Men Who Love Trans Women: The Grandfather

I like women in general, but a trans woman is my ideal partner.
Cathryn Virginia
We're breaking the silence and telling their stories.

Cis men who love trans women are all around us. They’re our coworkers, our friends, our family members. And yet they’re rarely represented in the public view. The secrecy they keep has only led to misunderstanding, and in the worst cases, violence, as cis men often fear their masculinity is at stake. We’re breaking the silence and telling their stories.

Today we’re talking to Troy Kennedy, a 55-year-old Black man from Detroit. He lived on the down low for decades, and is now an outspoken advocate for trans amorous men.


My life is normal. You might even describe it as boring. I've been a white-collar professional for most of my adult life, and am currently employed in financial services. The gym is my second home. I love working out and staying ahead of the game. I love superhero and action films. One of my passions is cooking. I like to think I’m damn good at it now, at 55. Family is everything. I help care for my elder parents. My oldest son is raising my granddaughter without her mother. I’m an active, middle-aged, family-oriented, African-Amerian man from Detroit—and I’m also a leading advocate for men who are attracted to trans women.

I like women in general, but a trans woman is my ideal partner. My Facebook group, the Trans Supported Brotherhood, has been around for almost four years and was formed to help support trans amorous men to have a sense of community. Our members include both cis and trans men who date trans women. I volunteer regularly at LGBT Detroit, the largest Black run LGBT organization in North America. I've found a home at that organization, and they have supported me in my mission to help men like myself, who are attracted to trans women, to step up and walk in their truth.

It wasn’t always like this. I used to live a life of discretion and secrecy on the down low. Living a DL lifestyle was lonely, and harmful to myself, and to the women I wanted so desperately to connect with. My love for trans women began 37 years ago, in the summer of 1983, when I was just 19 and met a trans girl around my age. I didn't know trans women existed, and didn’t understand what it meant.


[If you're a cisgender man who is attracted to trans women and want to share your story, contact (you can keep your story anonymous).]

We were together for six weeks before she told me that she was trans. I couldn't believe she started life assigned male at birth. To be honest, my reaction wasn’t good. I was confused, scared and my fragile masculinity was threatened. In response, I tried to take corrective action, to reassure myself of my heterosexuality and masculinity. After the girl told me she was trans, I immediately had sex with several cis women to solidify my manhood. Nearly 40 years later, she is still my friend. But it took a long time for me to change.

Fear and confusion were the two most dominant feelings. I couldn't understand why, as a straight man, I was attracted to her, if she had been assigned male when she was born. How was that possible, since I’m not gay? Clearly, I had no understanding of gender identity back then, and neither did society.

Now that I knew trans women existed, I started noticing them in the world around me. One caught the bus everyday in front of my job. Another worked in the mall at a makeup counter. A year later, at 20, I moved to the Palmer Park area in Detroit, not knowing it was a mecca for the LGBT community. Thrusting myself into an environment that was rich in LGBT life forced me to confront it every day. It was overwhelming. So instead of truly addressing it, I just lived two separate lives to help me cope. The person who I’d always been to my friends, family, and colleagues, and then the man who secretly slept with trans women.


But soon, I started doing research, because no matter how hard I tried, I simply couldn't shake my attraction to trans women. Most if not all of the trans women I dealt with were extremely “passable.” Though that term is problematic and subjective, it’s the language we had. They were also gorgeous, exotic and embraced femininity in a way that entranced me. The sex I had with trans women was a bit different, to say the least. The fact that I enjoyed it troubled me.

During those years, I got married to the same cis woman twice, wanting desperately to be "normal.” I first got married in '92 and again in '96. My best man knew that I was secretly dating trans women, but couldn't find the words to talk about it. He just asked if I was sure I wanted to get married. He hugged me and said, "No matter what, you're my brother. If we have to, we'll shoot our way outta this church."

Our first marriage ended quickly, after 18 months. I never stopped dating trans women when we were together. That was selfish as hell. My ex wife still hasn't forgiven me. I understand why.

I've been walking in my truth for 20 years now. Everything changed when I started dating a cis woman who, like me, was attracted to trans women. We were sexually open, and after a night spent with her and a trans woman we met, I knew I could no longer live two lives. I've been dating trans women exclusively for 20 years now.

I felt isolated before. But I've seen everyone from actors, professional athletes, rappers, cops, pastors and regular guys secretly dating trans women. A number of men in my circle had also dated trans women, but no one talked about it until I stepped up. I’ve seen how my actions have impacted men in my community, and it has compelled me into action. I'm an outspoken advocate for trans women and the men who love them. While I once kept this part of my life a secret, today it's public knowledge.


When I stopped living in secret, I was afraid that my friends would abandon me. That I would lose my "man card." I walked around with that fear for almost 15 years. It was all unfounded. My dad is still best friends with a trans woman I dated for almost 10 years. My sons still call her Mom.

Most men who like trans women are isolated from each other. I’m in a unique position due to my activism. Because I'm living my truth and speak out as a trans amorous man, I know men who are married to trans women, have been in long-term-relationships with trans women, and those who are coming to terms with it.

Almost nine years ago, I was featured on my friend Diamond Stylz's Youtube page. Diamond has been an outspoken and dedicated trans woman activist for as long as I can remember. She allowed me to tell my story on her platform. Before that, I was a regular guest on Mieko Hick's BlogTalk radio show called T-Time. I've also had a Youtube page for almost 9 years called Ask a Trans Amorous Man. From the comments on YouTube, to the thousands of comments and contacts on other social media, I know my visibility has helped. Several men have thanked me both in person and online for being outspoken and visible. It can change lives.

Visibility matters. Feeling like you're alone in the world can lead to negative thoughts. I think it makes a difference when you see someone else like yourself in the world.

I had a co-worker who once saw me hanging out at Peanuts in Hollywood, an old trans-centric nightclub. When he saw me, he panicked and ran home. Halfway there he said, "Why the hell was I running?" I later learned. A few days after, a beautiful trans woman walked in with her family to purchase a vehicle. As I gazed at her, my co-worker whispered, “I like them trans girls too."