Date: Sat, 22 Apr 2023 11:53:23 +0000 From: Stu Hadley Subject: How I learned to stop worrying and love my hole - Chapter 8 How I learned to stop worrying and love my hole Tan's 8th letter ------ Caged Tan gets repeatedly fucked and is forced to endure restraints and a punishing lube experience. Themes include bondage, fucking, poppers and group sex. Average reading time: 15 minutes. ------ Hey everyone. Cutler says it's time for me to answer some of the many emails I've been getting. Thanks for writing but I can't help but think some of you are perverted fuck-ups. Why else would you write this shit?! Yes, the chastity cage is as bad as I thought it would be. Yes, it seamlessly integrates with the ball cuff the guys at the factory fitted me with. No, I don't think this is a coincidence.. Yes, it's custom made and no, I don't think the cage is shrinking my dick. Flaccid, I still reckon I'm about the size and shape of a soda can. Sure, the thought of having an ass big enough to take a cock my size scares the shit out of me. But that's what I'm here for - I want to prove it can be done so no other guy can refuse. After all, if I can take my freak dick, anyone can. I may have started this journey terrified at the thought of my tight, virgin sphincter being fucked but now I can't imagine life without constant, non-stop sex. That's what everyone wants, right? Straight or gay? No, finding out there's a fully functioning sex dungeon in Cutler's house hasn't made up for the metal weighing down my junk (and mind) since I last wrote. And yes, I am totally at his mercy. There's no way I can wank, cum or even get hard without his permission. The blunt screw tips that line my steel cock tube really are evil. I can feel everyone pressing into my shaft. Finally, no, in all honesty, I'm not missing my cock. It's taken me a while to realise it, but my steel captivity is doing me a favour. It's forcing me to think with my ass, an ass that needs to be filled. My unrelieved balls and the constant banging of my prostate make me a far more enthusiastic fuck. I really need those dicks to unlock my goal. Of course, since I last wrote I've been back to Mike's for yet more stretching. My nipple barbells have been replaced with inch wide silver rings. I've got to say it - maybe I'm biased - but they look pretty good on my well developed pecs. My teats have always been big but these somehow balance them out. Like they're now a feature of my body that can't be ignored. However, the less said about my snout ring the better. Whilst I'm not vain I've always been told I've got good bone structure and handsome to boot. I think the ring only detracts, especially at my age. I look totally fucked up yet still fresh-eyed and eager for more. My opinion is clearly the minority view - the combination of pig and innocence seem to be a winning combination for the guys at work - that's if the ever increasing queues lining up for a fuck are anything to go by. Of course, my big dick being locked up only seems to add to my desirability. The guys know I must have done something pretty severe to royally piss Cutler off so much that such drastic action was needed. The craziest rumour I heard is that I refused to give it up when a chain gang from the local penitentiary showed up. As if! Right now I'll take every dick I can get! That includes Cutler. I place his fuckslab on a pedestal but I'm frustrated my dick worship isn't reciprocated. He keeps on saying I'm not making progress fast enough. Surely my hole must be big enough for a cock my thickness by now? Nope. No. Nada. Denied. He says I'm nowhere near ready. That he knew from my grimaces and the length of time it took me to slide down his cock the first time we fucked that I'm not there yet. He says my pussy gripped his dick like a vice and that simply isn't good enough. Apparently, I'm the exact opposite of an easy taker - if I was truly ready to take a dick my size then I've been able to glide down his in one smooth motion. Right now - he says - I'm just a wannabe. As you can imagine, this is very disheartening. I thought I was making good progress, not least as my head is so full of sex right now. How can I not be advancing? With that goal well and truly on my mind, we've been spending a lot of time in the dungeon, sorry, play room. The room is well equipped with a sling and gyno chair, but Cutler prefers to fuck me from behind. He says it's the best position to go balls deep and really ream me out. For that he hooks me up to a sawhorse - I'm placed torso down with my arms and legs secured to the metal legs by heavy-duty cuffs. It means I can't pull-away or escape. Sometimes he likes to encase me in what can only be described as a full body cuff. It's a 16" wide strip of padded leather that wraps around both my midsection and the bench, complete with three thick buckles that makes it a bit like a corset - it really binds me in place. Especially when he pulls it real tight, squeezing my breath away and making me really fight for it. However, when he