Boy Zoo Story Ch. 07

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A challenging contest on the first stop of the night.
2.4k words
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Part 7 of the 8 part series

Updated 07/19/2023
Created 02/25/2023
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My story and originally published elsewhere. All characters are of legal age.

Perhaps a reminder is in order: the first chapter explains that all boys can leave any time they like. Hence, all activities described are consensual.

*****

I follow them on their leash and on all fours. My tiny skirt is not enough to hide the plug in my ass or my chastity cage. Part of me is surprised that after all that I have experienced here, I would still be self-conscious about showing off a plugged boy pussy and locked dick like this. As I notice men looking and commenting on 'this cute leashed sissy bitch', I blush however.

I wonder where they will take me. There must be so many exciting places and rooms here!

FIRST STOP

They stop me in front of a room. I hear boys moaning and whimpering behind the door and my cage feels just a little smaller as a result. I kneel by Master Miguel's side, as Master Jacob fishes out a blindfold. Clearly, they want what's coming next to be a surprise. Once I was properly blindfolded, they opened the door and led me in. I could now hear all the moaning much louder, and there were boys apologizing 'I'm sorry, Sir! It's just too big' or 'I will do better next time, Sir!'. Others were just begging 'Please Sir! It hurts!' or 'I cannot take it anymore, Sir!' Some boys were weeping, others bawling.

There were also men commenting positively on the performance of some of the other boys. Others were reminding boys: 'All the way, boy!'

All the sounds made me nervous. Whatever's going on is this room is intense that much is certain. My Masters lead me through the room. They stop and chat with another master.

- "Do you want your boy to take on ours?"

- "Sounds like fun. Just a warning, though: mine's a pro. Does yours have experience with this game?"

- "No idea, this is the first time we spend extensive time with him."

- "He's cute. Hopefully you won't have to punish him too brutally when my boy inevitably beats him..."

I still don't know what the game is that I am now apparently committed to, but it sounds like it will be hard. And, it doesn't sound like I have much of a chance of winning.

One of my masters squats next to me and holds my shoulder. It's Master M telling me: "Before we take off your blindfold, we just want you to know that there's no shame in losing but, there will be punishment. This will be when you decide what happens this evening and night. Win, and you'll still suffer and hurt, but there'll also be some fun to be had. Lose, and this will be a night of endless and relentless torture."

I knew coming here tonight that pain and torture were always in the cards. However, I have a chance to make sure that there will be more than that I just don't know yet how I'll be able to do that. He takes off my blindfold, and there it is! I can now see what's going to determine my fate for the evening: I see a room packed with long benches full of dildos. The dildos are attached to the benches from smallest but not exactly small to biggest or rather, freakishly large. Here and there, there are boys racing against each other. They take the first few dildos with ease, but the last few are unsurprisingly a challenge. Some boys just have to give up in tears -- that's not going to be me, I promise myself -- because they just cannot impale themselves on the largest dildos. Others just keep trying, even though they are clearly in agony. Some real sluts take the huge rubber dongs still with ease.

There are also boys strung up against the wall. They are hanging from a crucifix with only their arm muscles to keep themselves up. Their boy pussies rest on huge dildos. As their arms get tired, they have no choice but to impale themselves on the foot-long, girthy dildos. Around some boys, there's a crowd of men playing with their nipples and their balls, telling the boys that this wouldn't have happened had they just won their race -- clearly some losers were punished this way. Others, as it turned out, were taken to one of the torture dungeons for their punishment.

Other crucified boys were left alone just suffering on their own. Some were still trying desperately to lift themselves off the dildo crying and weeping, knowing it was always going to be a losing battle, knowing that eventually they would have to give it up and impale themselves. Others had already given up. They were clearly in pain, as they let the dildos sink ever deeper into their already well-stretched holes. Yet others continued to fuck themselves -- either wittingly or more likely by not giving up yet collapsing onto the dildo and then being pushed by the new pain to lift themselves up again, only to once again not be able to hold themselves up and collapse again.

Looking at all the suffering losers, I needed to remind myself of what the staff always stresses when you check in as a boy: you can leave at any time. They may be suffering, but they know they can leave. They're therefore choosing to suffer for the men they are serving tonight. I think that's beautiful and I know that if I lose, I will also choose to take my punishment and choose to suffer -- I'd be proud to take my punishment in stride.

Then I looked at my competitor -- apparently a pro at this. He was kneeling by his master's side. He was a young, skinny asian boy. It was hard to imagine such a small-framed boy taking these huge dildos at all. Then I looked into his eyes and saw lust. I knew he was here for the sole reason to constantly push himself further. I could only think that if I were to lose to anyone, I'd be proud to lose to a boy that I don't doubt is a true slut. I don't want to think about the consequences of losing, though. I might be new to this and he sounds like an experienced slut, but I know I can be as big a whore as any boy here.

My masters give me a big bottle of lube and tell me I can use as much as I want or need. I look at those last few dildos and can only think that there will be no such thing as too much lube. My competitor is also using tons of lube. He seems focused. He's been here before. One of the staff members comes over to explain the rules, which seems superfluous. He did make it clear that we need to fully press our cheeks against the bench before moving on to the next dildo and that he will be keeping watch to make sure that we do. Also, the masters are not allowed to help -- for example, by pushing a boy down. And, no poppers! The winner, of course, is the first to fully take the last dildo. If neither of us make it there, the one who gets the furthest wins, but the master still may punish the winner for not making it to the end.

