Chapter Text
Koneko sat in silence inside the occult research room as she contemplated her situation once again. She had tried to have sex with her boyfriend last night and, as per usual, he had barely been able to fit inside her pussy. She had tried every position they could think of but none worked.
There were many reasons for this, the first of which being Koneko’s height, or lack thereof. She was only 4 foot 6 in height and, despite having wide hips and a very fat ass, she was not well developed. The second issue was her boyfriend.
They had met in an arcade and had simply connected really well from there. He was pleasant to talk to, funny and was fine with her blunt personality. These were all great things. It did not help, however, that he was 6 foot 5 in height and had a cock that was longer than her forearm and just barely as wide as it. These factors combined made it nearly impossible for her to fit him inside her pussy.
She sat, staring at the table in silent contemplation until she turned around and saw Akeno standing behind her. Raising an eyebrow she looked in confusion at her before saying, “What’s up?”
Akeno merely brought a hand to cover her lips as she giggled and said, “Still having bedroom issues?”
Koneko immediately blushed a bright shade of red and, before she could ask how she knew, Akeno interrupted her and said, “It’s fairly obvious that he’s too tall for you. He simply would not be able to fit into your pussy, you know.”
Koneko, still blushed red, looked down toward the table again before she mumbled, “And you’ve got no solutions, cow tits.”
A tense silence filled the clubroom air as Akeno took a quiet sip from her nearby teacup and bluntly spoke to Koneko. “Why don’t you try anal?”
Koneko began to sputter as she blushed an even brighter shade of red before yelling, “What the fuck!?”
Akeno smiled at Koneko before bringing a finger to her chin and saying, “He should be able to fit up there, no? There’s no limit to what can go up there unlike your pussy. That and your Rook durability should make it less painful.”
As she heard what Akeno was saying Koneko began to hate herself. She hated herself because she found herself agreeing with Akeno. She realistically could hilt him like she had always wanted if he fucked her ass. She looked away from Akeno at the table before quietly asking her, “Do…you know how I would go about this?”
Akeno grew a sadistic smile as she stared at Koneko. She knew that she now had the chance to help her friend experience something she greatly enjoyed as well.
And that's how Konkeo found herself as she was now. Naked on her bed, with a cleaned out asshole and a bottle full of the underworld's best lube ready to be used. Her fat ass was compressed into her bed as she tried to work herself up to this. Akeno promised it might not be pleasant, hell it could even be painful, but this was something she wanted to do.
Soon, she heard her front door unlock as her boyfriend arrived, she heard his voice announce his arrival and so she told him where to go. As he opened the bedroom door and stood in shock at the sight of Koneko naked on the bed, she began to speak to him.
She looked him dead in the eye before saying, “I know we’ve had…issues, in the past when it comes to sex. But I think I’ve found a solution.”
He quickly shook his head before saying to her, “Koneko, I don’t date you for sex. I’m here because I love you. Even if we’re never able to have sex I’m going to stay with you.”
She grew a small smile at the declaration before she shook her head and told him, “I know that, and that does make me happy. But I know a way we could have sex and not struggle to fit you all inside me.”
He stood silently there, before he gave her a cautious nod. She then took a deep breath, before she turned around away from him and lay down on her front. She then brought the heels of her feet to rest underneath her ass before grabbing her fat ass cheeks and spreading them wide, exposing her tight pussy and, most importantly, her asshole.
He seemed to immediately understand what she was saying as he quickly shook his head before saying, “Koneko, I love you, but there’s no way I’m gonna be able to fit in your ass. It’ll be even tighter than your pussy!”
She turned around to glare at him over her shoulder before saying in a deadpan tone, “Most guys would be on their hands and knees begging to fuck their girlfriends ass, you know?”
He shook his head as he rolled his eyes and said back to her, “Most guys wouldn’t break their girlfriends ass wide open if they did, you know?”
She took a deep breath before staring at him in the eye and saying, “Look, even if this doesn’t work. I just want to try, ok?”
He looked around a bit before sighing and nodding his head. He quickly began to disrobe and soon enough he was standing naking behind her with his massive erect cock pointed towards her asshole. He stepped up behind her ass and crouched down so he could rest his massive length along her back. Feeling the tip of his cock touch nearly halfway up her back made her gulp in nervousness but she was committed.
As his cock rested on her back and was sandwiched between her fat ass cheeks, he said to her, “Are you absolutely sure you want to do this?”
She nodded her head before pointing at the bottle of lube resting on the bedside counter. He signed before reaching over and grabbing the bottle. He then began to pour an extremely generous amount of the lubricant over the length of his cock and rubbed it into his length. He then poured some onto Koneko’s asshole which caused her to jump slightly as her asscheeks wobbled from the sensation.
