Kenya Black Dupree: give yourself a chance to live

"Nowadays, they say it gets better. But, back then, nobody was telling me that."

Kenya shares her story in her own words.

I was born in Milwaukee, Wisconsin. My grandmother was originally from Pasadena, California, and came to Milwaukee after marrying my grandfather. My mother was only sixteen when she had me, so she was very young. I was raised as an only child, although my father had five other daughters.

My family’s last name was Wimpie, but everyone who knew them, knew that “wimpy” was the furthest thing from who they were.

I spent most of my life in Milwaukee but bounced around a lot. I lived on 20^th and Meineke from age 7 to 10, and then moved to 60^th and Congress, and then 62^nd and Congress, and finally a house on 72^nd and Congress. I was basically raised up Congress, close to Capitol Court.

My mother was trying to grasp the concept of being a parent at 17, 18, at an age when most people are out partying. Until I got older, I didn’t realize she and I were actually growing up together. I wound up living with my grandmother. She’s really the one who raised me.

When I was growing up, people would say to my mother, “your daughter is so pretty,” and she’d get so mad to say, “that’s my son, not a girl.” I would laugh and she would hit me. She said, “you’re not a girl, and they don’t really think you’re a girl either.” She would get so mad, but the truth is I looked just like her. I think that’s why she kinda hated me.

The early eighties were the start of the crack era, and a lot of kids were forced to raise themselves due to that. 

We all went through a lot of stuff in those days. 

Finding chosen family

I met a lot of great people. I met this guy, named Gabriel, who became like a big brother to me. When I got to Craig Alternative, they’d already prepared everyone who I was and why I was there. So, there was this uproar, and I already had this reputation. So, when I got there, there were rumors that Gabriel and I had something going on. And he stood up for me that very same day.

My teacher, Miss McCullum, was the sweetest lady. She was like an animated version of Peg Bundy: she had the long nails, the big brown hair, and always so dressed up. She was so eccentric, and yet so sweet. She helped me navigate who I was during that part of my journey.

There was a classroom of like nine or ten kids, and I got to know all the people in it. There was no bullying, it was all about affirmation. Teaching you to love who you are, to love your neighbor, to grow into your best self. It was the most liberating experience I’d ever had. And through the course of that, I found out who I was. I feel like I came out of a trance.

I had already started dibbling and dabbling with shows. I met my uncle Michael Wimpie, who was the root of it all. My uncle was friends with drag performers Dominque Mahon and Basia Bazaar. He came from the old school with all those people. Dominique became my drag mother. She played an enormous role in my life. Dominique was the reason I wound up working at 219 with B.J. Daniels and Mary Richards. So, as I’m coming in, they welcomed me with open arms.

The only time I ever felt protected was within the gay community. They made sure that nothing happened to me, inside or outside of the club, and if they saw me on the street, they made sure I was good.

I planned to spend ninth grade at Craig Alternative, and then start at a new school. And my teacher said, “I hear you like to dance,” and gave me a brochure on Milwaukee High School of the Arts. “They have an audition coming up,” she said, and she agreed to talk to the teachers, and I got invited to audition.

After the audition, I was waiting for the phone call, and then I got a letter in the mail saying I got in for my sophomore year. I was so excited because I knew my life was about to change.

I was already out of my mother’s house, and we weren’t really speaking. I thought that leaving home meant they’d let me live with my grandmother. Instead, they put me in a group home, and later, two foster homes.

The first foster family was really nice. She was an older lady with adult children living at home. They were nice, middle-class people, but the son hated me – and I had to share a room with him. I was twelve, he was 17 or 18. He felt his mother treated the foster kids better than her own kids. He hated everything about me. The younger daughter also hated me, and we would fight. The only thing I knew how to do was pick up something and defend myself.

So, they found me another foster home with a wonderful Muslim lady. She had just gotten a divorce from her ex-husband. She didn’t care that I was gay. She had a son who was in the military. I was 13 or 14 at the time, and she didn’t have a TV. She had books and books and books. She had a living room that was empty, and later, I learned this is where she did her prayers. She taught me a new way of living, cooking from scratch and eating most meatless meals. I adopted that lifestyle and started living to my full potential. I started to have more energy. I started waking up feeling good in the morning. 

