The situation was rather surreal. It didn't dawn on me until that moment listening to the man step up to the gloryhole that I went from swallowing my first load ever through a glory hole to planning the logistics of how I was going to make sure this guy's load ended up on my face. All while my caged cock was throbbing within its enclosure, and my heart was racing from the approval I'd received from Vinny.
Not that I was a stranger to gloryholes. It is more that I was accustomed to sticking my dick through one rather than servicing the dick that came through. I had entered this contest knowing I'd have to be open to take a LOT of dick. I was competing against four other men who all also identified as total tops. Yet, we all agreed to cage our cocks for weeks of bottom debauchery. In those first few weeks, we were encouraged to shoot as many loads as we wanted if our bodies so desired while being impaled on dick. But once the first month was over, we would have to endure 60 more days locked where we won't be asked to do anything slutty. Instead, we will have to resist the insidious temptation to beg a guy to fuck our loads out of us. The guy who can refrain from being fucked silly just to get his rocks off wins a huge cash prize. And in the first month there is competitions to award points for being extra slutty and cock hungry.
The points had a dual purpose. In the event more than one guy manages to remain a total top by patiently waiting out the final two months, then the points exist to break a tie. The guy who got the most points the first 30 days AND who refrains from begging for a prostate orgasm will win. In the event more than one guy drops out in that final 60 days, though. Well, then they have the option of pursuing even more points with additional slutty challenges. The guy who fails to stay a total top but gets the most points being a bottom will get the consolation prize. Another cash prize not nearly as big as first prize, but still well worth it.
In our inaugural challenge I came second... well I came second-to-last in a live sex show version of musical chairs where my hole was the chair, and the dicks were... never mind I think you get where I'm going. Having been the second-to-last contestant to shoot my load, the man who beat me decided to claim the first place points and as an added treat he got to uncage himself and fuck me silly. Which all adds up to not as many points gathered by yours truly as loads. But my personal dom and judge for the contest, a top named Vinny who liked fucking my bottom boyfriend Garret, assigned me some points the following couple of days after the first night while he trained my mouth and hole for the next challenge: a gangbang with all the judges participating.
If that wasn't nerve-racking enough, an anonymous benefactor donating his personal private gloryhole space for extra credit work added to the anxiety. We can't all get gangbanged at the same time if the five judges were doing the banging. Knowing I wasn't terribly ahead in points did give me a reason to take up this extra credit assignment. After all, the guy with the most gloryhole loads by the end of this week would get 100 points. Though I was competitive, my conflicted feelings about going from exclusively topping to trying to score as many loads as possible at the gloryhole was not exactly an easy choice.
No I nearly passed, but Vinny caught me as I fucked up some of his rules for being his sub and gave me a choice at my punishment. Well a choice in what he called each punishment which he described only with a vaguely coded phrase. My punishment was no access to Vinny's dick. And given my heightened state of arousal, how Vinny got my stomach fluttering in a way no other top ever has, and the fact that without his dick I would automatically be disqualified for this week's gangbang challenge and forfeit another week of points, it was my bright idea to set myself a challenge. Vinny agreed to it. If I could get ten loads at the gloryhole before it was time for my gangbang, he'd rescind his punishment and dick me along with the other doms.
Yes, you heard that right. I -- a self-described total top -- am currently caged, on my knees in a decked out gloryhole, with a load in my stomach, and the makings of a plan to get the next one on my face, need to extract nine other loads if I don't want to be benched this week in the taking dick challenge. You know what they say: gotta take dick to take dick? Pretend that made sense.
There I was though, watching as another dick slid through in front of me. This one wasn't as long as the one previously. It was rather average, but uncut. Now as I'd already mentioned I've sucked plenty of dick. And I've gone to plenty of gloryholes. I'd just never sucked dick at a gloryhole, and I was still wrapping my head around the fact that my first one had gotten me all sorts of hot and bothered. Even more so when Vinny messaged me his approval. This guy had a bit of a bush too that was poking through the hole. I reached up and grasped it, sliding my hand down toward the base and gently pulling his foreskin down the head.
It was glistening a little. His foreskin had clearly trapped a bit of his precum. I swiped my tongue across the head and tasted it. This guy's was very sweet. Moreso than the previous dick had produced. I heard him moan through the wall. Figuring the dick wasn't going to suck itself, and that I still had several loads to go, I stopped wasting time. My lips parted and I tongued the head of his dick as I slid it into my mouth. I let my hand rest at the base of his cock. That way I could have a bit of control over the skin. This turned out to be smart as I noticed his foreskin came with my mouth a bit as I began to pull off him.
It took a bit to establish a rhythm, but I soon found myself bobbing up and down and adjusting the pressure and placement of my hand on his shaft to alternate whether my mouth was sliding over his head, or his own foreskin. His dick was slick with my spit, but I could tell he was leaking more precum as little throbs and pulses produced more of that sweet taste of his precum. His dick invading further and further into my mouth and throat as I gained momentum. My other hand reaching up and tugging at his balls as I hoovered his cock. I felt them draw further and further up towards his abdomen and his breathing pace became more ragged. He wasn't going to last long. And just as I had that thought, I heard him whisper.
"U-I'm gonna c-cummm," he said. He was so quiet that I think he was worried I didn't hear him. "I'm cumming now." He said this more forcefully. If my mouth wasn't engaged at slobbering on his dick already, I would have laughed a bit at his polite tone. But this was what I'd been waiting for. I pulled off his dick and lined the head up just in time for the first shot of cum to fire from his dick. Then came several more shots, just as powerful as the first. It coated my nose, my right eyebrow, my right eye (which I closed tight but still felt the sting of salt anyway). One shot got right into my slightly ajar mouth. His cum as it happens tasted even sweeter than the precum had. And his last bit of load dribbled out on my chin. I was well and truly plastered. I nursed the head of his dick for the last few drops. He was clearly sensitive because I heard him jerking to the sensation on the other side of the wall. Then as unceremoniously as he began, he slipped his dick out of the hole. I peeked a little and watched him pull his pants back on and leave in a hurry.
To be honest, I was a bit pleased with my performance. I'd managed to suck that guy off in a few minutes flat. I snapped a pic of my plastered face and sent it to Vinny. He replied instantly telling me I was a good slut and reminding me that he wants me to keep that load on my face until I'm done, and he expects a pic of me when I'm done to prove I did what he asked. Though he did say I could clean my eye before it dried shut. What a gentleman. Two down.
The next forty minutes saw two more dicks. One average like the second one, and one below average. Vinny gave me no stipulations, but did tell me I was a good slut when I mentioned swallowing them both. My face was still covered in cum, though it was dry and flaky. My knees and jaw were a bit sore. But I felt good about the pace. That is until we hit this unexpected lull. Thirty minutes passed and I just sat watching porn and starting to feel a bit self-concious. Four men had used my mouth to cum, and I didn't know the first thing about them. Well, I guess I knew they had dicks, which in the context of this whole challenge would be the first thing of note. It was the second, third, fourth... you get the picture. Those are things I knew nothing about. I didn't know their names, ages, anything. I only knew them by their dicks, and the taste of their loads.