Chapter 100: Chapter 100 – The Heart-Tipped Cruelty

My gaze fell to the collection of toys on the floor, and I picked up the anal plug. Crafted from black silicone, it was intimidatingly large—perhaps the width of my two thumbs combined—yet topped with a deceptively cute, heart-shaped end. Using the residual wetness glistening on Delilah’s thighs as lubricant, I pressed on.

“Don’t worry, Mom,” I whispered, my index finger already circling her twitching rear entrance. “This is just a tool. A whore like you should be accustomed to having all her holes filled.”

Delilah, even with her mind shattered and fully enslaved, could still feel a primitive instinct of fear. Her eyes widened at the sight of the plug’s size, her body instinctively tensing.

“A-Adam… that’s… too big…” she whimpered, the small, fearful voice only fueling my arousal. “Please… don’t… I promise to serve you better… with my mouth… with my hands…”

I gave her buttock a gentle slap. “Relax, Mom. I know what’s best for you.” My hand pressed the tip of the plug slowly against her tight hole. “Take a deep breath… and push it out…”

Delilah drew a sharp breath, her chest rising. As she exhaled, with one quick, firm thrust, I pushed the plug all the way in.

“AAAAHHHH!!!” An ear-splitting shriek of pain tore from her lips. Her body arched, trying to escape the sudden, burning sensation filling her backside. Her tight anus was forced to stretch brutally to accommodate the foreign object.

“There, there,” I whispered soothingly, my hand stroking her sweaty back. “The worst part is over. I did it all at once on purpose; going slow is more torturous. Trust my experience.”

Delilah sobbed, her face buried against Angeline’s thighs. “But… but it hurts so much, Adam…”

“I know, Mom. But as my good whore, you have to accept anything I give you, right?” I teased while slowly twisting the plug inside her, making her moan with a mix of pain and strange sensation. “And don’t worry, I won’t be using your ass today. This is just training. To get you accustomed.”

She gave a weak nod, tears streaming down her cheeks. “Yes… Mom… Mom will accept everything…”

Satisfied with her response, I then positioned my cock, slick with Angeline’s saliva. Without further ceremony, I placed the tip against Delilah’s pussy and thrust in all the way.

“NNNNGGGHHH!!!” Delilah screamed again, this time with a different tone.

The sensation she felt now was utterly bizarre. Her pussy, already sensitive from multiple orgasms, was now completely filled by my cock, while next door, in her ass, the large anal plug provided constant internal pressure.

It felt… incredibly full. As if every inch of her womanly passage was being stretched, filled, and dominated.

For me, the sensation was incredible. Delilah’s pussy felt tighter than ever—likely from the pressure of the anal plug pushing against the wall between her pussy and rectum. Every thrust of mine met a delightful resistance, as if her body was trying to reject me while simultaneously pulling me deeper. I couldn’t stop, the rhythm of my hips growing faster.

PLAP! PLAP! PLAP! PLAP!

The wet, loud sound of our bodies colliding filled the room. Delilah’s plump, reddened buttocks, marked by my slaps, jiggled violently with each thrust, creating mesmerizing little waves. I gripped her hips tightly, slamming her harder against me.

“Angel,” I called out to the girl still lying beneath us, her eyes shining as she watched her mother being treated roughly. “Suck your mother’s clit. Make her feel even more pleasure.”

Obediently, Angeline leaned in and without hesitation placed her mouth on her mother’s swollen clitoris. Her small, skilled tongue immediately went to work, licking and sucking enthusiastically.

“Ahh~! Angel! No… not there…!” Delilah tried to protest, but her voice was muffled by Angeline’s pussy, which she was still licking on my previous command.

“Now, Mom,” I ordered, continuing to pound into her mercilessly. “Keep licking your daughter’s pussy. Make her feel good too.”

With a forced moan, Delilah lowered her head back between Angeline’s thighs. Her tongue began working on her youngest daughter’s clitoris, making Angeline let out small, pleasurable whimpers.

The sight was truly spectacular. Mother and daughter giving each other oral pleasure while I fucked the mother from behind. Delilah’s pussy grew tighter and began pulsating wildly, clenching around my cock as if unwilling to let go.

“Adam! I’m… I’m going to… AAAAAHHH!!!” Delilah suddenly screamed hysterically, her body shaking uncontrollably.

