The White Wind Howls (25)
The White Wind Howls (25)
#118
"Watch closely while you die. Watch your asshole quiver and clench tight. Well, since you didn't introduce yourself, I'll just have to figure it out on my own, won't I? And while we're at it, let's find out exactly where all your weak spots are inside that asshole."
Slide———
I drove my finger in as deep as it could go inside her back hole, raking against the inner walls.
"Nnng♥"
There she was—now that was the Lily I knew.
"Stop grinning like an idiot and get your head on straight. We've still got unfinished business, don't we?"
Pop-!
When I pulled the deeply buried finger free, Lily let out a low moan and trembled faintly.
"Haa... haa..."
"Still, it really is fascinating. Is the anus naturally an erogenous zone? I mean, I knew it was possible to feel things through the anus, but you're shivering even harder than you do with your actual pussy."
I toyed with Lily's anus—her sphincter—with my thumb while pouring out scathing remarks.
"I don't have much experience with women, but... I suspect Miss Lily here probably has the weakest anus of them all."
Fumbling—
I spoke while sliding my finger in shallowly, enjoying the tightness of her sphincter. Lily's back pussy muscles kept twitching restlessly, biting down on my finger as if trying to resist the intruder.
Of course, to me it just looked like her asshole begging me to hurry up and put my cock in already.
"Look at it even now. Anyone watching would think I've got my cock buried in you and we're having sex."
"Hng—♥ Th-this is your fault, you know......"
"Why blame others? What did I even do to Miss Lily?"
As if punishing the bullshit Lily was spouting—nonsense that didn't even make sense—I shoved two fingers in and twisted them forcefully against her sphincter.
"Oooohk♥ You kept pestering me every damn day about wanting anal sex so—♥ you developed it so thoroughly that I ended up like this♥♥"
Hmm.
So Lily's back pussy had such a deep history!
I always really enjoyed studying history back in middle and high school—if I'd been able to go to university, I might have even wanted to become a historian.
In the end, I fell into manual labor and couldn't pursue it, but... shouldn't I at least work through that regret here?
"Oh, now that's new information to me. Honestly, being with Miss Lily, there's always so many new stories to hear. Is this a regressor's privilege?"
Squelch squelch

"Hahk... stop digging in my asshole—♥ at least stop playing with my sphincter before it gets ruined..."
"And what if I don't want to? Playing with this incredibly tight sphincter—isn't that just basic human decency?"
"Wh-what if it gets ruined... if it gets ruined, I won't be able to squeeze your cock properly..."
"I don't care even if your back hole gets loose. Though it would be a bit of a shame if the grip weakens."
"What does that—"
Squuuelch—
"What matters is whose hole it is, not how tight it squeezes. As long as I get to do it with Miss Lily, I wouldn't care even if your hole stretched wide enough to fit my forearm."
"No, I would care about that—haahk♥"
Chaaaak—
Still putting up resistance, huh.
To tame the feisty Lily, I drove both index fingers in deep and forced her anus open as wide as it would go.
Whoosh——
Lily's face flushed crimson in an instant, and she tried to pull away, but no chance.
The size difference between us was so great that Lily couldn't possibly escape me with pure strength.
"St-stop it—!"
Lily howled defiantly.
"And what if I don't want to?"
When I brought her asshole, spread wide open, close to my face, Lily panicked.
"I said stop it for real——!!!"
She seemed absolutely furious, but I had a lot piled up against you too, you problem-child missy.
Hooohk— hooohk——
Hot heat seeped out from Lily's back hole, and with it right before my eyes, it felt as if the warmth from deep inside her body was being transmitted directly.
"........."
No words came back from Lily after that.
"Alright then, let's return to the main topic. Let's do a little history study on exactly how your asshole got trained by the past me."
"............"
"Are you sulking?"
"I said stop it..."
"Hey, you're not actually sulking over something like this, are you?"
"I said I don't like it..."
"No, I'm enjoying myself just fine? And you're the one who broke the penalty and lied again, missy. Where exactly did those great House Rosenheim Sex Manners go?"
"......"
She knew she had nothing to say, clearly.
Still, if I push any harder she might end up hating me.
"If you manage to see this through, I'll give you my cock as promised."
"... If you don't keep your promise, I'll cut your cock off."
I answered while releasing the anus I'd been spreading with my fingers.
"Of course."
Squeeze—
The moment I let go, her anus tightened and sealed itself back to its original shape.
But now what?
The mood had cooled down a bit.
But—one of the few lessons I had learned in my short life was that in times like that, pushing through with momentum worked out better for both of us.
Squeeze. Squeeze.
I toyed with Lily's back hole using my thumb and asked boldly.
"Let's really finish what we were doing. Last time."
"...... Fine."
"When, and how, were you trained?"
Perhaps her arousal had subsided a bit, because Lily answered coldly.
"Before the war broke out... it was shortly after I started having sex with you, we began it together..."
This was something I'd heard before at the safe house. The content itself felt like it might be true.
"I don't know why you were so obsessed with my back hole... but we really did all kinds of things."
"Tell me about the one that stands out the most."
"...... Do you really have to hear that?"
"I want to hear it. It's not like it's someone else—these are things I experienced. I just don't have the memories, that's all."
"Haa... well, if I start going through them one by one... nghnn♥"
I stretched my fingers out long once more and dug into her asshole.
