A gay story: So You Think You’re a Top? Ch. 01 I’ve been gay and out for 15 years. I came out in high school, and never looked back. Some of the kids did tease me. They’d call me “Phil… of dicks!” Which honestly just made me chuckle. I wasn’t especially big or imposing. Just about 5’10” and 160lbs. But no one tried to jump me or anything, and I mostly found their taunts lame, so I wasn’t bothered. Honestly, as a ginger, I was more used to those kinds of lame taunts so it barely registered.
I’ll tell you, in my time since coming out, I’ve tried a lot sexually. I was always very open to experimenting. It never bothered me if something I tried was considered emasculating to the average straight guy. In my experience, the average straight guy is well… a bore. So, no, I was no stranger to bottoming. And of course, it feels good. I viewed my many tristes where I bottomed as great experience for my true love: topping.
While both had undeniable physical pleasure, I got the additional wave of warm fuzzies when I manhandled a guy (or two). I’m not into spanking or that sort of thing. But I love repositioning a guy, pulling him by his waist where I want him to be, and telling him how good he made my dick feel. His moans of pleasure when I was pumping inside got my blood pumping, and my favorite part was after several positions, throwing him on his back, pushing his knees to his chest, and looking him in the eye while I bred him.
Cumming is great, but cumming in the hole of a guy as he pants and locks eyes with you? With that look in his eyes that tells you he’s allowed himself to be completely vulnerable to you? To your dick in his ass? Priceless. On the flip side (no pun intended), when I bottomed, I could never truly let myself go to the guy. It felt good, sure, but I also felt just so… exposed? It’s hard to explain. Regardless, it had been years since I last bottomed. My partner, Garret, and I had been together for 3 years and we had an open relationship. Things were going great. We got frisky a couple of times a week. And though we weren’t dating other people, we both had a few other guys we’d mess around with regularly, then go hit the bars with. It very casual, and it worked well for us. Still does.
As it happens Garret is a devious little bottom, and loves trying new things. So, when he heard from one of his fuckbuddies of an underground gay game show, he immediately asked me to check it out with him.
“It’s this Friday at that club downtown that we went to for my birthday. You remember the one,” he said. And of course, I did. It was one of those clubs that don’t have a sign, and the door is in an alley way. You only know of it if you get invited by someone who already knew about it. He showed me the flyer his friend texted. Apparently, it was called, “So you think you can bottom?!” I rolled my eyes at the cheesiness, and so did Garret.
We went, dressed in our hottest outfits. Figuring it would be a fun live show to watch. Garret was a bit smaller than me at 5’8″ and about 20lbs lighter than I was. He had on his favorite green jock, booty shorts, and a mesh tank top. His bleach blonde hair left messy rather than slicked back given he was hoping to get some action then or later. He looked so cute with his dark short-cropped beard. I was wearing some green chinos I’d gotten recently, and a black button down that I’d strategically left open to show off the orange hair on my chest. We figured we’d go, watch some explicit sex games, and maybe pick up a couple of guys to bring home. Instead, it was the start of a new journey for me.
I know it’s more fashionable to be late, but we got to the venue 20 minutes before the event was to start. And we both were grateful we did, because upon entering the alley door, we were greeted by a long line down the hall to the actual door of the club. The bouncer up front was checking everyone’s ID which wasn’t unusual. But he also had a clipboard. I was starting to worry this was a private party, and our names weren’t on the list.
“Don’t worry. Vinny took our names. So we should be on the list,” Garret whispered to me when he saw my visible confusion. Vinny was a nice guy. We’d hung out as a group a few times. Garret said he was an amazing top. He’d tried to get us to share him on more than one occasion. And Vinny himself seemed really into the idea. For one reason or another it just never lined up.
“Names?”
“I’m Garret, and this is Phil. Vinny should have put us on the list,” Garret said while we both handed him our IDs. The bouncer looked them over, checked against the clipboard, and passed us our IDs back.
“Great. Vinny is one of the guys running the show. He’s inside. Looks like he’s going to show you where to go and whatnot personally. Have fun,” the bouncer finished, and we walked inside.
“What does he mean show us where to go?” I asked Garret who simply shrugged.
Inside, I was surprised that it was a bit brighter than the club usually was. The stage was set up with a banner with the name of the show. There were a couple of slings, and a pair of sawhorses. In front of the stage was a folding table with a cheap red tablecloth thrown over it. A few guys were standing by the table, and had left stacks of paper, some equipment, and other things strewn across it, but they seemed to be cleaning up. Garret brightened up when he saw Vinny, whose eyes met ours and a smile slid across his face. He said something to whoever he was talking to and walked up to us. He was looking exceptionally sexy today standing at 6’2″, dark hair with some silver flecked in it, and similarly salt and pepper scruffy facial hair. He was wearing boots and his leather jacket which would have been warm for a club environment if he were not also completely shirtless under it.
“You made it! I’m glad. Welcome to the show!”
“Thanks, Vinny. I didn’t know you were running this whole thing,” Garret replied.
“Oh yeah, it’s been something I’ve been cooking up for a while. So did the doorman tell you what’s going on?”
“Not really,” I chimed in.
“Oh! Well, this is the first round of this little show I’m producing. It’s one-part game show, one-part socio-sexual experiment. The idea is we are going to have several contestants go through multiple rounds of competition for the next few weeks,” Vinny explained.
“Does the winner get declared best bottom or something?” Garret asked, clearly fishing for an invite.
“Truth-be-told, it’s not about finding the best bottom per se. It’s a bit different than some sort of… Olympics for bottoming if that’s what you were picturing.” Vinny smiled slyly at this. “Here’s how it works. We take a group of guys who are tops, and the competition is who can become the biggest submissive bottom slut over the course of the competition, or rather who can resist being converted into submissive bottom sluts…”
“What? For real? And the tops are into it?” asked Garret.
