The Accidental Playboy Chapter 1: So Much for Sticks and Stones…

Author: swallowingtears

Disclaimer: No profit is being made off this fanfiction. No challenge is intended towards CLAMP, the rightful owners of the characters here.

Warnings: Rated T for very bad language and nonsexual but crude situations. Poor, poor Syaoran.

Genre: Romance/Humor. An advanced birthday present for Syaoran Li—a fic in which he is tortured. Doubt he appreciates that!

Summary: What's Syaoran Li to do when everyone thinks he's a playboy sex god—and he's quite the virgin, still blushing every time the girl he really loves, Sakura Kinomoto, comes near him? Say yes when she asks him for a very sexy favor, that's what.

Author's note: This was born from the observation that Syaoran can't control himself when Sakura is around. Add a VERY awkward situation, and—let the laughs begin!

With thanks to YamiNoTomoyo and butterflyKISSU for their help and encouragement!


They say that every boy fantasizes about being a playboy, of having a harem of girls for every sexual need, of making other men look at him with envy for the horde of women writhing at his feet, begging for a taste of him. Such carnal fantasy! Such fulfillment of manhood! They say this is the pinnacle of a man's desires.

They had never met Syaoran Li, and that was a good thing because he would have slaughtered anyone who had had the nerve to say that to his face.

Here was an eighteen year-old boy who had that oh-so-desirable playboy reputation—and he quite hated it. If he ever got his hands on whoever had started that rumor, he…well, he could get very creative with ideas for revenge (or hell, he could just pay Eriol Hiiragizawa to get creative for him—Syaoran wasn't picky, and he believed in the whole 'end justifies the means' tenet), and he fully intended to go beyond mere slaughter. No, that wasn't enough payment for the humiliation he had endured at the hands of those who thought him to be a playboy.

What was the fun in having girls harass him on a daily basis, of having people whisper and giggle whenever he passed by? He would have thought his boring life of home, school, martial arts practice would have convinced everyone that he had no social life whatsoever. Hell he hadn't even been on a real date in his life because he had never worked up the nerve to ask a certain emerald-eyed girl out. For the past seven years, mind. He was beyond being shy; there had to be a psychological explanation for this somewhere.

Why was he so pissed at a situation most boys would have given their eyeteeth to be in? Because Syaoran was quite the virgin; his first kiss had been stolen off him during a school fair when he was fifteen, and he had been furious and upset for days. He had had fantasies of giving his first kiss to the girl he loved; his mother and sisters would have laughed their heads off if they had known how he had kissed his pillow every night to practice, in anticipation of the time he would gather enough guts to tell her he'd been in love with her since he'd moved to Tomoeda at the age of ten.

Ah, his family. They were the reason why he left Hong Kong. If there was ever a collection of more perverted, mischievous relatives, he had yet to have the misfortune of meeting them. His four sisters Shiefa, Fanran, Feimei, and Fuutie loved dressing him up as a child, and then later, when he was about to enter puberty, had once actually barged in on him as he was bathing to see how far along his body was with its metamorphosis.

And his mother was no better; Yelan Li kept emailing and texting him (he had long since refused to answer the phone when he called) asking when, for the Gods' sakes, was he getting a girlfriend? Did he intend to die a virgin? He would have given his left arm for a normal mother, not one who was dying to have him mated to someone—anyone. That was vaguely insulting. Honestly!

Thank God they did not know of Sakura Kinomoto.

Their first meeting was interesting chapter of his history with her. She and he had begun as rivals—he hated her for being close to Yukito Tsukishiro, whom he'd had an embarrassing childhood crush on, but then found that over time, he began falling for his own rival. After all, who could resist those big green eyes, her sweet temperament (much to his shame she had been on the receiving end of his assholery for quite some time), her pink lips, her cute laugh, her lack of shame about her fears? God, everything about Sakura Kinomoto seemed to have been designed to turn Syaoran on, because he knew he was completely smitten with her by the time his eleventh birthday had rolled around.

