The Academy’s Weakest Became A Demon-Limited Hunter
Chapter 353: Side Story — Dorothy's Case (3)

“You’re quite bold, President…!”

Dorothy chuckled quietly.

With every step I took, my penis swelled as if it would burst, irritating me, but I ignored it and walked briskly forward.

I gently laid Dorothy on the white bed sheets and removed her remaining panties.

“Hmm…!”

Before her vagina could be exposed, Dorothy immediately closed her legs, seemingly embarrassed.

Cute.

Without forcing myself to look at her vagina, I slowly climbed on top of Dorothy.

My shadow fell over her.

Strands of light purple hair, damp with sweat, clung to Dorothy’s cheek.

With her flushed face, she gazed at me intently, as if longing for me.

Her round and soft breasts spread outwards, taking on a captivating shape.

My gaze moved from her massive, almost violent breasts to her slender waist, wide hips, vagina opening glistening with fluid, and her beautifully sculpted legs.

Her fair and smooth body.

Wow…

For a moment, I lost myself.

Dorothy’s naked body…

How beautiful she was.

“So beautiful, it’s driving me crazy…”

Such a beautiful person was mine.

A deep sense of happiness welled up in my chest.

So much that I couldn’t suppress my smile.

“Come to think of it, President, you’ve always had naughty thoughts when looking at Big Sis, haven’t you?” Dorothy asked with a mischievous smile, half-opening her eyes.

I nodded.

It was a fact that didn’t need to be hidden.

“I wanted to do this until I’ve had my fill.”

“Nihihi, isn’t that a bit too honest?”

“Your body is just too seductive.”

“Mmm… I’m happy. Come here. You can do whatever you want with my body…” Dorothy whispered seductively as she caressed my cheeks with both hands.

“Are you not scared anymore?”

“What are you talking about? I’ve been calm from the beginning.”

A small laugh escaped.

While kissing Dorothy again, I used my free hand to remove my pants, exposing my lower body.

My penis finally greeted the fresh air.

It stood firm in front of Dorothy.

“Huuu… haah…”

Dorothy pulled her lips away from mine. Our mixed saliva, dripping down the corner of her mouth like mucus.

Dorothy lifted her head and carefully observed my male genitalia.

“Isaac…”

Dorothy swallowed dryly, her face tense.

“Big Sis won’t die, will she…?”

She trembled intermittently.

Did she suddenly get scared?

I lifted my upper body and gently stroked Dorothy’s thigh.

The smooth texture of her skin was noticeable.

“It’s okay. Spread your legs.”

“…Okay.”

At my quiet words, Dorothy blushed again and slowly spread her legs.

A small amount of light purple pubic hair.

Below it, a pink, slit-shaped line hidden between her pale skin came into view.

The area was daintily closed, steadily oozing a slippery fluid.

This is… Dorothy’s vagina.

“If you keep staring like that, Big Sis will be really embarrassed…”

Dorothy’s voice trembled slightly.

Feeling my gaze between her legs, her face turned even redder.

“You’re truly beautiful.”

“Don’t say things like that…” Dorothy covered her eyes with her arms and muttered in a whiny tone.

She seemed very embarrassed.

I leaned my upper body closer to Dorothy again.

My fully erect penis pressed against Dorothy’s vagina opening.

Little by little, I rubbed myself against it.

“Huh-ahh…!”

Suddenly, Dorothy arched her back visibly startled.

Immediately, I stopped the movement of my hips.

“Ah, Isaac…”

“What’s wrong?”

“Ah, no, you see… Should I say the sensation is a bit intense? Or maybe… should I say it feels so good it’s almost dangerous…? Isn’t this a little risky? Ah, n-not that it’s anything serious, you know…!”

The friction against her clitoris must have been intense.

In an effort to reassure her, I offered a quiet smile and gently stroked Dorothy’s hair.

Dorothy took a deep breath and then smiled softly, saying, “No, it’s okay…”

I shifted my hips again, sliding my penis over her vagina as if warming up.

