“Transitioning Has Been A Journey And I Wouldn’t Trade It For The World.”

by Pearl Bennett

“Transitioning Has Been A Journey And I Wouldn’t Trade It For The World.”

“What Was It Like? Stories by LGBTQ Elders” is a new program by I’m From Driftwood, in partnership with Comcast, the nation’s largest cable provider, and SAGE, the country’s largest and oldest organization dedicated to improving the lives of LGBTQ older adults. Learn more about the program here.

Pearl Bennett’s 6 Video Stories and transcripts can be seen below.



My name is Pearl, I’m a transgender woman. I didn’t transition until I was 50 years of age. Back in high school as I lived as a boy, a teenage boy. And I had a girlfriend that I took to the debutante’s ball in the 11th grade and the prom in the 12th grade. When we graduated, I got a music scholarship to a junior college and she, she was accepted to go to, she was accepted at Spelman University in Atlanta, Georgia.

She loved me very much. I loved her. I felt that this probably would not work because I had a lot of questions about my sexuality. I was, I had a very strong feeling that I was gay. We didn’t have, use the term “gay” back then. And so I figured while she was away at college, up in Atlanta, and I was in a local junior college, I would, I could explore this whole gay thing.

About a month into the semester, I’m busy doing my work I need to do and I assume she’s up in Atlanta doing the work she has to do and all of a sudden she was back home. And I get a call from her mother saying, “Phyllis has dropped out of school.”

And I said, “Why?”

And she said, “She wants to be with you.”

And I said, “I’ll talk to her.”

And so what I did was, Phyllis and I got together and she was going to go to the junior college with me. I said, “Oh, absolutely not.” I said, “You worked too hard to get into this school,” and I said, “Phyllis, I, I’m, I think I like, you know, I’m not sure of my sexuality.”

I think that’s the way I put it. I didn’t come out and say that I like men. She couldn’t hear it. She couldn’t hear it. She was very upset. And she, I remember a lot of crying and I think she even, she was upset at me and I just felt awful. But I, some part of me felt like in the long run, I’m going to be happy that I told her this. And I am.

I think that being honest was, came out of a sense of not wanting the guilt of her changing her life, having her life going in a whole different course.

All I know is I had taken a huge step toward that inner journey of whatever this was that would, the storyline that was going on right below the surface. It was like I was living this dualistic life so I had these, both the dialogues going. One, I was outwardly projecting, and the other was this side, this private, silent, secret life that’s going parallel to that life. I stopped thinking of myself and I started thinking of her. And it seemed like that parallel, those parallel lives intersected at that moment.


In 1997, give or take a year or two, I was working out on Fire Island, a barrier island, off of Long Island, and I worked at this little restaurant called El Hot Spot. It was a Mexican restaurant with a generic name, you know, a Mexican name. And I was told that I could wear anything that I wanted. And in fact they encouraged me to dress up, be myself.

I was wearing church dresses, sort of with hats sometimes. All different kinds of wigs. And I didn’t know much about makeup but I had some girlfriends that started to help me with the makeup and stuff. I was given this creative freedom. I had basically lived as a gay man and Pearl hadn’t emerged yet and so I was wearing, I just tried to put together things that I could find. They had a lot of, I was wearing, they would have a lot of the old drag queens out on the island would retire and their drag, and they would put it up at yard sales and I would go shopping, that’s where I did my shopping in the beginning because I dare not go into any store to buy women’s clothing.

And so I was getting ready to come into the city and I was going to go through my whole routine, put on, back into my male clothing and get ready to come back. Simple, I had done it a thousand times. And at that time, I couldn’t get it together. I couldn’t change my clothes. And I couldn’t get out of my drag to go back into the city. And I felt so schizophrenic and I started talking to myself, I said, “Okay, now Pearl, come on off it.”

Or I might have even talked to Ken. I said, “Okay, chop chop, let’s get it together, let’s get on that boat, take off these clothes.”

And it was like Pearl came out of me and said, “I’m not taking them off.”

It was like, I said, “What?!”