As he lined up the tip of his giant cock with her puckered hole, he said to her one final time, “Do you think you can do this.”
Koneko was silent for a moment before she spread her ass cheeks even wider than before and said, “Please Fuck my ass.”
He nodded his head before saying to her, “Just tell me if it hurts too much, alright?”
She nodded her head as well before pressing it as hard as she could into the bedsheets in preparation. Soon, she felt the tip of his enormous cock begin to press against her tight ass and apply force. She grit her teeth and closed her eyes as she felt the pressure begin to build and build against her asshole.
The pressure slowly began to build more and more as he leaned in further and further. Her grit teeth and sharp breathing soon turned into groans of pain and pleasure as her asshole began to ever so slowly cave inwards. It was a battle between his giant battering ram and her anal gates and she was slowly losing this battle.
He didn’t want to apply too much pressure as if he did then he might accidentally go too deep too quickly, but he also had to not apply too little pressure as otherwise he’d never get inside of her. Such was the constant battle that raged of finding the right amount of pressure to apply.
Eventually, after minutes of trying, Koneko’s ass began to yield. She could feel the lube from his cock pushing into her ass and she knew this would be the final step. Sure enough, after she thought this and finally relaxed enough, the head of his giant cock pushed through her anal ring and came to a stop inside of her guts.
Immediately, Koneko jolted and tensed from the sensation. It felt like nothing she’d ever felt before. It felt like she was trying to take an entire arm up her ass. Despite that, however, she was surprised to realise that she was feeling pleasure from the sensation of being stretched so wide. It was still very uncomfortable, but also pleasurable.
Koneko let out a long string of groans and moans as she felt her ass adjust to the girth of the cockhead inside of it. She also felt her boyfriend begin to rub and caress her ass cheeks and the small of her back in comfort. He then said to her, “Are you alright, Koneko?”
She took a few deep breaths as she tried to relax before letting go of the hold she had on her fat ass. She then reached up next to her head, grabbed the bed sheet as hard as she could and looked at him over her shoulder before telling him, “I’m ready, just be gentle.”
He nodded to her and, as Koneko turned around and buried her face into the bedsheets, he began to slowly inch his cock forward. Immediately muffled moans of discomfort and pleasure emerged from Koneko as his cock began to glacially travel further into her guts.
He could see and feel her asshole clenching and straining as he gently pushed further inside her tight rear. There was constant resistance from her insides as they gripped his cock despite the copious amounts of lube they had used. Still, he pushed inside at a slow, steady pace. The sight of his cock disappearing up Koneko’s ass was extremely arousing, however.
Meanwhile, Koneko was barely able to register any sensation bar that of the cock currently reshaping her guts. It felt like she was being excavated by a giant pillar of hot meat that refused to yield as it traveled further and further up her ass. She felt her guts yield and give way as the unrelenting force of his cock continued to travel deeper. In spite of the discomfort, however, she found herself moaning at the sensation. It felt good. She could not believe how good having her ass destroyed by an arm thick cock felt.
Eventually, once half of the giant cock came to rest inside of her tight ass, he stopped pushing inside. The two began to breathe deeply as they tried to regain their calm and adjust to the sensation. This was the farthest he’d ever been able to push his cock inside of Koneko.
She looked over shoulder at him in confusion as he reached over to grab the bottle of lube again. She quickly pushed her face back into the bed and began to moan, however as he slowly began to pull out. He began coating more of his cock in lube before pushing it back in. Koneko moaned from the stimulation as she could feel the head of his cock pressing against her womb. She could feel her arousal dripping down onto the bed from her pussy as the intense anal was also applying pressure onto her pussy, causing even more pleasure.
Once he was finished re-lubing his cock and back halfway inside of her ass, he began to push forward again. The glacial progress of his cock continued as Koneko gripped the bed even tighter. She could not believe how good this felt in spite of the discomfort. The sensation of every bump on his cock sliding past her asshole, the unrelenting force of his cock pushing into her guts, the overwhelming mental pleasure of her finally being able to take his cock inside of her. It was heaven for Koneko and soon her moans began to grow louder and louder despite how muffled they were.
As he pressed into her ass, soon, only a quarter of his cock was left unhilted. He couldn’t believe his eyes, Koneko was actually taking him all the way up her ass. He pressed on with this amazing sight, desperately wanting to see the outcome of this. His cock continued to travel further and further into her guts. If he could see her from the front he would be able to see the faint outline of his cock as her stomach bulged from the extreme insertion.
Eventually, with the gentle sound of flesh meeting flesh filling the air, Koneko’s fat ass now lay flush with his hips. His cock had been fully sheathed inside her tight asshole. Koneko felt the impact of his hips against her ass and could not believe it. She could feel his balls clenching as they rested against her pussy lips and hear both him and herself taking deep, gulping breaths of air.
