Crossdressing Stories

I grew up in a small town where my mom, older sister Lily, and I lived in a creaky yellow house on the edge of Main Street. Dad left when I was three—Lily says he couldn't handle "all the estrogen," which made Mom snort-laugh every time she heard it. By the time I was ten, Lily had started college, so it was just me and mom most days. She worked at the diner downtown, and I spent afternoons either helping her wipe counters or playing with the neighbor girls, Mia and Clara, who lived next door.

That summer, mom decided we'd visit her sister, Aunt Lila, in the countryside. Aunt Lila was the fun aunt—she had no kids but kept a closet full of old costumes from her theater days. Her house smelled like cinnamon and had a big porch where fireflies danced at night. I'd only seen her a few times, but Lily always said Aunt Lila "didn't care about stuff like boys and girls."

The first day there, Mia and Clara (who'd tagged along with their mom) wanted to play "movie stars." Aunt Lila clapped her hands and said, "Perfect! I've got just the outfits." She pulled out a trunk filled with frilly dresses, sparkly shoes, and even a box of clip-on earrings. Mom rolled her eyes but smiled, saying, "Go on, let the kids have fun."

Mia grabbed a silver sequined dress first, Clara a pink one with puffed sleeves. That left a blue-and-white gingham dress with a big bow at the waist. "This one's for you, Jamie," Aunt Lila said, handing it to me. I hesitated—at ten, I knew boys didn't usually wear dresses, but Aunt Lila's voice was so matter-of-fact, like she was handing me a regular shirt. "It's just for the game," she added, winking.

Mom helped me change in the bathroom. She found a pair of Lily's old white pantyhose and dress in her suitcase. I groaned, "Mom, those have lace!" but she just said, "They'll keep the dress from itching". Then came a petticoat that rustled when I moved, socks with lace trim, and tiny black Mary Janes that Aunt Lila said used to be hers when she was my age. The dress buttoned up the back, and Mom tied the bow so tight I had to suck in my stomach.

When I walked back to the porch, Mia and Clara squealed and clapped. "You look like a princess!" Clara said, sticking a pearl headband in my hair. Aunt Lila pulled out a compact and dabbed pink lipstick on my lips, then brushed powder on my nose. "There—now you're ready for your close-up," she said, pretending to take a photo with her imaginary camera. Mom just nodded, sipping iced tea like this was the most normal thing in the world.

Mr. Whiskers, Aunt Lila's mischievous cat, wandered over and batted at the lace on my socks. Before I could react, he jumped onto my lap, purring loudly and leaving white fur on the gingham skirt. "He thinks you're part of the show too," Aunt Lila laughed, scooping him up. But he kept twisting to peer at me, as if wondering why I looked so fancy.

We played for hours—singing into broom microphones, "dancing" on the porch, and acting out silly stories where I was "Lady Jamie" who saved the kingdom from a dragon which was actually Aunt Lila's cat, Mr. Whiskers. No one made a big deal about the dress; it just felt like part of the game. When dinner time came, I forgot I was still wearing it until Mom said, "You might want to change before we eat, unless you want spaghetti sauce on that pretty bow."

That night, Aunt Lila took real photos—me in the dress, holding a pretend microphone, Mia and Clara flanking me like backup singers. She promised not to show anyone, but years later, when I was sixteen, I found those photos in Mom's album. By then, I'd started borrowing Lily's old sweaters sometimes, just to see how they felt, and Mom would say, "That color suits you, kiddo," without any judgment.

Aunt Lila's visits became a yearly thing, and each time, the dress-up games got more elaborate. By fourteen, she'd bought me my own pair of glittery flats and a soft pink nightgown "for sleepovers." Lily, home from college, joined in too, painting my nails and teaching me how to braid hair. It wasn't about being a girl—it was about feeling comfortable, like I could be whoever I wanted when I was with them.

Now, at twenty-two, I still keep that gingham dress in my closet. Mom jokes that it's "vintage," and Aunt Lila sends me lace socks every Christmas. Sometimes I wear them around the house when I'm alone, or to Pride parades with friends who just say, "Looking good, Jamie." It's not a secret anymore; it's just part of who I am—the kid who played princess on a porch, and the adult who still likes how lace feels against their skin.

Life's funny that way. The people who matter don't care about dresses or labels. They just care that you're happy, even if "happy" means wearing a bow bigger than your head and dancing with fireflies as your audience.

By Jamie

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