Chapter 9
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Translator: penny
Chapter: 9
Chapter Title: Corporal Punishment (2)
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"!"
Getting my ass spanked one by one by the maid sisters? The moment I heard Helena's suggestion, I flinched and shuddered.
At the same time, my ass clenched tight, making the dick wedged between my thighs twitch a little. Helena must have felt the movement down there because she smiled brightly.
"Hehe. Looks like the little guy down there is excited. So, should we ask the sisters to spank your naughty butt?"
"N-No... I don't want to..."
Even in my confused state, I shook my head vigorously. Just baring my ass was humiliating enough already. If I had to borrow their hands too, I wouldn't be able to endure it anymore...
When I refused so firmly, Helena tilted her head and said,
"Hmm? If you act like that, I might have to raise the punishment level, you know? You could get twenty—no, thirty more spanks on your butt, or..."
*Squeeze.*
"...turn around, sit facing forward, show off your dick, and ask the maid sisters to stroke it for you?"
Helena squeezed my thighs hard, teasing the shaft and base of my dick as if urging me to cum. I held back the rising pleasure of ejaculation as best I could and shouted,
"Th-That's absolutely not happening!"
Getting my ass spanked was embarrassing, but having my dick touched by hand was even worse. I'd rather take the spanking. And cumming from the other maids' hands in front of Sylvia felt wrong too.
"Hehe. Got it. Then we'll go with the first option."
Helena gave my ass a light pat like it was cute, then asked Sylvia for permission.
"Is that alright with you, Head Maid?"
"Yes. All authority over education belongs to you, Lady Helena. Do as you need."
"Thank you~"
With Sylvia's permission, Helena, who had been standing in front of the blackboard watching, called over the maids.
"Everyone~ Come over here~"
At Helena's words, the maids approached me along with Sylvia. They ogled my bent-over ass and made their crude remarks.
"Oh my, how cute~"
"Look how red that butt is. Like a monkey's."
"He's a human boy, after all. His skin is so delicate."
The sisters giggled as they inspected my ass.
I felt my face burning hot and clenched my ass tight to hide my balls from them.
But they didn't just look at my ass—they scrutinized me bent over and even Helena's thighs.
"Hey, is that... a dick wedged between Lady Helena's thighs?"
"Nah, no way."
"No, it really is. He's not gonna cum while getting his ass spanked, is he?"
I desperately hid my beet-red face and vowed not to cum no matter what.
*Click-clack- Click-clack-*
Like that, a dozen or so maids surrounded Helena, who was seated at the podium, in a circle. Their shadows loomed over me.
No doubt about it—I felt just like a woman about to be gang-raped by a bunch of men.
Even with my head bowed low, I could practically feel their heated gazes and warm breaths right beside me.
"Lady Sylvia, please come over here. I have a special task for you."
Helena called Sylvia over and had her stand by my face, where I was bent over. As Sylvia positioned herself in front of me, her swaying maid skirt and slender legs filled my view.
Remembering how she'd jerked me off to a massive orgasm, I tensed up my asshole and dick again.
Helena squeezed her thighs lightly in response, then asked Sylvia,
"Now, take a seat and face this boy eye-to-eye. Make sure he can't look away~"
"...Understood."
*Rustle-*
Sylvia knelt down on the floor right there, leveling her eyes with mine as I lay bent over Helena's thighs.
"!"
Sylvia's face drew so close I could feel her breath. Meeting her gaze made my heart pound wildly.
She stared at me silently with her usual expressionless face. That emotionless look both hurt my heart and turned me on.
My ass clenched on its own, and my dick twitched. Helena, reading my reaction, gently stroked my ass and asked Sylvia,
"Oh my, this one really likes you, Lady Sylvia. Was there some special moment?"
"While transporting him to the Demon King's castle, I helped him urinate once."
"That's all?"
".....No. In the process, I made him ejaculate once. It was hard for him to urinate while erect."
At Sylvia's explanation, the maids surrounding us chimed in.
"This naughty boy got off from the Head Maid's hand?"
"How'd you seduce her? Lady Sylvia doesn't usually step in herself."
"I'm so jealous~"
"I wanna make him cum too..."
Helena gauged the maids' reactions, then tapped my ass.
"Hehe. So it's affection for the one who gave him his first ejaculation. Perfect. Then, if I may be so bold..."
Helena whispered something in Sylvia's ear. Sylvia pondered briefly before nodding. Then.
*Rustle-*
Sylvia slipped both hands under her skirt and slowly removed her panties.