How had he known? They were doing a courage test in a small cove by the sea, and she had run to him, screaming and crying, after Terada-sensei had scared her. She had clung to him, and when he'd brusquely told her to stop sniveling, she had said, "But I'm so afraid! Thank goodness you're here!"


She clung to his shirt, crying into it. "Because with Syaoran I feel safe," she sniffed.

Well, now, who could resist that?

Now he was eighteen. She still didn't know why he turned red and stammered around her (Excuses: the weather, my sandwich was spicy, I swallowed my saliva), why he was always there when she asked him to be (I'm going the same way what a coincidence!), why he had a photo of her in his locker (You make a great model for sketching, really, ask Daidouji!). Syaoran knew he was pathetic (and Eriol and Tomoyo cheerfully reminded him of it on a regular basis) but he couldn't help himself. That he didn't get nosebleeds around her was, in his opinion, quite an achievement in itself.

There was a huge problem though for poor Syaoran. When they had hit puberty, Syaoran had discovered something very disturbing: porn did not do much for him unless the girl in the movie had auburn hair and green eyes and at least superficially resembled Sakura. But then he could not get turned on because he would be furious at what the other man (or men) was (or were) doing to her. He had actually thought of going to a psychiatrist to find out why the hell he was so fixated on one girl when dozens of pretty, sexy, and willing girls threw themselves at him on a daily basis.

In the end he decided he'd rather buy Sakura a Kerokeroppi pillow she'd been eyeing for some time with the money he'd budgeted for the therapist. The smile—and the kiss on his cheek that she gave him when Syaoran handed her the pillow in front of her house—told him he'd made the right decision. He'd lived off that little kiss for days.

Hormones dictated that Syaoran would get his first erection watching Sakura at the age of fourteen going through a cheerleading routine. That had been humiliating; he'd had no idea how to hide the arousal in his pants, and he'd run all the way home when Sakura suddenly came running towards him, intending to glomp him. That had been an awful moment, and explaining later to a hurt Sakura why he'd run away had been excruciating.

His first wet dream? Hers as well; though he couldn't remember the specifics, he remembered waking up blushing and completely unable to look her in the eye for several days afterwards.

And when he did the naughty thing every teenaged boy does under the covers or in the shower? Of course he thought of her—Sakura's budding bosom soon developed into nicely rounded little breasts just the right size for Syaoran's hands, something he contemplated often—like right now, as he walked to school. Her legs and thighs were smooth and looked like they would be very soft. He often wondered what it would be like to lick that tantalizing area behind her ear, on the back of her neck, which he watched every day in school as he sat behind her. Years of sitting behind the girl he adored had not made things easier; he now could pick out her sweet natural scent from a crowd.

Once, Eriol had caught him licking his lips and thought Syaoran was drooling over Tomoyo Daidouji, whom he insisted was not his girlfriend, but about whom he was quite territorial and possessive. That had been an ugly scene, one Syaoran cringed upon remembering—but when he'd admitted the truth to Eriol about liking Sakura, he'd found an unlikely ally—and a friend.

A friend who had not teased him all the way to school today, Syaoran noted. An irregularity. Before he could ask, though, Eriol spoke. "Heads up," he said softly, elbowing Syaoran as they entered Seijyu High. "Here comes the crowd, and there I go."

"Some friend you are," Syaoran groaned. "Leaving me alone to deal with them?"

"My dearest friend, I have nothing but the highest regard for you, and there is no doubt I would face mortal danger on your behalf—but honestly, it would take a saint to put up with the sexual harassment you go through. And this is my cue," Eriol said, with a nervous glance at the lusty horde waiting for Syaoran, "to say farewell!" He quickly sped up to go to his best friend slash 'is-that-his-girlfriend-who-knows?' Tomoyo Daidouji.

Leaving Syaoran alone to face the wolves. Pun intended.

Right on schedule, they came at him. The first was quite bold. "Go out with me, Syaoran Li!" a girl down the corridor screeched. "I love you! If you take my virginity I can die happy!" Ah, a regular; Hana Kazuma. She always offered her virginity to Syaoran despite her reputation for making out with various boys in the bushes behind the gym. "Take it as a Valentine's gift!"

