Osomatsu

Man up, dammit! You'll never win the bet then!

Osomatsu was a guy who went for the high stakes, risking it all just for his favor. Luck wasn't just at his side, however. Six words: Never make a bet with Chibita. The dude was actually smart, smart enough to make a bet that would scare Osomatsu. And damn, he was good at it.

The bet was to kiss [Y/N] by Tuesday.

If it was a different girl, Osomatsu would've just got it over with already and accepted the damage to his face. It would've healed one day. But this was [Y/N]. A girl he really really liked, so he wanted badly to not mess this up. He would be lying to Chibita if he straight-up told him he has no feelings for the girl. Of course he does!

But Osomatsu won't give up, for the sake of his pride! What's a man without his pride?

The prize was tempting too, Chibita agreeing that he will lower the tab a bit if he manages to kiss her, with the addition of him wearing a dress for a whole week. Let the games begin...

---

Nothing was working. Osomatsu tried every way to discreetly kiss [Y/N], only for all of his attempts to miserably result in failure.

Osomatsu tried the pocky challenge. Jyushimatsu finished off the pocky instead. Osomatsu tried the 'clumsy-accidental-first-kiss' act. He kissed the ground instead. He even attempted ways for the two to indirectly kiss, even failing at that. It was like an invisible barrier was just casually surrounding her, protecting her from every lame attempt and poorly planned schemes Osomatsu comes up with in only the span of seconds.

Time to throw in the towel...

It was Tuesday, the deadline of the bet and Osomatsu was empty handed, sighing painfully as he slowly walks towards Chibita's oden cart, ready to admit defeat.

On the way, out of the corner of his eye, he spots [Y/N] taking a leisurely walk, carefree and slightly upbeat. [Y/N] seems to notice him and immediately waves her hand at him, catching his attention.

"Hey, Osomatsu! Do you want to walk together?" [Y/N] suggested as she stops mid-stride, making Osomatsu think over it.

He's pretty much lost the best, so a bit of fun before he gets humiliated was fine in his book.

"Sure [Y/N]-chan!" Osomatsu accepted the invitation as he grinned, taking his place next to her.

"So...where were you originally going to?" [Y/N] questioned as the two started walking, fiddling with her fingers.

Arms crossed behind his back, Osomatsu sighed out loud, deciding that she deserved to know. "Just dropping by Chibita's. Lost a bet." Osomatsu muttered out the last part, a bit ashamed to admit it.

"You losing a bet? You're kidding, right?" Slightly shocked by the news, [Y/N] stopped in her steps, looking at Osomatsu with wide eyes.

"What can I say? He makes really tough bets..." Osomatsu explains, adding a playful wink at the end for good measure.

"What was the bet even about? For you to kill a man? Actually, that's easy for you, to be completely honest." [Y/N] grumbled.

"I'm hurt [Y/N]. You make it sound like I'm heartless." Osomatsu faked a hurt expression, placing his hand over where his supposedly nonexistent heart would be.

"Yeah right." [Y/N] snickered. "But seriously, what was the bet about?" Still curious, [Y/N] presses Osomatsu, making him nervous since he's fresh out of ideas to dodge this question.

"Guess the cat's out the bag. I was actually suppose to...kiss you..." The smile on Osomatsu's face faded as he blushed, his famous shit-eating grin officially gone now.

Even [Y/N]'s smile faded and suddenly turned dead serious, contemplating about something.

"Uh, don't think that I'm a pervert! Well, I am a pervert, but still!" Osomatsu blabbered out loud, holding up his hands in defense.

"So is that why you've been acting weird for the last couple of days?" Oblivious to his past behavior, [Y/N] questions him.

"Um, basically." Osomatsu awkwardly mumbled out, fearing that he messed up big time. (A/N: BIG TIME RUSH)

What was unexpected was that [Y/N] gently cupped his face, gently biting her lips as she makes a decision.

The warm feeling of lips on Osomatsu's own lips felt...nice. He couldn't come with much else, considering that his mind-if he had one-was malfunctioning from this new sensation and blissful feeling. It was shortlived, however, when [Y/N] pulls back, gracing a playful grin on her lips.

"What would've happened if you lost the bet?"

"...I would've been in diapers for a week..." Osomatsu slightly winced as laughter met with the end of his sentence.

Karamatsu

(A/N: I'm writing this last. Poor Karamatsu)

"My dear, isn't that perhaps a bright shade of lipstick you're wearing?" Karamatsu states as he stares at the bright bold red and strangely alluring lipstick on [Y/N]'s lips.

