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The Impossible Sakura Challenge

Summary:

Why wasn't Umemiya touching him ever since they started dating? It was driving Sakura nuts at this point. Weren't they a couple?

Then Tsubaki suggests him to propose a challenge. A challenge she knew Umemiya wouldn't win.

Notes:

HIIIIIIIIIII!!!!! i was trying to write a wind breaker fic for months, but only now i finished, well..... one! AHHAHAHHSHA it's so funny that i thought togasaku would be my favorite pairing only for umemiya to steal his spot! i wonder why there aren't lots of umesaku fics though!!!! TT

this fic is inspired by aizawa-san's (zawawa_aod on twitter) fanart!!!! their drawing was so gorgeous that i couldn't help but start frantically write HAUDHFAHFUHAD please check their art!!! i promise it's just PERFECT!!!!!!!!!! anyway......

have a great reading time!!!!!!!! <333

(See the end of the work for more notes.)

Work Text:

So, as anyone expected, Umemiya and Sakura started dating.

 

And it could be roses and rainbows if it wasn’t for the fact that, differently from what Sakura imagined, all Umemiya did was talk about his tomatoes and other cultivation stuff.

 

They were a couple, right? So though it burns Sakura’s cheeks only by the thought of it, he thought they should be doing couples’ romantic things— like kissing or even holding their hands —, but nothing really changed after they admitted their feelings to each other. The only intimate thing Umemiya did was a hug and that was the end of the story.

 

That was all Sakura vented to Tsubaki. Though it made him feel bad for telling him all of these things considering he’s in love with Umemiya, Tsubaki was the one insisting him to open his heart about what was making him feel so blue recently.

 

“Do you know what we do in times like these?” Tsubaki smiled as he knew his answer would only make Sakura blush. He knew exactly how he would react; dear Sakura was so predictable it was cute.

 

“What do we do?” And Tsubaki waved for Sakura to get closer to him— it looked like his answer was a secret, so he got closer until his ear was next to his red, gorgeous glossy lips.

 

“You should ─────”

 


 

After arguing with Tsubaki about how he just couldn’t do such a thing, Sakura gave up. He was desperate, and Tsubaki was way more experienced than him when the topic was love, so if he said it was the only effective option, then he should listen to him and just do it even though he might pass out in the process because he is already feeling his entire body tremble in anticipation. Sweating, he asked Umemiya to meet him inside the only unuseable, most private classroom in the school at night.

 

Sitting on an old teacher’s table, Sakura dangled his legs as he waited for Umemiya there. Would Tsubaki’s idea work? If it didn’t, then he would probably just embarrass himself in front of Hajime, who would probably mock him for even thinking about doing such a thing, in such a place and with him.

 

Before he could drown in his negative thoughts, the door opened and showed the tall silhouette of Bofurin’s leader.

 

“Sakura!” Like a big puppy, Umemiya closed the door behind him and rushed towards his dear Haruka. He stopped right in front of him— too close. “Why did you call me here? It’s too gloomy here!”

 

“I… I propose a challenge for you, Umemiya.”

 

“Challenge? Don’t tell me you want to spar with me here…!” Though Umemiya was very open about using the school’s places, he didn’t really think a classroom, as empty as it could be, would be a good place to fight.

 

“No, I-” Sakura sighed and took a deep breath. He only felt the temperature of his cheeks getting higher, but he remembered Tsubaki’s encouraging words. You can do it! Save your relationship! “U-Umemiya, sit there…”

 

He pointed at the chair a little bit far from the table he was sitting, though it was still in front of it. Umemiya didn’t really understand the reason why he was asking or why Sakura asked him to meet him there in the first place, still, he obeyed and waited for the next steps of said challenge.

 

When Hajime did what he asked, Sakura stopped thinking of ways to say what he needed to say; perhaps it would be easier if he showed first instead of stumbling over his words so it could all end soon. 

