The Challenge

Soon a second finger was added, I felt my sphincter loosen. The old part of my brain told me to clench, to stop this invader from humiliating me like this, to stop this behemoth from invading my insides. For once that ego-driven voice was quickly silenced. My animalistic desire was drawing his fingers into my ass, welcoming them, opening for them. I wanted to be entirely open to him, to have him fill me with himself, to enter my essence and touch my very soul. A third finger as added, more squirts of lube. Five minutes ago, I was as tight as the Gordian Knot, now with each stroke I felt my butthole open more and more.

Suddenly he withdrew. "This will probably hurt you a bit but trust me you'll be swimming in pleasure soon enough." I heard the pump of the lube and the slathering sound as he wet his cock. I held my breath, this was the moment, this was what this entire month was leading towards. I wanted to pretend like I was just going this to get uncaged, just doing it to fulfill a bargain and move on with my life. If I was being honest though I was incredibly keen to get him inside me, I hadn't thought about my cock a single moment since he entered my apartment. I wanted my ass to please him, that was my only concern.

He put his right hand between my lower back and hip. The tip of his thumb gently rested on the base of my spine. Then I felt it on my butthole. Even without seeing it, without being penetrated by it, I could feel it's massive weight and power. He steadied his cock with his left hand and pushed into me. At first my sphincters resisted, I was eager to have him inside me but his cock was just so enormous, it was like trying to fit a city-bus down a tiny alleyway. He never stopped pushing through and suddenly he broke through.

The shock and pain of having my tight butthole stretched open by his giant log ripped through my body, I moved my back to get up by his hand pushed me back into position. The head had passed into my butt, he was inside me. My heartbeat raced, I held my breath, I savored this moment. Underneath the pain and stinging was an incredible sensation of pleasure, an unbelievable feeling that this man was filling me with his essence. I felt his left hand move opposite the right, his thumbs gently moved up and down my spine, relaxing me. "Breath, little boy." With that instruction I took a deep breath and immediately felt more of his cock enter me. His fat tube of man meat began a steady march inside my ass. His cock head mashed into my prostate, immediately I felt a sensation of ecstasy like no other in my life. His cock continued to work its way inside. The stinging and ache in my sphincter quickly gave way to immense pleasure as his member stimulated every nerve and cell my ass with its girth and power.

My ass was not just giving way to him, it was actively drawing him in, welcoming him inside me. I wanted nothing more in that moment than for him to be fully inside my rectum, to feel his weight as he bent over on top of me, forcing me down while impaling me on his cock. My butt felt incredibly full. Even back in college when I bottomed from time to time, I had never felt this full. He expanded my rectum, re-organizing my insides to fit as a sheath around his beautiful organ. Gently he whispered in my ear "Good job little one, you're halfway there." My eyes bulged out of their sockets; he still had another six inches to go!? It was impossible, no human body could every possibly fit this much cock, he'd be bulging out my mouth by the time he was done.

Determination welled inside of me though. I was fully committed to taking this entire cock. It was what Caleb wanted, it was what he would get. I arched my back and started to gently push back onto him. I wanted it all, I wanted to feel like the only thing inside my body was his fat cock. His hands steadied on my hips, drawing my back onto his cock as he kept pushing forward. Slowly we closed the gap. 8 Inches inside me. 9 inches inside me. 10 inches inside me. 11 inches. And finally I felt his balls come to rest against my own, his hips pressed against my ass cheeks. He was fully seated in my ass.

The feeling was euphoric. I felt like I had just climbed a mountain, like I could conquer anything if I could take this monster in my ass. The pain of his intrusion had fully replaced itself with ecstatic sexual pleasure. He flexed his cock and I immediately felt like putty in his hands. "Most people tap out after the first six inches, I'm very proud of you taking me this deep." His words enthralled me. "You can start fucking me now, my butt is all yours."

He didn't wait for me to back off the invitation and I felt him start to pull out. With three inches outside me he slammed back home. A jet of white-hot pleasure shot through my ass out to the rest of my body, he wanted to stay deep in me, and I was a-okay with that if it was going to feel this heavenly. He settled into a rhythm, slowly pulling out a few inches and quickly slamming himself home. I was drooling, moaning, unable to form words and sentences, all I could think about was this cock and how incredible it felt inside my butt. He kept his hands on my hips, held my ass in place as his hard strokes hit home over and over again.

