Halloween is the one glorious night where you are not only free, but encouraged, to embrace that which brings fear and loathing into the hearts and minds of common man. A cross-dressing man fits into that category as snugly as, say, Freddie Kruger or H.R. Giger’s Alien. But sometimes you gotta do what you gotta do.

Gathering a Halloween costume of any kind while sailing the Mediterranean is no small task, but even more so on the Wind Surf. Though the world’s largest sailing ship, she was still small enough to fit into as many old world ports as you can imagine. Thus we were in port seven days a week, frequently in seven different nations. Cobbling together a unified costume from bits and pieces obtained in Morocco, Spain, France, Monaco, Malta, Tunisia, Italy, Croatia, and Greece is not easy—especially when none of those countries celebrate the American holiday. Regardless, a Halloween crew party was announced, and nothing brings a shiver down my spine more than the thought of missing a crew party.

But what to be, and how? There were no superstores loaded with costumes, nor seasonal businesses in strip malls. Solutions always present themselves, however, and in my case it was in the form of… well, getting into women’s pants. While I admit to constantly thinking about getting into women’s pants, that rarely means actually donning them. But this is just what was suggested one evening when brainstorming with a friend from the spa.

“I have nothing to wear,” I lamented to Natalie, echoing women everywhere and from all times. Natalie noted this. “You sound just like my cabin mate,” she said. “Claudia whined about not having a dress for formal night, so I offered her one of mine.” I laughed, while she chortled in her wine. Natalie was six foot two inches tall, a full foot taller than Claudia. “You would fit better into one of my dresses,” Natalie continued. An idea was born.

So I borrowed a slim black dress from the Australian giantess and next port, Toulon, France, I found a wig shop. I opted for dirty blonde. Shoes were hopeless for my size twelve and a half feet (we weren’t in Vegas, after all), but accessories were hurled upon me by the entire spa staff. After great deliberation by the spa girls doing my makeover, I was ordered to shave my goatee. I complied. Then came the order to shave my chest. I did not. Soon enough, however, I was all dolled up and ready for the Halloween party on Wind Surf.

When I arrived to the party arm in arm with Natalie, everything came to a screeching halt. Literally: the Italian DJ actually fumbled with his music, horrified. Italian men would rather be hurled into the bowels of Hell than be seen without their machismo. The Asian crew stared, agog, while the usually uptight Brits gave me surprisingly ‘understanding’ nods.

Because the Surf was so small, the party only involved a few dozen crew members. Most costumes were improvised. Natalie wrapped herself toga-like in a white sheet and played goddess. Several spa girls borrowed boiler suits and with the help of lacy bras became… well… slutty, grease-smeared engineers. They were very popular, as one could imagine. The Canadian dive instructor grabbed a gondolier outfit in Venice, while the Indonesian (and flamboyantly gay) photographer just pranced around in his underwear. Oh, he also wore skull makeup. By the end of the night, most people were following suit. It was quite a party, as crew parties always are.

By Brian David Bruns, author of national best-seller Cruise Confidential.

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