Sakura rationalizes this as well, and lets him keep going

Original Chapter by AkaB

Shikamaru stared at the little starfish-like entrance to Sakura's ass. He'd never seen a girl's anus before – hell, he'd never even thought about a girl's rectum before today. But there was something about it that captivated his attention. Maybe it was because that even when a girl was naked with her slit in view, her anus was still generally hidden away in the shadows of her buttocks cleft, making it truly the most secret of places?

...And he couldn't deny that the Nara clan did have a natural predilection for places with plenty of shadow, too.

Sakura certainly agreed that it was a place that wasn't meant to be stared at, so it was unfortunate that she'd convinced herself that she couldn't say that. Even though she couldn't turn her head very far, thanks to Naruto's stiff cock in her mouth, she could still almost physically feel Shikamaru's burning stare between her spread ass cheeks.

Without being able to really see what he was doing back there, and not knowing what he found so fascinating about her asshole made her feel vulnerably exposed. Somehow, this felt even more humiliating then when she'd been spreading her labia for everyone to see her most precious place. At least with her pussy, she expected boys to be curious about her putting her pink slit on display. But even in her most fevered, hormone-driven fantasies about Sasuke, she'd never dreamed of the Uchiha showing an interest in the particular hole that Shikamaru seemed to be so absorbed about.

'Why is he staring at that!? My bodily waste comes out of there!' Inner shrieked. 'We have to make him stop!'

Sakura considered it for a moment, before giving a resigned mental sigh. 'He thinks we already gave him permission. If we withdraw that, he'll try to figure out why we backed out. And we both know from all of those idle comments he's made during class over the years that he's a lot smarter than his grades made him look. He'd figure us out for sure.'

'But... but... he'll do butt stuff!' Inner argued.

Sakura put some attention into rolling her tongue around Naruto's cock, reapplying her efforts to getting him out of her mouth as quickly as possible by getting him off, as she tried to distract herself from the thought of having a boy's thing in her ass._ 'That's... that's ridiculous. Nobody wants to stick anything in there. It's dirty!' _she weakly responded in her mind. 'Besides, Shikamaru's way too lazy to actually do anything. He'll get bored of this and go off to look at clouds in a minute.'

Unfortunately, while Sakura knew of Shikamaru and the Nara clan well enough to know of their legendary laziness, she hadn't yet realized that much of the clan's laziness stemmed from being so intelligent that most common or mundane things bored them. If there was something sufficiently interesting around to grab their attention, a Nara could be just as motivated as the next person, even if they still put up an act to pretend that they didn't care.

For Shikamaru, his interest was currently piqued by two questions. Firstly, would Sakura truly allow them to do anything to her body in the name of skinship? So far, the answer certainly seemed to be 'yes'. If he'd placed a bet before this day had started on how something like this would go, he would have laid money down that she would have punched him long before she'd allowed him to spread her ass like this.

It was unexpected and against his previous impressions of the girl, of course, but not completely earth-shattering to his view. After all, as far as he was concerned, all women were crazy and illogical. It wouldn't be the first time he'd seen them label something one way while he labeled it something almost the opposite – like them labeling Sasuke's abrasive monosyllabic standoffishness as a brooding cry-out for a girl's love. While he may be extremely intelligent, between his own domineering, nagging mother and the loud obnoxious fan girls of Sasuke in his class, he'd never really had a desire to figure out anything more than the advice his father had given him of 'woman are contrary, just accept it' about the minds of the opposite gender.

The second question that was slowly firing him up now that he'd gotten this far, though, was what would anal sex actually feel like? How would it feel to slowly sink his cock into Sakura's admittedly fine-looking ass? Because he might be lazy and think women were crazy, but he still had hormones and he wasn't blind to the girl's nicely shaped posterior. For once, thoughts of staring at the clouds were sent to the back of his mind as he took one of his hands away from the girl's ass, while using the splayed fingers of his remaining hand to awkwardly keep her cheeks spread.

With a focused resolve that many would find uncharacteristic of his clan, he carefully spat on his index finger to give it a bit of lubrication, before he unhesitantly slid his saliva coated finger into her tight puckered hole.

'Holy shit! Holy shit!' Inner screamed as Sakura's eyes widened into saucers. She's never had anything inserted into her ass before, not even during the most invasive of the mandatory pre-graduation medical tests. It felt weird and wrong and she had to stamp down on her Inner's extremely strong desire to try and force it out.

_ 'Don't clench down!' she warned her Inner, as Shikamaru slowly plunged down to his second knuckle. 'If we do, he'll know that somethings up! We're supposed to be okay with this, remember?'_

_ 'But it's in our bu-huh-hutt!' _Inner whined as Sakura's dual personalities shared the discomfort of having someone invade their ass for the first time. She'd never been on a date, never been kissed, never even held hands with a boy that she liked, and here she was with someone else's finger sinking into her rectum. And it was happening outdoors in the public baths, where anyone could walk by and see it going on! The Hokage himself had already stumbled across them, so how long did she have before more people came and saw her like this: on her knees and elbows, naked, sucking one boy's cock with another one fingering her ass, all while more boys (and a girl) watched her debase herself?

Despite the obvious social ruin that she would go through if anyone who knew her stumbled across her, she didn't make any move to leave. Sakura was an extremely intelligent girl, even if she did let her more passionate emotional side make too many of her life decisions. As smart as she was, she should have cut her losses long before she found herself in this position, the situation somehow having spiraled down into her taking in the boys' fingers and cocks in order to save face. But Sakura was too early in her ninja career to have enough experience to know when to disengage from a bad plan and accept her losses, falling into a sunk cost trap of her own making.

So, like the ninja in the stories she had been raised on, who stoically completed their missions no matter how many stab wounds they had (usually so that they could get back home to the kunoichi they secretly loved so that they could confess their undying devotion), she endured. She endured the humiliation and weird sensation of having Shikamaru's finger wiggling around in her ass, mentally keeping herself from clenching so that he had an easier time of it as she gamely continued to suck the cock of the second biggest loudmouth she knew (second after Ino), all while hoping that going along with all of this and pretending that it was normal would mean that everyone here wouldn't think it unusual enough to tell other people about it.

The onlooking boys stared in rapt fascination at the sight of the normally prim and proper kunoichi taking a finger up the ass without a single complaint. Several of them twitched their fingers, longing to wrap their hands around their cocks and masturbate to the sight, but the presence of the other girl among them stopped them. None of them wanted to break whatever spell that Sakura was under, and having Hinata faint might just do that.

As for Hinata herself...