AU: Hey guys! Sorry this is so terribly late, but you know school. I haven't given up any story, just been incredibly, ridiculously busy. Also I split this into two parts cause it would've been too long xD

Naruto did up the last button, leaving one undone at the top, and ran his hands around the collar- making sure it was all folded down. He looked up into the mirror expectantly and instantly hated it. He stared at his reflection, hands still wrapped around the collar, while he was filled to the brim with frustration and anger.

He sucked in his cheeks, taking a deep breathe, and began the tedious of process of unbuttoning the red cotton shirt. He stared blankly into the mirror as his movements became more vicious-he was now ripping at the buttons, pulling the fabric apart so roughly a voice in the back of his head worried him about ripping the shirt.

Reaching the last button, Naruto quickly tore the shirt off, not able to get out of it fast enough. He balled it up in his hands and threw it down on the ground. Then, without missing a beat, he grabbed the back of his white undershirt and pulled it forward and over his head. He threw it down on top of the red shirt and stood there for a few seconds, panting.

The anger was now beginning to fade, leaving him exhausted and feeling foolish, but still just as frustrated as before. He tightened his jaw, eyebrows furrowing, as he stared down at the shirts by his feet.

"What the fuck am I doing?" He asked quietly; bring a hand up to rub his forehead. After giving his forehead a quick rub, his hand slid down, and Naruto rested his cheek into the palm of his hand- eyes closed.

"Yes, what are you doing?" A curious voice floated in, taking Naruto completely by surprise.

Naruto looked up, eyes going to the mirror. Itachi's reflection stared back at him curiously then quietly surveyed the room. He looked back to Naruto, inquisitively, then his eyes traveled down Naruto's exposed torso and sharpened with lust. Naruto averted his eyes, wrapping his arms around his torso defensively.

Naruto turned slightly towards Itachi, "Nothing."

Itachi cocked an eyebrow at Naruto in disbelief, then looked back to the piles of clothes scattered all over the room. He gestured to the mess, looking at Naruto pointedly,

"Playing dress-up?"

Naruto's eyes flickered to where Itachi was gesturing, his mouth thinning into a defensive line. He turned around, aware of Itachi's eyes on his naked back and stared into the mirror- disgruntled eyes trailing over his features with disappointment.

He finally shrugged, swallowing, "They weren't working."

Naruto could tell that Itachi wasn't pleased by this answer. Stepping into the room, Itachi stared at Naruto, unabashed, with calculating eyes. Naruto avoided Itachi's gaze, instead focusing on his reflection in the mirror. He could tell that Itachi was growing concerned and he didn't blame him, but Naruto couldn't deal with that right now. Not when he himself was feeling so conflicted and frustrated.

"Well you're being quiet." Itachi pointed out, sticking his hands in his pockets as he sauntered confidently across the room. Naruto didn't know what to say to that, what could he say? So he kept quiet.

Greeting Naruto's silence with another nod, Itachi turned around, meeting Naruto's eyes with his in the mirror and sat on the bed. Itachi looked away, rubbing his hands idly together.

"The date?" He guessed casually, eyes skimming over the messy room then to Naruto.

Itachi watched as Naruto froze and his usually happy form seemed to wilt even more- if that was possible. He furrowed his eyebrows, his level of concern growing with every silent second.

He leaned forwards, resting his elbows on his thighs, "So are you gonna tell me what's wrong or do I have to put you on suicide watch?"

Naruto looked over at him, surprised, his eyebrows raised, blue eyes bright for the first time in the whole conversation- he looked like Naruto, which put Itachi somewhat at ease. Then Naruto's eyes narrowed to half-mast and he huffed out a laugh. He looked back to Itachi- eyes searching, trying to figure him out, to see if he could be trusted- and then Naruto slowly began to unwind his arms from around his torso, running a hand through his hair.

Naruto shrugged, eyes glued to the mirror, "I don't…I don't know. It's just…."

Itachi watched him intently, waiting for Naruto to continue.

A tan hand fisted in golden hair, "What if I'm making a huge mistake."

Naruto finally spit it out; he looked at Itachi as he said this, taking his hand from his hair.

