The Holy Sippy Cup War Ch. 4: An Odd Match (Patreon)

“But how can you trust such information when the source is suspect?” Sakura Matou asked, looking at her servant so casually seated with his diaper fully on display. Astolfo wasn’t even trying to hide the yellow stain growing on his nappy that bulged out under his battle skirt, if he’d even noticed it at all.

“Why would Assassin lie?” he asked with a laugh, looking to his master, “We all have something to gain by the Matron being taken down so why shouldn’t it be us? Besides your amazing servant took it upon himself to go out and collect this information!”

Sakura shook her head in response, unamused by her servant’s lack of sense in such a situation. If Assassin knew where the Matron resided, why not make a move on her himself? It made no sense to allow another to take over the leading role. In the week since she’d summoned her servant, the Rider Astolfo, Sakura had come to expect this attitude.

He was loud, boisterous, and didn’t plan his actions well, if at all. It was a complete contradiction to her way of doing things. He wanted to jump right into the action, to fight against the other servants to come out on top. Even behind Sakura’s back he was apparently having conversations with other servants, maybe even some masters.

It was beginning to erode her patience, and privately Sakura wondered how she might bring her willful servant to heel without using one of her precious command seals. “We don’t know anything about the Matron.” she said, her face becoming stern as she approached Astolfo, “What’s their primary class? Who’s their master? What powers do they possess? Without knowing any of this I will not make a move.”

Astolfo piped up, seemingly oblivious of the growing irritation exuding from his approaching master. “Oh, oh,” he said, practically bouncing in his seat, “I know some of this! She’s a caster for sure–that’s what Assassin said–and they took over an old mansion on the edge of Fuyuki, and the Matron’s powers are—”

Sakura stopped her servant’s seemingly nonstop flood of information with a finger pressed to his lips; she was nearing the end of her patience quickly. “If any of this information comes from Assassin, it’s not usable. What could you even do against such a powerful enemy?” she asked.

In a sudden burst of movement Astolfo jumped up from his seat, causing Sakura to jump back. His skirt fluttered as he bounced up, showing off even more of his padding.

The skirt itself connected to an almost skin tight black bodysuit, giving it the appearance of a very short dress on the servant. Over his shoulders rested a furry collar connected to a short half-cape, one that barely made it halfway down his back. Covering the servant’s slender legs were long black stockings secured by garters that disappeared underneath his skirt.

The “Cryer” portion of his outfit was the obvious diaper underneath the garters. Due to the shortness of his skirt and the thickness of his padding Astolfo’s nappy was always visible, even when dry. It never stayed clean long though. It seemed that every fifteen minutes he was wetting himself, soaking his diaper without even realizing it.

Sakura hadn’t had any problem changing him, not at first anyway. Only when it quickly became a constant process, did she grow sick and tired of it. It was made clear that only after several wettings or a mess would she bother and she could usually tell by his waddle if it was required.

Astolfo, now standing proudly, looked around the room, making sure he had ample space for what he was about to do. “I am a servant of the rider class,” he proclaimed, “It’s time you saw my steed.”

With a flourish the servant jumped, calling out as he flew through the air. “Show us your true power Hippogriff!” he called. Underneath him, golden energy shone brightly, forming the shape of a creature with wide wings and four legs. It almost took up the entirety of the room with its size causing Sakura to back up against the wall.

She was impressed for a moment. However, as the blinding light of magic dissipated around the Noble Phantasm some things struck her as odd. The form of the creature was strangely stiff, its eyes had an eerily glassy appearance, and its feet were connected by two crescent shapes.

Astolfo sat proudly on a large Hippogriff-shaped rocking horse, looking expectantly at Sakura. “Ta-da! The Otherworldly Phantom Horse, Hippogriff!” he declared, “What do you think?” he asked.

The purple-haired mage was speechless, feeling completely unable to bring her disappointment into words. It almost felt mean to her. She now understood that her servant wasn’t just ignoring the absurdity of his Cryer status–he didn’t even recognize it. To him, this was an acceptable state.