After a while he started to change his stroke, pulling out six inches and steadily pushing it home. A nice, even tempo of in and out. His motions were driving me insane, I had never felt sexual pleasure like this, this was the very best sex I had ever had despite the fact that my cock was soft and in a cage. I moaned deeper, the grunts and groans escaping my mouth as involuntary sensations, I could not stop myself if I had wanted to, his cock was forcing them out of me.

The pleasure in my prostate was insane, thousands of volts of electricity tingling and jolting with every stroke. His head would mash against my gland, drawing a moan and an ooze of pleasure, this would follow with a massive length of cock slithering past, continuing my exquisite ecstasy. I couldn't escape the pleasure of his cock for a nano-second, I was entirely hooked on him. My own cock flopped back in forth in time with his strokes, bobbing to and fro, the cage clanging gently. It hung like a pendulum, it's only purpose to sway in sync with his fucking.

Gradually he elongated his stroke until finally I was taking the entire length. He withdrew until his fat head was the only thing keeping my sphincter open and then push his entire length inside me. The pleasure just kept escalating; I didn't know that sex could ever reach these heights. He continued this way for what seemed like hours and hours.

I felt an orgasm welling inside me. Not from my cock like every other orgasm in my life. This one was starting deep inside my butt. It built slowly, powerfully, with every stroke in and out Caleb would add another brick to the wall, slowly erecting a masterpiece. My mind was incoherent, I was lost in my own orgasmic sensation, the build of my orgasm felt better and more intense than any finish I had ever achieved before this moment. It wasn't even close, this topped them all and he was still going.

After what felt like an eternity I felt myself ready to explode, ready to take the ultimate plunge off the mountain, to let myself be forcefully taken and orgasmed. I prepared myself to plunge.

And suddenly I felt nothing. He had pulled out entirely. I whimpered, "please, please I need it." I had been so close, I felt my orgasm shrinking, falling away into nothingness, a gigantic potential that had come to naught. I felt my asshole gape, left wide open by the exit of his massive cock, the air felt cool as it rushed to fill the void, leaving me feeling emptier than ever.

Suddenly I heard metal clang on the table right next to my face. It was the keys to my cage. "I'll give you a choice. You can uncage yourself and jerk yourself to your orgasm. Or, you can get my cock back in your ass. I'll keep you caged up, you'll analgasm around my massive tool all while having a soft, encaged cock. But if you want my cock back you have to agree to give me another month locked in chastity." To punctuate his choice I felt him rubbing the head of his beautiful cock around the rim of my ass. He swirled the head around my asshole, using his left hand to gently push it forward, enough to remind me of what I had lost but not enough to bring my orgasm back. He was so close to being back inside me, so close to filling me up again.

I grabbed the keys in my left hand. I held my freedom for the first time in a month.

Then I threw them across the room. I didn't need freedom, I needed dick.

"Good choice" he whispered the words as I felt him sink his entire cock back inside my ass. Whatever feelings of orgasm had slipped away were suddenly back with a vengeance, the denial had merely served to heighten my stimulation, in no time flat he was back to hammering my ass, forcing grunts and moans from me as my orgasm grew and grew, it was higher and stronger than every before. He bent over to whisper in my ear, I felt his weight on my back while he somehow managed to continue fucking my hard, "you get my cum when I get your cum."

This was enough to send me over the edge, I felt the cum explode from my caged penis, a torrent of fluid forced it's way out of my soft little pecker, it oozed in one continuous, gloppy, strand. My rectum spasmed on around his cock, my prostate went super-nova, my ass clenched, my spine tingled, my toes curled. My entire body seemed to both tense and go limp at alternating intervals, a full-body intensive orgasm that just kept going and going.

At the same time, I felt Calebs cock swell in my ass and he buried himself deep, he pumped his load as far inside me as he could, I could feel every powerful shot as his cum expanded its presence in my ass. His load was massive. The thought of all this made my own orgasm longer, more and more of my cum dribbled out of my cage, my balls twitched, my mind went almost blank. The sensations of pleasure may be causing my cock to ooze, but the brain was fixated solely on the pleasure in my ass. It was my entire being. All I could understand in that moment was his cum filling me, and my ass spasming around his majestic beast of a cock. Our orgasms seemed to echo on for an eternity, spurt after spurt filled me up, rope after rope drained from my cage.

