Day 24. Ruined forever
This chapter is in three parts:
Part A. Set in the gym, Carl makes a very public bet about the size of Bobby's cunt. Contains exhibitionism, humiliation and graphic body/sex descriptions. Average reading time: 15 minutes
Part B. Carl's bedroom, Carl and Bobby get geared up. Contains leather, cock worship, and aspects of submission and domination. 10 minutes
Part C. Carl's playroom. Bobby is fistffucked and ruined forever. Contains intense fisting, punching, double fisting, cunt wanking... you name it! 10 minutes
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Part A. Cunt competition
`It'll soon be time to find out whether the stretch has really taken hold.'
Those were the words I signed my last entry off with. Carl lying in bed next to me and murmuring in my ear... has the stretch really taken hold? A few days later and I can unequivocally answer yes, absofuckinglutely yes. There is no way my hole can ever go back, I'm going to have a cunt for life.
It's only now that I can fully appreciate the graft - by Carl, Jay, Trent, the doctor and all the others - that has gone into my complete and irrevocable transformation. And honestly, the craft that has gone into making me a cunt is almost unbelievable. The School has taken me from being a complete sexual novice to dedicated fist whore in just over three short weeks. Being a virgin seems like a lifetime ago.
Right now I'm totally living in the moment though. Carl has just fucked me!
The night he took my cherry was a pivotal moment in my life and I've been wanting to feel his thick dick inside of me again for so long. Yes, I've been fucked by loads of guys since arriving here but none of them have come close to the impact my first fuck had. I've been desperate for Carl's cock ever since. And it's just happened in a way I never could have imagined in my wildest dreams when I first arrived at the School.
It feels as if he's has been building up to it for a while. Whilst the pace of my training has always been intense, it really seems to have stepped up a gear over the last couple of days. The machine training has been brutal, the pumping sessions have been feats of endurance, and my fisting sessions in the evenings have been savage. No warm-up, just straight up out and out punching.
I trust that Carl knows best though, even if at times it has felt a bit over the top. Going from a pussylip pumping session straight to circuit training in the gym is a complete head fuck for example. It's made easier that I'm no longer wearing a stretching plug or the ring of steel (Carl thinks I've progressed past that point) but harder that I'm made to advertise my status to all the guys in the gym.
Yes, Carl has upgraded my tank top... For the last couple of weeks I've been wearing a powder blue top with BOBBY LOCKED KUNT' in gold (to reflect my hole being plugged and my cock caged). However, now it says BOBBY PUFFY KUNT'. Technically this is accurate - my cuntflaps are swollen and rub against each whilst working out - but that doesn't mean I like the stares and comments.
In fact, I'm pretty sure my new top was the direct cause of what happened in the gym yesterday.
Carl and I were working out by the mats and one of the tutors came over from the boxing area. It was Hiro, who I'd last seen on stage when I won the vote to be the School's pussyboicunt for the month. If I'm honest I thought he still looked pissed that his contender (a young jock called Ben King who was working through his own 100 dick challenge) hadn't won the coveted status. Hiro was obviously still taking it very personally as he was making a big deal of it, asking for proof and evidence that I had truly risen up to my new status.
Hiro and Carl weighed each other up. Hiro was Asian and powerfully compact. He was wearing long, shiny shorts and a white tank-top. He'd obviously been sparring as boxing tape was unfurling from his hands, and his body was covered in sweat. I could see his pupil loitering in the background. Ben almost looked like your stereotypical jock if it weren't for the slightly desperate expression in his eyes. He was wearing a jock and a white tee with BEN NO KING GOOD' on the front. Jesus, what had been going on with his life?!
(He'd been sent to the School by his Dom boyfriend to learn to truly appreciate the value of a good dick. He had to suck and be fucked by 100 dicks, and then record a video log in exquisite detail of every cock, every fuck and every load to complete the challenge. If he missed out the smallest, microscopic minutiae about the fuck then he was out and back down to dick one - I guess the task was taking it's toll!)
Carl was taller than both Hiro and myself, darkly handsome and naturally fit. His arms, shoulders and chest were a symphony of curves, each muscle group bulging perfectly and meeting the next. He was wearing simple grey sweats (that deliciously revealed the thick shaft and bulbous helmet of his dick) and a close fitting navy tank. His forearms were covered in dark hair, which extended across and up his chest. It made for a hot contrast against the hairless Asian...
Hiro definitely had a bee in his bonnet about his boy missing out though. He kept on saying that I was a wasted opportunity and that Ben was the true premier league cunt, that his pupil had the better hole by far. Carl wasn't having any of it. He said that his boy (me!) had nothing to prove, especially not to a loser like a Hiro. (Never have I felt prouder of Carl's respect for my hole than right then!)
Tensions were getting high when all of a sudden the doctor appeared. Jesus, did that man wear anything other than rubber?! He'd evidently been working out too, as his muscular Dad bod was glistening in sweat. Some of that sweat must have been because of his natural rubber wrestling singlet though - it was semi-transparent with black piping and the school's logo was proudly displayed on the front and back: a big, black fist punching its way through a giant, red hoop. The rubber did very little to conceal his hefty schlong, which lazily bulged from his crotch and out along the top of his thigh. He was the fantasy ideal of every horny sport coach rolled into one package.
The doctor had heard the argument and came over to calm things down. He said that if Hiro and Carl felt so strongly about it then they should put it all to the test. A wager between the two to settle the matter once and for all.
Carl seemed pretty confident and happily accepted, though Hiro seemed to agree more begrudgingly. Maybe he was all mouth and no cunt as he didn't seem so sure now. Neither knew the terms of the wager or how it was going to be settled, but the doctor insisted that Carl and Hiro shake hands... the bet was on!
The doctor rang a bell next to the boxing ring. This must have been an agreed signal for everyone in the gym to stop exercising and gather round, as pretty soon we were surrounded by about 40 guys - a mixture of tutors and their students.
