Work Header

Kaguya Shinomiya and Miyuki Shirogane Wants to Lose

Work Text:

It was midnight in the springtime and two of the most prestigious students of Shuchi’in Private Academy were stuck in a battle of awkwardness! 


On the left side, top scoring of the second years and student elected Student Council President, Miyuki Shirogane!


On the right side, the thawing ice princess of Shuchi’in and all-around genius, Kaguya Shinomiya!


I-I did say that the fifth date you could do-do that, right? Miyuki felt the sweat coming off of his brow. The ABCs of love were just made up, wasn’t it?.. I knew I shouldn’t have trusted 4chan...


Miyuki did say that the fifth date was the date you can have sex. Kaguya nodded to herself, unable to put down her smile. I know you’re looking forward to it Miyuki…


Unfortunately for both, Miyuki was not looking forward to the upcoming engagement.  But to gain a full understanding of this situation, we must turn back to winter.


After their Christmas party with Fujiwara, Miyuki and Kaguya reconciled with their weaknesses and kissed under the half moon. After that, however, they couldn’t relax from the approaching challengers. Stafford and Kaguya’s father, Ganan-sama!


So they fought by the means they knew how. With heavy handed scheming and on the fly thinking, they’ve survived each battle by the skin of their teeth! But in between some of those hair-raising situations, they were able to go on dates. 


Seeing this is the fifth date, Kaguya directed (dragged) them both into a love hotel. But at the last step, they’ve lost themselves in their own thoughts!


Uh, how did they do it in pornos? Actually, aren’t those faked?! Miyuki felt like his own head was going to explode from the amount of psychological screeching he was doing.


I have done my research now. Kaguya grinned. 


Indeed! Right after her talk with Fujiwara about Shoujo Manga, she tried to research everything about sex and everything related to it! From textbook sex positions to online porn; Kaguya is now a sex scholar! 


I’ll make this a night to remember, Miyuki! She looked over to him.


What Kaguya has not accounted for is that Miyuki Shirogane is a Monster Virgin! He does not know the ways of sex or lovemaking! 


Miyuki looked like he’s going to have a mental breakdown. What are the right ways of doing this?! He gripped his side of the bed harder. I just don’t want our first time to go badly..!


Kaguya walked over to Miyuki’s side of the bed. Asking him first to have sex is embarrassing but… We both want this, so what’s there to be embarrassed about? Kaguya sat down and clasped his hand. Miyuki, still in his mental panic, looked up to see a nervous and blushing Kaguya. “You and I know that we’re both thinking about the same thing right now.” She looked out in front of them. Miyuki did the same. Windows lined the wall to show a vast cityscape. Each building lights up like a rocket, either clashing with the dark space around it or floating like debris. “So, why are you nervous right now?” She grip his hand harder.


Miyuki took a second to think out his response. “Because… Because I’m scared right now.” He felt Kaguya’s glance on him and he’s choking on air. “I’m scared to botch this.” He felt the blood coming out of their hands. He let go and took a deep breath. “Fujiwara-san already talked about our training sessions to you.” He looked at the ground and saw the same dark space that he saw outside.        


He felt Kaguya’s hand on his shoulder. “She did but…” She put her hand on his chin and moved his face to look at her. Her bright red eyes are like signal lights in the dark. “When is Fujiwara-san right, Miyuki?” They locked eyes for a few seconds before Kaguya spoke again. “Tell me the real reason.” She put her other hand on his knee. 


She trapped me but I can’t really say that I’m mad. He glanced out to the moon. Waxing Gibbous. “I’ve just heard really bad stories about boys hurting their girlfriends too many times. That’s all.”


“Still lying.” He looked back to Kaguya and he could feel the burn of her gaze along his face. She crawled onto his lap. “Tell me the real reason this time.” His ear is burning from her breath and he’s melting.


He took another deep breath. “Shinomiya. Please get off of me.” Kaguya's eyes grew wide and she jumped back to her previous spot. Then he got off the bed and walked to the windows. He heard Kaguya walk beside him. Miyuki looked down from their room to the glaring streets below. “I’m afraid of disappointing you.” He put his arm to the glass. 


“Disappointing me?” He heard Kaguya’s surprise. 


“I want our first time to be perfect.” He threw his left hand in a grand gesture. “I want to pleasure you from your body to your soul and everything in-between.”  He looked at his own feet. “But I just want to make you happy and I don’t know if I could do that.”