wants to be really mean he switches on some electro magnets he's retrofitted to the bench. They're incredibly powerful and line up with all my piercings, holding them steady as a rock. I can't possibly move, not unless I want to rip my nose, tits or cock apart. These kinds of restraints seem to be totally standard for Cutler. As I get to know him more I'm beginning to understand that sex is not just `a' part of his life, it's what he does to live. Just like the leathers he always wears. The material seems to be a part of him - jeans, braces, a thick belt or a constant wrist cuff at home. Or engineering boots, a taut harness or bar vest to fuck me in. Out of the foundry he's never without gear. Till now I had no idea it was such an important part of his psyche, but hey, a while back I didn't know he had a fully stocked sex dungeon either. He always looks hot and in the mood for sex. That's a fact. We get home from our (very different) shifts at the Steel Works and then head to his gym. After a workout is when he likes to fuck me the most. He says that when our best work is done as I'm just beginning to tighten up after the factory line. That means he can shock my hole into remembering what it's here for. To always be a gaping funnel that welcomes every load on offer. I honestly believe I was made to have a cock up my ass. Sometimes he fucks with one agonising thrust, brutally nailing my cunt and then furiously piston-fucking my hole until unloading. Other times he makes patterns on my ass lips with the slick tip of his dick, teasing and taunting me with his pre-slime. Then, when I'm desperate and on the verge of begging, he slowly forces his way in. But only to the brim of his helmet before waiting until I'm extremely graphic in asking just what I want done. `Please fuck me, please wreck me, stretch me out. I'm fucking begging you' I plead. `Why didn't you say so?' he replies, ramming the entire length of his cock deep. This is tough not only on my hole but also on me - I'm conditioned to get hard when I beg for sex but I can't follow through because of my diabolical chastity cage and cuff. To make it worse I swear that Cutler doesn't bother to grease up his dick anymore, or if he does it's with the most minimal amount of lubrication possible. He says I must like the friction and the extra hurt as otherwise I'd relax my hole more. I try, I really do try... Perhaps the worst times are when he slow dicks me on the horse. Long, agonising strokes whilst we watch porn together. It's a test of endurance for both of us. He'll fuck me for half an hour then replace his dick with a wide-necked butt plug (throttled by an ass harness so I can't push it out). He'll then leave me stretched wide for ten, twenty minutes or even an entire hour as the extreme porn continues to play. By the time he comes back I'm outrageously horny and my hole is completely slack, just the way he likes it. Christ, you should hear him moan in pleasure when he sinks his 12 incher inside of me when I'm in that state. Desperate, loose and sloppy. He tries to hold out and take it slow but the warm velvety walls of my anal cavity are simply too much and he ends up furiously fucking me until he pumps and dumps. Knowing it will make him feel real good for a couple of hours and then he'll need to go again? Fuck, that's hot. And all this time I'm learning new tricks too. Take just a couple of nights ago. I was in the fuck position and Cutler brandished a gas mask in front of me. I obviously knew what it was but I'd never dreamed it could be a part of sex play. He pulled it over my head - the feeling alien and intense - and then tightened the rubber straps fast. There was a deep chemical tang I was unfamiliar with before through the fog of my deadened hearing he told me to breathe deep. I felt my head spin and my arse loosen, meaning Cutler could plough into my hole as if all resistance was lost. It was seriously intense and he almost fucked the life right out of me. Thank god he came quick as I don't think I could have taken much more of the fumes. That was my introduction to poppers... ------ Nighttimes are hardly any better. Cutler can be caring one moment, snogging and cuddling, telling me how well I'm doing but then a ruthless bastard the next. I've lost count of the number of times I've woken up in the dark screaming in my sleep as he's mounted my hole from behind for an impromptu piston fuck. In one agonising thrust he rawdogs me (with no more lube than what spits out of his cockhead) until he shoots. Then I have to clean his slimy cock up. With all this heavy loading I've been pleading for a bit of a break. Not least as some of the guys at work have begun complaining about how loose I am by the end of a shift. And at the start of the shift, and all the ways in between. What's really made me worry is overhearing two guys talking - one leaving, the other arriving - that it looks like they've `worn out another one.' Fuck. I'm not even twenty. I think I'm still tight but I recognise its becoming