Chaldea Subjugation Organization (Fate/Grand Order)

As he sits there, listening to a lecture on magecraft, Mahatma, and other such things, Shigure finds himself pondering, not for the first time, the woman known as Helena Blavatsky. She was a Servant of course, HIS Servant, but she was also much more than that. Of course, just because he was thinking about her and all the mystery surrounding her didn’t mean that he wasn’t listening. He was the motherfucking Master of Chaldea, being able to multitask was pretty much an ironclad requirement.
 
So, even as he found himself studying Helena Blavatsky for the umpteenth time, his pen was also scratching across the paper in front of him as he took neat, orderly notes based on the information she was currently supplying him with. Hell, the fact that she was even willing to supply him with as much knowledge as she had made her something special, in Shigure’s humble opinion.
 
Helena Blavatsky, a female occultist from the Nineteen Century, and the founder of this thing called ‘theosophy’. From what Shigure had heard, theosophy was a collection of philosophies, invented by the female Servant standing before him today, all about how knowledge of God could be achieved through numerous different methods.
 
Basically, the Theosophical Society itself had doctrine, but refused to treat said doctrine as dogma. The only tenet theosophists were expected to subscribe to was a commitment ‘to form a nucleus of the Universal Brotherhood of Humanity without distinction of race, creed, sex, caste, or color’. Which to be fair, made a lot of sense based off of what he’d seen of Helena so far. The woman was kind and generous to a fault.
 
Rather than hoarding all of her knowledge, she was eager to share it… which made her all the stranger, given that she was also a magus, as it so happened. The amount of magical knowledge that the occultist had in her head was no laughing matter, and Shigure knew that he was lucky to be learning at her feet, to be given this chance to study what she had to teach him. It would undeniably make him more powerful at the end of the day.
 
He just wasn’t sure he could have done so in Helena’s place. He was well aware of his own personal faults. He could be greedy, he could be selfish, he could be vain. He accepted these parts of himself, and even embraced some of them. What was truly wrong with wanting it all, after all, so long as one had the power to reach out and take it? What was so evil about being selfish, when he was literally humanity’s last hope, the only Master left in all of Chaldea? And what was so bad about being concerned with his looks, with his strength, with his image? He had so many Servants to control and to keep in check. He had to seem strong to them, he had to seem untouchable.  Shigure’s greatest asset was without a doubt his reputation.
 
Even still, he could admire Helena Blavatsky, in a way. She was a smart woman, with a whole lot of power, and she was willing to share that with whoever asked… she was willing to share that with him. It pleased Shigure, and it seemed to make her happy as well, since he’d taken to her teachings like a fish to water, eager to consume everything that she could give him.
 
Though, that didn’t change the fact that her appearance ran a bit counter to her attitude and knowledge. Shigure blamed the Throne of Heroes, or the Summoning Circle, or whatever it was, because really, how else had someone like Helena Blavatsky come out looking like a young girl? He knew for a fact that she WASN’T a young girl. She was an adult woman in mind, very much so in fact.
 
But in body, she was positively tiny, petite and flat chested and just plain… small. And yet, she didn’t dress like a girl. On top of everything else, she dressed like a woman, despite her girlish figure.  From her bared shoulders to her exposed thighs, she was showing off a somewhat indecent amount of skin, despite wearing thigh-high stockings and shin-high boots, and even flowing, loose, disconnected white sleeves.
 
Her main attire was a corset dress with a skirt so short and frilly that every time she turned around to write something on the chalk board behind her, Shigure’s eyes were drawn down to her ass for a moment, her frilly skirt flipping up from the sharp motion to expose her pert, pale little behind and the black pair of panties she was wearing underneath.
 
Needless to say, Helena Blavatsky was just too cute to be a teacher, and as much as he was learning at her hands, it was getting harder and harder for Shigure to keep HIS hands to himself. He wanted to touch her. He wanted to fondle her and play with her… and fuck her. He wanted so badly to fuck her. But so far, their relationship remained completely platonic, that of a teacher and student.
 
