Of Babysitters and Caretakers - Alolan Rumble 2 (Patreon)

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

Episode ‘Poké-Troubles: Alolan Rumble 2 (Sarah & Harper)’

I want to say that a lot has changed since that peculiar babysitting job but… I would be lying.

Did things change in some regards to the twins’ family? Definitely. I was less ‘driven’ to be the most jovial and reliable individual around their mother. The fact that a quick online search confirmed that she had been recorded being a slut around others in town was enough to kill any appeal to try and hook up with her.

Sure, she was a sexy bombshell, but I would always have this bitter taste in my throat whenever I thought of me ending up claiming ‘sloppy seconds’. Hell, did I even have a chance to begin with? After all, if she just became my wife, would that mean she would go behind my back to get fucked by other men?

As much as I could understand her plight for money and attention… it just wasn’t for me. Lana was the one ‘unchanged’ by this as I treated her as I would usually do this and… her sisters were those that took an immediate and radical twist to their behavior around me.

Harper in particular tended to be quite the ‘Lana 2nd’ around me with a note of forwardness at times when it came to hugging and sitting on my lap while we watched a movie or a show.

Sarah was less on the ‘causing trouble’ and more of trying something new everyday- one would say she took inspiration from a cartoon about two siblings planning to make the most out of their summer.

Since Alola was stuck in what felt like a perpetual summer, it made sense for the girls to relate to it so… yeah, some trouble was still in the air from time to time.

Speaking of my status as their babysitter, I would be called to check on them even without an emergency. Their mother was just ‘happy’ to know her daughters had gotten to like me to the point of wanting to be left with me around and thus allowed her to do more of her ‘job.

I felt like being slapped whenever she mentioned it. Her ‘job’. Maybe it was the butthurt talking but… fuck, what a waste! It was really tragic, but not enough to really render those visits too difficult to bear.

The twins, despite their promiscuous attitude, were particularly tame in their approach. Neither would start anything unless really spurned into it. So, it was quite common for some visits to just be me being a normal babysitter and the girls being polite and well-behaved.

Then… One day they decided to take it a step further.

With Harper busy in their room to draw alone, Sarah was listening to some videos from her tablet with her headphones on and me cleaning up the kitchen as we had just finished lunch, I thought that day would have been a slow but relatively calm day.

“Big bro!”

I was wrong.

“Yeah, Harper?” I asked a bit loudly, just enough for the girl to hear me without Sarah being disturbed by this.

“I want you to see some drawings!”

I sighed. “Coming up soon!”

After saying this, I finished cleaning a couple more plates, with only the glasses being left to be dealt with. I dried my hands and then proceeded to walk upstairs to where the twins’ room was.

I expected to be greeted by wholesome drawings, a lovely time with the cutiepie and then go back to my chores but…

“Harper?”

“Yes, big bro~?” The giddy loli asked, a lewd look on her face.

“Where did you buy that outfit?”

At that very moment, I was looking at Harper as she was resting on her bed, posing as she was wearing a yellow skimpy bikini with black ‘feline’ paws and a pair of cat ears on top of her head.

“Online.”

I am not surprised but-

“Any particular reason?”

She flashed her tongue. “Nyah, I am in heat, big bro. You need to help this kitty to be happy and not hurt from it.”

…

“You read that online, did you?”

Harper nodded, looking a bit nervous. “Was that right? Did I recite that wrong?”

“Let’s just say I was not prepared for a planned effort for some kinky acting. So… you want me to-”

“Sex! Yup.”

“You know it’s painful the first time? Like, I am not trying to be a butthead here, but one thing is foreplay, another is giving up your virginity to-”

“The one I love and the one I will always stick beside.”

A bit of a ‘ominous’ promise and proclamation but…

“You sure?”

“Yup.”

“It will hurt you a bit.”

“Is Big Bro a dum-dum?”

I frowned. “What’s that supposed to mean?”

“Well, if Big Bro is a dum-dum, then he will not let this hurt me a lot.”

“... Fine but… this is not becoming a frequent thing.”

She didn’t say anything at this, and I just found myself sitting on her bed, contemplating how ‘low’ my life had fallen. I was pining for a MILF and now I was meant to fuck with a Loli- a cute and loving one, but still… fuck, this was so messed up to some extent.

I didn’t back down, I felt ‘urged’ to give her something at least. I tried to think of what to do as I started to finger her. I removed the lower bikini, freeing her lil’ pussy. It was smooth and devoid of pubes. I started to tease along the slit, then pushed a single digit inside to prompt more juices out and lube her up. I was expecting a lot of regret coming as I released my length, a half-boner already growing to full mast as I rubbed it to full size.

