Pairing: Izaya/Shizuo

Prompt: Izaya the fashion victim dresses up (and roleplays?) as Anna Wintour. Kinky stuff with Shizu-chan ensues.

At first, Izaya had taken crossdressing as one of those very short-lived hobbies of his. He was still in high school when one fine day he spotted a very nifty red piece as he strolled around Harajuku. It caught his attention immediately and somehow buying a dress was not that great of a stretch when you spent so much time impersonating a girl anyway. It was only when he tried it on, a thrill of excitement running through him, that Izaya realized that he was hooked for life. The dress clung to just the right places and accentuated the elegant curves of his body. To this day he still kept it for sentimental reasons even though his taste was so much more sophisticated now.
And that was partially due to Vogue and in no small measure to Anna Wintour. The woman knew how to pull off fur brilliantly and her fashion sense was impeccable. One thing he admired were her shades and every other day Izaya would purchase new sunglasses that he of course wore indoors. He usually stopped short of getting a bob hairdo but today he was feeling adventurous so he put on his sleek black wig along with his newest full length dark Armani jacket with a stylish bit of fur on the lapel, cuffs and fringe, it was a perfect match for his slightly shiny Trussardi jeans and Jimmy Choo heels.
Izaya checked the mirror and he was off to strut his stuff. As fate would have it, he found the last person he expected to ever find in a store for brand sunglasses. Heiwajima Shizuo scratched his head as he stared at the shelves with a blank stare that proved what Izaya already knew: Shizuo was fashion challenged. Who else would wear a bartender outfit on every single occasion, Izaya wondered.
The only fashionable decision Shizuo had ever taken in his whole life was dyeing his hair blonde. It gave him a certain edge, Izaya thought, and if Shizuo remained silent and stood aloof with a trademark cigarette tucked at the corner of his mouth, he might very well pass for the stoic kind with hints of cop-gone-bad from a Noir movie. Unfortunately all this allure vanished the moment he began talking. The illusion was then shattered completely. Izaya was considering such things as he approached Shizuo without getting too close so that he could keep an eye on him without it becoming too obvious.
Shizuo noticed a pretty girl standing a few feet from him. He did not handle pretty girls well. First, he became nervous and nothing even remotely coherent occurred to him, to the point that apart from his brother's movies no topic of conversation ever came to mind and then he got angry at himself for being so awkward at which point it all went to hell. Next thing he knew there were vending machines flying, people hurtling through the air, plenty of screaming and general panic. By the time he came to his sense, the girl in question was long gone, or cowering in a corner, or in the hospital.
This particular girl had a presence to her. She stood confidently as she expertly tried on pairs of sunglasses all of which suited her somewhat familiar face. Shizuo could tell that she was classy, too. In a word, she was completely beyond his league. Which was part of the reason why he found himself casting furtive glances in her direction, it was a bit like staring at a billboard.
Shizuo was not the most discreet of people, to put it mildly. Izaya could positively feel him checking him out. If eyes could eat than Izaya was being devoured and enjoying it greatly. Izaya bridged the distance between them and addressed him with a curt but very polite voice:
"Are you looking for something in particular?"
Shizuo jumped and fumbled some.
"Er, no, not really. My brother recommended this store, he told me I should get some sunglasses to improve my image, I guess. I'm not too good when it comes to fashion."
Izaya was very amused. Shizuo had not recognized him and he was getting a kick out of this unexpected bashfulness.
"Is that so?"
"Yeah. I mean, yes."
"May I suggest something?"
Izaya did not wait for a reply. He reached for a pair of narrow light blue-tinted shades.
"Sure. But aren't those, you know…a bit girly?"
Izaya held the glasses by the rims and placed them on Shizuo.