Chapter 9
"!"
Getting spanked by all the maid sisters... When I heard Helena's proposal, my body trembled involuntarily.
At the same time, my dick twitched between her thighs as I clenched my buttocks. Helena must have felt my penis move between her legs, as she smiled brightly.
"Hoho. Your lower part seems to be enjoying this. Well then, shall we ask the sisters to give you your spanking?"
"N-no..."
Even in my confused state, I shook my head vigorously. Just having my ass exposed was humiliating enough. If they were to use their hands too, I wouldn't be able to take it anymore...
When I firmly refused, Helena tilted her head and said:
"Hmm? If you resist like that, we might have to increase the punishment? Maybe ten more spanks, or twenty more, or perhaps..."
Squeeze-
"We could turn you around to sit facing forward, expose your dick, and have the maid sisters stroke it with their hands?"
Helena strongly squeezed her thighs together, stimulating my shaft and base as if urging me to ejaculate. Fighting back the rising pleasure of climax, I shouted.
"Th-that's absolutely not happening!"
Getting spanked on the ass is embarrassing, but having my dick stroked by hand is worse. I'd rather be spanked. And besides, it would feel wrong to ejaculate into other maids' hands in front of Sylvia.
"Hehe. Alright. Let's go with the first option then."
Helena lightly patted my buttocks before asking Sylvia for permission.
"Is this acceptable, Head Maid?"
"Yes. All authority regarding education belongs to Lady Helena, so as you see fit."
"Thank you~"
After getting Sylvia's approval, Helena called out to the maids watching by the blackboard.
"Everyone~ Please come here~"
At Helena's words, Sylvia and the maids approached me. They looked at my exposed buttocks while making lewd comments.
"My my, how cute~"
"Look how red his bottom is. Like a monkey."
"He's a human boy after all. Such delicate skin."
The sisters giggling while examining my ass.
Feeling my face burning hot, I tightly clenched my buttocks to hide my balls from the maids' view.
But they carefully examined not just my ass, but also where I was lying across Helena's thighs.
"Hey, isn't his dick wedged between Helena's thighs?"
"No way."
"It totally is. Think he'll cum while getting spanked?"
I tried to hide my tomato-red face while firmly promising myself I absolutely would not ejaculate.
Click-* *Click-
The dozen or so maids formed a circle around Helena seated at the podium. Their shadows loomed over me.
Though I didn't know for sure, I felt like a woman about to be gang-raped by men.
Even with my head bowed low, I could feel their heated gazes and warm breath right next to me.
"Sylvia, please come over here. I have a special task for you."
Helena called Sylvia over to stand by my face. When Sylvia stood in front of me, I could see her swaying maid skirt and slender legs.
Remembering how Sylvia had given me that handjob and made me ejaculate so intensely, I instinctively clenched my anus and dick again.
Helena slightly squeezed her thighs in response, then asked Sylvia:
"Please sit down and look him in the eyes. Make sure he can't look away~"
"...Understood."
Rustle-
Sylvia knelt down on the floor to meet my eye level as I lay across Helena's lap.
"!"
Sylvia's face so close I could feel her breath. When our eyes met, my heart suddenly started pounding.
She stared at me with her usual expressionless face. That emotionless gaze both pained and aroused me.
My ass clenched involuntarily, making my dick twitch. Helena seemed to notice my reaction, as she gently caressed my buttocks while asking Sylvia:
"My, this one seems to really like you, Sylvia. Was there some incident?"
"While transporting him to the Demon King's Castle, I helped him urinate."
"Is that all?"
"...No. During that process, I made him ejaculate once. Since it's difficult to urinate with an erection."
At Sylvia's explanation, the maids surrounding us chimed in.
"You naughty boy. Getting off with the Head Maid's hand?"
"How did you seduce her? Sylvia usually never takes initiative."
"I'm jealous~"
"I want to make him cum too..."
After observing the maids' reactions, Helena tapped my buttocks.
"Hoho. I see. Perhaps some lingering feelings for the one who gave you your first ejaculation. Very good. Then if I may be so bold..."
Helena whispered something in Sylvia's ear, and after brief consideration, Sylvia nodded. Then.
Rustle-
Sylvia put both hands under her skirt and slowly removed her panties.
"!"
What emerged from under Sylvia's skirt was an ornate black lace panty that seemed uncharacteristic for the businesslike and stoic Sylvia.