“You utter fool.” Kaguya grabbed his shoulders and made him look at her. His shocked eyes made her even more convinced about what she was going to do. “You being here makes me happy. What if you don’t pleasure me from head to toe? What if I get hurt from this? Miyuki, this is reality, all of these questions have answers.” She smiled. “We just have to try later. The first time is special but so is the second and third and the fourth. So please.” She pressed her face as close to his without touching. “Stop doubting yourself and do it with me.” 


And do it, Miyuki did. The lights seemed to be dimmed as he embraced Kaguya’s chance to kiss. They both felt the initial tension go away as they melted into each other's touch. Miyuki felt habit kick in and felt his arms wrap around Kaguya as she did the same to his neck.


The two sucked on each other breathless and came out for air. “Let’s get to the bed.” Miyuki pointed. Kaguya nodded and they both sat at the same spots they did before. They went back into their make-out session. Miyuki pushed Kaguya down to the mattress. Kaguya squealed with a smile. Miyuki climbed over her and then chuckled. “Remember that time in the storage room?”


Kaguya giggled with him. “Yeah. I hope Iino-san doesn’t barge into here like that one.” 


Miyuki laughed. “What would she be doing at a love hotel anyways?”


“Knocking on doors asking people to stop doing what they're doing.”


“That sounds like Iino-san.” 


Under some Sakura trees, Miko Iino sneezed. “Huh. Must be some pollen.” 


Miyuki smiled. “Let’s get back to business,” and seized Kaguya’s lips. She moaned into it and rubbed the back of his neck. Miyuki felt her hand causing blisters along his skin and he hoped he was doing the same with his hands on her back.


He was.


Kaguya pulled away to Miyuki’s confusion. “I-I think I want it. Right now.” Miyuki’s eyes widened and he jumped off of the bed. Kaguya did the same and they started to strip. Facing away from Kaguya, Miyuki took a small wrapper out of his pocket and threw it onto the bed. He could hear her dress she was wearing drop to the floor as he let his clothes do the same. He looked over- Fuck.


Kaguya was petite, no one was going to argue that but the way her body was shaped and proportioned? Miyuki felt seeing it was a sign of heaven. Helps that she’s wearing black lingerie.


Kaguya was also facing away from Miyuki and felt his gaze on her so she looked- Fuck.


Miyuki was a hard working man and that shows with his physique. He’s not muscular but he’s slim, his muscles weren’t popping out as much as Kaguya expected but even then, this… Is this the peak human condition?!  


Oh, he’s also wearing trunks. Excuse me?


“Miyuki.” The two were staring at each other for a while now until Kaguya looked down at his underwear. “I thought you wore boxers.” 


“I didn’t?” Miyuki frowned. “What made you think that..?” He pointed at her. “Wait, was this when you asked me about my favorite underwear?”     


Kaguya looked outside. “Maybe.”


“And you called me a manwhore for that?!” Miyuki threw his hands up. “I thought you were talking about your underwear!”


Kaguya looked down and put her hands on her face. “I-I wasn’t! I asked about yours because Ishigami-kun said that wearing boxers means that you’re a manwhore!” 


“Why would Ishigami say that?!” 


“Because I and Fujiwara-san caught him changing clothes in the Student Council room for P.E and he went on a rant about it!”


Miyuki rubbed his face. “Jeez, what’s with our friends making it difficult for us…?”


“Good question…” Kaguya rubbed her brow.


Amidst the still Sakura petals, Yuu Ishigami sneezed.  


Tsubame-senpai grabbed his hand. “Yuu-kun, you okay?” 


He looked up at her. “Yeah, I’m fine. It must be some pollen or something.”


Miyuki stepped towards Kaguya. “Well, that doesn’t matter anyways.” He placed his hand on Kaguya’s shoulder. “Tonight isn’t about them, it’s about us.” 


Kaguya looked up to him. “Yeah.” She said as she pulled his penis out of his underwear and started to stroke it. 


Where the-?! When-?! I can’t even think straight! Miyuki felt his head roll up to the dark ceiling. “Ah, when- ah, I- ah, I didn’t expect that-” He felt Kaguya drop from his grasp and then-


Am-am I in heaven? Kaguya dropped to her knees and started to suck his cock! “Ah, ah, ple-please don’t stop.” Miyuki moaned. Kaguya groaned in conformation and continued at her pace as she saw Miyuki’s eyes roll to the back of his head.


“Oh-oh my god, Ka-Kaguya.” He started to get feelings back in his arms so he lightly placed them on the back of her head. “I, aaah, I-” Kaguya made a wait gleasure with the hand that was holding his leg for balance and she started to take Miyuki’s penis to its base. She stayed like that for a second before she gagged and removed her throat from his dick. “Kaguya, are you okay?” He let go of her head and blushed away the hair that got on her face. 


