“ Maaaaaster~! I’m heeeere! AND I’ve brought-”

     Astolfo had been so endlessly excited about today. It was a day of new, fun, exciting prospects! In this case, for the first time that his memory could conjure up from its data banks, Master had actually given him a duty! Sure, Astolfo wasn’t exactly the most dependable servant in all of Chaldea, but he’d always wanted a chance to prove himself since master had conjured him up… Especially because he found said master absurdly cute! But he’d spent most of his time dawdling around the base, only occasionally getting to go out on the most basic of resource runs.

     This was a summons, though. A personal summons! Out of all the servants in the building, Astolfo was the one Master wanted to see! As such, he’d busted through the door with style and panache, completely expecting to get to go on a secret mission or to comfort a lonely wizard (preferably with his body!) Instead, what he got was a room that was completely empty except for Jack the Ripper.

     Jack was a quite-a-bit-more-used servant than himself… Rather naturally, as the differences between their power level was rather dramatic. The little assassin was just sitting rather obediently on the bed at the moment, a piece of paper in her hand. The moment she noticed Astolfo she began to beam, “Mommy!”
     “E..Er.. H-Hey, Jack.” He didn’t bother to correct the “mommy” comment. Jack called everyone she seemed to meet that. He began to ask where Master could have been, but before he even could, she proceeded to hand him that paper. He tilted his head as he unfolded and began to read it. Upon closer inspection it seemed to be a letter.. A letter with Master’s signature on it!

     “ Dear Astolfo,

          An emergency singularity has ocurred. Normally Helena and Atalanta watch Jack at this time of day but I need to take her with me, and Emiya is coming too. I need you to look out for Jack until I come back. Don’t let her out of your sight or she’ll cause trouble!

     -Master”

     “No way… Babysitting..?” Astolfo whined. He had so many thoughts about how this day would be going, but this had done a rather effective job of quashing them all. No dirty times after all! Plus… He wasn’t exactly sure how to babysit in the first place. Astolfo had done a lot of things in his life, and pretty much had the adventuring and thrill seeking aspects down. How was he supposed to know how to watch a kid in contrast? Let alone a kid that just so happened to be the embodiment of a historical slasher-killer. As he pondered exactly what a kid like that might like, he was suddenly interrupted as the skirt-like lower half of his tunic was tilted up slightly. He immediately jumped and yelped!

     “H-Hey! What the heck, Jack?!” Astolfo whined. His cheeks were pink. Astolfo was no stranger to lewdity… But Jack wasn’t his type. Jack, meanwhile, didn’t seem to exactly have the same idea of what she had just been doing that he did.

     “You’re pretty, Mommy. You’re supposed to watch me, so can I go inside you?” She asked curiously.

     “I-Inside me?! You mean like…?” He made stabbing motions with his hands.

     “Huh? No. I mean… Crawl back inside you! It’s a game I’ve always wanted to play.” She said innocently, killer or no, putting a single finger to her lip and smiling vacantly.

     “ Go back inside..? Jack, you can’t do that.” He huffed softly, “I’m not a girl. And even if I was, once you come out, you can’t exactly fit back in you know.” At the mere idea of that, Astolfo couldn’t help but laugh a little. Such a dismissive attitude, however, was nothing too pleasing for Jack, who pulled a rather huffy face. Who did this person think they were fooling! It was clear they were a mommy! The pretty, soft looking hair… The cute face… That flat midsection. She was momentarily distracted for a moment… That midsection. That was what she wanted. What she needed! The thought of swelling out one of those… The thought of filling it up and being reborn for real, rather than the true strange circumstances of things. And if he wasn’t going to cooperate… Well.. Then she w

     “ Fine. We’ll play something else… There’s a ball behind master’s bed. Can you reach over and get it? We’ll play catch!” She said with a disarming cheeriness. Astolfo was… Rather impressed. From the few times he had interacted with Jack, she was rather willful about things. Maybe he actually got through to her for once? He swelled with a little bit of pride. At least that was something he could back about to master once he got back! He tamed the insane obsession with rebirth that his favorite assassin had! All it took was just a little bit of explanation.

