A cross-dressing revelation

It was about 11:30 p.m. on a Saturday night, the second night of Halloween weekend, when I came to a remarkable realization.

Walking a mile in one-inch heels is an excruciatingly painful experience, a modern rung in one of Dante’s circles of hell  reserved for females and those males courageous enough to attempt this endeavor.

However, I must place this in the correct context before I continue.

On that Saturday night, I found myself without a costume and without a clue about what I would wear to the various Halloween parties occurring around Tacoma. In my typical procrastinating fashion, I waited until the last minute to consider my costume options.

My first thought was that I should take a sheet and wear it as a toga, a simple enough costume to construct. Yet, as I was preparing to wear it, my roommate’s girlfriend jokingly suggested that I don her clothes instead.

Unfortunately, this joke was overheard by one of the other residents in my house, who saw this as the perfect opportunity to create the ultimate costume for me.

After much convincing and pleading, I willingly decided to cross-dress for Halloween. A year ago, I wouldn’t have even considered the idea, yet for some reason on that Saturday night, I thought it would be a memorable experience, not knowing whether I would view it favorably once the night had passed.

After an hour, the transformation was complete. My beard was shaved, make-up was applied, tights and a skirt were hiked up, and finally a blonde wig put on my head finished the costume.  The worst of it was the application of eyeliner, which I believe would have blinded me if not for sheer luck and willpower.

When I first saw the results of the transformation, I was shocked at how convincing the costume looked. For those who were involved in the process, they took pride in how well their efforts had been able to turn me from a rugged male hipster into a blonde woman.

However, the moment I realized my costume’s uncanny deceptiveness was when I approached two of my housemates who weren’t involved in the process or aware of the change and said hello to them. They cautiously replied, wondering to themselves who I was, until the moment of realization became apparent on their faces: a shared look of shock and incredible confusion.

Once all of us had prepared our costumes, my group of friends and I went out and walked across the outskirts of campus, encountering various people on the way.

These encounters varied from awkward to downright hilarious. I was hit on by several guys, some in a drunken stupor, who apparently believed I was a woman. Their reactions at the realization that I was not could be summed up in one statement:

“Hey, who is she? She looks pretty…That’s a guy. Holy Shit!”

Let’s use their body language to break down this statement. With every step a person took as they approached our group, the cloak of night and drunkenness would fade further away from their eyes as they came to realize that they had in fact checked out a man.

As I was walking home with two housemates of mine (who happened to be girls) after having been outside for a few hours—and my feet having endured a gut-wrenching amount of pain—I stopped on the sidewalk and declared:

“I don’t get it. I dressed like this just to have fun, and it feels like guys were undressing me with their eyes all night long. Is this what it feel likes all the time for you?”

They both stared at me for a moment.


I have since vowed never to creep on passing females and to appreciate the daily strife that accompanies fashionable women’s apparel.

My experience that night made me appreciate how hard it is to walk a mile in a woman’s shoes, especially if they are in heels.