"What if I am completely making a huge mistake? What if I'm not gay? I don't- I don't feel gay! I just feel….nauseous, full of dread, and more nervous than I've ever been in my life. What if this goes horribly and our relationship is ruined!?" The flood gates had burst and now Naruto was spewing all of his worries with no way to stop, "And not only do I feel like I'm going to vomit up everything that I've ever eaten in my life, I can't find anything to wear to the dumb thing! And that sounds so girly, I know, but it's true! I can't find anything to wear and it…it's just making just everything worse."

Itachi leaned back on his hands, looking at Naruto, the corner of his mouth twisted up in the famous Uchiha smirk,

"Well if you go like that," Itachi nodded his head towards Naruto, "I guarantee Sasuke will love it."

Whatever Naruto was about to say was stopped in its tracks at that comment. Naruto looked at Itachi for a few seconds, confused, before understanding. Naruto's hand began to caress his naked stomach, fingers subconsciously tracing the tattoo that swirled around his belly button as he laughed. His laughter trailed off quickly and soon the silence was back. Itachi, who hadn't taken his eyes off from the floor the entire time, now looked up at Naruto seriously.

"You're terrified." He said decidedly.

Naruto nodded back, looking relieved, "Yeah I a-"

"But not of what you think," Itachi interrupted, holding up a hand and standing up, "You're not scared the date will go awfully. You're terrified that it'll go great." Itachi stopped for a few seconds, letting that sink in, "You're scared to feel the love that you're scared that Sasuke feels for you. But you're also hesitant because of how your last relationship ended. But you can't go in there like this or it'll act like a contagious disease and these unsure feelings will spread to Sasuke."

Naruto had begun to withdraw back into his defensive pose from earlier- arms wrapping around his torso, back hunched. Then, Itachi, without missing a beat, bent over and grabbed the red button-down shirt off the floor by Naruto's feet. He stood up, holding the shirt out in front of him, checking it for wrinkles. After deeming it satisfactory Itachi nodded, stepping over to Naruto and began the process of dressing the blonde.

Naruto shook his head, confused, mouth opening and closing as he searched for something to say.

"What- are you dressing me?" He asked his voice incredulous.

"As much as Sasuke would like the outfit that you've picked out, I'm afraid it's not appropriate for a first date." Itachi answered without so much as a glance up at Naruto.

Naruto stepped backwards, in a feeble attempt to escape Itachi. Itachi simply followed him, stepping forward. Naruto sighed, resigned to standing still.

"But my undershirt." Naruto protested, gesturing to the white shirt that Itachi was standing on.

Itachi gave the fabric beneath his feet an unimpressed look, then kicked it away.

"Showing a little skin goes a long way. Trust me, what glimpses of your skin Sasuke can get, he'll savor them." Itachi said quietly, fingers tapping Naruto's exposed collarbone.

They fell silent-Itachi busy with his work, Naruto with his thoughts. At the mere mention of the name, his head was flooded with images of Sasuke- much like it had been when Itachi had first kissed him. There had been a time where this would have made him uncomfortable and confused, but for some reason right now, he didn't mind them so much.

He lifted his arms, helping Itachi with the job of getting his arms in the sleeves. Itachi was standing so close that the fabric of his shirt brushed Naruto's stomach. The silence between them was comfortable and in it, Naruto found himself not only thinking of Sasuke, but of his failed marriage. He had often been kept awake by a certain question and right now he was bursting to ask Itachi.

'Wait, don't ask it. It's weird and personal and he'll think you're craz-'

"Where do you think I went wrong?" The words came ripping out of him.

He blinked, looking at Itachi, mirroring his expression of shock. He struggled for an apology, his mouth hanging open uselessly. Then Itachi was looking at him with such a look of sadness that Naruto's heart hurt.

"I can't tell you that." Itachi said and Naruto was amazed that the raven even knew he was talking about his marriage, "but I can tell you one thing."

Itachi pulled the shirt up over Naruto's shoulder, biting his cheek; he had never expected the blonde to feel this small in his arms. It was difficult to not touch him more. He went to work on the buttons, deciding whether or not to leave some at the top undone. He stepped back to look at Naruto.

"Tell me, what was the last thing you learned about Sakura while you guys were happy and married? It can be anything; a scar you never noticed or a particular way she ate something."

Itachi stepped forward, buttoning the top button with ease, and then stepping back again.

Naruto looked down, brows furrowing with concentration. After a few minutes, his chest went cold, his mind frantic and confused.

He couldn't think of anything. Not a damned thing.

