Making Kakyoin Proud 1 (Patreon)

Making Kakyoin Proud - or ‘The Dark Irony of a Dead Sith Lord creates a most wonderful Empire’ (MILF-Hunting Stories)

Episode: ‘Poké-Adventures: The Way of the Sea (1)’

Being a good fellow can lead to some interesting endeavors.

I wouldn’t say I am the bestest of boys, not with the kind of Search History I got stuck in my PC, but the thing is… there’s no fucking I will stop trying to get close to mature women. I am talking of MILFs, ladies that were deft and experienced in the matters of romance and sex.

My inclination towards the motherly kind came from the fact I found some of my past girlfriends’ mothers kind of hot. Nothing ever came from those attractions as I was a committed lover in my relationships and I hardly planned to be a homewrecker anywhere.

This led me to drop a few good stories to focus on my long-term dream of settling with a mommy kind of lady. The one that could ‘Ara Ara’ and yet be a softie deep within. Thus, my hopes came to manifest when I arrived in Alola.

The place was known as a major region for retired couples. While elders preferred it, some MILFs were also known to have taken the chance to settle in Alola. And after looking around, I found her.

Short blue hair, a curvaceous body with just a tiny bit of sagging, but overall a motherly lady alright. Ms. Kari was the mother of three children, all daughters. Lana, the oldest, was the shy girl, while the twin girls that were Sarah and Harper were absolute nightmares. In a sense, I could understand why they were like this.

Kids were young, their mother was very busy and they were hyperactive. Likewise, Lana was the kind of girl that was ‘awkward’ to many due to her asocial mindset. Nonetheless, approaching them proved to be ‘easy’. In the sense that, with the right amount of effort on my part to get close to them proved to be positive.

Three months in, and I was considered a common fixture in their household. I was unable to spend much time with the MILF herself, but helping her with the kids opened up the path to success.

I was invited to lunches and dinners, there were times the kids would pass by to study if the house was empty for a reason or another, and all in all, the woman was clearly noticing me.

If there is something I had learned from the Internet is that mere kink wasn’t enough. The MILF looked into the kind of guy that had the right amount of physique, mindset and cash. I wasn’t the dickish playboy, but rather the guy that worked hard for little (known) rewards.

Kari was the kind of lady that was quite lonely and liked to be laborious too, so she picked up on those traits we shared. Stuff happened, I was always the friendly goof ‘uncle’ to the kids and then she seemed to ‘shift away’ for a moment.

I thought I fucked up or something, maybe I had played my hand too harshly and got a whiplash effect or shit like that but-

“I wanted to ask you… would you like it if I tried to massage you?”

The offer was accepted, but I thought that it would start slowly. You know, still dressed and just focusing on my shoulder. The fact this came to happen in her house, in her bedroom, when the twins were out with their sister for some school-related stuff, should have been a big enough flag to show this was going to develop differently.

And it sure did when I arrived at the house, found the door open and Kari alerted me that she was waiting in the bedroom.

My jaw fucking dropped at the most arousing sight ever!

Here she was, kneeling by the ground in front of the bed. A towel prepared right in front of her as bottles of oil and lotions were set right by her side. But the most boner-inducing thing was her outfit. It was a rather skimpy light-blue sleepwear that showed a lot of skin.

“S-Surprise~,” Kari nervously greeted. “If- If it is too much-”

“It’s perfect,” I blurted out, barely covering the huge tent I pitched at that sight. “Y-you are perfect.”

Her cheeks flared red at the compliment, the blunt words catching her off-guard like she did with this surprise. Still, after stuttering her way around the flattering terms, Kari managed to explain what she had in mind.

“I-I just wanted to thank you properly. You- You know, for being quite caring with the girls and helping around. It means a lot to us.”

I smiled confidently. “It’s alright-”

“I-It isn’t fine actually,” She huffed, stunning me with the interjection. “A young man such as yourself, always focusing on us and- and I’ve seen the gazes you aim at me, it is clear what you want.”

I gulped nervously, unwilling to let her finish as I preferred to confess rather than being called out on it.