She nodded and started to stroke his cock again. Miyuki could feel his soul leaving him again. 


Miyuki looked up to the ceiling again but tried to look at Kaguya. She looked so… beautiful, prettycutefu ckinghot on her knees and in that lingerie. Her eyes were so bright and happy and- “Kaguya, I- I’m-!” Kaguya started to deepthroat his cock again as his body rejected his soul and sent it to the moon. 


Miyuki stopped seeing stars after a few moments and found that his body was on the bed. Kaguya was off to the side with her bra off, she turned back to him and climbed to his side. “Are you okay? You got out of it when I-I-” She looked to the side with a heavier blush. “Deepthroated you.” 


Miyuki almost spit whatever’s left in his mouth. “Yeah- yeah. I think I’m fine. I thought I went to heaven for a minute there.” Miyuki whispered that last part but saw Kaguya’s head whip towards him with the brightest smile he ever saw her have. 


“Real-really?” Kaguya’s hands were on his knees. “I’m glad then… Want me to do it again?” Her voice went husky. Is my girlfriend a succubus? Since I can get used to it...  


Miyuki snapped out of his thoughts and caught Kaguya’s hands. In a smooth movement, he brought her up to his position and flipped her over, so that now Kaguya was now on the bottom and Miyuki was on top. “I do but…” He lowered himself down to her crotch. “I would feel bad if I didn’t at least try to get you to feel what I just did.” Miyuki pulled down her panties and saw what every man wants to see at least once in their lifetime.


The Vagina! An imaginable body part to boys and teenagers alike, which is represented as a small slit in most forms of media! It is a rite of virgins to treat this body part as a temple and the station of a woman’s pleasure! 


And I don’t know what I’m supposed to do..! Miyuki felt his body temperature go up and he knows it isn’t from looking at Kaguya’s surprised ( cute ) face. Do I just, do it like they do in porn and ram my fingers in? But I know that’ll hurt her so…


Miyuki lowered himself and stuck his middle finger into her vagina. ... I’ll just take it slow. Kaguya mewed as Miyuki slowly rubbed his finger back and forth. Gaining confidence, he increased his speed to Kaguya’s pleasure. 


“Mh- You’re getting the hang of this-” Kaguya gently grabbed the bed sheets. “... Would you add your ring fing-?” She moaned as he did. “Faster. Yes, yes like that.” Miyuki then curled his fingers and Kaguya felt like she was listening to him talk about stars again.        


Seeing Kaguya’s reaction, Miyuki kept at his pace. Kaguya looked like she was going to explode when Miyuki remembered something.


Actually, I don’t wanna remember the time Ryuju gave me hentai… but I think this will work...


Miyuki touched Kaguya’s clitoris and she screamed.


“Yes! Yes, like that Miyuki, oh wow, yes! Ah-Ah-!” Miyuki softly caressed her clitoris more as he continued to move his fingers at a steady pace. Before long, Kaguya screamed again. “I-I’m-!” Her body raised towards him for a second before going back to the bed as Kaguya heavily pant for a minute. She weakly wrapped her arms around Miyuki’s neck. “I-I think you gave me what you want.”


“Ye-yeah.” They locked eyes and pressed their lips together for a moment before Miyuki pulled back. “I-I think it’s time now.” He looked around on the bed. “Ah-”


Kaguya giggled and rolled to look for the condom packet. “We must’ve gotten a bit too excited.” She said as she felt some sort of plastic wrapper just rolled onto her butt. She lifted herself up and picked the item to see the condom packet they were looking for. “Found it.”


Miyuki took it out of her hands and ripped the packet open to find a small plastic ring. He took off his underwear with his free hand and tried to put the condom on the other hand but fumbled with it. Kaguya took the condom and with more ease than her boyfriend, she put it on his shaft. “There we go.” Kaguya took a breath and looked into Miyuki's eyes. “... Are you ready?” 


“Of course, you?” 


Kaguya laid back down, slid her panties right off, and held her legs wide open. “Does this answer your question?” 


Miyuki put his hands above her shoulders and positioned his dick against Kaguya’s pussy. “Very much so.” Then he entered.


They both have read that a girl’s first time might involve some pain and blood because the man’s penis would break the woman’s hymen. But…


“... Isn’t there supposed to be blood for your first time, Kaguya?” 


Kaguya hummed. “My hymen could’ve been broken by a multitude of reasons…” I can’t tell him that I've masturabated thinking about this and that’s why I’m not bleeding right now! 


Miyuki shrugged. “Okay.” He took a deep breath. “I’m going in deeper now, so tell me if it hurts then.” He did what he said. He looked at Kaguya’s face and saw a bright smile so he went as deep as he could and then out again.










