He sensed her presence the moment she walked into the bar. He was grateful for his training because she was suppressing her signature, which could have gotten past his abilities before he and Jiraiya left on their trip. It was difficult to manage the sense of excitement coursing through his body. He felt as if he had been hit with a surplus of new energy that needed to be used or expressed. Instead, he stayed where he was, nursing his drink. He couldn't even remember what it was, but the barkeep had recommended it as a distraction. Naruto had to admit that, for an out-of-the-way place, it was decorated quite nicely. It wasn't too bright nor too dark, with plenty of private tables. Even the bar had an impeccable wood finish. As he was trying to distract himself with the bar's design, he felt her chakra invade his system. He had to fight his natural impulse to reject the intrusion, his curiosity outweighing sound decision-making. Instead, he concentrated on the flow of his chakra, making sure the foreign presence wouldn't be disrupted but couldn't fully take hold. From one point of his body to the next, he felt his chakra flow increase slightly above its natural resting state.
She took the seat beside him and greeted him with a smile. It momentarily threw him off how much she looked like an older Haku, with the kimono and hair bun. He'd compliment her on her sources if it wouldn't ruin the game. The two made small talk while nursing their drinks. Naruto said his name was Hiru and claimed to be a writer. Itachi said her name was Miko and that she was in talent acquisition. Eventually, the drinks started being consumed a little faster, and the lies became a little closer to the truth. He found the back-and-forth exhilarating while simultaneously damning its necessity. They talked the night away until Miko stated she had to turn in for the night, then requested if Hiru would mind walking her back to her room for safety. He hesitated for only a moment, liquor and hope overriding initial concerns of a delayed setup. But he extended his sensory range just to be sure. He may be a little too drunk to fight, but he isn't too drunk to flee.
The walk back to her inn was mostly quiet, with her arms wrapped around his. There was a part of him, a part he rarely indulged, that lamented that this couldn't be a regular occurrence. He wished his life wasn't so antithetical to normalcy. He dutifully escorted her to her room, fully expecting this to be it until he heard her say, "Would you like to come in?".
Most of him screamed "NO!". Not just his shinobi instincts but the little part of self-awareness his drunken mind had held onto realized that if this goes where he thinks it could, it would be utterly embarrassing. He doesn't know what to do with a woman, well, he has some idea thanks to Jiraiya, but he'd be entirely too nervous to even remotely pull that stuff off. This is Itachi, despite what people say; your first time shouldn't be with the one you love. That's like your first shinobi battle being with a freaking Kage. You have to get some experience under your belt, perfect your moves. While much of Naruto was slipping into an uncharacteristic bout of crippling insecurity, another part of him spoke up, "You got this." That voice that let him stare down Zabuza, that let him beat Gaara and challenge Tsunade. Oh, confident Naruto was in the building. And he seemed to be supercharged by the liquor in his system because he was sounding extra smooth and commanding tonight. Like it wanted to sell him some Colt 45 in Cloud City smooth. "Just take it slow and let the night go where it goes. Besides, this won't be the first time you tussled with an S-Rank kunoichi." He listened to that voice.
Naruto gave a response, one he still isn't sure about, but it was in the affirmative, and he hoped it was cool. Itachi wasted no time once the door was shut, kissing him aggressively, and he returned her gesture with equal fervor. It escalated from there, Naruto's unnatural belief in himself, high stamina, and undesired lectures from Jiraiya making up for his lack of experience.
Even while wrapped up in their activities, he couldn't help but note the bittersweetness of it all. How he longed to see her face and hear her real voice, to not have to do this behind a hastily crafted fiction. Was it really too much to ask that he be granted a moment of happiness with no strings attached? He supposed it was since it never happened, every benefit came with a cost. Hearing her moan and feeling her breath on his neck sent a chill down his spine. The rest of it was almost too much to even comprehend. They fell asleep in each other's arms, both silently thankful for the moment they got to share. She was gone by morning with no trace she had been there the night before. In the quiet of the morning, Naruto was able to think.
In the past, thoughts of the short time Itachi was in his life warmed his heart. While he missed her terribly, he was always able to fill that hole with wishing she was well or hoping she was safe. Also, his focus on becoming a respectable and skilled shinobi, as was her example, had kept him occupied.