He was looking for openings, to be sure, but none had cropped up just yet, and Shigure didn’t want to force the issue when he still had more to learn. Perhaps if he couldn’t find a way before they were finished with these lessons, he would do something once she’d taught him everything she knew. That sounded a little rapey in his head, but it wasn’t like he wouldn’t make it feel good for her as well…
 
“… after all, even I am something of a special case. Due to my own magecraft, I have been able to retain my youthful looks, despite my advanced age!”
 
Shigure blinks, suddenly pulled out of his thoughts as he finds himself focusing fully on what Helena is saying. Scoffing, he looks from her ass up to her face as she turns to regard him with a slight smile.
 
“Oh, come off it, I know you’re older than you look, but you can’t be THAT old… you’re too cute!”
 
Helena’s smile drops, and a blush spreads across her face as her eyes widen slightly.
 
“B-But I am… I-I really am.”
 
And like that, Shigure sees his opening. He can scarcely believe that it’s this easy, but hey, he’s never been one to look a gift horse in the mouth, now has he? As Helena blushes profusely, for the first time acting like a woman first and his teacher second, Shigure makes a big show of ogling her, chuckling as her blush deepens.
 
“No way!”
 
Helena nods jerkily.
 
“Y-Yes way… I’m… I-I’ll have you know that I was fifty-nine when I died, young Master!”
 
Shigure raises both eyebrows at that, making another show of eyeing her petite, girlish figure up and down again. As she fidgets and squirms under his gaze, he notices that she doesn’t try to stop him, nor does she make any effort to change the subject or get them back on track, back to the lecture she’d just been giving. Letting a slow grin spread across his face, Shigure leans forward in his seat.
 
“So, does that mean you’re a GILF then, Madame Blavatsky?”
 
Some confusion comes through her embarrassment as she furrows her brow and purses her lips together most cutely.
 
“A-Ah… a… GILF? I don’t believe I’m familiar with that term, young Master. What is a… GILF?”
 
Just hearing her say it out loud has Shigure chuckling as he leans back again and shrugs, a cocky, confident grin on his face now.
 
“It’s an acronym, Madame Blavatsky. An abbreviation, if you will. It stands for ‘Grandmother I’d Like to Fuck’.”
 
Helena blushes even deeper, and her eyes go wide for a moment before she ducks her head, getting all stutter-y and shy. She waves a hand dismissively, trying to blow off his comment as she shakes her head back and forth.
 
“N-Now, now… there’s no way a y-young stud like you would want to sleep with an o-old lady like me, Master. I know you have many women c-closer to your age to choose from, all over Chaldea…”
 
So that was why he’d not been getting anywhere with her all this time? It wasn’t that Helena was prudish or trying to keep things strictly professional between them… she’d just not thought herself worthy of Shigure’s attentions. Scoffing at the very idea, Shigure stands up from his seat, causing Helena to freeze in place as he stalks over to her.
 
The dynamic between them has flipped like that. Where before she was his teacher and he was her student, now, she was the sexy, girlish GILF of a Servant, and he was the Master of Chaldea, ready to ravish her on the spot. Looming over Helena’s diminutive form, Shigure grins wolfishly down at the petite purple-haired Servant.
 
“I would, actually. Like to sleep with you, I mean. I really, really would.”
 
And then he leans down and captures Helena’s lips in a deep, passionate, tongue-filled kiss. His hands, meanwhile, slide down her back to her small yet firm ass, and Shigure squeezes down HARD on her pert behind, even as he makes out with the shocked but also incredibly aroused female Servant. His tongue plays with her tongue, and in return Helena reciprocates, though due to how much smaller her tongue is compared to his, it’s definitely Shigure in charge throughout the resulting makeout session that follows.
 
