Day 5. The program begins
Themes include fucking, bondage, toys, dildos and domination. Average reading time: 20 minutes.
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Jay's told me I've got an hour or so to write this before my first lesson begins. It's fucking odd writing this whilst wanking, not least that I'm right handed. I can only write with that hand, so I'm jacking my cock with my left. It feels weird, like I'm being wanked by someone else. That's actually a helpful distraction from the pain in my balls though - last night and this morning were fucking tough.
The night started with him brutally assaulting my hole from behind again. I thought I would have got used to being fucked by Jay's fireplug of a cock by now, but if anything it felt bigger than that first morning rape. I twisted and writhed on the bed trying to escape his thick dickmeat, but Jay wasn't having it. He just held me down and told me to struggle all I wanted. Said that he liked the fight, and that all I was doing was driving myself deeper on to his cock. I blushed as I heard him saying that it proved just how much I wanted to be fucked, needed to be fucked... None of that was true of course - he'd got me into this sick situation - but the thought of it seemed to spur him on and it wasn't long before he unloaded deep inside of me.
I really hoped that was going to be end of it and Jay would let me fall asleep, but he clearly had other plans. He withdrew his cock, my body seemingly turning against me and determined to embarrass me - my ass letting out a disgusting squelch as his cock left my hole. He let out a monstrous laugh and slapped my ass saying "there's a good cunt." Am I ever going to get used to being called that?!
At this point I was still laying on the bed and he told me not to move. I could hear him walk around the bedroom, picking things up and assembling a small pile of stuff on the bed next to me. I wasn't prepared for what he did next though. Within moments he had secured thick leather cuffs to my wrists and ankles, and then rope from each cuff to the four corners of the bed. I still had a little freedom of movement but essentially I was splayed out on my front with my rear totally on display.
Jay apparently wasn't going to allow any movement as I felt his hands grab my balls and pull them down and away from my body. I then felt him attaching some kind of leather device and the sound of metal chains (I found out later that this was called a ball parachute and I should expect to have it used on me often).
Seconds later I could feel tension on my balls. Fuck! They were being stretched away from my body. I had never felt anything quite like it and the feeling was fucking intense. As I was alone with Jay my cock was unlocked and once more my body betrayed me: my cock got hard under the pressure from the stretch. Fuck! How could I be liking this?! I tried to wiggle my ass, both to stimulate my cock (I hadn't cum in two days) but also to find a position where the stretch would be less intense, but nothing worked. If anything the stretch felt bigger.
"Hear that clicking sound boy?" Jay asked. Now that he mentioned it I could hear an occasional click in the background that coincided with me moving my ass. "That's the ratchet strap attached to your balls. The more you struggle, the tighter the rope gets... I'd think very carefully about just how much you want to move around. Unless you want to be known forever as lowhangingpussyboicunt!" With that he guffawed, evidently very happy with himself.
"Now, I've had a long and tiring day so I think it's time to get some shut eye." As he moved to turn the lights off I immediately wondered where he was going to go to sleep. There was only one bed in the room and I was spread eagled over virtually the entire thing. There simply wasn't enough room for him to lie alongside me, but surely he wasn't going to sleep on the sofa?
"Time to get comfortable Bobby" he said. I felt his muscular body climb onto the bed and then his knees straddling my upper legs. A second later I cried out as his hard cock penetrated my hole again, before I felt the full weight of his body lying on top of me. Seriously? This was where he was going to sleep? On top of me with his dick in my ass?!
It was then that the full deviousness of his ball stretching parachute became apparent. He wiggled his body around, trying to find the most comfortable position. The more he moved the more his body acted as as a painful fulcrum for his dick. I was literally being reamed out. And of course if I moved with him to take the pressure off my ass I would pull my balls off.
Jay finally settled in one place. "How do you feel boy? I bet that feels good, eh?" It was entirely a rhetorical question as he went on talking. "You may have noticed that my cock is deep inside of you" - no shit Sherlock! - "it's your job to keep me hard. If you feel me going soft it's your fault and I will blame you. I want you to use the muscles in your ass lining to massage my cock back to full hardness. Can you do that for me Bobby? Why don't you try it now? Come on, let me feel it... your future here relies on your ass muscles being nice and strong, so this is great practice I'm giving you."