And she said, “I’m not taking this dress off.”

And I’m holding a conversation with myself, I said, “Of course you are!” I said, “We can’t go…!”

And so I went up to the Ice Palace and I remember talking to one of the entertainers there. I said, “I’m going back into the city just like this.”

And they said, “No, Pearl. You gotta take it off because you could be beat up. Or you could…”

I said, “Pearl won’t take, let me take the drag off.”

I know he probably said, “This child’s been doing a little too many drugs.”

So I ran home, got my bag, got my stuff, and I got on the boat. It was the most surreal trip across the bay, from Cherry Grove back to Sayville. And I’m on the way in and people are looking and I look just like what I am and I go in and I remember walking through Penn Station and I’m in a flowing something and people, when I looked like in my wake, you know how you walk past somebody and if you look back real quick in your wake, there’s all these people staring like, “What?!”

And I get on the subway and I catch the train on back down this way. Now it’s getting ready to just throw everything out that I thought I was: a gay, black man living with HIV. And now this new, new something has emerged that was peeking out all the time. Pearl was there. She didn’t have a name but she was there. Everything up to this point had led to me being true to myself as a transgender woman. And I, at that point, I had no idea what that meant because for the next 16 years, and it still continues today, it’s been a journey. And I wouldn’t trade it for the world.


The year was 2000. I was living my life as a woman, as Pearl. I had not changed my name. I had not transitioned yet. I was not only in therapy for support, I was getting therapy and primarily it was focused on Pearl.

Me living my life as a transgender woman, and what did that mean. One day I was walking across 14th Street and I was in this flowing material and I was walking across the street and I remember passing these two construction guys. And as we passed, they stared at me. I didn’t lock eyes with them but I looked straight ahead. And I heard one say, yell, “That’s a man!”

And I didn’t look back and I kept walking but it was, it was like somebody had kicked me in the gut. But I didn’t stop, I didn’t look back, I didn’t know if somebody was going to throw something at me or one of the guys was going to run back and hit me. You know, your mind just goes a little cuckoo but I just kept my composure and kept walking towards my destination and I can’t remember where I was going at that time.

Another time, I was on a, I was on my way to therapy, and I got on, I catch an uptown bus. I got on and there was this guy, I didn’t think much of him at first until he started mumbling and we’re holding on the pole together on the bus. And he started mumbling and started looking at me and started really acting very hostile. And I noticed, I kind of gave him a look, a once-over, and I realized, “This guy seems a little bit like skin-headish.”

And so, and he had his hand in his pocket with something and he was mumbling and he was, and I was nervous, but I didn’t, I couldn’t move. He eventually got off first and he started bumbling louder and he got off. And I started to breathe easier. And as soon as I got off I, and got to my therapist’s office, I immediately told her what had happened, and what had happened, and she had suggested that if that happens in the future, get off the bus if you can. Or move closer to the bus driver or do something. Just don’t stand in the line of fire.

Now he could have been a paranoid person and maybe it wasn’t even about me. But being, it was that first year, I’m very self-conscious, anything that, I’m very self-conscious of my, not only my me, my body, but my environment and I think, my safety, my life kind of depended on it. It wasn’t that outrageous. And so I realized that, you know, this is going to be, going to be something that I’m going to do but again, Pearl was right there saying, “I don’t care what you gotta go through, we’re not going back to living as Kenny.”

It was almost as if I was at the point of no return. It was like the journey all lie ahead.


During that first year before any, before my transition, I, the day before, I went to the dog, took my dogs to the dog run as Ken. And I went, I was popular at the dog run, speaking and my little routine. The dogs playing with each other and no different from any other day at the dog run. Then I came home, then I came back and the following day, Pearl went to the dog run.

People recognized my dogs. They saw me coming and, but I walked in and then as I got closer people realized what was going on, who it was, and I came in and I had my dogs and I was afraid to go up to anybody because of rejection. I remember this friend came over and just started talking to me like everything was business as usual. And it was just such a relief that I found, like an island of relief in this territory of anxiety and I guess I had projected enemies or whatever. And then as this person kept talking to me, more curious people came and started talking. And people asked, they said, “Well, what’s going on here?”