     “ Sure, Jack! I’ll grab it for you. That sounds a lot more fun… And you can put in a good word for me with Master after all this is over, too! Hehehe… He’s going to take me on the next trip into a singularity for sure~” He hopped onto the bed, scooting across it… Not really paying attention to the way his butt was waggling in the air.. Or taking notice of Jack scooting up behind him either, for that matter….

     ‘ Jack, I don’t really see anything back here. Maybe it slipped under..Ah?!”

     The feeling of his underwear being yanked down was sort of unmistakable. However well-thought-out Jack’s deception might have been it would have ultimately been pretty easy to usher Astolfo one way or the other. He wasn’t exactly the brightest person in the world as a servant, after all! That, however, was a little bit of a step too far even for him. He immediately began to flail and kick, but bent over like this he didn’t exactly have a whole lot of hope of escaping. Jack’s eyes, meanwhile, lit up with utter delight. The lacy undergarment Astolfo had been wearing wasn’t the only feminine thing about him down here. His behind was positively -plush-! She put both of her hands on either cheek, sinking fingertips into the pliant flesh. Hot, firm-yet-yielding… Everything one might have wanted in an ass. This was definitely the ass of a true mother!

     “ A-Agh! Jack! Jack, stop grabbing at that! That’s not for that! That’s-” Astolfo stammered, sweat pouring down his face. How in the hell did he get in this situation?! All that assurance to the assassin that he most certainly wasn’t to be considered a mommy, and yet here she was undressing him plainly. Images of master walking in in the middle of this were immediately flashing through his mind, and he couldn’t honestly decide whether to blush at them or feel ashamed. Probably somewhere in between would be the most sensible, he assumed, but what happened next gave him a little bit more pause.

     “ What do I press to get inside..?” Jack inquired, cutting him off. Before Astolfo could further explain that she had entirely the wrong idea, she gave his ass a solid slap on one cheek; hard enough to leave a hand print on the little paladin’s pristine skin! He yelped out loud, his back arching. Okay, there was the shame. Sure, he didn’t mind getting treated like this all that much mainly out of the fact that it felt good, but a misguided little servant girl doing it made it all the more humiliating.

     “ Geeze! There’s not a button! What you’re trying to do is impossible anyway! There’s no way you’d be able to get in an opening like that at your size without a lot of...Heeeeh?!” His eyes widened massively, jaw dropping as both of Jack’s hands dug into the crease of his plush butt, clenching down on the cheeks and spreading them apart from each other. The sensation of her little fingers stroking at that hole back there, which he figured -had- to be completely exposed at this point, took the words right out of them. For Jack’s part, she was more fascinated than anything. She leaned inwards curiously.

     Astolfo was correct; she was staring at that little pink pucker normally hidden away from plain sight with abject fascination. This was it! This was the hole! It was precisely what she had been looking for!

     “Mommy, I found it!” She said, lips slowly curling into a grin. Astolfo began to formulate a response, but whatever qualms he might have had died quite thoroughly in his throat as Two of Jack’s fingers prodded their way into his asshole. Instead he let out a noise somewhat comparable to a cat with laryngitis, “But it’s so tight… You’re right. I don’t really see how I’m supposed to cram myself back inside of this..”

     “A..At least you’re getting it now!” Astolfo wheezed. There was a brief moment where he thought that he was in the clear, though he admitted, it was odd that he didn’t feel Jack’s hands withdraw from between his asscheeks. And then, he was utterly proven wrong as he abruptly felt an intense stretching! No, she didn’t withdraw.. She entered! Astolfo wailed with shameful pleasure and genuine shock as the pair of hands prodded into his hole, pressed together and held flat. He could feel them prodding around against the walls of the tight tunnel, pushing against nooks and crannies in a way that was making him tremble. His legs spread in either direction almost obediently, the toes of his boots digging into the carpet. He wanted to stop this, rather distantly, but as with all things, his will was overridden by his Evaporation of Sanity. It felt good, and when something felt good his body had a tendency to do whatever it felt like! In this case, it was lying there with Jack wrist-deep in his behind.

