Anko's eyes bore holes into Naruto. He couldn't really say he'd thought any differently about her.
He couldn't really say that he'd even thought much about her at all in the context of dating or fucking before tonight. In fact, he really hadn't had that on his mind when he sat down at her table, because he had just wanted to get away from the Ino and Kiba freak show. She didn't look Naruto in the face anymore. Anko let her eyes drop to her drink. She watched it with great interest, stirring what little was left with her tiny straw.
There was a glint in her eyes which said she was curious, but also very suspicious of him. He's always been a loner since he dropped out of the ANBU. He waggled his eyebrows and leaned forward onto the table, almost spilling the pitcher of sake. I'll just read the classified files if you don't tell me. I'm sure I could find out some juicy gossip from those. He was laughing now as Anko turned very red. Anko shook her head as one of her hands found purchase on her throbbing temple. She paused for a moment, and then started in on a rather humorous story about how she used to be able to identify Kakashi in his ANBU uniform without even seeing his dog-mask.
This was because he stuffed his Icha Icha down into his tight, spandex uniform during extended missions when they didn't carry packs. Naruto got a kick out of hearing that and wanted Anko to tell another. As she shared several more stories, Naruto found himself starting to enjoy Anko's company quite a bit. A few more drinks and the two of them bid each other farewell for the evening. Naruto left the bar not accomplishing what he came to do, but feeling rather happy with the outcome of the night anyway.
The next night, Naruto got wrangled into drinking with a very different group of people than he ever had before. Anko had found him early in the morning in the mission office and invited him to join her in the bar again.

Genma and Raidou seemed to allow Naruto to join their odd little fold of older jounin without any questions. Shizune seemed very embarrassed that Naruto was there. A few of the others had worked with Naruto and found him pleasant enough, so they didn't take issue with the younger ninja drinking with them. When the night began winding down, Naruto waved goodbye to all of them.
Doing the gentlemanly thing, he walked Anko home, much to her disdain. When they got to the door of her apartment complex, Naruto smiled and wished her goodnight. He started to walk away when Anko shouted to him, "You aren't trying to woo me or anything, are you? The night that followed was exactly the same. It started with more drinking with Anko's friends, then Naruto walked her home, but this time when he got to her apartment, Naruto's hand reached out and squeezed hers gently.
Anko pulled her arm away so quickly that it seemed like Naruto's sweet gesture had hurt her. Good thing Naruto was persistent.
He was starting to take a real liking to this spunky woman. She was so different than he'd assumed she'd be. He knew that if she really didn't want him to be there, she'd tell him to leave her alone, not goodnight. Naruto had a mission the following day, so he wasn't able to go out with Anko again.
When he returned three days later, after completing the assignment, he bumped into her at the ramen stand. Naruto swore he could see the faintest of blushes on this hardassed woman's cheeks. He didn't say anything about it, because he knew she'd rip him a new one if he did. She laughed, "You get to my age as a jounin and you decide to live life to the fullest, Naruto.
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I know I'm just glad to be alive. Anko really did blush when Naruto replied, "I'm glad you're alive too, Anko. I'll be there with bells on. Naruto didn't wear bells, but he arrived at the bar at the designated time. They had a lot of fun, drinking and laughing and telling stories. There was a drinking game or two, and Naruto couldn't help but get a little tipsy after attempting to keep up with Genma and Raidou for a short while. Just like it had the previous times, as the night wound down, Naruto and Anko found themselves saying goodbye to the rest of the crowd.
Tonight Anko didn't chastise Naruto for wanting to walk her home. This time she seemed much more open to it. When the two of them reached her complex, Naruto reached forward and tucked a bit of hair which had fallen in front of Anko's face back behind her ear. Anko seemed very flustered by Naruto's question, especially since he was very much invading her personal space by touching her hair and smiling at her with that handsome grin of his. All that while less than an arm's length away.
Anko glared at him and narrowed her eyes into angry slits. Naruto touched her hair softly again, and ran his fingers very gently from her scalp, downward as he combed them through the silky purple strands. He liked how she wore it down when she wasn't on duty. It made her look very pretty, and much softer. Naruto appreciated it because when she was off duty Anko became an approachable human being, or more accurately, a woman and person who he had accidentally started to fall for. Anko leaned forward a bit, stopping so that her face was right next to Naruto's.
Her lips were millimeters from touching his, and she very quietly murmured, "You little bastard…" again. Naruto could feel the soft puff of air that accompanied each word. He moved just a little and their lips brushed. He sensed as Anko shivered. He watched as she closed her eyes. Most importantly, Naruto felt as she solidified the presence of her lips against his. It was such a gentle kiss, but so addictive. Naruto knew he wanted more. He wanted to touch her more and kiss her more.
Most of all, he just wanted to be with her more. It was Anko's way of protecting herself.
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It was familiar, and Naruto wanted to show her that she didn't have to hide herself around him. The more he got to know her, the more Naruto found himself loving how she was brash and honest, just like him. He felt as if he'd found something familiar in Anko. Spending time with her was more comforting than he really cared to admit. Anko broke the kiss. He might have thought it was a bad thing if she hadn't balled her fingers into the front of his jacket, bringing his body closer to hers.
She didn't look him in the face as she said this. In fact, Naruto couldn't believe how timid she was being. He couldn't find his voice, even though he desperately wanted to say yes. That explained a lot. Naruto might have tried to be more gentlemanly by suggesting they wait until she was completely comfortable with the idea of them being intimate, but it had been quite some time for him as well.
This time as they kissed their bodies began to come together. Anko stopped being quite so shy, and kissed back hard, plunging her tongue into Naruto's mouth.
Naruto accepted it and returned the motion with an equal ferocity. He sighed into the kiss, as the desire between them was very nearly palpable. Anko reached back and kicked open her apartment door with her foot. As soon as the two of them were inside it was a flurry of mouths, clothing, and appendages flying every which way. More than once, in their frantic rush to get undressed, Anko and Naruto found their arms and legs tangled together. It might have been clumsy, but neither person noticed.
It just felt nice to have one another, to have someone who actually cared. Having some pleasurable human contact didn't hurt the situation either. Naruto tugged Anko's mesh top up and over her head, and as soon as the last barrier was gone he leaned down and drew one of her bountiful breasts into his mouth. He swiped a tongue over Anko's hardening nipple and it caused her to vocalize her pleasure with a long, drawn out moan.
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Anko's fingers gripped Naruto's spiky, blond locks, tugging them tightly as he bit and licked and nibbled her breast, first the right one, then the left.