The doctor started talking and said a `serious' issue needed to be resolved. He framed it as a contest between two cunts. One developed naturally, the other forced. Which was better? Which resulted in the most progressive pussy? It was a battle of machines, fists and toys against 100% pure-grade dick. The anticipation in the gym was electric - it looked as if the tutors were pretty excited at finding out the answer but the students were all leaning in too. I guess that for many of them the competition might shine a light at what lay ahead for them...
The doctor announced that if Carl proved to the winner, then Ben would be machine fucked for 24 hours solid.
Fuck! I knew only too well that no hole could survive hooked up to one of the School's machines for that long. They were built to heavy-duty industrial specifications, showed no mercy or compassion and had the power to burn out a pussy in way less time than 24 hours.
Hiro and Ben's faces slightly wilted as the doctor explained that it would be the fastest takedown of a cunt in the School's history. By the time the machine was finished Ben would be permanently slack and sloppy - way, way beyond the point of him being a good fuck for his super hung boyfriend. Who knows? If the boyfriend liked a tight fuck then maybe Hiro would have to take Ben's place and become live-in cunt to the man's pussywrecker and his sexually deviant friends?
The crowd were really getting off on this idea. Maybe Hiro wasn't liked all that much? He did seem pretty arrogant but surely he must have been confident in Ben's hole to even get him into this competition. Christ what would happen if I lost? I mean, yes, Ben's tee did make him out to be a bit of a failure, but that didn't necessarily mean he wasn't taking a lot of dick. It just meant that he'd fucked up being attentive enough to describe the shag in enough detail to keep Hiro happy. For all I knew Ben could have been taking cock virtually 24/7. His ass could be a slack meat puppet by now. Where would that leave me?
Absolutely fucked.
The doctor said I would be sent to the School's medical wing for a complete restructuring of my cunt. I could see Carl's eyes burn up as the doctor explained the procedure. The giant chasm that was my inner cunt would be surgically reduced in depth and width, my gape would be stitched up until it puckered up tighter than a quail's snatch, and my beautiful pussy lips would be completely removed. All of Carl's hard work and dedication would be gone! I would be taken right back down to bonafide cherry status, sub-virgin almost.
Christ this was sick. Some part of me wished that Carl would withdraw, not that I wanted Hiro to have his way. A bet was a bet though, and I could see from both their faces that they grudgingly felt the stakes were evenly matched. Both men were in jeopardy if Ben or I lost, they just lost very different things. I had no idea what to think, I guess I had to put all my faith in Carl.
The doctor held out his arms to calm the crowd and then explained the contest. "This is going to be a battle between two schools of thought... Is it better to force develop a hole with toys and fists, or can better results be achieved through sheer force of cock alone?
I can see lots of pupils at different stages of progression in front of me. I also see some very different approaches to cunt development represented too... Some of you are on an all-dick diet, some on a rotation of big toys and even bigger dicks, some on a training regime of fists, stumps and feet...
I'm going to be kind and rule out the cock suckers, cum gobblers and jizz eaters though, you guys can all relax!" said the doctor as the crowd laughed.
"Everyone else has a cunt though and all of them are different. This contest? It's going to be a competition of resting cunt state. Who has the biggest and best? I'm going to select five pupils at random to join Bobby and Ben up here... and then let them self-organise in cunt size order!"
Fuck! The doctor had turned this sick wager into a horrific team building exercise! It was a pretty simply challenge but I knew this was going to be horrible. Ben and I watched as the doctor went round picking his guys. I don't know how much the doctor knew about the individuals the School were training, but everyone's tank tops gave something away...
First of all there was a brunette guy wearing a red tee with `MALCOLM MANHOLE' printed on it in gold letters. He was handsome and pretty buff, but the first thing you noticed about him was that he always walked bowlegged. I'd seen him a few times in the gym and that was a bad sign - it meant his training was probably as advanced as mine.
The next guy the doctor choose was a lean, hungry guy called `FREDDIE FUCK DITCH'. He pretty much bounced onto the mat and seemed to be enjoying the attention way too much. I looked at him and wondered just how developed his fuck ditch was. Was that the source of his confidence?
`JIMMY THE HOLE' was next. His tee was powder blue like mine, but that's where the resemblance ended. Whilst I was athletic (and my circuit training had added on a fair amount of muscle), Jimmy was black and built like a tank. He looked like a rugby player, with broad shoulders and a gigantic bubble butt to match. I was going to have to watch out for him.
The penultimate one seemed more nervous. `VERGE (NEARLY) VIRGIN' I don't think Ben and I needed to worry about. He was obviously very fresh and seemed lost and out of place.
Finally was the curiously named `RUBBER BANDIT' who was the only student I'd ever seen wearing something other than cotton in the gym. His top was made out of smoky semi-transparent rubber, with his name raised out in thick, light pink letters. He was over six foot, pretty well built and handsome if you disregarded the scowl on his face. That wasn't what stood out though... Whilst everyone else called up to the stage was wearing a jock, this guy's dick was hanging completely free. And what a dick! It was nearly as thick as Carl's and just as imposing. A giant vein purposefully ran down the centre of the shaft, curling at the end towards a bulging, uncut helmet. It was the very definition of heft and sat on a pair of giant, low-hanging bull balls. Everything on display was shaved down to the skin, which made him look even bigger. God knows why his face looked stuck in a such permanent grimace. If I had a dick that big I'd be happy about it!
The seven of us were now lined up on the mats. The doctor clapped his hands and simply said `begin'.
We were pretty confused as how to start. One of us (I think it was Jimmy) suggested we simply pick two guys, get them both on all fours in the present position and take it from there. Once they's been judged in size order we we could add one guy at a time and simply keep the ranking going. Jimmy seemed to be taking it all very casually, but then it wasn't his arse on the line for realignment or machine fucking.
Freddie then asked who got to judge the last guy remaining (I think he had high hopes this was going to be him!). Jimmy said we'll get the guy at the small end of the line to make the final choice.
