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Chapter 2

It was five years into my trucking career when I made the biggest mistake of my life. I was making a run down the I-70 in Utah, hoping to make it to Grand Junction before nightfall. I should have filled up in Aurora, but there were over fifteen trucks waiting in line for gas, and I wasn’t in the mood for waiting. For some reason, I thought I’d be able to make it. In case you don’t know, there’s no place to fill up between Aurora and Grand Junction, and that’s almost one-hundred and fifty miles. Hell, I might have made it had my tires not been a bit low on air.

But I didn’t make it. I was about sixty miles short when the gas light came on, and I was about forty short when the gas pedal stopped working. I was stranded in the middle of nowhere.

My second biggest mistake was leaving my truck. I should have spent the night and tried to hail down a fellow trucker in the morning. But I didn’t do that—I decided to try and hike the forty miles. What a stupid decision that was… I walked all night, until my legs were screaming in pain. I had no idea how close I was. I had no phone service. My best guess was that I was still a good twenty miles away, which meant another day or so of hiking.

I could have gotten a ride had I waited at the truck. Truckers always help each other out. But my truck was twenty miles away. As far as any passing truckers were concerned, I was just another hitchhiker. And as the unwritten rule goes: only girls get a ride. That didn’t stop me from trying. I spent a good five hours trying to flag down a ride. No one stopped for me.

I was exhausted—so exhausted, I walked into the woods, found a soft patch of moss, and took a rather uncomfortable nap. When I woke up, it was dark. I overslept on that cold ground. Trying to find my way out of those woods, I ended up tripping over a root and twisting my ankle. Now I was really screwed. No one was going to stop to give me a ride and walking twenty miles on a twisted ankle was out of the question. My situation was beginning to look grim.

I don’t know why I bothered, but I ended up back on the street, trying to flag down a ride. Of course it got me nowhere, but I was desperate for anything. I was hungry, thirsty, sore, and tired. I would have killed to spend the night in a motel.

I managed to make it another five miles before the pain in my ankle became too much to handle. And as fate would have it, I came across a turnoff next to a sign that read: Private Property, No Trespassing. Hoping to find someone who could help me out, I walked down the turnoff—a mile-long dirt road that led to an old house. I knocked on the door. “Hello! Anyone home?” I called out, but the house was dark and no one answered. I continued knocking for a good ten minutes before I decided to break in. I didn’t see any other choice. I needed to find a phone. I needed a drink of water and a morsel of food.

Unfortunately, there was no running water in the house, which I learned was long-abandoned. The fridge was totally empty, probably ransacked years before by passing squatters. I did find a water bottle in the basement and a can of beans in the very back of the kitchen pantry. The bed in the house was far from comfortable, but it beat the hell out of the forest floor. I fell asleep within seconds of laying down.

My ankle was badly swollen when I woke up. I could hardly walk. But with nothing left to eat or drink, what other option did I have?

I knew I smelled awful, so I went to the closet hoping to find some clean clothes. Unfortunately, the closet was only filled with women’s clothes. I dug through the clothing options, hoping to at least find a shirt that could pass as a man’s shirt. I found a white blouse that looked a bit like a dress shirt. As I held it up to my body, I had a crazy idea.

I must have stood in front of that dusty, old mirror for twenty minutes as I considered the idea—to dress up as a woman to get a ride to Grand Junction. If I did it, would I have to suck a guy off? I’d given girls rides before without expecting any sexual favours in return. It was only about fifteen or twenty miles, after all.

Even if I had to suck a guy off, was it really that big of a deal? If it was the difference between living and dying, what difference did it really make? The only other option was to hope someone would pick me up as a man, or that I could somehow hobble through my pain and make it all the way to Grand Junction—unlikely. As far as I knew, I was still fifty miles away. I really had no clue how far I was.

So was it really such a crazy idea?

I put on the blouse and it looked ridiculous hanging over my jeans. No, it didn’t look like a dress shirt at all. I dug around, looking for something better. There was nothing remotely masculine in the options. So I held up my old, dirty shirt—the one I’d slept in two nights in a row (including one on the forest floor), and hiked twenty miles in. And then I had that crazy idea again. What if I could pull it off? If I really could look like a woman, my conundrum would be nothing. I’d have a free ride from the next truck that went by.

I put on one of the bras that was hanging in the closet, stuffing it with a handful of socks to give the appearance of a bust. Then I put the blouse back on. It didn’t look quite as silly with the padded bra underneath, especially when I stood up straight. I continued to dig around and ended up finding a plaid skirt and a pair of white stockings. Using a razor and some shaving cream I found in the bathroom, I shaved my face and legs (which wasn’t so easy without running water). Unlike a lot of other truckers, I never had much in the way of facial and body hair, so it wasn’t hard to get my skin looking smooth and feminine.

I put on the skirt and the stockings. And then I stared at myself in the mirror, totally unsure of what I was seeing. I couldn’t tell if I looked great or if I looked ridiculous. I really looked like a woman, but I could still see myself, and I knew that I was really a man. But to someone who didn’t know me, what would they see? Would they see a man?

In one of the closets was an old Halloween wig. It looked kind of silly on my head. I ended up taking it off and giving it a good shake, creating a cloud of dust. After a good brushing, it looked passable.

I found a makeup kit in the bathroom and decided to see what I could do to push my guise a bit further. I used a good dab of concealer to evenly cover my face, so my skin would appear softer. I tried not to overdo it, so I wouldn’t look like one of those drag queens that flock to Dolly Parton concerts. It turns out, it’s a lot harder to get eyeliner on perfectly than it looks, and just one dab too many with the blush and you end up looking like a child’s doll.

I spent a good couple of hours making sure every little detail was perfect. My growling stomach finally let me know that enough was enough. I needed to get to town and eat something. I looked in the mirror again. I could still see me. But to a stranger, would I pass?

I had no other option. I put my wallet into an empty purse I found in the closet and I took off for the road. Even though there were no people around, I felt incredibly exposed and vulnerable, walking outside in a skirt and stockings, with a face of makeup. Maybe I really had lost my mind—maybe the lack of food and water had sent me into a sort of delirium. I would find out one way or another as soon as I came face to face with a trucker.

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