Caleb collapsed on top of me. His cock still buried all the way in my ass, still seeming to spurt a few drops of cum now and again. For the first time in perhaps my entire life I felt completely sexually sated. I wasn't focused on the next score; I wasn't thinking about the next time I would get off. In that moment I was just perfectly happy. Calebs weight on top of me felt extremely comforting. I could feel his panting, he gulped the air trying to catch his breath. I swelled with pride, I had taken his monster cock and my ass had made him have a super orgasm. My ass did that, it brought him that pleasure. Slowly he composed himself, rising off my back, kissing down my spine as he went. Each kiss he planted caused a twitch in my brain, a tiny act of intimacy in a way that I had never known before.

His cock softened; he gradually withdrew it. My anus gaped. What was once a tight-pristine hole was now a loose, gaping mess of lube and cum. I reached back to feel myself, my ass felt a puffy. I was proud of my butthole; it had done good work today.

I felt my asshole for a minute or two and then was aware that Caleb was behind me once again. He pushed something thick against my ass. Old me would have protested, new me wanted this to happen. I didn't know what it was, but my ass was open for business. He pushed around 8 inches, I felt it's girth gradually increase, and finally it sloped off. My ass closed a bit around the neck and I felt the base nestle between my ass cheeks. It was a buttplug, a pretty big one at that.

"I wanted my cum plugged up inside you when we go out tonight. I like my boys caged and plugged." His words were definitive, commanding.

"What do you mean?" I was confused, I just assumed he was going to leave. I had forgotten that I had given him another month of chastity, I had forgotten that I agreed to go through this insane ordeal once again.

"Let's be honest, Peter, you're never going to ask for that key back. I'm going to keep your cock locked up forever because you won't ever want to go back to being a top. Your ass enjoyed that way too much, I'd bet it was the best orgasm you ever had. So next month I'll make you the same deal, you can unlock yourself, or keep my cock inside you. You're going to choose my cock over yours once again. The next time you'll do the same, eventually I won't even bother asking, I'll just know what choice you would make. You thought that just because you have a big dick that you were meant to be a top. But now that you've seen the light, you realize that you're a butt-boy, you will always be an anal-slut. That's your life now."

The thoughts rattled through my brain. Could this really be what I wanted? Truth be told, I couldn't imagine ever wanting a cock-orgasm again in that moment. The way he fucked my butt was too incredible. I needed it again.

"I... think you may be right." It was a big admission for me. I was giving him my power, perhaps permanently. I squeeze the plug with my butthole, it gave me some confidence that I was doing the right thing. It felt right. "But I'm not sure I can wait another month, I may want this to be a regular thing."

"I know I'm right. And you'll wait as long as I want you to wait. Though honestly your hole is delicious enough that I'm not sure I'll be able to contain myself." He winked at me, my heart fluttered. "Now, if I'm going to hold your key long term I actually want to get to know you a bit. And if I didn't plug you up you'd be farting cum into your pants all through dinner. Plus I'm gonna guess you didn't eat anything all day like a good little bottom boy."

I thought for a moment. "Wait, are we going on a date?" I felt his massive load slosh around in my rectum and was suddenly glad to have something to hold it all in. I wanted his cum to stay inside me forever, a reminder of the magic we had shared.

"Yes we are. I know this great Chinese place a few blocks from here that stays open late. Get dressed, I'm buying." He started to dress himself. I looked longingly at his beautiful cock, getting one last image in my mind before it disappeared beneath a shroud of cloth. He saw me staring, "If you're lucky I'll let you have another go at it later tonight."

I disappeared into my bedroom. Walking with the plug felt amazing. Every movement caused it to tingle inside my ass. I chose a thong-style underwear so that firm satin would push the base of the plug a bit further inside me. In no time flat I was ready to go and we were out the door.

Never in a million years would I think that I would be going on a date with the man who caged, creampied and plugged me. Now I almost could not imagine it any other way, this seemed like the only possible conclusion. I also never thought I would be this excited for whatever was to come next. He took my hand in his own while we casually paraded down the street, causing me to focus on the present, squeeze the ass on the plug, and fully enjoy the moment.