After that, things moved pretty... It was obvious that we should make Verge Virgin the first point of comparison. As it was his idea, Jimmy the Hole volunteered to go up alongside him. It was a good idea as Verge needed all the help he could get. He didn't even know what the present position was. They were soon both on their hands and knees though, their backs arched and ass's facing the room.
An appreciative murmur went through the audience. The contrast between the two guys was pretty hot - Verge lithe and Jimmy fucking solid. All eyes were on their asses as guys in the audience moved their heads and shoulders from side to side to get a better look.
The five of us still standing on the mats debated the two holes and asked each guy for details of their training plan.
Of course, it was a walkover for Jimmy. Verge's ass was fucking tiny in comparison. In fact, I reckon it would be tiny compared to anyone in the School. It was puckered up tight and barely corrugated. If you looked closely you could see it was quite pink and inflamed though, as if it had been used very recently. In fact, I'm pretty sure there was a fat dollop of cum threatening to drip out at any moment.
Meanwhile, Jimmy's hole looked pretty succulent if I'm honest. It turned out he was on a similar program to mine (toys, dicks and fists) but he was on a much slower timeframe. The big difference was that he had been headhunted by the School and knew exactly what he was signing up for. He'd agreed to being admitted if he could go at a gentle pace and keep on playing rugby with his local team. Wow, were those boys in for a shock if Jimmy ever bent over in the changing room!
The next one down on the mats was Malcolm Manhole. Given his bowlegged stance he was someone I was concerned about. Just what had happened to his hole to give him that gait? Turns out his tutor is a bit of a size queen and Malcom is often stuffed non-stop with giant toys. In fact, we had to pull one out of his ass to let his cunt go back to his resting state... For a moment I thought that this might have been an unfair advantage, however, when I saw the toy I started worrying much less. It was very different to the toys that Trent had been using on me. Malcolm's toy was a perfect cylinder about 4" across with a rounded tip. It was big - seriously big - and it left him with a really intimidating gape (fucker looks ready to suck anything into that black hole!) but remarkably virtually no cunt lips at all. Obviously only flanges, helmets and ridges will do that kind of cunt-work. Malcom is just... hole.
Freddie, Ben, Rubber Bandit and I decided he was definitely bigger than Jimmy though and moved them around accordingly. I looked out to the crowd and started to see some dicks rise. This was a hole show like no other but I was feeling pretty tense. I could see Carl and Hiro watching over both Ben and I expectantly. It had actually been a while since I had seen my cunt in all it's glory and I had no idea where I stood against Malcom, Ben or the guys not placed yet.
Freddie Fuck Ditch was next. He was such a cocky little slut. Even though he'd seen Jimmy and Malcom, he still positioned himself at the big end of the line rather than near Verge. Talk about over optimism! He may have taken some dick since he arrived but nowhere near enough to make him king cunt. Ben, Rubber Bandit and myself enjoyed taking him down a notch and placing him just after Verge.
It was at this point that Ben's nerves began to show. He'd seen most of the competition by now and I guess he was getting anxious as to where he fitted in. Perhaps he'd heard the stories of guys being broken down by the machine room and never checking out again. Ben virtually leapt onto all fours and pointed his broad ass cheeks out.
Rubber Bandit and I looked on. I was secretly disappointed... for Ben that is. I was amazed that he hadn't made more progress. I had no idea how many cocks he'd taken since I'd last seen him (the count had been 63) but genetics seem to have dealt him a bad hand and a hole that kept on snapping back no matter how many fucks he received. Maybe the guy had trouble relaxing too, as his hole was clenched shut pretty tight. Sure it has some nice corrugation and it had turned dark pink from all the cock action he'd seen, but it looked like it was going to take a hell of a lot more hard work to stretch his ring wide open.
Who knows? Maybe it would take years of regular fucking to achieve a goal like that? God, his boyfriend must have chosen Ben as he liked the feeling of forcing his big dick into a tight hole. If Ben lost the bet then his boyfriend would be well pissed - the machine fuck would jump-start Ben's slackness and achieve in a few hours what it would normally take years. Ben was fucked, and so was Hiro... What the fuck had he been thinking? It was sheer hubris to imagine that Ben could have won.
Bandit and I positioned him right down near Freddie. Ben's head was slumped and his body was shaking - it was all we could do to get him on all fours again. The loud exclamation of air we heard from Hiro's direction didn't help.
With two to go the order was Verge, Freddie, Ben, Jimmy and then Malcom. I was beginning to feel quietly confident...
Bandit seemed to be getting bored by this point and could barely hold his undisguised hostility in. He said `fuck it' and got down, leaving me to judge his hole. This was the one... I reckon if I had Bandit licked then I was safe and Hiro could go fuck himself.
I had done it! My big, stretched-out pussyboicunt was safe! Even given the time gap since seeing mine, I knew my hole was bigger than Bandit's, and much more impressive than Manhole's. Christ, the thought made me juice up a little in delight! It turns out that Rubber Bandit was sent here for reprogramming by his rich foster parents. He had always had a giant dick that was the envy of men wherever he went. And that was the problem... he thought his big dick gave him the right to do anything he wanted. Which mainly consisted of force fucking his way through high school and college...
Until he'd crossed a line and raped the wrong guy. Maybe the sex was too brutal, too savage, a little too unnecessary... Who knew? But next day Rubber Bandit was enrolled in the School. He was going to be turned into a total bottom, except as punishment he was going to be denied the pleasure of ever being fucked for real. His training was by foreign object only - just silicon, rubber and metal were allowed in his ass! His hefty dick was left swinging and on display to constantly remind him of what he had lost. God, no wonder he looked so angry.
His training had only started a week or so ago so his hole was still pretty virgin. Having said that, we all know what effect a constant stream of the School's toys can do...
I've got to say that the combination of his dildo abused hole framed by his muscular ass cheeks looking damn hot. Even though you could sense the antagonism radiating from his body, there was no denying he already resembled a complete fuck bitch when in the present position. His giant, shaved dick and pendulous balls hanging between his legs made him look like a milch cow. Put the entire package together and it cried out for hardcore abuse.