“Well, see that’s the thing. It’s kind of a challenge to the tops. There are two cash prizes. One for the guy who becomes the biggest sub slut. But to be honest, that is the runner-up prize. Sure, we’re happy for him, but maybe he was always a big sub slut in the first place, and this was just an excuse to act on it, you know? So that prize is $10k. Cold cash. But the grand prize, that’s what the tops are REALLY gunning for. And that goes to the guy, who can do the most subby sex stuff over the next few weeks, and then go right back to being a strict top. A guy who can take it like a champ, maybe even find some level of enjoyment, but can leave it behind when it’s done. That guy wins $50k. Also, in cold hard cash.”
“How do you figure out if he’s bluffing or not?” I asked given that is a lot of money on the line for this little competition to leave open for scammers.
“That’s the biggest challenge. We’ve devised a system, though. A system for the whole competition, really. To make sure we keep things honest. First, all the guys who are competing must agree to have their cocks locked. They’ll be locked the whole time as they won’t need their cocks for those weeks. We also pair them each with one of the judges. They’ll be their doms for the whole competition. Doms can award points for good sub behavior and remove points for slip ups. And once all the various competitions where the tops will get used every which way you can think of conclude in the first month, they’ll continue to be locked for another 60 days. In total its 90 days locked in a cock cage. The competitors are allowed to cum as much as they or their dom wants them to in that first 30 days with all the challenges.
Obviously, it won’t be from stroking their cocks, but from getting their prostates pummeled. But after the challenges are over, they aren’t allowed to cum at all. Any guy who claims to be solely a top, who can go through a month of bottom conditioning under the guidance of a top, and then wait out the remaining 60 days without begging to get fucked for a chance to cum can reasonably be considered a total top and will win.”
“Holy fuck. That’s so fucking hot,” said Garret and I nodded slack-jawed agreement. It sounded intense if you were going to compete, but for a chance at $50k, it seemed well worth it. Though, the thought of competing myself did not come to mind. “So, for the bottom slut runner-up prize, do they just have to get the most points from their doms?”
“It is a combination of most points awarded from their dom in the first 30 days, and most caged cumshots in the final 60 days. But one of the dom judges must be there to verify each of those cumshots. It’s basically a way to make it so that a guy who goes the first 30 days, and then succumbs to his newfound submissiveness still has a reason to stay in the competition. Just… by switching focuses,” Vinny said. His grin became more and more mischievous as he explained.
“Now you have me boned up,” Garret said. “I was kind of hoping it was more like the bottom Olympics and you would ask me to compete!” Garret laughed when he said this. “But this is honestly really hot. I’ll just be glad to watch.”
“I’m glad you think so too! If I’m honest, I did have an ulterior motive for inviting you. You see, right now we have five judges including myself. But we only have four contestants.” At this, Vinny shifted his gaze to meet mine in full. Garret watched this change in eye contact and followed his gaze to me.
“What? Are you asking me to compete?” I felt my face get flushed.
“Only if you’re comfortable with it. Though I will say, you are kind of my last hope. I had to make sure all the competitors were verified tops, you know? And no that doesn’t mean they’ve NEVER bottomed, but that I or one of the other judges felt confident that it really wasn’t their bag. At least not yet… Garret being such a bottom made me think you were a safe bet. I won’t pressure you, but I do need an answer pretty quickly since we start kicking things off in about an hour and a half…” Vinny said this rather nonchalantly, and though I understood he was in a bind with time, he truly didn’t make me feel pressured in the least.
“What happens if I say no? I don’t feel like you are directly pressuring me right now, but I might feel weird if my saying no ruins this whole thing for you…” I said rather sheepishly.
“Dude, it’s no problem. Each judge is responsible for bringing their own competitor. If you don’t want to do it, it just means I can’t be a judge. I can still be the host, and the competition can go on without me as a dom. And I promise I won’t be upset in the least. I already made peace with the fact that I’ll probably not get to participate as a judge this round. You are just a final attempt to see if I can join in the fun. I’ll let you two talk it over.” And with that Vinny walked back and continued his preparations.
For a minute Garret and I sat in silence, but I could tell from the look on Garret’s face, that the whole idea of this was turning him on a lot. “What do you think I should do, babe?” I asked him.
“I’ll be honest. The idea sound so fucking hot that I want to tell you to go for it. Not to mention it could win us a nice cash prize which wouldn’t suck. But I really only want you to do it if you are comfortable. Though, maybe I should tell Vinny you’ve already bottomed too much to be considered…”
“Oh HA HA. You are too funny,” I said and rolled my eyes. “We both know it’s been years since I’ve bottomed, so I am a bit nervous, but I do think that kind of puts me at an advantage. The other guys probably have never bottomed. Or only tried it once.”
“That’s true! And who knows, maybe you’ll become a huge bottom slut like me, and we can find a bunch of tops to share,” he said and stuck his tongue out at me. We both laughed.
“You know that means 60 days without my loads, though, right? Can you go that long?” I fired back.
“Wait, wouldn’t you be locked for 90 days?”
“True, but I only have to refrain from cumming in the last 60. Vinny didn’t say anything about restrictions on where I shoot my load or who licks it up in the first 30… ”
Garret’s face grew red as I had implanted the image of him catching the load getting fucked out of me. “Assuming I can cum from getting fucked. Never happened to me before.”
“Does that mean you are going to do it?” Garret asked, eyes glazed in a bit of lust. I thought for a moment and weighed the pros and cons once more. It sounded very difficult, but also exciting. And the reward if I won would be huge. Like down payment on a house huge. And though I wasn’t struggling, that seemed so far out of reach. Not to mention, I was sure that it would be a challenge, but I could do it. And if I did win, not only would I have the prize money, but I’d also know for sure that I’m not a top of convenience.
“I bet the first time I fuck you when this is all over will be earth-shattering,” I said by way of answer. Garret grew a smile from ear to ear. We went over to Vinny, and I told him I was in so long as I knew what the limits were. Vinny looked elated.
