First Time Offender - a chronology of Sakura's 'firsts' during the 2.5 year time skip

Chapter 1: A (Fake) Date

"I'm fat."

"So?" Sakura let out a yawn that, while satisfying, was rather lacking in tact.

"You're not even looking!"

It was true. Sakura might have been interested, or at least amused, if there had been any validity to Ino's complaints, but she highly doubted her friend's slim figure had altered dramatically in the past five minutes.

"Sakura."

Sakura forced her eyes away from the medical scrolls she was thumbing through. And abruptly burst into a fit of giggles that would have done any academy level kunoichi proud.

"What are you wearing?" Or, more accurately, not wearing.

A scowl twisted Ino's features as she adjusted the ill-fitting scrap of fabric pasted over her chest. The skirt stretched over her butt was experiencing similar difficulties, though Sakura wisely refrained from commenting.

"See? I'm a complete pig." Ino gestured to her perfectly flat stomach as if to emphasize her point. "Your clothes don't even fit me."

Ouch. Sakura rolled her eyes at the implied insult, mollified by the knowledge that Ino was experiencing a crisis of epic proportions. Her proportions, to be exact.

"It was bound to happen eventually," Sakura pointed out mildly, grinning behind the cream-coloured parchment concealing her expression. "You, ahem, growing into your name, I mean."

"Very funny." Ino's bottom lip wobbled in a rare concession of sincere anxiety, although she tried to hide it by flipping her long ponytail of blonde hair over her shoulder.

Ino couldn't be seriously concerned. Could she? Just in case, Sakura stifled an exasperated sigh. "You're not fat." There. That was concise, truthful, and difficult to misunderstand. "Unfortunately," she tacked on as an afterthought.

When the blonde continued to look skeptical (and a little sad, what with her smushed ensemble), Sakura decided pictorial evidence was in order.

"See this?" With a huff that was perhaps a little too exaggerated than standing from a chair warranted, Sakura snatched a frame from her dresser. Ino nodded, brow furrowing in a get-to-the-point sort of way that was much more familiar than the wobbling lip.

"It's me and you, right?"

"Funny and smart. Konoha really lucked out with you, didn't they?"

"Shut up." If Ino was being sarcastic, the situation couldn't be that dire. Still: "The point is that you" – Sakura tapped the grinning blonde girl in the picture – "are curvy, whereas I"– her finger drifted over to rest on a 2-dimensional, pink-haired figure – "have a build that's more…athletic." Flat. "Of course my clothes are going to be a bit tight on you; I mean, pig is debatable, but you're not an elephant. Yet, anyway."

There was a dangerous glint in Ino's eye when she flounced away to Sakura's closet to change. "So the problem isn't that I'm too fat, it's that you have no boobs and a tiny ass."

I wouldn't have put it quite like that, but…"Sure, Ino, whatever."

Truthfully, Sakura was just happy to have eluded a potential Ino meltdown. Now that she thought about it, the blonde had been acting weird all day: messing with her hair constantly, fiddling, insisting they ransack Sakura's (pitifully lacklustre) closet. Curiosity piqued, Sakura abandoned the anatomy diagram she'd been about to resume studying.

"Why the sudden attack of insecurity?"

"No reason." Ino's voice was just a little too coy to assuage Sakura's suspicions.

"Uh-huh." Sakura leaped from her chair and flung open the closet door in one fluid motion. "Spill."

"Do you mind?" Ino snapped. "I'm naked." That wasn't precisely accurate, but Sakura refused to be distracted by the fact that a bra and spandex shorts didn't constitute nudity.

"Is it a boy?"

"None of your business," Ino said, the smug smile in her voice revealing more than the words themselves.

Sakura grinned as she leaned her shoulder against the door jam. She wasn't worried; Ino might make people work for the information, but she was a notorious gossip.

A few more moments of heavy silence and she cracked like a twig. "Okay, fine. But only if you do me one itty-bitty favour."

Oh no. Knowing she would regret it later, Sakura asked, "And that would be…?"

"Nope." Ino waggled her finger, smirking. "Sorry, forehead, that's part of the deal. I'll tell you about my mystery man, but you can't know what the favour is until you've agreed to do it."

"That's ridiculous. We're fifteen, not five; just tell me what it is."

Ino mimicked zipping up her mouth and throwing away the key.

"Ugh." Sakura made a noise halfway between a snort and a growl before grumbling her agreement.

"Don't laugh, but..." Ino's cheeks puffed as if the 'secret' was forcing itself out of her. "I've got a date with Chōji."

"Chōji?" Sakura blinked. That, she had not been expecting.

