The Dare (Losers, #0.5)
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Read between June 15 - June 16, 2025
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I tried to keep my eyes on Manson, his presence calming my nerves and strengthening my resolve. My resolve to partake without inhibitions, to let myself sink into this dark and twisted world of ecstasy and fear.
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My whole world was that dark room, those three laughing clowns, the taste of their sex in my mouth... and Manson, watching over it all like a demonic god.
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I’d never been restrained like that before, never had to put my trust completely in others while I allowed myself to be made helpless.
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There were so many small details I noticed about him now, even in the dim light - how his ears were pierced but he wasn’t wearing earrings, that there was a crookedness to his nose as if it had broken before, that there were tiny scars around his lips and cheekbones. He was handsome, almost pretty. His eyes were deep-set and dark but his features were soft, hardened only by the tension in his jaw.
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"Do you trust me?" The knife flashed. My heart slammed against my chest. "Yes," I gulped. "I trust you,
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I trusted Manson, I trusted him not to hurt me - not in ways I wouldn't like. 
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“You’re doing so well, angel, I’m so proud." He spoke gently, his voice soothing. "You look so pretty with your mouth filled up with his cock.”
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“We need our privacy now, boys,” he said. “Leave us.”
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a void in which everything I’d thought I knew had been turned on its head. We were in some other world, a world where pleasure and pain, fear and excitement, were all the same. 
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He looked at me with the intensity of someone trying to memorize every detail, as if his eyes alone could burn the sight of me lying there into his brain forever.
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“Remember that from now on: no touching without my permission.” 
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“I... I don’t think I can take it…” “If it’s a limit for you, I won’t do it,” he said firmly.
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The fog of my pleasured headspace cleared for a moment, allowing me to see the clarity of reality: I wasn’t truly at his mercy. I could stop him. A single word would put an end to it.
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I thought for a moment, as he waited for my answer. As scared as I was, I wanted to try it. I wanted to experience this, every terrifying second. I wanted to see how far I could push this affinity for pain. Just knowing what he intended to do was bringing a new rush of excitement over me. I took a de...
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“You can change your mind if it’s too much. Whether that’s now or 5 minutes f...
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The fact that I’d given him this power of my own free will only made the humiliation deeper, and the sweetness of my ecstasy more intense. I was handing him vengeance on a silver platt...
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hiccupping on the tears that were flowing freely. I wasn’t sure when I’d started crying. They weren’t just tears of pain: they were freeing, refreshing. It felt good to cry. It felt good to endure the pain, knowing it was of my own will. I was allowed to cry and beg and struggle. I was allowed to experience it exactly as I needed to. 
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The pain was intense. Instead of spanking me again, Manson reached out, his hand still hot from striking me, and brushed his fingers over my cheek, wiping the tears away. “Are you still okay, Jess?” he said. I took a moment to sob before I composed myself.
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“Do you deserve to come now? Hm? Do you think you deserve it?” If he’d asked me earlier, I would have screamed that yes! Of course I deserved it! I deserved it, I wanted it, I needed it! But now… “Only if you think I deserve it,” I whispered. “I’m... I’m your slave, right? So I do what you say, so…” I met his eyes with my tearful ones, giggling a little at the sheer, overwhelming sensations of it all. "Only if you want me to come." His eyes widened, shock evident on his face. I waited, trembling, hoping desperately for his mercy. I didn't have to wait long.
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As he hovered there, lips just inches away from my pussy, he looked up at me and grinned. “Say please.” He didn’t have to tell me twice. “Please, Master, please will you-” He started slowly, but it still cut off my words as efficiently as a slap. 
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“I… oh my god…” I gulped at the air, as if I had been drowning. “Manson... that was…” “Oh, you’re not done yet, angel.”
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"You're going to get off on this knife, Jess," he said. "And I'm going to hold you open, nice and still, so you don't get hurt."
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"Look at me, Jess. Right now. Don't you dare look away. I want to see all your pretty tears as you come all over this knife for me, understand?"
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My vision blurred and my eyes rolled back as I screamed with abandon, his hand stifling my noise as I came again. The first orgasm had been bliss, but this - god, I felt crushed under the sheer force of it.
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As the ecstasy rolled over me in seemingly endless waves, Manson continued to thrust inside me, laughing at every heightened shriek, at every frantic, overwhelmed twitch of my body - at the brief but violent gush of arousal that came before I could stop it. "Even squirting for me? What a good girl. Fuck, that’s beautiful."
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"Are you okay? Talk to me." "I'm great... just great…" I smiled wearily. I wondered where proud, back-talking, sassy Jessica had gone, because what was left of me wasn't her at all. All that was left was my aching, pleasured body, absolutely enamored with the man before me. That fucking freak… that loser… that absolute weirdo... had given me the best orgasms of my life.
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“I want to fuck you, Jess,” his voice was a snarl, his eyes blazing as he looked down at me. “Please do it,” I couldn’t get the words out fast enough. “Please.”
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He entered me fully, deep and hard, stretching me so tightly I cried out. I gripped the blankets as he pressed into me, long deep strokes that made my legs shake. He changed his pace in time with my sounds, perfecting his technique around my reactions, around my pleasure.
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I'd come to this party to get wasted, maybe make-out with some hot stranger. Instead my world had been turned on its head. The woman I’d thought of myself as was gone. Manson had broken the shell, the picture-perfect Jessica Martin I’d built for the world to fawn over. The Jess that remained was too exhausted to know who she was now.
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"Wanna go back downstairs?" he said. His fingers lightly brushed my cheek. "Do you?" He shrugged. "I like it here. Like this. If I get up now, it’ll probably break whatever Twilight Zone we’re in that would make you willing to get with me." I smiled. "Then don’t get up. Let’s just stay here."
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his voice softly said, "Was that...was that good for you?"
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"If the screaming orgasms didn’t convince you…” He chuckled as he leaned closer. His kiss was tender, the crown jewel on his sadism. How could a man be so carefully cruel, and so brutally gentle? "Then we can do it again?" "Absolutely."
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I didn’t want to leave his arms. His closeness brought up flickering memories of the previous night - the intensity, the passion, the brutality. It made goosebumps prickle over my skin.
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I smiled sweetly, fluttering my fingers at him. “Bye, loser.” He smirked, his tone a warning. “Jess…” He had to know what he was getting into. He could handle me, but that didn’t mean I was going to make it easy. “Sorry, sorry. You can punish me next time,” I lowered my voice, just loud enough for him to hear, “Master.”
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