WHAT SHALL I BE? A HALLOWEEN STORY

SEAN, thirteen, already six feet tall, 165 pounds and still growing. He didn’t look much like an 8th grader in middle school. His less mature friends were already asking him to buy beer at the corner liquor store. When it turned October 1, Sean was already thinking about costumes. That Thursday afternoon, he arrived home form school asking,

“Mom, could you take me to Buffalo Exchange to look for a Halloween costume?”

“What are you thinking about for a costume this year,” I asked?

“I’m going to be a hooker!” Sean announced emphatically.

Oh well, I thought to myself. It won’t be much use arguing with this thirteen year-old man-child. So we headed for Buffalo Exchange climbing the stairs to a large space over looking Telegraph Avenue just down the street from UC Berkeley.

Sean spotted baskets of wigs immediately. He strode over and snatched a long, hairy blonde wig, its curls pouring over the basket’s wicker edge. Then he pulled it over his own short blonde curls.

“Looks convincing,” I said. But he wasn’t listening. He had already started pawing through a rack of black dresses. Finally, he extracted a sequined sheaf iwht a deep V neck. The material looked flexible as he struggled to pull it over his t-shirt and jeans.

“Now, I need some stiletto heels,” he asserted.

There were boxes and boxes of shoes scattered across the shop floor beneath the clothing racks.

“I need about a size 12 and a half,” he exclaimed.

Good luck, I thought. Maybe a cross-dresser left his size 12 1/2 stilettos from last year.

Sean wasn’t having luck finding the heels to complete the outfit. Finally, he approached the sales desk asking the cashier where he could find a pair of black stiletto heels size 12 and 1/2?

“You’ll have to go to the Castro in San Francisco for that,” the clerk replied curtly.

Without hesitation, I assured Sean that I wasn’t taking him to the Castro to look for stiletto heels and promptly paid for the wit and dress.

On Halloween day, Sean worn his hooker costume to school, minus the stiletto heels. Instead he wore a pair of black laced up hiking boots. Heavy boots and dresses were already a thing girls were using back in those days.

I was curious what kind of reaction he’d get at school, but I knew better than to say anything as he left for school that morning. When he arrived home in the afternoon, he was;ked into my office announcing,

“Guess what Mom? “

“What?”

“I won first prize for the best costume!”

I didn’t ask whether or not he’d told everyone that he was impersonating a hooker. I knew that there were enough LBGT faculty at the school who would probably approve of cross dressed costumes. Maybe they swayed the voting? Or maybe the judges had the teenage sense of humor?

Since that time, Sean has dressed in many costumes, not just for Halloween. He’s not a cross dresser, however, Just out there and confident in his choices. He wore a beautiful pink suit when he and Kate married 25 years later.

Playing dress-up at Halloween is a thrill we should all indulge ourselves in. As a woman, I’ve never wanted to impersonate a hooker, but I decided to be a black cat for Halloween 2025. I’m hoping to trick or treat and score my used to be favorite candy bar, Three Musketeers. Do they even exist anymore? I intend to find out.