 

Haruka gulped before getting off from the table and standing up in front of it. With shaking hands, he put them on his pants and started to slowly lower it. When it came to the middle of his thighs, he caught a glimpse of how Umemiya was looking at him. His eyes were lost in the smooth skin showing, filled with lust like the way his mouth was open.

 

“D-Don’t say anything yet. I’ll explain the challenge soon.” With an almost inaudible voice, Sakura said before Umemiya could say something that would probably make him even more embarrassing than he already was.

 

To Umemiya’s surprise, not only Sakura was lowering his pants, but also his underwear. The classroom was silent, and it only made them more tense. When Sakura’s pants and underwear pooled around his ankles, he lifted one foot at a time to take them off entirely, tossing both pieces of clothes in a random place. Then, with cheeks almost bursting from the sheer embarrassment he felt, Sakura sat back on the table with his cock half hard twitching and wide open legs, making Hajime take a better look at his crotch as he wasn’t moving so much like before when he was taking his clothes off. When everything was settled, Haruka still couldn’t gather the courage to look at Umemiya’s face. If he looked at him right now, he might really pass out, after all.

 

“T-The challenge is… To watch me m-masturbate without touching me until I’m finished.” Sakura tried to cover his face with the back of his forearm, of course failing since not only his cheeks were blushing, but also both of his ears and neck.

 

“Sakur-”

 

“You,” Despite being curious about what Umemiya was going to say, Sakura felt the need to interrupt him again. No, he came this far. He wouldn’t stand to hear him when he’s in such an exposing, embarrassing position. After gulping in anticipation of what was about to happen, Sakura moved his hand to his crotch, his fingers wrapping around his own cock as he whimpered after the slightest touch. “You’re always talking about tomatoes or plants or whatever… And you never touch me like we’re dating. You still act like we’re senpai and kouhai from the same gang.”

 

It was like Umemiya understood the assignment of just sitting and watching his dear Sakura playing with himself. Umemiya was feeling uncomfortable even before Sakura took his lower clothes off, his cock even throbbing and twitching just by the view of him. Though he wanted to just run towards Sakura and rail him without any care, it was still a challenge. He would try not to lose. Try because deep down, he knew he wouldn’t win no matter what.

 

On the other hand, the words said with moans in the middle of the sentence didn’t let go. Umemiya tried so hard to not rush their relationship, knowing his dear Sakura easily got embarrassed from the slightest touch. Every time they talked, Umemiya would stare at his lips, knowing they would have the most delicious taste, knowing they would feel so soft and so addicting.

 

Sakura always wandered around wearing his white shirt, his neck and collarbone showing, and Umemiya knew how Togame, Suo, Kaji— damn, everyone would lick their lips from the sight of it, especially when fighting since sweat would tempt them even more. They were all friends, but Hajime wanted to crush their necks for having the guts to drool over his Sakura.

 

But Umemiya needed to be patient.

 

Sakura always wandered around wearing tight, black, pants and every time Umemiya had to be careful to not have a boner when Sakura moved his body when practicing, his legs sometimes opening so good, like they were made to be always spread open, like they were made to fit Umemiya around them.

 

But Umemiya needed to be patient.

 

He couldn’t accidentally scare Sakura with how rotten his brain was— so filled with dirty thoughts about him, all the time.

 

And, oh, the worst of all was that his Sakura was always so adorable that a lot of people grew to like him enough to follow him around, making Umemiya’s blood boil. How dare they rub their scent off on him? The thoughts were dangerous, he knew it all, but he wanted so badly to gut them from the inside out so they would never even think about getting closer to who was his.

 

But Umemiya needed to be patient.

 

Right now, though, Sakura was right in front of him, fingering his rosy, plump hole, the slick sounds getting louder with every thrust while he couldn’t even open his eyes to look just how insane he was making Umemiya. Hah, Hajime couldn’t even hide a low, discreet chuckle. How ironic was that? While he fought his arouse with his life every time he was near Sakura, his kouhai was fighting the urge to ask Umemiya to fuck him senseless.