"I'm trying on make-up just for today. I'm already regretting this decision..." [Y/N] sighed.

"My Karamatsu Girl~ Have no fear, because you're already perfect the way you are~ There's no need to change any aspect of your life just for the sake of perfection~" Karamatsu coolly said as he winked, giving a charming smile to [Y/N].

"Thanks Karamatsu. This is not permanent though. I just wanted to feel how lipstick is, but red was the only color I had." Unaffected by his painfulness, [Y/N] embarrassingly confesses her real intention.

"Hmph. Anything looks good on you~" Karamatsu proudly complimented [Y/N] once more, making her blush.

"Stop. Flattery will get you nowhere..." [Y/N] looked away, her sakura blush matching the red of her lipstick.

"But it's worth it to catch a glimpse of your beautiful blush~" Karamatsu kept at it with his endless streams of compliments, still smooth as ever. The effictiveness on [Y/N] was surprising, proven from her ever-growing blush, but her naive nature probably doesn't count.

But Karamatsu slowly becomes more vague with each compliment, unusual since his flowery speech fit for a master poet was never not detailed at all. He's a dork, to put it plainly, but an adorable dork.

Which can explain why he stares at the bold red lipstick painted on [Y/N]'s lips, getting thoughts that are ideally not the ones of a gentleman.

His lips were, embarrassingly, the lips of a virgin still, never have touched or come in contact with another's lips. He couldn't say the same thing to his brothers, though, since there was that one time they all got ill...

But the more Karamatsu listens to [Y/N]'s rambling, the more sweaty he gets, clenching his sweaty palms into small fists while [Y/N] continued to complain about her parents.

"I wish your mom was my mom, considering how nice she is compared to my naggy mom." [Y/N] huffed out as Karamatsu vaguely nodded, staring at her lips. How easily he can imagine his virgin lips crashing against her crimson red lips...

But a woman is a work of art that is meant to be treasured and properly taken care of, something you don't take for granted like most despicable men at this time. So of course they should be treated with the respect they deserve, proper men being the only group that seems to understand this perfectly logical philosophy. Woman have done so much, so who's to say one sex is far more superior than the other when they should be treated as equals?

[Y/N] sighed, her lips unintentionally parting a bit in way that Karamatsu could describe as an act of a true goddess.

Without any warning, Karamatsu gently presses his now non-virgin lips against [Y/N]'s lips, clamming up her rant for now.

Karamatsu sighed quietly in the kiss while his shaking hands gently threaded through [Y/N]'s hair, making sure to keep his hands busy and his cool composure up. [Y/N] seems to like this bold side of Karamatsu and gently wraps her arms around Karamatsu's neck, a positive reaction out of her as Karamatsu's confidence increased.

Soon getting breathless, Karamatsu gently pulls back, a dreamy look on his face while a crimson red lipstick stain was currently present on his lips, earning a small giggle from [Y/N].

Choromatsu

Oh god, this is so humiliating...

Choromatsu nervously glanced around the area, hoping that nobody will come across his questionable search displayed on the computer.

'How do you kiss someone?' was clearly typed on the search bar, with thousands of results loaded below, ready to be clicked on. (A/N: I'm scarred after finding a website to research for this)

There was literally nobody that Choromatsu can rely on for love advice, no one! Even his own mother would be a bad option, just with her in a somewhat (?) divorce and her neverending teasing. Choromatsu will never be able to live down to it if he admits to his brothers that he was in love. No way in hell! His life was already a mess.

So what's the next best option? The Internet of course! He's going to research as much as he can before someone catches him.

---

"Uhm, Choromatsu? Are you okay? You look terrible, plus there's a large imprint on your left cheek..." [Y/N] inspected his face, full of concern for him.

"It's nothing!" Choromatsu slapped his left hand over the strange imprint, cringing as his voice shifts a bit, cracking to a small squeak. The large imprint on his left cheek was caused from him falling asleep flat on his left cheek on the keyboard while researching. Of course, his brothers caused a commotion early in the morning that Choromatsu had to fix, as usual. So living off a few to none hours of sleep proved to be quite honestly tedious

"Alright Choromatsu...but don't blame me when you drift off into space..." [Y/N] lets it go for now, still clearly concerned.

"C-Come on. We're supposed to hang out today." Choromatsu awkwardly added, planning for the 'date' to end with a thoughtful kiss.

---

Don't panic.

"Choromatsu?"

Okay, panic now.

Choromatsu had crammed a bunch of paper notes in his hoodie pocket in case he needed a quick reminder of what to do as he recalled some stages of a proper date. He was trying really hard to make this as perfect as he can possibly make it, even going all out with mints and mouthwash in the morning.

