Chapter 22: My First Time 2(R-18)

Words : 1591 Updated : Oct 7th, 2025

Explore the latest events in "Dark Lord Seduction System: Taming Wives, Daughters, Aunts, and CEOs" Chapter 22: Chapter 22: My First Time 2(R-18)Madison straddled me again, her body glistening and flushed, and...

Chapter 22: My First Time 2(R-18)Madison straddled me again, her body glistening and flushed, and her breath hit my lips like she was about to deliver the most important speech of my fucking life. Her thighs pressed against my hips, and I could feel her—wet cave, warm, ready to attempt what might go down in medical history as either a miracle or a catastrophe. She reached down between us, grabbing my cock with both hands again like she was about to mount some kind of mythical beast and needed to establish dominance first. This was it. About to take my virginity and probably reshape my entire understanding of human anatomy in the process. But then she paused, staring down at the situation like she was reconsidering the physics involved. Just looked at it. Then at me. "You’re seriously... this big?" she whispered, like the reality was just hitting her again despite all the evidence she’d already collected. "What the hell, Peter? Did you make some kind of deal with the devil?" She was acting like my dick was a natural phenomenon that defied scientific explanation. I gave a shaky laugh. "It’s not like I filed a special request with genetics." "Yeah, well," she muttered, lowering herself slightly, the head brushing against her folds. Her whole body shivered like she just touched a live wire. "Whatever cosmic force engineered this... deserves a fucking Nobel Prize." Just credited the universe with designing my equipment. This could not be real life. She positioned me carefully, and the second I felt her there—hot and soaked and sliding against the tip—I swear I almost lost my mind right then and there like some kind of premature ejaculation speedrun champion. But she was the one who gasped first like someone just told her Santa Claus was real and he was packing serious heat. "Oh my God," she breathed, stopping completely. "You’re not even inside me, and I feel like I’m being challenged by a fucking monument." She treated this like an extreme sport that should come with safety equipment and medical supervision. "We can stop—" I started, because apparently I was the kind of guy who offered to quit right before winning the lottery. She shook her head with the determination of someone who was about to climb Mount Everest in designer jeans. "No. I want it. I need to know if this is even possible." Just turned losing my virginity into a scientific experiment about the limits of human anatomy. She planted both hands on my chest, her fingers digging in like she was bracing for impact—like she needed anchor points before attempting something that should probably require a team of trained professionals and a warning label. Then her hips started to descend, slow and cautious, her body tense with focus. The head of my cock met her entrance—and just that contact had us both gasping. Her face changed. Gone was the confident, untouchable rich girl who usually walked through life like it was hers to command. What replaced it was something entirely different—something stunned and wide-eyed. Vulnerable. Like she was realizing in real time that this wasn’t going to be effortless, that this wasn’t just another conquest. I could feel her lower lips part, trembling. Her breath hitched—sharp and uneven, like her body was trying to decide whether to move forward or call for backup. Then it happened. Resistance. Like her body had slammed into a wall that didn’t belong there. A hard, unyielding barrier of stretched flesh and impossible width. Her hips stalled, locked above me, and we both felt the same truth at the exact same time. It wasn’t going in. Not easily. Not naturally. Not without effort. The reality struck like a thunderclap—we were attempting something our bodies hadn’t evolved to handle. It wasn’t just tight. It was like her body had to relearn anatomy just to let me inside. And still, she didn’t back off. She hovered there, jaw clenched, breath ragged, like she was trying to figure out if sheer willpower could override basic physics. I stared up at her, frozen in disbelief. Not just at the insane tightness or how insanely hot she looked struggling to take me—but at the insane fact that she still wanted to try. We were discovering that my equipment and her anatomy were designed by different engineering teams who never consulted each other. She groaned, softly at first, then louder like she was narrating her own struggle. "Shit. Okay... okay. You’re gonna have to give me a minute to figure out the logistics here." She rocked her hips, grinding