"What?" Ino demanded, crossing her arms in a manner that mirrored the defensive tone of her voice. "Chōji's nice."

"He is nice," Sakura agreed. She'd just never thought 'niceness' was the quality Ino most looked for in a prospective boyfriend. "But…what about Sasuke-kun?"

"What about him?" Ino rolled her eyes. "I'm not going to save myself for him like some wilting virgin."

A smirk worked its way over Sakura's mild smile despite her best intentions. "It's about time you conceded defeat."

"Not even close, forehead." Ino stuck her tongue out before turning to rifle through the heap of clothes she'd displaced. "But there's no reason I can't get in a little practice while he's gone."

Practice, huh? Having anticipated such a response, Sakura snorted. "When does this 'practice' start?"

Ino shrugged as if this information wasn't really important. "Chōji should be here in" – she paused to glance at the clock beside Sakura's desk – "half-an-hour. Oh my God. I only have thirty minutes to make myself gorgeous!"

Ino whirled out of the closet, still only half-dressed, in a flurry of clothes and a high heel that seemed determined to brain Sakura in the head.

"Don't mind me," Sakura mumbled. Then, louder, "Who instigated this whole thing?" It was the most delicate way she could think of to ask, 'How the hell did this happen?'

"No time for questions, I'm concentrating." On applying eyeliner, Sakura deduced upon quickly peeking in the bathroom.

"I just can't see Chōji asking a girl out, is all. Wasn't it awkward?"

"Not at all," Ino said hurriedly. "It was romantic and wonderful, okay? Now scram – I've got to find an outfit that'll fit over my gigantic ass."

So much for the quick recovery of Ino's self-esteem. Sakura eyed the pile of clothes on the bathroom floor dubiously. "Good luck," she said as the door was slammed in her face.

Only when the doorbell rang did Sakura think to wonder why Ino hadn't gotten Chōji to pick her up at the Yamanaka residence. Or what the 'itty-bitty favour' was and why Ino had conspicuously neglected to elaborate on what it entailed.

"Can you answer the door?" Ino called from the bathroom, voice a little frantic. "Please."

"I guess."

Sakura stretched, the joints in her neck popping, as she descended the stairs. She half-expected to see Chōji dressed in a suit and toting a bouquet of red roses or something equally ridiculous when she opened the door. With mild disappointment, she registered that he was wearing his usual gear, complete with the armour characteristic of the Akimichi clan. A crinkled bag of barbeque chips seemed to be his only adornment, which hardly seemed romantic.

"Hey, Chōji," she greeted politely. "Ino's upstairs."

"Hi, Sakura. I like your pyjamas." He would. The top half featured an ever-so-fashionable motif of rice balls.

"Sakura."

"Um." Sakura peered around Chōji at his seeming echo, a shadowed figure she hadn't immediately noticed. "Shikamaru? What are you doing here?"

"Same thing as you, I imagine." The lazy genius's drawl was not the least bit informative.

"Studying for a medical examination?"

"Not quite." Shikamaru directed his eyes skyward, as if seeking divine intervention, as he said, "Ino –"

"Is here!" As if summoned, the blond appeared behind Sakura's shoulder, radiant in a lilac dress Sakura's mother had bought on a whim. It had always been a little loose on Sakura, but Ino certainly filled it out. "How do I look, Chōji?" she purred, shooting Shikamaru a shut-up look out of the corner of her eye.

"Er, you look…nice." Nice. There was that word again. "Want a chip?" Ino didn't – or chose not to – notice her date's lack of articulation as she barrelled forward and linked their arms. To his credit, a touch of colour tinged Chōji's cheeks and he seemed to have a difficult time swallowing the mouthful he'd been chewing.

Sakura quirked an eyebrow at Shikamaru, who was watching this exchange with what appeared to be a mixture of irritation and resigned amusement. "Are you supposed to be their chaperone or something?"

Obviously anticipating an interruption, Shikamaru slanted his drooping eyes in Ino's direction.

"Don't be silly, Sakura," Ino began in a voice that was far too sugary-sweet not to have unfavourable consequences. "You were just saying how lonely you were without a team to spend time with."

"I was?"

"Sure." The beseeching look in Ino's eyes might have been more convincing if she hadn't been mouthing the word favour. "It'll be like a double-date or something."

Whoa. Sakura's intuition twitched in a way that wasn't altogether pleasant.

"I'm not even dressed," she said slowly, waffling for time as she decided on the best way to handle this particular situation.

"You look great," Ino insisted.

Right. The situation must be serious if Ino's resorted to compliments.

"You look fine, Sakura," Shikamaru said without enthusiasm. "Let's just get this over with before Ino dies from hyperventilation."