     “Wow.. It’s really tight, mommy. But It’s surprisingly stretchy~ I think if I can just… Ngh..” In went Jack’s forearms with a push, Astolfo eyes rolling back in his head as he coughed and sputtered. His hips bucked, grinding against the bed, the bare bulge that Jack had unearthed in his front grinding against the sheets of master’s bed below him. She wasn’t tending to it.. Why would she? To Jack, this was entirely a process of getting into somewhere she wanted to go, and that odd thing dangling from the front of “mommy” was just weird extra stuff. She could feel a slight pull on her… It was almost like she was being sucked in! Not that she minded, the inside of Astolfo felt so incredibly smooth. It was clean, too! Servants didn’t exactly have any sort of unpleasant problems that could arise in a normal human attempting to do something like this thankfully.

     “J..Jack.. G..Guh.. This isn’t… Going to… Ahhhn~” Astolfo arched his back as Jack plunged even deeper. He wanted to warn her! Somehow convey to even her what was going on! But a loopy, loony servant like himself would have had a hard time convincing someone like her even in the best of circumstances, and preparing for full body penetration was on the list of the worst circumstances, he would wager. His toes curled firmly, and his eyes fluttered. He could feel drool escaping his lips and pooling on the bed below him completely involuntarily, unable to stop his body’s intense reaction even as the mother-seeking assassin was buried well past her elbows, almost up to her shoulders.

     “It’s getting harder to push...” Jack mused. It wasn’t exactly easy to leverage yourself for entrance when your arms were pinned together like they were in cuffs. She could feel them bending back somewhat; going through that tunnel that would surely lead to mommy’s stomach and the paradise which she envisioned! It was a strange sensation, and though it was hardly unpleasant, it paled in comparison to what the paladin she was entering was going through. It only got worse when suddenly Jack felt herself get tugged forward, “Wow~! It’s pulling me inside! Mommy must really want me inside her too~!”

     “ W..Why is… Guh...Why..?!” Astolfo groaned. Sure, evaporation of sanity usually meant that he reacted to what felt good in gratuitous ways, but this was going too far! Before long, he could feel Jack’s face smooshed against his ass, the smaller girl’s warmth palpable. It made the hairs stand up on the back of his neck, not so much for the immediate sensation but rather the one that he knew was coming. He could feel her arms entirely buried within himself, now beginning to push outward inside of his stomach. And if she was getting sucked in like this, well… That could only mean that next was-

     Schlrp. In popped Jack’s head. She got a momentary sample of Astolfo crying out in pain and pleasure, but it was immediately muted by her ears entering into that hot tunnel. It smelled musty and it was too dark to see, but that would hardly deter the little assassin! After all, she’d come this far. She wasn’t going to let a little thing like a change in atmosphere deter her from reaching the spot she wanted to go.

     “Too big! Your head is too big! Aaaah!” Astolfo was kicking his legs in earnest, pounding against the floor below him. Unable to hold back a full range of movement he started to writhe about… But Jack dangling from him, perpetually sinking deeper, sort of limited the way that he could move. In the end it looked less like the desperate combative throes of someone who was being pushed well past the brink and a lot more like a fish flopping helplessly on the deck of a boat, “J..Jack… There’s no way you’re going to fit in there. Pull out!”

     His girly voice, hissed through his teeth or not, didn’t exactly make for a convincing tone to command people in, even if Jack could hear it! Unfortunately for him she was far beyond that point, buried in that ass that seemed intent on sucking h er deeper… And similarly unfortunately for him, his body seemed to have a different idea of what it could and couldn’t handle as it only continued to aggressively pull her deeper and deeper inside of it, Her flat chest made its smooth interest as pleasure continued to bubble through Astolfo with seemingly ceaseless intensity. That section of her body was dramatically broader than anything that had entered so far; it felt like he was being fucked by an absurdly-sized cock. As such it was little surprise that mere moments after that section had forced its way in he came; hard. With a wail of despair, he violently thrust downwards against the bed of the person he’d hoped he’d simply get to do dirty things with today, a splattering gout of cum bursting out from him.. And then another, utterly soaking the area below him as he sputtered and managed to vocalize an, “O-Oh… Oh noooo...”

