A/N: Good grief. I apologize for the typos on the previous chapter, I also apologize in advance for the typos that follow.

Also, I'm not sure I want to invest too much in the plot. hmm. Lemme know.

XXX

She was supposed to be studying, damn it!

Sakura picked up her phone for the tenth time that morning. She'd had little to no sleep at all, having the silver haired man invading her thoughts just as soon as her head hit the pillow. The previous evening's events replayed in her mind's eye on repeat, the memories still fresh.

She considered his offer, mulling over the possibilities what exactly it could be. An assistant position.

Assistant position to what?

It sounded entirely innocent, but Kakashi had made it clear that innocence was definitely not the correct term to associate the word 'assistant' with. But for the life of her, Sakura couldn't figure out what the hell he meant.

Was he a business man, in need of an assistant to corner in dark broom closets without the added strings attached whenever he felt like it? No, Sakura thought, that couldn't be it. There was an offered payment at the end of whatever it was that he expected of her, which means it could very well be a job position. But he had made it clear that it definitely was not a date turned interview.

Sakura groaned, annoyance starting to creep at the edges of her tired mind. She opted to take a nice, long shower instead of trying to break her mind over what exactly it was that Naruto had dragged her into.

She knew little to nothing about Kakashi, other than her read porn, participated in orgies for research purposes and was a whopping 37 years old. She'd asked about the mask, but he managed to divert her attention to something else instead. Maybe he really had a birth defect that would otherwise put potential lovers off if they saw it before getting to know him.

Naruto had mentioned that he was the type of guy she would normally seek out if she felt a certain itch become too much to tolerate, but other than the fact that he was willing to have sex without getting too much feelings involved, she hadn't been any wiser today than she was the previous day why Naruto mentioned he knew a guy she would most definitely be interested in.

She'd told Naruto to inform Kakashi that she was fine with just getting drunk, not expecting a fluffy date setting. Perhaps the silver man took her words too literally, seeing as he simply just slipped a piece of paper to her with his number scribbled on with instructions to contact him the following day to find out what exactly it was he offered her with the promise that it included sex.

She had honestly hoped that after the teasing and kissing he would at least invite her over to his place, or suggest they go the hers.

Sakura sighed heavily once again as she finished with her shower. The hot spray of water helped with giving her a little more energy for the day, but did nothing for her thoughts on the matter at hand.

The pinkette narrowed her eyes on her cellphone. Making up her mind, she quickly scrolled trough her contacts searching for the silver haired man's name. Before she could hesitate, she dialed the number.

It only rang for a handful of seconds before Sakura heard a greeting from a deep voice on the other end of the line, "Er, Hi. Am I speaking to Kakashi?"

There was a pause, then; "Ah, Sakura. I almost thought that I might have scared you off with my age."

He was waiting for her call?

Of course he was, no one would just give out their number to a potential lover and then assume they'd never call. Unless the other party had made it obvious that they held no interests whatsoever.

Sakura could hear the smirk in his voice, a small tilt forming on her lips in response.

"I was tempted to make a beeline for the hills, jiji, but you've certainly convinced me to reconsider with the promise of finding out whether or not the rumors about older men are true."

Kakashi chuckled lightly at her jab, "I'd hate to be the one to make you wait in anticipation. If you're still willing to hear me out on my offer, I'll text you an address where we could meet up?"

Sakura lightly pulled at her lower lip with her teeth as she listened to the low baritone of his voice, "You've certainly peaked my interest, Kakashi. Text me the address and a time. I've nothing planned for the day."

"Good, I'll get to it then."

The line went dead after that and Sakura felt like she could kick herself. She must have been really stressed out lately seeing as she fretted over practically nothing. All she had to do was call the man the first time she picked up her phone.

Satisfied with the outcome, Sakura quickly shuffled to her room to get dressed for the day. Making sure to put on her most flattering lace underwear. Her insides quivered with excitement as she heard her phone vibrate before her message tone sounded.

The address Kakashi provided was only a few blocks away from her apartment. He's asked that she'd arrive around 12h00. Glancing at the time on her cellphone, she was pleasantly surprised that she didn't have to wait eagerly for the time to pass by. If she started walking now, she would reach her destination with a few minutes to spare.

XXX

Sakura arrived at the location provided to her by Kakashi. Knocking on the wooden door, she waited silently for him. It didn't take long before he greeted her, welcoming her inside of his house.

She was surprised by his taste in decor. His furniture was deep, rich colors of chocolate brown and blue. Sakura felt properly out of place. It reminded her sharply of an extravagant lifestyle. Something she was not accustomed to.

