Of Babysitters and Caretakers - Ripping Innocence 1 (Patreon)

Of Babysitters and Caretakers - or ‘When Promiscuous Lolis want some Meat' (Loli/Mesugaki Stories)

Episode ‘Grand Order Extravaganza: Ripping Innocence 1 (Jack)’

Summer!

In the past, Ritsuka Fujimaru (known to many as Gudao) loved the season as it was a good way to deepen bonds with people he cared and loved for. When he joined Chaldea, that habit persisted for… two years. Then it became impossible for him to be that excited by the prospect of experiencing it.

Female Servants tended to be quite attached to him compared to male ones. At first, he thought that wouldn’t have led to any issues as he planned to split the time spent with the women together with his ‘Servant Bros’. It was only fair for him to get to have fun the manly way too… but he never considered the women wanted that sort of ‘fun’ to be lewd to the full extent.

Many workers at Chaldea had started rumors that the women were promiscuous with those in the Singularities set in holidays but… the truth was that the only target of their sexual advances was none other than Gudao.

Da Vinci-chan was a lifesaver with her special concoction that prevented him from either breaking too fast or draining even faster, but… in the end, some Servants were just built differently.

The times he had to call for a break for his poor pelvis were concerning and it didn’t stop being an issue in his second year in Chaldea. It was around the time the Goetia issue got solved and more Servants were joining in- a lot of which were women. More women, more depraved efforts to scratch their itches… Gudao was losing control.

Third year came while they were facing the Lost Belts, and Gudao was worried about Barghest getting a bit worked up on ‘establishing a claim on him for the holiday’. Considering how she usually established a ‘claim’ and how he personally felt that, Gudao was… well, of weak mind and body.

Likewise, the presence of the competitive Morgan trying to outwit her ‘many sisters’, Melusine and Baobhan Sith being horny on the regular due to how repressed they were at times…

He needed a break, and his salvation came from the one that became his first time and also his closest lover. If someone ever said that Mash was too much ‘vanilla’ with her ideas of relationship compared to the rest, they would be utter bastards. Mash was the best woman he ever had as a friend, confidant and bed-fellow.

She understood her Master’s limitations and sex with her was still his favorite activity due to how well-planned and well-paced the sessions were. But the one thing that made her an angel was the plan he set him up to enjoy-

Spending a full month away from the other Servants in a special ‘controlled’ Singularity set in a small beach that was furbished to last a full year of relaxation. To Gudao, this was heaven in disguise of a ‘solo mission’.

Thus, as a Solo mission, he needed someone with him.

Mash refused to go along with him on two principles: 1) it would be suspicious that she came with him and no one else, with many women perhaps seeing this as a trick of sorts; 2) she had to be around to monitor the situation and keep things under control while he was out of sight.

But that’s where the issue came: who to bring with him? With Mash excluded and most of the women out of the list, the rest was… limited. Most Male Servants were lovable in their own way, but they were also the kind of people that had the kind of strong personality which made them unbearable to enjoy for a month straight.

Gudao was a bro, but even the broest of bros needed a break from their own bros.

With the Guys removed too… it was a matter of the ‘genuinely small Servants of the female kind’. Wu Zetian was excluded as an adult, Jeanne Alter Santa Lily was too social of a person to spend a month with a single one, Master or not, and Nursery Rhyme needed her good dose of social interaction due to how isolated she tended to be most of the year.

Shuten Douji? Excluded for the same reason as a Certain Chinese Empress was excluded. Ibaraki? The lovable Banana-Oni was too much of a careless action junkie that tended to start trouble for fun. Paul Bunyan? She was too much of a giant on most occasions. Abby? He… could not deal with her alone for a month. Many things can just go wrong with that.

As he pruned out more names from that list, one managed to stand out the most from the rest.

Jack the Ripper.

Jackie was one of the first ‘loli Servant’ he acquired back in the London Singularity. She was a bit distrusting of others, but had grown a lot with her capacity to care and be close to individuals that were not her ‘Mother’. She was surprisingly mellow around Gudao despite how brutal and vicious she was in combat, and she tended to behave the most childlike compared to the rest.

So, with that in mind, Gudao decided to have her join him on this solo holiday. Jack was ecstatic at the idea and gave him a big tight hug.

“A whole month with Mommy? We are so happy~!”

With that plan properly unfolding, Gudao prepared his luggage and helped Jack with hers and… soon it was time for them to leave. Mash gave her Master a special communicator device they could use to speak with each other to give some warnings or reports in regard to how things were going.

Stuff could still go wrong, so it was only fair that they kept communications running as efficiently as possible to have everything called off in case of major problems.