 

Fuck, Umemiya couldn’t take his eyes off the most lewd scene he had ever seen. It was a challenge, he knew he could try to look at other things — at least, the corners of the classroom wouldn’t make his cock hard —, but he just didn’t want to lose a millisecond of what was happening.

 

“Nngh- aah…! F-Fuck,” Unconsciously, Sakura closed his legs when he felt the tip of his finger brush against his prostate. But it just… It wasn’t enough.

 

All of sudden, Umemiya was worried about his pants. His cock was so hard and leaking so much pre-come that he wondered how he would get home with a dark spot on his crotch. Thank god it was night, so maybe people wouldn’t notice it.

 

The challenge seemed endless. Umemiya’s cock was hurting so bad, he was at his limit. The classroom was filled with wet, slap sounds at each thrust. Despite trying to stay silent because what he was doing was already embarrassing enough, Sakura couldn’t stop some moans from escaping his lips even though he was biting them.

 

Still… Although he kept trying to speed his fingers, trying to make them reach his deepest spot, Sakura knew it wasn’t enough. The length of his fingers didn’t fill him up. The pace of his thrusts was all erratic since he would lose himself in the pleasure. And maybe the worst of all… His fingers weren’t hitting his prostate. 

 

Sobbing in desperation, thick tears rolling down his cheeks in shame and pain, Sakura spoke.

 

U-Umemiya…

 

The thread holding Hajime back snapped.

 

Dropping the chair backwards with how fast he stood up to stride towards Sakura, Umemiya quickly pressed his tongue inside Haruka’s open mouth, their kiss already one-sided with how hungry Umemiya was. His tongue took control as Sakura was too weak to think about how to kiss. They were both too hot, so it didn’t take too much time for them to separate from each other even though they didn’t want to.

 

“Y-You lost.” Was the first thing Sakura said when he felt Umemiya’s bulge teasing his hole, which made him whimper in the process.

 

“From the beginning, it was impossible for me to win.” 

 

While unzipping his pants just enough to free his cock, Umemiya couldn’t hold back anymore— he leaned forward so he could suck on Sakura’s neck, clavicle and all of the showing upper skin. He knew they would be hard to hide, but who cares? If telling everyone they were dating wasn’t enough to keep horny men off, then some purple hickeys would shut them up.

 

Hearing Sakura’s moans and little gasps here and there right next to his ear was the real thing.

 

Then Hajime couldn’t wait anymore. He needed to get inside or else he would actually die. He stroked his cock as he spread his pre-come on the length, sighing in relief as he lined himself up.

 

“H-Hurry up, Umemiya… put it inside already- ngh, ah!” 

 

Umemiya couldn’t even wait for Sakura to finish his sentence, so he already thrusted inside, putting his cock all in until his balls kissed Sakura’s ass cheeks. And he didn’t regret not asking if he could go in when he saw Sakura’s head tilting backwards in a violent movement as his lips couldn’t silence a loud mewl.

 

After the sudden impact inside him, Sakura gripped the edges of the table he was sitting on, feeling like he had a fever when he saw a dark spot ruining the original table’s color. However, that wasn’t the only thing making him almost pass out from embarrassment, because he could see it. 

 

He could see a little bump on his belly. He knew it was Umemiya’s cock.

 

Holy shit, was he that thin? No. The size of Umemiya’s cock around his walls told him otherwise. His lightweightness wasn’t the problem. Bofurin’s leader’s cock was just that big, so that’s why he was feeling so full, filled up so well to the point the slightest move would already be rubbing on his sweet spot.

 

“I hate that I took so long to notice that you weren’t as angelical as your appearance makes you look.” Umemiya whispered in Sakura's ear, his voice so deep and low that it only made the younger boy clench his insides around the cock that was resting inside him. “I wish that I could have fucked you the moment I saw you, Sakura.” 

 

That way, you’d know how much I held back from fucking you.

