The Old Crossdresser – The Cornbury Society

By Stephanie Mitchell

Adapted with apologies (although not especially sincere ones) by Stephanie from A. A. Milne’s “The Old Sailor”
Illustrated by Stephanie Mitchell with help from ChatGPT.

here was a transvestite, my grandpa would swear
Who had so many clothes that he wanted to wear
That whenever he wanted to dress and go dancin’
He couldn’t because of the state he was in

He was single, and lived in an apartment for weeks
Wearing feminine clothing he’d purchased from freaks
In the circus, till one day he finally decided
That it was certainly high time that he ventured outside. He’d

Have to get shoes, and he wanted a gown
(Which he’d seen years before in a store way downtown).
But he thought it would look out of place without furs,
So he’d need lots of money, so he needed a purse.

Then he looked at his pretzels-and-beer-style physique
But to shape it to feminine form would take weeks.
And even with his fitness club membership card
He couldn’t go in there without a leotard.

So he started a list on some paper he’d found:
”I must first buy a bra!” and then “Two breast forms (round).”
“A girdle, a wig, and then (just for a lark)
Some lacy pink undies that glow in the dark!”

He had just read a letter from his girlfriend in Dorset
Who would sell (for a fair price) her grandmother’s corset.
He travelled all morning to go pick up this treasure
When he stopped, and decided, “But first I must measure!”

He rushed home and studied and counted and noted
The size and positions of waistline and bloated
Projections. Then he spied through his window some electrical pylons,
Which reminded him (because of the rhyme) to buy nylons.

“

But nylons show leg hair, which means waxing or shaving.
I’m kinky, but pain isn’t one of my cravings.”
And shaving means beards, which means makeup like plaster,
And I’ll never get out if I don’t do this faster.”

So he thought of his gown, and he thought of his furs,
And his pretzels-and-beer-style physique, and his purse
And the nylons (for leg hair) and makeup (for looks)
And the wonderful tricks that you read of in books;

But the saddest and sorriest part of this story
Is that he DID finally get all dressed up in his glory.
But all of his neighbours met to chat in the hall —
And my grandpa’s CD friend couldn’t go out at all!