Sunday, September 21, 2025

Halloween 2008

I don't think I ever wrote about this night for my blog.  So, I wrote this for my book, Men of the Skull, and, well, here it is. 

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            It’s an ancient cliché that the smallest events, even a single word, can change a life. In this case, an off-hand suggestion over dinner.

 

Interlude 4: Forty-Two (Halloween 2008)

Friday, October 24th, 2008 World Series tickets a hot commodity

The past year had been very hard— what with a newborn and all.  For my wife’s fortieth birthday, she wanted a weekend at Bethany Beach, Delaware, at the Addy Sea, a beautiful, haunted bed and breakfast.  We left our daughter—with her first birthday just days away—with my parents, who’d retired nearby.

That night, we went south a few miles to Ocean City, Maryland, for dinner at the Blue Ox.  With Halloween just days away, the subject turned to costumes.  We both loved Halloween and often did couples’ costumes.  But “we went as Lois and Clark last year,” I mentioned.  As in Lois Lane and Clark Kent. 

“Yes,” she said, “but this year, you’re Lois.”

At that moment, our meal arrived, and the server refilled our wine glasses, which ended the discussion for the moment.

Me as Lois?  I hadn’t dressed as a woman in twenty-five years.  I had shut down and sealed off that “freakish” side of my life.  Should I do it again?  Could I?  I was now much taller and heavier—testosterone poisoning does that, as does age.

 

What was I thinking?  Twenty-five years… no problem.  One night in a skirt and out.  No biggie.

After all, I was a MAN.

 

Friday, October 31st, 2008.  Parade for the Champs

Halloween

It had been a busy work week.  I asked a bookstore co-worker, Elizabeth, to help.  She showed me a memoir by a famous drag queen called I Am Not Myself These Days.  Brilliant book.  I figured she wouldn’t be weirded out by my request.  She wasn’t.

In fact, Elizabeth was very enthusiastic—too enthusiastic.  She helped me choose an outfit at a store specializing in plus sizes.  I found a wig and shoes online.  The memoir suggested using birdseed in cut pantyhose to fill the purple and black lace bra (it was on sale- 42 D).  An old friend who worked at a salon said she’d do my makeup.  Oh, and she invited us both to her Halloween party.  So, we had someplace to go—but we’d have to bring the baby.

 

No problem.

 

Everything was ready.  What could go wrong?

 

Halloween night.  I showered, shaved my legs, and after a quick nap dressed up in the girl stuff in the bathroom.  With me, I had the Superman T-shirt my wife would need.  She already wore glasses, as do I.  But that night I wore contacts.

On a whim, I brought my digital camera into the bathroom. I figured I’d take a picture of her reaction upon seeing me.  I came out of the bathroom armed with a camera in one hand and a Superman T-shirt in the other.  I adjusted the camera, my hand bouncing off the birdseed breast as I did.  She was in the kitchen, maybe thirty feet away.  She turned and saw me.

CLICK.

The look on her face was utter disgust- a stark contrast to her smiling jack o’lantern t-shirt.  I stumbled over in heels and tossed her the t-shirt.  “I’m ready.  Your turn.”

She looked confused, still disgusted.  She had forgotten all about her idea and thought we were staying home with our baby daughter.  So, I explained her idea back to her—and that our friend would do my makeup at the party.  She reluctantly agreed.

Fast forward: the party, me going into the bookstore where no one recognized me (except Elizabeth) which set me a bit at ease, a bunch of us later at a local sports bar where one of my female co-workers grabbed my fake boobs, curious how they felt.  Lots of people in the bar laughed. 

At the book store

Laughing while wearing a constricting bra and waist cincher was a new experience.  Also, I got some looks when I went to the men’s room.

Driving home, I realized that I had a wonderful time that night.

But something felt… different.  Strange.

I looked down at my sweater covered, birdseed breasts and realized what it was.

I felt at peace. 

The anger and depression I’d carried for decades was gone.  Missing.

I knew then that I had made a major mistake.  I was in big trouble.  The metaphorical wall I had built to contain my feminine self, the one that had held strong and firm for twenty-five years, had been breached.

 

I felt right.

 

God help me.

 

 

 

I still have that purple bra, and even wear it occasionally, despite it being a cup size too small.  Now it’s me, not birdseed, filling out the cups.  Funny how things change.