I put him between Ben and Jimmy, leaving just me to be scored. Verge was first in the line with the smallest hole, so the doctor asked him to place me. I presumptively got down on my hands and knees at the big end of the line (next to Malcom) and waited.
The appreciative sigh from the audience told me that I had won it! Poor Verge didn't know what had hit him though. He still had to describe the hole parade, starting all the way from Freddie to me. He barely had the vocabulary to describe what he saw, let alone digest whether this was his future too.
He walked up and down stammering... he started off talking about Freddie's hole but in seconds he was interrupted and told to call it by its proper name. Verge gulped and started again.
"This cunt looks small and tight" he said of Freddie. "Whereas this cunt looks slightly bigger and angry." Boom! There goes Ben from the competition (and ouch! there goes his tight little cunt too!). He then described Bandit's cunt as "looking wider and deeper than Ben's."
Verge then flushed even redder as he got to Jimmy's and he struggled to talk. The crowd egged him on. "This cunt looks like the porn I found on my older brother's computer. He's got a big folder of girls... showing off their pussies, and this looks just like them. Except this cunt is not quite so thin or long, but it's got lips and everything!"
The crowd jeered wildly and the noise seemed to boost Verge's confidence. He described Malcolm's cunt as being so open that you could drop stuff inside of it and it wouldn't even touch the sides. Cute.
And the he got to mine... There was a pause and then a sharp intake of breathe before it all just flowed with out stopping.
"Jesus this looks like nothing I've ever seen except if you imagine a cunt as a deep open trench with pussy like thick meaty lips on either side except this is bigger and Jesus it's gaping wide and open and pulsating and fucking juicing up as I talk and getting all slick and musky..." his voice tailed away as he simply ran out of words.
The crowd went wild. The doctor strode over and grabbed my ass cheeks to really spread my cunt lips apart. "We have a winner! Look at that! The perfect union of man and machine working together!" he announced. Moments later Carl was by my side and tousling my hair. I had never been prouder.
And Ben and Hiro? They were locked in conversation, evidently they had a lot to deal with together! The doctor bid us all off our feet. I suddenly saw Marcus standing to one side with a couple of heavies, presumably to take Hiro and Ben off. The other cunts went back to their tutors, some with confidence, some with guilt at not doing so well, and others with trepidation as they looked into their future. How far they had to go...
Me though? I was on cloud nine. I had won! Not only was my cunt spared from realignment, but I had made Carl proud. Jay joined us that evening and I received an extra special fisting as Carl described the line-up. Each man alternately fist-punched me as Carl shared every detail...
Part B. Geared up
That was yesterday though. Today was something else entirely. Ben's cunt takedown aside, today I was still expecting to be taken to one of the machine rooms for my normal morning session. Instead Carl intervened and told me to have breakfast, get douched and then dress in some clothes he'd lay out for me.
Having my clothes controlled had been a big part of my first few days at the School and I had no doubt it had helped set me on the path towards my current status. It was going to be a lot fun to revisit the idea. What would I wear now that I was a qualified cunt? I had just helped Carl win a massive bet that pretty much proved my abilities, so I was eager to find out what was going to be laid out on the bed.
I was slightly shocked to find a powder blue tank top, a low-rise pair of tight tan shorts, and a pair of long white socks with a red and blue stripe at the top. These were exactly the same clothes I had worn on my first few days at the School! If anything I felt as if I had regressed as the top was nameless - surely at the very least it should have `BOBBY PUSSYBOIKUNT' on the front?!
Hesitatingly I slid into the clothes. I was pleased to feel just how tight they were compared to the first time I put them on. All those circuit and cardio sessions had definitely not gone to waste. I felt muscular and proud of my body, and proud of how I had developed. I no longer felt the same trepidation or uncertainty in my sexuality. In fact, I felt confident and secure.
And then Carl walked into the room... Fuck me! (No, literally, please fuck me!). He had made me wear the same clothes I'd worn on my first day and so he was wearing his too. Tight black leather jeans, knee-high engineering boots and a simple, dark navy t-shirt. He looked as much a man as the first time I'd seen him, even more now I knew what he was capable of. I felt slightly spell-bound and I couldn't stop my cunt from spontaneously clenching real hard.
He held out his hand in open invitation and said "don't worry, it's going to be just fine..." Ugh! I couldn't contain myself anymore. Without hesitation or thinking I did what I have wanted to do for weeks: wrap my arms around his powerful body and kiss him deeply. Our desire was absolutely mutual, in fact I'm not sure who got their first. Arms were interlinked, lips collided and the world shrunk to just two people.
Whilst I knew that Carl and I would never be a couple - the School didn't exist for that - all the feelings I had kept inside of me these last few weeks came out. Feeling his stubble on my face, inhaling his scent of warm leather and fresh sweat, touching his broad shoulders and powerful arms... it was intoxicating and I didn't want it to ever end.
Carl's hands seemed to be both everywhere and yet perfectly still. In the moments of stillness as he kissed me - holding the back of my neck, my upper arms or tightly cupping my arse - made me feel more passion than I had ever felt in my entire life. This was what it was like to be with a man.
Finally he slightly pulled away and I opened my eyes to look into his. All I could think to say was "thank you Sir" and I absolutely meant it. He held my gaze and stepped back slightly. He then used both hands to yank open and shuck my shorts down my legs slightly.
"Thank you boy... 24 days ago I said that everything I was about to do was going to be for your own good..." An arm reached out behind me to find the top of my ass cheeks. "I told you I was going to turn your tight little hole into a sloppy pussy." His hand moved south to the opening of my cunt. "I told you I wanted you to fulfil your true destiny in life... I asked you whether you wanted to be cunted?" The best part of his hand sunk into my gaping pussy and I involuntarily pulsated with deep seated lust.
It was probably the most honest moment of my life... With his hand buried in the fist trench he had created, Carl reminded me of my true purpose in life and the journey I had been on.