Mother of god. A beast of a man was lying on top of me, my ass was overstuffed with cock, my balls were stretched to hell AND I had to keep him hard all night long?!
"Come on, let me feel those pussy muscles ripple" Jay said, painfully pushing his cock deeper between my ass cheeks to make me comply. I had no choice and squeezed my hole tight, then released and repeated. I could feel Jay's dick twitch with pleasure.
"That's right bitch, you just keep doing what you're doing and keep me hard. If I wake up in the night I'll want to fuck you again so you've got to keep me ready and primed. Don't fuck this up boy... or you really will be fucked up. Sleep tight cunt!" With that he nuzzled my neck ever so slightly, and then I could slowly feel his body relaxing, his breathe calming down and Jay gently falling asleep.
The rest of the night was deeply uncomfortable. Jay was heavy and even though I was bushwhacked after the last few days and needed to sleep I was frightened of drifting off. Keeping Jay hard took a lot of my energy, but it also gave me a lot of time to think. I felt like I was living my worst nightmare, except I'd never had any nightmares this crazy. To be kidnapped by a bunch of sex-crazed animals who seemed to have only one purpose in life -- to turn me into a `pussyboicunt' -- was unbelievable. I didn't want to think what it actually meant. Maybe if I blocked being turned into a pussyboicunt from my head it wouldn't actually be happening to me? And yet in many ways, I could feel it happening to me. I could feel Jay's cock buried in my hole. I could feel the reaction as I squeezed my ass muscles, his cock pulsating and returning to full hardness. I did that. Me, Bobby Kent. I made Jay hard. Maybe this was my purpose in life?
Inevitably I drifted off, it was impossible not too. But I soon woke to extreme fire in my hole! Regardless of my failure to keep Jay hard, his regular morning wood must have done the trick of returning him to full pussyramming size. And he was fucking me brutally for failing in my `duty'. What made it brutal? Whatever lube and cum had been in my ass yesterday must have completely disappeared and I was being fucked dry. It was agony. Jay didn't say much, this seemed to have turned into a grudge fuck for him and he mechanically kept going until he shot his load.
"There you are bitch. I see we're going to have to invest a lot of time in your muscle control and your ability to follow orders. Anyway, here's a little present for not doing what I asked you to do..." he said with a contented sigh.
Fuck! My hole suddenly felt scalding hot... the bastard was pissing in me! He was filling my guts up with his morning slash. By now I was used to taking enemas and cleaning myself out but his flow seemed to go on forever. It was so demeaning. Tied to the bed, my balls in agony (I had done my best not to struggle, but that doesn't mean my balls weren't numb with pain) and a bastard lying on top emptying his waste into me. Is this my future? Because if it is I'm fucked.
Jay eventually pulled out and climbed off. He told me in no uncertain terms to hold the piss inside until I was untied, that he didn't want to see me leak a single drop. I clenched my ass cheeks until I thought they'd burst. Being untied was such a relief, except for the blood rushing back into my ball sack as they were released. God knows whether they'll ever go back to normal - they look purple and angry.
Jay lead me to the bathroom and took me to flush myself out, and to make sure I used the enema nozzle. There it was again with it's crazy light at the end of the tip.
As we ate some breakfast Jay explained the day ahead. "Big day for you Bobby. Your first day of the program... in years to come you're going to look back on this moment and see it as life-defining." He went on in this vein for quite some time. To be honest I wasn't in the mood to hear it. There are only so many times that I can hear this shit, especially from a bastard like Jay. I think my only strategy is just to roll with it and try not to be controlled by it. They can change my hole, but they can't change who I am on the inside, right?
We got to the end of the meal and Jay told me to write this up before he took me to meet my first `tutor'. God knows what the day has in store. Anyway, here he comes now to lock me back into my cock cage and take me to my first lesson (I didn't cum last night by the way, through I'm pretty sure the bed was damp with precum run off). I'm sure I'll have to tell you all the lesson later...