With flattery like that, how could a girl refuse? Relatively easily, Sakura found, but just as she opened her mouth to decline as politely as possible, Ino grabbed her arm in a grip that brought to mind five well-manicured senbon needles cutting into her flesh.

"I forgot something inside," she said, disentangling herself from Chōji. "Come help me look, Sakura?" Not a question, regardless of intonation.

"Double-date?" Sakura exclaimed once she'd been hauled up to her room.

"You owe me one favour of my choosing, and this is it." Ino sighed exasperatedly. "Can't you just come out with us and not be difficult?"

Apparently not. "I thought I'd have to take your shift at the flower shop or something. Not – this! Why didn't you just tell me beforehand?"

Belatedly, it occurred to Sakura that she was making a bigger deal of the situation than was really necessary, but she shoved the thought aside.

Ino flopped gracefully onto Sakura's bed, frowning at the ceiling. "I was hoping I wouldn't have to say this…but, ugh, here goes: you need to have some fun," she declared, before letting out a huff of sound that was almost wistful. "Naruto's been gone for more than two years now, and who knows what Sasuke-kun's doing. I'm not saying you should give up on them coming home, obviously – but I don't see why you can't experiment a little, and, I don't know, have some adventures of your own, while they're away."

Sakura was just starting to feel a twinge of something, irritation at her friend butting into her life, maybe, or possibly even a nostalgic sort of sentimentality that she cared enough to do so, when Ino ruined it by adding, "You're lack of normal teenage behaviour is becoming pathetic, forehead, seriously."

"I have adventures," Sakura muttered defensively, heart stuttering at the mention of her absentee teammates.

"Yeah. In the hospital. On missions. The adventures I'm talking about are more likely to occur…" Ino trailed off, but her implication was made clear by the hand she swept out to indicate Sakura's bedroom.

"You're not implying I should 'experiment' with –" Sakura nearly choked on the name – "Shikamaru?"

The look of disgust on Ino's face was almost comical. "No, ew, of course not. Shikamaru wouldn't notice a girl unless she had a Shogi set strapped to her boobs. He's just, er, a means to an end."

"Okay." That was a bit extreme, but Sakura was nonetheless relieved. "Who, then? I'm not just going to walk up to a random civilian and ask him to be my sex slave."

"Sakura!" The scandalized note in Ino's voice was highly exaggerated, as was her smirk. "I didn't say anything about sex."

Sakura rolled her eyes at this. "I was just kidding."

And she had been. Mostly. It wasn't that the idea of waiting for Sasuke wasn't appealing, and she'd always be in love with him. Still, there was no reason, as Ino said, that she couldn't have a little fun before dedicating herself to attaining what – and who – she'd always imagined as her future.

As for how much 'fun' she was willing to have…that remained to be seen.

"Are you sure you're not just nervous about being alone with Chōji?"

Ino flipped her hair over her shoulder. "Me, nervous? I don't think so. But Shikamaru's got that nerdy slacker thing going on. Are sure you'll be able to restrain yourself?"

Sakura decided Ino had diverted the attention from herself just a little too fast. And was that a blush? Surely not. "I'll do my best."

"So you'll come? Good; I knew you would." Right.

"So," Sakura said, grabbing a jacket from her closet. The embarrassment of going out with messy hair and wearing food-embellished pyjamas would be quite enough without freezing to death. "Where are we going?"

As it turned out, Ino had planned out almost every detail of the evening, right down to the seating arrangements. Sakura was already feeling ridiculously underdressed at the more high-end restaurant they'd been dragged to, and having to practically perch on Shikamaru's lap wasn't helping. Sure, Ino looked happy about the inevitable results of procuring the tiniest booth in the place, but her human seat, while not looking particularly comfortable, wasn't making every attempt to wiggle away from her.

"Will you stop squirming," Sakura snapped quietly as she nearly toppled onto the floor.

"I'm not trying to."

"Then don't do it!"

"Ugh," Shikamaru sighed. "You're such a girl."

"And you're knees are knobby and uncomfortable, but do you see me complaining?"

"Yes."

"…I hate Ino-pig."

"Hm?" The blonde in question seemed eerily attuned to the sound of her own name, as she'd completely ignored their hushed argument before she'd been mentioned. "Have you guys made up your mind about food yet?"

"Do they serve anko dumplings?" Sakura asked, having been too distracted to even glance at her menu.

"Probably. But I was thinking – this place isn't cheap, so why don't we split two meals between the four of us?"

The more she considered it, the more sense Ino and Chōji seemed to make as a couple. Of course, their dynamic was a little strange, but Ino would never stray from her ubiquitous diets with Chōji around to eat all the foods she deemed too fattening. Maybe, eventually, he could even convince her to give up on dieting altogether.