“Of course, dude! Here is a list of the limits. It’s a standard release. We have a strict no photography or videography rule during the live challenge nights, so you don’t have to worry about that. The rest is just that you consent to be part of the competition. This here is the clause that says you can back out at any time, no penalties, no hard feelings. It’s important for the integrity of the competition that you only stay in willingly. Here is a checklist of hard limits. The point of the bottom challenge is not to put you through the vilest shit we can think of. It’s just to get you submissive and slutty. So, anything you check off as hard limits here will be honored. No exceptions. Here is a list of safe words and non-verbal signal queues. If you use any of them at any time, everything will stop. And no, just saying a safe word doesn’t mean you leave the competition, so feel free to use it as much as you want. All participating judges, and tops are required to learn them all, and we’ve informed them ignorance to a safe word’s meaning is no excuse. If any of them violate those conditions, not only are they out, blacklisted from every club, and publicly shamed, but we’ll document everything and report them.” Vinny was taking me through all the ins and outs of the contract. The whole process made me feel more comfortable, and the transactional nature made me feel more confident. If this was going to be so clinical and transactional, I felt even more assured that I wouldn’t be swayed from my true calling as a top. At least not for long.
It was then as he was going through, and I checked off my limits that I realized just how close he was to me. He’d never avoided touching me or anything, but it was like a switch flipped when I said I would do it, and he was looking at me differently. He sat me down for some initials and my final signature at the table, and at one point he reached around me to pull my chair closer to him. “Sorry, it’s just a little loud in here,” he said with his face inches from mine. For a moment my heart fluttered a bit. He was honestly so good looking. Dark hair, a bit of stubble. He liked to wear industrial punk jewelry and had some very sexy tattoos.
And while before my comfort and confidence was steadily increasing, this was the first moment since the idea was proposed that I felt my self-assurance falter. I chalked it up to the initial adrenaline of agreeing to it dipping and tried to shake it off. I couldn’t help but notice that he smelled… really good. I checked some of my limits. Mostly around pain, and various excrement I wasn’t into. The form even gave me the option of safe or bare. My personal preference being to breed the bottoms I fucked. I’d never taken a load in my hole before, but since this was going to be an experience of firsts, and I got tested regularly and was on PreP, I selected bare.
“Now it looks like the fun really begins! You should go back to the green room. The show starts in about an hour so you’ll need to get fully… prepared.” And with a wink, he showed me the way to the back. I gave Garret a little squeeze, and he wished me luck.
“Try to let go, babe. I’ll be in the audience egging you on!” He gave me a peck on the cheek, and I walked into the green room. There were four other guys in there. Each in robes. They smiled and waved as I walked in and took the empty station. On the counter in front of a mirror was a towel with a douche (which I quickly excused myself to use in the green room’s bathroom), and when I returned I found a cock cage, a jockstrap in my size, and a robe on the chair like the other guys’. I put everything on besides the cage which I found to be without a lock.
“Don’t worry, dude. They said whichever judge is assigned as your dom will do the honors on stage,” said the handsome blonde closest to me. He looked to be in his mid-40s. Absolutely ripped, with a cropped haircut and clean shaved face. “I’m Mick. That’s Trent, Duane, and Niko. Looks like you’re the last addition!”
“Nice to meet you guys. I’m Phil. Sorry, I’m usually more personable but kind of feeling nervous.”
“No worries, we get it. Duane and I have been texting each other all our escapades trying to stretch our holes this week in preparation. We are both a bit nervous. I’ve bottomed before but a long time ago. Duane never has, though.”
“Damn. Not even to try it out before tonight? Isn’t this kind of… an extreme first time?” I said looking back at Duane. He was a tall and bearish black guy. He wore glasses and had a very cute smile.
“That’s what I told him! But he wouldn’t let me stretch him out!” Mick laughed. Duane finally tuned in to the conversation.
“Fuck off, Mick! Your cock is 9 inches and thick as fuck. I bet letting you be my first would be better for you, than for me!” Mick laughed again.
“Is this your first time bottoming then, Phil?”
“No, I’ve bottomed before. Just never got too into it. This was kind of sprung on me, though. So I’m a bit nervous since I didn’t even stretch and it’s been years since I last bottomed,” I replied. Mick stood up, and I saw his robe open for a moment. He wasn’t wearing his jock yet, so I got a full view and 9 inches seemed to be under-selling the monster he had between his legs. He started rubbing my shoulders a bit.
“Well, man. I wouldn’t mind helping you out. We have about 20 minutes or so before things start up…” He must have seen my eyes grow wide, and he laughed again. “Don’t worry, I don’t mean by fucking you. But I love eating ass, and I have a plug and some lube here. I can get you a bit stretched so you are more relaxed on stage. The tension I felt at the thought of him breaking me open with his monster faded with that. And his shoulder massage was doing the trick.
“If… if you don’t mind. I think that’d help,” I managed to murmur. He lifted me up to a standing position, pulled my chair out from behind me, and had me lean forward and bent over with my arms folded on the counter. He pushed my robe up so my ass was exposed and started gently massaging my cheeks. It felt great. Mick clearly knew what he was doing. After a bit of that, I felt him spread the cheeks, and the heat of his face as he leaned in close. The cold cheap countertop holding my arms up as I felt the first slow lick that started from my taint and slid along my crack, over my hole, and stopping just above it before reversing course. He started making slow circles along the muscled ring. For a moment the situation hit me as very surreal. Two hours ago I was going for a low stakes viewing of a sex show that I assumed had a small veneer of game show rolled into it with my bottom boy partner. Now I was having my ass ate by a competitor in a competition where we were trying to stay total tops while being subjected to sexual shenanigans designed to work us into a bottoming frenzy.
I audibly gasped when I felt his tongue push into me. For a minute I was sure this guy was some supernatural creature with the way his tongue kept pushing forward, and the width I felt of it pushing my anal cavity open.
“I think he likes it!” Teased Trent, who was the shortest of the group at 5′ 6″ and slender.
“Are you sure he’s not a bottom already?” Duane asked. I didn’t even look up or stop moaning, but I did raise one hand to flip them off, which only caused them all to crack up laughing. I even felt Mick’s lips get thin as he cracked a smile but did not stop making out with my hole. Someone knocked at the door, and walked in.
“Looks like you guys are getting acquainted! Good. I prefer friendly competition to the toxic kind. We get started in 5 minutes. Feel free to continue what you’re doing in the meantime.” I didn’t even look up to see who it was, but the voice was not familiar, so I assumed it wasn’t Vinny. Whoever it was walked out of the room.
