I used to absolutely love Halloween. What a concept. Dressing up in silly outfits, pounding on doors, running across lawns and receiving yummy candy for free.

 

For free!

 

When I was growing up, candy came at a premium. If we kids wanted candy from mom and dad, we either had to save up our own money or do a specific chore to get our favorite candy cigarettes, Slo-Poke or Razzles.

 

At Halloween in the ‘70s, we kids would dress up as bums, football players and ghosts with materials and clothes we already owned. There was no shopping at Walmarts to pick out costumes in my day — we had to improvise with what we had around the house.

 

Even our bags to hold the candy had to be something we found around the house. We generally used pillowcases each year and sometimes resorted to paper grocery bags to take possession of our favorite treats.

 

After donning our homemade costumes and slinging our pillowcases over our shoulders, we propelled out the door as soon as it started getting dark. We never hit the streets when the sun was still out — but that’s the new world we happen to live in. 

 

I remember one year when I was around 13 years old, I wanted to “wow” my friends with a costume so unique, they would be jealous and would tell all our friends what a great costume I had. My older sister, Valerie, made a suggestion that I dress as a woman and at that moment, I thought “what a great idea.”

 

Big mistake.

 

As I watched my sister  in the mirror applying makeup to my face and clipping a wig to my head, I started to think this was a bad idea. I laughed out loud as she had me dress in a slinky dress, then I felt my body start shaking when she stuffed rolled up socks down the front to give me breasts.

 

Finally, when I donned the high heel shoes, I thought to myself, “How is this gonna work? How am I going to walk around the neighborhoods in this ridiculous outfit and footwear?

 

I got a yell from another sister down the hall who said my friends had arrived and were waiting for me to hit the streets.

 

I was scared. Halloween that year had really put the fright in me.

 

Sure enough, when I walked around the corner to my friends waiting by the door, there I stood in front of them in my best Marilyn Monroe look — and it took them a few seconds before they realized it was me dressed up as a girl.

 

The ensuing raucous laughter and surprised looks crushed my spirit to the core as I felt like crawling in a hole to escape the overwhelming embarrassment.

 

I wonder if Bruce Jenner had the same feeling when he first put on a dress?

 

And wouldn’t you know? I chickened out. 

 

Immediately, I ran from the room kicking the heels off and yelling at my sister for making me look so foolish (though I know it wasn’t her fault).

 

I relinquished the socks, peeled out of the dress and yanked the wig off. I scrubbed the makeup from my face enough to rub some burned cork on my jawline and below my nose for facial hair. Within minutes, I was dressed in ragged jeans and a holey shirt and joined my friends in the living room dressed as a hobo.

 

But the damage was done. I had, indeed, “wowed” my friends and they did in fact end up talking about my costume — just not in the way I had wanted it.

 

Halloween can be scary. Especially when a 13-year-old boy takes advice from his older sister, dresses in women’s clothing and lives to regret it.

 

Happy Halloween everybody!