9. Punishment (2)
"!"
Being spanked in turn by the Maid Sisters. Hearing Helena's proposal, I flinched and my body trembled.
At the same time, my Buttocks clenched, and even my Dick, wedged between her thighs, twitched a little. Helena, as if sensing the movement of my Dick between her legs, smiled brightly.
"Huhu. It seems your lower half likes it. Then, shall we ask the sisters to spank your Buttocks?"
"I-I don't want to..."
Even amidst my confusion, I shook my Head vigorously. Just showing my Buttocks was shameful enough. If I had to borrow their hands, I wouldn't be able to take it anymore...
As I stubbornly refused, Helena tilted her head and said.
"Hmm? If you're going to be like that, I can just raise the level of the Punishment, you know? You could get ten, no, twenty more spanks on your Buttocks, or..."
Grip—
"Shall we have you turn around, take out your Cock, and ask the Maid Sisters to touch you with their hands?"
Helena squeezed her thighs tightly, stimulating the shaft of my Dick and its root as if to urge Ejaculation. I held back the mounting pleasure of Ejaculation as much as I could and shouted.
"Th-That's absolutely not happening!"
Getting my Buttocks spanked is embarrassing, but it's not as bad as having my Cock touched by their hands. I'd rather be spanked. And ejaculating at the hands of the other Maids in front of Silvia is... something else.
"Heehee. I understand. Then let's go with the first option."
Helena lightly tapped my Buttocks as if I were cute, then sought Silvia's permission.
"Is that alright, Head Maid?"
"Yes. All authority regarding Education belongs to you, Helena. Do as you see fit."
"Thank you~"
Having received Silvia's permission, Helena called over the Maids who were standing in front of the chalkboard, watching.
"Everyone~ Please come over here~"
At Helena's words, the Maids approached me along with Silvia. They watched my prone Buttocks and started spouting lewd jokes.
"Oh my, how cute~"
"Look at how red his Buttocks are. Like a monkey."
"He's a Human Boy. His skin is delicate."
The Nunas giggled as they watched my Buttocks.
I felt my face flush hot and clenched my Buttocks tightly to hide my Balls from the Maids.
But they weren't just looking at my Buttocks; they were carefully examining me and the area around Helena's thighs.
"Hey, isn't that his Cock wedged between Helena's thighs?"
"Nah, no way."
"No. It's really wedged in there. He's not going to ejaculate while getting his Buttocks spanked, is he?"
I tried my best to hide my beet-red face, vowing that I would absolutely not ejaculate.
Click- clack-
And so, a dozen or so Maids formed a circle around Helena, who was sitting on the teacher's desk. Their shadows fell over me.
I didn't know for sure, but I felt like a woman surrounded by men, right before being raped.
Even though my Head was bowed low, I felt as if I could feel their heated gazes and warm breath right beside me.
"Silvia, please come over here. I have something special for you to do."
Helena called Silvia over and had her stand where my face was. As Silvia stood before me, her swaying Maid skirt and slender legs came into view.
The memory of receiving a grand Handjob from Silvia and ejaculating surged back, and I once again flinched and clenched my Asshole and Dick.
Helena squeezed her thighs slightly in response, then made a request to Silvia.
"Now then, please sit down and face this boy. So he can't look away~"
"...Understood."
Rustle—
Silvia knelt on the floor and met my eyes as I lay prone over Helena's thighs.
"!"
Silvia's face, so close I could feel her breath. The moment our eyes met, my heart skipped a beat.
She was looking at me silently with her usual expressionless face. That emotionless gaze she directed at me was both heartbreaking and arousing.
My Buttocks clenched on their own and my Dick twitched. Helena, as if reading my reaction, began to slowly caress my Buttocks and asked Silvia.
"Oh my, this boy seems to really like you, Silvia. Was there some kind of trigger?"
"While he was being transported to the Demon King's Castle, I helped him urinate."
"Is that all?"
".....No. During that process, I made him ejaculate once. It was difficult for him to urinate with an erection."
At Silvia's explanation, the surrounding Maids chimed in one by one.
"This Insolent Bastard. He used the Head Maid's hand to ejaculate?"
"How did you seduce her? Silvia rarely takes the initiative herself."
"I'm so jealous~"
"I want to make him ejaculate too..."
Helena observed the Maids' reactions, then tapped my Buttocks.
"Huhu. I see. Is it a fond feeling for the one who gave you your first Ejaculation? Very good. Then, perhaps, if you'll excuse my impertinence..."
Helena whispered something in Silvia's ear, and after a moment of contemplation, Silvia nodded. Then.
Rustle—
Silvia put both hands under her skirt and slowly took off the panties she was wearing.
"!"
What emerged from under Silvia's skirt was a pair of ornate, black lace panties, unbelievable for the blunt and business-like Silvia to be wearing.
Afterward, she pried open my mouth and stuffed her removed panties deep inside.
"Mph! Mph!"