Itachi stepped back, undoing the top button, then ran his hands down the front of the shirt, smoothing out any wrinkles (and come on, when was the next time he was going to be able to touch the blonde like this without a huge fight?).

"I can't tell you what went wrong in your marriage, but, I do know that you stop learning things about people when you lose interest in them." Itachi said straightening up, looking Naruto clearly in the face.

Naruto's face was the epitome of bewilderment and disbelief. Itachi looked at him for a few seconds before smirking.

"Go put on some cologne, that blue necklace you wear, and a nice watch- if you have one." Itachi instructed, stepping around the frozen blonde and walking to the door.

Itachi shot a glance over his shoulder as he neared the door and upon seeing Naruto still frozen in place, Itachi dove forwards, giving Naruto's ass a hard smack- drawing a startled, indignant shriek from said blonde.

"Chop chop, Uzumaki. You've got a boy to impress."

Naruto sat on the couch, elbows resting on his knees. His chest felt so tight that he could barely breathe. Somewhere in the house, a clock was loudly ticking-each individual tick echoed down the quiet hallways, adding to Naruto's anxiety.

'Holy fuck, what the fuck!?' Naruto thought, frantically, 'What the actual fuck was I thinking? I can't fucking do this!"

The entire house seemed to be holding it's breathe; there were none of the usual settling noises of the house nor were there any clicking of the dogs nails on the floor. Really, the only thing Naruto could hear was this:

"Who could you love, me or Sasuke?"

Itachi's voice echoed in his head. By the third time it repeated, Naruto was on the verge of hyperventilation.

'Jesus Christ, I am an idiot!' He thought, squeezing his eyes shut and giving himself a hard smack on the forehead, 'I definitely couldn't love Itachi- but what the hell?! I can't love Sasuke!'

He opened his eyes, resting his chin on his fist- disgruntled. 'I mean…..could I?'

Slowly- unlike before where the memories had seemingly popped into his head- images of Sasuke began to slowly seep into his mind. Also, little details about the stoic man, like how he hated grapes and only liked to write in pen. Suddenly, a hazy memory from the night he and Sasuke had gotten drunk appeared. Naruto could just vaguely see himself lying in Sasuke's lap, Sasuke looking down at him- cheeks and the tip of his white nose pink- eyes wide with surprise.

Naruto bit the inside of his cheeks softly, his heart growing strangely warm, 'Could I?'

He gave a loud sigh, falling back onto the sofa, arms crossed over his eyes.

"I don't know." He moaned.

Then, suddenly, there was a knock on the door. Naruto's anxiety sky rocketed from a seven to an eleven in about a millisecond. He shot up and off the couch, racing over to the archway that connected the living room to the front hallway and peaked out into the hallway cautiously. All he could see was the smudged silhouette of Sasuke in the front door's glass but the sight alone was enough to send him spiraling into a full nervous breakdown.

Naruto spun around, back facing the archway, and for a few minutes did a panicked dance- twisting around, hands groping the air.

'Oh my fuck, holy shit, what the fuck do I do!?' He thought frantically, hopping in place, bursting with anxious energy, 'Do I pretend like I'm not here or…!?'

But that could never be an option; that would be cruel to Sasuke. Sasuke was his friend and though Naruto might not know what his feelings were about this situation- Sasuke sure did. Naruto closed his eyes and took a deep breathe, 'I can do this'.

The front door opened, Naruto heard Sasuke step in, closing the door behind him. Naruto furrowed his brows, he was so nervous he was actually shaking. He clenched his hands into fists, took one last, deep breathe and then without giving himself time to think- he stepped out into the hallway.

Naruto stood, fists clenched, eyes closed, as if bracing himself against an invisible impact. His heart was thundering in his ears, his stomach in his throat.

"…Naruto?" Sasuke's voice called out, sounding confused.

Just hearing Sasuke's voice, for some reason, took away some of Naruto's fright. Slowly, he opened his eyes, staring down at the floor for a few seconds before travelling up Sasuke's long body. Sasuke was wearing a casual sneaker, his long legs emphasized in his dark jeans. Naruto swallowed shallowly as he looked up Sasuke's long torso, then he looked at Sasuke's face.

And, for some reason, he was instantly breathless.