We stood still, looking into each other's eyes. Even though Carl wasn't moving the strength of his gaze was enough to turn my body over. Jesus, I could feel my hole beginning to get juicy... Carl flexed his hand slightly and slid more of himself inside of me. Fuck! I couldn't hold back! Seconds later I had my first body-shattering pussygasm of the day. I could feel it well up inside of me, my cunt walls pulsing around Carl's hand, threatening to push it out. Carl held firm though and kept the orgasm going for as long as possible. I shuddered with pleasure, trembled with ecstasy and moaned with desire for more.
Eventually I returned to normal. I felt weak at the knees, but all the time my eyes had not left Carl's. He slowly removed his slicked-up hand from my cunt and wiped my ass juices on the front of my tank top. "It's time to get you ready bitch, I want you to remember today for a long time..."
A final aftershock of the pussygasm pulsed through my body. I was ready for whatever he desired.
Carl told me to strip and in seconds I was naked. It felt good to fling off the overly tight shorts and boyish top, discarded remnants of my old self.
Carl gestured towards me and I followed him into his playroom. The contrast between the two of us could not be more extreme. Carl, tall and imposing in his boots and leather, a symbol of power. Me, naked and willing to do anything for his fists and cock. And yet there were similarities too. In fact, although submissive, I felt powerfully grounded in knowing that I had been crafted into the perfect cunt, the perfect plaything for tops who knew exactly what they wanted.
Carl looked at me and said that this was the moment I became both man and cunt... that life began anew from today.
We were standing next to a padded bench and a tall mirror. It was clear he had assembled a collection of new clothes for me to wear. The first item he handed me was an off-white jock strap.
"I want you to put this on. We taught you a long time ago that your cunt is the primary source of your pleasure. Whilst your dick may still get hard it is not the source of your power. Covering it and yet keeping your ass naked will always remind you of that truth." I slid the jock up my legs to my waist. It felt snug and secure.
Carl then lifted up a beautifully made pair of black leather chaps. I could almost smell the quality before he had even placed them in my hands. He explained that the chaps were perfectly tailored for my body and they should last me a lifetime and only get better with age. "It's your duty to look after the leather, but it's also your duty as a good bottom to keep your body in perfect shape for them. The leather should always be tight, your ass cheeks should always be perfectly framed and your cunt always on display and available to the world."
I had never worn any leather before but the feeling as I drew the chaps up my legs surprised me. The thickness felt like a second skin closely wrapped around me. The tightness gave me a feeling of invincibility, whilst the cut of the leather defined and lifted my bubble butt, making me feel supremely confident. A double stripe of red leather ran down each side, a signal to the world of just what I was capable of.
A chest harness was next. Made of a much softer and more supple black leather than the chaps, of course it was trimmed with red piping. However, even though I had worn harnesses at the School before, I had never seen one quite like this.
Both the front and back had a large panel of leather in the middle where the four points of the harness met. The breastplate was about 2" by 3" and out of the corners radiated four heavy-duty metal buckles. The backplate was considerably larger and looked to span the width of my shoulders. However, it was the symbols sewn onto the leather that made it truly unique: the red outline of a giant pig with a black clenched fist overlaid on its centre. It looked perverted as fuck. Carl said the fistpig stamp would display my true cunt credentials to the world and I should always wear it with pride.
I slipped the harness on and buckled the straps. It made me feel incredibly horny: the tightness around my muscles reminded me both of my strength and as if I was in constant bondage, always ready to be used. It was a good feeling. I looked down and saw the fistpig. It would always be there to keep me company and, even when things were at there most intense, it would remind me to be the best cunt I could be.
Carl then handed me a pair of engineering boots, just like his. He said that they would help me stand tall and proud, ready to go anywhere and do anything. I put the long red socks that came with them on and then slid the boots on. Instantly I felt taller and more centred. I was one cohesive unit, ready for anything.
Finally he picked up a wide leather arm band. It was black and a good couple of inches thick, with two broad red stripes running down its length. He asked me to hold out my right arm and then started to fix the band around my bicep. It was the first and only piece of clothing that he put on me himself and his touch made it deeply special. He fixed the arm band slightly too tight, forcing my biceps to bulge out around it.
Carl explained that the double leather band marked me out as an experienced - and talented - cunt. For the the first time, from the outside, I felt a whole man... now I just needed to fill the deep emptiness in my cunt to be complete.
I was ready to be fisted and more horny than I'd ever been in my life. I wanted to try out my new gear, to experience what it felt like playing wearing it. I eagerly started to make my way over to the sling before Carl halted me.
"Where do you think you're going boy? We're not done yet!" he said sternly. I suddenly realised that there was a second pile of gear on the bench: Carl's clothes. Fuck! In my eagerness to be fisted I had completely forgotten about him.
"Christ Bobby, you really let a little bit of success go to your head don't you? Win one, tiny insignificant wager and you suddenly think you're king cunt! Well you're not and if you keep up with that attitude no-one is going to want to fist you, pussyboicunt be damned.
Here I am doing all I can to turn you into a proper, fully-functioning cunt and yet you're only interested in yourself! It takes two to fist, Bobby, or have you forgotten that? If you're going to be a true cunt you need to put other people first! Good tops are in short supply out there..."
I could feel my face burning red. I had obviously seriously pissed Carl off and I felt humbled. I immediately asked how I could make it up to him. He replied by saying it was my turn to dress him. It was my turn to show my attention by care and effort I took in getting him ready to play.
Fuck, did I feel tiny! Carl had just given me an amazing set of leathers that expressed and reinforced my identity as a fistpig and yet I had ignored his status as the Alpha who had woken my true nature. I resolved to do my absolute best and think of his needs first.
Carl nodded at me and then sat down. He stretched one leather bound leg out and told me to take his boots off. I quickly got down on one knee, firmly grasped his ankle in one hand and his calf in the other and gently slid his first boot off. It felt good to be at his knees, even better to be touching his gear. I gently put the boot to one side and then slid the second off.