 

The dirty words coming from the silly, bright Bofurin’s leader only made Sakura moan in response. Deep down, he knew Umemiya wouldn’t be gentle like he expected him to be on their first time. He knew Umemiya wouldn’t stop even if he begged him to; that’s just how much his leader wanted him.

 

While lost in thoughts, Sakura woke up from them when he felt, inch by inch, Umemiya’s cock pulling away from his hole, leaving only the tip to rest inside him only to slam it back inside, making Sakura scream in pleasure. Umemiya didn’t even need to try to find his prostate as the tip of his cock already found it the moment it went back in.

 

“Fuck, it’s so slippery.” Umemiya’s hands moved to grip under Sakura’s thighs, knowing that bruises would probably be seen by the next hours, but needing to hold them as tightly as possible so he could keep his pace fast and deep without his cock slipping out of Sakura’s hole.

 

The classroom filled with thrusts of fingers before was now filled with loud moans and sobs, all of them mixed with the sounds of Umemiya’s hips hitting Sakura’s crotch. The stretch burnt Sakura just right, his walls clenching around Umemiya’s cock every time it went back inside him, like he didn’t want it to pull away. Though the feeling of the rough pounding into him was making Haruka even dizzier, the sound of their flesh echoing loudly in the classroom was also making him stop thinking.

 

“U-Umemiya- nngh-! Ah, ah-” With yearning hands, Sakura tried to reach for his leader, but it was too far for him to wrap his arms around his neck. “Harder-!”

 

Hajime thought he was already going too rough and hard on Sakura, but hearing him beg him to go harder just made his cock throb. Was his cute Sakura always this slutty?

 

“Keep begging for me to fuck you harder, Sakura. Keep moaning my name.” Umemiya leaned closer so Sakura could hug his neck. Pounding his kouhai wasn’t enough- he couldn’t help but suck his neck, from time to time biting it just a bit.

 

“Mmph- ‘Miya, Umemiya, ah!” Sakura couldn’t stop his eyes from rolling back as his tongue hung out of his mouth. The sensations of each rough thrust plus Hajime’s tongue was too much. His brain was beyond clouding.

 

“I’m gonna knock you up, Sakura,” Umemiya groaned with each clenching. Haruka’s insides were so wet and hot, enveloping his cock so well that he was afraid he would cum too fast. “Wanna see you walk around with my cum dripping from your thighs as you walk with your friends.”

 

“N-No- Hngh! F-Fuck!” Though Sakura didn’t want to imagine such an embarrassing situation, his body showed otherwise. Umemiya’s words indeed messed him up so good. It was a blessing to know that the puppy-like man was actually a pervert. “They’ll- ah- find out-!” 

 

“You’re so innocent.” Umemiya pulled away from Sakura’s neck to look at Sakura’s eyes, feeling his cock twitch at the sight of Sakura looking so lost in pleasure, his face blushing so hard even his ears were red. The drool escaping his mouth was also the cherry on top, as well as his sweating forehead, some of his hair sticking on it. “That’s exactly why I want you with my cum inside you. So they won’t try to steal you from me, so they know you belong to me only.”

 

It was like Umemiya’s words turned a switch on because Sakura sobbed in pleasure hearing them to the point he started to move his hips, trying as hard to meet the thrusts that sent him consecutive waves of pleasure. He knew his moves were clumsy considering he couldn’t freely move on a table, but he couldn’t just stay still. He needed more.

 

H-Hajime, please-! Break me. I want- nngh! I want you so bad…! I need more, please- please…” Sakura didn’t know what he was saying, what he was asking for. He only knew to sob, to cry because he was longing for Umemiya’s cock for so long. It was only natural that he would react that way, right? 

 

Hearing his first name being called in such a lewd tone made Umemiya grit his teeth before taking off his black jacket and white shirt. With his upper body showing, he found it cute that Sakura’s eyes were locked on it, like he liked what he was seeing. Sakura’s plea was just too much– it sent him a surreal wave of heat, so he just needed to take his clothes off so he could quicken his pace. He just needed to split Sakura open.

