Straight Men Recall the First Time They Were Attracted to a Trans Woman

My first boyfriend was a straight kid from the Bronx. Alex—not his real name—was cerebral and boyishly handsome, but socially anxious. He was too afraid to go out with me in public, so our six-month relationship occurred entirely within my Brooklyn apartment. When Alex’s dad found out about me, he got mad, and said I’d been deceptive. Later, Alex told me his dad had admitted that when he was young, he’d beaten a trans girl for “tricking him.”

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

I tried to console Alex, but I'm not sure how much progress we made. Looking back now, I think what he really needed was a fellow straight man to tell him he was okay the way he was—that his attraction to me wasn't dangerous. But, for hetero men who date and fuck trans women, that sort of community can be almost impossible to find. Dozens of men contact me in any given week on dating apps. Most of them are unwilling to meet in public. They specifically describe themselves as “discreet,” on the “down low,” or “private.”

This secrecy means that many men who are attracted to trans women end up living a lie. And in the worst cases, that lie boils over into anger and violence towards trans women for putting their masculinity on the line. But there are cis, straight men who are working to break this silence. I spoke to four of them—across generations—about how they grapple with the taboo around loving trans women.

Chris, 57, is a white businessman and a male escort on the side; Troy, 55, is a Black father, grandfather, and Financial Services professional; Joel, 37, is a Black Information Systems Analyst; and Jeremy, 20, is a Black college student from New York City.

These interviews have been edited and condensed for length and clarity.

VICE: When did you first realize you were attracted to trans women?

Chris: In my late teens, while in college, my friends passed around a photo of a trans woman with a large penis. They made fun of her, but I found myself very attracted to the photo.

Troy: I met my first trans woman in 1983. I was 19 and she was 17. She was in trouble and I stepped up and took her home. I didn't find out she was a trans woman until six weeks later. I didn't know what that really meant at the time. I just know that I was attracted to her.

Jeremy: I first realized I was interested in trans women when I watched trans porn as a teenager. Trans women had previously been normalized for me on the Robin Byrd Show when I was about eight and I saw how they weren’t different than any of the other girls.

Joel: My attraction started with pornography and evolved into being a John and tricking with some street workers.

What happened next?

Troy: I literally built two separate lives. One was a heteronormative, married family man. The other was a guy who was familiar with and dated trans women.

Joel: I went back to dating cis women and didn’t bring myself to actually date trans women for a while due to the shaming that men, especially African-American men, receive—like the threat of being “exposed” for dating trans women. But I knew I was not happy dating cis women. In 2017, I decided that I’d had enough of what people would think, and succumbed to my desire of wanting to know and date trans women seriously. In 2018, I finally was able to get to know one lady and go on actual dates. During that time, Pose helped catapult my liking for trans women.

Chris: At one point, I started seeing trans women prostitutes. Not many, since I couldn’t afford to, but I did “experiment.” I then met a few girls via online chat rooms, Facebook, etc. I kind of became a sugar daddy to some women and would meet them as often as I could.

Jeremy: After I began masturbating to trans porn, I sought out trans women online. After that, when I was 18, I downloaded Grindr. I met up with my first trans girl. It was a good experience, and I met up with like 8 to 10 more trans women.

Is it important to you for a trans woman to “pass” as a cisgender woman? Also, do you gauge your attraction to trans women based on whether they’re pre, non, or post-op?

Troy: "Passing" is very subjective. Some of the world's most beautiful women are trans and I can tell that they are. It’s more about the feminine energies she gives off. I prefer pre-op and non-op trans women.

Joel: As of now, I have only dated two women of trans experience, both of whom were pre-op, but I am open to dating post-op as well.

Jeremy: The question is odd to me because the idea of "passing" is very situational and changes from person to person, so I'm just attracted to any trans person who I find sexy. Pre-op or post-op doesn't matter to me at all. I've been with people who are both and I don't have a preference.

How did you label your sexuality when you first realized you were attracted to trans women, and how do you identify it today?

Troy: I was a "straight man" and fought like hell to keep that label. That doesn't mean anything to me now. Sexuality is more fluid than people admit.

Chris: I always identified as straight. People see me as straight. It is not important to me today. 20 years ago, maybe.

Joel: I identify as a straight man, prior to and after dating trans women.

Jeremy: When I was at the age where I learned the labels to define sexuality, I just said I liked what I liked. The term “straight” holds no meaning for me.

When you realized you liked trans women, did you struggle with it?
Troy: I realized the fear immediately. There were only three types of sexuality in my mind. Straight, bisexual, or gay. I didn't like men, so I wasn't gay. That also meant that I wasn't bisexual. It took a while to understand that gender is a social construct. I was afraid, and walked around in a cloud of fear for more than a decade. I was worried about being called a gay man. I was worried about what my friends thought. I was afraid that my family and children would think less of me. But it never stopped me from pursuing trans women either.

Joel: Initially, I was concerned with what others would say, and was anxious on my first date, thus I hid it and did not tell any of my family members, close friends, or associates.

Jeremy: I experienced a little anxiety, but never really questioned my sexuality because I saw them as women. I was attracted to femininity and not masculinity. So I considered myself, like, straight and a little extra.

What sort of changes do you believe might be useful now, for men like you, to experience this sexual attraction and be able to accept it in a healthy way?

Jeremy: I think the best thing we can do for men to normalize relationships with trans women is for them to see trans women in non-sexual places..I think the biggest change in society that helped me but not older men was that I saw trans women represented in not just sexual ways. Like in the movie I Am Jazz. In high school, hearing about the big debate with Ben Shapiro and Zoe Tur—people were discussing whether we should gender trans women as women or as men, people were talking about trans women in sports. It was a cultural conversation.

Troy: Men need to come out of the shadows. I've hung out with professional athletes, actors, and rappers. I've partied with my boys in the neighborhoods and with celebrities. I've watched men from all walks of life date trans women in secret and in stealth. I've had family members, friends, and colleagues who have been with, have dated, or are attracted to trans women. Men need to stand up and stop lying. Men live in fear.

Cis men are not in danger because we are attracted to or date trans women. Our fear however, is killing trans women.

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