He was Richard Sterling, the Indiana Jones of Gastronomy. The Fearless Diner. A travel writer and editor near twice my age of 24. Richard was a storyteller who liked the sound of his own voice, whose best stories involved his daring global escapades in grub, drink, love and war.

"Take me," I announced. "I've always wanted to hop a freight train." Truth.

"They don't let women in the yard," Richard warned.

"I'll dress as a man." I wiped off my lipstick.

"They'll roll you if they find out," he declared, showing his command of the hobo vernacular.

"All the better for my story," I argued, uncrossing my legs and planting my hands on my hips.

"If we run into bulls, it could get dicey."

"When can we leave?" I said, putting the discussion to rest. I could leave my job as a nanny for about three days. "Wait, what's a bull?"

A month later I woke up on the floor, one of several bodies in the aftermath of a house party. My lover's hand caressed my upper thigh and began its way down the length of my leg. I jerked my body from him just as he reached the soft forest I had cultivated on my calf.

"What's this?" he asked knowing full well that I was no hippie.

I stopped shaving to make my disguise as a man more authentic.

"Your what?"

"I'm going to hop a freight train. The guy who's taking me said they frown upon women in the hobo jungles," I explained, matter of factly, as if describing how to operate a washing machine.

"Boxcar Leo!" my lover announced. The room burst into uproarious laughter.

"Richard is going to call me Steve."

One week and two trips to Goodwill later, I met Richard at Oakland's piggyback tracks. We had agreed to come at dusk in our worst clothing. I had spent hours concocting my outfit. This was the real deal, no phony Halloween garb. Erasing all traces of femininity, I taped my breasts, donned scuffed men's workboots, torn corduroy trousers, a faded navy blue sweatshirt and a wool ski cap. An empty 10-pound coffee can and patched up pillow hung by rope from the bottom of my pack.

Richard arrived dressed as if he were going to an alumni football game. He wore khaki pants, a Pendleton overcoat and a spotless Cal Berkeley hat. I berated him for not lowering himself to the occasion. He asked me if I'd brought the salmon.

Yes, I had. Suddenly, the fact that I was a woman no longer seemed an issue. If any of the other hoboes found out that we had packed a feast of salmon and champagne for brunch, we'd certainly get jumped.

Richard left me sitting on a utility box while he went looking for an open car. The idea was to get on the car while it was still, and wait for it to move later in the night. In his absence I thought through how I'd use the coffee can as my toilet. I just hoped I didn't have to go number two.

As the night grew darker and Richard hadn't returned, I wondered where the other hoboes were. We were open to going anywhere, but wanted to get picked up by a train headed northeast towards Roseville, a central hobo jungle outside of Sacramento.

"They thought I was their boss," chuckled Richard when he got back. "I walked up to the men working on the tracks. They said they were going as fast as they could."

"See, I told you you didn't look like a hobo."

"They also showed me which tracks would be moving tonight. Let's go."

I followed him a few hundred yards. The tracks were like a 10-lane highway of parked steel and rust: brown cars, black cars, most covered with graffiti, and cars with no walls, just the flat bed. We picked one of two open boxcars and looked north up the tracks, confident that we would be moving in no time. The yard was quiet but sure to pick up activity.

Richard told me that the open boxcars get mighty dusty and to put on my bandana, thief style. It would protect me from breathing in too much dirt. I dutifully obeyed.

Then he reached into his pack and got out the gin and tonic. We toasted to Lady Luck and threw a few back.

"Steve, wake up!" Richard jostled me. "It's 8:30. You should see yourself. You're covered in filth."

He laughed. I sat up and got my bearings. My ass hurt and the bandana was still on. I was covered in a film of dust from head to toe. I stood and shook it off like a wet dog airdries. The King of the Road was sparkling clean.

"Where are we?" I asked.

"Oakland," Richard fumed. "The car didn't move all night. I'm surprised you could sleep. Trains were whizzing by."

I left my coffee can in the car and hopped out for a pee. Since the car wasn't moving, it was just as easy to pull down my pants and do it while leaning against the hitch in back.

We climbed onto the open car across from us and started to play cards. Four hours later we were bored with talk, waiting and the hobo life. The car still hadn't moved. The only thing that could lift our spirits was brunch. Richard popped the cork on the champagne while I covered our baguettes with cream cheese and pink Alaskan fillets.

In going through my bag I found the cell phone that my girlfriend had insisted I take for an emergency. Richard wanted to call some culinary friends and tell them what we were eating and where we were. Just as he started to dial, there was a huge jolt to our car. We grabbed our drinks before our car was hit with another crash and started to move.

"Woohoo!" we yelped and slapped a high five.

Now we were getting somewhere. Richard stuck his head out the car as the train slowly crept north. A hundred feet up the track a rail worker manned a post. Richard waved at him in a salute of success. The worker waved back. There was another jolt and we were thrown back. The car stopped moving.

"They decoupled us," Richard said deflated.

"They what?"

"They hooked up the cars they needed and took off without us."

We'd been on the tracks for nineteen hours, and hadn't traveled but a few hundred feet, not miles. The sun was high in the sky and I'd already taken off half my disguise.

"Should we call for a ride?" I asked.

"Nah, there's a bar within walking distance. Let's get a drink."

"Yeah," I agreed, a stiff one sounded about right. On the way I could call my bosses and assure them their nanny hadn't been rolled.

About the Author
Jennifer L. Leo is the editor of Sand in My Bra and Other Misadventures: Funny Women Write from the Road. She is also the author of WrittenRoad.com , an online resource for travel writers. This story is excerpted from the book, Hyenas Laughed at Me and Now I Know Why. Richard was the first person to invite Leo to dinner parties that included travel guidebook writers and magazine publishers. He still calls her Steve.

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