Later. First dildo lesson
So much has happened today that I can't believe it. I feel as if I'm standing on the edge of a precipice and all the tutors are standing around waiting for me to fall. I've just got back and Jay wants me to sit down and write this up immediately. As per his rules, I'm naked and masturbating, though right now it's not the motions in my hand that's making me twitch, it's the sensations from my ass. My hole feels so big... I honestly believe it's been changed forever - christ, I've seen the evidence! - and I'm only one day into the program.
This morning Jay delivered me to a large room that I can only describe as being halfway between classroom and sex dungeon. Instead of rows of desks there were a variety of beds, padded benches and what looked like barbershop chairs. Instead of posters of kings and queens on the walls there were the most graphic and hardcore instructional diagrams about the art of man-on-man fornication you could ever possibly imagine. It was like an explosion between a Mapplethorpe gallery and a technical drawing seminar.
The walls were painted black and there were no windows. The floor was covered in some kind of thick and spongy matting and instead of the room smelling of bubblegum and stationery, it smelt of lube, latex and ass juices. However, this was nothing compared to the most intimidating feature: an entire wall - all 10 metres of it - covered floor to ceiling, wall to wall, with shelves lined with hundreds upon hundreds of dildos. I was a novice when it came to all of this - my only past experience being the dildo I'd found under the bed in my sister's room - but this was simply staggering. This wasn't a mere sex shop of dildos, it was a dildo encyclopaedia. Every size, colour and shape appeared to be represented. And it wasn't just the sheer number available that intimidated but the giant girth and width on display. Even the most cursory glance was terrifying.
Standing in front of this arsenal of toys was my tutor Trent, who seemed mighty pleased to have a new student. He was a tall black man with smooth skin and a completely bald head. He was very striking looking, not least that he was wearing some kind of black neoprene jeans and vest (apparently at the end of the day it was easier to clean all the surplus lube off neoprene than leather or rubber). The vest revealed his taut stomach, broad chest and made the most of his defined arms (I guess it was pretty easy to get lube off bare skin too!).
Jay introduced me. "Trent, here's the new pussyboicunt as promised... Bobby, say hello to Trent... He's going to be your personal anal stretching therapist. By the end of this month you're going to know him very well. Intimately well. So, I'll let you two get started..."
With that he left and so began my first lesson: introduction to dildos. To say it was a lesson is a bit of a misnomer, as it was actually a one-on-one tutorial. Just me and Trent together for 6 hours totally focused on my hole. And to say it was an introduction is a bit of a lie too: even in my inexperience I knew that the choads and dongs he used on me were way past introductory size.
Trent started by trying to ease me in gently. "Welcome Bobby, congratulations on being selected... You won't believe how many guys fight to be in your shoes, so well done, it's a huge achievement. I'm going to make sure you don't regret your time here and that your hole never forgets either..."
"Never forgets? What do you mean?" I asked hesitantly as I looked at the wall of dildos. I felt this was the moment when I could finally understand exactly what the next month - this `program' - was all about.
"It's simple boy, once you've spent some time with me you ain't never going back... you're permanently transformed. That's what being a pussyboicunt is all about! I can see you eyeing up our toy selection, maybe I can walk you through them and broaden your horizons a bit?" Trent beckoned me to follow him and strode over to one end of the dildo wall.
"You see, the toys in this section are all about opening guys up. The material is soft and spongy, and regardless of the size they all have a similar profile. A flanged head that then gently increases in width. As the male phallus is such a good method for breaking holes in, many of these toys take inspiration or have been directly moulded from human cocks." He was right... all the toys in this section did fit that profile, yet I couldn't understand why they ranged from the toy in his hand (which I would equate to `well-hung' now I'd met Carl and Jay) to dildos of freakishly impossible sizes.
He had obviously done this spiel many times before as he anticipated my question. "You may wonder why they're in so many different sizes... well the truth is that it doesn't matter what size the hole, it still needs opening up every so often. Today you're one size, but in a week's time your hole might be this big..." at this he gestured to an extravagantly sized dildo whose size defied belief to my eyes. Jesus Christ, he thought that expansion was possible in a week?!