“Y-You wanna have sex with me!” “I love you!”

We both paused, and I shrunk at that awkward guess.

“W-Well; I wouldn’t mind doing that too, but I would never impose.”

“You…” Kari was too busy grasping what I just told her. Something beyond what she expected. Instead of the youngster looking to prey on her MILFy body and nothing more, she got herself a youth smitten and craving for more than just carnal pleasure. “You mean that- that even if I am a mother-”

I nodded.

“A widow-”

I nodded again.

“An old lady- you want me?!”

“Old?! No, you’re mature and gorgeous. A wonderful lady that is experienced and knows where the true focus should be in a relationship,” I retorted with a smile. “You care immensely for your daughters and try your best to make time for them. The fact you are also gorgeous is a plus, but I love you for being you.”

Her face was burning a bright red, and Kari took a few minutes to properly digest what was going on.

“I… You mean it, don’t you? All of it?”

“Yup, I just love you lots, Kari.”

She shivered at being called by her first name rather than ‘Ms. Kari’. I bet that was a bit of a change she wasn’t prepared for, but that the MILF loved nonetheless from the pleased smile she mustered at that.

“Which is why, to prove I mean it, I would like for us to not have sex today.”

Surprise flashed, but Kari appeared somewhat happy and yet sad at the same time.

“I… see.”

“We could still play a little if you want,” I offered, as I could tell she wanted to experience some action. “You know, with some foreplay?”

Since the massage thing kind of felt a bit awkward now that stuff was revealed, it would be a lie to think it could still be done as Kari had envisioned. However, that didn’t mean the lotion and the oil was to be wasted.

Despite some perplexity, Kari was soon lying beside me, our clothes ditched as our oiled hands caressed each other. She was a shuddering thing with my careful hand, while hers were clearly attracted by the big thing that throbbed for her.

She was baffled by my size, but she found it difficult to gawk at it when I had her lips stolen for a kiss. Kari may be a wonderful loving mother, but she was still a woman- one that had been missing on sexual depravity for a while. The way she was stroking and milking my cock, aiming the head right at her stomach made me realize how much she wanted a sticky cum bomb deep in her whorish womb.

I may love her and all, but a bitch was still someone needing to get her hole filled up with enough whipped cream to produce a new child or more. Hell, I bet the girls would love to have some more siblings to play with.

“I am about to cum, luv~,” I muttered through the smooching, seeing Kari’s eyes widening partially as she started to stroke harder.

Her legs had been squeezing for a while, my hand dodging the crushing as I had her cum at least twice before I delivered some sticky ropes of fertile jizz onto her belly. Roughly a minute later, we stopped kissing, and we were both sweating bullets and in clear need of a shower.

I claimed the first turn as the woman needed a break as she took to rest on the bed. I was quick to clean up, knowing that Kari needed enough time to get everything fixed before the girls made it back home.

By the time I was done washing, I found the woman resting on the bed, eyes open but her belly now missing the cum stains I left there. No napkins were around to be used, and Kari was looking away as I approached, an embarrassed look on her face… and tiny something of white sticking by the side of her lips.

For precaution, I kissed her on the forehead.

“See you soon then, Kari,” I saluted, ready to leave when I was stopped by the doorstep.

“W-Wait!”

I paused, looking over my shoulder back to Kari. “Yes?”

“...Saturday, I am free and the girls are out for a special exhibit with Professor Kukui.”

I beamed, this was an opening for a date. “It will be a private thing, Kari. Don’t worry.”

She smiled back, shyly and looking like a little school girl for a moment.

Ah, I am so going to make her a pregnant mommy again~.

—-------d-d-d-d—------

AN

Same rules as Of Babysitters and Caretakers, except it’s MILFs and not Lolis/Mesugaki.

Suggestion are accepted on ‘MILF targets’, and Netori is allowed in limited use: I will not accept ‘vanilla’ Netori, but I will accept if there is ‘reason’ for the cheating, such as an already infidel partner, a horrible partner, an abusive partner or other specific reasons that render the Netori a necessity to ‘make Kakyoin Proud’.