Kakashi offered to make her something to drink and she kindly accepted a glass of water. Leading her into his living room, Sakura sat down on one of the deep blue sofas. It looked like it was newly purchased. A fluffy black carpet was rolled out in the middle of the arrangement, the couches forming a 'U', chocolate brown side tables on either side.

Sakura studied her new surroundings as Kakashi excused himself to get her a glass of water, returning in a few seconds, seating himself on the couch to her right.

Taking a few sips, Sakura patiently waited for the man to speak first.

As if reading her mind, Kakashi gave a silent once over before speaking, "I'm assuming you're very eager to hear what I have to say?"

Sakura nodded, "Why else would I be here?"

"Very well, I'll start with the basics."

Sakura scooted herself into a more comfortable position on the couch before turning her gaze fully on his form, waiting for him to continue.

"How familiar are you with sexual education?"

Sakura blinked at the man, "Very. I'm a medical student. It's kind of in the description to become familiar with all kinds of aspects concerning the human body."

Kakashi nodded. Taking a moment to consider his next choice of words.

"How comfortable are you in front of a camera?"

Hadn't he asked a similar, if not the same, question last night? Sakura felt compelled to give the same reply she did previously.

"Comfortable enough, I suppose."

"How comfortable are you in front of a camera naked?"

His question took a moment to register in her mind. Naked? As in, taking naked pictures? She had verbalized her confusion at his question.

"That too, yes. But more specifically, video taping."

Sakura paused. She couldn't say that she had ever done something like that before. A previous lover once mentioned taking a video of them having sex, but she had refused, not comfortable with the idea that some guy she hardly thought about twice would walk around with a sex tape involving her. Kakashi took her silence as an opportunity to explain his questions.

"To sum it up for you; I'm a sex educator. At first I taught classes consisting of couples, men wanting to learn how to properly pleasure a woman. I guess through word of mouth my classes became more popular. People around town would start calling me to make private visits for independent coaching. Pretty soon I was starting to receive calls from all around the state. It got me thinking, instead of making house calls, I might as well teach people wherever with online classes. At first it worked, but without being physically there to coach the couples to do what they had learned, it made explaining harder. I figured the best course of action would be to do some sex ed 101 demonstration classes."

Sakura blinked owlishly at the silver haired man. Clearing his throat, she could see his eyes crinkle in what she assumed would be a smile.

"That brings me to explain why I'm in need of an assistant of sorts. I couldn't possibly do live demonstrations with a doll. The effect would be lost. It would be better to demonstrate on a real woman; record her real time expressions and experiences of pleasure. Therefore the viewers would have a better understanding. It would also be easier for them to practice what they learned."

"You're asking me star in amateur porn?" Sakura deadpanned.

The laugh that escaped Kakashi throat both bewildered and amused Sakura.

"No, Sakura. Not porn. Sex education. Porn is nothing but lies."

Sakura snorted, "you sound sure of yourself."

Kakashi leaned forward in his seat, resting his elbows on his knees as he regarded her; "I am. Before I learned the wonders of bringing a woman to have multiple orgasms, I had a hard time pleasuring them. I was doing what I had learned off of watching porn. The purpose of porn is entertainment, not education."

Well, if he put it like that, it made sense.

Sakura sighed deeply, running a hand through her hair. If he was serious about this, she would be like a sex guinea pig. Somehow that idea both terrified and excited her. How many people would see her nakedness online, her expression contorted in pleasure?

The pink haired woman was by no means a blushing virgin. She was comfortable in her own skin. But she had never been in a situation similar to this. She wondered if she was in over her head.

Kakashi watched her face, he could almost see her thoughts dancing around her head in those bright green eyes of hers. She really was a beautiful woman. He sincerely hoped he could convince her of the benefits such an experience would bring her. He could see she was already confident with her sexual knowledge, but he was quite certain that he could boost that confidence if he introduced her to his own knowledge of pleasuring a woman.

"If it'll help you make up your mind," he added, "I can turn you into a squirter with just two fingers."

Sakura slowly lifted her gaze to his own dark one. She could see the fire burning just behind it and it made a shiver run down her spine. God help her if what this man said was true. In all her experience as a woman and knowledge as a med student, she had never been able to stimulate herself into squirting and she definitely never had a man skilled enough either.

And here Kakashi was claiming he could do it with just two of his fingers. She would take that as a challenge.

"Very well, I'll take you up on your offer..."

"But?"