God, Syaoran so hated this time of year; when January entered, it was sure to be an unqualified disaster, with just about every girl (and the occasional guy) trying to hook him before Valentine's rolled around.

As he walked down the corridor, one girl caught his eye and lifted her skirt to reveal her black lace panties—Syaoran looked away, blushing. Another stuck her tongue out at him suggestively, making as though she were licking some long, hard shaft, and winked as she stuck a Post-It with her name and number on his Physics book and the invitation, "Call me for a GOOD time." He turned again to the other side, mentally making a note to dispose of the Post-It as soon as he could—which he did, sticking it onto some random boy's locker. They could have each other, as far as he was concerned.

When he got to his locker, two envelopes had been slid into it—and one had a naked photo of a sophomore girl. He turned red instantly; two years of receiving such photos had not allowed him to grow accustomed to them.

"Wow, not bad for the playboy of Seijyu, ne?" his naughty friend Takashi Yamazaki kidded him. Syaoran gritted his teeth and ignored him—something he'd gotten very good at since his sophomore year. Because Yamazaki had told him so many cock-and-bull stories (the worst being the need to burn dung incense to turn off his admirers; all it had gotten Syaoran was a week of detention), Syaoran had eventually learned not to listen to him. It was best for his sanity; besides, Sakura had never let him live down the day he'd let Yamazaki convince them that strawberries had once had legs.

He'd gotten tired of denying he was a playboy; his stuttering and stammering merely convinced others that the rumors were true. Once he thought Yamazaki was responsible. Yet the guy had not started the rumors about Syaoran; he knew this because Yamazaki had been the first to ask him what his playboy secrets were. Syaoran had stared at Yamazaki in utter shock, unable to reply (beyond the usual, "N…I…You don't…No!") and the other guy had grinned and said, "Oh, all right, if you want to keep your secrets, I respect that." He'd clapped Syaoran on the shoulder in a friendly fashion—then cheerfully spread the news that Syaoran was keeping his seduction secrets close to his chest. Oh great.

Despite his best efforts he had no idea how the whole playboy tag had started now that he knew Yamazaki was not the source of the rumors. He was beginning to consider black magic; all he knew was, girls began whispering behind his back about him when he was sixteen. Rumors of his being a sex god with a terrifyingly large, erm, weapon had boys bugging him to "let us have a look!" in the locker room and showers. Poor Syaoran had taken to showering at home as a result, terrified of being forced to undress and show his goods. To try and stave off the rumors, once cornered he'd stammered, "Uh, guys, I'm not big, I swear I'm normal! Um, small even! Yeah! I'm small! Tiny!" He held up his little finger, hoping they would believe him (he was, he felt, a nice comfortably normal sizer, thankyouverymuch).

Unfortunately this had the unwanted result of convincing the other boys that Syaoran was endowed like a horse and was hiding it, fueling the rumors even more. After that, when he walked through the halls, he would hear whispers of, "How does he hide his family jewels?" It was a special kind of hell for him, and if it weren't for Sakura, he'd either have transferred out, gone home to Hong Kong, or skipped school altogether.

It did not help at all when he was caught in strange positions with various girls and women. Once, as he was reluctantly helping the gorgeous new librarian Kaho Mizuki file some books, the ladder gave way and he fell on top of her—just as a group of freshie girls walked in. Their positions were extremely suggestive; Miss Mizuki's skirt had flown up, and Syaoran had grabbed her blouse by accident, revealing a sexy white lace bra. He had landed between her legs, and she had grabbed his head to keep him from banging it on the ladder. By the next morning, Syaoran was being catcalled by the other boys on his fast work with the sexy librarian, and he'd even been summoned by a curious principal. He had spent an agonizing ten minutes outside the principal's office, terrified Miss Mizuki had accused him of rape, when he discovered the old coot simply wanted details.

"D-details, sir?"