Mick didn’t continue, though. Instead, he pulled back, and slowly I felt a rubber plug get pushed in the place of his tongue. I was surprised my hole offered no resistance except right at the widest part, but with a short yelp of surprise more than discomfort I felt it pop into place. “That ought to help loosen you up. Show time is in just a few minutes.”
At this it struck me that I wasn’t sure what the challenge would be. I remembered seeing the sex slings on stage, and the saw horses. I pulled myself into a standing position, as Mick kindly guided my chair back behind me. I sat gingerly on the plug as I felt it continue stretching me open.
“This may be a dumb question, but do you guys know what the challenge is for tonight? Or how this is going to go?” The four guys all smiled. One gave me shit for not asking enough questions when I was signing up. Trent is who spoke up first.
“I don’t mind telling you. First, they’ll introduce us as competitors. They’ll review the rules for the audience. Then we get assigned one of the judges to be our dom for the next 90 days. They told me they’d have us each draw a number, and the doms will draw a number. And the matching number is your dom. They’ll lock us all in our cages as we get paired up. Then going from lowest number to highest, the dom will pick a spot for each of us. All five spots are on stage. There are two slings, and two sawhorses. And one spot they just call the wild card spot. And we play a game.”
“What game is that?” I asked.
“Think of it kind of like… musical dicks,” Duane chimed in.
“I think musical fuck spots is more accurate,” added Trent. Before I had a chance to ask more questions, there was a knock on the door, and a guy entered telling us it was time to get started. We filed into a line and followed out up to the backstage area awaiting our entrance. Vinny was on the other side of the stage, and he smiled at me in my jock. With a wink he walked on stage.
“Thank you all for joining us! This took a lot of planning, and I want to thank the crew here, as well as all the other judges and especially our contestants for making this happen. So welcome to ‘So you think you can Bottom?!’ Though it’s probably more apt to call it, ‘So you think you are a top?!’ given what we have in store.” That got rousing applause and laugh from the group. “Tonight is the first night of a 3-month challenge. The goal? Well for the contestants it’s to prove who is the truest of tops among them. For us judges the goal is to make these tops, bottom sluts and release them to you all, our adoring fans. We’ll start by introducing the contestants who have all agreed to wear a cage for the next 3 months, subject themselves to our devious minds in a variety of bottom activities for the first month. Then, to endure the final 60 days locked without succumbing to the new bottoming urges we hope to implant in them with our cocks!” The crowd went a bit wild at that. Some whistles could be heard from various parts of the club.
“What happens tonight, Vinny?!” screamed some guy from the crowd.
“Well, tonight is the first event of the competition. I’ll explain the rules once we get to that part but suffice it to say that there’ll be some very tight holes being stretched! Let’s start by introducing our contestants!” And with that, he called us each out one at a time. He shared our name, asked us to confirm that we basically only top, and asked if we were confident that we’d remain tops, or if we were worried about becoming the insatiable bottoms he hoped we would be. My name was called last, and I heard Garret scream my name in support as I took the stage.
Here I was, standing next to four extremely sexy tops. All of us in jock straps. And each one holding a cock cage. After introductions had concluded, Vinny said it was time to assign us each a dom. My cock was rock hard, as I shifted by weight back and forth on my feet and felt the plug still in my ass continuing to stretch me.
“This evening, each of us judges pulled an envelope from a hat. In it is a number from 1 to 5. Now we will have each of you do the same.” Vinny explained and pulled a hat from the table in front of the stage where the other four judges sat. It was a bit hard to get a good look at them with the lights on me. We each took turns and then we all had envelopes. “Alright, all together, let’s open them.” We each opened them including the judges and found a card inside. I flipped mine over to find a number 3 inside. Vinny walked up to Trent who had a number 1 on his card. “Who had number 1 from our judges?” And a hand went up from behind the table. “Alright Trent, looks like your dom is Cameron!” And everyone had a round of hoots and applause. Then Duane raised his hand showing his card with the number 2. Vinny announced Duane as being matched with Carlos and another cheer. Taking my queue from Duane, I turned my card around to show the number 3. “Well, well, well…” started Vinny. “Look who drew lucky number 3,” he added, and turned his own card around to show a 3 as well. My heart fluttered again as it had when he got really close to me as I was signing up. There was a round of applause and I even heard Garret give a “Woo!”
Niko and Mick got paired with Liam and the aptly named Rod respectively. Though, it was hard to pay attention because from the moment I got paired with Vinny, he’d put his arm around my waist and pulled me close. He was fully clothed, yet here I was in a jock and had just agreed to let this guy be my dom for the next three months.
Afterwards we each took turns as our new doms put our cock cages on. We went in the same order as our numbers, and when it came time for me, Vinny asked one of the other judges to hold his mic and cards. He grabbed the cock cage I was holding gently, and to my surprise he got down on his knees to put it on. He kept glancing up at me as he grabbed hold of my cock and balls. Luckily the stage fright I felt had settled things down so he had no trouble as he slid it on ever so gently. When he glanced up, our eyes would meet and even though he was on his knees in front of me, I felt my face flush red as he snapped the cage into place and secured the lock. He took the key and slid it into his pocket as he rose to a standing position. That’s when I realized I had been holding my breath.
The rest of the opening ceremony went smoothly and quickly, and suddenly Vinny was back in host mode as he announced that we’d be playing a game. A game he said would make for a great way to open up the competition because it involved opening up our holes.
“We are going to play a game where we doms and judges will get the honor of breaking in our new bottom sluts. We’ll fuck to the tempo of the music. Starting slow. When the music stops, we all have to stop, and switch up who we are fucking. Then, the music keeps playing but faster. This will continue on for a few rounds until we are pummeling their asses.” Another round of cheers from the crowd. “At that point, we won’t be holding back. All five of our contestants are cool with getting bred, so here’s where the game really gets interesting. If you cum, you are out of the round. That goes for both us doms and the bottoms. Last bottom standing, wins the first round of the contest! The first point and a special opening prize! We’ll uncage them, and they can pick one of their fellow contestants to plant their last load before the cage goes back on for the rest of the game. A last hurrah of topping, so to speak… as long as all of our contestants agree.”
