How to cross dress

The only person who knows about my cross-dressing is Oscar. We’re both volunteers with a local political party that aims to improve the quality of life in Kitanye. Oscar instinctively knew my secret. One day he winked and smiled and offered me a pair of off-white trainers with rose-gold toecaps. “Here. These might look good on you.”

I told him about my catastrophic excursion to the Big Market and he invited me to his apartment in down-town Chanzo to talk about  some tips.

“Come on.  We’ll grab a taxi!”

Oscar’s apartment flouts description! It’s a jumble of mirrors, bright lights, carelessly tossed finery, frippery and feather boas. A dresser and mirror, adorned with at least a thousand bottles and jars of perfume, nail polish, varnish remover, oils, creams and skin-tone whitener.

My eyes were everywhere. This is what I want, I thought. And soon I’m gazing into a full length mirror, looking beautiful in a dress. A very, very, red dress. Crimson.

Oscar non-stop talking, “You see how it sets off your shimmering skin and the halter-neck draws attention to the beautifully distinct shoulders you have and the high waist band means when you twirl the material spirals around you a full second later.”

Then two short sharp bursts of spray. “And that my darling is Jean Patou – at 500 guineas an ounce.”

‘What’s a guinea?’ I thought.

“Let me just put this on.”  A short, chestnut, bob-wig. Chic. Classy. Wow! “And we could try these. Let me just be a little intimate while I slip them in.”

I looked at the two frightening, alien substances Oscar produced from his dresser.

chickenfillets“Now normally you should attach them to a bra but as it’s a halter-neck we could just slip them in. They’ll stick to your skin.” Two gummy, rubbery, skin-coloured tumours pushed against my quaking chest. “Don’t worry, darling, they’re only silicone, and they hold up rather nicely don’t they? Chicken fillets we call them. Give you more shape!”

My eyes were everywhere. But especially the mirror.

“Or we could try this!” Oscar snatches the chestnut wig and substitutes a ridiculously electric blonde shocker.


“Learning the art of dressing as a woman,” said Oscar “can make life much easier for a cross-dresser. There are some simple rules:

Avoid high heels, especially with sling-backs, until you have mastered walking in women’s footwear.

Avoid glittery cocktail dresses until you have practised moving, standing and sitting as a woman.

Try to shop in a place that is liberal and accepting of different lifestyles. Clearly, if you live in a small town, you will rouse comment if you shop for yourself in the local women’s shoe or dress shop.”

Oscar winked and smiled. “Come on”, he said “I’ll show you how to put on lipstick.”


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