My First Time Crossdressing: How a Silk Qipao Changed My Life

I never imagined I’d fall in love with crossdressing. It all started in high school, when a simple request from my teacher changed my life. I was shy, awkward, and had never worn women’s clothes—but that day unlocked something deep inside me.

It turns out, a single moment can ignite a lifelong passion. My first time crossdressing was unexpected, but also incredibly exciting. I wore a silk qipao, my teacher’s bra, and saw myself as a girl for the very first time. That experience shaped who I am today.

What started as a shy favor soon became a personal transformation. Curious how it all unfolded? Let me take you back to the beginning.

Have You Ever Crossdressed for the First Time and Felt… Right?

That moment came for me in high school. My homeroom teacher was a stunning woman—elegant, poised, and always dressed with care. She came to visit my home one weekend, and during the visit, she found out that my dad was a fashion designer. She asked him to help make her a custom silk qipao (traditional Chinese dress).

My dad, always helpful, agreed. He measured her, sketched the design, and got to work that same night. A week later, the dress was done. My teacher returned to our home to try it on, glowing with excitement.

She slipped into the qipao and admired herself in the mirror. But she couldn’t quite see the back of the dress. She turned to me and smiled, saying, “You and I are about the same size. Try it on for me—I want to see how it moves.”

I froze.

Have You Ever Worn a Woman’s Bra for the First Time?

I was nervous. Just watching her in the silk qipao had stirred feelings I didn’t understand yet. And now she wanted me to try it on? My heart pounded. My cheeks burned. I hesitated, but she encouraged me gently.

“There’s no one else here,” she said, “and it’s just for a moment.”

Reluctantly, I agreed.

I slipped out of my clothes, left only in my shorts, and she handed me her bra—a thick padded one that held the shape of her curves. It was warm from her body and smelled like her perfume. I didn’t know how to put it on, so she helped me. She hooked the back, adjusted the straps, and stuffed soft fabric into the cups.

Suddenly, I had breasts.

And then—she helped me into the qipao.

Have You Ever Seen Yourself as a Woman in the Mirror?

The silky fabric slid over my skin. It was snug around my new chest, tight at the waist, and hugged my hips. My teacher buttoned the front clasps with care, smoothing the fabric over me.

I turned to the mirror.

And there she was.

Not the shy teenage boy I was used to seeing… but someone else. A beautiful, soft version of me. My heart raced. I turned in place, watching how the dress shimmered with every movement. I had never felt anything like it—elegant, feminine, right.

That was my first time in feminine clothes. My first time wearing a bra, a qipao, and presenting myself as a woman. I didn’t realize it then, but that moment planted the seed for a passion that would grow for decades.

Have You Ever Wanted to Make Your Own Dresses?

As it turns out, that wasn’t a one-time thing.

Throughout high school, my dad continued designing outfits for my teacher. Every time she visited, I helped model the clothes. And sometimes, when no one else was around, she let me try on her own bras, dresses, and even skirts.

By the time I reached university, I had learned how to sew from watching my father. I began making my own feminine clothes in secret. I even crafted a delicate dress, folded it into my suitcase, and brought it to campus. Though I never wore it outside, just knowing it was there made me feel safe.

That’s when I knew—crossdressing was a part of me.

Did Your Spouse Support Your Crossdressing?

Years passed. I got married and had children. But I never gave up crossdressing.

To my surprise, my wife understood. She saw how much joy it brought me. She accepted that this was a part of who I am. That support made all the difference.

Now, she even helps me choose outfits and do my makeup. And in return, I love her even more deeply.

Are You Naturally Feminine Too?

I was lucky in many ways.

• I don’t have much body hair.
• My Adam’s apple isn’t noticeable.
• I’m 170 cm tall, weigh 55 kg, and have naturally narrow shoulders.
• My skin is soft.
• My features lean delicate.

With a little makeup, the right wig, and a well-fitting dress, I can pass quite convincingly. I’ve even grown my hair long over the past few years. Now, I switch effortlessly between masculine and feminine looks.

Some days, I’m a handsome guy. Other days, I’m a seductive lady.

And both are me.

Conclusion

That one qipao changed everything for me.

Crossdressing became more than just fabric and makeup—it became freedom, identity, and joy. Whether you’re just starting out or have your own stories to tell, remember: you’re not alone.

We all start somewhere. And for me, it was a teacher, a bra, and a beautiful silk dress.