“Huh-ah…! Uh, ugh…!”

Dorothy tightly closed her eyes and bit her lip. She turned her head to the side and let out deep breaths, her face flushed red.

Squish, squish…

Dorothy’s fluids and the precum from my penis mixed together, creating an erotic, harmonious sound, like a chord.

Unintentionally, I let out a small grunt as the pleasure was overwhelming.

“Haah, haah…”

Dorothy’s breathing soon began to slow down.

Gradually, she seemed to get accustomed to the sensations.

“Huh, ugh… Isaac… It’s okay… You don’t need to hold back so much…”

Dorothy looked at me with her flushed face.

It was hard to believe it was the same face that usually carried such mischief.

A somewhat pitiful expression, entirely drenched in lust… the face of a female lost in desire.

My breathing grew heavier from the overwhelming excitement.

Soon, Dorothy’s moaning voice resonated in the air.

“Put it in…”

That sticky, lingering plea shattered the last bit of self-control I thought I had.

I firmly intertwined my fingers with Dorothy’s.

The head of my penis slid between her fluid-covered legs, softly touching her labia.

It was soaked with her warm fluids, feeling incredibly silky.

The head slipped gently between her labia and entered her vaginal opening, as I slowly pushed my hips forward.

“Ahhh…! It’s too big…!”

Dorothy arched her back dramatically, clenching her teeth to stifle her cries.

Her narrow, tight vagina gripped my penis snugly, persistently sucking it in.

Her insides stretched gradually to accommodate my size.

With a smooth motion, something inside her vaginal walls was pushed aside by the insertion of my penis, and Dorothy tightly shut her eyes.

“Ahhh, ah…!”

Dorothy furrowed her brows deeply.

A strained cry of pain escaped her lips, and red blood slowly trickled from where we were joined.

It was the moment my penis was halfway in.

My self-control immediately kicked in, and I stopped the penetration.

“Are you okay?”

“Ah, ah… it hurts…!” Dorothy complained of her pain in a hoarse voice.

I stroked her hair gently, giving her time to calm down.

“Haah, haah…!”

Dorothy panted as she looked at me.

Her eyes were wet with tears.

“I’m sorry, Isaac… It’s just a little more than I thought, um…”

“I’ll wait until you get used to it.”

“Yeah, thank you.”

I kissed Dorothy on the cheek, and she leaned in to continue kissing me.

Smooch, kiss, slurp….

Eventually, she pulled away and said, “…I’m okay now, you can move.”

It was a gentle whisper.

“Don’t overdo it.”

“Overdo it? I said I’m fine. I’m comfortable.”

Was it the ample fluids easing the pain, or was she forcing herself to endure it?

I wasn’t sure, but I moved carefully so as not to hurt Dorothy.

“Okay.”

I smiled and moved my hips slowly. My penis was still only halfway in.

“Hngh, huff, haah…”

Dorothy let out a heated moan.

Her vaginal walls warmly and tightly enveloped my penis for the first time.

The pressure, warmth, and softness were absolutely enchanting.

Dorothy let out a soft, suggestive laugh accompanied by her breathing.

“I feel fine now… it’s really no big deal, is it…?”

“Does it feel better now?”

“I’m okay… ugh… it doesn’t hurt anymore, it actually feels good now… Isaac, you’ve finally become one with Big Sis. Isn’t it an honor?”

“Yeah, I’m honored.”

“Nihihi… huff… does it feel good inside Big Sis?”

“It feels amazing.”

“That’s a relief…”

“…?”

Then, seeing Dorothy’s eyes, my heart sank.

I immediately stopped moving my hips.

“…Why did you stop all of a sudden?”

“Why are you crying?”

“Huh? Oh.”

Tears were streaming down Dorothy’s cheeks endlessly.

“What’s it? What’s going on?”

“Does it hurt that much? Should we stop for a bit?”

“No, it doesn’t hurt anymore…”

Dorothy seemed flustered by the tears that wouldn’t stop flowing.