He stood up and told me to remove his navy blue t-shirt. He gently raised his arms above his head to help, and I pulled the tee out of his jeans and started to lift it up his body.
Fuck! The emerging sight of his treasure trail and then broad pelt of hair made me want to bury my face in his chest. I almost died in the last moments when his t-shirt went above his shoulders. The wave of fresh sweat from his pits was intoxicating. I paused. I could feel my face being magnetically drawn into them, ready to sniff and lick and--
"Later. If you're a good pig." Of course! His words bought me back to my senses. I finished lifting the shirt off his arms and then neatly folded it.
Carl then told me to remove his jeans. I sunk to my knees one more time. My arms reached for his belt buckle, my eyes looking up to his. I held his gaze as I unbuckled him, released his top button and then pulled down his fly.
I immediately felt the heat emanating from his jock, and the musk of pure man from his junk. Even though I felt I shouldn't be touching his package, Carl's jocks were always so overfilled that it was difficult not to. My fingers accidentally grazed across what could only be his shaft. It was already chubbing up and getting hard. Christ, if this process was turning him on then it was making my entire body pant with desire...
I slowly shucked the jeans down his firm legs. He lifted up each foot in turn to help me remove the jeans, before I neatly folded them into a pile too. I then rolled down each long sock and balled them both. Only his jock remained, a dense patch of precum turning the material moist...
I wasn't sure what to do next. Oftentimes he wore a jock when fisting me so on or off? Carl sensed my hesitation and told me to remove his jock. My head involuntarily perked with delight and I reached up to grab hold of both sides.
I firmly pulled the jock down... for a moment the material caught on Carl's hefty schlong but it soon released itself. His giant fuckslab sprung free so quickly it was if his cock had been kept captive for an eternity. Even though I had seen it many, many times, this was the first time I had been up close in days. It's sheer size and girth always amazed me. It was a true pussywrecker and it could wreck mine anytime it wanted.
I continued to pull his jock down but my look of adoration and cock worship in my eyes must have done something for Carl. He always was a copious leaker, but the flow from his dick right now was something else. It glistened in the light and smelt powerfully of sex. I wanted it.
Carl could sense my desire, I knew he could. "What's wrong boy? Do you want some? Do you want to taste me?" he asked, almost smirking.
It was all I could do to nod. I felt as I was panting in heat. I was still on my knees at this point, my head so close to his crotch that I was hypnotised by his leaking dick.
He wrapped one of his hands around the thick shaft and started to milk his cock for precum. A thick dollop started to gather at the head and - just before it was going to fall - I quickly moved my head to one side and held out a palm to catch it! The drips collected in my hand, a mini lagoon of pure nectar. The flow stopped and I looked back at Carl. Without breaking eye contact I took my hand and reached around my back to lubricate my swollen pussylips with the precious fluid. I wasn't going to waste a drop!
"Good pig, good boy! I'm impressed" said Carl. I felt as if I had just passed another test. My dick-sucking first impulses had definitely been removed and completely replaced. My hand came back round and Carl told me to lick myself clean, said he didn't want me messing up any of his gear. Fuck! This was how body fluids were meant to be consumed - as raunchily as possible. I licked my palm clean. It tasted great and I felt like a true man.
Carl directed me over to the pile of his gear. There were chaps, a harness, a vest and an arm band. I looked around in vain for a jock but couldn't see one. Did this mean--
"Yup, that's right kid. Cock out today. I told you it was going to be a special day!" Fucking hell! I had no idea whether it was the precum that I had just put there or my own ass juices working overtime, but my cunt was beginning to feel distinctly moist. Fuck I wanted this so much!
I picked up the thick, heavy chaps and started raising them up his legs. It was a struggle. His thighs were so thick and the leather fitted him so closely. Carl was generous in helping out a couple of times and soon they were on. His leather clad legs looked solid and firm, two pillars of strength. Of course, two stripes of red leather ran up each side of his chaps as well.
"See Bobby, where your chaps show off your ass and cunt, mine shows off my dick. It means the world knows I'm always ready to fuck, whereas you are always ready to be cunted." I couldn't agree more. His hefty dick and low-hanging balls confidently filled the front of his chaps, whereas my bubble butt overflowed the back of mine. Man alive did I want to get fucked!
Next came his harness. I unbuckled it and wrapped it around his shoulders, chest and then under his arms. It felt so good to feel his skin and I lovingly secured each buckle. Carl told me that the harness showed off his powerful chest, and asserted his dominant power. Over this went a black leather vest, which did even more to accentuate the shape of Carl's muscular body and his covering hair. He looked amazing.
I then put his socks and engineering boots back up, being careful to wrap the ends of the chaps into each boot. By now he was standing again and looked every inch the leather god. Powerful, confident, a man of action... there was just one finishing touch: his own band. It was identical to mine, except his went on the left side.
By now Carl's dick was as hard as I had ever seen it. As I dressed him I could feel the energy building up inside of him. The sexual tension in the room was potent. The space was filled with desire and the smell of ass, sweat and precum. I couldn't hold back... "Please Sir, please fuck, fist and use my hole! I have never been so fucking hungry for you" I cried out.
Carl briefly looked at me and then landed a deep snog which I returned with passion. He broke off and said "good boy, you're going to need that hunger to get through the day... let's get you in the sling."
Part C: Fisted and ruined forever!
I didn't need to be asked twice. In moments I was comfortably lying in the sling, my legs and boots held in the air by the leather stirrups, my ass available and ready for use.
It was a very different feeling wearing my gear. Over the last few days I had come to feel totally at home in the sling. Whether I was worked up or tense, getting in the sling immediately relaxed and calmed me down. No matter what was going to happen next, whatever the ferocity, the sling felt the place to be. I felt supported. Wearing my new leathers and boots enhanced that feeling. I truly felt like a fistpig, horny as fuck. If I had a choice I would never get out. And yet I also knew that I was here not just for myself, but for the pleasure of the man standing in front of me: Carl.