Just from the body, Naruto could tell that Sasuke looked good, but seeing his face just completed the picture. Sasuke's normally neat hair was styled the same, only now it had more of a rough, tussled look. Naruto had never noticed how narrowed and feline Sasuke's eyes were; immediately the phrase "bedroom eyes" popped into his head and he licked his lips subconsciously. White teeth glinted underneath Sasuke's growing smirk and Naruto found himself looking, captivated, at the sight of the pink tongue that darted out to wet Sasuke's lips.

A sudden, possessive, smug feeling took over as he looked at Sasuke. Right now Sasuke was his. He was dressed up for him, here for him, and, for at least this moment, Sasuke was his.

Sasuke smirked at him, raising his head, looking down at Naruto appraisingly.

"You see something you like?" He asked, teasingly, subconsciously biting his lip.

Naruto snapped back to reality, bristling at the cocky question. He turned away, crossing his arms, glaring at Sasuke out of the corner of his eyes.

"Nope."

Sasuke cocked an eyebrow, "Might wanna put your eyes back in your head before saying that."

"Well you might wanna get all the dick out of your personality."

"Unfortunately, I don't have any dick in my personality, but I do have plenty in my pants if you would like to see."

Naruto grimaced, shooting Sasuke a disgusted look, "No! Why the fuck would I wanna see your dick?"

Sasuke shrugged, smirk growing bigger, "I don't know, you tell me, I came here to be a gentleman and take you on a date but you just started talking about my dick."

Naruto's eyes widened then narrowed to a glare, he stepped forward, pointing at Sasuke, "I did NOT start talking about your dick, I was talking about your personality and how much of a dick you are!"

Sasuke stepped forward, sending Naruto a gust of his cologne. The smell made his mouth water.

"You know, I never expected you to be the first one in this relationship to bring up my dick being in something."

Naruto's jaw dropped, face burning. He stepped forward, giving Sasuke a hard punch on the chest, "In your personality! You're a dick! That's what I'm saying!"

Then Naruto realized how close they were. There was maybe six inches between them. Then, as his brain began to panic, he realized that they'd been flirting! Actually flirting! He looked up, shocked, at Sasuke, who seemed to know what he was thinking and had backed up a step. Naruto looked back down, clearing his throat. After a few seconds, he looked sideways at Sasuke.

"So?"

Sasuke's head snapped towards him, "So what?"

Naruto grinned, placing his hands behind his head, "Where are you taking me?"

Sasuke's smirk returned, he reached into his pocket, took out his keys and tossed them up in the air, catching them in one smooth movement.

"That's for you to decide."

Naruto didn't know anything about being gay or dating a guy but he did know that in no way, shape, or form, did he want to be treated like a girl. He realized this as they walked to Sasuke's car. The passenger's car door caught his eye,

'If he opens the door for me…' Naruto thought, glancing stiffly at Sasuke who was walking beside him, keys clutched in his hand.

When they came to the car Sasuke stopped beside Naruto, raising his hand with the keys in it. Naruto looked on in horror, 'Don't you do it, don't you da-'

Sasuke pressed a button, unlocking the car, then walked over to the driver's side and swung open the door. As he placed one foot in the car, Sasuke stopped, looking over to Naruto who hadn't made a move towards the door.

"Oh…" Sasuke said, a look of realization dawning on his face. He quickly took his leg out of the car, "Did you want me to open the door for you?"

Naruto blanched, shaking his head, "No, nooo."

Sasuke stared at him, one hand resting on the roof of the car, "then what?"

Naruto opened his mouth to respond, and then closed it again, suddenly embarrassed. He glanced at the car door and contemplated just getting in, but with Sasuke staring at him, Naruto found he couldn't move a single muscle.

"It wasn't that I wanted you to, I was just…scared that you would." Naruto said, twisting his hands, looking at Sasuke, hoping that made sense.

Sasuke huffed out a laugh, looking at Naruto puzzled. Naruto's face flamed, he looked down at his shoes then back up again.

"I don't know anything about…..this," Naruto said, gesturing to him and Sasuke, "But I just didn't-don't- want to be treated like a girl."

Sasuke stared at him, and for a few seconds Naruto was actually petrified that he was gonna laugh. He was hit with another thought; Sasuke was so experienced- with men and women. Naruto had been with women before, knew how to act, what to say, how to please them. But with Sasuke….Naruto was a virgin. A clueless virgin. The thought was terrifying.

Then Sasuke smirked, pointedly checking Naruto out.

"Don't worry, Uzumaki," he said, stepping into the car once again, "I know you're all man."