And when they asked me, I told them. And then I noticed behind them there were people who didn’t even look at me and we talked all the time and they kind of got their dogs and drifted out of the park. And it was hurtful. So as a result in the beginning I start walking around with kind of cautiously, kind of, I didn’t know who was going to accept me and who wasn’t. And I knew I had no control over it. And that day at the dog run was a perfect example. And that was just one of many because I still had to live my life going to grocery stores, the cleaners, the laundromat, all of the businesses around here, all these people know me. I was friendly with all of them. And there I did pretty well.

So for anybody transitioning, do it for yourself. Do it, come from a place, from some place inside for you and you don’t have to rush. Stop and take your time and nurture yourself and if you don’t feel like you have to do something, if you don’t feel like you can do something at the moment, don’t do it if it doesn’t feel safe. So talk with people. Ask questions. Get support. You make a lot of mistakes, trial and error, but I’m telling you, it’s a journey and I, it’s beyond my wildest dream.


The big hurdle for me was telling my family about my living as a woman now, living as a transgender woman. What I did is, I went to a friend’s art opening and they took a wonderful picture of me. So I had that picture blown up or made into a photograph. I wrote in a little note in the picture saying that my name is Pearl, I, this is, this is how I look and I closed the thing, I packed, and I wrote addresses and I put stamps on it and I mailed it all.

Then I followed it up with a telephone call. I waited until I thought that everybody had gotten the pictures. I called my mother first and said, “Mom?”

She said, “Yes?”

I said, “Did you get my picture?”

She said, “Yeah,” she said, “What was this all about?”

Like she, I said, “Well, Ma, did you get it or not?”

She’s beating around the bush. She would have loved to have said, “No, I didn’t get it” and maybe it would go away, but it’s not going away.

And she said, “I got it, what is wrong?”

And I said, “Nothing is wrong,” I said, “I wanted my family to know what’s going on with me and include you in my life.” And I said, “I’m telling all of you.”

She said, “Well don’t tell your oldest brother.”

I said, “Too late, Momma. I sent him the same picture.”

“Well how about your sister?”

“I sent her a picture, too.”

“And I assume you sent Junior a picture?”


And that was that. That’s how I came out to the family.

I didn’t hear anything after that. And then a few months later, this was about 2002. My bell rings. I go, I’m here with my lover, we’re in the bed, my lover is no clothes on, I go to the intercom and I said, “Who is it?”

And my nephew says, “It’s Todd.”

I said, “Todd?”

“And grandmother’s here with me.”

And she says, “Bernie! Open the door!”

And she’s looking at me and she doesn’t know what to say, and I knew she’s taking it all in. And she said, “Well, Todd’s having a dinner party for us. Tonight.” And she said, “And you’re expected to be there.”

I said, “Oh, you want me to come? I’ll be there, I’ll be there.”

And I came in a, I dressed, and I don’t know what possessed me to wear a blonde wig. I felt it. And when I came in, I found this a little endearing. My mother said, “Oh, why didn’t you wear the other hair? I loved it!” In some kind of odd way. It was like she liked that look.

So anyway, things were going well. My nephew cooked a beautiful dinner and we sat, I met a lot of the other relatives, everybody was a little stiff and a little awkward because, you know, I’m meeting them for the first time, they realize I’m transgender, my nephew is so happy to have my mother and me there, but I see he’s still a little nervous but sweet, sweet man. After we ate dinner, I went into the living room and started talking with some of the people. I’m feeling more comfortable now. And then all of a sudden I hear this voice saying, “Bernie! What is all this?”

And it sounded familiar. And when I spun around, it’s, I see that look in my mother’s eyes, of back when I was a kid and she was like a little drunk. And she looks at me and she said, “What is this?”

And she strikes my breast. And I said, “Momma, what are you doing?”

