A/N: Before anyone tries to kill me, let me say something in my defense.

First of all, HAPPY NEW YEAR! I do hope everybody had a wonderful time during the Holidays. Where I live, they're not over until like mid February or something, but yeah...

I have a perfectly good excuse for going missing these past few weeks. Not to sound like Kakashi, but my boyfriend's puppy went missing the week before Christmas. Needless to say, I didn't even touch the laptop during that time. I spent the whole week hiking the wilderness, trespassing private property, handing flyers, managing the social media, and even guarding a perimeter (and getting catcalled more than once while at it, thank you very much). We finally found the puppy a week later, pretty far from where he got lost, slimmer and scared, but in one piece.

The next week I spent doing chores and didn't really have time to write. Finally, some days ago, I decided to get back on track, which was kinda hard. I actually was going to publish a Christmas SasuSaku one-shot that's now half-way done becase of the puppy, but couldn't seem to get back at it the way I wanted to. So, I decided to write something else to get the blood flowing.

I came up with a one-shot that had way too many details in it, and so, I decided that it would look better as a multi-chapter. I mapped everything out, literally. I have a document with all the chapter names and descriptions already.

For the sake of this, I'm going to delete another story I have here, since it kinda fused with this one, and I think it works better this way. The premise is very similar, though.

After writing Captain Hatake's Training Seal, I wanted to do another KakaSaku, because I love that pairing almost as much as I love SasuSaku. Also, I'm over confident and think my OCs are awesome, so I wanted to bring two of the ones I used there back and delve deeper into their stories.

I'm going to shut up now.

Here ya'll go! Hope you enjoy this new story!

Disclaimer: I do not own the Naruto characters. All the OCs are mine.

*Do I really have to keep writing the mature content warning? Haha!

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Risky Endeavors

Prologue: Broken Compass

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The pit pat sound of the rain drops hitting the glass window filled the room and echoed softly off the walls. The harmonious sound shouldn't have been enough to even stir anyone from sleep, but it woke her up. The pair of emerald green orbs opened groggily, only to close again a second later when the sunlight of early morning filtering through the drapes blinded her vision. They were slow to adjust to the clarity, slower than usual, and this quickly dissipated the remnants of sleep from the kunoichi. Her body sprung to a sitting position on the soft mattress, eyes widening as they took in her surroundings. The action was regretted instantly, as the full force of the headache slammed into her and her vision blurred. A slight panic settled in the pit of her stomach as her mind became painfully aware of other things: the slickness of her skin due to a dried sheen of sweat all over her body, how sensitized her breasts felt when the covers had slid off her due to her lack of clothing, the slight throb between her legs.

Her breath quickened instantly as she understood her situation. This can't be. Fear seemed to paralyze her limbs as her eyes darted around, and she felt her stomach drop. Recognition came easily. She'd been here before, although, never this early in the morning, and certainly not naked. If the young woman had had any doubts, the orange book sitting innocently atop the desk in front of the bed was more than enough evidence. It almost physically hurt her to turn her head to the other side of the bed, and she couldn't stop the sob that slipped past her lips.

There he was, sleeping soundly beside her, the covers up to his waist. Her eyes roved the planes of his back, as he was laying on his stomach, lingering on every old scar decorating his flesh. Up they went, to the unruly mop of silver tresses gently splayed on the pillow, and lastly, to his face. His uncovered face, she noted. The girl took him in: his straight nose, high cheekbones, strong and defined jaw, plump lips, and a small beauty mark just under the left side of his mouth.

Morbid fascination almost made her laugh at the irony of it all. Of course, he wouldn't have his mask on after what most likely had transpired on these sheets the night before. The thought made her heart clench, and the desire to cry became almost unbearable, but she held on to the last scrap of her sanity. Reverting to her twelve-year-old crybaby self would do nothing to better her predicament; if anything, it would just worsen it. Taking deep breaths to calm herself, she raked her mind to remember something, anything, that explained how she had ended here, but it wouldn't cooperate.

