How I Came to Live as a Girl (Part II): How I Came to Love Crossdressing

After passing the physical exam and being accepted into high school, I thought the hardest part was behind me. I had survived the system and secured my place in the future. Everything was supposed to go back to normal, but as I settled into my new life, I realized something had changed. The female identity I had adopted to survive wasn’t just a disguise anymore—it had begun to feel like a part of who I was.

I wasn’t sure how to navigate this new shift. What was once merely a means of survival had started to blur with something deeper. I thought I was just getting through it, but soon, I found myself wondering: who was I becoming now?

The First Time I Felt Truly Free

It wasn’t until the school’s annual charity event that I truly realized the shift within myself. The theme for that year was “Historical Figures,” and I was assigned a female character. At first, I resisted. I felt a familiar knot in my stomach, remembering the first time I had worn a skirt, a time when it was all about survival, not choice.

I thought back to how I had reluctantly played the role of a girl to get through the physical education requirements, how every inch of fabric had felt like a weight, a disguise to endure. This time was supposed to be different. I wasn’t doing it out of necessity, and yet… I couldn’t shake off the nagging sense that I was being forced into it.

When I stepped into the costume room, the first thing I noticed was the vivid colors and delicate fabrics. The costume—a vintage dress—was much softer and more elegant than anything I had worn before. At first glance, it felt like I was being pulled into someone else’s world, someone else’s identity. But the second I slipped it on, something in me relaxed. The fabric brushed against my skin in a way that was… comfortable, even soothing. The tightness of the corset was constricting, yes, but it was also strangely supportive, like being held together in a way I hadn’t expected.

Then there was the makeup. I’d never really worn makeup before—not in this way, at least. Applying the soft pink blush, the mascara, the subtle eyeliner, I felt an odd sense of… transformation. It wasn’t about pretending to be someone else. No, it was like a puzzle piece clicking into place. My face didn’t change drastically, but in that moment, I began to see a version of myself I hadn’t acknowledged before. It wasn’t a different me—it was an aspect of me I hadn’t allowed myself to recognize.

As I gazed into the mirror, adjusting my hair and the folds of the dress, something shifted. The discomfort I had always felt when wearing women’s clothes had faded. It wasn’t about survival anymore—it was about expression. I looked at myself, and instead of seeing an outsider or a fake, I saw someone who actually fit the role I was playing.

When I stepped out, I wasn’t just playing a part. For the first time, I felt like I was truly expressing something about myself. I could feel the eyes of my classmates on me, but it wasn’t a sharp, judgmental stare. There were looks of surprise, certainly, but they were followed by smiles, by comments that didn’t make me want to shrink back into myself. In fact, the attention felt… good. More than that, it felt right.

The compliments started coming in, small at first, then growing bolder. “You look great in that dress,” one of my classmates said, laughing as she adjusted her own costume. Another added, “I never thought you’d look so natural as a girl.” I wasn’t sure how to respond. I wasn’t sure whether to thank them or deflect the compliment. But the more I heard, the more it became clear—I wasn’t pretending. I wasn’t just passing as a girl. I was owning it.

That evening, when I stood before the audience, feeling the weight of their gazes, it didn’t feel uncomfortable anymore. It felt empowering. The dress, the makeup, everything—it wasn’t just an outer shell. It was a declaration.

For the first time, I didn’t feel like I was pretending to be something I wasn’t. It was more than that. I felt like I was becoming someone—someone I hadn’t expected, but someone I was learning to accept. There was a freedom in that realization, an openness I hadn’t known before.

The rest of the evening passed in a blur. I smiled, laughed, and mingled with friends, but deep inside, I was silently processing something much bigger. I realized that this wasn’t just about wearing clothes, or about passing as someone else—it was about how I felt in that moment. And in that moment, I felt like I was exactly who I needed to be.

The Shift: From Necessity to Desire

After the event ended, I found myself lingering in the quiet of my room, looking at the dress that had become both a symbol of my transformation and the catalyst for something I hadn’t expected.

I began to notice something odd—something I hadn’t considered before. I wanted to wear the dress again. Not for the event, not because I was required to, but because I liked how it made me feel. The way it fit my body, the way the fabric draped around me, the way I moved in it—it all became part of a new routine, a new self-expression.

I wasn’t sure when the shift had happened, but I realized I didn’t feel uncomfortable anymore. In fact, I felt more at ease with this part of myself than I ever had before. I wasn’t wearing the dress for anyone else—I was wearing it because I wanted to.

This wasn’t about survival anymore. This was about choice, and for the first time, I felt a deep connection to something that had once felt like a mask. I wasn’t just dressing up—I was beginning to express a side of myself that had always been there, quietly waiting to be recognized.

Breaking Free: Embracing the New Me

Over the next few weeks, I began to experiment more with the clothes I wore. At first, it was just small things—maybe a pair of tights here, a skirt there—but soon, I found myself dressing more intentionally. The tightness of a fitted blouse, the soft texture of a skirt, the feeling of delicate fabric on my skin—it all became part of a new routine, a new self-expression.

I found myself drawn to the femininity of it, not just because of how I looked, but because of how it made me feel. It felt freeing. I wasn’t hiding behind anything anymore. For the first time, I felt like I could be myself—all of myself, with no need to compartmentalize or deny any part of who I was.

I started to realize that the line between “male” and “female” wasn’t as clear as I had once thought. And that wasn’t a problem; it was a new truth.

End of Part II