My look of disbelief didn't seem to slow him down as he moved on to the next section of toys. "Now, from openers to stretchers... All the toys in this section are designed to really force a hole wide. All these will really supersize a hole, no matter what the starting point is. See how the heads are often deeply flared and then gently shrink down before widening significantly towards the base? It's all about getting these toys in past the head, letting the hole relax and then really taking advantage of that stretch to flare the cunt out. Honestly, you can do some good damage with these..."
Damage? Fuck me. Trent seemed really pleased with himself and totally oblivious to the way I was feeling. Without pausing he walked further down the wall.
"Now this is the wrecking section: all toys designed to fundamentally change the properties of a hole. We're talking from hole to pussy, cunt to cavern... All of the dildos here are made out of firm latex or hard silicon to give a really punishing and unforgiving stretch. Each one is designed with destruction in mind. Like this rough rider, with these raised half inch dots along the shaft... it may look simple but it's excellent at giving a hole really puffy pussy lips. Or this one with the mean punch cutter of a head and then a razorback shaft of graduated flanges in increasing sizes... No matter what the your hole size you're going to know about it once you take one of these."
Jesus Christ, I couldn't believe what he was saying or what he was showing me. Until now I had valiantly held out hope that whatever these fuckers had planned for me was reversible, that somehow I could go back to a normal life afterwards. But this wasn't normal... on no scale at all could these toys be described as normal. Any one of them would take me past the point of no return, to permanently being a complete pussycuntboi... whatever the hell that meant.
Trent ploughed on regardless. "And here's the final section: the saboteurs. These are dildos so big that they ruin a hole for anything that comes next. Nothing can compete with these fuckers." The size and shape of these toys staggered me. It wasn't just that they were inhumanly large, it was also that they simply weren't human. Most had clearly been modelled on animals and mythical beasts. Which sick fuck had the imagination to be able to design toys this fucked up? Toys that had only one purpose in life: to conqueror and annihilate any hole they touched?
By now Trent was unconsciously resting his hand on the giant, bulbous helmet of a truly demonic looking toy. The head was thick and shaped to cleave open a cunt... before the shaft - covered in brutally thick veins - dramatically widened to make sure no fuckhole ever came back in one piece. Trent saw the mad panic in my eyes. "Don't worry boy, I would never start a session off with a toy this big. Well, at least not today... Now, I don't want you to confuse my area of expertise with this wall of toys. I want to make it perfectly clear that I am not an expert in toys, plugs or dildos... No, I'm a certified expert in hole stretching and that's my job: to stretch your pussy. These toys are just the instruments of your destruction. I'm here to take what you laughingly call your hole and turn it into a real man's cunt."
"But Trent, I don't want a cunt. All I wanted was to lose my cherry, the last thing in the world I want to be is a mancunt." I replied immediately. The dildo wall may have shook me to my core, but maybe if I projected confidence I could desperately get out of this situation. Pleading was my only hope.
"Don't bullshit me boy, I saw the video of you pulling train. There's no way you'd be standing here in front of me if you didn't want it big time. Besides, I didn't say mancunt, I said man's cunt. That is, cunt that belongs to a man. In this case you are the cunt and the man who owns you is Jay, though don't expect it to stay like that forever...
Now... why don't you go and pick a toy that you think you'd be comfortable to start the session with? Take your time and have a good look... but maybe stick to the openers section for now, eh?" With that he laughed and walked back to the beginning of the wall, clearly expecting me to follow. My shoulders slumped... there was no way of getting out of this.
I resolutely scanned the opener shelves, looking for something similar to the size of the toy I had played with before in my sister's bedroom. To be honest I found it difficult to find anything that small, and having had intimate experience of Carl, Jay and the fuck train 30, I could see why. What I had played with was nothing in comparison to the hung guys here.
Eventually I settled on a reasonably slender black dildo a fair bigger than my own 6" cock. I had to start somewhere right? I guess this one was about 8" long and a lot more girthy than mine. I was worried that Trent might think it was too small but he didn't seem to care. He took the toy from my hand and reached up with his other to grab another from two shelves up. "Okay, good starting point boy... but this is what you're going to be able to take by the end of today." It was uncanny how he seemed to know exactly what toy he wanted, almost without looking, but I couldn't help but think he had made some kind of mistake. The toy he'd grabbed was fucking huge! It was dark blue and was semi-realistic with a pronounced head and then a thick shaft descending to a giant set of balls.