Dorothy kept wiping her tears and smiled awkwardly.

“Actually… you know?”

“Yeah?”

“I’m really happy right now. Being with you… should I say it makes my heart feel a little overwhelmed? Nihihi, such a corny thing to say… You can ignore it if you want.”

Feeling a surge of ecstasy, I brushed Dorothy’s hair and gave her a light kiss.

Suddenly, the journey we had taken together came to mind.

The three years we spent enrolled in the academy.

It was a time that could feel short or long, but so much happened during it.

Suddenly, I remembered the time we brought down the Floating Island and fell together, her face shining with an unusually bright smile.

Dorothy, who said we should destroy the world together, and Dorothy, who endured loneliness for my sake.

All of these memories flashed through my mind.

— Are the two of you in love with each other right now?

That question still gnawed at my heart.

A flood of emotions surged up my spine.

All those emotions culminated in a single whisper, “I love you, Dorothy.”

I had never once doubted this feeling.

I liked Dorothy, and as time went on, my feelings for her only grew stronger.

Dorothy’s tear-filled eyes widened greatly.

She regained her composure and displayed a smile filled with mixed emotions.

“Big Sis loves you too. Forever.”

At last, we had reached this point and were reaping its rewards.

I would continue to love Dorothy endlessly, and we would be happy forever.

Smooch.

I gave her a light kiss and looked at Dorothy before playfully starting to speak.

“Come to think of it… you said you were feeling relaxed, right?”

“Yeah?”

“Actually, I’ve only put in half.”

“What? O-only half…?”

Dorothy was startled.

As I slowly thrust my penis deeper, she let out a moan that bordered on a scream, “Huh, ah…!”

Dorothy tightly closed her eyes and lips, holding her breath to stifle her cries. Though a muffled sound, “Mmph…!” escaped, her back gradually arched higher and higher.

A crashing wave of pleasure overwhelmed my mind, but I barely managed to hold onto reason and stopped my hips when my penis was about two-thirds in.

If I went any further, Dorothy seemed like she might truly faint.

“Haah, haah…!”

Dorothy finally opened her eyes, panting with her mouth wide open. Her big, luscious breasts bounced up and down with each ragged breath.

Dorothy’s vagina walls pulsed as they gripped my penis tightly.

I moved slowly.

I clearly felt the shape inside her and savored it.

“Ugh, uh, haaah…! Haah…!”

Caught between pleasure and pain, Dorothy let out moans that sounded like sobs, clutching my interlocked hands even more tightly.

Squish, squish…

The erotic, squelching sound of friction echoed rhythmically due to the overflowing fluids.

“Ugh, ugh, ahh, this… feels good…!”

Dorothy’s moans of pleasure made my hips move faster without realizing it.

Dorothy twisted her body wildly, letting out continuous sensual moans.

The thought of Dorothy, whom I loved so much, feeling this way because of me filled me with overwhelming ecstasy.

“Ah, wait… Big Sis is in danger…! She can’t think straight…! Ugh, something strange is building up, I feel like I’m going to cum…!”

“I think I’m about to cum too…”

My penis throbbed violently as the overwhelming urge to cum surged through me.

I wanted to make my first time with Dorothy last longer, but her vagina walls clenched tightly around my shaft, urging me to cum, and it was almost impossible to hold back.

“Ugh…!”

It felt like I was going to explode.

…Still, shouldn’t it be fine now?

After all, I wanted to get Dorothy pregnant with my seed.

In that case, there was no reason to hold back at all.

I moved my hips faster while being careful not to fully enter her.

Squelch, squelch!

The sound echoed repeatedly from where we were joined.

“Haah, haang…! Isaac, cum for me…! Haah, Big Sis is almost…! Hah!”

Overwhelmed by the maddening urge to release, I thrust my hips forward.

My penis plunged deep into Dorothy’s soft inner flesh.

The head of my penis forced its way through the tight, warm passage, pressing into the deep mucous membrane before it burst, I came explosively.

Dorothy’s eyes widened in shock, but before a scream could escape, I sealed her mouth with my lips.