“Are you okay with this, Kaguya?” He was liking this slow pace, it felt peaceful and controllable.      


“Yes, I am.”


That was a lie! Kaguya was deeply unsatisfied with the speed that Miyuki is taking! She wanted him to take her from hell to heaven to hell again during sex! But that means...


She needed him to go faster!


After a few more pumps from Miyuki, Kaguya hit the insides of his elbow which caused him to slightly buckle but that buckle was all that Kaguya needed. Using his lowered center of gravity, Kaguya pulled his shoulder and pulled him under her. 


“Bwah!? Kaguya, what are y- Ah!” Miyuki tried to protest but when Kaguya raised herself up against his shaft, his brain died. 


“President, you were going too slow for my taste… I’m sorry that I lied to you- Ah!” She dropped herself down to his base and her brain died. But it rebooted itself in a few moments and she continued to go back and down on his cock.


Miyuki’s brain started back up when she was going at a pace that he thought his dick was going to break but he can’t think about anything anymore, much less his own self-preservation.      


Kaguya bent down and wrapped her arms around his neck. She felt her ass jingle with each downward thrust, Miyuki’s ragged breath against her ear, the insane pressure within her. “I-I, ah, I hope- ah, you’re- ah, enjo, ah, ying, yourself, Mi- ah!” He hit her g-spot accidently and that made her go even faster.


Miyuki tried to nod and hug Kaguya but with the amount of punishment she’s giving him, the only thing he could feel right now is his cock. Oh, good- aaaa, god. I can’t even think str-aaaaaaight-aaa-


This went on for a good few minutes. Others who were on the same floor couldn’t focus on their own activities as Kaguya moaned and Miyuki whittered into the bed. 


Miyuki felt he was coming so he tried to warn Kaguya. “Ka- Kaguya- aaaah, I’m co-com-”


Kaguya kissed him. “I-I’m com-coming too.” Another few thrusts and the dam broke between them.


Then they both went to heaven.  


Moments later, Kaguya took his dick out of her and slumped against him. Miyuki lazily threw an arm around her. 


Miyuki stared at the blank black ceiling. “Kaguya.”


Kaguya tried to look at him but instead put her head on his shoulder. “Yeah?”


“I think I’m ready for round three.”


“Mhm, you do have a large libido.” Kaguya smiled. “I hope I can match it then.”

Due to pushing aside their problems for a night of passion, Mutual Victory.

The Next Day…


“Miyuki, you want me to wash your clothes for you when I get back home?” They started to pick their clothes from the floor.


“No, I’ll do them myself. Thanks for the offer.”


Kaguya gave Miyuki a smug smile. “Speaking of offers…”


Miyuki put his hands on his face. “No, we’re not going to go at it again right now.”


“I wasn’t going to say that. I’m just saying we should go again later. At more… Dangerous... Places.”


“You want to do it at school?!”


“There are many hidden places at the school, you know that.”


“And there are a lot of spots where you could see those hidden places!”


“Not if you position yourself correctly.”


“Kaguya, please.” Miyuki looked to the morning sun. “Also, we used all of my condoms…” He said quietly.


“So, that’s the real reason?” Kaguya giggled. “How cute.” 


“Let’s just get out of here.” Miyuki started to put on his clothes. 


Kaguya hummed in affirmation. 


They finished what they were doing and headed out to the door. “Well, Miyuki, I wonder where our next date will be?”


“Not here.” Miyuki said as he saw Tsubasa and Kashiwagi coming out of the room in front of them. 


They stared at each other before Kashiwagi said, “You guys are way too loud.”


“Excuse me?” Kaguya and Miyuki said. 


Tsubasa rubbed the back of his head. “Haha yeah, I think everybody in this building heard y’all.” 


And in that moment, Miyuki wished that he could throw himself out of a window due to embarrassment. 


Kaguya gave the couple a smug look. “That means we must be doing something right, isn’t that right Miyuki?” She looked over to her boyfriend who looked like he wanted to die. “...Miyuki?”


“Y-Yeah?” Miyuki looked at her. 


“Why are you shaking?” 


“I’m just really embarrassed.”




“Would you like to hear somebody have sex next to you?”


“Of course not.”


“Guess what? We just did that for the entire building.”




“‘Oh’ is right.”  


And in that moment, Kaguya and Miyuki wanted to die from embarrassment.


“... Are they always like this?” Tsubasa asked.


“Yes.” Kashiwagi pulled on his sleeve. “Let’s get out of here before they drag us into their problems.”