His masculine fingers knead into both of her butt cheeks through her black panties, under her frilly skirt, and Helena moans unconsciously into his mouth, seemingly not sure what to do with herself as she goes up on her tip toes just to keep kissing him. She’s completely lost for a moment, but that’s okay, because Shigure is there to find her and bring her in, to make her his own.
 
When he finally comes up for air, his hands still firmly gripping her ass, there’s a string of saliva still connecting their lips together. Helena, with her lips parted and breathless panting coming out from between them, stares at the strand of saliva for a long moment, her eyes very nearly going crossed in the process, before she suddenly jolts and blushes at the realization that he’s still holding her close, and still kneading her butt with his hands.
 
Half-heartedly (because if she’d really wanted to, she could have used her magecraft to push him away) Helena reaches up and places her small hands on Shigure’s chest, attempting to push him back and squirm out of his grip. With her eyes averted and her face red with shame, her words are soft and her tone despondent as she answers him.
 
“W-While I’m extremely flattered that you desire me like this, young Master, i-it wouldn’t be appropriate, due to the age gap between us…”
 
Shigure snorts derisively at that and all but ignores her, instead opting to pull one hand off of her hand just long enough to drag his cock out of the confines of his pants. Then, he spins the diminutive Servant around, facing her away from him before and thrusting his dick forward, right between her clenched thighs. Helena lets out an eep as this happens, as the difference in height between them means she’s stuck up on her tip-toes with his cock now wedged between her thighs and pressed up against her panty clad crotch.
 
Maybe if she was actually fighting him on this, he’d be willing to let it go, but she’s not making any real moves, and as she squirms against him, whimpering softly, Shigure can FEEL the wetness seeping through her panties and soaking his erection. Grinning, the young Master of Chaldea leans in close, bringing his lips up to Helena’s ear as he slides his dick in and out of her thighs from behind, basically fucking her but not quite fucking her, right then and there.
 
“Your body’s reaction to me says otherwise, Helena.”
 
Thrusting in and out of her thighs, engaging in some intercrural sex, Shigure grins wickedly as the GILF groans and moans, her hands now on either side of him, grabbing at his shirt. She’s no longer trying to push him away though, but instead clinging and holding on for dear life. Before she can gather her thoughts and try to resist again, Shigure goes on the offensive, reaching around and grabbing the top of her cute little dress and pulling it down to expose her tiny, almost nonexistent tits.
 
He massages and tweaks her nipples with both hands, playing with her breasts even as he thigh-fucks her from behind, teasing the poor little GILF right into oblivion. The pleasure causes any argument she might have had against continuing to die on her lips and be replaced by moans as she begins to hump her hips back into his crotch, her thighs rubbing and squeezing and squirming all along his pistoning prick the entire while.
 
Eventually, Helena manages to regain her voice, though she’s still audibly breathless, as well as somewhat nervous as she speaks.
 
“A-Alright… m-maybe… maybe we c-can do it… j-just this one.”
 
Shigure relaxes his grip as she slips away from him, stepping forward and then turning around, a truly massive blush on her face as the girlish GILF stares down at the big, fat cock that’d been between her thighs just moments before. Slowly, still a bit hesitant, Helena reaches under her skirt and hooks her thumbs into the waistband of her panties, before pulling them down her legs.
 
He can’t help but appreciate the way she shimmies out of them, causing the soft pale flesh of her thighs and the small curve of her booty to jiggle in the process. In the end though, she drops them to the floor and steps away from them, hopping up onto her desk and spreading her legs apart. Thanks to the short nature of her dress’ skirt, this of course has the effect of revealing her sopping wet pussy to Shigure’s eyes, even as Helena herself averts her gaze, looking away rather shyly as he stares.
 
“D-Don’t expect too much from this old lady, young Master…”
 
Chuckling, Shigure steps up to plate, sliding into place between Helena’s small, creamy legs and grabbing her by her soft thighs as he lines his dick up with her drooling quim and presses the tip into her entrance. Then, he leans in close, and whispers directly into her ear, an easy task with her head turned to the side as she looks away from him.
 