"Choromatsu."

Okay. So first things first, you have to set the mood. Then make physical contact with your partner, making sure they are read-

"Kermit." [Y/N] slightly shook Choromatsu's arm, snapping him out of his thoughts as she used a nickname he despised.

"What are you worrying about? We're just on the balcony, yet you're on Cloud Nine right now." A bit exasperated, [Y/N] looks at the sunset once more.

Oh. That's right. The two were just watching the sunset from the balcony in hopes of it being a decent place to kiss at.

"Hey...[Y/N]..." Choromatsu started, feeling smaller as the moment came closer.

"Hm? What is it Choromatsu?" [Y/N] cocked her head to the side, anticipating his next words.

"Is it okay if I...research on you?" Choromatsu closed his eyes shut, nervous with the giant mob of butterflies fluttering in his stomach.

"Research?" Unsure what he's exactly saying, [Y/N] repeats his unusual word choice.

"Like....t-this..." Choromatsu breath hitched as he gave a small and quick peck on her lips before pulling away at once, finally doing the deed.

[Y/N] immediately closed the space between them and kissed him again, holding his hand to prevent him from escaping.

T-This wasn't part of the plan!

Choromatsu tried to focus on the kiss, shakingly snaking his arms around her waist as he hesitantly kisses back.

It actually felt more satisfying than a second long kiss, but all things come to an end as [Y/N] pulled back, smiling.

"Are you wearing chapstick?" [Y/N] teased as Choromatsu sweats, getting called out.

Ichimatsu

Dammit [Y/N]...what are you up to?

One of his close cat friends just communicated with him, handing him troubling news of [Y/N] kissing a man.

He wasn't mad though. All he did was punch a few holes in the wall and flipped all the tables in his house, nothing major.

Okay. So he was mad. Outraged, to be fair. Jealousy was something that early overtook his emotions, making him act before thinking of the obvious consequences that were induced on him later. Once he starts, it takes a while for him to finally calm down and quickly figure out what's going on, awfully similar to Totoko.

"[Y/N]..." Ichimatsu whispered out, his almost nonexistent heart throbbing painfully.

---

How can she be so calm?!

[Y/N] was presently visiting him, gently stroking one of his cat friends as she cooed out small little praises to the little guy. Ichimatsu was just sitting near the two, watching and silently counting the number of strokes [Y/N] had given.

It was annoying how normal [Y/N] seems to be, even if she really had no use for garbage like him now that she kissed a guy. Ichimatsu started boiling with anger, loosing his current count. He wanted to kill that guy. He wanted to get rid of his competition. Wait, competition? For what? For... [Y/N]? He doesn't stand a chance against all the suitors that are surely fawning over her. He's nothing. He's trash. A piece of hateful trash.

"Ichimatsu, are you okay? You seem...out of it today." [Y/N] stopped running her fingers through the cat's fur, putting all her attention on Ichimatsu.

That's it. The final straw. Even if he can't be that close to [Y/N], he wants to at least kiss her once before their relationship gets screwed up and Ichimatsu goes back to being the pathetic virgin NEET he is.

"...You know what I think?" Gathering up his courage, he turned around and roughly slammed his lips against her soft plump lips, earning a surprised yelp from her. But he didn't care. He only focused on the inexperienced way he moved his lips against hers, surprisingly enjoying the sloppy kiss. The cat jumped out of her arms, sensing the tense atmosphere as it jumps out the window, witnessing an uncomfortable scene.

After some time, he pulled back, his brows furrowed as his expression contorts in anger.

"Why am I even sticking in your life now?!" Ichimatsu demanded out loud, secretly hurt inside as he clenched his hands into tight fists.

"H-Huh!? What do you mean?" Dazed from the surprise kiss, [Y/N] couldn't process his words.

Is she serious? "Don't play dumb. One of my cats told me that you kissed a guy. Are you planning to get rid of me?" Ichimatsu suddenly got to the point, his fists shaking a bit.

"I kissed a guy?" [Y/N] cried out in surprise, eyes widening from his proclamation.

"My cats saw you at the park being friendly to a man yesterday afternoon."

Hopefully she'll remember...

"That?! That was my father!" [Y/N] yelled out loud, in disbelief.

Father?

How embarrassing. Ichimatsu's cheeks flared up, suddenly realizing what he had just done. He kissed her, kissed, and she knew that he was jealous. He really badly wanted to just crawl in a hole and die.

"Ichimatsu...were you jealous?" [Y/N] gently held his hand, making sure he didn't escape.

