A black escort date dress hangs on the bedroom door of an expensive New york apartment.
Choosing your first escorting dress is a huge milestone.

My little black dress: A story about my first escort outfit

Georgie Wolf
Georgie Wolf

I’ll always remember my first little black dress.

It’s a rite of passage – the first purchase one makes as a sex worker. Perhaps it’s not always black…depending on the worker, it could be a red dress, a sparkly sequinned affair, or a smart business frock. Perhaps it’s not even a dress. It could be a slim tie or a beautiful jacket. Ask any escort; we all have a story about our first work outfit.

When I started working as an escort, I didn’t have much cash to hand. I was recently arrived from Sydney, with no fixed address and a car whose back seat was littered in job applications. I wondered, how was I going to transform from this tired, discouraged wreck into someone glamorous and engaging?

The problem was complicated by the fact that I barely owned any dresses. I was very much a tomboy, and my work sitting behind a desk hadn’t prepared me; most of my wardrobe consisted of jeans, shirts and jackets. It seemed an unlikely transformation … from office flunky to femme fatale. Could I pull it off?

Days before my first job, I went on the hunt for an outfit that could make me look like an sex industry pro.

I wandered the corridors of the nearest suburban shopping centre. I couldn’t afford any of the high-end boutiques…in fact, I could barely afford any of the cheaper fashion options either. And the stuff I saw in the cheap stores just didn’t suit my style. I wanted something that would wow my clients, make them feel as though they were in the presence of someone worthy of both their time and the fee I was charging.

Desperate now, I paid a visit to my local thrift store....and it was incredible. There were entire aisles of dresses, of every cut and colour. Some items were designer-labelled, and some still had the tags attached, donated in as-new condition.

Rummaging through the racks, I was reminded of how fashionable the folks of Melbourne often are, compared to the town in Sydney that I’d just moved away from. I mean, if people were throwing away this sort of stuff, imagine what they must still have in their closets?

I was hopeful as I moved from one hanger to the next. But there was so much to look at! My fingers flicked past dress after dress, and with each one I passed over I became ever more fearful that I wouldn’t find exactly what I needed.

Eventually, my gaze settled on a slim black cocktail number with a beaded front. It had a lacy back, perfectly sexy. My first reaction: is that dress too short? My second: I want this. I crept into the change rooms, fumbling with the zip. It seemed impossible that it would ever fit me.

Yet as I stood in front of the mirror, examining my body from every possible direction, I was suddenly aware of a shift in my demeanour. I stood taller, with shoulders back. I was discovering – for the first time in my life – that the right dress can make me feel, not only attractive, but incredibly confident.

The feeling persisted even after I took it home, nestled carefully in a second-hand paper bag. And when I slipped into it the next day, and set out for my first assignment, I was buoyed by an overwhelming sense of rightness, as though this was something I’d been waiting to do all my life. My first booking was fantastic…and I believe I owe it, in part, to the sexy self-assurance of finding the perfect costume.

Eight years later, my financial situation is much healthier (and so is the rest of my life!) I do buy much of my work wardrobe new…but every now and then I’ll still wander the aisles of my local thrift store, hoping to glimpse something that suits me.

As any pro can tell you, the right dress makes all the difference.