     The walls that were guiding Jack inward clenched even tighter; she hadn’t been sure that was possible, they felt skintight already! Somehow, though, it managed to as she was urged deeper, the hot narrow tunnel winding her inwards to the eventual conclusion she knew that she had to reach at some point. So many thoughts were going through Astolfo’s mind as he felt her elbows start to crest into his stomach while her thick torso continued to pummel his senses… But they were all a buzz of nonsense. What would any of it have mattered, though? Could one really put things more succinctly than “the stomach and a womb are two completely different things?” Jack had proved she had the capacity to dog her way in there (thankfully in a much different manner than she typically dug into stomachs), and what’s more, his body proved itself more than capable of allowing her passage. She was gut-bound, and he could only imagine what would even happen next after that point!

     Jack’s lower half was nothing to sneeze at’ She had quite a butt, and an ample pair of thighs; cruelly, it almost seemed like a parody of what a good prospective mother might have had. As her pelvis disappeared, those began to enter him, and at last, the assassin servant’s head pushed into his stomach. Immediately crammed against the belly wall, Jack’s eyes were aspark with absolute glee and fascination from the very moment her head had nudged aside the fleshy ring serving as a barrier between the tunnel of his colon and the stomach itself.

     “Mommy, I’m in your stomach~!” She half-fawned, clasping her hands together excitedly. Astolfo, meanwhile, groaned in response. The sensation of her gut protruding outwards in his stomach was alien to say the least. The addition, all by itself, had made it so that the bottom of his tight black top was riding up above the shape her head was making, and as she continued to pile inside of him, it only accumulated more thoroughly. Astolfo was normally proud of his physique; after all, he kept himself very fit, feminine or not; he was so pretty that being in possession of some cut abs was hardly a deal breaker, or even a dead giveaway of his actual gender! Jack’s introduction was ruining all that, spilling out with her shape flabbily, vivid bumps and bulges rippling all across the over-tight surface. He let out a little sound of despair at this more than her sealing herself in a way in a spot that would surely result in her digestion; she was probably going to leave stretchmarks on him no matter what he did! Stretchmarks on his spirit origin! He’d have to explain it to every single master he was ever summoned to from this point on! What a miserable fate.

     Her legs kicked and fishtailed outside of him. There was no fighting it now.. For Astolfo, anyway. He would have figured that it would have been a little bit more natural for the prey to be the one fighting this process, but no, the willingness of the participants seemed to have been switched entirely on their head. Maybe that was fitting for such a pair of screwed-up weirdo servants, but still, it wasn’t something he was going to be happy about! Her ankles were all that was left outside of his ass at this point, Jack’s toes curling and scrunching with delight just has own had been earlier, shamefully. The good news was that the pleasurable feelings that were being conjured by this whole process were slowly starting to fade at this point… But the bad news was that things were well past the point of no return at this point. He was fairly sure that Jack wouldn’t have been able to make her way back out of him even if she wanted to at this point, and as her feet finally disappeared with a lewd fleshy pop, that fear was both realized and confirmed.

     He weakly attempted to push himself off of the bed, but his strength was utterly failing him as the sensation of the last of the assassin made her way slithering up the wrong pipe. The last bits of her being added to his stomach were almost imperceptible; his stomach was so large beneath him at that point, he was half-teetering on it. Even without the debilitating and strange sensations of the wriggling shape inside of him, he was having to deal with the weight of an entire person located within a spot no person was ever meant to be stuffed! Not without dire consequences for all parties involved, anyway.