“You’re a total GILF, Madame Blavatsky. Let me show you.”
 
And then he thrusts into her, filling her girlish body with his cock even as the GILF-y Servant lets out a loud, wanton cry from the sudden intrusion. He penetrates nice and deep on that first stroke, ultimately bottoming out in her and hitting the entrance to her womb, her cervix, right at the start. Helena’s hands come up to grab at his shirt, and her legs wrap around his waist all on their own as Shigure goes to town on the cute GILF, fucking her roughly, right on top of her desk.
 
Would this change things between them going forward? Shigure couldn’t deny that it probably would, even as he plowed the beautiful purple-haired Servant nice and hard. Her insides were tight, and his cock was throbbing with need as it filled her, again and again and again. He was making progress on her womb, almost ready to push right in through her cervix, which was growing more and more battered.
 
Helena was helping with that, mostly through orgasming along his dick over and over again. Her insides would clench and squeeze, but more importantly she was releasing a veritable tidal wave of pussy juices every time he made her cum, causing her insides to become slicker and slicker, wetter and wetter, and his passage to become all the faster as a result. He fucks her, and he fucks her, until finally, he slams right through her cervix and into her womb itself, allowing him to sheathe every last inch of his big fat dick inside of the lewd little GILF currently spreading her legs for him.
 
The sheer force at which he’s fucking her cause the boots that Helena’s wearing to knock together behind him, her heels smacking into his backside the entire time. Her entire body actually shakes and spasms and jerks with the repeated thrusting he delivers to her, so small and fragile compared to his comparatively larger physique.
 
Either way, Helena is unbelievably tight around his dick, her pussy walls and her cervix and her womb all gripping along his length in an incredibly pleasurable way, her repeated climaxes only making the experience all the more arousing for him. Eventually, unable to hold himself back any further, Shigure cums with a loud groan, filling Helena’s womb with his seed directly.
 
The GILF goes stock still for a moment, and then tosses her head back, screaming his ears right off as she climaxes one final time right alongside him, her pussy walls milking his shaft of every last drop of his seed, even as some of her juices squirt out from around his massive prick. They both reach that height of nirvana together in that moment, the sheer ecstasy rushing over them at the same exact time.
 
And then it’s over, and Helena is panting in both pleasure and exhaustion, but still has enough strength to reach up and wrap her arms around Shigure’s neck, pulling him down into a soul-searing kiss, their tongues intertwining once more for just a moment before she pulls back and smiles at him rather sunnily.
 
“You’ve made me feel like a young girl again, Master.”
 
Then, she blushes and grows a bit shy as she averts her gaze.
 
“I-If it’s not too much bother to fuck an old lady like me, I-I wouldn’t mind going another round…”
 
Shigure chuckles and slides his hands down and around till he can grab Helena by her ass again. He lifts her up off of her desk and she lets out a yelp as she hurriedly tightens the grip her legs currently have around his waist in the process. Walking her backwards, Shigure sits back down in the chair he’d vacated earlier, with his magic teacher now in his lap, impaled on his dick rather than teaching him jack shit about magecraft.
 
But that’s alright, there will be plenty of time for lectures later. For now, Shigure takes hold of Helena by her thin hips and smirks at her as he begins to bounce her up and down on his cock, causing her to moan wantonly in response. Chuckling, Shigure shakes his head.
 
“it would never be a bother to fuck a hot little GILF like you, Madame Blavatsky. Never in a million years.”
 
Blushing, Helena buries her face in his shoulder as they begin round two, but not without Shigure noticing the pleased smile stretching from ear to ear.

-x-X-x-

If you'd like to read more of my work not seen on this website, check out Hentai-Foundry.com and QuestionableQuesting.com where I have over a thousand stories!

If you'd like to contribute to funding my writing at all, check me out on Patreon.com/Cambrian

Thanks for reading!