Chapter 6: Intimate Night (#final)

The touch was warm and comforting, easing some of the tension in Oliver's body. Oliver nodded, swallowing hard as he tried to relax.

Alpha Grey grinned and positioned himself between Oliver's legs. He leaned down, his breath warm against Oliver's ear as he whispered, "Just tell me if it gets too much, okay?"

Oliver stared at him in shock before nodding again, he closed his eyes, preparing himself for the sensation that was about to come. Grey shifted slightly, aligning his cock with Oliver's entrance. With a deep breath, he began to push forward, slowly at first, allowing Oliver to adjust to the intrusion.

The initial penetration was slow. Oliver groaned in pain, his hands gripping the sheets tightly. The discomfort and pain were so intense, that they brought tears to his eyes. It hurts more than he imagined it would.

He could feel his Anal hole being ripped and stretched apart painfully. His vision turned hazy, and a warm liquid trickled down his anal hole, soaking a particular spot on the bed sheets.

Wait, was he....bleeding??

"It hur-ts. please st-op" Oliver managed to stutter out.

"Shhhh, the pain will stop soon, " Grey spoke softly, then he paused, noticing that it was getting harder to thrust in. He wasn't even halfway through and Oliver was already clenching tightly around his cock.

"Stop clenching. Relax" Alpha Grey said, staring down at him.

"N-no. It will hurt more," Oliver managed to gasp, clenching his dick more as his face contorted with pain and strain.

"Damn it, stop clenching. You're gonna snap my dick in half!" Alpha Grey said through gritted teeth.

Oliver relaxed a bit.

Encouraged, Alpha Grey continued his advance, inching further into Oliver. Each millimeter felt like an eternity, stretching Oliver beyond what he thought he could handle. As Alpha Grey's cock reached halfway inside, Oliver’s groans turned into a mix of pain and pleasure. The sensation was overwhelming, his body trembling under Grey's ministrations. Grey stopped again, his brow furrowed with concern as he watched Oliver's reactions closely.

"You sure you're alright?" Grey inquired, his voice soft and cautious.

Oliver felt the urge to punch him right in the face but didn't dare to do so. He caused Oliver so much pain in just a few minutes and he dared to pretend as if he cared!!

Bullshit!

"I am fine. Just do your business quickly and end this shit already" Oliver said with surpressed anger.

Grey resumed his slow, deliberate movements. This time, Oliver was more prepared, his body gradually accepting the intrusion. The pain was still there, but it was measured by a growing sense of pleasure, a heat that spread through his veins, mingling with the ache.

Oliver's body temperature went up in the blink of an eye and his whole body flushed red as Grey pushed deeper. His grip on the sheets tightened, his breaths coming in short gasps as he felt the unfamiliar emotions of pain and pleasure.

"Almost there," Grey murmured, his voice thick with pleasure as he watched Oliver struggle and submit to the sensations.

Oliver nodded, his eyes squeezed shut, focusing on the feel of Grey halfway inside him, the stretch and burn morphing into something more profound. With one final effort, Grey pushed fully inside, filling Oliver.

The room was filled with the sound of their intimacy. Thrust!

Oliver’s fingers dug into Grey's arms, his body beginning to move in sync with Grey's thrusts. The pain was still there, but it was overshadowed by a rising surge of pleasure, a heat that consumed them both.

Grey's movements grew bolder, his pace quickening, becoming rougher as he felt Oliver's body unconsciously yield to him. Oliver’s breaths came in sharp gasps, his body arching off the bed as the pleasure intensified.

"You're so skinny; I can see how far my cock is inside of you," Alpha Grey said, staring at the obvious bulge on Oliver's stomach created by his cock before caressing it.

"Alpha..." Oliver gasped his voice a plea as he neared his release.

"Fuck!," Grey responded, his voice thick with emotion as he watched Oliver cum all over his chest once again.

And then, without warning, Grey's body tensed, his back arching sharply as he reached his climax, his release washing over him in powerful waves. Oliver panted harshly and tried closing his eyes when Grey made him kneel on all fours with his ass facing Grey.