"Sounds good," Sakura agreed, after a firm kick to her shin courtesy of Ino's high heel indicated her concurrence was mandatory. "What do you want, Shikamaru?"

"To be at home sleeping. But food-wise? I don't care; order whatever you want."

Sakura rolled her eyes. Typical. How had Ino even convinced him to act as a (not particularly successful) accomplice in her ploy?

"You're a sucky date, you know that," she informed Shikamaru just a bit sullenly.

"How do you figure?" he said without sounding particularly insulted. "I held the door open for you, didn't complain when you sat on me, which, admittedly, wasn't your choice, and I'm going to pay for the meal."

"You are?"

Shikamaru rubbed the back of his neck as if this exchange was taxing his conversational skills. "Yeah."

"Oh. Okay then." Somewhat placated, Sakura asked, "What do you want to drink?"

"Not necessary," Ino interjected smoothly. "Drinks are taken care of."

"Really." Sakura quirked an eyebrow at Ino's devilish grin.

"Yup." With a flirtatious lowering of her eyelashes in Chōji's direction, the blonde produced a highly suspicious-looking flask from some unknown crevice in her skin-tight dress.

You've got be kidding me. "You brought alcohol?"

"Yup. And lucky for you, I'm willing to share," Ino said, before swallowing a generous amount of whatever illegal beverage was in that so-subtle flask. She offered it to Sakura next, whose attempts to fend off her friend's outstretched arm were about as discreet as the silver container from which she was attempting to avert her eyes.

"Quit it, Ino," she hissed, glancing around to see if they'd been noticed. They hadn't. "You know we're underage, and more importantly, I have a med test tomorrow. Tsunade-shishou would kill me!"

"Bo-ring." Ino's gaze was sharp even as she rolled her eyes. "So we're allowed to risk our lives on missions, but we can't get drunk? That's ridiculous! Chōji, Shikamaru, how 'bout you guys?"

Chōji accepted Ino's offering without much need for persuasion; honestly, he seemed a bit overwhelmed by the whole date situation, but still…wasn't it dangerous to guzzle that fast? As a medic, Sakura had to conclude that it certainly couldn't be healthy. Then again, the pace with which he'd been inhaling the chips he had insisted on bringing had increased in tandem with Ino's flirtation, so maybe a calming drink was exactly what he needed. Anyway. Shikamaru, who Sakura fully expected to decline with his usual slouching disinterest, accepted his turn casually.

"I didn't figure you were much of a drinker," she said, curious more than anything else. Shikamaru could be annoying, but in the past his intelligence had – when he bothered to participate – made for interesting conversation, and, as far as she was aware, he'd never been unable to justify his actions.

"I'm not. But Ino has a point." Shikamaru shrugged, punctuating his comment with a swig from the proffered flask. "Maturity, regardless of age, is a matter of survival for shinobi, and they experience things that normal civilians can't imagine or relate to; it makes no sense to apply the same age restrictions to both."

"So by drinking you're sort of protesting an unreasonable policy?"

"Ugh, forehead." Ino's head fell back on Chōji's shoulder with a light thwap, whose round cheeks coloured in a way that was almost…cute. "Only you could turn the consumption of perfectly unauthorized sake into something nerdy."

Shikamaru smirked, ignoring his teammate's eloquent input on the matter. "Protesting? Sure. But mostly I'm just trying to drown out Ino's chatter."

Sakura giggled despite herself, and, perhaps against her better judgement, snatched the seemingly bottomless flask from the dark-haired slacker. "What?" she demanded, blushing when Shikamaru eyed her warily. "I'm protesting the unfair prohibition of certain mind-altering substances."

"Nerdy," Ino chimed in.

Sakura couldn't really disagree, so she settled for another sip of sake. Although Tsunade-shishou swore by the stuff, Sakura had never seen the allure. The taste was sharp and choke-inducing at first, but the more Sakura imbibed, the more palatable it became. It wasn't long before the night drifted beyond her control, hazy and laughter-filled.

They were stumbling home when it happened. Sakura couldn't have said who instigated it. One moment they were upright and half-leaning on each other, and the next they just sort of fell together, their lips meeting as if by mutual accord.

There was no moment of uncertainty or we-shouldn't-be-doing-this unease. The clarity of sobriety was a distant memory. A bit dizzy, Sakura peeked her eyes open. All she could see were dark, shadowed eyelids, the curving bridge of someone's nose, and a glint of steel out of the corner of her hazy vision: a silver stud earring. Warm breath tickled her tongue and she inhaled the feeling of wind-roughened lips moving almost carelessly over hers. In a very offhand way, she became aware of a calloused hand at her waist, just under the hem of her pyjama shirt. Another twined in her hair.