I had fantasized about about games and contests like this before, but now that I'm about to embark on one, I am both terrified and energized. I take big dildos all the time -- it's become somewhat routine -- but I hadn't been as excited by them for a long time -- or, scared!

We are both ready and concentrated. The staff member gives the signal and we both lift ourselves over the first, medium-sized dildo. He sinks down on it like it's nothing. I don't struggle with it either but he immediately takes a small lead. I realize I won't have the luxury of taking time to adjust. Those first few dildos I just have to rush through in order not to start the really challenging ones already behind. The second one is still medium-sized and I just plunge myself on it. By the fourth dildo, one I would consider large but not huge, I had pretty much caught up with him. There were three more to go. I am not yet too worried about the next one -- it is large but a size I know I can take. I cannot help but continue staring at the last two, however. I've never taken dildos that big and girthy, but I know I will bite through lots of pain to try try as hard as I can.

We keep on the same pace through number five and start number six at the same time. My ass is in agony as I start on the sixth one. It takes me a few minutes to slowly push myself down. Luckily, I see that the asian boy is struggling. He's dripping sweat and he looks worried. I've taken a lead of 1-2 inches on him. He grunts. Talks to himself: "Just push through this! You know you can do this! You've done this before! Don't let a newbie beat you!" I almost cannot believe I have done this, but I feel the bench against my ass cheeks. I look down and I see the dildo bulging in my stomach. My Masters for tonight are starting to get excited: "You can do it, boy! Just one more we know you can do it."

I pull myself off the dildo. My ass had never felt this empty. I see that my competitor still has more than an inch to go, and I see a mix of agony and anger in his eyes. As I start to work on the last dildo I once again wonder whether I would be able to take one this size. However, I didn't think I could take the previous one either! I tell myself: "Just keep pushing yourself. You're here to always find and exceed new limits!"

As I push past the first few inches, I hear the other boy grunt and just push himself down that last inch. There's a shout of agony followed by an excited 'finally!'. He's catching up to me. I need to keep working diligently so as not to lose my lead. I keep sinking myself onto the dildo inch by inch, and to my surprise I am not in agony. I feel like I'm in a strange trance. I feel the pain but somehow it just doesn't seem to matter. I am driven by endorphins and I just keep pushing on. As I see the other boy get ever more desperate and starting weep knowing that he may very well lose I feel more and more confident that I can actually make it. I only have two more inches to go and my stomach is bulging more than I had ever seen.

Then, another big grunt followed by a scream of agony. My competitor pushed through and has almost fully caught up with me. I start to doubt my slow-and-steady approach and decide I'll have to accept one big dose of agony to win this game. I wish I had poppers available. I take a few deep breaths, tell myself 'just one more big push', and scream. I push. I'm in agony my ass and guts feel like they're completely ripped apart. And, then, I feel it! The sweet feeling of the bench against by ass cheeks. The feeling of victory! I scream out in joy and agony! My Masters celebrate.

The asian boy bursts into tears. He starts to profusely apologize, bawling, to his master. His master holds him tight and says: "You did your best, boy. And, I know you'll take your punishment in stride. You may not have won this game, but I know you'll make me proud by taking your punishment like a good bitch boy."

"I will, Sir!" I watch him and his face starts to glow again as he says this. I can see that he'll take pride in accepting his punishment, and he is glad to know that his master trusts him to be able to take it.

As I slowly lift myself off, I still cannot believe I took this dildo. I cannot stop smiling with pride as both the Masters embrace and kiss me. They said they couldn't have been more proud -- neither could I. They tell me to go console the poor loser. I hold him. He's so tiny it's hard to believe he even made it to the huge last dildo. He holds me in return. I feel his body warmth and there is something sweet and touching about this moment, as the masters looking on also note and comment. He's starting to calm down and his tears are drying up.

I tell him, he'll be fine: "If you can take dildos like that, there's no punishment you cannot take." He smiles and kisses me. I am somewhat taken aback. Are we allowed to kiss? I look over at my masters and they smile and nod. I kiss him back and we start making out. He's sweet and tender, which makes me wonder how he ends up in a brutal and extreme place like this. He pushes me onto my back and lifts my skirt. He licks my balls and plays with my locked dick. The cage feels painfully small. I cannot believe this is happening! The masters just look on and allow it to happen. He unlaces my corset and kisses my body, lightly biting my nipples. I moan. I feel guilty for enjoying the attention -- I'm not here to be the one receiving pleasure.

Eventually, his master pulls him back: "That's enough, boy. It's up to his masters to set limits." The boy smiles at me as his master leads him away no doubt to wherever he's going to suffer his punishment. Yet, he now seems calm and resigned about it -- even somewhat excited to show his master and all others here how much pain and torture he can take.

Master M attaches the leash to my collar again and says: "Come on, boy. Time to find some more fun." They didn't put the plug back in I wonder whether it would even stay put with my ass so stretched right now...

TO BE CONTINUED

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