Of Babysitters and Caretakers - Alolan Rumble 1 (Patreon)

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

WARNING: This is not a ‘single-plotted’ story. It’s a mini-archive for small stories regarding, as the title mentions, Babysitters and Caretakers of the OC/MC kind dealing with lewd brats that are out to get some action. This means Loli action, this means that it’s fiction, this means that some canon logic is secondary due to the circumstances being absurd in itself. First and Last warning on the matter~.

Episode ‘Poké-Troubles: Alolan Rumble (Sarah & Harper)’

“I am so sorry for the lack of warning on the call, but it’s a bit of an emergency.”

The apologetic voice of the woman I was talking with was quite genuine, and I offered a sheepish smile while hiding away my thoughts of this golden chance being served to me like this.

The woman was a glorious MILF. She had been my neighbor for years and I had helped before with some babysitting for her oldest daughter, Lana, when I was just a teen. So, for me to be the babysitter for her young twins felt like a reasonable choice… and it got me closer to get that sweet huge ass of hers to pound.

I always had this interest towards this widowed lady, the blue-haired beauty having aged like wine and… I would have never missed the chance to get another reason to coax her to a date or two.

“It’s alright, miss. I had nothing to do anyway and I know that your situation is not easy, so I will handle it accordingly and without any issues.”

She beamed at my words and then proceeded to leave with her older daughter in tow. Lana smiled at me, waving shyly as it’s been a while since I have seen her and she had grown gorgeous.

Still, my sight was on her mother, so I planned to do a good job as a babysitter for the kids and… it wasn’t as simple as I had envisioned. I had been so ‘blinded’ by my experience with Lana that I thought it would have been the same.

The first sign of trouble came in the form of the girls setting a fart bag right by the pillow I sat on when talking with them by the couch. Childish humor was expected, I just didn’t think it would have been so outrageously frequent.

I ‘forgave’ this trick as it was a lame and tame one, but it seemed to just spurn the duo to try and chip at my sanity with other pranks. First was a Mr. Mime variant of the jack-in-a-box cookie box that made me jump and sit on a tiny cake they had cleverly put on the counter right behind me so that I could get my butt ‘caked’.

I gritted my teeth, but I cleaned myself with a towel, ignoring the cheeky giggling at the sight of my pants’ ass smeared with whipped cream. I thought this could have not gotten worse… it did.

For a hour, the kids were in their room, ‘drawing’ from what they told me but clearly up to no good as I walked up to them to tell them that lunch was ready and-

“Girls!”

Twin giggles echoed around the home as I gave chase to the naughtiest brats I had the unfortunate chance to babysit. Harper and Sarah were not like the more introverted Lana.

The girls were giddy, prankful, and already testing my patience as they set a bucket with water over their room as I went to check them, then bolted out of the room while I was distracted to avoid punishment in a game of chase around the house.

A futile effort as I caught up to them, and gave them quite the lecture. I was fine with the previous pranks, this one was beyond the fine line of making it dangerous. The water was cold, and it had almost made me trip on the ground when I turned to give them chase- hell, they tripped a few times along the chase due to their wet feet, and it was only by luck that nothing bad came from this.

“It could have hurt you both. I can handle it, but you two should have paid more attention to this- what if you had been injured? Who would have laughed then? How worried would your mother have been?”

No smiles, no chuckles, no smugness, only… awkwardness and upset. I didn’t tell them anything beyond going to the dining room as I prepared them lunch. Hell, I had gone as far as to make them their favorite stuff because I wanted to make peace with them- but no, this felt like a bit of a stab in the back.

I had rough kids, but they were spoiled. I would have to tell this to their mother as it was clear they were kept with little to no leash when meant to behave well. They were too feisty and too reckless, and there was a chance they could end up hurting themselves in these pranks.

I told them to play in the living room and not go in the garden or courtyard while I went for a shower. I could already feel the hints of a cold coming to me, but I was also worried of anything else coming from wet clothes and hair.

As I put my stuff on the side and entered the pristine clean shower, I turned on the hot water and started to clean up. I really needed it as I was deep in the rage cage. I had my eyes closed as I dealt with the shampoo bit when I heard someone clear their throat.

My eyes snapped open, the threat of those burning due to the shampoo mostly over as I had been through that aspect of the shower but… I was more concerned by the twins having entered the shower without me noticing. And in a rather peculiar set of swimsuits that were a bit too transparent for their sake.

