Imprisoned Ch 04

My eyes burst open in a frenzy. Standing above me, Carson's glowing eyes danced in the darkness. He was just standing there, watching me, his eyes piercing through my soul. It made me want to turn my head in the other direction or at the very least, close them, so I didn't have to see his gruesome grin.

"Hello, Maddy, love," he said, still maintaining that smile of his.

What was he up to?

"I wanted to have a little chat."

This couldn't be good.

"How about it?"

NO! I don't want to talk to you. You've taken my whole life away from me. Why would I want to converse with you let alone look you in the eye?

I nodded my head and said a small, "Yes."

"Sit up, then, Maddy," he told me. "I've freed you from your handcuffs."

I sat up, hesitantly. Drawing my legs to my stomach, I held myself. My chin dropped to my knees, and I looked at my captor with sullen eyes. I felt unclean just being in the same room as him. Wondering if I would ever feel clean again, I had begun taking advantage of our 6 a.m. shower sessions. But even the water didn't seem to cleanse me anymore. Nothing could... except my freedom. However, after three and a half months of my imprisonment, my optimism had depleted. And who could blame me?

"Our time together has certainly been..." Carson searched for the right word. "Engaging," he finally decided upon. "But I don't believe that we've made much progress in our overall relationship."

What the fuck was he talking about? Our relationship?! That had ended even before he imprisoned me. Did he refuse to accept it? Had he blocked out the memories? I stared at him confusedly.

Carson came closer to me. He took a seat on my bed and placed a hand on my calf. He ran his fingers up and down my skin; a shiver tore down my spine. Then, he said, "I know that you still somewhat resent me, Maddy. I'm not blind. I can tell that you don't particularly enjoy being trapped in a basement... especially one that's not furnished."

The bastard chuckled at that. He became serious again. "But, Maddy, love, it's all for your own good. You see, in order for our relationship to develop properly, I wanted you to be isolated for a while. I wanted ME to be your only focus. That way, you could clear your head and stop thinking so much."

He smiled lightly. "I know how much you think, Maddy. Don't take me for a fool. Remember in class, you would always be the one asking the best questions. But then, taking an analytical role -- always so amusing, of course -- you would answer your question before you would even allow me to it. Sometimes, Maddy, love, you over-think things. That's what I wanted you to stop doing. And if I'm right, it's worked. You've calmed down quite a bit since you first arrived. I've noticed a change in you."

Yes, I wanted to say. What you've noticed is my hope dying...

Carson continued stroking my calf. He said, "But I want to reward you now. You know, for all the progress that you've made."

Admittedly, the thought of a reward made me both nervous and incredibly excited. He had never used that word around me. Reward. It was always some kind of punishment -- whether sexually, physically, or mentally. Never rewards. Until now.

I dared to ask, "What kind of reward?"

Carson leaned in close, and I could feel his breath on me. Looking deep into my eyes, the hand that had been on my calf, traced around my skin and landed on my thigh. I could tell that he was getting turned on as his fingers ran across my panties. He could feel the heat radiating from my pussy. I tensed a little, more curious about the reward than about him raping me again.

Carson whispered one word, "Friends."

That night, I contemplated the idea of "friends." What could Carson have meant by that? I had a few ideas, but they were all horrible. If he meant what I thought, then I didn't want to have friends. I didn't want more girls to be imprisoned down here like me. But then again... would he be that stupid? Maybe the two of us could figure out a way to get out of here. And besides, that would really entice the police to search even harder for me since the girl would probably go to Brunswick High as well. As I drifted off to sleep, I smiled to myself for the first time in a long while. The more I thought about having a "friend" down here with me, the more I grew to actually like the idea. Little did I know, I was in for a very big surprise.

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"Madison," Carson said properly. "I want you to meet our new friend, Wes Sonner."

I looked up at the tall man from my position on the bed. He looked like a normal guy in his late twenties. Brown shaggy hair, dark chocolate eyes, and a little scruff along his chin. He didn't seem like the kind of guy that would do this, not something this horrible. But I guess you don't always know about people's sick fetishes by just looking at them...

"Nice to meet you, Madison," Wes said and stuck out a hand.

I wanted to spit in it. Instead I shook his hand and said, "It's just Maddy." My tone of voice was harsher than I intended and Wes seemed a little taken aback at first. Then he suddenly grabbed my chin and bent down to meet my eyes.

"Oh so you're a feisty one, huh?"

Carson laughed and said, "Yes, she certainly is. But we've been working on that, right, Maddy, love?"