"...Mmm..." Ichimatsu looked away, a bright blush on his face now.

Jyushimatsu

"Isn't this fun [Y/N]-chan?!" Jyushimatsu inquired as he gets his trusty bat ready, itching to swing it already.

Panting and huffing, [Y/N] was pooped out from all the earlier exercises the two did together. "I-I'm a bit tired, but I'll survive."

"It's getting late, so how about just one more throw?!" Jyushimatsu insisted as he automatically positioned himself into stance, just not ready to call it quits now.

"Okay!" [Y/N] agreed as she held the baseball in her grasp, ready to pitch.

[Y/N] is so strong!

With that, another thought passes through Jyushimatsu's head, making him stop for once and listen.

I wonder how Homura-chan is doing right now?

No. Don't think of that. Not when you're about to bat.

But, is she doing okay over there?

Last time Jyushimatsu checked, he remembered that her parents supposedly didn't like her, maybe disappointed in her. But how can they be disappointed in her? She's an amazing person, more amazing that Jyushimatsu can ever be.

The same thing can apply to his dark and gloomy nii-san, since he's so much more than he thinks. Everybody was special in their own way, even Totoko, the struggling idol that loved herself.

You could say Jyushimatsu had three special girls in his life. Totoko, his childhood friend, Homura, his temporary love, and... [Y/N].

Jyushimatsu had this wild beating in his chest whenever he's close to her, afraid that his heart might explode at times.

He might actually have a chance to be close to her, considering how he can actually reach out for her and touch her, while the other two were impossible to stay with. They were unreachable.

This feeling...

"On three! Three!"

What do you call it?

"Two!"

Is it really...?

"One!"

Distracted, Jyushimatsu gets a baseball pummeled straight to his forehead, collapsing backwards as he lets out a small groan.

"Jyushimatsu!? Are you okay?!" Worry etched into her features, [Y/N] immediately runs to his spot, managing to have the strength to run across the field for him.

Jyushimatsu rubs his now bruised forehead, laughing a bit with his wide smile.

"I love you!" Jyushimatsu outwardly confessed out of nowhere as he gave [Y/N] a big smooch on the lips.

"J-Jyushimatsu!?!"

Todomatsu

"[Y/N]-chan, you look like one of those sad but adorable puppies at those store windows~" Todomatsu teased as he pulls up a picture of, indeed, a sad puppy on his phone, facing it to her. [Y/N] only puffs out her cheeks in frustration, still not able to deal with Todomatu's excessive teasing the proper way.

"That's not funny Totty~!" [Y/N] countered as she placed her eyes on the item she desired. Hot chocolate.

[Y/N] had a sweet teeth, that was obvious with the way she ogled at sweets in display. Hot chocolate was no exception, so it's almost impossible to not see her eyeing at the delicious beverage.

Who wouldn't if it was chilly outside and your friend had a promising cup of hot chocolate on the table, the wafting aroma deliciously making anyone drool on the spot? Even better, the thin sheet of marshmallows melted along with the hot beverage at the top makes it more tempting.

"Totty, can I have a sip~? Pleaseeee~?" [Y/N] whined as she drummed her fingers against the table in anticipation.

He chuckled in amusement as pulls his pink phone away, seeing her attitude change so quickly.

Maybe he should tease her just a bit more.

"Alright [Y/N]-chan," She slightly brightened up, looking at him in hope. "But let me first have a sip~" She then deflated, pouting more.

"But Totty!" [Y/N] objected, only to get cut off as he wags his finger.

"Ah ah ah, you have to be patient [Y/N]~" Todomatsu interjected as he slowly took a sip from the plastic cup, humming as he feels the warm and delicious chocolatey liquid run down his throat. It was a pleasant feeling, that's for sure.

[Y/N] had her hands out, cupped and expectant. He only sighs, not wanting to stop the fun yet.

I might get slapped for this, but..

"Okay [Y/N], here you go~!" Todomatsu sets the cup on the table, momentarily confusing [Y/N] as he leans in, kissing her sweetly. [Y/N] freezes, not expecting the turn of events as Todomatsu continues, the taste of sweet chocolate lingering in the kiss.

Todomatsu gently pulls back, nervous to see her reaction.

"Y-You can keep the rest!" [Y/N] stammered out as she pressed her cool palms against her red cheeks, wildly blushing.

Todomatsu smiles, the winner of this round. "Thanks~" He chirped out as he took another sip.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

(A/N): I apologize for any writing mistakes, grammar mistakes, errors, plain writing, or any seemingly repeated themes.