"Of course, my boy! How did you succeed where we all failed?" The old principal assumed an avuncular tone, patting Syaoran's shoulder reassuringly. "That Kaho has turned everyone down!"

"But sir, I swear I didn't, I don't want to go to jail, my record is going to be destroyed, I might never get to college, Sakura is going to think I'm a pervert, my family…" Syaoran babbled in a rush of fear.

The old man wasn't listening. "Ah my boy, to be your age and so handsome—Why, when I was seventeen, there was this physics teacher who…"

And poor Syaoran had to listen to thirty minutes' worth of phony-sounding (in his un-humble opinion) reminiscences calculated to get him to respond in some way. He kept quiet, and when the principal pressed him on Miss Mizuki one more time, Syaoran nearly cried. "But sir, I swear on my father's grave I didn't…"

"You won't go to jail, son," the principal reassured him. "It's the adult who would go to jail, not you, if someone reports your little sexual escapade..."

"But sir, we didn't, it was an accident, the ladder just gave way," Syaoran pleaded. But the old coot wasn't listening.

"…and since you're a boy with normal feelings, enjoy the benefits. I would suggest you seduce Miss Yuuko Ichihara next; have you seen the boobs on that babe? A handful of heaven!"

By the time Syaoran dragged himself home, he had lost his appetite (and all his respect for Principal Yamato) and was wondering what he could possibly have done in a past life to deserve this punishment in his current life.

He was in for much worse. Some of the more promiscuous girls in school, those who had reputations to keep up, had spread the rumor that he could fuck a girl for four hours straight without coming, and guarantee at least two mind-shattering orgasms per session. He'd nearly fainted when Eriol had reported that one to him. Who the hell could do that?

It didn't help that he did look like a playboy, with that peculiar mix of a very handsome, arrogant face coupled with a lean body. He was quite tall, skimming six feet, with a hard, muscled body honed from years of sword training and martial arts. His butt was hard and tight, and his skin was smooth; when he stripped for swimming class in junior year, teachers had to lock the pool area off from female (and the occasional male) gawkers—none of which, Syaoran was devastated to note, ever included Sakura.

And, not that he knew, but he was well-endowed in the region that mattered. Not monstrously, as the rumors had it—but perfect for pleasing a woman.

Syaoran just had to be the kind of handsome that turned heads; more often than not he wished he looked more normal—or had that weird ability to fade into the crowd the way Eriol did. He looked quite arrogant—because in truth he was shy and didn't care much for talking to others—and he dressed well because his Tomoyo and Eriol loved to advise him on clothing.

"How can a playboy be unsociable and completely lack charm?" he'd protested to the two.

Accustomed to his whining, the two grinned at each other. Tomoyo patted his back. "You really should get bolder and take what you want, ne?"

"Yes indeed," Eriol chimed in. "You ought to use your playboy charms to sweep somebody," and he winked at Syaoran, "off her feet and end seven or so years of mooning over her. Use your charms, man!"

Syaoran sighed. His (undeserved) playboy reputation, his looks, his good academic standing…all that didn't mean beans to the girl he had been in love with since the fourth grade. Beautiful, honey-haired Sakura Kinomoto had the ability to make him blush without even meaning to—and she had absolutely no idea what his feelings for her were.

Nearly eight years later, she was still dense, and sometimes even asked Syaoran to set her up with his friends.

God, he hated that.

A piece of fabric whooshed through the air and struck Syaoran's shoulder. He shuddered, knowing what it was. A panty. Worse, a used panty. He didn't bother picking it up.

The owner, a sexy little redhead, blew him a kiss. "Come on, make me a notch on your bedpost. I give great blowjobs. It would be an honor to have you in my mouth."

Syaoran, his ears feeling horribly hot, never knew what to say to comments like that, so he ignored them. That backfired on him all the time; it was taken as proof of his being a playboy who refused to talk about his conquests. It definitely did not help when girls in school claimed they had fucked him; somehow, someone had gotten a photo of him naked in the shower, and to his eternal shame, it had sold well in his school district. People spent free times discussing how big his family jewels were; all that could be seen in the photo was his butt, and he was horrified when, at his junior prom, he'd won the "Sexiest Butt" award.