The room seemed to look to the five of us, and we all nodded in agreement. Truth be told, I’d love to plant a load in any of these other guys and given that this whole thing was sprung on me, and I didn’t have a chance to fuck a last load into Garret, I figured this would be a great prize. Though, the thought did also strike me that I’d probably be at a disadvantage being the only one who didn’t know ahead of time that I’d be competing. Let’s hope these other guys shoot before me then, though I had my doubts.
“Without further delay, let’s get everyone in place!” Vinny sounded very commanding when he said so, and that’s when I remembered there were only four spots on the stage. Two slings, two sawhorses, and no one had explained this mysterious fifth wild card spot yet. Going from first to fifth in order of which card we drew, each dom picked a spot for their new sub. Cameron told slender top Trent to swing his leg over one of the sawhorses and get in position, which he did quickly, showing a beautiful ass and hole to the crowd. Carlos walked over to one of the slings and patted it while looking at Duane, who smiled shyly and similarly hopped in. Then I turned to Vinny as it was my turn. He smiled a completely evil but extremely sexy grin. “For you, Phil, I’m going to put you in the wild-card space.” Everyone clapped and hooted. And before I had a chance to ask what it was, I saw some guys parting the crowd, and someone turned on a spotlight. The stage techs were wheeling in what looked like a leather chaise longue. It had slopes on each side, and it was situated in the crowd, though with quick access to the stage for when we’d do the switch presumably.
Liam asked Vinny loudly what makes it a wild card space, and Vinny explained to the crowd that each dom gets to tell the bottom in the wild card space their preferred position. And to make it extra wild, he wanted the crowd to be able to really see the action, hence the placement. He clapped a hand on my shoulder and walked me over to the spot. I turned to him and sheepishly made eye contact, about to ask how he wanted me. Before I could, he leaned in real close and whispered in my ear that he wanted me doggie style.
“I want to show everyone your hole getting stretched by my cock for the first time, Phil,” and I shuddered at his words, and immediately hopped up on all fours, and presented my hole to the crowd who screamed their approval. I saw Garret swing around to my right, and lean in.
“This is so fucking hot, babe. I want to watch your face when he enters you… is this all still cool?” Garret asked with eyes that showed a mix of absolute lust, and also still that sweetness that I fell in love with. I smiled and nodded. I was surprised how easy this all was feeling. He smiled widely.
The last two doms and subs took their spots, though my heart was pounding too hard in my ears, and the sounds of the crowd all around me made it hard to pay attention to any of that. I turned my head back and watched as Vinny stripped off his clothes. He was very sexy. A strong chest, and a bit of a dad bod. A small patch of dark hair leading from his belly button down to the base of his cock. This was the first look I got at it. It was thick. Very thick, and probably about 7 inches long. The head was the biggest part by far. A textbook example of a mushroom tip. It stood straight out, pointing at my hole. Vinny gently patted and pushed on the plug still in me with a smile. He gently slid it out, and I gasped as it popped past my ring.
“Everyone,” Vinny started. “Count down for our dj to get us started! 5!”
And everyone took up the chant afterwards.
“4! 3! 2! 1!” And with a huge applause the music started, and I felt the head of Vinny’s cock at the entrance of my ass. He started pushing in, and I focused my breathing and on relaxing my hole. Garret leaned in and whispered how good I was doing as Vinny pressed deeper and deeper until I felt the initial plunge of his head past my anal ring. It felt much much bigger than the plug, but I was grateful I’d done some warm up.
In truth, the first few minutes were painful, but I knew that would be temporary. It wasn’t the pain of something going wrong, just of a muscle that had not been stretched in a while. He had lubed up quite well before he started, and when I felt his pubes brush up against my crack I felt the fullness of a cock that I hadn’t felt in a long while. At this point, the pain started to dissipate and it began to feel alright. He didn’t start pumping right away. Left it there for me. Which was good as he was so thick. For a minute, though it was starting to feel good, the sensations of the crowd around me, my nakedness, and this huge cock burying its way into my tight hole became a bit of an overload. My brain started to panic ever so slightly. I was starting to think what am I doing? Why did I agree to this? It didn’t feel bad but it was all so much, and my breathing started to pick up. I felt my hole begin to tense, not relax around his cock.
And just when the feeling was starting to build to the point where I thought I might have to end this whole thing before I even started, I felt his chest make contact with my back. He leaned over me, and I felt the scruff of his cheek and jaw graze my neck and ear.
“Your hole feels so fucking amazing, Phil. You are doing such a good job at taking my cock. I know its thick and your ass isn’t used to taking it, but you are such a champ. I’m glad I got paired with you out of the rest of the group…” and his whispers of praise and encouragement made me instantly feel like melting. My tension faded and I felt my hole begin to really relax. Only then did he start pumping. And now I was experiencing firsthand what Garret meant when he told me that Vinny really knew what he was doing. He kept his face right next to my ear while he started sliding out of my ass ever so gently. “I bet you will crush these guys. I bet you are going to win every contest. And even if you win the whole thing and prove you are a top, I’ll be dreaming of plowing this hole again.” His words were making me so relaxed, and I felt a wave of pleasure from his slow thrusts.
“Thank you, Vinny. For the next 90 days its yours…” I managed to pant whisper back to him. He chuckled.
“See, the way I see it, this hole will always be mine. Either it’s mine for the next 90 days, and you return to being a strict top. In which case, it will always be my hole above all other tops. Or we awaken the slut within, and if that happens, there’s no way I’ll give this thing up unless you ask me to. I always honor my subs wishes. The thing is,” and I felt his pace pick up slowly through all of his words. And he paused before finishing this sentence for one hard thrust where the first smack of his hips into my ass reverberated throughout the club, and his cock head pushed deeper than anything had ever been inside. I yelped a moan of pleasure. “The thing is my subs tend to wish for one thing and one thing only…. Do you know what it is?”