When you’re around someone with great habits, you start picking up those habits too. This really changed who I was on the inside.

The friend of a lifetime

During winter break, I met someone who would change my life forever. I was walking the hallway, and I saw the most beautiful Black guy. Beautiful dark skin, so confident, he had a real presence. And he walked up to me and said, “what’s your name?” And he said “OK, Miss D, my name is Ruben, and you are going to come with me, and we’re not going to let anyone fuck with you. I’m going to make sure you’re OK.”

That was the start of an amazing friendship. From that moment on, we stuck together. I went to his family’s house, and we shared a certain bond that I just loved. I didn’t know how to be around me. I didn’t even know how to be around boys. I always assumed they wanted something sexual from me because that’s what the experience always was.

He was not here for any of that. He just genuinely wanted to be my friend. he wanted to make sure that I was okay. Even now, I value him so much. We ended up becoming best friends that winter. People knew us as a team.

We started sneaking down to 219 to see the shows over the summer, and we were only 15, 16. We started getting to know all these people, and realizing, we can do this. I met Kelly, who was the most amazing person, and she’d do backflips off the stage. I remember meeting Ivana. I’d never seen anyone like that. She was wearing a long fur coat, a black turtleneck, jeans, and all her own hair. She was so beautiful, so feminine, so worldly. She had a boyfriend and lived in New York. And yet, she was so sweet to me. I was like, wow, that’s what I can be. She left an impression on me.

There are a lot of us from Milwaukee who are overlooked in the world, because they say Milwaukee is a small town. But a lot of big names got their starts in Milwaukee.

When I came back from the break, it’s almost like I was a boy. I got a haircut. I hit puberty. I was incredibly attractive. I started attracting both sexes. I started getting attention from boys and girls. It was really weird, and I was like, wow, maybe I don’t need to be a girl.

As I walked into school, it’s almost like they forgot who I showed up as, and they just accepted me for who I was, and suddenly I was loved by everyone in the school. I even started using the locker room.

During junior year, one of the engineers had his eye on me. My dance class had ten Black gay dancers, and we were all equally attractive. But he was really infatuated with me. One time, we were on the elevator together, and he touched me inappropriately. I decided to tell because I was tired of being victimized. Now, mind you, I didn’t tell because it was him, it just happened to be him that touched me next. I’d told myself that the next time someone touched me, I was going to tell because I was tired of people using me to fulfill their fantasy.

So, he got fired – and then, I saw him at the club I was sneaking into. He said, you didn’t have to do that. And I was like, do you know what? You’re right. But I had to protect myself.

My foster mother had moved into a beautiful new condominium right off Prospect Avenue, but I was still getting the bare minimum from her. I needed school clothes, school supplies. I still didn’t have a TV. It was time to go. 

Ruben was getting Social Security for some reason, so he always had money to take care of himself. It was a while before I learned why he was getting it.

Coming up, coming out

Ruben took me to La Cage and Tina’s. Most of the gay family would hang out there. That’s where I met Geneva Riches. I even did a show there once.

By the end of junior year, I was happy with being a boy. I met someone from the dance troupe War Play, and I joined the group. Next thing I know, I’m traveling the world dancing with them once or twice a month. They asked my grandmother, and she said “well, take care of him!”

I was still hanging out with Dominique, because we were backup dancing for all the big queens at the time: Shannon Dupree, Duwanna Moore. I got the bug to do pageants full time. We were in Madison for a prelim, and there was Tandi Andrews coming out half-naked. I’d never seen anyone more beautiful.

It literally just took off from there. So, every summer break through school, I would be a girl. I would walk around the city. I would do shows as a girl. I hung out with Tracie Ross and Lady Simone. They were closer to my age, and knew my family, so I felt safe hanging out with them. I started taking hormones with them.

I’m meeting all these people. I’m doing all this shit that I had no business doing. And now, it’s my senior year, and it’s all over the city that I’m gay.

I had to take the bus all the way down from 72^nd and Congress to 27^th and Highland. I had to constantly carry a weapon because people always wanted to fight me. And there was no law back then to help you. If you were gay, it was just like, you’re on your own. They didn’t care. We were catching the bus one day, and someone tried to hit me. I realized that I needed to find another way to get to school.