With that out of the way… Gudao stepped through with Jack through the Rayshift and soon his sandals were firmly pressing against the warm sand of a small beach in a ‘desolate’ island.

Jack’s giggles as she scouted around and happily explored the safe holiday spot brought up a few curious things Mash hadn’t mentioned- like the fact that beyond the living quarters, the eating area, and a ‘shop’ with all the beach items that could be used without paying for any of those, there was also a mini-onsen.

That was going to be an interesting idea to pursue after a while, but for now they were planning to hit the beach. So, after they set down their luggages to their rooms, Gudao helped Jack put on some sunscreen before having her off to swim around a bit.

The girl giggled a bit as the young man carefully helped her by her back the most, the Assassin being more than capable of doing her front just fine but… Gudao still found a rather interesting detail he never contemplated much about.

After all, this was the first time he ever helped Jack with this chore, and he never once thought about… her butt. Her round, inviting butt that looked so oddly enticing despite who owned it.

Jack’s ass was perhaps one of the thiccest by bodily ratio. It was impressive, really, but Gudao hardly fondled it while applying the cream. He noticed the girl looking at him over her shoulder, shuddering briefly as he was putting the sunscreen on her lower rear and… that was awkward.

Once he was done with Jack, it was his turn to get the sunscreen. There were no complications there, and soon they went for a relaxing swim in the calm sea that was theirs for a full month.

Ah, it’s been so long since I enjoyed Summer like this~

Gudao was enjoying that little piece of heaven, and Jack was swimming around as excitedly as she could be. They retreated back to their resting spot roughly half an hour later, with Jack feeling a bit bored and wanting to play some beach volley.

After retrieving a volleyball the two played for a while, enough for Gudao to feel a bit… drained. It’s been a while since he played so much and sex had made his body react quite tiredly with anything that put a drain on it.

So, he was soon spent. Which was tragic considering how active he tended to be most of the time. Jack stared at her Mommy with a sad look for a while, unsure of why he was so tired but…

“Mommy, did you ask us to join you here because the other Servants annoy you with sex?”

The bold and innocent question struck him dead, shocked as he turned to Jack with wide eyes.

“W-What? Who told you that?” It was not like Gudao ignored Jack’s inner maturity at times, especially with her predicament, but it was still a big surprise that she was aware of that.

“We noticed,” Jack pointed out calmly, then smiling. “We know that Mommy is a very caring Master, so he can’t exactly say no to those other women. They can be so cruel with Mommy. Which is why Jack will help Mommy relax.”

…

“How?”

“Well, by being like Mash is to you, Mommy! After all, you love her a lot!”

…That was concerning.

“Jack, I don’t think that’s- Hmph~!”

Jack was no master kisser, but she was a determined one as she just jumped at the occasion to steal his lips and, cutely so, try to dominate him with it. Sadly for the little Assassin, Gudao was far too deep in the mastery of the smooching arts, and effortlessly turned the table by instinct. His brain had shut down for a moment, and his basic muscle memory kicked in.

By the time he realized what he had done, Jack was pulling away with a red but pleased face and a blinding smile plastered on it.

“T-That was so good, Mommy~. Kissing like lovers with you is so tasty!”

“J-Jack, this is not an idea and-”

Gudao panicked as he saw her shift to rest her head on his chest and her lower body near to his own. He thought this was a mistake, and he was about to push her off… until he realized that Jack stopped there, nuzzling and almost purring as she hugged him dearly.

“...What is this?”

“Cuddling~, Mash told me that cuddles are nice and, since sex is not a thing meant to happen until a bit later, those are the best to be close to Mommy.”

Oh! That’s… that’s actually nice to know. Ignoring the fact she had planned to have sex with him later that day. Gudao still wasn’t sure of a couple of things however.

“J-Jack, does Mash know of this?”

“Oh yeah,” The chirpy assassin replied. “Mash-mama said that we should treat you as if we were her.”

…Gudao realized what went wrong, and was tempted to call Mash over it but…

Maybe he could weather the storm. After all, Jack was not actively trying to fuck him and the girl, despite her body, was not a real kid. There were so many reasons to be morally conflicted about this, but, deep down, Gudao was a bit too tired to burn his brain like this.

It was meant to be the holidays. It was meant to be his much-needed and deserved break. Plus, Jack was being reasonable and didn’t seem driven by inhuman lust for him like many other individuals that he knew best to not ‘summon by word’.

Sighing calmly, the Master of Chaldea brought Jack closer to him with a hug, triggering a giggle out of her.

Such was the life of a man that tends to please others beyond his own tastes and limits truly were…

—-------d-d-d-d—-----

AN

More Jackie? Or someone else? I want to see suggestions in the comments!