“Mmmph…!!”

Dorothy screamed into our joined lips. With her body pinned down and our hands interlocked, she couldn’t resist at all.

Dorothy’s vagina walls pulsed rhythmically, squeezing my penis buried to the root, as if desperate to take in every drop.

Throb, throb.

Viscous and densely concentrated cum erupted without pause, soaking the tip of the penis in its sticky sensation.

A wave of intense pleasure shot through my entire body like lightning. I trembled intermittently.

Dorothy’s body trembled, and the shiver passed through her lips, reaching mine.

It was a shared climax.

For a while, I stayed still in that state. I wanted to fully savor the current ecstasy.

Immersed in the lingering sensation of pleasure for a while, I carefully extended my tongue.

As if waiting for it, Dorothy’s tongue came to meet mine, intertwining and sharing saliva again.

“Haah…”

I unclasped our interlocked hands and lifted my head.

Dorothy took deep breaths and glared at me intensely.

She seemed annoyed.

“Big Sis almost died just now…”

“I’m sorry. I got carried away because it felt so good…”

“I’m not blaming you. It’s all in now, right?”

“Yeah, it’s all in.”

Dorothy, who had been glaring at me, smirked faintly as if it had been a joke and steadied her breathing.

“I’m happy… It finally feels like I’m truly one with you.”

“Does it hurt?”

“It hurt a lot for a moment, but now it’s bearable… I almost fainted though.”

Dorothy stroked the side of my head and gave a sly smile.

“Your cum is swirling inside me? You really wanted to get me pregnant that badly, huh…?”

Ah…

I can’t hold it in anymore.

“Ugh…! W-wait, don’t move right now…! Haaah…!”

The heightened sensitivity following cumming tightly gripped my penis. Even the slightest movement of my hips brought such overwhelming pleasure that it bordered on being unbearable.

Dorothy seemed to feel the same.

And yet… my penis remained rigid inside Dorothy’s vagina. My lust had not yet subsided.

I realized that the hurdle for reaching post nut clarity had significantly risen.

“It’s not over yet.”

“Huuuugh…!”

When I withdrew my waist, Dorothy tightly closed her eyes and reacted strongly.

When I pushed forward again, she let out an enticing moan.

“Haaah…!!”

Along with her vaginal fluids, pale cum trickled down from Dorothy’s vagina.

“P-painful…! It feels so good, I think I’m going to die…! What is this feeling?!”

“You’ll get used to it soon…!”

The intense and sensitive sensation that followed the climax.

The pleasure was so overwhelming that it made my head spin, but I wanted to endlessly enjoy even that sensation.

Squelch, squelch…!

With each movement of my hips, the sensual fluids created friction, producing a sticky, squelching sound.

With the addition of cum, the thrusting motion became even smoother.

“Hnn, haah…!”

Perhaps because she had grown accustomed to the pleasure, Dorothy’s sweet moans gradually took on a flirtatious tone.

She stretched her arms back, revealing her smooth underarms as she tightly gripped the pillow.

“This is so good…! Big Sis thinks she’s going to come again…!”

Her beautiful eyes, brimming with tears, looked at me.

How could she be so lovable?

I wrapped my arms around Dorothy’s waist, lifted her, and braced my lower body before thrusting my hips forcefully.

Squish, squish!

Erotic sounds of friction.

And the sound of rain harmonized with Dorothy’s moans.

“Uh, aah…!”

Dorothy arched her waist upward, her body trembling uncontrollably.

I paused my hips for a moment and watched Dorothy, who had just experienced her second orgasm.

“Haah, haah… I’ve never felt this good before… Did Big Sis look a little embarrassing just now…?”

“Not at all. You’re just beautiful and lovely.”

“Nihihi… Really? You’re cool too…”

Dorothy formed a soft smile and placed her hand on her stomach.

“My belly feels so full… Phew, it looks like I might get pregnant today…”

“Shall we think of baby names while traveling?”