Ruben would never date Black guys. And I came from a dad who was a Baptist minister, and a foster mother who was all about pro-Black, and here we’re only dating white guys. I didn’t understand that at the time.

The darkest days

To this day, I still can’t believe Jeffrey Dahmer lived around the corner from my high school. 

Every Black kid in the ghetto was on edge, especially if you went to the clubs. If you’re going to 219, stay away from 219. Even my grandmother was like, I don’t want you to be next. It was kind of a scary time. I’m glad he was exposed when he was because I’d literally just gotten out of school, and I was afraid of what might happen to my family. If I went a couple of days without calling them, they always thought he got me

I knew some of the people that died. I knew Tony Hughes and his sister. We hung out at Tina’s, the black club. The Black gay community was small and tight-knit, and you knew everyone in that community.

My uncle died of AIDS around that same time. There were no medications available to combat the disease back then. My uncle died of AIDS complications related to cancer, but his crack cocaine addiction accelerated the disease. That heightened his chance of dying.

I didn’t know it at the time, but my best friend Ruben already had AIDS. That’s why he was getting Social Security. He was adopted, and his parents had given him up because he had AIDS. His adoptive parents loved him so much, and anybody that he brought home. They loved me like I was one of their own.

But now he was sick, really sick, and wasn’t getting better. We’d had a falling out, over something stupid, and he couldn’t get my phone number. So, he would call the school and send messages through the teachers to me. “Ruben wants you to come see him,” they’d say, but I couldn’t see him in the hospital. I didn’t know how I was going to process seeing him that way. I didn’t want to go that hospital.

I ended up not going to any hospital, because Ruben was moved to hospice. He ended up moving in with his boyfriend, this really nice white guy, and the guy took care of him up to the day he died. He was there for six to eight months. I wanted to see him, but it broke my heart to think he wouldn’t even look like the same person I knew.

My grandmother was diagnosed with cancer just as my junior year began, and then my grandfather started getting sick as well. I’d always been closest to my grandmother because she was the only person who accepted and protected me. So, I would spend the weekends at her house. After my grandfather died, she worried about living alone, so we moved into an apartment together.

It just made sense that we would wind up back together. She became mentally and physically dependent on me because she’d never been alone before. In a sense, we were both mourning together. She lost her husband, and I’m leaving my old self behind. I was trying to find my way. I just wanted to be loved, and I was looking for it in all the wrong places or all the places.

So, I’m going to paint you a picture. My best friend is dying from AIDS, my grandmother has cancer, and I don’t know where the hell my mother is. I literally haven’t heard from her in months.

It was just a hard, hard time.

So, I started to throw myself at school. I didn’t know about college, because I never thought I was good enough for that, and I didn’t know who was going to pay for it.

And now, I’m done with high school, and no one showed up for my graduation. Tracie and Simone were there as I walked across the stage. It felt amazing to get my diploma because none of my cousins ever did that. Many of my aunts and uncles dropped out of school. So, literally I got that diploma for my grandmother because I knew she wanted to experience that pride. I got that diploma for her. So, as I’m walking across the stage, the entire auditorium erupts in complete and utter applause. I never felt that in my entire life. It was such a rewarding feeling.

That just goes to show you how much I was loved in that school, and how much that school changed my life. Had I not gone there, I don’t think I would have ever been able to be the person I am. School of the Arts opened the door for me to be who I am.

After graduation, I’m 18, I’m out of school. And I get the call: please, we need to see Ruben, because he’s doing really badly, and he really wants to see you. I’d been avoiding this moment for months. This time was different. I went over to see him, and he wasn’t as bad as I expected. We sat and we talked. He was so small, and so frail, as I held his hand.

We were supposed to do everything together. We were supposed to move to San Francisco. But two days later he died. 

I don’t know if he was just waiting for me, but that was it.

Finding a path

Ruben’s passing kind of gave me a scare. I didn’t have the will to do anything. 

