How could I have known?

How could I have known what would happen?

I wasn’t expecting this – not even in my wildest dreams.

Hard and rough, not so tough, – new and trendy – now it’s Wendy.

An AP-500 story.


My auntie’s voice was calm. Remarkably calm in the circumstances.

She had come home from her Friday night out and found me lying asleep on the sofa. Not that unusual. But wearing a nightie. Not so common – not for a young man named Randall.

“Randall, dear, would you like to explain now – or in the morning?”

“Um, er, “…… silence.

“I guess you’d like to leave this to the morning. Will I be expecting you to breakfast in that nightie or do you have a negligee too, or perhaps a dressing-gown to suit. Mmmm?”

More silence.

“You’d better have made your mind up by breakfast time. I’m not that worried if you like to wear pretty clothes. I like to wear pretty clothes. But I’m not so keen on messing about and pretending half of the time one thing and then another. Goodnight, Randall dear.”

I had no idea that my aunt was so liberal in her attitudes. I really didn’t know her well. She had stepped in with an offer of looking after me for the summer and to Christmas while my parents took an academic sabbatical in Europe.

But – wow – she didn’t blow a gasket at me wearing a nightie. Wow. What sort of future could I look forward to? I fell asleep wondering.

I dreamt of all the pretty things I could wear – if I wasn’t just over six foot tall and quite broad at the shoulder.

I woke.

I heard Auntie downstairs and knew I must hurry to breakfast. I hesitated. I dithered. I decided.

“That is quite a pretty nightie, dear. When and where did you get it?”

By now I had also decided to be up-front and open. “I bought it last week.”

“Really. Was it an effort to go into Marks, I recognise the style, or was it easy?”

“If you go in looking as if you know what you’re doing, it’s just another sale.”

“Mmmm.” There was a pause. “Be careful with the honey, if it drips you’ll have to deal ..”

Too late.

“Well, just look at that. Quick, sponge it off or run and get changed. Have you anything to wear instead? And I mean as a girl, unless you want to go back to wearing boy clothes.”

I wasn’t sure I was hearing right. “D’you mean that Auntie?”

“Randall – clearly not y’name when you’re dressed – yes dear. I mean it. If you want to dress up then I won’t be upset. I will ask questions as to intention. Short-term and longer-term. It’s obvious you’re not doing ‘drag’ so it’s more on the cross-dressing or transgender spectrum. Yes?”

“Now, scoot off and get changed. Do you have anything pretty to wear? And I want to know your real name.”

I had very little to wear that was even adequate. I did my best with one of my two skirts and a badly-fitting blouse. Panties and cami but no bra.

“Well, well. We have a lot to do! Don't we ………?"

“.... Wendy.”

This is a 500 word story (basic text) and available for anyone who wants to take it further. AP



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This story is 570 words long.