She then opened my mouth and stuffed her removed panties deep inside.
"Mmph! Mmph!"
The sequence was so shocking yet natural that I accepted Sylvia's panties into my mouth without any resistance.
I could feel the scratchy lace decorations and elastic bands filling my mouth. And there was also an inexplicable sweet and sour taste and scent.
Helena gently scratched my buttocks with her finger while whispering in my ear:
"Now let's make you ejaculate while getting spanked hard by the other maid sisters, with your beloved Sylvia's panties in your mouth~"
"Mmph mmph!"
I shook my head and tried to protest, but the panties filling my mouth prevented my words from reaching them.
"Now then everyone~ Spank him as much as you'd like!"
"Yes~!"
At Helena's permission, the maids surrounding me drew closer. And then.
Smack-
I felt sharp hands striking my buttocks.
"Mmph!"
Unlike Helena's expert touch, these were merciless palm strikes. Different from before, I gasped at the dizzying pain. But this was just the beginning.
The strength, speed, and direction of the spanking varied unpredictably as the ruthless assault on my ass continued.
Smack-* *Smack-* *Smack-
"Look at this delicious thing!"
Slap-
"So cute when it twitches~"
Slap-
"Bad boys... need to be punished..."
Slap-
"Mmph mmph! Mmph!"
In the midst of the endless assault leaving me dazed, one maid grabbed and spread apart my tightly clenched buttocks instead of spanking them.
"Can I spread his ass open?"
"!"
Just as my hidden anus and balls were about to be exposed, I barely regained my senses and resisted her by clenching my buttocks. Then.
"No hiding allowed!"
*SMACK-*!
A strike filled with emotion hit me like a bolt of lightning.
"Mmmmph!"
It hurts. It hurts so much. The pain was enough to bring tears to my eyes as I writhed in resistance. It may sound silly, but I was even struck with fear that I might die at this rate.
Can spanking really hurt this much? I could become the first person to die from being spanked...
*SMACK-*!
The pain inflicted on my young body, and my weakened spirit because of it. I could only tremble in fear as I endured the continuing rain of palm strikes.
Just when I had given up everything and squeezed my eyes shut.
Caress-
"!"
At the warm touch on my cheek, I opened my eyes. Sylvia, who had been silently watching me writhe in pain, held my face in both hands.
Then, Sylvia wiped away the tears in my eyes with her slender fingers and said:
"Don't worry. I'll stay with you."
"..."
Though Sylvia's expression remained nearly blank as she said this, her sincerity reached me. With her panties in my mouth, I quietly nodded...
Though it was only nine palm strikes, the hellish time had passed.
"Alright~ that's enough~. Everyone please step back."
Helena moved the spanking maids back, then spoke softly.
"Only one final strike remains. I'll execute this last one~"
She placed her hand on my bright red buttocks. My ass had become so sensitive from all the spanking that even a simple touch made it sting.
As Helena gently caressed my buttocks, she slid her finger between my ass cheeks. I clenched my buttocks instantly, but her finger had already invaded between them.
"Your ass is already quite sensitive~ And there's plenty of pain built up. Shall we try converting this pain into pleasure?"
Slide-
As she said this, Helena lightly traced my anus with her finger.
"!"
When her finger touched me, I felt an almost floating sensation and strongly clenched my anus. My dick wedged between her thighs also twitched on its own.
Helena looked at me and said.
"Hoho, you seem to have talent for this. Pain and pleasure are really just a hair's width apart. Because of the accumulated pain in your buttocks, your anus has become extremely sensitive too."
Suck-
Helena put her finger that had touched my anus into her mouth and sucked it deliciously.
"Training this cute bottom would be quite interesting..."
"Mmph mmph! Mmph!"
I twisted my whole body in resistance.
A-anal training? I can do anything else but not that. It would mean losing my male pride. Though I suppose I don't have much pride left being spanked with my dick between her thighs...
"Well, we can do that gradually. We have plenty of time. Today I'm satisfied just seeing the potential."
Helena raised her hand to the sky while grinning at me with scary eyes.
"Anyway, let's finish the punishment~."
Whoosh-
With a sound of cutting through air, Helena's hand struck my buttocks. It was faster and more forceful than any palm that had hit my ass so far.
'Fuck. I'm dead.'
I squeezed my eyes shut and tensed my whole body preparing for the incoming pain. But.
"!!!"
What struck my buttocks was not pain, but an indescribably powerful pleasure.