a text message to him. Two other siblings’ Facebook statuses revealed that they were “heartbroken.” One of his brothers, Jacob recalls, couldn’t stop crying in bed.

Jacob was confused. “It wasn’t as if I was going to be a different person,” he says now. “If anything, I was just making myself a happier person.”

Jacob’s older sister, Maria, didn’t even acknowledge the Facebook message, and to this day, she still refuses to address its emotional content.

Aside from that brief moment following the christening in Manorville, Jacob never directly told Cathy, his mother, about his transgender identity, nor his plans to begin hormone therapy. He says he wanted to, but just didn’t know how. After reading Jacob’s letter on Facebook, a concerned aunt called the house. Cathy answered, and the aunt divulged everything.

Cathy and Jacob Centrone, Thanksgiving 2010 (Photo courtesy Jacob Centrone)
Cathy and Jacob Centrone, Thanksgiving 2010 (Photo courtesy Jacob Centrone)


Following the news, Cathy was unable to sleep. She had reconciled herself to the point that she was able to grant Jacob his New Year’s wish: that she call him by his new name.

Still, Cathy hesitated on pronouns, and testosterone injections were too much for her to handle. She often wrote letters to Jacob, which she left on the family’s kitchen table. They were usually reminders of chores that needed to be done, and were sometimes addressed to Vanessa, and other times to Jacob. Her last letter begged Jacob not to go through with the transition.

“It’s hard in a way,” Cathy says of the pain she still feels. “But not as hard as the beginning.”

*   *   *

Jacob began taking testosterone in July of 2011. He receives the hormones, which are luckily covered by his insurance, from Callen-Lorde, a community health center in Chelsea that also provided him with months of transgender health education and therapy. For the first six months of testosterone therapy, a nurse at Callen-Lorde assisted Jacob with his injections. The center begins their patients with half a milligram of testosterone to test for any allergies. Then, patients can increase their dosage up to one milligram every two weeks, injected intramuscularly into the thighs or buttocks. Jacob will have to continue this ritual for life.

He has been documenting the changes he is undergoing on his YouTube page, which has drawn more than 10,000 views. Jacob sometimes appears alone, singing seriously, passionately, before the testosterone took effect, and with a sense of embarrassed self-awareness after it began to change him. In other clips, he’s giggling with his friends and their dogs—just another New Yorker, doing what New Yorkers do in their free time. But among other people considering such a life-altering decision themselves, Jacob has become somewhat of a budding Internet celebrity.

The following video, a compilation of Jacob’s own YouTube clips produced by Narratively, illustrates how the testosterone has altered his voice and image over the past seventeen months—as Jacob transitioned farther and farther away from his past as Vanessa.

“I’ve had a lot of people, a lot of guys, come to me and ask me questions,” Jacob says of the influence he’s begun to realize through his openness and bluntness about his often painful journey. “Female to male—people that are considering it, people who have considered it, they ask advice.”

But while Jacob has been largely pleased with the process, it has its downsides, too. The testosterone he is taking to become a man is forcing his body to essentially go through another round of puberty.

“Acne, that’s always bad!” Jacob jokes, referring to the blemishes the testosterone has added to his face. It has also put hair on his body—patches of it, coarse and brown, from his toes to his cheek bones.

“I went to high school for singing and had four years of vocal training, and before that, I used to sing all of the time,” he says. “I can’t sing anymore. I don’t like how I sound most of the time. I can’t hit high notes anymore. I can sing lower, but it just sounds weird to me.”

One of Jacob’s YouTube videos in particular effectively illustrates the changes his voice has undergone. In it, he sings three renditions of Paramore’s “My Love”; one before starting testosterone therapy, one eight weeks in, and another at the sixteen-week mark. Pre-testosterone, Jacob’s voice flutters high with the guitar. Later, it grows deeper, which is to be expected, but more striking is the shift in his singing posture. Jacob bounces his leg while singing throughout, but at the end the gesture seems to take on more force, as if stomping down harder will help his voice soar again.

