AN: It is now day "four" of the March Mayhem … anyways, enjoy. Essentially, it's a cross-dressing!Mikado being pursued by clueless!Masaomi and being hounded by a jealous!Aoba. This chapter is mostly setting up. So there isn't that much dialogue … yet. Just a lot of Mikado reasoning. Remember, reviews – bountiful reviews – is what's going to keep the March Mayhem (and us) moving, so review!

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Disclaimer: We do not in any way own the characters/scenes/ … oh you know the drill I'm sure.

From Best Friend to Girlfriend

A Durarara! Fanfiction written by Foxy

Chapter Two: The Plan to Escape

A few weeks earlier …

… Bored.

That was the thought that crossed Ryuugamine Mikado's mind as he lie flat on his back, staring up at the ceiling of his ratty apartment. He was bored. It was that simple.

It wasn't like his life had become too monotonous. Far from it, the series of events that had occurred thus far turned out far more adventurous and exciting than he ever expected. His exciting life wasn't confined by merely being the founder of Dollars, either. He was now gaining plenty of "enemies" by both managing Dollars and in becoming the figurehead of the Blue Squares. And since the Blue Squares was more open in the world than Dollars, his face was surely becoming known by people he'd rather not know or ever chance to meet – at least, not until he was bored with life again.

But, as of right now, the Blue Squares was proving more annoying than interesting. They had taken to tailing him. And they were tailing him everywhere. To school, from school, to the stores, and … pretty much everywhere.

He rolled over, trying to think of a way to get rid of them. He'd tried evading them, but they were pretty good at what they did. Maybe I need a disguise of sorts … He could dye his hair, but eventually they'd notice that. And sunglasses and a hat and long coat were far too overused. Then I should disguise myself as a completely different person. He thought through a variety of disguises, but of course, he had to cross each one off. He was just too recognizable. But then a strange idea hit him … What if … I dressed myself as a girl?

He started laughing a little, but his smile faltered when the image wouldn't go away. That I might actually be able to pull off … since I can pick a wig and some fashion, but … he was straight! What if someone found that out? It'd be a lot more embarrassing than other disguises … not to mention, he didn't know a whole lot about girls' fashion. He had no idea how they picked what they picked. Or why.

But, after a while, he couldn't think up anything better. Frowning, he decided he'd try a disguise. It would prove interesting to fool the surveillance … and a girl disguise would probably be his best bet. Okay, tomorrow, I'll go to the store, pick some … girl stuff up, and we'll see how it goes.
*

Mikado gave a small wave back with a crooked smile, feeling his eyebrow twitch as the two members turned back again, but were clearly more alert and on the lookout. Seriously … they don't even let me go shopping alone anymore …? Their ever-increasing surveillance was beginning to make him uncomfortable. Well, this wouldn't do. There was no way he could easily pick up disguise materials without them noticing and reporting it back. He'd probably be the end of every joke if the two caught him heading into the aisles that specifically carried female items and picking up what he required. Heck, he didn't even think the store would let him get away with trying out the girl's clothes.

Then … what do I do? Even if he got the items, he wouldn't know what to do with them. The world of frills, fashion, make-up and pretty colors was alien to him. He considered going to a girl for advice, but then he realized that the girl's reaction to his reasons might not be worth it. He didn't want Anri to think he liked cross-dressing or that he was experimenting or anything strange; he wasn't. He just wanted to get away from the surveillance and make it convincing that it wasn't him. Karisawa-san, who was an otaku to the maximum and probably daydreamed about this sort of thing in her spare time, would probably scare him. He also thought about Celty-san, but could he really trust a headless fairy's sense of fashion? … Probably not.

He started glancing around, trying to get an idea of what he should do. Maybe I should do some sort of research before going through with this … but how? Observing girls? Reading girly things? His eyes drifted over to the magazine rack, and an idea came to mind. Fashion magazines. Clothing magazines. That'd be perfect. His tail wouldn't be able to see exactly what it was he was buying, and the store wouldn't question him too much about it. Plus, some clothing magazines allowed online, phone, or mail orders. So he made his way over to the magazines, and tried not to make it obvious that he was looking at those specific magazines (his two friends had moved closer as well). As he managed to pull some of the magazines off the rack and make his way to the cashier, he inwardly smiled to himself.

This was exciting. Well, not really the "dressing up as a girl" part, but more of the "how long can I do this before they notice? If at all?" It would prove amusing to fool his very own surveillance and gangs by learning how to cross-dress well. The cross-dressing wouldn't be for too long, anyways. He'd either grow bored of it, get caught in it, or his surveillance would gradually vanish or he'd find another way to fool it.

The cashier didn't even seem to care as the "girly" magazines slid across the built-in table top scanner and were lightly shoved into a bag, along with the other things Mikado had picked up to stock his fridge. He probably saw girls on the covers and assumed "ah, it's what all male teenagers buy" (even though Mikado, being the fairly shy guy he was, would deny to the grave that he'd purchase such a thing) and didn't bother to look at the true nature of the magazines. Mikado paid for his purchase, took the bags, and headed back home, with the two members following behind.
*

He couldn't help but feel a little perturbed as he closed and locked his front door, slipping his shoes off and walking over to where his laptop was stationed. The two Blue Squares members that he'd met in the store had followed him home to make sure he got home. He pretended he didn't notice, but he did, and the surveillance was rather blatantly obvious. They walked where I walked, stopped when I stopped, and they finally headed back in the direction they came when I reached my street. He knew that they wouldn't come right up to his apartment, though. The surveillance wasn't his orders; it was Kuronuma Aoba's. If they started coming too close to his apartment, it would mean treading into a dangerous gray area in which Mikado and Aoba would have to establish leadership boundaries. But it didn't seem like it would have to come to that just yet. Mikado didn't have enough real power and loyalty to back himself, and Aoba-kun didn't seem to be making too many aggressive behaviors.

