My dress looks better on him

and other challenges we face now that I know my boyfriend is trans

At 2 or 3 in the morning, he kept poking me. “Are you awake? Are you awake?”

“I wasn’t.”

“I don’t know how to tell you this…” he said.

“Then don’t. Let me sleep.”

But then I thought I heard the creeping sound of tears edging into his voice. And that woke me up.

“What is it?” I said.

“I can’t tell you.”

“Look, you obviously want to tell me, or you wouldn’t have woken me up.”

“No,” he said. “You don’t get it, I can’t tell you.”

My mind raced with possibilities, some particularly vivid. I recalled the time an ex had confessed to killing small animals for fun. But I shook my head because Sean was so different, special. We had just celebrated our 3rd anniversary and he was having me look for rings I liked.

So I poked him back, prodded him, cajoled him until finally, nearly an hour later, he told me:

“I think I’m trans.”

“Oh my gosh.” I said. And I hugged him very tightly.

“I feel like a girl. Does that make you want to leave me?”

“No.” I said. “I’ll stay with you, definitely.” And then I fell back asleep.


It’s been about 3 weeks since he told me, and he’s slowly realizing that I’m serious. I’m not going to leave him.

I still call him Sean, and he wants me to call him “he/him/his/boyfriend” for now, though when he wears a dress in the privacy of our room, I switch to calling him “she/her/hers/girlfriend.” And when I do, she glows with joy.


Sean is incredibly attractive as a boy. And I’m sure, though he isn’t, that he’ll be a stunning girl, too.

I brought him to Walmart and picked out foundation and eyeliner and lipstick in all the shades he’ll need. I spent an hour combing his hair and doing his make up and when I was done, she was beautiful. I gave her a maxi dress I’d just bought online, and when she slipped it on, she looked about 5 times better in it than I did.

She spent about another hour looking in the mirror and taking selfies. She sucked at taking selfies, too, so I showed her the “Myspace Angle” — how to hold the camera up and look up at it to make your eyes look impossibly large. And she started making peace signs and cutesy faces at the camera.

And I’ll admit, I had some moment’s pause.

When I started dating Sean I was sheepishly proud of how attractive he was. When I walked down the street with him, girls turned their heads. If I went to the bathroom at a bar, I’d come back to him surrounded by a gaggle of college girls, his tall head rising from the crowd.

There were so many reasons I loved him that I told myself I shouldn’t be ashamed of the pride I took in his masculine appearance. But now I wonder if that was hubris.

Because while, as I boy I took so much pride in his height, his muscles, his strong jaw, those are all of the features that might give him away in the future. That might put him in danger.


Being trans isn’t safe. And just to make things even less safe, Sean isn’t white.

…as I write this I realize that I’m soon going to be in an interracial, homosexual relationship with a trans woman. Wow.

…as I write this, I realize that I’m soon going to be telling my mom that I’m in a homosexual relationship with a trans woman. Wow. Maybe I should have mentioned to her that I also like girls before now.

…as I write this, Sean is putting on makeup. There’s a bit of a learning curve, admittedly. But when he’s learned that liquid eyeliner should not be applied as if one is a panda, she’ll be a force to be reckoned with.

Does this weird me out ever? Sure.

But, as I now imagine three times a day, if someone were to ask me why I’m staying with Sean, I’d say:

“I didn’t fall in love with a penis. I fell in love with a human soul.”

It probably helps that I’m pansexual though, let’s be real.

I get cold inside when I think about if I had been straight and he told me. What would I do? What would he do? He’s already told me that I’m the only reason he feels comfortable pursuing transition… would he just suffer in silence forever?


My name isn’t Lucy and my boyfriend’s name isn’t Sean. But the world isn’t friendly to trans folk, and I think it’s best to be anonymous until he tells everyone. He knows I’m writing this, and I’ll let him read it. Maybe once in a while, she’ll even chime in, who knows?

For now, I’m going to vent here. Because having confrontational fantasies three times a day with imaginary aggressors isn’t healthy.

And because I know there are others out there like me, going through the same things. Let’s not be strangers.

So if you want to tune into my occasional ramblings on this topic, feel free to subscribe, either to me or to the publication I’ll be creating for stories on this theme.

Have a nice day, guys. And remember, be kind to strangers because you never know what they’re going through.