The only thing she remembered lucidly was the smell of cigarettes and liquor.

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"Earth to Sakura!"

At the mention of her name, the pink-haired medic snapped her head back in her friends' direction. The blush decorating her cheeks due to the sake she had been drinking increased exponentially at the realization that she had been caught dozing off. She heard Ten Ten snicker and saw Hinata cover her mouth to hide her smile. Ino sat right across from her on the table, her blue eyes glinting mischievously as she looked at her best friend.

"I'm glad you're back with us." she mocked, and took a sip from her glass.

Sakura would've rolled her eyes, but only managed a yawn. "Oh, come on, cut me some slack. I had a ten-hour surgery today." she mumbled while propping her elbow on the table and resting her cheek on her open palm. "I'm tired."

Indeed, she was. There was nothing Sakura Haruno wanted more at the moment than to return to her house and hide under the covers for eight hours straight, maybe more. Of course, seeing as most of the teams dispatched on missions were due to return this week, she doubted she'd ever get that far. Work had been all-consuming this month, the reason why she had accepted to go out with the girls tonight, exhaustion and all. She needed the rest, but she also needed the distraction.

'Because today is also the day he…'

Ten Ten's words broke through Sakura's myriad of thoughts. "Hot stud alert!"

The three remaining females turned their heads in the direction Ten Ten was pointing to, or rather, to whom she was pointing to. The group of jonin at the bar consisted of about six people, but Sakura easily made out who her brunette friend was referring to. He was younger than the rest of the men, if only by a couple of years. Dark, almost shoulder-length locks were slicked back on his head, leaving his handsome face exposed for all to see. Currently, he was chatting animatedly with Genma Shiranui, the latter sporting a smirk on his face while the ever-present senbon on his lips moved languidly up and down. Sensing eyes on them, Genma glanced over to their table, the girls quickly averting their gazes elsewhere. Sakura could've sworn she heard him chuckle.

"I swear, it should be illegal to look that good." Ino murmured, her eyes flicking to the bar again.

Outwardly, Sakura snorted. Inwardly, she couldn't agree more with Ino's observation. The name of the guy was Kotaro Furushima, an ANBU Black Ops member and the newest drool-inducing anatomical masterpiece of the Hidden Leaf Village's male population. Sakura had met him a few months back, when she had been assigned to treat his squad after a mission. Only herself and a handful of medics were deemed trustworthy enough to heal ANBU members, taking into consideration the delicacy of keeping their identities a secret. Even though his injuries had been grave, Kotaro had breezed through her healing with an unwavering sense of humor and more than a few dashing smiles, which had kept her good mood up throughout the entire process. He was a charming guy and a very capable shinobi. Mostly, he was kept away from the village on lengthy missions, but lately they had been seeing more and more of him, a fact more than welcomed by the other females of the Rookie Nine and Team Gai, Ino and Ten Ten specifically.

"You're drooling, Ino." Sakura teased from behind her lifted glass.

Ino was quick to react. "I am not!" Sakura didn't miss how she brought her thumb up to the side of her lips and brushed the skin delicately. The pink-haired kunoichi snickered.

"Regardless, Ino's right." Ten Ten added. "Just look at him. A man who carries himself with such confidence definitely exceeds in the bedroom."

The brunette's words made Hinata blush from her place beside Ino, the blonde taking notice of this.

"I think someone just admitted that to be true."

The Hyuuga's eyes widened as she regarded her friend. "Ino!"

"Tell us." Ten Ten started as she leaned over the table to shorten the distance to the dark-haired kunoichi. "Is it good?"

Apparently, the liquor was starting to take effect, and Sakura didn't particularly like the direction their conversation had stirred to, and it had nothing to do with the fact that Ino and Ten Ten seemed intent on scrutinizing Hinata's intimate life. It reminded her of him…

'If only…'

"You guys…" Hinata began, obviously embarrassed to be thrusted under the spotlight.