"So, this is Thor, made by Crackstuffers. It's nearly 3" wide and 13.5" long, though only 10 of those are insertable. Well, not unless your arse is so hungry that we can sink these life-like balls into your hole. Wouldn't that be a thing, eh?"
I was gulping in disbelief. How the fuck could I fit a toy that big inside of me? I mean yes, Carl was big, but not that big.
Trent completely misread my facial expressions. "Don't be upset at how small it is, kid. I should be able to plug a guy your age with toys twice this size without even a grunt, so don't go complaining to me that you didn't fuck yourself with bigger toys before you arrived at the School. It's not my fault you're late to the party... Now, let's get you secured."
At this point Trent lead me over to one of the barber shop chairs. I wanted to flee - to escape from this hellhole - but where could I go? The School was a maze of sex, with tutors and attendants at every turn. And Trent was much stronger than I was - I bet he could wrestle me to the ground with just one arm.
He gestured towards the chair. The metal frame was the colour of gun metal, the seat padded with worn, dark brown leather. The chair seemed very high off the ground, but its defining feature were the metal attachments fixed to the base. I may have been a virgin before I got to the School, but even I knew that they were stirrups to hold my legs apart and raised in the air. I suddenly realised why the chair was so high - once I was seated and spread the height would give Trent perfect access to my ass.
I gulped and climbed in. Trent helped by positioning my legs in the stirrups before wrapping leather straps - built into the chair - around my ankles, thighs and chest... Even my forearms and wrists were secured. I was now held captive for the day.
And so it began as he started feeding my hole with dildos. He started off with the thick 8" toy I had selected from the wall, which in comparison to Thor was laughably tiny. Trent lubed it up and wasted no time in getting it inside of me. To be honest I was surprised at how easily I could take it. Trent explained that the toy I'd picked was about the limit of most girl's cunts, but the School was obviously aiming to get me much bigger than that.
Soon he had grabbed another toy from the wall, and then another and another. All of them were slid, cajoled or forced inside of me. There were simply too many for me to list... Though I do remember Trent describing a thick 9" choad as the kind of toy that only `pro' gay men would feel comfortable with. I grunted and heaved as Trent plunged it into my hole.
Little by little Trent was stretching me open. Even before I'd got to the next toy - a thickly veined dong that Trent said even most rent boys would have trouble accommodating - I began to appreciate just how skilled Trent was at his job. He was using a mixture of force and persuasion. Giving my hole just enough time to adjust before pushing that little bit further into my pussy. That's how he kept on referring to it, my pussy. At one point I heard him say "come on Bobby, I know your pussy can take this. This dildo is almost the same size as the biggest guys on your fuck train, and you took those cocks with ease. If you can take those, then I bet your pussy can take a little bit more of this fat stalk, yes?"
The barrage of toys and words kept on going. It was relentless. Trent didn't stop once and there was barely a moment when I didn't have something inside of me. Said he didn't want to give my pussy a chance to close up. Not after he'd made so much progress.
Every so often he would pause with an imitation dick buried deep inside of me, filling me more than I could ever have imagined. Trent would look me in the eyes and tell me to enjoy the stretch. That's it, nothing more... Just enjoy the stretch, bitch. The more he said it, the more I believed it. The sheer feeling of being full was amazing, like nothing I had ever experienced before. A deep, twisted part of me beginning to be proud of just how much I was taking. Christ, I'm sick.
Finally, after hours and hours of effort, Trent pressed the mammoth head of Thor against the lubed mess that was the entrance to my ass. Even with all the prep and build-up, it was still a gigantic task to feed my pussy with a toy that big. Trent said he believed in me but I couldn't believe how a toy that big could fit inside of me. It felt like a bludgeon to the most intimate and sensitive part of my body. No matter what I said, no matter how much I protested or struggled against my leather bindings, Trent kept the relentless pressure on my pussy.
Eventually my hole caved and gave way. It had to, Trent was simple too strong and his desire to see the giant rubber dick in my hole too great. He may not have been fucking me with the toy (thank god!) but there was no doubt he forced that fucker inside me. The stretch was unbelievable, my entire body centred around the foreign object in my butt.