Pushing such thoughts aside, he sat down at his table where his laptop was, pulled out the girly magazines as he waited for his laptop to turn on, and started studying them. He didn't know a thing about how girls dressed, so he assumed the magazines could help him, since asking any of the girls he knew would probably end horrendously. He looked for modest clothes that he could hide in, as well as things he could afford. He used the internet to double check on what he needed (stockings, what a "padded" bra was, etc.). A few hours later, he completed the form in the magazine, wrote a check, stuck it all in envelope and stuck it in his neighbor's mailbox (he didn't know if the Blue Squares liked rifling through his mail, so he thought he'd be on the safe side). Now he'd just have to wait a while longer for the clothes to arrive. For now, he'd do his homework, and later, he'd start researching girly … mannerisms. And practice his girly voice.
*

About a week and a half (and many annoyances) later, a box from the company arrived for him. He couldn't say he was excited, per say, but this would prove interesting. He lugged the box into his apartment, and opened it. He took all the clothes out, blushing while cautiously holding the undergarments, and laid them out on the table. Well, I should probably try this out soon. He decided. He stripped down to his boxers, and, whilst having a mental battle, decided on putting the bra on first.

Wait … how do I even do this? He wondered, struggling as he attempted to fasten the padded bra in back. He couldn't see where the hooks were supposed to go. He fought with it for several minutes, before giving up and slinking back to his laptop and looking up what he was supposed to do. I better remember to delete my history after all this is done …

He soon found a trick for hooking a bra; he pulled the straps off, turned the base of the bra backwards, hooked it in the front, turned it back around, and then pulled the straps up. Finally, one of the worst parts was over. Now he just had to stuff it so the padding didn't bend in at weird angles. After finishing that, he picked up of the other clothes he had ordered off of the table, holding up – of course – the other undergarments, and flushing a deep red at the thought of wearing them. I feel like a complete pervert. But I'm not doing this for perverse reasons, so … so … he set them back down, and instead picked up the soft, dark navy plaid skirt. The bra was bad enough. But the skirt was knee-long, so maybe he could still wear his boxers under the skirt without any trouble …?

He pulled the skirt up, letting the stretchy band fit around his waist. He looked at himself in his pathetic mirror, and frowned. Sadly, the boxer outlines could be seen through it. So, with plenty of mental curses and stutters, he exchanged his boxers for the … panties. At least they weren't frilly panties – he didn't think he'd ever work up courage to buy those! – they were just simple cotton panties that could hide his parts rather well. Still, it felt … very uncomfortable.

Ugh, let's just get this over with. He knew he was still blushing like crazy. He took the knee-length stockings and slid them up, for once glad he didn't have a muscular frame. It meant he didn't look too much like a freak in girl's clothes (even though it made him feel like one). He then put on the purple (and frilly) blouse, adjusting it so the bra couldn't be seen. Next, came the long-sleeved jacket, which was also navy blue and came down to his hips. He buttoned two of the buttons towards the top (as it was done in the fashion magazine), and looked at himself in the mirror. I look like a drag queen. He gagged a little, but he knew it'd look better once he tried the wig and shoes. He didn't have make-up yet; make-up was still something alien to him, and he didn't feel mentally ready to try that yet.

He tried on the traditional shoes, making sure that he was in them properly. But when he tried to move, he nearly killed himself by tripping on the low heels. How do girls walk in these things? He wondered, and carefully walked himself over to the table again, this time picking up the wigs, pins, hair bands and scissors. He headed back to the mirror, trying to re-adapt to the shoes. On went the wig, and he frowned. It was a little too long, really … at least, he thought so. So he pinned it on, and took the scissors, and cut out some bangs (that covered his own short hair at the least) and cut the hair so that it hung to about chest level. He saw his eyebrow twitch in the mirror as he smiled at himself, finally getting a full look at how he looked. It's almost scary how well I can probably pull this off … he prayed no one would ever find out about this, though. He made sure the wig was secure before putting in the hair bands, giving himself two pigtails that hung loosely down his back. Lastly, came the purse. Something that he saw girls go out with a lot. He'd picked a simple, small (and cheapest) purse from the magazine, that was a light beige in coloring. Even though his jacket had pockets, he still put his phone and wallet in it. He looked at himself in the mirror once more, and feigned the girly voice he'd been practicing while the wait for the clothes.

Crap, I sound convincing.

He slouched a little in depression; this was humiliating … but if I do it right, no one will ever know. Plus, the Blue Squares' pressure was getting to him. He wasn't used to being followed everywhere. And, he doubted that the Blue Squares would recognize him. He had no hips, and he was rather tall for a "girl," but he doubted they'd recognize him. I can do this … and if it works, then I can use this as an escape for other things.

He used the next half hour, nit picking over everything, making absolute certain he was convincing in appearance, voice, and walking in the shoes. Deciding that he probably couldn't do much more, he took a deep breath, and headed out the door.