And I did. I knew in that moment exactly what it was. I nodded. He smiled in response.
“Tell me what it is, Phil.”
“Y- your cock, Vinny?”
“That’s right. And what about you? Do you want my cock?” His thrusts were now fully in time with the music, which was certainly not the highest tempo song, but far from a slow song or heartfelt ballad. My hole was really opening up to him as he whispered these words in my ear, and I knew what answer he wanted. And I knew it was the truth in that moment. I was really feeling waves of warm pleasure with each time his cock bottomed out inside me. “You there, Phil? You gonna answer me?” he chided.
“Y-yes… I wan- want your cock, Vinny,” I said.
“Call me, sir,” he whispered back.
“Yes, sir…”
“Yes, sir, what?”
“Yes, sir. I want your, cock, sir.”
“Good boy, Phil. That’s exactly what I wanted to hear,” and he thrust even harder. Not faster, but with more of his body’s weight behind it, and I moaned loudly. A cheer went through the crowd. I felt my cock leak what felt like a full jet of precum into my jock with that thrust. He continued at the same pace, and I moaned for each thrust after that. Whimpering like I was in heat. My eyes fully closed. I could hear everyone around me, but it faded away in a sense, and all I focused on was the cock inside me.
Until I heard the music fade, and Vinny slid out of my hole. “What do we say, Phil?”
“Thank you, sir,” I managed to pant out. My whole body felt electric, and I felt as though I were in a daze while he switched to the next dom, Cameron.” I hadn’t gotten a good look at him, but I felt his presence.
“Okay there, slut. Looks like it’s my turn to have a go at your ass. Why don’t we show this nice crowd your pretty face as you take my cock,” and I felt his hands on my hips as he turned me around so my ass was facing the stage. He waved his cock in my face. “That’s good, slut. Take a look at this. Its going up inside you.” I pulled my head back a bit to get a better look and found it to be a bit shorter than Vinny’s. It also didn’t have as big of a difference in size between the head and the shaft, but that was because it was very thick. And he must have seen my eyes go wide at its girth. I looked up at him and saw he was probably about 40. He had huge pecs, and a bit of a beer belly, but as close as I was I could tell it was fairly solid. His head was shaved, and he had a thick brown-grey beard. “Don’t worry, slut. I’ll slide in real slow… at first.”
And he walked around to the back of the leather chaise longue.
I looked over at the crowd and saw lots of guys smiling and even a few of them stroking bulges. I felt Cameron’s hands rubbing my cheeks and spreading them apart. He drizzled some lube over my freshly fucked hole and slathered more on his cock. He slid the head up and down the crack until it found my hole. Once it did, it pushed in. It popped in much easier than Vinny’s had… at first. Then I really started to feel him stretching my hole as it slid deeper and deeper. I made eye contact with members of the crowd as I felt my jaw gently pop open with the additional pressure.
The music just started up again, and when I felt Cameron’s pubes on my ass, this time there wasn’t much of a pause before he started pumping. Clearly he was trying to get back to the rhythm he’d be at fucking Trent. And while it was a tight fit at first, slowly but surely my hole loosened around his thick cock.
Cameron was more interested in putting on a show than Vinny had been, as I saw his shadow doing things like flexing while he pumped in and out of my ass. And the angle he was hitting was perfect for pushing on my prostate. I felt down at the pouch of my jock strap to find a sizeable wet spot of precum was forming. The next song started and his pace increased and he was really working up a good rhythm. I felt some sweat rolling off his body and landing on the small of my back. Some of the guys in the crowd were full on stroking with their cocks out watching my face make funny shapes with each thrust. My hole was keeping up with the pumping dick in it very well and I started feeling a boost of confidence. I was taking my second cock of the night and it was feeling good. Cameron was moaning out loud and getting the crowd wild, and I couldn’t help but grunt with each slap of his balls on my taint.
Before I knew it, the music again faded, and Cameron slid out of my hole. Gave my ass a light smack and said, “Hot damn that is a nice tight ass. I hope I get more chances at it. I’ll have to ask Vinny if he’ll let me get more soon.” With that he stepped away, and was replaced by Carlos. This was my first moment to get a good look at him. Probably in his mid 30s, he had long dark hair, and a bit of a mustache and some stubble on his chin. He was stockier than Cameron had been, and bit chubbier. He was very sexy with some tattoos on his arms and an eyebrow piercing. He told me to lie on my back with my head towards the crowd. My ass sat up on the incline so he could get a good downward angle, and my head was ever so slightly off the edge.
From the angle I was able to watch his cock as it approached my hole and he had me pull my caged cock covered in the wet pouch of my jock towards my navel so folks could really see him enter me. He was uncut, and his cock was the smallest so far but by no means tiny. It was about 6.5 inches and decently thick. His balls were huge though, and when he slid into me (the easiest yet), I felt them resting on my taint like two heavy golf balls. Within 60 seconds of Cameron pulling out I was not being fucked again by my third cock of the night. The music started up again and he was already matching Cameron’s pace from before. He didn’t even seem tired as he clearly had a lot of stamina. I underestimated how hot it would be to see a bunch of leering faces looking down on me upside down as they watched me take another dick and stroked themselves. I made eye contact with Garret who was looking down at me with an insane amount of lust. He too was stroking his cock and had it popped out of the band of his shorts. I also watched him eyeing some of the guys who were stroking watching me. I waved at him to come closer, and he stepped towards me and leaned in.
“Everything okay, babe?” he asked with concern.
“Honestly, yes, this is fucking hot. I wasn’t expecting to be so turned on,” I managed to whisper back in between thrusts and moans.
“Fuck yeah, babe. Its got me so turned on. I might start sucking off these guys stroking as I they watch you get railed,” he whispered in a lusty way that indicated he was checking with me for if that was okay.