     “J..Jack.. O-Oh god… I’m so… Full.” He whimpered, his weight finally tilting onto his side and allowing him flop to something approximating stillness on his side. Inside of him, Jack was shifting and squirming, her heart all aflutter as she looked at the slimy, dimly-lit walls around him. Their pink and slimy texture might have been repulsive to just about anyone else imaginable, but for all intents and purposes she was currently under the impression that she had fulfilled some sort of long-desired dream by crawling inside of Astolfo at this point. Exploitative, she mashed and pushed her palms against the mess around her curiously; was this really what the inside of a mommy was supposed to be like? It was… A lot less bloody than she had anticipated it being. Ah, well… No reason to question it! She was here! Finally here! Why bother with such ponderous thoughts that don’t amount to anything?

     “G..Gotta.. Push her back out.. She’s gonna ruin my figure..!” Astolfo groaned. He was resistant to the end, but even as he said it he was unsure of exactly how effective anything that he could do at this point would be. He didn’t even know his servant body would capable of swallowing people, much less with his ass! How exactly was he supposed to get them out if they didn’t even come in? Holding his throat, he wedged his knees upwards against the bottom of his stomach and did the only thing he could think of; he began to cough and gag, trying to spit her up. Unfortunately, a solid twenty or thirty seconds of this seemed to be providing no results worth mentioning beyond the sound of a giggle from the inside of his stomach; the motions weren’t causing her to spit anyone up, but they were making his gut squelch and shift in a way that amused Jack! He rolled his eyes, sweaty and exhausted from the whole process, whimpering, “I..I’m so glad you find this so funny! D-Damnit...”

     Her knees and feet pressed outwards, stretching. She was getting comfortable. As far as she was concerned, she was home. It was a hard-fought victory, and it had ended with her needing to prove her point in the most extreme of ways, but she had won. As she settled, the stomach clenched and gurgled around her. She had no thoughts or ideas of this being dangerous in any way, and she was quite deaf to the pleadings of the poor femboy that currently held her within himself. She’d not struggle as his stomach did what, well.. Stomachs did!

     “No..No! Agh… M-Maybe I can get her out the other way!” Astolfo rationalized in his mind! Though, Master’s bedroom was hardly a place to do that. He had to get out.. Get moving somehow. He hefted himself off the bed, massive stomach swaying and groaning as he did so. His mind was moving a mile a minute, “ Gotta get to a bathroom.. Gotta get to a bathroom and push!”

     He stumbled his way outside, moving so fast that he almost lost his footing and smacked his head squarely into the wall directly outside of the wall with a puppy-like yelp. His stomach had hit it before his face did, squishing and squelching, the sound of noisy gurgling filling the air… It was getting louder and louder, reminding him that he was working with a time limit! But one that would be manageable so long as-

     “….Oh my.”

     The voice felt like a frozen nail had driven through his spine. Astolfo winced… And slowly turned himself around in the hallway, the most innocent grin on his face that he could possibly muster as even more sweat began to trickle down from below his shaggy pink bangs. Standing just behind him was a familiar servant who he was quite sure he didn’t want to run into right now; a small girl in a traditional Japanese kimono. She was lovely (maybe more so if you weren’t acquainted with her very well), turquoise hair spinning down her back with two oddly shaped dragon horns on either side of her head. The golden-yellow eyes locked on him were dancing with a dangerous light, the girl tapping a shut folding fan down on one palm.

     “...It seems you’re quite swollen, Astolfo-chan. With child, I assume.”

     “A-Ah! Kiyohime! I, um… Er…! I’m a boy, so, this is just-”

     “...And emerging from master’s room. Have you two been..?” The dragon girl asked in a very quiet voice that was somehow thousands of times more frightening than any sort of angry bark could have ever been. Astolfo’s lips quivered; Kiyohime was maybe the only servant that was even less reasonable than Jack. And with a deadly obsession with master, such trifling things as “gender” hardly meant anything to the berserker any more than the assassin did! Before he could utter out any sort of failed elaboration to his explanation, she unfolded her fan, positioning it in front of her mouth. Blue flames began to dance above them, embers simmering as the very air around her seemed to begin to spark and catch fire. Her still-visible eyes darkened into an expression of pure hated, “...Unacceptable. I am the only one permitted to carry Master’s child. I’ll burn that mistake right out of you. Along with you. ”

     “Oh crap.” Astolfo managed to say before the fleeing began. Panicked, wobbling, rolly-polly running at high speeds. Behind him, various fiery explosions were combusting all through the hallway, putting craters in walls and setting off the sprinkler system as Kiyohime lobbed dragon fire at him. Thankfully, she wasn’t all that much faster than him! Hurriedly charging through the maze like layout of Chaldea, he whipped himself into the first open door he found, hurriedly slamming it behind him. He rested against it, panting and gasping… Was his stomach.. A little smaller than before?

