So You Thin You're a Top?

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.