Her question caught me off guard. It seemed this little girl was insecure about her body. But the truth was, I found her petite frame incredibly arousing—especially now, with her school skirt gone, leaving only the white blouse.

"Silly girl," I whispered, pulling her close. "A body like yours is exactly what drives me wild. You're so sweet." My hand cupped her small breast through the thin fabric. "See? A perfect handful."

Angeline sighed, arching into my touch, but a flicker of doubt remained in her eyes. "Really, Brother? But... Mom..."

"Don't compare yourself to your mother," I interrupted. "You're both beautiful in different ways. She has her full, milky breasts, and you have this adorable, petite body in your uniform." My hand slid down to squeeze her plump bottom.

A blush spread across her cheeks, but a satisfied smile finally touched her lips. Her hesitation melted away, replaced by the certainty that she was truly desired.

"Now," I murmured. "Get ready for your reward."

Angeline nodded slowly, then moved onto the bed on all fours. Her bottom was raised, the rabbit-tail anal plug still nestled snugly between her cheeks.

The sight was intoxicating: a young girl in a neatly buttoned school blouse on top, completely naked and exposed from the waist down. My cock throbbed in anticipation.

I ran a hand over her smooth buttocks, feeling the tension in her muscles. Then, I called for Delilah.

"Mom, sit in front of Angel. Hold her and keep her calm."

Delilah crawled closer, her heavy, milk-laden breasts swaying with the movement. She cradled her youngest daughter's face against her ample bosom, her gentle hands stroking Angeline's blonde hair.

"Shhh, sweetie... Mom's here with you..." she whispered.

"Get ready, sweetheart," I said, my hand finding the base of the anal plug.

Angeline bit her trembling lip and nodded. "I'm ready, Brother."

I pulled. Pop! A soft, wet sound was followed by Angeline's long, shuddering moan. Her small rear entrance twitched, gaping slightly from being stretched all day, yet it still looked impossibly tight.

"Delilah, Gwen, watch closely," I ordered, picking up the lube. "You're about to see something special."

I poured a generous amount onto my hand, slicking my huge, aching cock, and then applied more directly to Angeline's wet, twitching hole. Looking at that tiny opening, I knew this would be painful for her. And that was precisely the point.

My index finger circled her clenched anus. "Relax, Angel. Take a deep breath for me..."

She inhaled, but her body stayed rigid. My finger began to press inward, slowly breaching the tight ring of muscle.

She gasped, her whole body stiffening as my finger slipped inside. "A-aah... I-It hurts, Brother..."

"Shhh, it's okay, sweetie," Delilah cooed, pressing her daughter's face deeper into her chest. "Mom's here... Just breathe..."

My finger slid in to the hilt, met with incredible warmth and a suffocating tightness. I massaged her internally, trying to coax her muscles to relax. After a moment, I felt a slight give.

"Good girl," I murmured, adding a second finger.

This time, her moan carried a hint of pleasure.

When I decided she was ready enough, I guided the lubricated tip of my cock to her incredibly tight entrance. The sheer size difference was almost daunting, but my lust overpowered any hesitation.

"Here we go, Angel. Breathe in... and out..."

She obeyed, and as she exhaled, I pushed the tip in.

"AAAAAAAKKKHHH!!! NO!!! IT HURTS!!! BROTHER, IT HURTS SO MUCH!!!" Her scream was piercing. Her hands flew to her mother's arms, gripping with white-knuckled force.

I stopped, only about a third of the way in. But the sensation was overwhelming. Her tightness was a painful, exquisite vise around the head of my cock.

"Sob... sob... please... please stop..." she sobbed, tears streaming down her face. "I... I can't..."

"It's okay, sweetie, it's okay," Delilah whispered, stroking her hair, her own eyes glistening. "Just bear with it, the pain will fade."

But I had no intention of stopping. With grim determination, I pushed deeper, forcing my way through the impossible tightness.

"AAAAAAAAAKKKHHH!!! MOM!!! HELP!!! IT HURTS SO MUCH!!!" Angeline screamed hysterically, her body shaking violently on the verge of collapse. Her hands clawed at her mother's skin.

From the corner of my eye, I saw Gwenneth watching, her face pale, muffled groans escaping her ball gag. Yet her pussy was dripping, soaking the ropes that bound her.

I kept pushing, slow and relentless. Every inch was a battle against an almost inhuman tightness. It was excruciating for her, and that only fed my arousal.

"PLEASE... BROTHER... I... I REALLY... CAN'T..." she cried in utter despair.

But I was in too deep. With one final, brutal thrust, I buried my entire length inside her rectum.

"AAAAAAAAKKKKKKKHHHHHHHHHH!!!!!!!!!!"

Her final scream was heart-wrenching; she was completely broken. Her body went limp, capable only of weak, shuddering sobs. I remained still for a moment, savoring the incredible sensation of her impossibly tight ass. It was so much tighter than her pussy—every tiny movement felt like she was milking me with brutal force.

I leaned down and kissed her sweaty shoulder. "It's over, Angel. The worst part is done."