She climaxed again, her pussy squeezing my cock powerfully while her mouth continued working on Angeline’s pussy, sending her youngest daughter over the edge into orgasm as well.

But I was far from done. I pulled my cock from Delilah’s pulsating pussy, making her groan at the loss.

“Angel, open your mouth wide,” I commanded.

With flushed cheeks and teary eyes from pleasure, Angeline obediently opened her mouth. Without waiting, I thrust my cock, wet with her mother’s juices, into her small mouth.

“GGLKK…!” Angeline gagged, her eyes bulging. But strangely, she didn’t fight it. Instead, her hands grabbed my buttocks and pushed her head deeper.

The notification in my vision showed she was enjoying it:

[Angeline’s Sexual Arousal increased to 67 (+3)]

[… ]

“You little pervert,” I muttered.

Angeline truly enjoyed being treated roughly like this. She even locked her mother’s head in place with her thighs, forcing Delilah to continue licking her sensitive, post-orgasmic cunt.

As I fucked Angeline’s mouth brutally, my hands grabbed Delilah’s large, swaying breasts. I squeezed and twisted her already hard nipples, making her moan with a mix of pain and pleasure.

From the corner of my eye, I saw Gwenneth, still bound. Her face was pale, her eyes empty, but something had changed about her body. Her pussy was soaking wet, dampening the ropes that bound her.

Her body swayed weakly, as if dancing to the rhythm of my thrusts. She had been on the edge of climax multiple times, but [The Edge of Bliss] around her neck kept her teetering on the brink.

Now it was time for the finishing touch.

I pulled my cock from Angeline’s mouth and plunged it back into Delilah’s still-sensitive pussy.

“AAAHHHH!!” Delilah screamed, her body arching.

“Look, Mom,” I hissed at Delilah. “Look at your proud daughter. She wants to feel what you’re feeling. Tempt her.”

Delilah, panting heavily with a shattered mind, stared at her bound eldest daughter. Her mouth opened, and lewd words began to flow:

“Gwen, darling,” she whispered, her voice hoarse. “Look at Mom… see how happy I am… I never imagined I could feel pleasure like this… You can feel it too, my girl. Just let go… let go of your hatred… it’s just a burden causing you pain.”

Gwenneth shook her head, but her eyes were locked on my cock moving in and out of Angeline’s mouth.

“Adam… our Master…” Delilah continued, now in a more seductive tone. “He… he will give you pleasure you’ve never imagined. His cock… aaah… will ruin you in the most beautiful way, darling… look at me… see how I enjoy every inch of his cock… Aaah~! This… this is better than any magic… more satisfying than any power…”

She let out a long moan as I thrust deeper. “My body… belongs to him completely… and I’ve never felt more… more complete… Aaah~! Yes! Right there!”

Her hands grabbed her own breasts, squeezing them roughly. “Listen to me, Gwen… His cock… will heal you… will make you forget all your hatred… you just need… to surrender…”

I sped up my rhythm, making her scream. “Tell her the truth, Mom! Tell her why she must surrender!”

“Ahh~ Because… because we deserve this! We’ve sinned against him! Aaah~! And this… this is our atonement! We must serve him… with our bodies… forever!”

She gasped for air, tears streaming down her face, but this time they weren’t tears of sadness—they were tears of forced ecstasy. “Gwen… obey… feel his cock… let him ruin you… because after that ruin… you will find… true happiness… like me…”

“More vulgar, Mom!” I urged, slapping her buttock. “You’re a whore! Talk like one!”

Delilah screamed, her voice dropping to a debased husk: “Your pussy is suffering… isn’t it? I can see it… you want this big cock to tear you open… fill your womb… aaah~! Like he’s doing to me!”

She coughed but kept talking:

“You see… how lucky Angel and I are… you deserve to feel it too… just let go… let him dominate you… become his whore… like us…”

[Your Dominance over Gwenneth Increases to 85%.]

Those words were like an evil curse, piercing straight into Gwenneth’s soul.

And it aroused me even more. I accelerated the movement of my hips until I lost all control, pounding Delilah’s pussy with full force.

“I’m cumming, Mom!!!” I roared, releasing everything I had deep into her womb for the second time.

Delilah screamed, climaxing with me, her body shaking before finally collapsing limply on top of her daughter, the anal plug still lodged in her ass and her cunt dripping with my seed.

Source: Webnovel.com, updated by NovelKeep