I wanted to escape all that, so I started doing more shows. I got a name for myself working at 219. My first name was Kenya Moore. Dominique got me hooked up with the people, even though I was still underage with a fake ID. I met BJ Daniels, the show director, and she was so elegant and glamorous. She reminded me of one of those old Hollywood starlets, so pristine and perfect. BJ was kind of the blueprint for the new girls coming out after her.

So, I’m working, I’m on hormones, I’m doing shows to survive. I’m fresh out of high school, but I don’t have any prospects. I got my very first job – as a boy – at the Gap at Grand Avenue. I’m taking care of my grandmother. I’m performing full-time and my grandmother is front row center at all my shows. She’d say, “that’s my baby, that’s my baby!” And everyone knew my grandmother, who was so sweet and so genuine. My mother started coming around, and we started to mend our relationship.

My grandmother lost her hair during cancer, so I shaved my hair off. We would go wig out together. I’m hanging out with Traci and Simone, and we’re going back and forth to Chicago.

After a year dancing with Spanky and the Four Play Dancers, I decided to stop dancing with them. I got tired of being a back-up dancer and a background singer.

I signed up with Cleveland Job Corps and told my grandmother I was leaving. She burst into tears. She cried, and cried, and cried, all the way to the Amtrak station. I went to Cleveland, and it was my first time ever out of Milwaukee. I was there two weeks, and my grandmother called every day saying how much she missed me and begging me to come home. After the program, I moved back in with her. And everything too off from there.

It just took off. I started living my life full-time as a girl. I started taking more hormones. My grandmother engaged in a lawsuit that eventually paid off big. She bought a house, with all-new furniture, and gave me the room directly across from hers. She made sure we were taken care of.

And now, my name is fully out there: Kenya Moore. She dances. She’s an amazing entertainer. And I’m working full-time at 219, and I’m leaving with good money. I’m going to Chicago to get pumped.

I begged my grandmother for the money, and she wrote me a check. “Is this really what you want?” she asked, and I said, yes. Because I thought that’s what I wanted, long-term. I’m 19-20 years old, and I want what everyone else has. I wanted this to change my life. So I went, and had that done, and came back.

Not even a month later, my grandmother’s cancer went to stage four. They took her bed out, and moved in a home health bed in. She was still able to walk around but couldn’t be left alone. I was there with her the majority of the time. After her passing, we saw that she had a new will, but she had never signed it. So, they divided up her estate across her eight kids. They left the house to my aunt, who hated me, because she felt my grandmother treated me better than she treated her. She threw me out of the house, so I ended up living with Dominique Mahan, and working more nights at Club 219.

When all that was settled, I came out of my family as a woman. And it’s almost like they already knew. I never had any moment of being ostracized from my family, which was a blessing.

Dominique set me up with her sister’s baby’s father, right in front of his sister. It was a big, big scandal mess. We were dating for a while, and then we broke up. Through the course of our break-up, I was also breaking up with Dominique. She started hating me. We were still working together at 219, but the Sunday crowds were dwindling, and it wasn’t like it once was. 

One night, she got so mad at me, she started to fight me. That was my last night working at 219.

Full circle in Chicago

I’d really taken off now. I was Miss Continental Wisconsin at the time. I started to travel to Chicago for Continental. My face got to be seen. People started to fall in love with me. 

I started traveling all over the country. I decided to go live in Florida. I changed my name and my gender marker on my ID for the first time, and that was something I didn’t even know could possibly happen. I was working at Nine West with Sunny Dee-Lite, and I didn’t even know who she was. We both started our transition at the exact same time. We instantly clicked.

I was living in Miami with my friend Raul and his mom, who lived across the street from a Haitian. I was the only Black person living in this Latino neighborhood. One day, the Haitians did a home invasion while I was at work and tied up the whole family. Where’s the girl? Where’s the girl? They kept asking. The mom called me, and told me don’t come back here, for your own safety. They bought me a ticket and sent me home.

I was born Demitris. People called me D. I started going by Kenya as my stage name. And growing up with the girls, they always said you need to keep your stage name separate from your daytime name. So, I was like, ok I get it. So, I kept my daytime name as D because that’s who I was. But now, I changed my legal name to Lovely Brown. My ID said I was female.

I got a job working at Hooters at Grand Avenue for a few months, until someone from my school came and told them that I was not a biological woman. So, they fired me, and didn’t even have to tell me why. That was another lawsuit I could have filed. Well, I kept the Hooters uniform, and I used to do shows in it.