"So deep... we did things like putting water inside and tormenting me so I couldn't push it out......"
Squeeze...
That's a bit extreme. So that's why it felt like I'd done that before—filling up her stomach with water.
"Ah♥ anyway. Putting your cock in and pulling it out while making me smell your glans... making me beg for you to put your cock in......"
I'd have to try that later too.
"The one that stands out the most. Tell me about that one."
I angled my fingertips and pressed down hard against the inner walls.
"Hahk— th-the one that stands out the most... was keeping your cock inside all day, making my hole all loose and making semen leak out continuously......"
We did something that rough?
"How did that end up happening?"
Lily answered, her ass trembling with shame.
"Th-there was talk about trying to raise the sensitivity inside my asshole a bit more..."
Feeling a bit sorry for Lily, I gently stroked her ass and asked.
"That I made you do such severe things... I'll apologize on behalf of my past self."
Shiver shiver——
Suddenly Lily began trembling and pushing her ass toward me.
"Ah— no. That was something Lily asked for..."
Fuck, I felt sorry for nothing.
I bent the index and middle fingers that had been digging into her back pussy and pressed hard against the lower inner wall—the inner wall toward her pussy.
"Nngghhh♥"
At the same time—
I pushed my thumb inside her pussy and pressed upward hard against the inner wall toward her anus.
"Gk—aaaahk♥"
The sensation of gripping Lily's entire lower body with one hand.
The size difference between us was considerable, so I could vividly feel how her ass fit into one hand, utterly unable to move.
Drip. Drip drip.
Sticky pussy juice ran down my thumb and fell to the floor in droplets, forming thin threads.
Was Lily gradually heating up again?
"So what made you ask for such rough treatment?"
"Eeeeeek♥ let go of my ass—♥"
"Answer."
Kwaaak—!
I clenched the hand gripping her ass tight, fingers buried in both holes.
"Kkeueueu♥ I'll tell you so let go——"
I pulled out my thumb and gently rubbed her clit.
"Hooook— thank you for the clit—♥ thank you—! S-so, Lily got addicted to back pussy sex and— I got greedy wanting to feel it even better, and I begged you to train me—♥"
"There was never a more depraved pervert of a woman, was there? And yet last time at the safe house, you acted all innocent like you weren't like that."
"Y-you jerk... you started it all—!"
Hey now. Maybe it had started that way, but that was her true nature.
Smaaaak—!
When I smacked her ass with my left hand, waves rippled across Lily's buttocks and a red flower bloomed on the white flesh of her ass.
"Haahk♥"
"Stop blaming others already. Anyway, after that, was your anus doing okay? Looking at it now, it seems perfectly fine."
Lily's ears were blazing like molten metal in a furnace.
"I-I asked my mother to fix it— I got scolded but I got it treated... I even learned how to make medicine to fix a loosened anus and... just give me the cock already—!"
Perhaps furious that even her most embarrassing dark history had been exposed, Lily shrieked and rebelled.
Ah— that was a satisfying exploration of back pussy history.
I'd have to do additional research later and write a paper on it.
"Alright then, since you've put in the effort. Let's study your weak spots directly with this cock."
Plap—
"R-really?"
"So, shall I have you beg for cock first?"
***
***
When I completely removed my hand from Lily's ass, she dropped down onto the floor as if it were second nature and spread her buttocks apart with both hands.
Against her white skin, red handprints bloomed like vividly colored flowers, and from the pussy spread open by Lily's fingers, sticky fluid dripped steadily like picketers demanding cock.
If Lily's pussy and back hole had personalities, they'd probably be fighting each other like crazy, wouldn't they? Split between the Pussy Disability Alliance and the Back Hole Union. For reference, Pussy Disability Alliance is the Pussy Disability Alliance and the Back Hole Union is the Back Hole Labor Union.
『Pussy Disability Alliance: Hey, you fucking Back Hole Union bastards! Stop neglecting the pussy—!! Why do you keep butting in and monopolizing his cock and making a damn scene?!
Back Hole Union: Bullshit. We're the ones who actually do more work around here, you know? The pussy's only used to exercise Unique Magic through the uterus— and the one who really knows the taste of cock and what he likes is the back hole, so you guys should just retire—!』
At that point, I supposed my pick would be the Back Hole Union side.
Whether my mind had gone mad to match this insane world, my head was filled to the brim with such ridiculous delusions.
And just as the delusions were winding down, Lily's low voice reached me.
"Y-you definitely said you'd give me cock now?"
A voice demanding the fulfillment of the promise.
"...... C-cock...♥"
I gently stroked her clit in time with her thin, trembling voice.
"Louder."
Lily's ass trembled and quivered.
She gritted her teeth—and then, as if finally resigning herself, took a deep breath and spoke.
"Your cock... please put your monster cock in and finish taming Lily's asshole... roughly fuck this bitch hole♥"
The Pussy Disability Alliance would be absolutely furious if they heard this.
I smiled with satisfaction and rubbed my large glans between her spread buttocks.
"One last thing. Tell me who the owner of Miss Lily's holes is."
Lily's voice was practically a wail by now.
"All of Lily's holes... my mouth pussy and my pussy and my back pussy— they're all yours♥ do whatever you want with them—!!! Your cock—!!! Hurry and give me the cock—!!!!!"
Thrust——
Lily's moans filled the riverbank.