"Can we change the subject?" Sakura interjected. At the confused look Ino threw her way, she quickly added. "I'm not drunk enough to hear the words 'Naruto' and 'sex' in the same sentence. No offense, Hinata."

The Byakugan user gave her a soft smile, not in the least bothered. Ten Ten shrugged and took another swing of her beer, he eyes glancing over to the bar once again. However, Ino's gaze didn't leave the fellow medic. As Sakura looked at her, a silent understanding passed between them.

'If only… he'd stayed.'

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No matter how hard she tried, she couldn't remember how much she'd drank the night before. Glass after glass had come and gone, and her alcohol-laden brain had successfully lost count after the fifth. It had seemed like the most plausible idea yesterday: to drink her problems away. There had been an underlying reason as to why she'd accepted her friends' offer to go out for a drink, and it had nothing to do with the general stress her work in the hospital produced. She hadn't voice it, but they knew. Ino absolutely did.

The man beside her stirred and Sakura almost jumped out of her skin. He turned to lay on his back and threw a muscular arm over his eyes, but didn't wake up. Adrenaline coursed through her veins at rapid speed, the effects of the hangover heightening as she started devising a plan to escape. If she stayed a minute longer, the tears would start falling and she'd surely break down.

As she attempted to move her legs to swing them off the bed, the throb in her womanhood increased and she had to bite her lip to keep from making any sound. Hesitantly, Sakura grabbed the edge of the covers with a trembling hand and lifted it slowly to get a glimpse of what lay underneath.

Blood.

Dried blood.

It stained the inside of her thighs and the rumpled sheets, and she dimly noted it was mixed with a white substance on the apex of her thighs. Her hand darted to her mouth in an attempt to muffle the loud sob as her eyes brimmed with tears.

'No.'

"Sakura?"

The kunoichi had half the mind to cover her nude breasts with her arms before her face turned to regard the man.

'Why?'

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The bass of the music echoed off the walls, successfully drowning the conversations around them. At a quarter past midnight, the pub was filled to the brim with people smoking, drinking, and dancing. The mixture of the distinctive smells filled her nostrils and seemed to elevate her even more as she swung her hips from side to side somewhere within the throng of sweaty bodies. She'd lost count of the glasses, and the one on her hand was dangling dangerously, spilling a bit whenever she twirled, although she didn't seem to mind. The faces around her were a blur, and what kept her grounded was Ino's hand grasping her own as they danced.

Sakura felt it all slip away: her concerns, her fears, the frustration eating away at her. What was left was a lightness in her brain and her limbs, and a smile on her lips as she lost herself to the hymn of the night. She had tied half of her shoulder-length hair up in a messy top knot, some loose strands sticking to her sweaty forehead and the back of her neck. Tonight, she had discarded her usual clothing, opting instead for tight fitting jeans and a strappy shirt that reached just over her belly button. She felt the fabric sticking to her slick back as she ground her hips. It felt wonderful to be like this, free, unsuspecting of everything for once. With every new beat of the music, the dark memories plaguing her dissipated.

'He's not here.'

Twirl.

'He's not interested.'

Grind.

'He'd rather stay away.'

Twist.

'He'll never truly be back.'

The pink-haired kunoichi noticed Ino looking at someone behind her, her blue eyes glinting with mischievousness, albeit looking as dazed as hers surely were. The next thing she knew, her blonde friend took the glass from her hands and slipped away through the crowd. Sakura barely had time to register what had happened when a pair of strong arms wrapped around her and locked just under her breasts.

The influence of the liquor in her body rendered her docile. For some unknown reason, turning around and slapping the living daylights of the man who dared approach her in such a way was the farthest thing from her mind. Sighing in contempt, Sakura leaned back against the stranger, her hips rocking onto his slowly as she relished on the contact. It thrilled her, aroused her to be like this with someone. Usually, she was too uptight to be in this position with anyone, but tonight was different. Tonight, she didn't mind.

'He's not here.'

