The Challenge

Hello. I woke up in the middle of the night a few days ago and this scene kept playing over and over in my head, I couldn't fall back asleep. I was so fixated on it that I just had to write it down. To the small handful of you who are fans of my other series and are waiting on the next installment, please do not fret. The next few chapters are already written and are being edited. I really just needed to get this off my brain. Anyway, enjoy!

******************

'I really hope that he isn't some limp-dick bottom.' The thought repeated itself in my mind, making it difficult to focus on my work during that entire Friday. My law firm was working on the Kansas City Southern merger deal and I was stressed, everyone here at the NYC office was. Most folks around the office would call me incredibly cocky, I liked to think that I just really understood how much value I brought to the table. But in a deal this big, everyone needs to blow off a little steam. Which is why when someone finally responded to the challenge on my hookup app, I was eager. It was very favorite game and no other man had dared to take up the challenge in months.

My game was simple. Two men meet and compete in three challenges. First, who has the bigger cock. Second, who can last the longest while the other is trying to get them off. Third, who shoots the biggest load. Winner is the one who takes two of the three events. The loser gets his cock locked in a chastity cage for a full month. At the end of the month, the winner gets to fuck the loser while he's still caged.

Like a lot of other men in corporate America, I like having power over others. I especially like taking other alphas down. Which is why I was really hoping that this guy wasn't just some tiny sub looking to be dominated for a bit. I wanted a challenge, I wanted the stakes to be high, I wanted to take another alpha and make him submit to a superior man. It was the best feeling in the world, when it really came down to it this was my only fetish. It wasn't even about the sex; it was about the winning.

This also happens to be a game that I have never lost. My cock was a thing of beauty. 9 inches uncut, 8 inches in circumference and a pair of low-hanging meaty clackers. There had been a few times where I had won the first round without even needing to get hard, where my flaccid cock had dwarfed my opponent. It was always an exhilarating feeling to watch the color drain from some little shits face when he realized that he had already lost the game. I have incredible control too, I can let a giant torrent of cum out almost on demand, which means I can hold off forever. Some of my favorite experiences were when I made my opponent cum in a few minutes and then made him spend more than an hour trying to coax a load out of me. It was their first experience being dominated by me, I loved when they bent to my will.

At three I ducked out early. I pinged the partner I worked with and told him that I would be putting in a long night so wanted to transition home before rush hour. Everyone was so busy that I just got a 'fine' in reply. A nicer response than he normally sent. I often thought about how I could take him down a few pegs, if he knew I had the true alpha-cock he'd treat me with the respect that I deserved.

When I got home, I checked the clock. My opponent had agreed to meet me on my home turf at 5:30. True to my word I hopped on my laptop and got a few more hours of work done. At the appointed time I heard a knock on the door.

I was pleasantly surprised to see that he was a lot like me. Tall, well-groomed facial hair and an obviously fit body underneath his expensive suit. "Are you Peter?" His tone was all business, he was here for a purpose, not to make bullshit small talk. I liked this guy; I would enjoy taking him down.

"Yes. That makes you Caleb." He nodded curtly and brushed his way through my apartment door.

"I have to say, I was instantly interested when I saw the challenge on your profile. This seems like it's going to be a really fun game."

I smirked; this was a good sign. Some guys tried to run away from the challenge, he was going to meet it head on. "I certainly enjoy it. I have to warn you though, I've been playing for years and never lose. You may not find it so fun when I lock you up for a month." This was a classic scare tactic I employed, with most guys I could start to see them sweat at this point, knowing that they were going to lose even before I whipped it out.

Caleb didn't miss a beat though. "I have one addition to the stakes though. When was the last time you were tested? I got a clean bill from the doctor this morning, I've got the papers here. If you've been tested recently, I propose that the winner gets to take the loser bareback."

An excellent evolution to the game. "I was tested last week, free and clear. I can email you the papers. And don't worry, I'll get tested again before I fuck you next month just to put you at ease." I was still trying to psyche him out but he brushed it aside just as quickly "I'm already at ease, I think you'll be chaste as an old nun for the next month." His retort was immediate, I liked his feistiness, it would be fun to break this wild stallion.