"But, I have two conditions."

When Kakashi said nothing in return, Sakura sat up straighter from her seat, "First, I want you to explain exactly how I'll be getting paid for this."

Kakashi gave another one of is eye crinkling smiles; "Well, if you accept my offer, I couldn't possibly just post content with you as the star without compensating you. And people are willing to pay five figures for at least one class."

Sakura worried her bottom lip between her teeth as she thought it over. She could really use the money.

"Okay. Fair enough. My second condition would be that you tell me why exactly you wear that mask."

Kakashi sighed, "To tell you the truth, I only wear this damned thing because of my popularity amongst the women."

Sakura almost snorted at that. He was kidding, right?

"You're kidding."

"No, actually. With most of my previous classes women tended to instantly fall in love with me as soon as I showed them what they were missing out on. You'd be surprised how many women would recognize me if I were to step out in the public without my mask."

This time, she really did snort.

"It's kind of hard to keep a private life when you've pleasured over 300 women."

Sakura's jaw dropped. 300? 300 women?! Gaping like a fish, she stared at the man in front of her in bewilderment, but Kakashi could only chuckle at her. He assured her it was for educational purposes, of course.

"So, still need time on making that decision?"

"Why me, though?"

Kakashi's intense gaze never left hers. Really, it was rather obvious, "On top of being gorgeous and a wet dream for most men? It's mutually beneficial. Like I said, most women tend to fall in love the moment they experience me. You, on the other hand, don't attach feelings of love onto the pleasures of sex."

Sakura smirked playfully at him, "who's to say I won't fall madly in love and join your fan club?"

Kakashi mirrored her expression, "well, I'll just consider myself a lucky guy then."

XXX

Sakura couldn't believe she was doing this.

Shortly after Kakashi had explained his offer to her, she had agreed on being his assistant. She really needed that money.

Depending on how many times a week she would have to assist, Kakashi offered to give her 50% profits per purchase on each sex ed 101 video.

She learned that the most sought after educational video was, ironically, how to make a woman squirt. Sakura was a bit skeptical though. She had never squirted before and doubted she ever would. Studies showed that only a small percentage of women squirted when experiencing orgasm, but it could mostly only be achieved by simultaneously stimulating a woman both internally and externally.

Kakashi had argued that that statistic was most definitely incorrect and if stimulated correctly, just about every woman could squirt.

They had both agreed that that would be their very first 101 video shot together.

Kakashi had her make a list of what she had experience in and what she was comfortable with doing. He had given his word to her that they would not engage in any activity she wasn't comfortable with and she believed him.

Sakura might have felt nervous, but was determined to go into this with an open mind. Kakashi seemed confident that it would be as much a pleasurable experience for her as it would be for him and their viewers. They just had to trust each other.

If she asked him to stop, he would do so immediately. He had also proposed to have a few experimental takes in front of the video camera for her to get comfortable with the idea of being filmed whilst engaging in such an intimate act, exposing her in all her vulnerability.

The pinkette never once felt unsafe. And the whole damn thing was starting to turn her nervous butterflies into pleasurable tremors of arousal.

Her first take would be a teasing video of herself, where she stripped herself of her clothing and masturbated.

Kakashi would not join her in this video, seeing as he was comfortable with just about anything. He had added with a smirk that it would be the perfect opportunity for him to witness her own knowledge of womanly pleasure and showing him how she preferred to be touched and what worked for her.

For all of his bragging in knowing what makes a girl's world go round, he shyly admitted that only a woman knew how best to touch herself, what worked for her and what didn't. Only to smugly add afterwards that his touch always had a woman squirting in less than 10 minutes.

But his knowledge in sex was more suited for men, how best to teach a man to bring his partner over the edge and spice things up the bedroom.

When she had re-entered the living room after going to the privacy of the bathroom to ready herself for her experimental video, Sakura noticed that Kakashi had laid out a queen sized comforter over his fluffy black rug. He had placed a few throw pillows against the couch in the middle for her to comfortably lay down on, with the video camera set up on its stand directly pointing its lens toward the spot on the floor.

She had stepped out in only her underwear and she coyly looked at Kakashi through her thick eyelashes when she noticed his eyes running up and down her form appreciatively.

He had instructed her to make herself comfortable on the makeshift floor bed before he moved behind the camera to start recording.

His eyes on her encouraged her to slowly run her finger tips in feather light touches over her skin, building her own arousal up slowly. He looked like he had wanted to devour her the moment she started teasingly removing her underwear from herself, moving her right hand to pinch at her nipples whilst her left flitted down over her stomach to rub teasingly slow circles over the bundle of nerves hidden between her nether lips.