“That sounds fun… huugh! Wait, I’m still sensitive…! Haaah…!”

When I started moving my hips again, Dorothy let out a moan.

Finally, as the urge to cum for the second time arrived, I tightly grabbed Dorothy’s breasts with both hands and released my cum.

Throb! Throb!

In a soaring wave of liberation, as if my entire body were floating into the sky, I closed my eyes.

I pressed my hips firmly, wanting to pour even the last drop deep inside Dorothy.

“Hngh…! Isaac, it’s so hot inside…! Haah?!”

Squelch! Squelch!

Even as I cummed, my thrusting never ceased.

Cum leaked out through the gaps of our union.

“Hngh, aah…! Already, you’re moving again…?!”

“I can’t stop…!”

Even though I’ve already cummed, why is my sexual desire surging even stronger?

I didn’t know why. It felt as if I had turned into a beast, moving solely for reproduction without hesitation.

I roughly thrust into Dorothy’s pussy again, plowing through her depths.

Bang! Bang! Bang!

The sound of skin clashing echoed. It was hard to stop my hips.

A fierce, lust-soaked sex carried on, solely in the pursuit of pleasure.

I didn’t know where the freshness of the first experience had gone, but I didn’t feel any particular hesitation.

Faced with the suppressed desire for Dorothy that had been building up… it seemed I had no control.

“Haah! Hngh, ah, ahng…! Isaac, just a little slower…! Haaang!”

Despite Dorothy’s pleas, I couldn’t allow myself to rest.

Third time, a fourth time, a fifth time… I lost count as I kept cumming inside her vagina.

Driven by the desire to pour every last drop of cum into her womb.

At some point, we abruptly stopped speaking. All we did was sweat heavily and indulge in each other’s bodies.

No matter how I shifted positions, Dorothy wordlessly took it all, consumed by her craving for pleasure.

Every time I briefly pulled my penis out, cum gushed out like a waterfall.

I wasn’t sure how much time had passed.

I switched back to the missionary position and looked at Dorothy.

“Haah, ack…! Ugh, hngh, ehh…!”

Dorothy let out intense moans.

Dorothy’s eyes had been unfocused for quite some time.

Saliva dripped from the tip of her tongue that she stuck out.

Her face showed that she could think of nothing but sex with me.

Her face, as if urging me to unleash my sexual desire onto her body as much as I wanted, made it even harder for me to stop.

Bang! Bang! Bang! Bang!

As I slammed my penis roughly into Dorothy’s vagina, the urge to cum swelled to its limit once again.

The final moment.

Grasping Dorothy’s plump breasts with both hands, I drove my shaft deep into her inner walls. A torrent of pleasure surged through me as writhing fluid in my scrotum shot up through my urethra.

I released it without restraint into Dorothy’s insides.

Throb, throb!

“Huuuuuh…!”

Dorothy moaned, sticking out her tongue.

The lust still boiling inside me was unrelenting, and my penis showed no sign of shrinking.

“Feels good, Your Highness…”

Is she saying she felt good?

I brought my tongue to meet Dorothy’s extended tongue. Instinctively, she moved her tongue in circles, intertwining it with mine.

After so much kissing, with saliva mixed several times, my mouth quickly dried up.

After repeating dry, moistureless deep kisses, Dorothy pulled her lips away and let out a languid voice.

“I’m thirsty…”

Dorothy used starlight magic to bring a water bottle, drank from it, and handed it to me.

“Ah.”

She looked exhausted.

Suddenly, reason resurfaced, and guilt arose.

Did I overdo it?

I turned my head to look out the window. Before I knew it, the night had passed, and dawn was breaking.

“How long did it go on?”

How many hours had we been frantically having sex? It was hard to tell.

It was natural for Dorothy to be exhausted.

I should let her rest now.

“Hnng…!”

As I slowly withdrew my penis from Dorothy’s vagina, a sensual moan escaped her lips.

It was hard to tell whether it was vagina fluids or cum as a copious amount of thick cum sloshed and trickled steadily from Dorothy’s vagina.

