Ash after some morning routine roughly began another round, jolting the exhausted Daisy awake.
The sudden stimulation quickly built into an overwhelming wave, forcing another climax from her exhausted body.
"Ah~" she cried out, her will crumbling. "My pussy~"
Delia joined in too, one hand pleasuring Daisy's breasts while the other rested on Ash's shoulder, kissing him deeply and making Daisy moan even louder.
"Ah~ My nipples… my pussy… ah~ It feels so strange… so good… ah~"
She had climaxed twice in this round alone.
Daisy was finally losing her spirit against the pleasure, her resistance slowly melting away.
Ash groaned as he released a thick load of milky white semen inside her.
Thanks to his earlier rest, his potency had renewed the warm fluid flooding her and was noticeably heavier and richer than before.
After finishing the fourth round inside her, he looked down at her dripping pussy.
"Two more rounds left. But sorry, this next one is going to be in your anal."
Hearing this, Daisy's body trembled violently.
"No… you can't… you can't do it there…" she pleaded, her voice rough.
"That's not… a good place…"
Ash just smiled, giving her ass a sharp slap.
"Don't worry… I'll be gentle."
"Please, Ash… listen… you can't do it there…" Daisy pleaded, her voice trembling.
Ash gripped her hips, spreading her cheeks wide.
"It looks a bit dry and tight back here," he muttered.
"Let's see if this works. To be honest Daisy, this is my first time trying anal. Last time I did it… I don't even remember how it went. Let's hope you enjoy it."
With that, he pushed into her. Her back passage was incredibly tight, resisting him at first.
But when it finally gripped him, the sensation was overwhelming.
"Ah~" Daisy screamed, her body jolting from the sharp pain.
"Take it out~ It hurts so much~" she cried.
"Ah~ So tight," Ash groaned, struggling to push deeper. "Damn… how did I do this last time?"
He looked toward Delia, his expression a mix of strain and confusion.
Delia simply shook her head. "Don't ask me," she replied, turning to leave the room.
"Well, I'll prepare something to eat for you two. Continue," she said before closing the door behind her.
Ash's gaze fell upon her tight little anus.
"Let's see if this works," he muttered to himself.
He coated his finger with his saliva, then pressed the moist finger firmly against her tight entrance.
He pushed slowly, feeling her incredible tightness.
"Ah~" Daisy Oak moaned loudly in pain. "It hurts… stop, Ash, I beg you~"
But Ash didn't care. The fun had just started.
He pushed until his finger was completely inside, then slowly began to move it back and forth.
After a minute of this, he added a second finger, stretching her further.
"Ah~ No~" she cried out, her voice strained.
But as he continued the slow, persistent rhythm, the sharp pain began to mix with a strange, unwanted pleasure.
Seeing her react, Ash smiled.
He decided to try something special.
He formed his right hand into the "kancho" gesture, pressing his index and middle fingers together tightly.
With a sudden, deliberate push, he thrust them into her tight hole, aiming deep in a sharp, stabbing motion.
"KYAAAA~" Daisy screamed, her body jolting violently from the shocking, invasive pain.
"Stop! It's too deep~"
But Ash was amused. He began repeating the motion, a series of short, sharp thrusts that made her gasp and cry out each time.
The initial shock was overwhelming, but as he continued, the sharp sensation began to spread through her, a strange mix of pain and intense stimulation that left her trembling and confused.
He continued this for a full ten minutes.
Daisy's screams slowly turned into moans.
"Ah~ Just like that~" she finally gasped, her body betraying her.
"It's starting to feel good~ Ash, don't stop~ haaa~~"
Ash found a new excitement in this. He continued for a while longer until Daisy's body could no longer hold back.
"Ah~ I'm coming~ ahhhhhhhhhhh…" she cried out as she climaxed, her body trembling before she panted heavily.
Afterwards, Ash looked at her stretched hole.
"I did work hard," he said, rubbing the sweat from his own forehead.
Next, he positioned his cock at her entrance.
This time, it slid in more easily, but deeper inside, she was still incredibly tight.
"Damn, Daisy... why are you still so tight?" Ash grunted.
He thrust forcefully back and forth, driving his cock deeper with each movement.
After a dozen hard thrusts, he was fully inside. Her walls gripped him tightly, but it felt completely different from her pussy.
It was a tighter, hotter wall of pressure that seemed to cling to his entire length, creating a smooth, unyielding friction that was less wet and more intense.
There was no natural slickness, just the raw, tight heat that made every movement feel incredibly sharp and direct.
Daisy could only moan nonstop. "Ah~ ah~ ah~ My ass… my ass can feel your hot cock… keep going~ ahhh~"
She was already lost to the pleasure.
Who knew the thing she had feared most would give her this unique feeling she had never experienced before.
Ash continued and soon flooded her ass with his seed and made her cum again.
"Aagoo~ ah~ So good… so hot~" she cried as the intense feeling slowly subsided.
He pulled out with a wet pop, a trickle of white leaking from her hole.
Without pause, he pushed back in for the final round.
Daisy begged louder this time, "Deeper, Ash, fill my ass~ it feels so good~"
Her body shuddered through another orgasm as he pumped the last load deep inside her hole.
The system ping and the slave mark appeared above her pussy
Daisy's eyes glazed with submissive bliss.
"Daisy, why are you trembling so much?" Professor Oak asked.