She had just been starting to get lost in the throes of pleasure, the coil in her stomach she knew as the building of her orgasm begin to pull tighter when he had instructed her to stop.

"I don't see how you could feel uncomfortable performing in front of a camera," his breathing was slightly more ragged than it had been before; "you're a natural."

Slightly annoyed that she had been denied bringing herself to orgasm, Sakura looked up expectantly at Kakashi. When he made no move to join her on the floor, she rolled her eyes.

"I'm comfortable enough, Kakashi. Let's do the first video now."

Kakashi watched her for a few seconds longer before he nodded his head. He mentioned that he would be back in a few minutes, going to prepare what they needed and that she should relax whilst she waited for him.

The burning need in her belly died down to a slow simmer of want as she waited for him, but true to his word, Kakashi had only taken a few minutes to prepare. He strolled over to her position on the floor, placing a small bottle of massaging oil, a box of surgical gloves and tissues within reach of them.

He had stripped down to just his black boxer briefs and Sakura was surprised to see him without his mask. Immediately scratching the thoughts that he might have a birth defect he was hiding, she was pleased to see that he was actually quite handsome.

He was also very well built. If she had to run a hand down his stomach, she would be able to feel the firmness of his abs. He didn't have a bulky body, he was more lean, his muscles defined.

"Ready?"

Sakura tore her eyes away from his sculpted body to meet his gaze, the simmering heat of arousal in her body reigniting into a slow burn. She nodded.

"Good. Now lean back into the pillows. I want you nice and comfortable so you can forget about your surroundings and focus on what I'm doing to you."

Sakura did as she was told and watched Kakashi through hooded eyes as he moved behind the camera again, moving it slightly forward for a close up few so he would be sure to capture every little detail before pressing the record button again.

Kakashi moved to sit down beside Sakura, gently spreading he knees open. She watched him as he pulled a surgical glove over his right hand, "Today we'll be exploring one of the most effective ways of stimulating a woman to orgasm within minutes and induce squirting."

Kakashi raised himself to sit on his knees next to Sakura, bringing her right leg up and towards him so she laid perfectly open to the audience.

"First, you want to make sure that the angle in which you penetrate her is correct. You simply measure this by feeling how her pubic bone is angled."

Kakashi moved his index finger to light trace just above the bundle of nerves on her womanhood, aligning the length his finger with the thin strip of pubic hair Sakura didn't shave off, pointing up at her face.

She gasped lightly at the contact of his gloved finger on her mound, just shy of where it felt like she needed him to touch the most.

"Once you've established the angle, you can simple run your finger down the slit until the tip of your finger is aligned with her opening," as Kakashi instructed, his hand mirrored his words and he slowly dragged his finger over her slit, making her suck in a breath as he lightly grazed over her sensitive clit. "Just make sure your finger is lubed up completely.

"A vagina usually creates natural lube, but some pussies are either wetter or drier than others. We don't want to create any painful pinching if it's the latter."

With this, Kakashi removed his index finger from her womanhood to spurt some oil over his gloved fingers, making sure to coat each and every one of his fingers completely. At the mentioning of 'pussies' in his deep, lowered voice, Sakura's inner walls rippled slightly.

After he had thoroughly coated his fingers with massaging oil, Kakashi re-aligned his index finger with her opening in the same angle he had demonstrated. She was slightly disappointed when he didn't push past her folds to enter her, instead he carried on to explain to the video camera how to correctly align two fingers.

"If you're using you index and middle finger, you want to move your middle finger to slightly overlap at the tip of your index finger. This creates a speared point to enter the vaginal canal first to avoid discomfort if her hole isn't yet ready to be stretched too quickly."

With each word, Kakashi prodded at her entrance with the tip of his fingers as he explained. Sakura sucked her lower lip between her teeth as she resisted the urge to buck her hips up against his prodding fingers.

The whole situation had her hot and bothered and he hadn't even began finger fucking her. Her breaths were slowly increasing into short, quick ones as she waited impatiently for him to start easing his fingers into her core.

He turned his palm face up.

"The motion you want to find is up and down. Not in and out," Kakashi moved his fingers in a come hither way as he explained, gently tapping against her entrance. "see the difference."