The mysterious man suddenly pulled her body flush against his, and Sakura felt a shiver run down her spine. He was taller than her, the muscles she felt underneath his clothing hard and strong, although they didn't feel bulky. She reached behind her to tangle one of her hands on his hair, and she was amused at how soft they felt between her fingers. His face lowered to her neck, his lips a breath away from her skin, but never touching it. In his breath she quickly recognized the scent of a strong alcoholic beverage.

'He's as drunk as I am.'

That was the last thought crossing her mind before she lost herself to the music in the stranger's arms.

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All the humiliating moments in the past weren't enough dim the feeling that settled in the pit of her stomach as her jade eyes locked with mismatched onyx and crimson. He was still groggy from sleep, and a possible hangover as strong as hers, but recognition easily dawned on him. Sakura watched the shinobi's eyes widen in disbelief as he looked at her. Sitting upright slowly, he rubbed his eyes with his thumb and index finger and pinched the bridge of his nose. Even in her current predicament, it was somewhat mesmerizing to watch him do this with an uncovered face.

"Sakura, what…?"

He didn't finish the question. His nose scrunched up and his head snapped in the direction of the sheets pooled at her lap. She'd known him for years. Seeing as his ninken were dogs with a very precise sense of smell, Sakura was positive his had developed beyond a normal man's, albeit not as strong as an Inuzuka's.

A shadow washed over his features and his jaw tightened; so did his fists, enough to almost tear the covers apart. Sakura hung her head, unable now to meet his eye.

"Fuck." she heard him curse under his breath.

It was all she needed to start crying.

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Her back hit the wall of the room hard, bruising almost, but the only thing she was focused on at the moment was the pair of soft lips slanting roughly over hers. They were as insistent as the hand currently grabbing a fistful of her pink tresses, while the other one slipped under her shirt to cup at her breast over the lacy material of her brassiere. Her hands were also busy, one fisting the hairs of his nape while the other still held the fabric of the mask she'd slid down his face. In a bold move, his hands reached behind her and squeezed her ass, signaling her he needed more contact with her body. Complying, Sakura held onto his shoulders and pushed herself up, her strong thighs wrapping around his narrow hips while he pressed his body to hers, holding her in place against the wall. A lustful moan slipped past her lips as she felt him grind his clothed erection to her core over and over again.

"Ahh! God, yes…" she breathed out as his hand slipped inside her shirt again, this time reaching under the undergarment and pinching her nipple softly. His mouth attacked her collarbone now, licking, and kissing, and nipping at the sensitized skin until her pelvis started grinding back, trying to find some release from the pent-up arousal she'd been nursing since the moment they entered his apartment.

"Lift your arms." he ordered, and she felt her insides clench at the husky tone of his voice. She did as she was told, and soon enough her torso was bare for his eyes to see. Sakura bit her lip as she watched his mismatched orbs roving over her supple skin, lingering on her hardened nipples before he reached down to kiss her senseless again. He was such a good kisser.

"Mmhp! Please, I need you… Ah! Please!" she murmured against his lips in between lip locks, and felt him smirk against her mouth before biting down on her lower lip and giving it a playful tug.

"We have all night for that." he said.

The kunoichi was having none of that, however. Mustering some of her strength, she pushed him off her. The silver-haired man stumbled a few steps back until he was met with the back of his couch. Before he could protest, she was kneeling before him, her hands working the zipper of his pants. A loud grunt was heard as he threw his head back when her mouth engulfed the tip of his member. One hand propped on the couch to keep his balance, the other one tangling on the back of her head and urging the woman to take him in deeper.

It was a blissful experience to have a man bent to her will. She wasn't even ashamed of doing this, and the fact that she'd never done this before was instantly forgotten as she heard the sounds he made. Her body was running of pure primal instinct and alcohol at this point.

"Fuck… Ahh… Can you take more of it?" he asked looking down at her, suppressing the urge to thrust his hips into her mouth at the look she gave him. She tried, but the moment his hard flesh hit the back of her throat she gaged and had to pull back. Coughing a few times, she leaned back on her bent knees, spit drizzling down the corners of her mouth.