So surprised was Koneko by the sensation, she didn’t even notice the pleasure that had slowly been building and building until it reached its apex. Her entire body clenched down around his cock hard, her eyes went vacant and her back arched as she looked up to the ceiling in shock. She had just had the best orgasm of her life.
Her boyfriend was scared by how hard she had just clenched until he felt how wet his balls had become as this happened. Reaching down, he could feel how wet her pussy was as her ass continued to clench and unclench, as if it was milking his cock inside of her.
He looked on in astonishment before he asked Koneko in a gentle tone, “Did…did you just cum?”
Koneko relaxed into the bed and began to take desperate breaths of air. She lay there for a moment before she whispered to her boyfriend, “I think I might like anal a lot.”
She wiggled her ass after saying this and moaned at the sensation of his cock pressing against different parts of her body. She was so happy to discover this, finally, she could have sex with her boyfriend properly. Even if it was with an unintended hole.
He rubbed her ass with a gentle caress before saying to her, “I love you, Koneko.”
A blush covered her face as he said that, she looked around with a pout on her face as she said, “You say that after turning me into a shishkebab, dummy.”
He let out a gentle laugh and Koneko blushed even harder. How could he still be so cute even while coring out her asshole? She turned around again to hide her blush before she mumbled to him, “You can start now, if you want.”
He smiled at the sight of Koneko trying to hide her blush. She really was the best. He then let out a sigh before gently grabbing her wide hips with both hands and beginning to pull out. Koneko immediately started shaking and moaning as her ass kept trying to hold it’s grip on his monster cock as he pulled out. Her asshole stretched as his cock pulled further and further out. It was only once the head of his cock was the only thing left inside that he began to thrust back in.
Koneko was left an incoherent mess by this point. Why did anal feel so good? It was the only question she could ask herself as his giant cock began to push through her guts again. The sensation of stretching, the feeling of her insides parting to let him through, the fact he could actually fully fit inside of her. This was perfection. As her fat ass clapped as it made contact with his hips, she let out a loud moan from the sensation of being hilted once again.
Soon, the thrusting inside of her guts began to speed up to a more steady pace until, instead of taking a full minute to push inside then another minute to pull out, it was now less than a minute for him to push inside her and pull out. Koneko was now constantly moaning as the sounds of her fat ass clapping against his hips and the feeling of his balls smacking against her pussy drove her over the edge once again.
She yelled out even louder than last time as her eyes rolled up and her tongue rolled from her mouth. She squirted against the bed as her ass turned into a vice around his giant cock. He stopped thrusting as his cock was locked in place from how hard she had started to clench while cumming. Soon, she fell against the bed again and tried to start drawing desperate breaths once more.
Soon, once she had caught her breath, she noticed he wasn’t thrusting and turned around to look at him in confusion. She asked him, “Why’d you stop?”
He reached a hand behind his head before saying, “I’m fine doing this to make you enjoy it so I want to do this at your pace. I feel like if I keep thrusting harder I’m going to hurt you and I don’t want to do that.”
A frown and blush grew on Koneko’s face at his response. The considerate idiot didn’t want to hurt her, he says while shoving an arm sized cock up her asshole. She began to think of what to do in this situation before taking a deep breath, grabbing both of her fat asscheeks once again and spreading them. She then made eye contact with him and, with as much authority as she could muster up with a cock half buried into her guts, told him,
“Fuck me. Fuck my ass as hard and as fast as you can until you fill my guts with your cum.”
His face grew serious before nodding. He grabbed her hips once again but this time even tighter than before. Koneko quickly reached over the bed to grab a pillow to bury her face into before reaching back and spreading her ass again. She looked back over her shoulder at him and said to him, “Do it.”
She didn’t even have time to react before he quickly thrust the rest of his length into her guts. She slammed her head into the pillow and let out an ungodly moan of pleasure as her ass was cored out in a single thrust. Before she even had time to adjust he was pulling out and then shoving his giant cock back up her ass.
The sounds of flesh meeting flesh filled the air as he thrust as hard and as fast as he could into her ass. Koneko was a mess as her feet and toes clenched and twitched, her eyes were unfocused and her hands were almost tearing through the bedsheets with how hard she was grabbing them.
He marveled at the sight of his giant cock emerging and then rapidly plunging into Koneko’s tight rear. Her ass was bouncing and jiggling from the impact of his hips against her rear and he could feel her wetness every time his balls pressed against her pussy. As he thrust harder and quicker, the resistance in her ass began to lessen and he was soon thrusting unimpeded into her ass as fast and as hard as he could go.