He always looked hot, but knowing that I had helped get him ready made it even hotter. I looked around and everything was set. A mirror for both of us to see all of the action, a giant container of lube at ass height just off to one side of the sling, a poppers inhaler hanging from the ceiling. (This was a rubber mask a bit like the ones anaesthetist's used in hospitals - except this one was connected to a special dispenser that released poppers when a person inhaled. You then breathed out whilst still wearing the mask and a small rebreathing bag recirculated both the poppers and your carbon dioxide until the next breathe. A great way to get high and my trusty friend in times of need).
"You do realise that this is your life from now on? We've implanted the need to be fisted so deep in your psyche that it can never be switched off. It's ingrained so firmly that there's no way the programming can ever be removed. You're going to be a fist-hungry cunt for the rest of your life..."
At this point I didn't know whether Carl was teasing me by prolonging the inevitable or actually trying to impart a serious message. A brief flash crossed my mind as I tried to look into the future. How would I find the fists that I needed on a daily basis? Even if I lived in one of the big gay cities would I exhaust the supply of readily available fist too quick? Would I become a travelling cunt with no fixed abode? Fuck it, I didn't care. Just fist me already. I clenched my ass muscles a couple of times, hoping the movement in my pussy lips would entice Carl.
It certainly had a reaction! "Oh that is so sweet, boy" said Carl. "Your cunt is oozing juices... all wet with the need to be fisted eh? Christ, I bet you're imagining me punching your slutcunt right now?" he asked.
I absolutely, absolutely was.
His strong hands started playing with my puffy cunt lips - lips he and the rest of the tutors had created through serious toy work, aggressive fist punching and extended rosebud pumping. Whist initially I had been intimidated by them, I now saw them as one of my best (and most honest) features. They were so juicy that they begged for attention, and that's exactly what Carl was giving them now.
They were soft and undulating, sensitive to touch and big enough that there was a lot of distended meat to play with, especially if you were a man of Carl's tastes.
"From the moment I saw your application form I knew you were the one. Your innocence and naivety... and yet your powerful hunger for sex. You were perfect, or at least you would be perfect by the time I had finished with you.
And then when I first lined my dick up with your boyhole I thought I couldn't wait to break you down... I have no use for a tight hole. A cunt should have big lips... it should gape and beg to be filled... And do you know what? I honestly think you're almost there..."
His fist was suddenly inside of me. No matter how many times I've been fisted the impact of that first entry never diminishes. It's the moment when the wait between sessions is finally over, when the emptiness is filled, when the connection between two men is relit. No matter that I was intimately familiar with Carl's fists, to have him inside of me again was always amazing.
"That was my clenched fist you just took in one kid. No one can deny you have a cunt now!" He rotated his fist and gently manipulated the individual fingers of his hand. Already my head was exploding with pleasure. Something felt slightly odd though. Maybe the lube? I asked Carl - there is nothing hotter than having a conversation with a man who's got his fist up your butt - whether it was different.
"Well spotted kid. It's an oil based lube called Crisco. It's a bit old-school but it greases up super slick! You'll get used to it" he replied. With that he grabbed some more from the container and lathered my hole with it, talking all the while.
"I'm going to plough your hole until it's wide and unresisting, then fist you until it's sloppy and gaping." If I hadn't of been lying down I would have been weak at the knees. I took several deep huffs of the poppers and let Carl get to work. He sensed the moment when the chemicals took effect, my cunt muscles relaxing and opening up. When my pussy was at it's most defenceless he rammed his fist back inside of me and took ownership of my hole.
It was a savage and masterful takedown. His fists explored every inch of my pussy, confidently going deeper and deeper, before pulling back and making my cunt cavern even bigger. He rotated his hands, wrists and arms to give me unforgiving and powerful sensations. Once inside of me he pivoted his arms, using my pussy as leverage to open me up even wider...
No matter how many times I play I don't think I will ever get used to these feelings. It's as intense as that very first time I was fisted.
Now that Carl has made me receptive he changed his approach. All this time I had been moaning and crying out in lust. Now I felt as if I was whining or squealing. I wanted it go on forever! He was punching me, alternating from one fist to another. He's telling me that I have such a sweet cunt, such a talented hole...
I suddenly realise he's talking to me directly and asking me a question. I had been so lost in the experience that it took me a moment to come back.
"I said, what do you think Bobby? 500 punches?" he was asking. "It needs to be done if we're going to make progress." He was looking at me expectedly, his eyebrows slight raised and a manic look of pleasure across his face. His upper body was gleaming with sweat, making trails down his hair. Each arm was greasy with lube, a high tidemark showing just how deep he'd been inside of me. It was so hot I couldn't possibly say no.
"Okay then, 50/50 it is!" Fuck! I'm not sure I would have agreed to that if I'd known. The half and half was a serious challenge. It meant Carl would punch me up to the count of 250, and then I would have to use the motion of the sling to ride my ass onto his clenched fist for the other 250. It was a really punishing workout and I had never gone that high before.
It couldn't be stopped though... the longest count to 500 in my life suddenly started. I took a big hit of the poppers, looked in the mirror and it began. The reflection was amazing. A tall leather clad stud punching my hole with his big, clenched fists. Carl's big dick swinging free, rapidly followed by a trail of precum. Me lying back in the sling, my ass framed by the chaps and my chest bound by the harness... Whoever looked at the video playback of this session was going to have a wet dream!
50... 100... 150... the count kept on going up. Carl seemed to be doing them in bunches of 50. That is, he'd change his technique every 50, going from shallow and fast to deep and slow. Every one was a bonafide punch though. Soon I could feel it happening, my mind going numb from pleasure and desire, my hole shuddering with pussygasm after pussygasm.
Carl punched his way right through every one, making them feel as if they were lasting forever. Soon I was quivering, pale and panting, begging and mewling. I had no idea whether I was asking for it to stop or asking for more. Taking the punches was becoming tougher and tougher. I wanted to it to stop - at least to pause - but I then I suddenly knew it was my turn to take over the motion. I was the one who had to take us from 251 to 500!