He did the only thing he could: when the spotlight focused on him, he twitched, then bolted for the nearest exit, leaving his date (his cousin Mei Ling, whom he often used as personal armor for such events, with a hefty cash bribe involved) dumbfounded.

And now Sakura had just come up to him with the worst request she could possibly make of him.

It had been a quiet day; he was sitting in his favorite tree in the schoolyard when Sakura had jumped into the branches gracefully and landed next to him. No matter how many times she hung around him, he knew he would blush—and he felt the familiar heat creep up his cheeks towards his ears.


"Syaoran-kun!" She placed her face oh-so-close to his and smiled. "I made you bento! Croquettes and pork dumplings."

Uh oh. She wanted something, and this was a bribe. Not that he was in any position to say no—he had never been, not when it came to her. And now came his brilliant repartee to her. "Uhhh…"

Damn, damn, damn. Syaoran thanked his lucky stars that he was in Japan, where his mother and sisters could not get to him with jokes about his ineptitude in love. They would surely light a fire under his butt for this one.

"Syaoran…" Sakura sat beside him. "You're one of the guys I trust most. And you're my friend. So I need to ask you a favor."

"G—go on," Syaoran stammered. You're gonna say yes anyway, a voice in his head sniggered.

When Sakura told him what she wanted him to do to (or with) her—note the preposition—Syaoran's body began tearing him apart. His cheeks were on fire, his nose threatened to bleed, his knees wobbled, his throat closed up, and his butt won: he fell out of the tree.

Later, at the infirmary, he woke up with an almighty headache and Sakura bending anxiously over him. "Does that mean no?"

His head spinning, Syaoran croaked, "No."

"No as in no, you won't do it to me or yes, you meant no?"

"I've always hated grammar," Syaoran moaned, right before he passed out again.

He woke up again a little later, feeling slightly better—when he realized his head was in Sakura's lap. Automatically he blushed.

"I'm sorry, Syaoran-kun. I didn't mean to startle you," she said as she stroked his thick brown hair. "But…oh!" she squeaked as he scrabbled to a sitting position.

"S-Sakura," he began, "about your request…did you mean it?"

Her eyes locked on his and to his surprise, she blushed. "You're one of my best guy friends, and you've always been so nice and sweet. And—you have that reputation, you know…"

Syaoran cringed. "No, I really…I…"

Hurt flashed in Sakura's eyes. "I know I don't come up to your standards…"

"Wait…no, th-that's not…"

"…but I would like to go to college no longer a virgin. And I—I was hoping you could do the job, fit me in on your schedule…" Sakura was blushing prettily, and Syaoran was completely red. "So…could you please teach me how to…to m-make love?"

"Wh…why me?" Syaoran croaked.

She turned away. "If it's a bother, I'll…I'm sorry…" She stood up, making to leave.

It's now or never you FUCKING STUPID MORON STOP HER BEFORE SHE ASKS SOMEONE ELSE TO DO IT TO HER! Syaoran's brain screamed at him. He caught her before she could exit the door, spun her to face him, and, to both their surprise, yelled, "I'll do it! I'll DO it!"

Sakura's eyes lit up and she hugged him. "Oh thank you so much, Syaoran-kun!" She planted a kiss on his cheek, and he could feel himself beginning to slip out of consciousness again.

No. He would get through this, even if it killed him.


Next chapter: Google and Wikepedia are Syaoran's friends. Or maybe not.

Thanks for reading! Please review, and let me know what you think! Suggestions for embarrassing Syaoran further are very welcome and will be acknowledged if used!

Author's notes: First, no magic but this otherwise follows the SxS relationship in CCS. Second, sorry for not yet updating "Blossom in a Gilded Cage" but there are so many plot holes that need fixing. Third, do also check out the story I co-write with , "Manuever" (not for kids!). Fourth, I don't know if this is going to become M in rating yet, but I'd like to try a T for now, since it's mostly laughs and silliness, no angst.