Jacob’s YouTube channel has served as a mirror for him, a window into his former, and constantly changing, self.  Rather than rushing to forget what he used to look like, he finds it useful to have an archive of how his face and body have changed.

“It makes it easier to remember,” he says. “I know I can look back and say, ‘That was my voice a year ago,’ and ‘Do you see how I didn’t have facial hair then?’”

On his block in Middle Village
On his block in Middle Village


Jacob plans on producing more video clips, including one he intends to title “Trans 101.” In it, he’ll offer advice, to family members like his, who might never in a million years expect to deal with a Vanessa-to-Jacob transition in their midst. Jacob shares some of his favorites, culled from the painful, hilarious, sad and demeaning experiences he’s coped with ever since that day at church in Manorville:

“Do not ask us what our birth names are. It’s rude.”

“If you’re going to mess up and call me ‘she’ and I don’t say anything, just keep going, just keep talking. I know it happens, but when you make a big deal out of it, it’s embarrassing.”

“Don’t ask us how we have sex. Does anyone ask you how you have sex?”

*   *   *

On July 21, 2012, to commemorate his first year on testosterone, Jacob threw a prom-themed party at his house, choosing a Saturday when his parents were out of town. On a block where nearly every home looks identical, the Centrones’ tiki-bar backyard sticks out like an orchid in a cornfield. Out front stands a statue of a Franciscan monk, a gnome holding a sunflower, and a tiny American flag waving in the Middle Village air.  A blanket lined with palm trees hangs in one corner, and a thatched hut enlivens the scene, rendering it very un-Queensy.

Some of Jacob’s guests showed up with prom dates, others came solo, and the host wore his finest pressed dress pants and a white button-down shirt with a black bowtie, because, as he puts it, “I’m all about my bowties.”

“It was a mixture of all of my friends,” Jacob recalls of the guest list. “My cousins were there, my brothers were there. My friend Shane, that I met online, came all the way from Connecticut—he drove three hours just to be there.”

“Mostly gay people, though,” Jacob says with a smile. “I have a lot of gay friends.”

Jacob at the gay pride parade last year (Photo courtesy Jacob Centrone)
Jacob at the gay pride parade last year (Photo courtesy Jacob Centrone)

In the middle of the party, Jacob’s friends all surprised him with a cardboard box labeled “happy 1st birthday.” Inside it was a piggy bank scrawled with big black letters that read: “BOOB JOB.” Thanks to Aimee’s coordination, Jacob had unexpectedly raised close to $1,000, $5,000 shy of the cost of the mastectomy—what he and other trans men refer to us “top surgery”—that will get him that much closer to finally, and physically, becoming Jacob. (He has no desire to undergo genital reassignment surgery.)

For the last year and a half, Jacob has been binding his breasts using tight restricting cloth to conceal them, which can cause discomfort and pain.

“I go halfway through the day and I take them off,” he says. “I always start wearing it, and if it’s late and dark, I just go ‘Whatever!’ and I’ll take it off.”

Jacob was initially saving up to return to college to study English in hopes of one day becoming a book editor. And even though he’s able to return to school next semester, his career dream has been overshadowed by another, more pressing goal—one inspired by an actual dream he had one recent night.

“In my dream I had top surgery,” Jacob remembers, a smile breaking across his face. “When I woke up from the dream…I was miserable all day. It felt so real. I remember being so happy.”

*   *   *

Angela Melamud is a freelance writer born, raised and currently living in Brooklyn, NY. Her work has appeared in The Paris Review, Dossier Journal and The Awl.

Caroline Sinders is a photographer, blogger and interactive telecommunications graduate student. Originally from New Orleans, she currently resides in Brooklyn where she spends all of her time working on multimedia school projects, dreaming in still images and running her blog, Cellar Paper.

Elizabeth Ladzinski is a visual journalist and Southern transplant inspired by the social impact of documentary film and photography.

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