Suddenly, Kakashi was slowly rubbing small circles at her entrance, lubricating it with the oil on his finger tips, "when i go in and out," he slowly filled her with both fingers, "If she's not lubricated well enough and i immediately start jack hammering into her;" he started pumping his fingers into her at a fast pace, drawing a strained moan from her lips as she glanced down at his fingers entering and exiting her hole, her face pulling in pleasure.

"She might feel discomfort. But if I start stoking her up and down;" Kakashi immediately pushed his fingers deeply into her quivering core, moving his fingers in slow strokes in repeated come hither movements. Sakura's head fell slightly back as a long moan escaped her, her hips making minute jerks in time with his moving fingers.

"She's already building up to orgasm." Kakashi's eyes focused on her face. The pinkettes lips were slightly parted, her eyes closed against the waves of pleasure she felt with each stroke of his fingers inside of her.

Kakashi moved his ungloved hand down the inner thigh of her right leg pressed up against his naked chest. He could feel her inner walls ripple against his fingers and he wanted nothing more than to bring this pink haired beauty to intense orgasm, but he had a lesson to teach.

Kakashi slowed his fingers moving inside of her to Sakura's dismay, but gently pressed the pads of of them against her upper wall deeply inside of her, making her exposed clit push forward slightly, "The reason for this is because the g-spot is located there. you can pump away if you want, but she'll never reach orgasm by that alone."

Kakashi pulled his fingers from her dripping entrance only to replace them by the tips of his middle and ring finger, "If your hand gets tired in that position, you can simple switch over like this. It will give you a better anchoring point."

Without hesitation, Kakashi plunged his two finger back into her, pressing them against the top wall of her soaked hole. Sakura let out a startled moan before biting down on her lower lip, lifting herself by the elbows to get a better view of his gloved fingers penetrating her.

But Kakashi would have none of it. He could feel her walls start rippling more intensely around him, "you can also move to sit beside her as she lays flat on her back and bring her leg up over your neck, leaning your weight over her."

Kakashi's fingers remained deeply buried within her as he grabbed her right leg to throw it over his shoulder, scooting himself beside her on his knees. leaning slightly over her, he used his unoccupied hand to balance himself on the floor with his hand next to her left hip.

"Now you can use the motion of your shoulder to aid in your up and down stroking so your hand won't tire out." He started stroking her inner walls again with a slightly increased pace and Sakura couldn't help the breathy moans escaping her throat even if she tried. her back arched slightly from the floor.

Kakashi's breathing started to get heavier as he glanced down at the pink haired woman moaning beneath him. She had an expression of pure bliss plastered on her face and his cock twitched in his boxer briefs at the display. The direct line of vision he had of his fingers stroking her deeply inside her blazing heat made him wish he could feel that increasingly tightened ripples around his shaft in stead.

He groaned at the needy whimper she made when he pulled his finger from her; "when she's moaning like this for you, you want the keep the pace of your stroking the same. don't rip your fingers out and go rubbing her clit like mad man;" his hand imitated his word, roughly swirling circles arounds Sakura's bundle of nerves. Her hips jerked back at the sudden over stimulation on her too sensitive bud, making her gasp, but it was soon replaced but louder moans as Kakashi not to gently plunged his middle and ring finger back into her, resuming the faster pace of his stroking.

He would slow down a bit as he felt her walls tighten incredibly around his fingers so she wound orgasm before he could finish his lesson.

"And this is where the magic happens. When you feel her nearing orgasm, you speed up your pace to an almost violent jerk. And no; it doesn't hurt her. Make sure to press down as hard as you can on her upper wall with your penetrating fingers when you do this." Just when she thought Kakashi would keep her hanging on the edge of almost orgasming, she felt his fingers press down hard on that sweet spot inside of her, jerking his hand as violently up and down against her as he described. If her eyes hadn't been closed already, she was certain they would've crossed.

"As soon as she reaches orgasm you continue with this jerking, don't slow down."

Her back arched as her orgasm hit her like a tsuname, every fiber in her body felt like they were on fire. Kakashi's violent jerking extending drawing out her orgasm until she felt like she would burst. She felt the sudden urge to pee, but Kakashi's jerking didn't cease. She felt herself moaning her throat raw as gusts of liquid spurted out of her.

Kakashi gently started slowing his jerking hand to a stoke of his fingers as her load moaning turned to whimpers. She grabbed at his hand to stop his fingers moving inside her, her hips jerking involuntarily at the being stimulated whilst so sensitive.

"And that's how you get her to squirt."

XXX

A/N: I tried my best to work from memory. If I got something wrong, I'm sorry. But I feel rather satisfied with how this chap turned out.

Stay tuned for more juicy play!