When I told my family that “I’m not a cross-dresser, women’s clothes just fit me better,” I knew they would believe the lie. Because I believed it too.

I’d always struggled with finding men’s fashions that fit me and made me look good. Since childhood I’d been both short and thin. School uniforms were always too big, and hung on my frame like elephant skin on a scarecrow (a simile that sounds less poetic when it’s being whined by a nine-year-old boy on a shop floor). Even in my final years of high school, when I’d begun taking testosterone pills to kickstart puberty, I had trouble catching up to my peers (although the rages I would fly into thanks to the medication’s side-effects definitely established me as a cool customer). I finished my education still rake-thin, and when the rules changed and we were allowed to wear our own clothes to class, I had to choose between buying clothes that fit but were made for 10 year olds, or clothes that were age-appropriate but made me look like a child playing dress-up.

After high school ended, I resolved to take charge of my fashion life. In fact, I wanted to re-define my entire life in general. School had never been fun for me, but I felt like university could be a fresh start. Rather than work on my self-esteem, work ethic, or inter-personal relationships with others, though, I thought I’d started with something more surface-level. I was sure a change in my appearance would magically summon up a better existence.

As soon as I received my student loan, I headed for the mall, determined to spend as much money as necessary to make myself look good. I visited all the stores I’d seen other guys my age buying clothes at, stores like Burton, Top Man, and Diesel. I even managed to find some clothes that fit me okay (mostly thanks to the popularity of skinny jeans, which fit like regular pants on my pipe-cleaner legs).

I still didn’t feel comfortable, though. I’d hoped that getting clothes that looked good would make me feel like I looked good. Instead, I felt like I was wearing someone else’s outfits, like I was still playing dress-up. I was convinced that I still looked awkward and out of place. My new clothes weren’t the camouflage I wished for.

I was frustrated, so I started to indulge memories of the only times in my life when I felt like I belonged in the clothes I was wearing. There were several afternoons growing up when I’d stolen my sister’s clothes and tried them on (though she was a year younger than me, she’d always been a size or two ahead, which was incredible for my self-esteem) I wore her jeans, her shirts, and even messed around a little with her make-up, never understanding what I was engaging in. I later dismissed those experiences as just teenage experimentation. But now there was a part of me that wondered if was there something more to what I’d been doing?

My dorm room was miles away from my sister’s wardrobe, of course, so there weren’t any female clothes around for me to borrow and try on. If I wanted to take a closer look at how cross-dressing made me feel, I’d have to pony up the cash and buy myself something pretty.

I tried to ignore my rapidly diminishing student loan money and headed back to the mall. I browsed the women’s section of the department store nervous and worried, convinced that everybody around me knew that I was a creepy pervert who wanted to prance around in women’s knickers. I mentally prepared a story about buying gifts for a girlfriend, and — without the benefit of fitting rooms — tried to choose clothes that looked like they’d work on my body. I got away with a couple of pairs of jeans, a few tops, and some ballet flats. I raced back to my room, eager to indulge myself with a fashion show.

I stayed up all night mixing and matching the few items I’d purchased. I looked okay, I thought, but it wasn’t the outfits I was focused on. It was how I felt. I was a little embarrassed that I looked like the stereotypical “man in a dress,” but that didn’t stop me from feeling like I was finally presenting myself the way I’d been meant to my whole life. I didn’t want to ever go back to menswear, but I knew that that would mean wearing women’s attire in public.

I psyched myself up and managed to run a test case, going to a corner store wearing my new pink blouse, deflecting any weird looks with a smirk. Inside I was terrified, but I tried to project an air of I-know-something-you-don’t. The next day I went to class in that same blouse, trying to maintain that false confidence.

My friends and fellow students were all members of the comedy program I was studying, so to them I passed off my new look as an Eddie Izzard-like transgression of societal norms, a strange comedic bit that they could respect for its daring nature (the class in general was filled with misfits doing weird stuff). My family was unsurprised by what they wrote off as just another in a long line of attention-seeking stunts on my part. (I’m pretty sure they figured it was less embarrassing than my obsession with unicycles.)

For a while, that was the new normal. I’d wear a couple of items of women’s clothing as part of my outfit and the people who knew me would just make a tiny joke of it, if they even mentioned it at all. When I was by myself, of course, I spent a fair amount of time figuring out just why I felt so good in my new clothes. I devoted days to trans-themed websites and message boards, borrowed books from the university library, and wrote drafts of blog posts that were quickly deleted. I came to the conclusion that I must be a transvestite. I’d always thought those people were gross, but I was apparently one of them. I didn’t consider myself gross, so I didn’t worry too much about it.

I started expanding the range of my new appearance. I dyed my hair platinum blonde and pierced my ears, nose, and bellybutton. I experimented with make-up, showing up to class wearing lip gloss and badly-applied eye shadow. I was blurring the lines enough that the people around me felt awkward when they said my name or referred to me as “he.” Clearly, I was more than just a transvestite, more than a straight-up cross-dresser, even. I was a little muddy on those terms (I still am, as is the larger transgender community), but I knew that those words were for people who either didn’t want to present entirely as the opposite gender, or who only wanted to for short periods of time. I didn’t want anything about this to be temporary. I wanted my new look to be my life.

I resolved to run another experiment. I would try as hard as I could to make myself look like a girl from head to toe. I wouldn’t just apply a couple types of make-up and mix a skirt with one of my high-school-era sweaters. I’d put on a full face and wear an entire outfit of women’s clothing. I needed to see if this was something I really wanted.

I’d have to fake some breasts, of course, which meant buying a bra. I definitely wasn’t confident enough to get a fitting (and I worried that even asking for one would be grounds for police action), so I tried to gauge the sizes by sight and picked out a beige B-cup. I read on the internet that pantyhose filled with millet seed made for good bra-stuffers (with the bonus of making you smell like delicious millet), and I researched how to duct-tape some of the looser skin on my chest to gather near the top of the brassiere and give the illusion of cleavage (which, yes, led to a frantic late night Google search of “duct tape solvent”).

I timed my full-outfit trial to coincide with a stand-up comedy performance, so that if anybody asked what I was doing I could say it was all part of a character piece. I picked a temporary name for myself and roped my comedian buddies into using it for the evening, along with female pronouns. I spent my first night as a girl. It felt fantastic. And, considering that so much about me at that moment was fake — my nails, my eyelashes, my tits — it felt completely natural.

It was also a scary time because as soon as I figured out what I was — a transgender woman — I knew how difficult the path ahead would be: embarrassment, social alienation, dozens of medical and therapy appointments, hormones, surgery. But before all that, I’d have to go back to my family and take back my lie.

“Remember when I said women’s clothes just fit me better? Well, that was way more true than I thought.”

Illustration by Elizabeth Simins