"!"
What emerged from under Sylvia's skirt was a pair of ornate black lace panties—hard to believe they belonged to the stern, businesslike Sylvia.
Afterward, she pried open my mouth and stuffed the panties fully inside.
"Mmph! Mmph!"
The whole process was so shocking yet natural that I accepted Sylvia's panties into my mouth without resistance.
The lace scratched my tongue, the elastic band felt chewy, and there was a faint sweet-tangy scent and taste.
Helena scratched my ass lightly with her finger as I tasted the panties and whispered in my ear,
"Now, with your beloved Lady Sylvia's panties in your mouth, get your ass thoroughly spanked by the other maid sisters until you cum~"
"Mmph mmph!"
I shook my head no and tried to protest, but the panties gagging me muffled everything.
"Alright, everyone~ Spank him as hard as you want!"
"Yes~!"
At Helena's go-ahead, the maids closed in eagerly. And at the same moment.
*Smack-*
A fierce hand struck my ass.
"Mmph!"
Unlike Helena's expert touch, this was a merciless palm strike. Unlike before, the pain made my vision blur as I exhaled sharply. But this was just the beginning.
The force, speed, and angle varied—no way to predict it—and the ruthless ass assault continued.
*Smack- Smack- Smack-*
"Look at this juicy thing!"
*Smack-*
"Twitching so cutely~"
*Smack-*
"Bad boys... need to be punished..."
*Smack-*
"Mmph mmph! Mmph!"
In the haze of the relentless barrage, one maid grabbed my tightly clenched cheeks instead of spanking and pried them apart.
"Can I spread these cheeks?"
"!"
Just as my hidden asshole and balls were about to be exposed, I snapped to and clenched hard against her. Then.
"Hiding won't do!"
*Smack-!*
The smash, full of emotion, hit like lightning through my ass.
"Mmmph!"
It hurt. So much. The pain brought tears to my eyes. I writhed in resistance. It was almost funny, but terror gripped me that I might actually die like this.
Did getting spanked hurt this bad? I might become the first person to die from a hand spanking...
*Smack-!*
The pain on my boy's body weakened my mind. Trembling in fear, I could only endure the continuing palm barrage.
Just as I gave up everything and squeezed my eyes shut, then.
*Stroke-*
"!"
A warm touch on my cheek made me open my eyes. Sylvia, who had been silently watching me writhe in pain, now cupped both my cheeks with her hands.
Then, she gently wiped the tears from my eyes with her slender fingers and said,
"Don't worry. I'll be right here with you."
"..."
Though Sylvia's face remained nearly expressionless, her sincerity reached me. With her panties still in my mouth, I nodded quietly...
It was only nine spanks, but the hellish time finally passed.
"Okay~ That's enough~. Everyone, step back."
Helena pulled back the maids who had been spanking me, then said softly,
"Now just one last spank remains. I'll handle the finale myself~"
She placed her hand on my glowing red ass. Already tender from the beating, even the mere touch stung fiercely.
As Helena stroked my ass gently, she soon slid her finger between my cheeks. I clenched instinctively, but her finger had already invaded the crevice.
"Your ass is plenty sensitive now~ And all that built-up pain too. How about we convert that pain into pleasure?"
*Brush-*
With those words, Helena's finger grazed my asshole lightly.
"!"
The instant her finger touched it, a floating sensation surged through me, and I clenched my hole hard. My dick between her thighs wriggled wildly too.
Helena looked at me and said,
"Hehe, you have talent. Pleasure and pain are just a hair's breadth apart. With all that accumulated pain, your anus is super sensitive right now."
*Slurp-*
Helena sucked on the finger that had touched my hole like it was delicious.
"Training this cute ass would be so intriguing, but..."
"Mmph mmph! Mmph!"
I twisted my whole body in protest.
A-Ass training? Anything but that. Losing a man's pride like that—no way. Sure, my pride was already gone with my dick between her thighs while getting spanked, but still, no!
"Well, we'll get to that later. We have plenty of time. For today, seeing the potential is enough."
Helena gave me a scary look, then grinned widely and raised her hand high.
"Anyway, time to wrap up the punishment~."
*Whoosh-*
Her hand sliced through the air toward my ass. Faster and fiercer than any previous strike.
'Fuck. I'm dead.'
I braced for the pain, squeezing my eyes shut and tensing my whole body. But.
"!!!"
What struck my ass wasn't pain—but an indescribably intense pleasure.