slowly instead of forcing a straight descent—like she was trying to negotiate with my dick through careful diplomacy rather than brute force. I could feel every delicate motion, every attempt her body made to stretch and adjust, like she was coaxing herself open millimeter by impossible millimeter. Her walls fluttered around just the tip—tight, hot, trembling—and every tiny movement sent electric shocks through my cock, down my spine, and into my legs until they shook beneath her like I was riding out some kind of silent, controlled seizure. "You’re so tight," I whispered, my voice barely audible over the rush of blood in my ears, completely overwhelmed by how real this was—how much this was. "You think?" she snapped, half laughing, half whining like someone who just discovered that physics didn’t work the way she expected. "You’re like... architecturally impossible." She treated my dick like it violated building codes. She attempted another approach—easing down just a fraction of me, inching forward with the kind of careful precision you’d expect from someone defusing a live bomb. Her mouth dropped open, stunned, like she’d just witnessed a celestial event. Her entire body shuddered. "Oh my fuck," she breathed, the words trembling out of her like a prayer whispered to a god she didn’t believe in until now. "I’ve never felt anything like this in my entire spoiled existence." She looked down between us—at where we were barely joined, maybe an inch inside her—and shook her head slowly, like her brain couldn’t reconcile what her body was feeling. Her expression was pure disbelief. Like my dick had just rewritten her entire understanding of male anatomy. "You’re ruining me, Peter." She just said I was ruining her. Trust fund princess and apparent sexual expert claimed I was ruining her for other guys. I swear something shattered in my brain when she said that. My hands slid up to her waist, gripping her tightly, trying not to thrust even though every nerve in my body was screaming for more like a horny teenager’s wet dream come to life. She moved again, slower this time as I helped her sink in—rocking forward, trying to slide down more with the determination of someone attempting a world record. I felt her stretch around me. Felt her take another inch like she was conquering new territory. She moaned, deep and low in her throat. It sounded more like someone experiencing a religious awakening than anything else. Making sounds I’d only heard in very specific internet videos. Her head dropped to my shoulder, forehead resting against me, and her breath was hot against my neck like she was whispering secrets to my collarbone. "Fucking hell," she whispered, voice shaking like she was having an existential crisis. "It’s too much. It’s so much. But I want it. I want all of you inside me." She wanted all of me. The girl who could have any guy at Lincoln High wanted all of my virgin big ass cock inside her. I didn’t even know how to speak anymore because my vocabulary had been reduced to grunts and prayers to whatever deity handled teenage sexual awakenings. My heart slammed against my ribs like it was trying to escape. I was holding her like she might fly apart if I let go. Her body was so tight around me, so wet, so warm—it felt like we were already fused together even though she hadn’t taken me completely. She lifted up slightly—then pressed down again, pushing further with the persistence of someone who refused to be defeated by my anatomy. Another inch disappeared inside her. Another moan—hers this time, louder, longer, like she was crossing some line inside herself that could never be uncrossed. I was actually inside her. This was my first time and it was with the hottest girl in school who was struggling to fit me inside her. Then—she stopped again, breathing like she just ran a marathon. "I need a break," she breathed, shaking her head like she was processing new information about the universe. "You’re gonna completely destroy me." She was taking a timeout during sex because my dick was too much for her to handle. This was either the greatest compliment or the weirdest problem I’d ever had. "Yeah—okay—whatever you need—" I managed to say because apparently I was still capable of basic human decency even while losing my virginity to a goddess. But then she grinned with that wild spark flashing in her eyes again like she just remembered she was Madison fucking Torres and didn’t back down from challenges. "And when I’m ready..." she said with the confidence of someone who was about to rewrite the rules of physics, "I want to be completely destroyed." Just declared war on my virginity and promised to let me destroy her in the process. This was either the best night of my life or I was about to die from sensory overload.