more difficult for me to retain my clutch - all that hole control training seems to be for nothing. I think its because I'm constantly being stretched. Either by dick or dildos. For example, a rack of hole-stuffers have been installed next to my fuck platforms. When a guy finishes he has to choose a toy to keep me open until the next fuck arrives. (This has been incredibly revealing about the dynamics inside the plant. Some men choose to stuff me large as they know the next guy in line has a regular sized penis. That enforced pre-stretch means they'll struggle to touch my sides. That's okay as they usually take one look at my distended hole and decide to let me blow them instead (they still need to shoot and I need the cum). But what I really hate are the guys who maliciously choose a small toy because they know the next guy coming in has an absolute unit of a cock. In those moments my hole seems to forget itself and close right down, invariably meaning my next fuck will be as punishing as possible.) I've bought up that lack of clutch with Cutler and he says I'm obviously not trying hard enough. I worry about my future though, what if I can't hold myself in once all this is done? I've got the rest of my life to think about. He says I shouldn't be worried, that downwards training is easy. I'll `just' have to spend a period wearing progressively smaller plugs. Sure, it will take a while to slowly undo the damage and regain my elasticity but nothing is permanent. Yet. The only real problem is I've tried slipping in one of the smaller plugs I wore at the beginning of this year-long project and that fucker slipped right out of my hole as fast as Roadrunner escaping Wiley Coyote. I've gotten so big and juicy that I can't possibly hold it in, no matter how hard I clench. I was shame faced when I eventually asked Cutler for an upgrade. His immediate reply was, why bother? That we were nowhere near done with stretching me out. That my max was still way off and this was no time to be thinking about going small. I explained that wasn't my intention at all. No, what I wanted was a bigger plug. Something to wear between work and home. Something that would stop the cum and lube leaking out of my hole when I wasn't in use. I was bored of cleaning his car seats. And wiping my legs down. He left and came back with a single plug, apparently the only one he owned I hadn't worn yet. It was a massive pure cone with a wide, hard flare. The shape meant I knew - once in - it would stop my hole up like a cork. But inserting and removing it would be painful. It was my only option though. ------ That's all yesterday's news though. The real reason I'm writing today is that I've had another visit from Akiro. Just this week a sling has been set up in my box/store room, complete with an electric winch that makes it height adjustable for each man I service. It's a pretty neat set-up, especially when I team it with my smoky trans rubber overalls. The chaps cut is really hot and the material perfectly matches the thick, latex sling. (Plus, they're both wipe-down and easy to clean! Super practical given the volume of errant fluids that go amiss when I'm on the line.) I've really gotten to enjoy the new position but I can't deny it's been exhausting too. Guys really seem to put their back into fucking a guy in a sling. It means that by the end of the day I actually look forward to the factory whistle going and my shift being over. Today was no exception. I had one appointment left and I was tuckered out. I was lying back in the sling and really hoping it was going to be an easy fuck. My mood wasn't improved by the previous guy choosing to stuff me with not one but two dildos, side by side. They were a monster stretch and made my hole quiver, desperately wanting to eject them both. However, that wasn't allowed. (Rule number 7: never remove a foreign object from my hole without permission. Of course, the guys I service don't need permission, they can do what they like without consequence.) Instead, I simply topped up my poppers mask (oh yeah, that's been carried over from Cutler's dungeon to here big time) and took a big hit or two to relax my pussy. That's when I heard his voice. Akiro. `Hey cumbreath. Pleased to see me?' he said, bursting in. God, he really is an arrogant fucker, even if he has a golden body and a gorgeous prick. Akiro is the Japanese-American foundry worker who fucked me first - taking away my near cherry status - and then proceeded to lie to Cutler, saying that I had lead him on. Those lies were the reason I have my piercings. Even worse? He'd brought a couple of his friends along. Damn, just what I didn't need: a gang bang. `Time to give you another filling of my superior Asian cum' he smirked. You think I'd be able to resist but I never can. This man is stacked. Everyone wears the same factory uniform but his body is so muscular that his overalls are both tight and loose at the same time. His shoulders and chest strain the fabric, whilst his narrow waist actually makes