Crossdressing Stories

It started off like any other Saturday. I was planning to meet my friend Dylan for lunch, and we were supposed to hang out for a couple of hours before I caught the bus home. But things didn't go exactly as planned.

After we finished eating, we walked around the city for a bit. We found this small thrift store tucked between two cafés. Dylan loves finding old clothes and turning them into cool outfits, and I usually just tag along. I've never really told anyone this, but I always look at the women's section first when we go to places like that.

I don't even know when it started—maybe when I was a kid and stole glances at my mom's closet—but I've always liked the way feminine clothes felt. The softness, the colors, the way they moved. I don't wear them in public, just in my room, behind closed doors. But I always wondered what it would feel like to wear them outside. To be seen and not hide.

So there we were, in the thrift shop, when Dylan pulled a cute pink hoodie and a short denim skirt off the rack. "Dude," he said, holding them up, "you should try this on. It's totally your vibe."

I laughed, startled but a little thrilled. "You think so?"

"Yeah. I mean, you always glance at this stuff. Don't think I haven't noticed."

I froze. My heart skipped. "Wait… what?"

He smiled, casual as ever. "It's cool, man. I don't care. Honestly, I think you'd look great in this stuff. No one here knows you. Wanna try it on?"

I looked around. The shop was nearly empty. I hesitated, heart pounding. "What if someone sees?"

"Then they see," he shrugged. "You're just trying on clothes. Come on. Live a little."
I followed him to the fitting rooms, hands shaking as I stepped in and pulled the curtain shut. I changed into the skirt and hoodie. Looking at myself in the mirror, I barely recognized the person staring back. But it didn't feel like pretending. It felt like I'd finally taken a breath after holding it in for years.

When I stepped out, Dylan's face lit up. "Damn, you're pulling that off way better than I thought."

I laughed, half-giddy, half-nervous. "Really?"

"Totally. You know what? You should come over to my place tonight. We can hang out, order food, maybe try more outfits. My roommates are gone for the weekend. It'll just be us."

A rush of excitement and fear hit me all at once. "I didn't bring anything to stay over."
"No problem. You can wear something of mine. Or keep that." He nodded at the outfit I had on.

I didn't even have to think. "Okay, let's do it."

We paid and left the store. On the way to his apartment, he told me stories about people he'd styled before, how fashion's just a way to play with identity. I kept glancing at my reflection in the shop windows we passed, surprised each time. It was still me. Just a freer version.

When we got to his place, he tossed me some makeup wipes and a brush. "Wanna try a little makeup? Just for fun."

I nodded. I'd watched enough YouTube to fake my way through blush and gloss. My eyeliner was shaky, so Dylan leaned over and helped fix it. "You've got a steady hand," I joked, my cheeks warm.

"I've practiced on worse canvases than you," he winked.

By the time I was done, I looked soft. Pretty, even. We took a few selfies—just for us—and he offered me a pair of fuzzy socks. "You're not fully cozy until your feet are warm."
We curled up on the couch with blankets and pizza. Halfway through the movie, I shifted to grab a slice and accidentally knocked over my soda. It spilled across the floor and splashed onto my skirt.

"Crap!" I jumped up, panicking.

Dylan laughed and grabbed paper towels. "You good! Come on, it's just soda. The skirt survived worse at the thrift shop."

We knelt down together, cleaning, and I caught him smiling. "What?"

"You're different tonight," he said. "Looser. Happier."

I didn't know what to say. So I just smiled back.

Later, we did a mini fashion show. Dylan had a box of old accessories—ribbons, chokers, even clip-on earrings. We mixed and matched pieces, laughing at some combinations, admiring others. He pulled out a floral tank top and matching shorts for me to sleep in. I hesitated, then slipped into them.

When it was time for bed, he let me use the guest mattress on the floor of his room. As I got under the covers, he looked over and said, "You know, if you ever want to go out like this—really go out—I'd back you up. One hundred percent."

I blinked. His voice was calm but sincere.

"Thanks," I said softly. "I'm not ready yet. But someday… maybe."

He nodded. "Whenever that day comes, I'll be there."

That night, lying in borrowed pajamas, faint eyeliner still on, wrapped in warm blankets and Dylan's words, I felt something I hadn't felt in a long, long time.
It was just a skirt at first. But that night, it became so much more.

By Ethan