The deal had been made. With that Caleb started to undress. "Let's do this, I've got shit to do tonight." His confidence was entrancing, he was beating aside all my attacks. I'd just have to let my cock do the talking. My biggest weapon as still sheathed.

Soon it was just the underwear. He had a pretty decent looking bulge, but I was still confident. "I know you may be a bit scared right now, but no backing out at this point." He just grunted in response and pulled his boxers all the way down.

What I saw before me left me stunned. Even flaccid he was sporting an absolute monster. An already thick shaft led to a fat mushroom tip, all hanging down along a humongous set of testicles. "You going to show my yours or what?" He must have noticed that I was gaping at him, for a few moments I had been so distracted that I was unable to focus on the task at hand. He started to stroke himself, stimulating his glands and getting some blood flow to his massive member. My vague hope that he was a shower and not a grower was quickly dashed, it just kept getting bigger and bigger. The head ballooned, the shaft straightened, everything got thicker. "For a cocky little shit, you sure seem scared to let me see your little dick." His words interrupted my trance and I realized that I was still in my underwear. I gulped and took a deep breath, feeling that my own cock may have shrunk a little bit in fear.

No. This was my game, I was the master of this universe. I quickly stripped and proudly displayed myself to him. "That's not too bad I guess." His tone was simultaneously extremely calm and hostile. I couldn't believe the lack of respect, coming into my house and insulting me like this. I'd show him. I started to jerk myself, he'd be impressed when I was fully hard. I felt the blood start to return to my dick and it start to rise. I'd take him down.

But his cock hadn't stopped growing either. After a minute or two we were both fully hard. He moved towards me and put his cock next to my own. He grabbed both dicks in his meaty hands to fully compare their sizes. "I'll give you this, Peter, you may not have a little sissy dick, but I've got about three inches in length and some thickness on you. Round 1 is mine." My lawyer brain immediately tried to think of some technicality, I tried to think of some obscure measurement or something I could use. I came up empty, I would just need to win the latter two rounds. My confidence started to falter but I still sure of myself, I could last forever and shot giant loads, there was no way that he could match me there.

"Right, well it's best of three you know." I was still trying to recover from the humiliation. He had bested my cock, no one ever bested my cock. Anger welled inside him, he clearly needed to be put in his place, taught how to respect his superiors. I needed to take this cocky fuck down, his cock wouldn't be a threat once Caleb was caged.

"How do you measure round 3? Got a measuring cup or something?" Caleb's tone was still so arrogant, I hated him in that moment.

"I'll be honest, it's never been close enough that I've needed to measure. I think we'll just be able to tell which load wins. No offense, but I shoot the biggest I've ever seen."

"That will work I suppose, I don't think you'll have any doubt when mine wins." Caleb seemed like he was talking shit but beneath his words he seemed to have a supreme confidence. I was quickly losing my composure, there was no way I could survive a month locked up, there was no way that I could get fucked by this anaconda. I hadn't bottomed in almost a decade, I barely tolerated giving my partners a reach around. In my sex life, I fucked, everyone was just glad that I honored them enough to let them take it.

We sat across from each other, each taking a hand and placing it on the others cock. My hands were big but they didn't go all around his meat. I looked down and pleasantly saw that he was facing the same problem. He may be a few inches longer but seeing that our thicknesses were close gave me some confidence.

I started to jerk, looking him directly in the eyes the entire time. This was something I did a lot, I liked to see the will drain from the other man's eyes when he realized he was going to lose, that he was going to cum and that I wasn't close. It helped intimidate, helped to reinforce who was really the alpha.

He started jerking me as well. Immediately I knew that something was wrong. His technique was incredible. I had no idea what he was doing with his hands, I can barely describe it, but his strokes were otherworldly. The way he applied and eased pressure, the way he caught the most sensitive areas of the head, the speed, the tempo. It was the best handjob of my life. I started into his eyes, trying my best to maintain my composure, his stroking was making it really difficult to focus on my own task, I was sloppily jerking him, he was barely aroused, at this rate It'd take me an hour to get him to cum.