     The bulge inside was getting a little bit smaller. That probably wasn’t good, was it? But there was still a chance! He took a deep breath, “I just have to get to the bathroom.. G-Guh… It hurts… It’s so heavy.” He whimpered, clutching his gut in armored palms, knees shaking a little. Good thing he found this spot regardless. Anything was better than Kiyohime! Actually.. Now that he thought about it…What room was he in?

     Hands gently laced around him, the massive-horned head of Kiara Sessyoin looming over his shoulder with perhaps the most horrifying expression of pure lust that he had ever seen in his life, a small amount of drool trickling down from her lips which she quickly lapped up with a tongue motion that reminded Astolfo of a frog: “Cramps? I suppose it’s to be expected… Though I have to admit my surprise that you’re kinky enough to be into male pregnancy, dear. Let me show you a technique from the Kamasutra meant to ward off that pesky pain...”

     The pink-haired boy’s scream could be heard for quite a distance.

     Dejected and whimpering, Astolfo stumbled into his quarters… Weakly making his way to the bathroom with a slumped stance. His stomach was sagging… Half of the size that it had been an hour or so now. There was little question as to the fate of its occupant. Jack had digested peacefully, probably asleep and blissfully thinking of rebirth, knowing her. At least that made one member of the two-part equation happy. Fat ha d made its rounds onto more places than the current hefty gut he was sporting; his thigh had grown immensely, the thick set of them that Jack had been sporting seemingly gifted to him to the point that they were bursting out of his black stockings which were now riddled with pockmarks where flesh was bulging out. His panties, long forgotten in master’s room, would have also been full to bursting with the newly fattened asscheeks he was sporting that were thick enough to gently-but-noticeably jiggle with each step he took… And the worst part of all of this? He could tell his body still wasn’t quite through! There was more of Jack that would be added to him… Hopefully stuff that could be worked off with time, but for now, this was such an impactful development that he knew whenever he was summoned he was going to be sporting hips that had a problem fitting through most door frames to show for his trouble.

     One part of the process, though, was very much at his end. His original mission had been to push Jack out before she made the inevitable trip through his digestive tract, but even with that mission being a resounding failure the trip here was inevitable. He navigated his plumpened ass to the toilet seat, surprised at how much higher up he was currently at than typical while sitting. Servants didn’t need to eat, normally.. But they certainly could if they wanted, and in the end, food ended up being food once it was all used up. He sighed, and began to push, both hands on his knees as the assassin turned bowel movement began to fill the space below him.

     His stomach had done a real number on Jack… That, or maybe even if she hadn’t been expected it, her body had yielded to digestion far more cooperatively than most would expect. Smooth log after log emerged from the boy’s asshole, once again stretching it to the limit; it felt a lot more manageable this time though, and actually rather pleasant as there didn’t seem to be any bones in any of the fetid turds that were piling up beneath him. They’d been ground down as effectively as any other sort of food he could have eaten. Just smooth shit… That was all the poor girl amounted to.

     “This.. Ngh.. This isn’t the ‘birth’ I think you were hoping to get to try out, Jack, but… I did try to warn you.” He said with no small degree of sympathy. He didn’t really have anything against Jack! And he certainly didn’t want to live the aftermath of his absurd figure which she had given her! All things considered, this had been unwilling… But at least the ending was pleasant. After finishing, he hefted himself up and looked back at what he’d done: the mess inside of the toilet was unrecognizable as a person, let alone a powerful servant. He carefully wiped himself clean, tossing the paper below him and flushing. No sense in keeping the evidence around.