A moment later, Angeline looked back over her shoulder, her face wet with tears. "Sob... Brother... that... was torture... you tore me apart..."

"Should I pull out?" I asked, feigning concern.

She shook her head slowly. "Don't... don't pull out... I... I want to feel all of it..."

I smiled, pleased. "My brave little slut."

I paused, captivated by the sight: Angeline's plump, petite bottom, and my large, hard cock buried completely within her. Her red, swollen anal hole was stretched taut around my shaft, the skin pulled to an almost impossible degree.

"Fuck... so fucking tight..." I muttered, feeling every pulse in my constrained cock.

Slowly, I began to move, pulling back slightly before pushing back in. But the tightness was so extreme that even this small motion made Angeline cry out.

"AAAAHHH! DON'T! IT HURTS!" she screamed, her tears soaking Delilah's breasts.

Delilah watched with a horrified, guilty expression, but as I expected, her eyes began to change. Lust was slowly overpowering her pity.

I could see her gaze locked on my cock moving in and out of her daughter's ass, her lips parting slightly, her hands unconsciously kneading her own breasts.

The incredible tightness brought me to the edge quickly. Within minutes, I felt the heat coiling at the base of my spine.

"I'm... almost...!" I grunted, speeding up my thrusts.

With a few final, brutal drives, I released deep into her narrow rectum. My hot cum flooded her insides, wrenching another scream from her—a long sound mixed with pain and shock.

I pulled out my throbbing cock, leaving her anal hole gaping, red, and dripping with a mixture of lube and my seed. Angeline lay collapsed, sobbing weakly.

But my cursed, insatiable libido refused to let my cock soften; it remained erect and pulsing.

After a moment's rest, admiring Angeline's bruised buttocks, I decided to go again. This time, more cruelly.

"Get ready for round two, Sis," I whispered, guiding the still-wet tip of my cock back to her wounded entrance.

"N-No, Big Bro... I can't..." she whimpered in fear.

I ignored her. With one brutal shove, I thrust back into her sensitive, torn ass.

"AAAAAKKKHHH!!! MOM!!! HELP!!!" she screamed, her body arching in agony.

I held her hips tightly and began to pound into her with a rough, irregular rhythm. Each hard thrust slammed her forward, her face mashing into her mother's breasts. The sound of our skin smacking together filled the room, punctuated by Angeline's cries.

"Bastard... you... sadist..." she cursed between sobs.

But then, something shifted. Amidst her groans of pain, another tone emerged—a hint of masked pleasure.

"Aaah... ah... that... it hurts..." she mumbled incoherently.

[Angeline's Sexual Arousal increased to 74 (+1)]

[Angeline's Sexual Arousal increased to 75 (+1)]

[...]

Those notifications had been popping up nonstop since I entered her ass, but I paid them no mind.

I smiled. I knew what was happening. "How long are you going to keep pretending, Angel? You like it, don't you? You like this pain."

Her body betrayed her. Her hips began to push back, meeting my every thrust. Her moans of agony transformed into stifled whimpers of pleasure.

"W-Weird... this... hurts... aaah... but..." she murmured, her voice taking on a new tremor.

"How does it feel, Angel?" I teased, quickening my pace. "Tell me."

"Hot... and... strange..." she moaned. Her hands, which had been clutching the sheets, now reached back to grab my buttocks. "D-Don't stop..."

"You want it slower? Or harder?" I taunted, driving into her faster.

She was silent for a moment, before finally admitting in a voice barely above a whisper. "Harder... please..."

"WHAT? I CAN'T HEAR YOU!" I barked, slapping her ass.

"HARDER! PLEASE... BIG BRO... WRECK MY ASS! TEAR MY ASS APART HARDER! PUNISH ME!" she suddenly screamed, her voice hoarse and raw with lust.

Now it was my turn to be shocked. Her transformation was drastic and instantaneous. The girl in pain was gone, replaced by a hungry, lust-driven slut.

"YES~! YES~! JUST LIKE THAT! IT HURTS! IT HURTS SO MUCH! AAHH~! BROTHER! YOUR COCK... IS RUINING ME... BUT... IT FEELS SO GOOD! HARDER! DESTROY ME!" she moaned.

Delilah and Gwenneth watched in stunned silence. Angeline's expression was completely transformed—her sweet face now twisted in deviant pleasure, her eyes tear-filled but blazing with madness, her lips parted to release a stream of increasingly vulgar moans.

"YES! RIGHT THERE! AAAAAHHH!!!" she screamed as I hit her sensitive spot. "MY ASS... IS BEING RUINED... IT FEELS SO GOOD!"

Her transformation excited me beyond measure. I grabbed her arms, pulling them back so her body arched, allowing me to penetrate even deeper.

"It hurts so much, brother! I... I don't know... what's happening... but... please don't stop!" Angeline cried out, her head thrown back. "My pussy... My pussy is dripping so much... AAHH~! It hurts but... I want more! HARDER! PLEASE~!"

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