Her body tingled with unfamiliar sensitivity as the hand caressing her stomach drifted upwards, barely ghosting over her ribcage before trailing around to her back. Hard stone dug into her shoulders, supporting her when she might have fallen. A low, muffled word was swallowed by her mouth, followed shortly thereafter by a rush of cold air, and a gasp, her gasp this time, as something tickled her neck. Lips, hot breath, a hint of teeth. She giggled at the sensation on her flushed skin, fingers curling around biceps that tightened under the light pressure. Then…

"…Sasuke." There was that word again, audible now that it was being murmured against her collarbone.

"Wrong name," Sakura huffed, leaning her head back in a futile attempt to equate physical distance with emotional detachment. What was she doing?

Shikamaru's lips stilled as he drooped so that his forehead was resting in the crook of her neck. His breath, slightly irregular, hit her like kunai just above the edge of her shirt.

"Sakura –"

"That's the one," Sakura interjected.

"You love Sasuke, right?" His voice was quiet, but the words themselves more than made up for what they lacked in volume.

"Of course." The response was oddly automatic.

Sakura couldn't read the expression on Shikamaru's face as he said, "I don't love you."

"Okaaay. Um. I don't love you either?" Where was he going with this?

"We're both…not really thinking straight." That was putting it mildly.

"Thanks to Ino." And her magically limitless supply of super-sake. And the fact that Sakura refused to be beaten by her sometimes rival, regardless of the competition.

"Thanks to Ino," Shikamaru agreed. "So do you honestly think…that…was a good idea?"

It had felt like a good idea, at least at the not-so-long-ago time. Thinking only of hiding her expression, Sakura buried her head in the shoulder of Shikamaru's chūnin vest.

"No wonder you're a virgin," she mumbled, not altogether happily, into the hollow of his neck. It was something she never would have considered saying had she been in her right mind, but now it just sort of rolled off her tongue. There was also a distinct possibility that her words were slurred nearly beyond comprehensibility, but she couldn't seem to find the energy to care. "Do you have to analyze everything?" Isn't that my job, anyway?

"Who said I was a virgin?"

Even with her mind buzzing like a hive full of pissed-off bees, that got Sakura's attention. "You're not?"

Now that she was actually looking, Shikamaru wasn't really unattractive. The thought of a girl liking him romantically was weird, but not unimaginable. He was no Sasuke-kun, of course, but there was an odd sort of appeal to the casual droop of his eyes, a contemplative quality to his frown that could be endearing…

Shikamaru shrugged, an awkward motion with her leaning on his upper body. "Girls are troublesome."

Okay. Certain aspects of his vocabulary could use broadening. "That's not an answer."

If she strained, Sakura could just make out the hint of a smirk on his night-darkened features. That was all the answer she got.

Of course, he might simply have been gearing up for some significant, slightly alcohol-induced secret-confessing. Sakura would never know, considering her stomach chose that moment to jump into her throat, doubling her over in a sickening prelude to vomiting.

He should have dodged; he could have, she was sure. Then again, it was entirely possible that alcohol-consumption had addled his shinobi reflexes as much as it appeared to have affected hers.

Whatever.

It wasn't her shirt covered in unmentionable goo.

Next thing she knew, her body was airborne and moving, a not altogether comfortable sensation that evoked the unappealing prospect of a repeat performance, throw-up-wise.

"Shikamaru," she said, almost whining. "Put me down."

"I'd love to."

Sakura waited to be dropped unceremoniously on the pavement, relaxing only when Shikamaru tightened his hold on the back of her knees and started walking. Being slung over Shikamaru's shoulder might not have been an improvement on perching on his lap, she found, but it did offer a lovely view of the alley by her house.

That's right – her house. The details were a bit fuzzy, but Sakura distinctly remembered Ino making up some bogus excuse about her and Chōji needing to pick something up at the training grounds after they'd left the restaurant. It would have been hard to forget the blonde's smirk as she'd said, in a guileless tone that belied both her intentions and her state of inebriation, "Have fun, kids."

Which had left the other half of their 'spontaneous' double-date to stumble home in each other's company. And then…well…

With a disconnected sense of honesty, Sakura wished Shikamaru hadn't brought up Sasuke-kun. Then again, it was probably a good thing he had. But on the other hand…

"Shikamaru," she began, nervous hands toying with the zipper on his vest. "Do you want to come in?"

A/N: Oh, Shikamaru, such a tease...