My Best Friend's A Cross Dresser

Disclaimer: I do not own Pokemon or any of its characters.



My eyes are opening slowly and my brain is just now realizing it.
"Have a nice catnap, Meowth?"
I yawn and stretch out on the bed, nodding my head, too groggy to talk just yet. When my vision cleared I saw James sitting on the edge of the bed, clad in his boxers. He reached down for something I couldn't see and I realized he was pulling some stockings up onto his legs.
"Whatcha doin'?" I asked, sitting up.
"Getting ready. Jessie and I are about to head out."
"It's dat late?!"
I looked over at the window and noticed, indeed, it was already getting dark outside. It was October 31—Halloween. Jessie and James were going trick-or-treating while me, Wobbu, and the rest of the pokémon were staying at the cabin, loaded with candy, in case anyone came by. Most people would think my two human companions were too old for trick-or-treating, but I think it's cool they still do it, since it's obviously something they enjoyed when they were younger. James stood and I watched him as he walked over to his closet and took out a fluffy pink dress.
"Of course. A dress," I said.
He looked at me over his shoulder.
"Well, Meowth, I am a princess tonight."
"More like a queen, heh!"
He stuck his tongue out at me and returned to pulling on the dress. Heh. How immature.
"So…why do you wear dresses so much, Jimmy?"
I could see his face illuminating a light blush.
"Because…they're good for disguises," he replied.
"Yeah, sure…but I'm startin' to think you like it."
He turned even redder and shook his head defiantly. Yeah right.
DENIAL!
I watched as he expertly laced up the bodice and smoothed out the long skirt. He may deny that he liked dressing in drag…but he did it really well. Strange…that a man could naturally look so good in a dress. He went over to the mirror and began to put foundation on his face, followed by some faint blush. As if he wasn't blushing enough already.
"Goin' all out tonight, huh?"
"Halloween only comes once a year," he replied coolly.
Please. You're in Halloween Land 24/7, Jimmy boy.
"You always go as a girl, don't you?"
"No! I was…um…I was…"
I waited patiently, tapping my claws on the bedside, nonchalantly. He looked at me in the mirror and saw the big grin on my face.
"Shut up," he grumbled, now applying a pink shade of lipstick.
I smiled, slightly satisfied. I was awaiting a full confession.
"Fine," he sighed, defeated, carefully putting on mascara and eyeliner. "Maybe I like wearing dresses and skirts, okay? They make me feel pretty…"
I couldn't help but laugh out loud at the last part. He stood and turned to face me, smiling a little.
"I don't look that bad."
And you know, he really didn't. He looked really good. Almost beautiful. The pink dress might have looked silly and dramatic, but besides that he was a vision. His long, accented eyelashes fell over his sparkling emerald eyes. His smiling, glossy lips matched the pink blush that was settled over his boyish, but handsome face. He was pulling on some white elbow-length gloves when he looked up at me.
"Meowth? You're staring…you okay?"
I quickly shook my head, trying to hide my wonderment and admiration.
"I'm fine, I'm fine!"
He smiled at me and nodded.
"Oh, okay."
I looked away from him for a moment, then thought of something I forgot to ask.
"Hey, what's Jessie going as?"
He looked at me, grinning.
"Oh, didn't you guess?" he winked. "She's my Prince Charming!"
I gave him an odd look for a moment, then rolled my eyes.
"What?"
"James…you're very strange."
He blinked, then chuckled.
"Too bad. You're gonna have to get used to it."
"Oh yeah, why?"
He sat down beside me and reached over to scratch behind my ears.
"Because you, Meowth, are one of my best friends. So you're stuck with my strangeness for the rest of your life!"
He leaned down and planted a kiss on my golden charm.
"Blech! James!" I exclaimed, pushing him away.
He smiled down at me, his eyes closed and a light chuckle escaping his lips. I looked back up at him, desperately trying not to smile.
"Hey! Darling princess! We need to head out!" Jessie called out through the door.
"Coming, my prince!" he called back, sweetly.
He gave me one more pink-coated smile before walking out. I stretched a few times, then stood to join the other pokémon in the front room. I cast a quick glance in the mirror and saw a pink lipstick mark on my charm.
"…"
James is my best friend.
"…"
And he's a cross dresser.
"…"
And I wouldn't want it any other way.
"…he's so strange."
My mouth curled up into a smile, matching the pink one on my charm.

End.