When a straight man falls for a trans woman

Many men were privately in relationships with the women who were actively seeking suffrage. Many whites were in private relationships with blacks fighting for civil rights, unwilling to run the risk publicly but supportive nonetheless. And behind many ‘out’ gay men and women were ‘straight” people, lovers who, likewise, acted on the ‘down low.’

Many in the transgender community have similar relationships. “I define myself as a straight man,” said Jack, who is in his early thirties and in a relationship with Diane, an attractive, middle-aged transwoman whom he often meets for cocktails and a private tryst. “I have never been attracted to men, so I don't identify as gay or bisexual,” Jack said.

I asked Jack how long he has been attracted to transwomen. “At least since I was a teen,” he said. “I remember seeing Eddie Izzard in Dress to Kill. I wasn’t necessarily attracted, but I wasn’t repulsed either. I began watching transwomen in porn with other women and finding that much better than watching just two straight women. And from there everything just kind of snowballed.”

“And when did you act on that?” I asked.

“It was a few years after, with a pro,” he said, laughing. “I convinced her that I shouldn’t have to pay her. She seemed to enjoy it too much… I guess that scratched the itch just enough to motivate me to explore it further.”

“I identified as a straight male crossdresser, for a long time,” Diane explained. “Then one night at a gay bar I used to go to, I mentioned it and a friend said, ‘Bullshit… You just haven’t met the right man.’ She was right. Not long after, the right man came along … a really polite and respectful guy. I guess you could say he romanced me…”

I ask each of them if their relationship is only sexual. “Yes,” Jack said. “But we’re friends too. I guess we put a little spin on the ‘friends with benefits' thing.” In fact, all of his relations with transwomen have been primarily sexual. “Unfortunately, there haven't been any that weren't. Ours,” he gestured to Diane, “is the closest to being more. But we’re very open. We aren’t exclusive.”

Diane nodded. “I guess it is, but we are very good friends. I mean, sometimes when we’re together, we don’t even have sex; we just spend a long time talking. I think the most important aspect of the relationship, for me at least, is that it affirms my feminine identity. He interacts with me as a man to a woman.”

Jack has also had relationships with cisgender women, so I asked, “How would you compare those with your relationships with transwomen?”

“Well,” he said, “If I’m seeing a cisgender woman and a transgender woman, it’s no different than seeing two women, regardless of their gender identity. The problem is that It always becomes a juggling act. The relationship with the transwoman collides with the other relationship. But usually the sex is better with the transwoman.”

“How about a long-term, live-in relationship with a transwoman?” I asked.

“I've never really given myself a chance to date a transwoman.” Jack said. “On a couple occasions when I met someone that could have happened with, I also was in a relationship with a cisgender woman. But if the transgender relationship were exclusive, I would definitely consider it.”

“And you?” I asked Diane.

“I’d think a long time before committing to it,” she said. “Years ago, before I came out, I was married to a cisgender woman. Then we separated, and she threatened to expose me. That was not a good experience. We divorced, and I never looked back. I enjoy the freedom I have now too much to get very serious with anyone.”

When asked if friends and family know of their interests, Jack said, “I'm pretty sure my immediate family would be understanding,” then paused. “To tell the truth, none of my friends or family know about my interest, and I'm afraid of how much shit I would get from everyone else. They all think I’m just an average guy.”

Diane likewise replied, “I don’t share the intimate details of my sex life with them, or with anyone, for that matter. I wouldn’t be talking to you if you hadn’t assured me of our anonymity.”

“And how about your social life,” I asked them. “Do you all do anything politically or socially to help the cause of transgender people?”

“I’m out,” Diane said. “And I have actively worked for transgender rights. It’s not an issue in my life.”

“I support equal rights,” Jack replied. “And socially, if I hear people express bigoted views I speak up and try and educated them as best I can. But I know I can do more.”

“And what of a transwoman who transitions,” I asked him. “If Diane completed that process would you no longer be interested in her?”

Jack took a moments, then said, “I don’t know… I suppose if I truly love the person, allowing them to find themselves wouldn’t turn me off, but…” As his voice trailed off, they looked at each other, and then Jack leaned over and kissed Diane on the cheek.




Photo via Times of Malta

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