“Do it, babe! Would be hot watching you throat some cock from this angle…” and with that he pulled back and gave me a big sloppy kiss before pulling away and immediately moving over to one of the guys to ask if he can suck them off. They happily nodded, and I watched him kneel down. And just as I watched Garret swallow this cock in one fluid motion, the next song came on and the tempo took a steep incline. Suddenly my hole which had been fully relaxed was now being pushed to a new stretch limit. It wasn’t pain, but it occurred to me that this was full speed for Carlos and the two that came before hadn’t managed to get up to that same level of intense thrusting. The DJ confirmed that this was the fastest tempo so that the tops should stop holding back their loads if they were, and for us bottoms to brace for some true pummeling. I reminded myself that I should try to hold back my load.
The angle was hitting my prostate with each thrust and with less of a break between impacts. It suddenly felt like my cock was building up. Like I was going to wet myself. The dark spot in my jock that was collecting my precum was apparent, and Carlos reached down and while making eye contact and smiling widely, pulled the pouch back so my caged cock was now resting on top of it. Slipped a few fingers in the pouch, and came back with his fingers slick with my precum before jamming them in my mouth. The salty taste was amazing and I found myself eagerly sucking my own precum off his fingers as his thighs slapped against mine. I saw the look in his face and realized that it had become a situation where one of us was going to blow. But would it be him or me first? If it was him, I might hold out longer by getting a break while waiting for another switch of the tops. His eyes were locked with mine and he was muttering to himself. His huge balls which had started loose and resting were pulled back tight, and my cock was spurting jets of precum as the feeling of my orgasm was ready to erupt. I was both feeling the amazing feeling of an anal orgasm on the cusp of blowing and regret for not fucking a load into Garret before we left. I was worrying I would be the first one out when Carlos bucked his hips into me and thrust as far in as he could as his eyes snapped shut and I felt the pulse of his cock as it emptied his huge balls into my hole. For a second I thought I was still about to cum but the feeling died down.
The DJ jumped on the mic and said, “Looks like we have our first eliminations! Carlos and Cameron just unloaded into Phil and Mick! As for our bottoms, Duane is our first one to shoot his load even caged!” The room erupted into a huge applause. Carlos pulled his now softening cock from my hole and I felt a small dribble of cum escape with it, but my hole snapped shut to hold the rest in. He gave me a light smack on the ass and thanked me for taking his load.
At this juncture it became apparent there was a balance issue, though. There were four bottoms still in, but only three tops. Luckily though, the music hadn’t stopped just because some of the contestants shot their loads, and just as folks seemed unsure what would happen, a groan escaped Trent who had been taking Liam’s cock the likes of which I’d heard plenty of times from twinks taking dick and cumming hands free. And even caged as he was, just like Duane, he shot his load down towards Liam’s cock that was still sliding in and out. The angle of the cage had directed the load there and I caught a glimpse of cum just above the thick member Liam had been using to impale Trent with.
Now we were back to even numbers, and the DJ called for the guys to switch places. Liam pulled out and scooped up a healthy amount of Trent’s seed. He started walking over to me and I watched him stroke his cock and coat it in the cum he just fucked out of the skinny top before me. He was the tallest of all the tops at 6′ 7″. Tall and lanky, with hands like baseball mits, and feet that probably required custom sized shoes. He told me to flip around, put my feet on the ground, and straddle the leather chaise longue. I watched him walk around back to my hole and his cock was at eye level. It was probably the least thick cock of all the guys, but it was 8 inches and it curved up right at the end. No wonder Trent had shot his load getting this thing to reach deep in his hole. I was worried I wouldn’t last long, but was glad I wasn’t the first out at least. I felt him slide his cock up and down my crack looking for the hole and as soon as he found it he popped right in from the stretching I had gotten before him. I felt Trent’s cum a bit thicker than all the lube had been previously. With a short pause after the head popped in, he grabbed my hips adjusted his own stance and then as the music started thrust in all the way until I felt his head at my second hole. For a second I thought he might just punch through that too, but he didn’t.
Instead, he’d thrust to the tempo and when his head bumped up against it, he moved his hips and I felt it rub around the ring of it. He had quite a lot of finesse with his cock and I relaxed further realizing he knew just how to work something so long. It didn’t take long for him to pop through that second ring and without any pain. Just a gasp from me. And I realized I was right to be worried that he could coax a load from me with ease. Because even as I was relieved that I got a break after nearly shooting my load with Carlos, I was right back to feeling that load getting ready to erupt. Liam was sliding off my prostate with each stroke and in this position I felt my belly getting slippery on the leather as a thick coat of precum came between them.
What I couldn’t tell from where I was, though, was that Vinny was giving Nico a fuck like nothing else, and Liam here was feeling the tightness of my second hole on his cock head in just the right way. Just as I was sure I was done for in this competition Liam slammed his hips into me, and his cock as deep as it could possibly get and I felt the unmistakable feeling of his cock throbbing another load into me. The second one shot directly inside, and the third one to coat my insides if you could the load he used as lube. He grunted and I felt his muscles tense all over as he became a solid wall of muscle. Meanwhile Vinny did what he does best according to Garret and Nico was now shooting a load all over his stomach as he hung in the sling with his caged cock straining.
Suddenly there were two tops and two bottoms left. Vinny and Rod for the tops, and Mick and myself for the bottoms. Everyone in the crowd was hooting and hollering. And after slowly slipping his cock from my hole, Liam took a seat with the other eliminated fuckers. Vinny walked over to Rod and they whispered to each other. Vinny walked over to the DJ and whispered some more. Finally the DJ clued us all in to what they were talking about.
“Looks like we are in the final rounds of tonight’s contest, everyone. Let’s get Mick and our late entry Phil into the slings for this last part. And Vinny was there by my side helping me up and walking me over to the sling. He brought me to one that still felt slick with sweat and now I was sitting in it next to Mick. Vinny leaned into my ear.