She couldn’t bring herself to say anything for a moment, still stunned at the reveal of her servant’s “Noble” Phantasm. Astolfo rocked gently back and forth on the toy, waiting expectantly for a reply. From underneath his padding a slight buzzing sound could be heard.

“C-Can it even fly?” Sakura asked, struggling to find the positives of this situation.

“Of course! With me in the saddle it’s the finest mount for the greatest rider,” Astolfo said, bringing the rocking beast up the slightest bit to prove its upward mobility. His head came close to touching the ceiling of the large room and underneath him, the buzzing grew louder.

Sakura caught his face going flush as he rose in the air and he rocked back and forth rhythmically as he rode the massive toy. Something about his actions felt off as he flew and Sakura came out and asked plainly; “What’s wrong?”

Astolfo brought the beast back to the floor, sliding his soggy diaper off the saddle to reveal that the saddle itself had a protruding rubber nub that would have pressed into Astolfo’s diaper and against his sensitive lowers. It still pulsed ever so slightly as the rocking beast slowed down and sat dormant.

He looked at Sakura with a wide smile. His expression portrayed no embarrassment that you would expect from someone who just got caught riding a vibrating “toy”

“The higher I take Hippogriff the faster those vibrate.” he explained, “The feeling of it going through my diaper is absolutely euphoric, do you want to try master?

Sakura shook her head in complete disbelief.

“No…” Sakura said quietly, eliciting a shrug from Astolfo.

“Suit yourself,” he said, “I promise it’s the best though!”

A growing embarrassment for Astolfo caused Sakura to frown as the apparition of the mythical creature disappeared. His situation was almost pitiable in a way. It wasn’t just that he didn’t care about his condition, it was just a normal fact to him.

Sakura pushed her head into her hand, shaking it while she rubbed her temples in exasperation. “It’s got to be something to do with the Cryer class.” she thought, working to parse the situation in her head while her servant looked at her expectantly.

“So, what do you think?” Astolfo asked, “Impressive right?” The anticipation in his eyes as he awaited his master’s praise of his “impressive” mount caused Sakura’s thoughts to falter. She felt at a complete loss for words but didn’t want to disappoint him. “He really thinks he’ll be able to face another servant like this, especially one he claims doesn’t have the same handicap.”

Astolfo’s hopeful look didn’t go away and several seconds of silence left an uncomfortable feeling between the mage and her servant. “I-It’s impressive…” she said, trailing off because she didn't have the heart to tell him otherwise.

“Isn’t it?” Astolfo said, stepping away, “Now let’s go! Hippogriff can take us right to her mansion and we’ll take that matron title. I still have plenty of amazing abilities I haven’t shown you yet. If we get that Matron title it’ll give you a leg up in the war. Plus, bonus, it’ll keep a lot of people from getting caught in the crossfire.”

Sakura cringed, reaching out to stop the servant as he began waddling away. “I still don’t think that’s a good idea, Rider.” she said gently. Her hand rested on his shoulder, giving it a slight squeeze to reassure him. “Maybe it’d be better to pursue the other servants of the Cryer class first, some people on equal footing…”

Her voice was gentle, and she was doing her best to avoid sounding condescending, but her attempts to remain tender may have had the opposite effect. Astolfo’s face fell, morphing from a carefree smile to a furrowed brow and a frown.

“You don’t think I can do it!” he accused indignantly, pulling his shoulder away from Sakura’s grip. The move was far too aggressive and after Astolfo jerked away he began to tumble back. The servant somersaulted on the carpet, landing with his face pressed into the floor while his knees pushed up his rump. It was a position that caused his skirt to fall and expose his soggy diapered bottom even more.

The mage watching the display couldn’t help but humor in the ridiculousness of the situation and stifled a small laugh at the boisterous servant’s blunder. With a piercing glare Astolfo looked up at Sakura, obviously noting the stifled laughter that tore through his bravado.

