The Lucky One

Freshman Kai Jeffery discusses his journey of self-discovery as a transgender man


Freshman Kai Jeffrey waves a transgender pride flag in room 151 on March 29.

He knew those kids weren’t right. 

Granted, a fifth-grade Kai Jeffery didn’t know much about what transgender meant, and a freshman Kai Jeffery doesn’t remember what they even said. But he knew those preppy kids sitting behind him on the school bus did not know what they were talking about. 

So, he stood up on the unmoving bus and turned around to confront them. 

“That’s not what that means!” Jeffery said. 

“How do you know that?” the kids said. 

Jeffery didn’t have the words to respond — he knew what transgender meant, but he didn’t have the words to explain it to the people behind him. He quickly googled the definition of transgender. 

“Someone whose gender identity or gender expression does not correspond with their sex assigned at birth.” He read to himself. 

He felt something. 

This idea had been lurking in the back of his mind for a while. He related to those words, and this definition felt too close to home. It felt right. 

“I’m trans,” he said. 

“No you’re not,” the kids said.

The bus started moving before Jeffery could respond.  

“I thought I was a tomboy,” Jeffery said. “I never thought about it before that point. Then the dysphoria really popped up. I would notice how certain things didn’t feel quite right. It was weird.”         

Sometime after the bus incident. 

He hated how long his dead name was. 

It was six letters. Too long for Jeffery. 

He wanted to test out names. So he started scrolling through a baby names website. 

He’d used it plenty of times before when writing stories and having to name characters. 

“I’d decided on what I wanted halfway through scrolling before I even saw Kai on the list,” Jeffery said. “I knew that it was on there because I’d used that website before. But I hadn’t gotten to it yet, I was definitely actively looking for it. I’ve always liked it just because it’s short and it’s sweet.”

May 2019

Jeffery still wasn’t sure if he was trans, even after yelling at those preppies on the bus, even after deciding on a new name. But he knew he wanted his hair cut short. 

His regular hairdresser was out that day, so he was with a new person for the first actual haircut he’d ever gotten. 

He was nervous, he didn’t know if it would look good. But he was excited. 

“It was actually really cool,” Jeffery said. “ was really chill and was not at all upset that I was cutting off long hair to make a pixie cut. She didn’t try to make it feminine. It was really awesome.”

June 2019

Jeffery publicly started experimenting with his name and pronouns during summer school between fifth and sixth grade. He introduced himself as Kai. His peers and teachers started calling him Kai. 

“I asked one of the kids I’ve known there to use he/him pronouns for me,” Jeffery said. “It was really weird because it felt really good. It was a weird, subtle good. It wasn’t a big revelation. It was a ‘well, that feels normal.’” 

Jeffery was moving to a new school for sixth grade. And moving gave him an opportunity. He wanted to transition socially, publicly use his new pronouns, at his new school. 

He would have to talk to his parents. 

July, 3 2019

Jeffery didn’t want to talk to his mother. 

Texting felt impersonal. 

So he hand-wrote a letter, waited till the dead of night when his parents were asleep and put it on her bedside table. 

His mother slipped her response back under his door. 

He read his mother’s letter. 

“She said that she did kind of feel like it was a phase,” Jeffery said. “, I asked her if I could get clothes from the boys’ section. She said that she trusted my judgment and that it was up to me and that she loved me. She was warning me about the harassment I might have , and that my parents would support me either way.”

Since he came out, Jeffery’s parents have been increasingly supportive. They actively tried to use his name and pronouns. His mother has taken him to a Pride parade and she goes out of the way to help LGBTQ+ people at her workplace. More importantly, his parents helped him get binders, a gender-affirming drug for children called Oxandrolone and helped him get his name legally changed.

Jeffery transitioned, and he never truly experienced much backlash.

April 9, 2023

Since moving to high school, he’s had to deal with the occasional rude person in the hallway, but it’s never been like the stories of bigots he’s heard about on the internet. He’s developed a close group of friends. 

He’s also finally being moved onto testosterone. 

He feels overwhelmed, not because of the monumentality of this moment.

He’s just scared of needles. 

They sat in his father’s bedroom. He stuck the needle to the side of Jeffery’s belly button. 

It felt anticlimactic. Nothing happened. Nothing would happen for three to six months, according to the pamphlet. 

But as Jeffery looked back at his story, he realized he’s one of the “lucky ones” who were accepted for who they were. 

“I have parents who are very accepting and who didn’t really question it at all,” Jeffery said. “I also live a very comfortable life in general. It’s weird because I don’t know how feeling. I always feel the need to give advice. But I can’t really give advice for something I can’t do anything for and they can’t do anything for. So it’s really difficult.”