I met a large group of trans women in Milwaukee. They were all from Chicago and California. I started hanging with them. I always thought I was this Afrocentric chick, so I changed my name again. I was now Najah Mohammad and I kept that name forever.

I ended up auditioning for the Baton. I took the Hooters costume with me, and I got hired there. I’d work there on the weekends and come back to Milwaukee on the weekdays to visit friends and family. That’s how I took off; that’s how I got out of Milwaukee.

There were no real bookings up in Milwaukee. So, I ended up staying with a roommate who just happened to be Angelica Sanchez, otherwise known as Angelica Ross from POSE. We lived upstairs of C’est La Vie. I had one side, they had the other side, it worked for an entire winter. We didn’t have a kitchen, and we shared a bathroom. I met Amailia Black, and I would go to Chicago, and she would show me the ropes on the weekends.

John Clayton was pretty horrible to us. He would make her go-go dance, and she said, “will you do it with me?” And I was like, “well, I got full on hormone breasts, so I can’t do it.”

She and I ultimately had it out because she got a boyfriend, and she started to transition a little more, and we were both sick of staying up above C’est La Vie.

So, one day, I said to Amailia, can you help me get a place? And she said, you can get a place in my building. Come down with $700 and we’ll get you the place. I said, okay, give me a month. I spent that entire month working up $800 some dollars. I rented a U-Haul, and I didn’t even have a drier’s licenses. I packed up all my clothes and a rocking chair in the U-Haul and drove an hour and a half away to Chicago. That was the end of my life in Milwaukee.

I met a guy in Chicago, who got too attached way too fast. He wanted more from me than I was willing to give, and he didn’t accept being rejected. He kicked in my door several times, trashed my place, and almost killed me. I was literally fighting for my life.

So, I left Chicago and moved to Atlanta for 10-15 years. Today, I’m back in Chicago.

Twenty years later, I’m fully transitioned into a woman. I just woke up one day and realized I didn’t give myself a chance to live. I did what I needed to do out of survival. I didn’t have the tools to deal with the loss of my grandmother or my best friend. I didn’t have the tools to deal with all that bullying. I used Kenya to escape all of that, which often came back to bite my ass, because here it is 20 years later and I’m still processing my trauma. I’m so proud of myself because I’ve made it to 47. A lot of people that I came up with did not make it.

I changed my name to River because the name Demitris had a lot of hurt behind it. I now had a chance to create the person I wanted to be. I want my life to be in front of me, not behind me.

After my grandmother died, my mother and I kind of built our relationship back up. I would go back to Milwaukee all the time, until my mother died in a car crash in 2006. For the next ten years, I wouldn’t step foot in Milwaukee, because it hurt too much. That kind of broke me.

She had been through so much, and as you get older, you start to offer grace. I didn’t understand everything she was dealing with, until I got older, and got to figuring it out. I didn’t offer any grace, and she didn’t have the tools she needed to raise a child like me. So, I get it now.

Most of my family is still in Milwaukee. My father is still down there. So, when Shannon told me, you need to do these shows at Hamburger Mary’s, I was all about it. I started performing in Milwaukee again.

Today, I’m an assistant manager for FedEx. I stopped doing shows about a year ago. They just stopped being fun for me. During COVID, I learned that when the lights are out, there’s nobody around to clap for you. So, if you don’t have anyone to clap for you, you have to look to yourself. I’m thankful for Covid because it allowed me to take a good look at who I was. What did I have to offer me? There were no clubs, there were no shows, you were stuck with yourself.

It was time to move past entertaining. I traveled all over this world and touched so many hearts. I’m thankful for the moments I’ve shared with the people I’ve met. I just knew I needed to move forward, to focus on myself and my future. I wanted a legacy for myself.

My aunt has been telling me for years to write a novel. And I made the decision last New Year’s Eve that I was definitely gonged to do that. My story wants to be heard.

They say it gets better. But there was nobody around me telling me that it was going to get better. 

I just knew that in my mind, and in my heart, that there had to be something better than this. There has to be. 

That’s how I knew that it was going to get better.