A Shopping Expedition

My name is Brian and I live in a small town I shall call ‘Smallville’. Before the freedom of buying from internet shops and having parcels delivered anonymously to your front door, one had to go to a physical shop. This took immense courage, bravery, and determination.

Here is the story of a shopping expedition. It may be true, it may be in my imagination.

Chapter 1: The Drive to Townsville

The morning sun filtered through the thin curtains of my bedroom window, casting familiar shadows across the worn wooden floor. I’d been awake since half past five, lying still and listening to the town stirring – Mrs Pickering’s tabby yowling from three houses down, the distant hum of the milk float as old Jim made his rounds with clinking bottles, the gentle whoosh of wind through the old oak trees that lined our street.

At twenty-five, I knew every sound this town made, every rhythm of its days. I’d grown up here, gone to school here, and now worked at Pickering’s hardware shop three streets from where I was born. It was the kind of place where everyone knew everyone, where your business became the town’s business over tea in Molly’s café, and where a secret could travel from the post office to the church steps in under an hour.

Which was exactly why, on this particular Saturday morning, I was planning to drive the thirty miles to Townsville.

I sat up in bed, running my hands through my sandy brown hair, and glanced at the clock: 7.42. The shops in Townsville wouldn’t open until nine, but I needed the time to work up my courage. My stomach felt like it was housing a family of butterflies, all of them doing aerial stunts.

“Just do it,” I told myself, the same words I’d been repeating for weeks. “Drive over there, walk in, look around, and see what happens.”

But it wasn’t that simple, was it? Nothing about this felt simple.

I stood and walked to my chest of drawers, catching my reflection in the mirror above it. Average height, lean build from years of lifting boxes and timber at the hardware shop. Brown eyes that my mother used to call “kind eyes.” She’d been gone three years now. I looked ordinary, unremarkable, the kind of person who could blend into a crowd, which was both a blessing and a curse in a town like Smallville.

I dressed carefully in my usual Saturday clothes: well-worn jeans, a flannel shirt, and an old leather jacket. Everything about my appearance said “ordinary bloke running errands,” which was exactly what I needed. But my hands shook slightly as I buttoned my shirt.

The desire had started small, barely a whisper at the back of my mind many years ago. I’d notice things: the way fabric moved, the lines of a dress in a shop window, the swish of a skirt as someone walked by. At first, I’d pushed the thoughts away, told myself it was just curiosity, the way anyone might notice a handsome car or an interesting building.

But the whispers had grown louder as I got older.

I’d started paying attention to women’s fashion in ways I never had before. When I watched television, my eyes would drift to the actresses’ clothes. At Pickering’s, I’d find myself studying the few women customers who came in, admiring the way a blouse draped or how confident someone looked in a flowing skirt.

Two months ago, I’d driven to Townsville for a ‘legitimate’ reason, to pick up a part that Pickering’s couldn’t get. Walking along the High Street, I’d stopped in front of ‘Beatrice’s Ladies Fashions’. The window display featured a navy pleated skirt paired with a cream-coloured jumper, and something about the combination caught my breath. I’d stood there for minutes, pretending to read the notices in the newsagent’s window next door while stealing glances at the outfit.

Since then, I’d made excuses to drive to Townsville three more times, always walking past Beatrice’s, always slowing down to look, never quite brave enough to go inside.

Until today.

I made coffee in my small kitchen, the familiar ritual calming my nerves a little. My parents had bought this house in 1974, and I had inherited it along with all the memories in its walls. Usually the familiarity was comforting, but this morning it felt constraining, as if the walls were pressing in on me.

I’d been searching for answers for a long time. Through whispered conversations and stolen glances at magazine stands, I’d discovered I wasn’t alone – that there were others who felt this same pull. I’d heard the names, crossdresser, transvestite, even transsexual, whispered in hushed tones or mentioned briefly in medical books at the library. Others simply called it being themselves.

I wasn’t sure what to call it. All I knew was that the feeling never went away, and the only thing that seemed to help was imagining myself in that shop, touching those fabrics, maybe even trying something on.

I sat at the kitchen table with my mug, looking out at the garden my mother had planted. The roses were blooming, their pink petals soft in the morning light. She would have understood, I thought. She’d always been the one who encouraged me to be honest about my feelings, to “follow your heart,” as she used to say.

My father, God rest his soul, might have struggled more. He had been a good man, but traditional, the kind who believed in clearly defined roles. Still, I liked to think love would have won out in the end. My parents had raised me to be kind, to treat others with respect, to harm no one. Surely that extended to being kind to myself too?

By half past eight I couldn’t sit still any longer. I washed my mug, grabbed my keys and wallet, and headed for the car. The drive to Townsville usually took about forty minutes, but I’d planned to take it slowly today and give myself time to think.

The morning was crisp and clear, the kind of late summer day that made you grateful to be alive. I wound down the windows and let the fresh air rush through the car. The familiar route unwound before me: past Malcolm’s farm with its barns and scattered cattle, through the stretch of woods where my father had taught me to name the trees, over the little bridge across the stream.

As Smallville disappeared in my rear-view mirror, I felt some of the tension ease. With each mile, I was becoming more anonymous, less known. In Townsville I was just another face in the crowd. The thought was both liberating and terrifying.

“What if someone sees me?” The worry crept in despite my best efforts. “What if word gets back to Smallville somehow?”

But then another voice answered, one that sounded surprisingly like my mother: “What if it doesn’t? What if everything goes fine? What if you find something that makes you happy?”

The outskirts of Townsville began to appear: huddled suburban houses, the out-of-town shopping centre, all the signs of a bigger place with more opportunities and more anonymity. My heart rate picked up again as I followed the route I’d memorised to Beatrice’s.

I parked a few streets away, outside a coffee shop, and sat in the car for a full five minutes watching people walk by. Ordinary people, going about their ordinary lives, none of them knowing about the storm I was weathering.

“You can do this,” I told myself. “You’ve driven all this way. You don’t have to buy anything. You don’t have to try anything on. You can just look around and leave. Baby steps.”

I locked the car and started walking, hands tucked deep in my jacket pockets, my heart beating so hard I was sure everyone could hear it. The streets were busy enough that I felt pleasantly anonymous.

From the corner I could see the shop’s cheerful yellow awning and, beneath it, the familiar window display. The navy skirt was still there, still paired with that cream jumper, still making my pulse quicken. But today, instead of walking past, I was going to walk straight through that door.

For the first time in months, I allowed myself to imagine what might happen next. Maybe the assistant would be kind. Maybe I’d find the courage to ask questions, to touch the fabrics, to explore this part of myself that had been whispering for so long.

Maybe, just maybe, this would be the day I started listening.

I took a deep breath, squared my shoulders, and kept walking.