“W-What are you two doing here?!” Panic was the first thing that came to mind. I mean, I was not prepared for this- this potential scandal ready to land me to jail so early on and-

“We are here to apologize,” Sarah said, her voice a bit more ‘tomboyish’ compared to her twin. “We went too far.”

Harper was blushing over one thing as she kept quiet, but I focused on Sarah. “And you decided to do this now while I am in the shower… why?”

Sarah huffed, then poked her sister out of her dick-induced trance. Her eyes went wide, with her attention up to me.

“I-It’s…” She gulped nervously, appearing very embarrassed so suddenly. “It’s complicated.”

“Harper!” The tomboy whined, making the girlier twin flinch a bit. “You promised that you would have told him already!”

“What do you want to tell me, Harper?”

The shy girl’s humming picked up and then she huffed. “I like you!”

…

“Huh?”

“I-I have loved you for a while, big bro. Ever since you were there to help us around when mama was out and busy  with her chores at work, I always looked up to you. Plus, you were also babysitting us when Lana needed it, so you were there too and… and I like how nice and mature you are.”

…And that’s a bit weird. Cute, but still weird.

“I-”

“And-And I will not take other men like Mama did after dad left! So you can rely on me on that too!”

That was interesting and… wait, what did she just say?

“Your mother-”

“She sleeps with clients at the onsen,” Sarah assured flatly, further crushing my ideal vision of the woman. “Hell, why do you think that only a few of those ‘family emergencies’ she brings Lana with her? The times she doesn’t bring big sis is because a client is willing to pay extra for her services.”

…

“You didn’t know, didn’t you?” Sarah asked cheekily, but rather than wait for my response, her sister made a move.

“I-I will not be like her, big bro!” Harper assured, hands on my cock and making me tense up a bit as she started to rub it with her palms. “I love Big Bro, and only big bro!”

Arceus, I am not ready for this awkwardly sexual situation!

Sarah licked her lips as she seemed aroused by the sight of her sister playing with my dick, twitching as she was my length throb due to the pressure exerted by her twin sister and… I came.

It was a bit of a quickshot, but it was mostly due to the fact this was… well, this was so sudden. The extreme turn of events acted as a strange turn-on to me and I ended up creaming faster than I would on a normal basis.

Cum propelled and landed on Harper’s chest. She smiled, but didn’t reach out to ‘eat’ it or even sample it.

“Mama always said she didn’t like to drink it so… I don’t wanna. Is it fine?” I was a bit surprised by this brief apology about it as the girl had caught me on it and… I sighed.

“I don’t mind, kiddo.”

Harper beamed and then had a bit of an embarrassed smile on her face. “A-Also, how did you feel about it, Big Bro? Was that good?”

I nodded. “It was very good.”

I saw her stand on her tip-toes and frowned. “Do you want a kiss or a head pat?”

“Maybe both,” Sarah snickered much to poor Harper’s awkward look.

I leaned down and… did just that, a hand resting on top of her head and my lips briefly tapping against hers. Her face burned red for a moment, but I turned to Sarah with a cheeky look.

“What?” She inquired quietly and I reached out for her head. “Oh? Are you going to kiss me?”

“Well, nope.”

She frowned, and then she tensed up in delight as she felt my other hand slithering to her crotch, pulling the fabric slightly away and… rubbing along her little slit. She shuddered, maybe thinking I would go for more but… I just had to rub for a brief amount of time to get her to climax.

It was there that cleaning up started. Both looked a bit ‘overwhelmed’ by the experience and I had a lot to think about. After cleaning up, the rest of the day moved as smoothly as I originally envisioned. We played a few tabletop games, and then finished my visit by checking the TV for some toons around.

When their mom and Lana were back, both looked pleased to see the house had survived the day. What the MILF didn’t know was that I now had reasonable doubt to check on her work situation to see how true her twins’ confession was about her promiscuous jobs.

I had a feeling they didn’t lie to me about it, thus tarnishing the chance of marrying her and being her new husband in the near future. But while that was indeed a sad loss, I had a feeling that Sarah, who was snoring on my arm while hugging the limb as a pillow, and Harper, who was sleep-sitting on her ‘rightful throne’ which was my lap, were both going to make an effort to ‘fix’ this issue.

What I didn’t know was, however, that this was just the beginning of my crazy new life tied to this family.