By Jay Webster

I remember when I was 15, and my mom requested a girls' night — something to bring us closer together while she taught me everything she knew about makeup and hair curling. I obliged, of course, because I love my mom. We listened to music and joked about my friends. We were happy together as we put the final touches on my makeup. And then I looked in the mirror.

I immediately burst into tears.

My mom stared at me. Her confusion turned to anger as she grabbed all the makeup off my shelf and walked out. I collapsed to the ground and ran my hands over my face, ruining my foundation. I remember my tears stinging my eyes. I felt disgusting but more than anything I felt like I had let my mom down.

She had only ever known me as her daughter, but I knew in that moment, that was something I could never be. I didn't recognize myself in the mirror.

I didn't look my mom in the eye for days.

Jay Webster with his girlfriend Zenia. (CBC / Trevor Dineen)

When I was 13, I asked my friends to call me Jake, and refer to me with they/them pronouns. My friends told me that that wasn't my birth name and that I was a she, and to stop being silly. It felt like they took extra care to call me she after that. Never they. Never Jake.

The sinking feeling in my stomach every time they called me by my birth name confirmed what I had been scared of for a very, very long time. I went home that night and, despite my atheist upbringing, looked up at my ceiling.

Please let me be a girl, I begged. Please don't make me be Jake.

God only tuned in for the last part.

My name is Jay Webster, not Jake Webster, and I came out as a trans boy (female to male) in late October 2017, about 20 days after my 16th birthday. This year I went to the 2018 Winnipeg pride parade, with a whole crew of friends and moms to accompany me. Our pride festivities and outfits were themed around the colour blue, as a parody of an 'It's a Boy!' gender reveal party. The theme was picked by yours truly, of course.

Jay Webster and all his friends get ready to go to pride Winnipeg. (CBC / Trevor Dineen)

Getting ready for the parade and being surrounded by so much support meant the world to me. I felt as though I finally belonged somewhere, and that people understood what I was going through. After feeling like someone had locked me in a closet from the outside for almost four years, I was finally allowed to step out and scream my truth.

I danced at the parade without worry, made jokes about being trans to my mom, and nearly cried when we all remembered our favourite memories of each other. The parade sucked every bit of energy out of me, but I was happy. I was the happiest anyone had seen me in a while.

Chris, Jaime, Jay and Nolan Webster. (CBC / Trevor Dineen)

Of course, not every day is a pride parade. My family still struggles with me, and my pronouns, and my name. They struggle with the idea of me giving myself a needle of testosterone once a week, and growing facial hair. I still struggle to understand why my family can't just understand what I'm going through, dang it! We all struggle with the sudden mood swings and bad days that happen all too often. I struggle with the mirror, every day.

But I'm out. I'm out, and I'm proud. Maybe I'm not the daughter my mom wished for, but she couldn't be more proud of the son that I've become.

My name is Jay Webster, and I have never been, and never will be, a girl.

To hear the gender reveal party and Jay's full interview with Now or Never, click the listen button above.

This encore Now or Never segment originally aired in June, 2018