Carl was counting up to 250, telling me that I had better be ready to take over and not miss a single punch... 248... I grabbed hold of the sling straps in readiness to start swinging back and forth... 249... I tensed and started to pull back... 250!
I used my arms to pull back with all my might. Carl's clenched fist immediately became like a rock, perfectly positioned for my cunt to swallow it every time if I kept the motion of the sling consistent.
I did it! I managed it! Now I just had to keep the motion going backwards and forwards. Even though it was the same fist, the same punch, the intensity was really getting to me now. Riding Carl's fist was much harder than it looked. I felt I was almost at peak destruction and couldn't go on much further.
It was then that I remembered what I was wearing. As I swung I just managed to look down and see my harness. The figure of the fist pig on my chest, a constant reminder to be the best cunt I want to be.
Be the best cunt I want to be.
I repeated those words in my head over and over. I gutted it, I got through the mental block. I rode Carl's fist right up to the 500! By the end the sight in the mirror was something to behold. I had been pounding the sling back and forth, riding his fists for so long that my inner ass flesh was coming out with every punch, almost turning my rectum inside out. My movement of the sling was literally dragging my cunt out with every punch.
498, 499... and with one mother fucker of a punch more, 500!
Carl moved his fist for the first time in an age and slowly withdrew. He then congratulated me. "Well done boy, that was pretty impressive. I was worried you were zoning out but you kept it together. I'm proud of you."
"Please..." I murmured (I could barely get any words out) "please put your fist back inside of me. I feel so empty..."
"My pleasure kid, my pleasure!" he replied. With that he doubled his fists and power balled my hole. Fuck! I was not ready for that! I grabbed the poppers mask and inhaled as deeply as I could. Despite all the punching I felt as if my arse was stretched to absolute capacity. I was delirious as the double attack went on and on, reaming me out to new proportions.
And then suddenly my hole was empty again. I wanted more, I wasn't ready to stop, I wasn't sated yet (would I ever be?).
Carl regained my attention. "Look me in the eyes boy. Enjoying yourself?" he asked. Whatever the ferocity of the experience - perhaps because of it - it was the most intense time I'd ever had in a sling. The line between sweet pain and bitter pleasure so close. In panting breaths I told him so.
"Good. Because now it's time to fuck you."
Fuck me? Carl's cock was mighty and thick - I knew that from the very first time he fucked me - but even with his massive girth I surely wasn't going to be able to feel a thing? I felt deeply confused, my poppers addled brain not able to work it out.
Suddenly the sling lowered down, making my ass level with Carl's giant fuckslab. (The sling was suspended on an electric winch, operated by a foot pedal. Carl could move it up and down in seconds.)
Still confused, I was surprised to see Carl wrap his hefty dick in one of his powerful hands. I guess he was greasing up his cock, though god knows I must be full of lube by now...
Jesus! He pushed his entire dick AND hand into my hole! Fucking hell. Despite the warm-up punching, despite the double, despite all of the previous machine fucking and the toys, it was a seriously tight fit! I cried out, I pushed back, I did everything I could to bear down and stretch myself back onto his cuntmaker. It was like nothing I've ever had in my hole before. His cock and fist together were enormous.
Suddenly he was all the way in and I cried out in relief that the worse of the stretch is over. Fuck! How wrong I was. In seconds he started fucking his cock straight through the hand in my pussy! Carl's dick was so long that I could feel the head and several inches of the shaft thrust deep inside of me before plunging back again. I didn't feel as if I was being fucked, I felt as if I was being violated!
I fucking loved it though. Nothing confirmed more to me this moment that I need it, I want it, and it's my purpose in life. Soon he was using the full weight of his entire body to fuck me. Powerful slams of his crotch against my swollen cunt flaps. Writing these words makes me truly understand why I love this man, the power, the intensity. It feeds me.
And then somehow the cunt fucking got more intense: he stops and then starts jacking his cock off inside my hole! Literally. His body and cock was perfectly still, but his hand is running up and down the full length of his dick inside of my cunt! Ohsweetjesusmypoorcunt! He's lost in the fury of the moment, I couldn't stop this if I tried! Longer and longer strokes, faster and faster! FUCK!
He bellowed and shot.
It felt like the longest orgasm in the entire fucking world! I pussygasmed in unison, my trained muscles gripping Carl's cock and fists, helping to prolong his pleasure and milk all the cum out of his cock.
For moments we were both completely lost, both amazed at what had just happened. Then the reality started to kick in. Our play session had been hours and hours long. Whilst I may have been insatiable, every hole needs a break once in a while. I suddenly wanted Carl - both his fist and his dick - out of my hole. He withdrew his cock, and then slowly pulled his fist out too. The space they left behind was unbelievable.
Carl looked closely at my hole and said "you know, I think we might just have finally ruined your cunt. Close those big, greasy cuntlips for me bitch. Can you? Huh? You can't?! Shit! You ARE ruined!"
It was true, no matter how hard I tried, it was impossible. Carl grabbed a small mirror so I could see my wrecked cunt. It was a sight to behold. Yes, my hole could pulsate and desperately grasp at the air outside... but that was a signal it needed to be filled again, not that it could close. My cunt was permanently gaping and ready for the next fist. The thick, puffy lips an inviting welcome for any and every fist going.
"Well done boy, you made it. I'm proud of you" said Carl. He leaned into the sling to kiss me deeply. I was exhausted but I felt the pride and emotion in those words. We had come a long way.
"All this time we've been turning you into a pussyboicunt. We don't choose those words lightly, or the guys we put through the program.... I look at your cunt today and know that yes, the stretch really has taken hold. Today you graduate. Not as a pussyboicunt, but as a full-blown mancunt!"
Fucking hell! My cunt had levelled up!
Next: Bobby is branded a fistpig for life...
------ Comments and suggestions welcome at stuhadley77@gmail.com