 

Holy shit,” Umemiya was pounding right into Sakura’s prostate, feeling like blacking out whenever he felt his cock being squeezed so well. “Haruka, just know that after this, I’ll fuck you so, so much.”

 

The sight of his cock disappearing into the hole that was already red around took Umemiya’s breath away. It was something he would want to see every day, every time he could. Even if he needed to, he wouldn’t be able to look away from it, especially considering he could see a little bulge on Sakura’s belly every time he thrusted his cock inside. Sakura looked so strong whenever he fought, yet he looked so fragile, so thin with that little bump.

 

“H-Huh?” It was embarrassing, but Sakura felt some of his insides’ fluids leaking from his ass when he heard his name being called like that by Umemiya.

 

“I’ll fuck you any time I want. Doesn’t matter if you’re with your friends. Doesn’t matter if it’s daylight.” Umemiya knew he was close. Imagining him kidnapping Sakura whenever he wanted so they could have a quickie only made his cock spill even more pre-come inside Sakura. “You won’t be able to stop me, Sakura. I want my seed inside you every day, ok? Be a good boy for me.”

 

Though he was way too lost in the feeling of Umemiya’s cock abusing his sweet spot, Sakura heard all of his words. He wasn’t sure if he would be able to handle his cock pounding into him whenever he wanted considering Umemiya was a horny dog in secret, but he wanted that feeling. Sakura knew he was too addicted to it. He wanted to be a good boy, he would behave so well. He deserves Umemiya’s cock. He earned it, after all.

 

“H-Hajime- Nngh! I’ll be- I’ll be a good boy!” Sakura’s voice looked so pathetic, his throat was aching from how much he moaned and whimpered and sobbed, but he just wanted to make sure Umemiya would understand how much he wanted to be railed.

 

Umemiya was already fighting his desire to cum when Sakura was fingering himself right in front of him, so he just couldn’t wait any longer with how Sakura looked so compliant. Unloading his cum deep inside Sakura, Umemiya came with a sharp gasp, feeling the thick, long, endless spurts of cum being buried deep inside Sakura’s hole, who also came with a needy mewl when he felt Umemiya’s cum coating his insides in white, making him feel so good, so filled up.

 

They breathed hard and in unison as they tried coming down from their orgasm. Umemiya looked like he was in a daze, his hands still holding Sakura’s thighs, like he still wanted to keep going.

 

“Nngh-” Sakura closed his eyes and let out a low moan when he felt Umemiya’s cum not only deep inside him, but also trickling out of his entrance while Hajime was still inside. His hole didn’t have enough room to fit that cock plus a big amount of cum, after all.

 

Drops of cum dripped from his hole, staining the wood floor, making Sakura blush when he saw it, slowly starting to come down from the pleasure. He didn’t really remember what he said, and he really didn’t want to remember because it was probably something too embarrassing. Now he just felt his aching body limp. Not even in his hardest fights his body felt like it was now.

 

“I’m sorry for not touching you all this time, Sakura.” Umemiya hugged Sakura, both of them closing their eyes when Umemiya’s movement also made his cock go deeper inside him. “I was holding back so much, trying to respect your limits… I didn’t even ask how you felt about it.”

 

Well… Turns out Tsubaki was right, after all.

 

“I-It’s okay…”

 

He was right, but Sakura wouldn’t do that again though. He found out Umemiya was not only a monster in fights, but also in sex. Not that he would complain about it…

Notes:

don't forget to check their account out!!!!!!! also, please, for the love of god, CAN ANYONE WRITE MORE SMUT UMESAKU?????? TT TT TT
also don't worry, i have more umsk ideas on my drafts! one of them are ntr hehe one of my fav tropes...... i hope i can write togasaku, endosaku and kajisaku though!!!! they're all cute (suosaku too, but there's already lots of fics of them....)!!!!

i love you all!!!!!!!!!!!! <333 hope you enjoyed hehe