Perhaps due to the lingering effects of countless climaxes, Dorothy’s body trembled slightly.

“Hnn, haaah… Isaac, is it over now…?”

Dorothy looked at me with weakened eyes and asked in a whisper.

Her sweat-soaked, light purple hair and both arms hung limply.

“Big Sis can’t think about anything anymore… My head feels so hazy…”

Dorothy dragged her words.

She was really tired.

This was her first experience… Did I lack consideration?

Maybe I pushed her too hard.

I felt very sorry.

I hadn’t expected to lose control of my desire this much.

And yet…

It still hasn’t subsided.

My penis, smeared with cum and fluids, was still firm and swollen.

I had already noticed that my stamina had improved thanks to [Physical Training Efficiency], but I didn’t expect it to be so uncontrollable at this level.

Well, having risen from the weakest to the level of a demigod… it wasn’t strange.

It’s not like I have infinite stamina or something…

Will my stamina ever run out?

At this rate, satisfying all my desires seemed like too much for just one wife to handle.

“Isaac… you still haven’t calmed down, have you…?” Dorothy whispered softly in a daze.

Is she feeling guilty?

“No, it’s fine. I enjoyed it, a lot.”

Still, that much was enough.

I had released enough of my desire. Now, I could exert self-control.

My penis, immersed in the afterglow of its thrusts through Dorothy’s vagina, showed no sign of softening, though it would eventually calm down on its own.

As I laid on the bed, Dorothy turned her body toward me.

Gently, I brushed Dorothy’s hair with care.

“Are you okay? Does it still hurt?”

“Honestly, it hurts… I’m not sure if I’ll be able to walk today… Or, should we stay here for another night?”

“I wouldn’t mind.”

“Nihihi, cutie…. Come here, into Big Sis’ arms.”

I moved and nestled into Dorothy’s arms.

Our sweat-soaked skin touched, but it didn’t feel uncomfortable at all.

Rather, the strong odor only lifted my mood.

“Huh?”

Dorothy grabbed my still-rigid penis and wedged it between her vagina and thighs.

The erotic liquid caused a strange, tsch slurping sound.

Her slippery, fluid-covered labia wrapped tightly around my penis, and the warm, wet sensation was intensely satisfying.

“How is it?”

“It feels good.”

“That’s a relief.”

Dorothy smiled with satisfaction.

…This isn’t bad either.

“Let’s rest for a bit like this, and then do it again?” Dorothy whispered intimately into my ear; her tone alluring.

Somehow… I felt like Dorothy had become even more erotic.

“Do you think you can rest?”

“Even if I can’t rest, it can’t be helped… It feels so good.”

I tightly hugged Dorothy, who was softly laughing.

“Isaac.”

“Yes.”

“I really love you.”

“I love you too.”

Eventually, Dorothy seemed to fall asleep, her eyes closed as she let out calm breaths.

I, too, fell asleep holding her.

Perhaps because having sex with Dorothy felt so good, I dreamed of being with her intimately once again.

And not long after, I woke up while cumming.

Throb!

“Ugh…!”

As soon as I snapped my eyes open, I felt a chilling wave of pleasure as my penis was being sucked.

When I lifted my head, I saw Dorothy with my penis in her mouth, sucking wetly with repeated smacking sounds.

The room was bathed in sunlight. Dorothy pulled her mouth away from my dick and gulped down the cum.

“Ugh, bitter…”

Dorothy frowned for a moment, then looked at me and smiled brightly.

“Did you sleep well? Sorry, I didn’t mean to wake you.”

“Dorothy, just now…?”

“I thought this would make you feel good in your dreams. Your expression while sleeping was really funny.”

…Once again, I realized anew.

I truly was a successful fan.

“…Shall we go wash up?”

“Hyaa?!”

I stood up abruptly, carried Dorothy, and headed to the shower.

“Aah, haaah…!”

While washing up, I ended up pouncing on her again.

Today was the second day of our trip.

We still had two more weeks left on our trip.