I felt my orgasm welling up inside me. This wasn't happening. I couldn't lose. The humiliation burned me deeply, I broke my eye contact with him, but he continued to look directly at me. His gaze felt like a laser beam, a hot energy injecting shame onto me for failing. He was winning, I was losing.

At this point my subconscious had nearly given up. He was giving me an incredible amount of pleasure, it was nearly impossible for me to focus on giving anything back to him.

Finally I broke, I started to pant and sweat, I was close to orgasm and it was powerful enough that I stopped concentrating at all on trying to get him off. He had won. I was going to cum, he had the bigger cock, even if I shot the biggest load in history I would lose. So, I gave in. My humiliation, anger and shame at allowing this man to best me mixed around in my brain with the orgasmic pleasure he was giving me, I couldn't focus, I couldn't regain control, and suddenly I lost it all. My orgasm ruptured from my cock with explosive force, rope after thick rope erupted from my and shot across my own chest and belly. He was aiming my cock back at me, making me cum on myself. The realization deepened my own humiliation, my face turned beat red.

But I was enjoying after second of it. The pleasure I was feeling was paramount though, it conquered every other emotion and sensation. The orgasm was incredible, toe-curling, mind numbing. By the end I was out of breath and covered in my own cum. I felt him wipe his hand on my thighs. My shame burned even deeper.

He mercifully gave me a minute or two to recover. Stroking his own cock to keep it nice and hard. "I suppose this means I win." I hated him for saying that, this cocky fuck didn't know who I was, he didn't know how many men I had bested. "We still have to figure out who won round 3 though and you didn't even come close to making me orgasm. What are we going to do about that?"

I looked down at myself, I had cum a fairly impressive load. I may be able to salvage a bit of my dignity if I won round 3. I'd need to get him off, show him that at the very least I wasn't a total bitch. "It's been really stressful at work I guess, I really needed to blow off steam, I think that's why you might have won the second round." The excuse was flimsy, I said it to try to save face with myself. I knew that he didn't believe it though, I didn't believe it myself. But I was determined that I would take at least the last round. I threw myself back into the handjob with increased fury. I tried all of my tricks, I tried to emulate some of the things that he did to me. He just sat back and let it happen. It was like I wasn't doing anything at all.

After twenty minutes my arm was starting to cramp. I was determined to make it through, I would prove that I had the bigger load, I would make him respect me. I kept pumping away. Another ten minutes went by and he seemed like he could go on for another few hours.

"I know you normally jerk for this part, but honestly I have places to be. I think it will go faster if you suck me." I didn't think he could humiliate my any further. Here I was, covered in my own cum, my own cock soft and limp while my hand was wrapped around his thick, long, dominant monster, all the while I couldn't get him off to save my life. And now, he wanted me to blow him. "Or you could just forfeit the third round I guess." This bastard, he knew exactly what to say to push my buttons.

I leaned over the moved to take the cock in my mouth. "no no no, get on your knees first. It will help keep your throat open." My face burned with humiliation. But I did it, I got on my knees between his legs. I looked up at him, looked at the monster he had, saw his firm, hard body and handsome face and knew that I was beaten. From my perspective it was like looking up at a redwood. I put the cock in my mouth and started blowing him. He put his hand on the back of my head, not to force me down, just to reinforce who was in charge. I gagged and sputtered, I almost never blew the guys I slept with, as far as I was concerned it was their responsibility to get themselves off. My inexperience showed though and it seemed like I was nowhere closer to getting this guy off than I was before.

After almost an hour of servicing his member, he looked down at me and said "I've gotta go soon so let me finish this." As if on his own mental command, the cock started to swell in my mouth, his balls tensed, and his head rolled back. Suddenly I felt him start to shoot, his first shot of cum completely covered the inside of my mouth, coating what felt like every inch in his salty seed. He shot again, this time it flew towards my throat. I started to gag, trying my best to swallow some of the load to make room for what was to come. And kept coming it did, he must have shot nearly a dozen thick ropes of jizz in my throat before he was done. My lips were still locked around, gently suckling. I cursed myself for how weak I must look but I couldn't stop, I kept sucking, trying to get every last drop in my mouth.

