April 23, 2025

Author: Oliver Marsh

Hiking has always been my escape. There’s something calming about being out in nature, walking for hours without a care in the world. But I don’t just hike for the scenery—I hike to be myself in a way I can’t in the everyday hustle. I’ve always enjoyed crossdressing, and hiking on obscure, off-the-beaten-path trails has become my way of embracing that side of me. There’s something liberating about it, the freedom of being out in the woods, surrounded by trees, with no one around to judge.

I rarely run into anyone, and even when I do, the trails are so remote that it’s easy to just slip away and go unnoticed. I’ve always been careful, choosing routes that aren’t well-known or heavily trafficked. The secrecy has become a part of the experience—each step, each moment, is for me alone.

Last week, I took a trail I hadn’t tried before. The day was warm, the sun was just starting to dip behind the trees, and everything felt peaceful. I’d been walking for a while, my mind wandering to different thoughts, when I heard the sound of footsteps behind me. My heart skipped a beat. It’s one thing to hike in isolation, but hearing someone approach you when you’re dressed the way I was… it was unsettling.

I turned quickly to see a park ranger making his way up the trail. I froze, unsure of how to react. It wasn’t like I was doing anything wrong—no one had ever said anything about my outfit before. But the feeling of being discovered, of being seen in this vulnerable state, suddenly felt overwhelming. I wasn’t sure what would happen next. Would he ask questions? Would he tell me to leave?

The ranger must’ve noticed my discomfort because he slowed down when he saw me standing there. “Hey, everything alright?” he called out, his tone friendly but cautious. There was a slight tilt in his head, as though he didn’t quite understand what he was seeing.

“Yeah, just out for a walk,” I replied, trying to sound calm. I gave a nervous smile, but I could tell from his gaze that he had already noticed what I was wearing.

“I wasn’t expecting to see anyone this far out,” he said, stepping a little closer. “But, hey, it’s a free world, right?”

There was a pause as I processed what he was saying. He wasn’t judging, wasn’t telling me to leave, but the situation still felt tense. I could feel the heat rising in my face, the rush of panic starting to creep in. This wasn’t how I imagined this going.

“Well, I, uh, I just enjoy the solitude,” I stammered, trying to deflect the attention away from my outfit.

He nodded, still not looking uncomfortable. “I get it,” he said. “Sometimes people need a little peace and quiet out here. Just keep in mind, there are some parts of the trail where the wildlife’s a little more… active. Always better to be prepared for anything.”

It was the way he said it that put me at ease—like he wasn’t concerned about what I was wearing, just that I was safe. I nodded, feeling a little relieved but still unsure how to navigate the moment.

“Alright, then,” the ranger said, giving me a friendly wave. “Enjoy your hike. Just be careful, alright?”

“Thanks,” I said, my voice a little more steady now. “I will.”

As he walked away, I stood there for a few moments, still processing what had just happened. The encounter was over, and nothing bad had come of it. He hadn’t called me out, hadn’t made me feel ashamed. Instead, he had just treated me like any other hiker. The whole thing was surprisingly easy, but I couldn’t shake the thought that something about the encounter had shifted in me.

I continued my hike, but now, there was a new layer of comfort. The world hadn’t ended, I hadn’t been ostracized, and in a way, I realized that I didn’t need to hide. I could be myself, even out here, and the world would keep turning.