Inspired by this confession on the Ikebukuro confessions blog:
ikebukuroconfessions(dot)tumblr(dot)com/post/24191926404/all-the-pictures-of-shizuo-wearing-the-pink-heels

and this is the dress~:
www(dot)summerdress(dot)

Disclaimer: I do not own any of the charaters or Durarara!

Warning: Shizuo in a dress and heels. Dont want, dont read.

Curiosity

Hot fuschia pink.

Five inch heel.

Round toe pump.

Exactly my size, this little detail had cause me hell. Do you have any idea how hard it is the figure out exactly what size I was in woman's shoes.

Are those stiletto heals?

...

Maybe not?

...

The fuck would I know?

...

Shit am I really going to do this?

My hand reaching to close and lock the door to my small one bedroom apartment answered the question for me.

I made my way into my bedroom, immediately opening the closet and searching for a white cardboard box, the kind that clothing comes in. When I found it I took both the box and the shoes that I had just received in the mail to my bed and set them both down, opening the box and staring at the contents.

A single strap just above the knees dress, in matching color with the shoes.

Holy hell I was about to do this.

Internet shopping was an amazing thing. I could buy things like these with no judgements and didn't even have to look the FedEx guy in the eye if I had to sign for anything. No one in the world outside of me had to know that I, Shizuo Heiwajima had bought a fuschia pink dress and matching five inch heels.

Now don't go jumping to assumptions, I'm not a transvestite or anything, hell I'm not even gay. But when Friday night with Kyohei and Tom brought about a discussion about what it must be like to be a girl, what wearing skirts, or dresses, or high heels felt like, well eventually curiosity got the best of me. So like any healthy, but curious, 24 year old man... I went shopping online. Five days of shipping for the dress, and 9 for the shoes and here I am, staring at my purchases, a knot forming in my stomach telling me to burn the articles before I did something stupid.

...

I had spent over four thousand yen(about fifty US dollars) on this stuff... If I turned back now it would be a terrible waist of money...

Fuck it.

I reached out for the dress, figuring I should put that on first. I held it up in my hands scanning the front and back for a zipper, or button, or really anything that could give me a hint as to how to put the bloody thing on.

Nothing.

Very, very helpful.

Was wearing things like this just... natural for girls?

With a shaky sigh I began to undress, figuring I just slip it over my head. Once I was down to my underwear I took one last look at the dress, my last chance to stuff the clothes in the depths of my closet, never to think about this moment ever again.

Damn this curiosity.

I took the dress in my hands again, this time by the bottom hem and lifted it above my head, slipping it onto my body properly.

...

...

I Shizuo Heiwajima was wearing a mother-fucking dress.

And I wasn't even done yet.

I eyed the mirror across the room.

No.

I was not going to look yet. If I did, I would tear the thing to shreds before I even put on the shoes.

Fuck. What the hell is wrong with me.

Another sigh as I turn back to my bed and sit down, taking one of the shoes in my hands. The dress fell between my legs loosely as I inspected the shoe. There was no way these were comfortable... and, how do women walk in these things?

I crossed one leg over the other, lifting my foot up as I slipped it into the colorful shoe. It fit well, a little tight around my toes, but not awfully tight. I set my foot back on the ground, the arch of the heel causing my knee to raise higher than the other.

I quickly slipped on the second and planted my feet down on the ground, with a deep breath I straightened my legs and stood up. My legs wobbled in the heels and I stuck my arms out to save my balance, sighing in relief when I was able to stay standing.

I took my first step, my ankle wobbling, once again causing me to nearly trip, I rightened it, however, just in time.

A few more wobbly steps and I was able to get in front of the mirror. I didn't look at first, I didn't want too. I knew it would look awful, but when I looked up at the mirror, I never thought it would look /that/ awful.

The shoe's only made my feet look even bigger, the dress that fell just above my knees, very much not complimenting the muscles of my legs. The top of the dress, obviously made for a dainty, breasted, body, making my shoulders and pectorals look unnatural, not to mention that my lack of womanly hips did nothing to help the dress.

At that point I couldn't help but to cover my mouth and laugh loudly in my hand. This on a girl like Celty or Verona would be cute, but on me it looked horrific. I looked down at what I was wearing, remembering the point of this whole thing, and turned around, taking a few strides across my room.

The heals were a pain in the ass, or feet I suppose. They were uncomfortable after only a few minutes of wearing them, and only walking around my room. The dress however was different. The top of the dress was stretchy and fitted my chest, though awkward looking, comfortably, the single strap was a bit awkward considering the size of my shoulders, that the dress wasn't made for, but not uncomfortable. The bottom of the dress flowed below me, feeling almost as if he wasn't wearing any bottoms at all, it was open, free.

At least I could see the appeals of a woman wearing a dress.

...

Another look in the mirror told me that I would never /ever/ be doing anything like this again.

I shook my head with an amused smile as I turned away from the mirror, facing the opposite side of my room to walk back over to my bed.

There was a window on that side of my room, and about .5 seconds after I realized that I had left the window open there was a flash, then a snicker of a laugh.

"You know that dress looks awful on you right, Shizu-chan~?"

It took me one point five seconds to realized what had just happened.

Two to kick off the shoes.

And only an instant to chase after Izaya with murderous intent, only hoping to get my picture back from him.

And yet, it took me until that disgusting, pain in the ass, flea called Izaya pointed it out to realized that I was, in fact, chasing him in that bloody pink dress.

And it will take me a life time to live that down.

My first attempt at first person~ I read the confession on ikebukuroconfessions(dot)tumblr(dot)com and I kinda... had to write it~
Review please~ Tell me what you think~!