He put a hand on the side of my head, gently bobbing my face up and down in a slow rhythm as I sucked the last drops from his fat cockhead. "Since you gobbled it all down, I'm not sure how we can measure who had the bigger load. I really was expecting a prissy guy like you to not swallow, I thought I'd have to shoot it on your face. But based on how you were gagging and puffing your cheeks I'd say that I won that round as well. What do you think?" I meekly looked up at him, my mouth still stuff with his member, it still filling my completely even though it was softening, and merely nodded. It was the biggest load I had ever felt, a single man bukkake and he had made me swallow it all. And for some reason I had enjoyed it. I hated myself in that moment, hated that he had taken my power.

"You seem like you want to go for another round of face-riding on my cock, but I seriously have to go. Let's get you locked up and I'll be on my way." Fuck. In my battle to tame his massive snake and swallow his load I'd let it slip my mind. This loss meant I was going to be locked in chastity for a full month, and he would hold the key. I gave his cock one last little tonsil-kiss and finally let it slip from my mouth with a pop. I looked at his cock, covered in my spit and the remnants of his load, it was magnificent even when partially flaccid. I couldn't help but be turned on by its power.

"Look man, I know we had some fun, but you don't really want to lock me up, do you?" It was my last, desperate attempt to avoid my fate. I felt ashamed, but blowing him had made me hornier than I've felt in months, as soon as he was gone, I was going to jack myself off, but only if he left with me uncaged.

"Not a chance little man, I'm going to enjoy holding your key for the next month. I brought a cage of my own, where's yours? I'll be nice and let you pick which one you want." I reluctantly got off my knees and went to retrieve the cage, the very same one that I had used to lock away dozens of other men who I had bested in the game. Now I was the defeated, I would lose my cock to this other man, this stronger man. My face seemed to deepen its already embarrassment-laden red hue.

I returned and showed him my cage. It was metal and fairly small. I always loved seeing men have to compress their cocks to fit it in, that was part of the turn-on for me. Their inferior cocks lost and as punishment I shrank them even smaller into the tiny cage. In that moment I almost felt sorry for what I had done. That thought quickly banished itself as instead I focused on how this was all going to affect me.

"That's a pretty gnarly looking cage. Here's mine, you pick." He was pretending to be nice, he was pretending that it was merciful. He was actually humiliating me further, making me choose my own torture device. I looked at his cage and immediately was struck with dread. It was bright pink. Bright, sissy, pink.

But it was bigger than mine. It had a wider ring for going around the balls, it had a longer and wider tube. In short, it'd be a lot more comfortable. Truth be told, I'm not sure that my cock could even fit into the tiny device I held in my hands. I may have lost the contest, but my cock was still a giant. My voice was almost a whisper, "I guess I'll take yours." Caleb smiled. He had the bigger cock, had made me suck it for almost an hour, had dumped a giant load in my throat, and was now imprisoning my cock inside his pink, chastity cage. I was truly defeated; I had never felt so vulnerable. I felt like my cock was shrinking inside me, like I was losing my manhood.

He didn't say a word, he maneuvered the device around me. I just stood there and let it happen, I put up no resistance. After a moment I looked down and instead of seeing my majestic manhood, I saw a frilly pink tube. It compressed my cock slightly, keeping it shorter than it normally would be while flaccid. Normally the tip hung even a little below my magnificent balls. Now, the tube kept me short, resting itself on my sack. He cupped my testicles "These are gonna be massive when I get back here. Now turn around."

I didn't know what he wanted but I did it anyway. I turned away from him and felt him put his hand on my back, pushing me over until I was bent at the waist. I felt his hands on either ass-cheek as he spread them open. He had a perfect view of my tiny hole, nearly virginal. I'd been an exclusive top for more than a decade. The last time someone had fucked me was when I was still experimenting in college, I always hated it. I hated opening up for someone else to enjoy. Now my asshole was fully on display for him. In my mind I wanted to resist, to fight him, to wrestle away the key and free myself. But I couldn't. I couldn't bring myself to oppose him, I knew that he had power over me, he was in control.