Koneko was unable to keep up with this pace and soon found herself orgasming once again. Unlike last time, however, he did not stop thrusting even as her ass became as tight as a vice squeezing and massaging his dick. Instead he kept up as fast a pace as he could, going from balls deep to tip and then back to balls deep inside her over and over and over.
Koneko was unable to focus on anything but the sensation of her ass being tugged out and then stretched wide as he filled every fibre of her being with pleasure. Her orgasm stretched onward as her asshole was demolished by her boyfriend's giant cock. She drooled onto the pillow as her face was vacant and eyes empty, the only sound emerging from her open mouth being panting and the occasional grunt or moan of pleasure as he reshaped her guts into his exclusive cock holster.
Eventually, after many minutes that felt like hours to Koneko’s abused asshole, he finally began to speak up and said through grunts and groans of pleasure, “Gonna…cum…soon!”
Koneko reached behind herself and grabbed her asscheeks one final time before yelling out with her last drop of sanity, “Fill my guts with your hot cum!”
His pace increased dramatically at that until he finally thrust one more time and stopped when, as Koneko came again for the 4th time tonight, he hilted himself in her ass and began to flood her guts with his cum.
Koneko was overwhelmed by the sensation of his load flowing out of his cock and traveling through her guts. It was like someone had turned on a garden hose of cum and shoved it up her ass. Because of how tight her ass was clenching around his cock the cum flowing into her had nowhere to go but deeper and deeper into her intestines.
As he finally began to stop pumping cum up her ass, the two of them began to relax. They were covered in sweat, they were both tired but it had been oh so worth it. He leaned over the small body of his lover and began to gently kiss the back of her neck.
Koneko cooed at the sensation and relaxed into his gentle kissing as all the stress of worries about having sex with her boyfriend finally escaped her body. She could finally take him full and enjoy it.
Soon, he began to slowly try and extract himself from her stretched asshole. His cock, now covered in cum as well as lube, slowly began to pull out until only his head was up Koneko's ass. As he tried to pull his head out, he realised something, “Koneko, I think the head of my dick is stuck in your ass. I think we have to keep going until I’m spent.”
Koneko slowly looked over her shoulders before spanking her own ass and wiggling her hips at him. She could see the arousal all over his face and feel his semi-flacid cock once again begin to grow inside of her. As she felt this, she gave him a smug smile before saying to him, “I said I wanted you to fill my ass with cum. We’re not stopping until your balls are empty.”
A smile grew on his face as he stared down at his girlfriend. He leaned over to kiss her on the mouth before returning a smug smile of his own and saying, “Challenge accepted, lets see who runs out of energy first.”
2 hours later, Koneko lay on the bed with her spank mark covered ass raised into the air and a vacant expression on her face. Cum leaked from her ass in a constant trail that occasionally shot out as she twitched and groaned. Her boyfriend had left the room for a second to clean up as she lay vacant on the bed. She had been completely out fucked by him.
He returned with a buttplug that was three fingers wide in his hand and said to her, “Well, at least I know how you were training your ass.”
As he stepped closer, however, she quickly reached out to grab the buttplug from his hands and, before he could react, she shoved it up her ass so only the jewel on the base of the plug was visible.
Happy to see Koneko’s sanity had mostly returned, he got in bed with her and brought her into a cuddle as the two quickly began to fall asleep.
The next morning, Koneko shuffled around as she sat down at the table and glared at her boyfriend as he sat there awkwardly. She stared at him for a few more seconds before she said, “I can’t sit down properly now with how hard you fucked my ass. What have you got to say for yourself?”
He met her eyes before he said to her, “I’m sorry, Koneko. I should’ve fucked you harder until you were unable to stand, let alone sit down.”
Konenko nodded her head in agreement before another moment of silence fell between the two. Suddenly, both of them began to laugh at the stupid joke. As they calmed down from the laughter, he stared at Koneko before saying, “I’m glad you were able to enjoy it though, now we have a lot of things we need to try in the bedroom.”
Koneko nodded once again before standing up and walking to the kitchen counter as she said, “You’re right, I want to find a vibrating buttplug I can give you the remote for when we go to school first of all.”
Her boyfriend was left sputtering after she said that, which caused a smug smile to grow on her face. She stared at the counter for a second before she nodded and bent herself over it while she lined herself up so that her ass was pointed towards her boyfriend. He gasped in shock when he saw that “Anal Only” had been written on her ass cheeks. She giggled at his reaction before she spanked her own ass and told him, “C’mon, my ass needs to be fucked again. You’ve gotten me addicted to this, you know?”
Soon the sounds of flesh clapping against flesh and moans of pleasure would fill the apartment air. And thus began Koneko’s journey of anal pleasure as she found new and exciting ways to fuck and stretch her ass. But, for now and forever, her boyfriend's cock was the best thing she ever put up her ass.