"Mhm," I hummed and tried pulling away from Wes' grip. He budged with no resistance. Losing interest in me for a moment, he looked to Carson.

"When are we going to talk business?" he wanted to know.

Carson folded his arms and replied with, "Well, don't you want a trial run before you buy the product?"

"Ha! I guess you're right about that."

"You have much to learn, my friend," Carson told him. "You can start now if you'd like."

"Will you join in?"

Carson grinned a little. "I'll see how I feel."

"Carson, just so you know," Wes started to say, but my captor interrupted the young man.

"I understand that you're straight. I am too. We just need to be confident enough to not let that interfere with any of our... desires. I won't go beyond the limits that we've discussed. I can promise you that."

"Okay, good," Wes said, sounding reassured. He started to get undressed.

Carson reverted his attention to me. "But that doesn't mean I won't go beyond the limits with you, Maddy, love. We all know that, don't we?"

I squirmed on the bed, wishing that this wasn't happening. I tried to imagine my paradise -- the one with my family on the beach, sipping ice teas. Where was that image when I needed it the most? It wasn't with me today. All I could think about was how I was about to get double-teamed by two men. And even worse, I'd be losing my anal virginity. Part of me hoped that Wes would do it since I didn't know the man and he would be easier to forget about (unless, of course, he was going to be a long-term friend). The other part of me hoped that Carson would do it since I was more accustomed to his cock. But as soon as I saw Wes' 9-inch monster, the part of me that wanted Wes disappeared. I could almost hear myself begging for Carson. Ugh. The thought almost made me gag.

Wes came near me and lowered himself to the ground. While on his knees by the side of my bed, he began kissing around my bellybutton and his hands explored the rest of me. One hand landed on my breast and he circled his fingers around my nipple until it grew hard. His other hand fell beneath my thighs and he started teasing my clit. Rubbing the nub with his thumb, I could feel myself moisten. Wes' hot breath came nearer to my pelvis as he continued kissing me. I squeezed my eyes shut and hoped that he wouldn't start licking my pussy. But I could feel my body asking for it.

Carson was getting a kick out of this and he, too, had undressed, allowing his cock to spring from his pants. He came around to the top of the bed and brushed Wes' hand away from my breasts. Wes got the idea. He started paying full attention to my pussy now as he came around to the foot of my bed and started teasing me. I could feel lips close to my vagina. When he blew on me, I shook in anticipation, and he just laughed. Then, he gave my clit a quick lick, tasting my practically overflowing juices.

Carson bent over and whispered in my ear, "How are you enjoying this, Maddy, love?" Running his hands up and down, he began tweaking my nipples. They were already stone hard. I didn't protest. I couldn't protest. My voice had been stolen away in the blur of the moment.

Wes worked on my clit with his tongue as he grabbed my ass cheeks and drew me in closer to him. Lapping up my juices, he nuzzled his nose against me, taking in my scent. Spreading my cheeks apart, I could feel his fingers probing the outer rim of my asshole.

My eyes burst open. Reality hit me hard. I didn't like what he was doing down there. I didn't want anything to do with anal sex. That had always been my one rule, even with Carson in the beginning. My eyes darted up at Carson who was busy toying with my tits. Carson gave me a devilish smile, thinking that I was secretly enjoying what was happening here. And maybe...just maybe...I enjoyed the sensations pounding through my veins and the sexual heat exploding across my body and the wet licks of Wes' long tongue stroking my clit. But I didn't enjoy these men, neither Carson nor Wes. And that ruined everything for me as it always did. But now, more than ever. As Wes continued trying to probe my anus, I knew I couldn't hold it in much longer.

"Carson," I whispered in the most innocent way.

Carson looked at me.

"Please," I told him. "Maybe you can take over my..." I was getting squirmish about the situation. "Well, you know, the anal part."

Wes was too busy eating me out and poking at my tight asshole to comprehend my words, so we weren't afraid offending him. Carson just nodded at me and stood up. He unlocked my handcuffs and declared, "Wes, it's time."

Wes nodded his head and took his face away from my pussy. He seemed a little awkward, as if he had never done this before. Expectedly, Carson seemed to enjoy being in full control. As Wes stood up, he watched Carson grab me and lift me off the mattress. I squealed a little, surprised by his force. Since my imprisonment, I had become fairly petite at 5'3 and no more than 105 pounds, so Carson enjoyed throwing me around much more these days. He flipped me around so that his cock pressed up between my ass cheeks. My naked body was on display for Wes and I avoided his hungry eyes. He started coming toward Carson and I, ready to pounce on me and have his cock indulge my pussy, but Carson barked out, "Stop!"