it look baggy. It fucks with my mind. Fucks with my hole too. He yanked the double dildos out with no thought of my comfort at all. I could tell from the pain that my pussy lips had inadvertently clung to the heavy rubber shafts and didn't want to lose their grip. Too late for that. `Christ, look at what you've become. Such a big, gaping pussy boy with your cock caged and useless' he sneered. Yeah... but he still wants to fuck me. With that he hoisted his cock out and slid his way in. Now, in my defence, you have to remember it was the end of the day and my insides were drenched in multiple, multiple loads of nature's best lubricant: cum. And I'd just been freshly stretched by those evil toys. It was no wonder that Akiro complained I had no clutch left. `Clench down, dickbreath. Work my cock!' he demanded. I tried but I was simply too tired, too worn out. Too lubed out. As his cock flopped about in my juicy hole and he struggled to make purchase there were sighs of disapproval from his friends in the shadows. You'd have thought this would have humbled Akiro, but no. His demeanour shifted and he said I must enjoy having all that cum sloshing about inside me. That it made for a very easy fuck. I could hardly deny that. `Don't you wish you could really feel my cock though? Just a little bit more friction? If you can't feel it then I may as well not be here?' I couldn't deny that either. He grinned, dead behind his eyes. `Good, let's get you cleaned up and we can get a tight fuck...' With that he pulled out - his cock slick with the loads of multiple men - and started searching the store room. He went over to where the chemicals and detergents are kept. What was he looking for, soap? A cry of `got it' announced he'd found what he was seeking and he came back flushed with excitement and evil intent. Fuck. I can't believe I'm forced to relive this experience by writing it down. Cutler says my contract gives no exceptions to describing my sex life, even if traumatising. This one is for you, fuckers. ------ What he'd found was a massive container of `no-slip' powder. You know the kind of stuff? To clear up oil spills? Safety first, right? He reached in and grabbed a big handful of the coarse white powder, smearing most of it over his massive wet cock and the remains over my trench. The thick grains covered his shaft from head to balls, making his dick looked like a crystallised weapon of fuck. Then he did something that really freaked me out, he started packing another handful of the powder deep into my well-turned out hole. Each shove of his fingers was excruciating but that was just the start of it. Once done he started pushing his super-dry cock into my even-drier pussy. The powder had absorbed every ounce of fluid in my ass and it was fucking unbearable! This wasn't what I meant when we'd talked about more friction! I screamed but the fucker seemed to like my pain, if anything it made him double down. My fuck channel was so bone dry that all he could do was apply heavy pressure and slowly shift his cock from side to side, to squirm and push his monstrous pole in. My pussy walls clutched the sides of his cock like super glue and it took a good five minutes of complete agony for him to complete his first stroke. I honestly thought I was going to pass out but when I broke eye contact he backhanded me and snapped me back to attention and the agony he forced me to endure. Finally I felt his balls resting on my butt and there were cheers and applause from his acolytes in the room. `He ain't done yet, boys' he cried. With that he reached forward to squeeze my tits. The hard pressure made my pussy spasm uncontrollably around his embedded cock. `Shit! You guys should feel what this horny pain pig is doing to my cock! Fucking trying to milk me dry, hey bitch?' It was then that things dropped down even worse. He started pulling back, inch by slow agonising inch. I was babbling, pleading and sweating buckets, desperate for it all to be over. But he sunk in again and out, gradually picking up the speed and intensity as my brutal sadistic dry fuck began in earnest. Akiro slammed into me with all his might, fucking me with his entire body. I know some tops like causing pain but surely this had to have been hurting him too? I didn't get an answer as he picked up the pace and with a final, massive grunt he dropped the most intense load of my life deep inside my guts. Thank god the factory whistle then sounded, announcing the end of the shift! If it hadn't I swear everyone else in the room would have had their turn. I've just told Culter about it all and he told me lucky I am. That not many bottoms get to have this kind of experience and maybe my shifts should be extended? After all, since I joined the foundry production has been way up across the board. The only limit is what I can take. Christ, I think I may be doing too good a job. Tan ------ Comments and suggestions very welcome at stuhadley77@gmail.com For more of my stories, please check Nifty's prolific author page :)