Matt didn't know it was possible for a girl to have a dick before the model pictured in his Hustler_-esque mag drew seven inches. She had slipped in unannounced between the magazine's other, more typical spreads. His stroke quickened, sticking with sweat in his Brooklyn bedroom while a worrying thought knocked in his skull_: Did it mean he was gay?

I met Matt in his home, thirty years after that fateful day in his teenage bedroom. (His name has been changed to maintain anonymity.) We sat on opposite ends of an ultra suede sofa, he in a pair of basketball shorts and a white t-shirt. Now in his late forties, Matt is a solid man, limbs thick from decades of manual labor. He's safe now, free after years spent in anguish. "It made me mentally ill," Matt said, his rough mouth blackened by 5 o'clock shadow.

Read More: Learning to Dress as a Trans Woman

In the 1980s, it was particularly daunting for a trans amorous man to confront his sexual identity. "The stigma that went along with being gay at that time in my youth was horrible," Matt said. "There was nowhere to go, no LGBT Center. Most people when I grew up didn't even have cable." He felt he had a lot to lose—not the least of which was an attachment to his identity as a heterosexual man.

In a different society, I don't think it would be an issue with me at all to be with a trans woman.

There are many men who share his fear. On Reddit, arguably the most revealing cultural sampler of our times, one trans amorous man recently aired his turmoil. He wrote about his relationship with a trans girl and his family and friends' rejection of her. According to him, his loved ones mock him, ask if she's got a dick, call him gay. "She is pre-op but I still only see her as a girl," he wrote. On other boards, users ask straight men if they'd consider dating a trans woman. Some guys give a flat out no; others appear unburdened by social stigma, down for it so long as she passes well and is hot. But there's another prevalent response, one that lands nearer to the heart of this issue. User kelevra206 wrote, "In a different society, I don't think it would be an issue with me at all to be with a trans woman, but... with the way things are, I just couldn't do it."

Matt's first sexual experience with a trans woman was in 1987, with a girl he picked up on the West Side Highway. This stretch of New York road runs parallel to the Hudson River, from the southern harbors of Manhattan to the Upper West Side. It used to be an infamous pickup spot for trans sex workers. Though Matt loved the sex itself, it wasn't long after orgasm that he felt a throat-clenching sense of anxiety. "I was driving her back and I was so nervous, 'Is someone going to see me?' Absolute fear—HIV, Did I give myself HIV? I was so afraid [thinking of] how I'd tell anybody."

It was the height of the AIDS epidemic. A disease that anybody could acquire had become a profound symbol of the cultural stigma against queer sexuality and sex. "There was no cure," Matt said, shaking his head. "Instant death, you're gone. We used condoms but I was more afraid of that conflict." The internal conflict Matt felt between his identity as a straight man was even more frightening to him than the threat of acquiring HIV: The illness might have meant a tragic, untimely end to his life, but it also would have branded him a fag.

Matt said that he's seen countless trans sex workers throughout his life. He was a John—or generic male client—for thirty years. Despite his insecurities, though, he always wanted more from those relationships. He tried to romance girls, but he was continually rejected.

[Having sex with trans women] has had no bearing on my identity as a straight male.

"The women that work in the sex trade have a wall," he explained. "I guess it's because of men. I don't know if it's all of them, but the ones that use the girls. Most men aren't willing to give the same that they give to a cisgender woman." Even guys who aren't hung up on their sexuality seem hesitant to take trans women seriously. While researching this story, I trolled Craigslist for other trans amorous men. Only one man, Alex, answered my request for an interview. He was very clear: "I was not worried it made me gay at all," he wrote. "[Having sex with trans women] has had no bearing on my identity as a straight male." Like Matt, Alex also discovered his attraction to trans women through pornography. He was 22 at the time, and he's now in his late thirties. While he claims never to have grappled with shame, he did affirm the taboo of his attraction. "I certainly wouldn't have told my friends," he said.

When I asked Alex how important it is that a girl is able to pass well, he responded, "I'm attracted to femininity, not masculinity. It's that simple." People are entitled to their own tastes, but one wonders to what degree this extreme devotion to masculine or feminine ideals is a result of being inundated with hyper-gendered imagery in pop culture. Not to mention that holding trans women to a cisgender standard is unrealistic: The majority of trans girls will probably never pass perfectly. Clearly, having a boner for hot girls with dicks is far from synonymous with undoing the stigma against loving transgender women.

Later in his life, Matt has tried to give transgender women more—he's tried to surpass the stigma surrounding his sexuality by being available emotionally and forging real relationships with trans women. About ten years ago, in his late thirties, he met a girl in the sex trade named Alicia. She'd come to New York from Brazil in the 80s—around the same time he'd been cruising the west side highway. "She's the first trans woman I ever kissed in public," Matt said. "We were walking down her block, and I was nervous: Is someone going to see me? I remember her saying to me, 'I'm walking down the street with you, but if you're going to be embarrassed by me, I'm going to be embarrassed by you.'" Then he kissed her. Matt smiled, gently shaking his head at the insecure man he'd once been.