Thirty years. That's how long I've been buying, hiding, and purging. Three decades of secret orders, of clothes stuffed in the back of wardrobes, of shame that never quite went away no matter how many times I threw everything out.
This morning, I wore a skirt to a café.
Not a costume. Not a dare. Just a navy pinstripe pencil skirt, a white fitted t-shirt, my black bomber jacket, and the quiet certainty that I was done hiding.
The Logistics
Getting there required planning. I left home at 6am for the gym—normal routine, nothing to explain. In the changing room, I slipped into my bra, panties, and tights, then pulled size 16 jeggings over the top. Trainers. Bomber jacket. Nobody noticed. It was busy, everyone focused on their own thing.
In the car park, I made the switch: jeggings off, pencil skirt on. Trainers swapped for block heels. I stepped out, smoothed everything into place, and walked toward the café.
The Walk In
The Roade House is a small wellness café in a Northamptonshire village—yoga studio attached, plant-based menu, the kind of place where people mind their own business. A friend was already there, waiting. We'd planned to meet at 8:30.
I came in through the rear entrance—where the car park is, which puts you right by the counter and the baristas. The young woman behind the till looked surprised. I saw it register on her face. She didn't say anything.
My heart was racing.
My friend handled the order while I stood there, back to the counter, trying to figure out where to sit. It felt like forever. Probably a minute. We picked a table and sat down.
The Hour That Followed
The coffee came. The owner brought it over—he's seen us both there before, though never me like this. Same cheery self as always. If he noticed anything different, he didn't show it.
And then we just... talked. For an hour. About everything and nothing.
What surprised me was how quickly the anxiety became background noise. The things I'd visualised beforehand—knees together, smoothing the skirt at the back with one hand when sitting—they just happened. Natural. Like I'd been doing this forever.
By the time we left at 9:30, I'd almost forgotten what I was wearing. Almost.
The Sound of Heels
Two things caught me off guard.
First: the seatbelt. On the drive there, it crossed my chest differently—right down the middle, the way it does when there's something there. My 44A bra with my pecs underneath. It made me realise that even an A cup looks significant when everything's pulled together.
Second: my heels on the café floor. That sound. My friend walked behind me at one point and said afterwards that I'd absolutely nailed the walk. Everything just clicked.
I'm 6'3". In two-inch block heels, I'm 6'5". I'll never blend in. I'd been worried about that—thinking I could never justify wearing heels regularly, that anything higher would look ridiculous.
But maybe blending in isn't the point.
What I Learned
The world didn't end. A barista looked surprised and said nothing. An owner was friendly. People had coffee. I had coffee. That was it.
There's a particular kind of freedom in finally doing the thing you've been afraid of for decades. Not the absence of fear, but the presence of something stronger. Call it defiance. Call it authenticity. Call it being too tired to pretend anymore.
I'm not here to make a statement or start a movement. I'm just a guy who likes wearing skirts, who spent thirty years pretending he didn't, and who finally decided that life is too short for that kind of hiding.
The serene feeling didn't hit until I got home. But it's here now.
This is the first real entry in The Hourglass Project. Building the body. Wearing the clothes. Living the life.
More to come.