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contents
Contents
Dark Lord Seduction System: Taming Wives, Daughters, Aunts, and CEOs
Dark Lord Seduction System: Taming Wives, Daughters, Aunts, and CEOs Author:almightyP
Chapter 1: Just Another Nerd’s Day in Hell Oct 6th, 2025
Chapter 2: The Laws of Opposite Attraction Oct 6th, 2025
Chapter 3: Di*k Contest? Oct 6th, 2025
Chapter 4: The Infirmary’s Unexpected Surprise Oct 7th, 2025
Chapter 5: Dark Lord Seduction System... Oct 7th, 2025
Chapter 6: A Nerd’s Status Oct 7th, 2025
Chapter 7: The Spectacle, Sudden Interest Oct 7th, 2025
Chapter 8: First Real Mission: [Seduce A Girl] Oct 7th, 2025
Chapter 9: Digital Wingman Oct 7th, 2025
Chapter 10: Humiliation: AI Strategy Meets Real Life Oct 7th, 2025
Chapter 11: Damage Control. Madison Torres Oct 7th, 2025
Chapter 12: Madison’s Invitation Oct 7th, 2025
Chapter 13: Madison Seduces Me and Home Invitation? Oct 7th, 2025
Chapter 14: Operation: Don’t Die a Virgin 1 Oct 7th, 2025
Chapter 15: Operation: Don’t Die a Virgin 2 Oct 7th, 2025
Chapter 16: Too much and Too Little Principle Oct 7th, 2025
Chapter 17: Bold Trust Fund Princess and Her Chariot Oct 7th, 2025
Chapter 18: Hand-On & Casa Torres Mansion Oct 7th, 2025
Chapter 19: My First Time 1(R-18) Oct 7th, 2025
Chapter 20: Her Tongue and Mouth 1(R-18) Oct 7th, 2025
Chapter 21: Her Tongue and Mouth 2(R-18) Oct 7th, 2025
Chapter 22: My First Time 2(R-18) Oct 7th, 2025
Chapter 23: Halfway Point: My First Time 3(R-18) Oct 7th, 2025
Chapter 24: Taking Control: My First Time 4(R-18) Oct 9th, 2025
Chapter 25: Nerd’s Bliss: My First Time 5(R-18) Oct 9th, 2025
Chapter 26: Mission Accomplished Oct 9th, 2025
Chapter 27: System Space: Sexual Frustration... Made Me a Demigod? Oct 9th, 2025
Chapter 28: Rise of the Cocksmith Oct 9th, 2025
Chapter 29: Dark Lord Mode Oct 9th, 2025
Chapter 30: Crazy Madison (R-18) Oct 9th, 2025
Chapter 31: New Peter, Same Problems Oct 9th, 2025
Chapter 32: Sex Ed by the Gods, SP Farming Oct 9th, 2025
Chapter 33: School: Day Two of Being Different Oct 9th, 2025
Chapter 34: [Mission Available: Liberate Your Teacher] Oct 9th, 2025
Chapter 35: Mission Accepted Oct 9th, 2025
Chapter 36: A Message to My Amazing Readers Oct 9th, 2025
Chapter 37: Private with Teacher Oct 9th, 2025
Chapter 38: My Main Character Moment Oct 9th, 2025
Chapter 39: My Main Character Moment 2 Oct 9th, 2025
Chapter 40: Madison’s Surprise $ Punishment Oct 9th, 2025
Chapter 41: Risk-Reward $ Madison’s Punishment (R-18) Oct 9th, 2025
Chapter 42: Risk-Reward 2 (R-18) Oct 9th, 2025
Chapter 43: Risk-Reward 2 (R-18) Oct 9th, 2025
Chapter 44: Caught? Oct 11th, 2025
Chapter 45: Shopping, Family Confrontation: When Two Worlds Collide Oct 11th, 2025
Chapter 46: Falling Apart: Between Was and Will. Oct 11th, 2025
Chapter 47: Making a Decision that will Change Me Forever! Oct 11th, 2025
Chapter 48: Isabella’s Kinky Oct 11th, 2025
Chapter 49: Sex Addict (Minimal R-18) Oct 11th, 2025
Chapter 50: The Path Oct 11th, 2025
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