And I realized that she’s drunk. And she, that’s when she said, she came in close and she said, “I just want you to know, that West Palm Beach is not big enough for Pearl and the Bennett’s.”

So she’s getting a little drunker and I know she could be violent. So I got up and I said, “You know, it’s time, my gut feeling was telling me, it’s time to leave. The party’s over.”

And I went into the kitchen and I thanked my nephew and I said, “Todd, thank you. The dinner was wonderful.” I said, “Thank you for inviting me” and I said “I, I’m not going to be spending the night.”

I walk out the door and I don’t say anything to my mother because I don’t want her, I just want to get out of there as quietly as possible. And when she heard the door close, she realized I had left the room, or left the apartment. And she opens the door, she flings the door open and she yells, “Bernie! Get back here!”

I don’t look back. And I walk to the elevator at the end of the hall and I pressed the down button and she’s yelling and she’s screaming. And the doors open and she says, “Come back here now!”

And the doors close and I can hear her still screaming and down I go.

And she called the next morning and said, “Didn’t we have a great time?”

And I said, “Momma?”

I said, she said, “Are you coming now? We’re going to do something tonight.”

I said, “No, I’m not coming.”

And she couldn’t understand. And I realized then she was in a blackout that night. She didn’t remember anything.

When I left that apartment, I felt like I was, I had been ostracized from my family. And that I no longer had a childhood home to go to, go back to.

I no longer saw my mother in person while she was alive after that visit. I, even though we spoke on the phone almost every day. And I, we made peace with each other. I forgave her. And I knew I loved her. I was able to tell her that before she died. I, and at the funeral, it seemed like I had come, I remembered that conversation we had had at my nephew’s house that West Palm Beach wasn’t big enough for Pearl and the Bennett’s, here I stand in front of my childhood home in West Palm Beach. The home of the Bennett’s and certainly there’s more than enough room.


The year was around 1997. I went out, it was Gay Pride weekend. I marched in the Gay Pride parade with some friends in New York City.

They were throwing beads off of one float or maybe several floats. And so I ended up getting some of the beads and the ones I liked were the ones that looked like pearls.

So I was wearing them in the parade. And that weekend, after the parade which was on a Sunday, I was going to spend about a week or maybe a little short of the week, out on Fire Island. And so when I went to Fire Island I wanted to stay in that festive mood so I took my pearls out with me. My beads. And so I got out to Lee’s house and it was Lee’s lover, his name was Byron, he was a chef there. And so I went by to see the restaurant and to see him and to eat and see what he, what he does there, see him do his thing. And he was saying, “Oh my gosh” he was rushing around, there was no, part of the staff didn’t show up, I think they didn’t come back from the Gay Pride parade. They got drunk or something and didn’t catch the boat back. So I said, “Byron, can I help you? Let me do something.”

And he said, “Oh, no, you’re on your vacation.”

I said, “I can help.”

He said, “Okay, help me. Start by just clearing the tables or taking somebody’s order.”

Because I had been a waiter before and stuff. And I said, “But there’s one thing if I must have if you want me to help you. I have to wear my pearls.”

And I remember he said, “Okay, get those pearls and come on!”

So I ran back to his house and got my pearls and came back with the pearls. And so there I was, I was clearing and I was taking orders and I was doing all this stuff. So the guy in the kitchen, he yelled out, he says, “You, with the pearls! Your order is ready!”

And so I said, “Me?”

He said, “Yeah, you, Pearl!”

And I said, it was like, ding! Ding! It started, I said, “Oh my God, I like that, the sound of that! Pearl.”

Well let me tell you, from then on my name was Pearl from then on to this day. I kept the name Pearl. And he, I don’t even think he realized that he named me at that moment. And so people would always ask me, “How did you, how did you get the name ‘Pearl’? Is it from your grandmother or your great-grandmother?”

I said, “No, my grandmother’s name was Julia.”

But it all came from the pearls that I was wearing from Gay Pride Week. And so I loved the name. It’s one of the funniest ways to get a name. So you never know how you’re going to get your name but I got my name and I love it.

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