"Sorry." Sakura murmured and gave him a sheepish grin.

He chuckled and outstretched a hand to help her up. Once she was upright, he switched their positions, her back now leaning against the couch.

"My turn." said the man as he kneeled before her and unbuttoned her jeans, pulling them down along with her underwear in one swift movement.

Now it was her turn to throw her head back as his devious tongue lashed out between her legs. It was pure bliss, indeed. Why had she denied herself such a wonderful experience before? Oh, of course.

'This isn't him.'

Another lick.

'This isn't Sasuke.'

Another suck.

'Who fucking cares anymore?'

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It took several minutes for her tears to stop, even as her chest kept heaving. He kept silent all the while, giving her the time she needed. She figured he must've been as confused as herself about what was going on, even when his reaction was different from hers. She felt embarrassed. He just seemed… angry.

"I'll get you some clothes." he said, his eyes never meeting hers, as he stood up from the bed. Sakura quickly noticed he was naked as well, and averted her eyes. No need for more cruel reality checks.

A change of clothes, consisting of a long-sleeved shirt and a pair of loose fitting shorts, was placed beside her on the bed. She kept her head low as she heard him walk across the room and close the door a little too roughly.

Holding back the tears, Sakura stood up from the bed, her eyes lingering for a second on the bloody mess in the sheets. Grasping the clothes, she headed for the small bathroom, stepping on the clothes she had worn the night before that lay scattered across the floor in the process. She'd have to pick them up eventually, but they had a foul smell to them, and she had no intention of walking out of here with such an obvious evidence clinging to her body. Although, weren't his clothes enough evidence already?

Closing the door behind her, Sakura turned to look at herself in the mirror. The make up from the night before was smeared, especially around her eyes due to the recent tears, and her lipstick was nonexistent. She barely recognized herself, and the urge to cry made itself known again. Walking over to the shower, she turned the temperature to the hottest, almost as if she wanted it to wash away her sins, her skin, everything she had done, away.

Goosebumps crawled up her naked flesh as she sat down on the cold tiles and settled for watching the water fall. Her eyes followed the small current, which quickly turned a rosy color as the blood between her legs was washed away. Sakura brought her knees to her chest and wrapped her hands around them, her head hiding between them.

'Why?'

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He kissed her again to muffle the scream when he entered her, Sakura's fingernails raking painful trails down his back to try and ease the pain.

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'It shouldn't have been you.'

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Glancing down between them, a concerned look washed over his face when he noticed the blood coating his member as he pulled out. His eyes searched hers, a little unfocused by the copious amounts of alcohol he had consumed.

"Sakura, you're…"

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'It was supposed to be Sasuke.'

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Her hands tangled on his silver locks and pulled him down for a rough kiss, her tongue delving inside his mouth hotly despite the pain.

'Don't stop now… please…" she whispered against his mouth, her eyes opening to meet his with an intensity she'd never directed towards this man before. 'Please.'

Tentatively, he drew back and thrusted forward again, making her clench her teeth. Still no good, still too much pain.

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'Never you.'

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The intense pain turned into a slight throb mixed with the most intense pleasure Sakura had ever felt. Her whimpers turned to moans, and soon enough he was pounding into her with abandon.

"Sakura." he whispered against her skin.

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'It was never supposed to be you…'

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She came screaming his name.

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'… Kakashi…'

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A/N: I've come to peace with myself about the fact that I will never be able to write something short. Haha! I hope the back and forth wasn't too confusing, I wanted to try that out. Soooo, let me know what you guys think! This prologue is like a back story to their dynamic in the story, so do expect things to start slower in the first chapter, which I hope to have finished soon.

Reviews and Favorites and Follows and PMs are always more than welcomed, so is constructive criticism. Thank you for always being so supportive of my writing, it means the world to me, guys! See ya on the next chapter! :)