Harper looked nervous, but she was breathing heavily right as she saw my dick lining up towards her pussy. A twitch and then… I pushed in. Slowly, gently, and thinking of stopping at pain as I pushed through.

I ended up pushing as deep as possible, only to pause as I stared at Harper for anything that could suggest pain. She did tense up, but she had a rather confused look on her flushed face. We both stopped for a moment, and I decided to just cut the chase.

“Does this hurt?”

She slowly shook her head. “...No~?”

A little moan tailed by the answer, but still, I thought that, maybe, somehow, Harper had lost her hymen in some unusual but not too rare circumstances regarding Pokemon. Riding some Pokemon that go at fast speed can do that to some girls from what I heard.

I pulled slightly away, seeing the girl squirm in pure pleasure and devoid of any unpleasant feeling. She was quite tight alright and, as I pulled away just enough, I saw she was bleeding too.

That’s the result of her hymen alright. Why is she not in pain?

Curiosity overruled any previous thoughts as I decided to put through a brief experiment which, surprisingly enough, became the starting point of the fucking. I decided that, rather than go slow on Harper, I had to give her a bit of ‘fast-paced’ fun.

Turns out she had nothing to complain about as she was suddenly overwhelmed by jolts of pleasure at getting pounded by a happy kitty. Her walls were stretching just enough to handle my cock, but had the tendency to tighten up with each climax the girl went through.

Considering the copious amount of squirting my lower chest was subjected to by her eager bean, I could tell that she was enjoying her first time far more than any of us could have predicted. And while part of me still wanted to play the ‘moral guy’, I couldn’t help but fall in love with the feeling.

Harper was totally hooked to this, damned to know the full extent of what this meant through her slutty mother and… She was doing this by her own decision to ‘ball chain’ me. I wasn’t sure how to feel about that last bit, but, at the moment, I decided to feel horny and ready to claim some personal pleasure back from her.

A few hours went by and… soon I was a bit spent by the experience. It was one of the most intense times I had and could have hoped to have experienced, yet I was still confused why was Harper able to handle that big of a cock and not feel any pain at having her hymen torn? Many women would have felt that, even a bit of discomfort. Not Harper, and this detail was confusing me.

After sitting by her side for a while, I used some napkins to clean the messy cunt she got. Even as I used five napkins her pussy was oozing fertile cream. She noticed me staring and-

“I-I took one of the pills earlier today. I am fine.”

“Glad to hear that,” I nodded, then offering a concerned look. “You sure you want to bathe alone.”

“Yeah… I am spent. I think I would jump you again if we were to go there together, big bro,” She explained mirthfully despite how drained she looked. “That was the funniest thing ever.”

I nodded in agreement, and put on my clothes as I walked out of her room to get back to my chores. Once I was done with the dishes, I sat on the sofa with Sarah and the other twin picked up I was staring at the black screen of the TV.

She turned off the tablet and focused on me with a curious look.

“So, you did it with Harper?”

I blinked, slightly surprised. “Yeah- you two-”

“We share all plans. I know and, don't take it as an offense, but we planned for our first times to be done individually from each other, Big Bro. We just feel that is for the best.”

I slowly nodded at this, not offended at all.

“I was more… confused about something,” I admitted. “Harper didn’t feel any pain when I first entered her.”

Sarah… frowned. Heavily. “For real?”

“You can ask her. We were both surprised and then I managed to do it with her a bit rougher than I had planned- she just took it without any sign of discomfort.”

“That’s… curious, yes,” Sarah admitted. “Actually, I think I know what it may be, but I have to check something with Professor Kukui first.”

Isn’t that the Professor for Pokemon in the region? What would he know about what had just happened- actually, was that even a good idea to bring the specific situation at all to someone?

“Why?”

“Well, there’s something he said about Humans and Pokemon, so I wanted to ask him how much a human can be like a Pokemon in some characteristics.”

…I wasn’t following.

“Still, I will not tell him you fucked Harper silly and into a happy loli.”

The smug look on her face as she dealt these words with the lewdest tone possible was absurd.

“You sure are a little pest when you want to be.”

She giggled, crawling up and deciding to steal a lap-hug while at it. She was nappy, so she fell asleep there too while at it.

What a cheeky brat.

—--d-d-d-d—---------

AN

Harper gets her Big Bro’s dick!

Next time, however, we will switch to another mini-series. This time, it is a ‘shy’ young girl that is not as annoying and ambitious as her big bro in becoming a ninja.