The whole process was so shocking yet natural that I couldn't resist at all and accepted Silvia's panties into my mouth.
From the panties filling the inside of my mouth, I could feel the scratchiness of the lace decorations and the chewiness of the elastic straps. And, for some reason, I could also sense a sweet and sour scent and taste.
As I was tasting the panties, Helena gently scratched my Buttocks with her finger and whispered in my ear.
"Then, with your beloved Silvia's panties in your mouth, let's ejaculate while getting your Buttocks spanked soundly by the other Maid Sisters~"
"Mph-mph!"
I shook my head back and forth and tried to say something, but because of the panties stuffing my mouth, my words couldn't reach them.
"Now, everyone~ Feel free to hit him as much as you like!"
"Yes~!"
The moment Helena gave her permission, the Maids surrounding me closed in as if they'd been waiting. At the same time.
Whack—
A sharp Hand came down on my Buttocks.
"Mph!"
A merciless palm strike, different from Helena's professional touch. Unlike before, I gasped out a breath along with a pain that made my vision swim. But this was only the beginning.
The power, speed, and direction of the spanking were all different, and a merciless buttocks attack continued, completely unpredictable.
Whack— Whack— Whack—
"Look at this delicious thing!"
Slap—
"It's cute when he flinches~"
Slap—
"Bad boys... must be punished..."
Slap—
"Mph-mph! Mph!"
As my mind grew hazy from the relentless assault, one Maid, instead of hitting my Buttocks, grabbed my tightly clenched cheeks with her hands and pulled them apart.
"Can I spread his Buttocks?"
"!"
Just as my hidden Anus and Balls were about to be revealed, I barely came to my senses and clenched my Buttocks to resist her. Then.
"You can't hide it!"
Slap-!
With a smash that seemed filled with emotion, a shock like a lightning strike shot through my Buttocks.
"Ugh-mph!"
It hurts. It hurts so much. In pain so intense it brought tears to my eyes, I writhed my body to resist. It sounds a bit ridiculous, but fear that I might actually die from this washed over me.
Can getting your Buttocks spanked hurt this much? I might really become the first person in history to be spanked to death by hand...
Whack-!
The pain inflicted on the Boy's Body, and the mind that had weakened with it. I could only tremble in fear and endure the continuing barrage of palm strikes.
And just as I'd given up on everything and squeezed my eyes shut.
Slide—
"!"
At the warm touch on my cheek, I opened my closed eyes. Silvia, who had been silently watching me writhe in pain, had cupped both my cheeks in her hands.
Then, Silvia moved her slender fingers to wipe away the tears welling in my eyes and said.
"Do not worry. I will be with you."
"..."
Although Silvia's face was nearly expressionless as she said it, her sincerity was conveyed to me. With her panties in my mouth, I quietly nodded my head...
It was only nine palm strikes, but the hellish time had passed.
"Alright~ Stop~. Everyone, please step back."
Helena made the Maids who were spanking my Buttocks move back, then said in a low voice.
"Now, only one final strike remains. I will be the one to administer it~"
She placed a hand on my bright red, heated Buttocks. Already beaten raw, my sensitive Buttocks stung and ached from the simple touch.
Helena, who had been slowly stroking my Buttocks, soon slid her finger into the crack of my ass. I clenched my Buttocks for a moment, but her finger had already invaded the space between my cheeks.
"Your Buttocks are already sensitive enough~ A lot of pain has built up, too. Shall we try converting that pain into pleasure?"
Slide—
As she said that, her finger lightly brushed past my asshole.
"!"
The moment her finger touched it, I felt a sensation of floating, and I clenched my Anus tightly. My Dick, wedged between her thighs, also twitched uncontrollably.
Helena looked at me and said.
"Huhu, it seems you have a talent for this. Pleasure and pain are two sides of the same coin. Because of the accumulated pain in your Buttocks, your Anus is also in a very sensitive state."
Suck—
Helena put the finger that had touched my asshole into her mouth and sucked on it as if it were delicious.
"It would be quite interesting to break in this cute Buttocks, but..."
"Mph-mph! Mph!"
I writhed with my whole body in resistance.
B-Buttock Training? I can do anything else, but not that. It's an act that would make me lose my pride as a man. Not that I have any pride left while getting my Buttocks spanked with my Dick wedged between her thighs, but still, I refuse!
"Well, let's do that bit by bit later. We have plenty of time. For today, I'm satisfied just seeing the potential."
Helena, who had been looking at me with a frightening gaze, soon broke into a wide smile and raised her hand to the sky.
"Anyway, I'll finish the Punishment now~."
Whoosh—
With a sound of cutting through the air, Helena's hand came down on my Buttocks. It was a palm strike faster and stronger than any that had hit my Buttocks until now.
'Fuck. I'm dead.'
I squeezed my eyes shut and tensed my whole body in preparation for the coming pain. But.
"!!!"
What struck my Buttocks was not pain, but a powerful pleasure that was hard to describe.