His cheeks burned red with embarrassment, a reaction that surprised Sakura. Not once in the short time of them knowing each other did Astolfo show any semblance of humility about his diapered state or his loud bravado. Something about his “Master” laughing at him seemed to dig at his core and reawaken that emotion within the servant.

He pushed himself up from the floor, letting out an annoyed sigh as he did. Upon standing he stared at Sakura, creating a silent stalemate between the two of them. Astolfo hadn’t bothered to fix his hiked skirt, completely showing off the yellow stained diaper around his waist to his master.

Sakura’s eyes locked in on the padding, noting that it sagged a little lower now. “He’s wet again,” she thought, “sometime in the last couple of minutes. He really is like a baby. I’ve got to help him with everything...” He hadn’t announced or reacted to it himself, which meant only one thing: he likely didn’t even realize he’d gone with all the excitement around him.

“Well, I’m going anyway!” Astolfo declared, spinning on his heel, “I’ve got the element of surprise after all..”

Sakura’s thought process was interrupted yet again by the sudden snap of blustering foolishness from her Servant, bringing her attention back to him. She glared at the back of Astolfo’s head, her voice pitched lower as she asked: “I’m sorry, what was that?”

The Servant looked back at her with a cocky smile, one that was quickly dashed away when he saw his master’s intense look. “I-I said try and stop me, I’ll go do it myself!” he said, the signature arrogance faltering just a little bit.

Astolfo moved to make another waddling step away from his master but was stopped in his tracks by something gripping his ankle. Looking back he saw it was a dark tendril that snaked out from a shadow on the floor–Sakura’s shadow.

Astolfo tugged again only to feel the shadow tug back stronger and pull him down to the floor. He hit the carpet once again, letting out a groan as his body thudded against the floor. He struggled to free himself from the restricting magic pulling him towards his master.

He reached down for his book, Casseur de Logistille. He could break the magic holding him down if he could just pull it off his belt. *Pop* He managed to undue the snap on the leather holding the book down. The magic pulled him closer to the threatening figure of his master. Astolfo fumbled, wrapping his fingers around Casseur de Logistille clumsily before pulling it up infront of his face,

“Just… have to... open it!” he grunted, struggling against the rough friction of the floor. He worked a finger in between two pages but before he could flip open the tome another shadow tendril whipped around his wrist, yanking it hard. The tome itself clattered to the floor, left behind as he was pulled away from it.

Behind him, the shadows split and extended, creeping up from the floor to wrap around his other limbs. Astolfo found himself hoisted up in front of Sakura and bound in place by the shadowy restraints, pushing his legs together and keeping his hands held behind his back.

                                                                                                                                                     Art by Pissibilities

He looked at her with a smile while closing his eyes in apology. If he had a hand free he likely would have rubbed the back of his head to complete the picture. “Well I guess you can stop me,” he said, feigning innocence after his act of rebellion.

Sakura wasn’t having any of it. Her head was tilted downward and Astolfo couldn’t see her eyes but he could feel the intensity of her annoyance.

“I get it now,” she said quietly.

Astolfo cocked his head. “Get what, Master?” he asked nervously.

“You don’t know any better,” she responded, taking a step away from her mischievous servant, “You need me to punish you so you can learn…” She continued to move toward the exit of the room, the shadowy tendrils following her as she went.

“Where... are you going?” Astolfo asked, his eyes going wide with worry.

“To find a riding crop,” Sakura called back.

Immediately the Servant’s bound hands moved to cover his diapered back end, fearing that she might be serious.

The fantastic image for this story was done by Pissibilities who does some wonderful watersports based art and who did a wonderful companion piece to this story. They were cool enough to let me include it here and if you want to check out their work you can head over to their Deviantart: https://www.deviantart.com/smutmoresmut or their twitter: https://twitter.com/SmutMore