Wes looked a little confused, and Carson just said, "She's new to this." Nodding his head, Wes understood. He began to watch as Carson fondled with my breasts, and he began to masturbate to the scene.

Carson held me close, pressing the side of his face against mine. "Don't be afraid, Maddy, love. It'll only hurt for a second."

"Carson?" I said. "I really don't want this."

"It'll be okay." He began fingering my asshole, sliding one finger deep inside. "Damn, you're tight."

"It hurts already, Carson," I whined. "I really wish that we could do something else. Maybe you can tell Wes to go home and we can do something just the two of us."

"I just need a little lubricant," Carson thought aloud. He sunk his index finger into my pussy hole and I gasped. Carson held me tight. "Shhh...Maddy, love. I'm telling it's going to be okay. Trust me."

"Please, Carson," I begged. "Don't do this. I'm not enjoying it."

"Ahhh, there we go," Carson said, inserting a second lubricated finger into my ass. He jerked his fingers in and out, feeling my muscles relax a bit. I knew it was better to be loose for this. I had read enough Cosmo magazines to understand the basics of anal sex. But at the same time, I had never been interested. As Carson dove his fingers deeper into me, my disgust for him only grew stronger. And I hated Wes too. He stood only a few feet away from us, yanking his monster cock so hard that it almost looked painful.

He pushed in a third finger and I cried out. I could feel my virgin asshole slowly being torn apart. How was this sexually exciting in any way? Why did people like this kind of thing? "Carson, please, stop! This seriously hurts. I'm not kidding. Please, Carson..." I felt tears come to my eyes and although I wanted to wipe them away, I knew it would be pointless. There would be more tears in no time. I was just waiting for the worst now.

"You're all set, Maddy, love," Carson finally said when he thought I was loose enough. "Wes come over here so Maddy can lean on you."

With no hesitation, Wes strode toward me. Carson pushed down on my back harshly and I fell on top of Wes' bare chest. Our new friend held me up, letting my breasts press up against him. Bent over like how I was, my ass lifted in the air slightly, giving Carson the perfect exposure to anally penetrate me.

Once more, I tried to beg for him to stop. Tears rolling down my face, I cried, "Carson, please, please, PLEASE stop. I'm begging you to stop this. Please don't do this, Carson. I'll do anything else. Just not this."

Carson ignored me. The top of his penis pushed at my anal opening. Nothing had ever felt so painful in my life as Carson pushed himself into my asshole. Even his three fingers couldn't come close to preparing me for this. I slid further on top of Wes, my hands on his shoulders and my fingernails digging into his skin. Wes responded with taking my breasts into his hands and squeezing them tightly. I tried closing my eyes, biting my lip, pressing my forehead against Wes' chest -- anything to stop the pain, but it didn't work.

"Come on, Maddy," Carson barked at me. "Loosen up!" He slapped my ass and then grabbed hold of it. He started sliding his cock in and out at a medium-paced rhythm. Grunting each time his cock slid deep within me, I knew it was only a matter of time before he would want Wes joining in. I jerked on top of Wes, holding on to him, trying to keep a standing position, but Wes couldn't take it any more.

"I'm testing out the product now," he told Carson half-jokingly. Carson, completely engaged with fucking my ass, didn't respond. Wes lifted me up, which made Carson adjust his position as well. Wes ordered me to wrap his legs around him and I did so. Suddenly, I felt his huge cock press against the lips of my vagina. When he entered me, I cried out again. He began fucking me to the same rhythm as Carson. I felt so filled with my two entrances being penetrated.

Wes gripped the sides of my legs and kept pounding into me. His cock, bigger than Carson's, slammed into my wet pussy. And all while, Carson tried to regain control by pushing back harder. Strangely enough, the struggle for power between my captor and Wes amused me.

But tears continued streaming down my cheeks. Sandwiched between the two men, I felt overwhelmed by the sensations erupting inside of me. Part of me hated this. The other part of me enjoyed the peculiar feeling of it all. With my emotions scattered all across the boards, I couldn't help but to cry. I felt degraded, but I felt like a prize. I felt hopeless, but I felt alive. The pain was excruciating, but it was was slowly turning into something else. And I hated these men, but I loved this warmth...this feeling...like I was about to...

My cries filled the air as an orgasm burst from me. Shaking from head to toe, the orgasm took control of my body and made me forget about everything for a moment. The raping, the basement, my captor, our new friend. It was just a feeling. An amazing, beautiful feeling that couldn't be expressed well enough with words. But my body, as it rocked with multiple orgasms, expressed everything.