"Wha-at are you doing??" Oliver stuttered, struggling to escape from bed, but he couldn't, thanks to Grey holding him in that position.

"Did you think that was the end of today's session? Do you get to cum twice while I can't? That's not very nice" Grey said with a devilish grin on his face.

"You bastard... !" Oliver cussed

"You don't need to be scared. During our first round, I made sure to be slow and easy to stretch that damn hole of yours quite well. I am sure it wouldn't hurt this time... " Alpha Grey trailed off as he plunged two fingers into Oliver's hole, watching as it entered with ease. He pulled out his fingers which were now a bit wet, evidence of Oliver's arousal.

"Plus, you're so wet right now that if I thrust in, you might be able to take in all of me." Alpha Grey smirked making Oliver blush.

Hours passed by and finally, Alpha Grey let go of Oliver. Oliver's back hit the soft bed and his lashes drooped sadly. He was about to fall asleep. Cum twice my ass!

That bastard cummed more than thrice!

He gritted his teeth, forcing his eyes open to see Alpha Grey putting on his clothes. Oliver could tell that he was about to leave so he reached out his weak hand toward him.

"Please. Wait" His voice came out a bit low and a bit cracked.

Alpha Grey paused.

"If you're sleepy, go to sleep. We will talk tomorrow," Alpha Grey replied, and just like magic, Oliver closed his eyes and fell asleep. Alpha Grey grabbed a blanket and covered him with it before leaving.

Oliver woke up the next morning feeling extremely sore and exhausted all over. He pulled off the blanket, exposing his poor naked frame. His once fair spotless skin was now designed with different hickeys and bite marks.

That mad dog!

Oliver suddenly jolted upright, his hands clutching his stomach as an intense pain stabbed through him like a knife. He dragged his limp body to the bathroom and took a shower that was surprisingly, warm. He didn't want to show up in front of his younger siblings with his whole body screaming, "I just got fucked hard a few hours ago!!"

After getting rid of the semen. He walked out of the bathroom and put on his clothes. He was too drowsy and tired to ask Alpha Grey where his siblings were last night, and now, he didn't know where Alpha Grey was currently. Have Lily and Luke eaten? Slept? Are they feeling any form of discomfort after staying in an unfamiliar place for close to 24 hours?

Oliver opened the door of the room and limped out without a second thought. The more step he took, the more his anal hole felt as if it was on fire.

Oliver gritted his teeth, enduring the pain as he increased his pace a bit. He was too worried to pay attention to where he was going and before he could process that, he bumped into a hard chest.

He almost fell but a pair of muscular arms grabbed him, bringing him back to his feet.

"Careful there" Beta Matthew spoke softly with a chuckle.

"Beta Matthew," Oliver said in acknowledgment before bowing down a bit.

Beta Matthew was about the same age as Alpha Grey, and they had similar build and height. Beta Matthew had dark hair, blue eyes, and a well-defined jawline.

"Waoh, no need to bow so much to me," Matthew chuckled with a wide grin on his face. He was rumored to be very warm, playful, and approachable. Well, now Oliver could agree that the rumors were true.

"But...." Matthew took a few steps forward, closing the distance between them as he took a huge sniff. Oliver recoiled, feeling a little uneasy as he stepped back. Matthew seemed to realize that and raised both his hands in surrender, "I apologize for my behavior earlier. I just felt that you exuded quite the peculiar scent just now. Pardon me"

"N-no, It's okay, no need to apologize. I understand," Oliver replied with a smile. He then turned to continue limping down the hall but paused when he recollected something.

Oliver turned back and spoke, "Please, can you give me directions to the Alpha's office"

Matthew smiled as he started describing the way to Grey's office. "And there you have it," Matthew said with a huge smile on his face.

"Okay, thank you so much, Beta" Oliver said, bowing one last time before limping further down the end of the hall.

In the dimly lit hallway, Beta Matthew's piercing bright blue eyes seemed to glow with an otherworldly light as he raised his right hand to cover his face. A chilling, maniacal laughter erupted from him, its echoes bouncing off the walls of the silent corridor. "Finally," he exclaimed, "things are starting to get interesting..."