“Great work so far. I’m impressed! I’m hoping you can hold out because its Rod’s turn at that hole and he is the most hung of all the guys… well all the tops anyway.” And I saw that he was right. Rod had a cock that was longer than 8.5″ and just shy of the full 9″ that Mick was sporting. And it was as thick around as Cameron’s had been. Easily the biggest cock I’d have ever taken. “Don’t worry, though, slut. You’ve got some nice sized loads in your hole so I am sure you can take it.” And he patted my shoulder and I felt that warm fuzzy feeling I’d had earlier with him. “Be a good slut and even if you lose, I’m sure I can find a way to reward you for your hard work…” and he winked before he and Rod switched places. Rod was probably in his 50s. His hair was white, but full, and cropped tight. He clearly worked out a lot. He was positively ripped. I didn’t know him before tonight but if you told me he was a body builder I’d believe you. He smiled while he coated his huge tool in more lube. I felt it at the entrance of my hole as the music started up again.
He started pushing in at a relentless pace. It wasn’t a single instant thrust. But the pressure he applied was smooth and constant and within 30 seconds, and with his hand on my mouth to muffle my yelp he was balls deep inside me. He removed his hand from my mouth, put both of them under my knees, and winked at me before he started pile driving me. I was whimpering like every bottom slut I’d ever fucked into a frenzy with each and every thrust. I could feel my face flushed red, and my body was coated in sweat. “Good little faggot,” he said. I had never been called little before but clearly to Rod, everyone was little when compared to him. I turned to my side to watch as Vinny was railing Mick just as hard. Clearly angling his cock to hit Mick’s prostate and Rod looked over and got inspired to do the same. He was angling it just right and with each impact I squealed.
It became apparent that all four of us were getting LOUD. Moaning, whimpering, yelping. The sounds of slapping skin was echoing in the club. Neither Vinny, nor Rod were holding back and both began to grunt the telltale grunts of tops about to breed the bottoms enveloping their huge cocks. Mick and I were both drooling and jabbering messes as no intelligible words escaped us and I felt my load and my balls drawing back for the biggest orgasm of my life. Mick began to get higher and higher pitched as Vinny railed him. It would be neck-and-neck. And as though they were synchronized fuckers, Rod and Vinny slammed into me and Mick with force and I felt the throbbing pulses of my fourth load in my hole. It was enough to drive me over the edge and that last slam pushed the button and I was cumming. Huge streams of cum from my cock. The first shot hit Rod’s belly, and he grabbed my caged cock and angled it back. After that, the next shot hit my forehead, then my chin, then back up to my mouth and nose. I caught my own cum in my mouth.
It took me a moment to stop seeing stars as the music faded out. Rod slowly slid his dick from my well used hole. “Damn you are one hot fuck. I gave you a huge load and I can see it dripping out of you…” he shoved a finger up inside me, swirled it around, pulled it out slick with the four loads that had been deposited inside me and stuck it in my mouth. I found myself sucking on it. I looked over at Vinny who was still deep inside Mick having just deposited the load in him. And while I was still in my post-nut glow I felt a pang of jealousy that Vinny hadn’t gotten to shoot his load in me. That’s about when I remembered the contest and realized I wasn’t sure if Mick or I had cum at the same time. Vinny slid out of Mick, walked over to me and saw the huge load all over my stomach. He grinned. Not in the way I had hoped though. It was not the grin of someone who had picked the winning horse. He walked over to the DJ booth grabbed a towel from a stack and wiped sweat from his forehead before grabbing a mic.
“It looks like tonight’s winner is decided… after a rousing fuck fest the last man standing who hasn’t shot a load is our friend Mick!” Everyone cheered. I was happy for him for winning, but I’m a competitive person so I won’t lie and pretend I wasn’t disappointed. How Mick had managed to hold off shooting was beyond me. “Great effort from our runner up, my very own newly minted bottom slut, Phil!” And folks cheered as well. Rod helped me out of the sling before going to help Mick. “Now let’s line up our doms and contestants…”
In just a few moments we were all standing side by side on stage. I felt the loads starting to drip down my thigh. Vinny stood next to me, he put his arm around my waist and pulled me in close. And all over again I felt those butterflies. Which were only even more exasperated by him leaning in whispering how proud he was of me, how he was sure I’d win future games, and how fucking hot it was that I had the most loads up my hole. I smiled shyly and averted my eyes from the crowd. I could tell I was blushing.
“Mick! Mick! Mick! Mick!” came shouted out from the folks in the crowd. He took a bow and I could see that his giant cock was still straining in the cage.
“Alright Mick! As our winner, you get to close out the game tonight. You won the first special prize of the contest. You can pick from all the eliminated guys you are competing against to plant your own last load before we lock your cock back up for the rest of the competition. Vinny handed Mick the mic.
“Well, I thought long and hard and though I’d love to plant a load in each of you-” someone screamed their approval of this idea and the group laughed. “Since I can only pick one, I think I’ll pick the guy who I actually helped get properly stretched before the game backstage…” Oh fuck, I thought. I realized who he meant. “So, would our runner up for the evening do me the honor of taking my big fat cock?” And he turned towards me. The room exploded in cheers and applause. To be honest I was a little taken aback at first. But then I thought about it. First, it was fair given that it would have been a lot less fun had he not eaten my hole out and popped a plug in me. Secondly, I got a warm wave of feeling like it was intended as a show of respect. And my competitive nature took it as a challenge. I’d just taken more dick than I probably ever had. And I couldn’t think of a better way to gradually size up on cocks in a single evening than to have taken the dicks I had in the order I had. I turned towards Vinny. He had the biggest smile plastered on his face, and he leaned in.
“Go on, boy. Make your new Sir proud of that hole…” and that was the last bit of encouragement I needed. I turned back towards Mick and smiled shyly but nodded my head. The group of guys had been quiet waiting for my reply and all applauded loudly at my agreement.
Mick replied, “Is that a yes?” in a very sarcastic tone. I rolled my eyes.
“Yes, I’m game. Only fair to pay you back for your assistance in getting ready.”
“Hmm… Vin. You are going to have to train this one a bit better…” he said with a mischievous expression. Vinny grabbed one of my cheeks and squeezed. Our eyes met and he seemed to telepathically tell me what Mick was getting at. I felt my face flush again.
“Uhm… well Mick… would you please plant your load in my hole?” And the guys went wild again.
Mick smiled widely. “I’m happy to oblige a blossoming slut! Now why don’t you find your way back to the wild card space… I think the crowd would like a close-up look at the final breeding of the night…”