Fruit of the Loon: Confessions of an Accidental Cross-Dresser

An empty underwear drawer made me into the man I am today

Photograph by Getty Images

I address the following to my fellow American males who wear underwear each day — boxers, briefs, whatever. Those who do not are, of course, more than welcome to continue reading, although I don’t imagine this tale will fully resonate with you.

In the mid-'70s through the early '80s, I was pretty much stuck in post-adolescence, lurching uncomfortably from moment to moment, trying to sort out myriad love, family, career and money issues. I happened, probably not by chance, to marry someone who was even less far along on this troubled journey than I. The impact of such a marital union, in purely practical terms, was that certain essential elements, like housekeeping, cooking and laundry, tended to get pushed to the backburner. Far to the backburner.

And so it was that on one weekday morning circa 1980, I awoke to find my underwear drawer empty. Half-panicked, I rummaged through the shorts and T-shirt drawer, and found nothing there, either. In my pre-caffeinated mental state, I could envision but three viable options (crawling back into bed or doing a fresh load of laundry were out of the question, as I had multiple deadlines and meetings scheduled throughout the day).

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Option One: Reach into the hamper for yesterday’s pair (not in this lifetime).

Option Two: Go commando. Too icky. I rode a packed rush-hour subway train to work each morning. Enough said.

Option Three, the one I ultimately chose: Borrow a pair of my wife’s panties.

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Not being Dennis Rodman, I must admit that this creeped me out just a little, too. But it was the kind of creepy I figured I could live with for 12 hours.

And, indeed, upon donning female apparel for the first time since my baby sister and I played dress-up in my mother’s wardrobe closet, I completely forgot what I was wearing beneath my corduroys.

That is, until lunchtime, when I crossed the street from my office to the gym for a quick workout. It took the raucous laughter of a locker room full of manly men to remind me I was wearing panties. More precisely, pink panties. Sure, it was embarrassing, but not embarrassing enough to cause me not to see the humor in the situation. Besides, it wasn’t like I now had to go back and reexamine my core sexual identity. I’d read the literature in Abnormal Psych 101 and knew that transvestites and cross-dressers derive sexual pleasure from wearing clothes from the opposite sex. Me, I was just trying to stay clean for a day and give the other subway riders a break.

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I hadn’t thought much about my little adventure on the feminine side until a few weeks ago when my wife — not the one from whom I purloined the panties — and I were dining out with friends. Something that was said at the dinner table must have jogged my memory, and I related the above story.

The three other men in our party — none of them a Neanderthal — appeared positively aghast and, to a man, stated that they would rather forego underwear for a week, or a month, before they’d stoop to wearing their wives’ intimate attire. I was somewhat taken aback by their vehemence, given how far our society has come in the last 35 years. Unisex nail salons, metrosexuals, female fighter pilots, Mrs. Doubtfire.

I thought it was time to look into whether, even in a relatively progressive social circle like my own, dressing in your wife’s panties — in exigent circumstances or otherwise — is still considered outside the bounds of propriety. My brief survey pointed to a conclusion that, in retrospect, seems quite obvious: one’s friends and acquaintances are much more willing to accept non-traditional behavior in society at large than they are among those close to them.

And that’s OK, I guess. Anyway, I’ve moved on. Today, virtually the only thing I never procrastinate about is my laundry. And now, if you’ll excuse me, there’s a washer/dryer in the basement with my name on it.

Tags: memoirs