Crossdressing Stories: How My Girlfriend Helped Me Embrace My Feminine Side

When I first started dating my girlfriend in college, I never imagined she’d be the one to help me unlock a whole new side of myself. But with her support, encouragement, and playful teasing, I discovered something beautiful and unexpected—my feminine side.

My crossdressing journey began when I was 19 and studying in London. I wasn’t tall—just 165 cm—and I was slim, around 50 kg. Despite not having a strong build, I had a delicate and attractive face. That helped me get a beautiful girlfriend who loved fashion, makeup, and fun. She often joked that if I were a girl, I’d be prettier than most. One day, she begged to put makeup on me. As a ‘pure guy,’ I refused at first. But eventually, I gave in.

That first makeover changed everything. She carefully applied soft eyeshadow and light pink lipstick. When I looked in the mirror, I was shocked. A pretty girl stared back at me. I was surprised by how beautiful I looked. My girlfriend smiled and said, “See? I told you you’d look amazing!” She even begged me to go out dressed like that. I was too shy. But deep down, I felt an urge to go outside like that—just once.

What Happened After My First Try?

Once there was a first time, there was a second. After that, my girlfriend often did my makeup for fun. She’d dress me in her clothes and take pictures. I always deleted them right after, worried someone might see.

One day, while shopping together, she bought a long, black curly wig. It didn’t fit her properly, so she threw it to me and said, “Here, it suits your face better anyway!” I put it on—and it really did. With the wig, my look was complete.

My First Time Out in Public

During the National Day holiday, my girlfriend suggested we go shopping. This time, she insisted I dress as a girl and accompany her. By now, after so many private dress-up sessions, the idea secretly excited me. I hesitated, but she kept persuading me. Finally, I agreed—on one condition: she had to make me look perfect so I wouldn’t embarrass myself.

She was thrilled and got to work. She shaped my eyebrows with a blade, applied light blue eyeshadow, foundation, and pink lipstick. She dressed me in a loose white T-shirt and her denim mini skirt. I had never worn anything so short before—it felt cool and exposed. The white shirt was slightly sheer, so she insisted I couldn’t go out “empty up top.” Her 32D bra was too big on me, so she stuck on a pair of silicone breastform and gave me a black floral tube top to wear. It wasn’t much, but it gave the illusion of a C-cup chest. Down below, I wore her snug black panties. They felt surprisingly comfortable.

Her shoes didn’t fit, so I had to wear her sneakers. As I stood up, ready to go, she noticed my leg hair and said, “We can’t have that!” I refused to shave, so she found a pair of black sheer stockings. My legs were already slim, but with the skirt and stockings, they looked long and feminine. Even she was a bit jealous.

Stepping into the World

We left the apartment, my heart racing with excitement and fear. What if someone recognized me? What if people stared? Our rental was close to school, so we quickly caught a bus, then a subway. It was a holiday, and the subway was packed.

I stood behind my girlfriend, holding onto a railing with one hand and resting the other on her slim waist. I could feel her soft curves, and her perfume filled the air. She wore a tight shirt and a lacy blue bra underneath, which I could clearly see from behind. Her skirt was short, and her grey stockings hugged her body. I was aroused, but also terrified.

Because I didn’t want to speak and risk being identified by my voice, I texted her instead. As we stood in the crowd, a middle-aged man behind me pressed closer and closer. At first, I ignored it. Then I noticed him staring at my legs. My slim frame, black stockings, and mini skirt must’ve looked very convincing.

He started to “accidentally” touch me—his hand brushing my thigh and eventually my butt. I was shocked. I messaged my girlfriend, “The man behind me is groping me.” She replied, laughing, “You’re a guy. It’s not a big deal. Have some fun with it.”

I was nervous, but a part of me was curious too. I kept pretending to be busy with my phone. The man’s hand stopped swinging and began resting against my thigh. Then it moved to my hip, just at the edge of my panties. I could feel him behind me—his body heat and something firm pressing against me.

I caught a glimpse of his face in the subway window. He looked calm on the outside, but clearly thrilled. We got off at the next station. He followed us briefly but disappeared into the crowd as we walked away.

Shopping like Sisters

My girlfriend and I were close in size—my legs were longer, her bust was bigger. Together, we drew attention like a pair of stylish sisters. After lunch, we headed to a clothing store. She picked out a vest and some pants. I chose a tight white shirt and low-rise women’s jeans. We used the same fitting room.

Inside, she stripped off her top, revealing her round breasts and blue bra. I was overwhelmed and pulled her into a hug. She giggled and pushed me away, whispering, “Behave! People are just outside. Wait until we’re home.”

She tried on her clothes and looked amazing. I put on my outfit and was stunned—I had curves! Tight jeans and a snug top made me look like a real girl. She looked me up and down and said, “If you were a real woman, I’d totally fall for you.” I laughed and replied, “But I already have the most beautiful girlfriend.”

The Lingerie Store Moment

After paying, we passed a lingerie store. She wanted to buy colorful stockings. I lingered by the bras, curious. A young salesgirl came up and asked what size I wanted. I panicked and said nothing, just smiled awkwardly. My girlfriend noticed and quickly distracted the salesgirl by asking for help with stockings.

She then found a black push-up bra she liked and bought two—one for her, one for me. She also picked out two sexy pairs of small panties. I spotted a pink bra with soft padding inside that gave a great shape, so I added it to the basket.

Trying on Heels

After leaving the store, I didn’t feel shy anymore. Around the corner, I tried on two pairs of low heels. Not too tall—just 5 to 6 cm. I figured that was a good start for a beginner like me.

Conclusion

That day was my turning point. I started scared but ended up walking tall in stockings, makeup, and soft panties. I learned how powerful it feels to express my feminine side. With my girlfriend’s support, I didn’t just crossdress—I came closer to who I truly am.

And I know one thing for sure: that wasn’t my last time. It was just the beginning.