Summery: AU Naruto gets himself in a confusing situation as he is dared to get close to Shino. With his past haunting him, he begins to have difficulties in just getting through life alone.

Ok, this is the first time I’ve tried Naruto, and he’s kinda hard. I seem to write a bit introverted, but I hope that I will come out of it the more I come along. Also, Naruto’s Kyuubi, and Gaara’s Shukaku are both duel personalities. And here the kick; it’s AU, so if it fits, I can get them to be real demons within a chapter. Depends on where my imagination leads me. I’ll introduce them in later chapters.

Pairings: Most likely Naruto-Gaara, Sasuke-OC, Lee-Sakura. Unknown with Kiba; probably Hinata or Shino. Votes are welcome.

Looking back on his actions, Naruto realized that his decision to cross dress that morning was not very well thought out. I mean, sure he could pull it off spectacularly with not even Iruka-sensei recognizing who he really was, but the boys hitting on him and jealous glances from girls were tedious.

Yet, even with all of that, it was fine. He pulled it off without a hitch and was on his way back to his dingy apartment after visiting the mall for fun when he was stopped for the millionth time that day by a hand on his shoulder.

Turning back while suppressing a sigh, he saw a boy about 18 or 19, his age, with wild brown hair and upside-down triangle tattoos under both eyes, each ending above his chin. He was met with a good natured grin, and Naruto naturally returned a bigger one. Looking down, Naruto saw a bright dog without a leash that was large enough to ride by the kid’s side.

“Hey miss, are you new around here?” The boy asked, looking friendly enough. Weighing his reaction, Naruto decided that it would be less of a hassle to say no. “Oh, no, I’ve been here for several years!” He exclaimed, raising his voice a few octaves, and trying not to sound screechy. “Why?”

The boy looked confused for a second and finally dropped his hand, letting it lay on top of his dog’s head. “Well, I have never seen you around here before. And none of my friends recognize you either.” He answer, sounding a bit confused while pointing out a table in an outside café.

Looking past the boy, Naruto spotted a pretty girl with pink hair, a shy looking one with lavender hair, and a bored looking guy with a messy ponytail. He couldn’t say that he remembered seeing any other them, apart from the fact that they looked familiar.

Placing his hand on his hips and rocking back slightly on his boot heels, he gave his fox-grin. “Well, if it’s any consolation, I don’t recognize any of y’all either.” He placed his arm behind his head in habit and asked good-naturedly, easily slipping back into his act, “So, who are you anyways? I’m Kitsuko.”

“Oh, I’m Inuzuka Kiba, and this is my good bubby Akamaru.” The dog gave a loud bark in greeting and Naruto laughed. He was suddenly feeling in good spirits and allowed Kiba to lead him towards the others.

“Ok, this is Haruno Sakura, Hyuuga Hinata, and Nara Shikamaru. We all go to the same college, Konoha University, for the day classes. Are you attending anywhere?” Naruto tried to act more like a lady and gave each a small nod and wave. He answered the question after thinking quickly and weighing his actions.

“Really? That’s awesome! I’ve been thinking of taking up classes there, but nothing has come up.” Putting a hand to his chin, he pretended to ponder. “Maybe that’s why we have never seen each other.” He gave a small chuckle and was asked to join them, which he did readily.

Enjoying himself thoroughly, he let his guard down and allowed himself become more at ease. They talked about everything from the teachers to the best restaurant. He found out that Sakura was an avid fan of Sasuke, and made it a point to not tell her of their scratchy friendship.

Eventually, they got around to Naruto’s life. He got the itching feeling to leave. “So, how long have you lived here Kitsuko?” asked Sakura, sipping her tea. Fixing on a smile, he replied, “I’ve been here since I was a kid. My foster parents moved me here when I was very young. I’ve moved around quite a bit since them.” He nearly chuckled as Shikamaru cleverly moved away from the parenting factor.

“Ah, so that solidifies that you have been here quite some time. What classes do you plan to take at the college?” Naruto struggled to keep the grin on. If they kept going, he was going to have to give some real information. He was hoping to just disappear and then show up as his true self some other day. No one was supposed to know about his day in drag.

“I will attend classes here and there, just gathering credits I guess.” He lied, forcing a believable laugh and stood to leave, throwing out an excuse of needing sleep for work. Just before he left, Kiba stood and stopped him again.

“Hey, Kitsuko, from what you told us, you like to meet new people and maybe a prank now and then, right?” Sensing a trap of some sort, he gave a slow nod, and quickly stopped, feeling some of the hair extensions starting to come loose. That could become a problem.

“Well,” Suddenly Naruto feared the task he was about to be given, and grudgingly realized that he was going to take the challenge, just because he hated passing them up. This could also become a problem. “I have a classmate in one of my biology classes, taught by Anko. You said that you were thinking of taking her class at night.” Receiving no answer, he continued, “His name is Shino, and I feel that he needs to get out of focusing only on class. I was wondering if you could help take his mind off of just school work.”

Naruto quickly looked up, no longer caring it his hair fell some more. “You want me to flirt, and/or date with some guy that I don’t even know? Do you think I’m easy?!” This was only his third time in his life dressing drag, but each time some man thought that he was either a prostitute (That was his mistake. Who knew that women really didn’t dress like that off of the TV set?), or easy (also his mistake. He had always watched girls flirt and must have over done it.)

He watched with satisfaction as Kiba’s face fell and the others started laughing. “Wh-What? No! I didn’t mean that at all! I just thought that you look like you would do that…” Realizing that his words sounded like he really was calling her easy, he flushed and tried to amend himself.

Finally taking pity on him, Naruto lost his serious expression and chuckled, telling the poor boy to calm down, thinking of a way to still take the bet… it sounded like a bit of fun. “Hey, hey calm down. I’m not one to just up and flirt for no reason, but my brother loves to make new friends. I’m sure he’ll take the challenge with gusto. But if he’s a jerk, the deal’s off. I’m not going to spend…allow him to spend months trying to get this guy to change his mind.”

Naruto twitched slightly inside as he caught his slip up; looking around quickly, he saw that no one had noticed it. Sakura spoke up from behind him. “Well, then I guess that your brother isn’t the guy we’re looking for. No one has broken this guys shell, but everyone has tried for at least two months. If you’re brother’s not up to it, then just say so and we’ll find…”

He turned around to see a barely conceivable smirk. He didn’t trust her, but bit the bait as anyways. “Fine. I’ll show you that he can hook this guy, no matter how long it will take. Better believe it!” This time he could see her victory grin. She was expecting that to happen.

After he got the class time and what the guy looked like, Naruto bid them goodbye and headed home. He was growing tired of the long combat boots and wasn’t used to feeling the short skirt, gypsy shirt, and bra. He wanted them off.