Ash began a second round without stopping.
Their bodies were now slick with sweat, moving together in a relentless rhythm.
Each deep thrust made Daisy's tight walls spread around him, the intense friction driving up his pleasure.
He noticed she was noticeably tighter than mom had been. The thrilling difference sent a jolt of excitement through him.
Knowing he had just taken her virginity made him even more excited. He pushed himself deeper inside her, his thoughts growing wilder.
Nearby, Delia watched, also naked. Her fingers worked between her own legs as she observed him claim Daisy.
"Mmm~ ah~" she moaned softly, her voice full of desire.
Ash kept thrusting inside Daisy. The movement slowly woke her up.
At first, she just moaned, thinking it was a dream.
But then she felt the ropes. She felt the blindfold.
She realized she was tied up and someone was on top of her.
Panic exploded in her chest.
"W-What~" she gasped. "Let me go… Please…"
But the thrusts didn't stop. She tried to struggle, but the ropes were too tight.
She was completely trapped.
Tears soaked the blindfold as she cried. "Stop… please stop…"
But Ash continued, ignoring her plea.
Because Daisy Oak had woken up in the middle of it all. The initial pain was already gone.
Now, her body was fully awake. Every nerve was alive with overwhelming pleasure.
Each deep thrust pulled another moan from her. Pleasure and fear twisted together inside her.
"Who… is it ahhh~~~" she cried out. "Please…mmm~ let me go…ahh~~"
She tried to remember how she had ended up here, but her thoughts shattered every time his cockhead slammed against her cervix.
Daisy could no longer hold back.
"Ahhhhhhhhhhhhhhhhh~ I'm… I'm cumming~ ahhhhhh~" she cried out loudly.
Feeling her climax once again, Ash growled. "Haa~ So good and warm… your pussy is sucking me in, Diasy…" he groaned, thrusting even faster.
From his voice, she realized it was Ash.
But the only sound that escaped her lips was a string of deep, helpless moans. "Mmm~ ah~ ah~"
After more than a dozen deep thrusts, Ash couldn't hold back any longer.
"Daisy... I'm cumming~" he groaned, his fingers gripping her hips tightly as he released another thick, hot load deep inside her.
Daisy's cry was a mix of protest and overwhelming sensation. "No…! Not inside Ash… ahhhhhhhhhhhh~"
When he was finally done and thought of taking a rest, Daisy's voice came, soft and broken from crying.
"Ash… I know it's you…" she whispered, her voice trembling. "Please… just let me go… I won't tell anyone… I promise…"
Ash heard her pleas and went closer.
He knew Daisy was a warm-hearted and kind woman, unlike her sister. She also had a much better personality and always took care of Pokémon.
But he couldn't let her go, not until the mission was complete.
He moved closer to her and removed the white panty from her eyes, revealing her tear-full face.
Seeing Ash, Daisy began to cry. "Why are you doing this?" she asked.
"I always thought of you as my little brother…"
Ash sighed. "I have my reasons," he said.
"I need to have sex with you four more times. After that… I'll explain everything. I promise."
He looked at her crying face. "Then it will be up to you. Whether you understand… or not."
After saying this, he blocked her mouth with her underwear.
Daisy tried to protest. She wanted to ask what he meant… But her words were blocked by a sudden, deep thrust.
"Mmmm~" was all that escaped her lips.
Then Ash stretched. "Time to get back to work," he muttered.
After one more round, Ash was completely out of stamina.
He fell asleep like a baby, resting while sucking on Delia's breast.
"Mmm Mom… your nipples are so soft and good," Ash mumbled drowsily. "I wish they could make milk…"
As he drifted off to sleep. Delia simply smiled. The only way for that to happen would be to have another child, but Ash had already said "not now." They had to go on their adventure first and he had no plans to leave her, or any of his women behind.
This thought just made Delia's smile widen. Ah, Ash… you are such a kind boy.
Daisy Oak still remained tied up on the bed, her body trembling and broken.
She had endured three brutal rounds of sex with Ash. Her body ached everywhere, and she could still feel a dull sensation of his semen between her legs.
Daisy looked over at Delia, who was cradling Ash's head as he slept and sucked her breast.
The sight still shocked her. Even though she knew Delia was involved, seeing the mother participate so willingly was deeply unsettling.
Delia noticed Daisy looking. She spoke softly.
"I know you don't understand right now and must be very confused… but you will soon."
She pointed to the strange mark below her belly button.
"Once you are branded with this," Delia explained, "you will become just like me."
She gave a small, knowing smile.
"And don't worry. After three more rounds, Ash will finally release you."
With that, she closed her eyes, leaving Daisy alone with her thoughts.
Daisy could only lie there, completely broken and confused, waiting for whatever would happen next.
She couldn't even speak. All she could do was cry silently until exhaustion finally pulled her into a troubled sleep.
Several hours later, Ash finally woke up.
He released Delia's nipple from his mouth with a soft, wet sound.
What a great night, he thought.
He looked over at Daisy. Her eyes were swollen from all the crying and she was finally sleeping.
Ash sighed. "Well, three more rounds to go," he muttered to himself.
He wanted to finish this quickly and make sure Daisy joined them.
He also removed her underwear, hoping it would let her fully enjoy it.
He had heard from mom in the past that women get more excited when they're allowed to moan freely.
"Let's hope she enjoys it," he thought.
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.