Trent smiled at and looked me in the eye. "There, there, Bobby, you've done really well. I'm proud of you." Despite the all-consuming pain, a little bit of me felt proud too. I had done it, I had taken this epic toy and survived intact. Sure, my hole must be bigger now, but I was still in one piece. I was still Bobby Kent and not Bobby Kunt. My happiness was soon thrown overboard... "Just think, now you've taken Thor we can really start stretching your pussy!" he said with a demonic smile.
"That's for the future though... for now let's get you cleaned up. Jay will be back to collect you soon." With this he grabbed Thor by the balls and slowly removed the dildo from my arse. For the first time in hours my hole was empty and Christ could I feel it. I felt incomplete... as if something fundamental to my body was missing. Trent put the rubber cock down and stood back to admire his handiwork. "Wow boy, your hole is looking good, even if I say so myself! Nice beginner's gape too... really gives me something to work with."
Gape? What the fuck did he mean? So many times over the last few days I felt as if there was a huge part of my vocabulary that was missing. Sex education at school, the locker room, the vanilla porn I'd watched... none of it had prepared me for this.
Whilst I was trying to work out what he meant, Trent approached my hole with an enema hose. Once again the nozzle lit up, but this time Trent said it was loaded not with water, but with a medicated balm that would soothe my hole as it flushed me out. I've got to say that it felt amazing - warm and calming. I soon forget all about my knowledge gap as the lotion somehow managed to relax my entire body.
Soon Trent removed the enema nozzle and released me from the chair. I was a little bit unsteady on my feet, but it felt great to be standing up again. Even with the balm I couldn't deny that that my pussy felt entirely different though. Trent had spent so long stretching me that it felt as if there was still something inside of me, like a phantom dong or something. I wondered just how long it would take for that feeling to go away. I noticed that my jock, distended from the cock cage, was slick with precum. Damn, my hole must have really enjoyed Trent's ministrations if I had leaked that much. Surely it was wrong to enjoy all this?
Just at the point of feeling most shameful, Jay entered the room. He seemed happy to see me both on my feet and looking bashful. He immediately asked Trent how I had done and whether I had made good progress. Schucks, thanks for asking me whether I was okay Jay.
Trent replied "why don't we take a look?" and picked up a tablet computer. He touched the screen a couple of times before the large TVs dotted around the room flickered into life. Here we go again I thought, another video montage of one of my sessions... but no. This was entirely different. This was some insane 3D representation of a body -- my body! -- and the camera was flying towards my ass. How the fuck were they doing this?
"So this is Bobby's pussy before he arrived for the session this morning. Note the slight corrugation of skin around the entrance and the overall pinkness and inflammation. I presume you kept him cunted all night long?" said Trent as he looked towards Jay, who nodded. "Yeah I thought so. Nice touch, it definitely helped... Now lets fast forward to just a couple of minutes ago."
Fucking hell. The image on the screen was monstrous. I mean I have never seen my arse before up close but I knew what a regular one looked like. I had been disturbed at the first sight of my used hole, but this second image could only be described as horrific!
"Notice how the pussy is beginning to turn itself out. You can just start to see the beginnings of his cunt lips... but I think most impressive is his gape. When I took this image it was a half inch across and pulsating quite happily, searching for his next cock or toy I bet!" they laughed.
So that's what Trent had meant by gape. My poor, precious hole was gaping open... "What the fuck have you done to me? And how the fuck did you get that image?" I cried out.
"Calm down boy, you haven't made anyway near as much progress as you think you have" said Jay. "This is all very straightforward. Every time you use one of the enema nozzles it takes video imagery of your hole. That's why it has the lights at the end. It's pretty nifty, see? We can look at the development of your hole since you arrived--" Jay nodded at Trent who played a slideshow of my ass starting off as a regular puckered boyhole to the degraded mess it was now "--and the camera even allows us to see inside your body to get an inner look."
The screen changed to a 3D model of the inside of my ass. To be honest I had no idea what it should look like, but all I can say is that it started off looking like a reasonably tight tunnel and could now only be described as a cavern. I was gobsmacked.
"We call it the cunt imaging system, CiS for short. Pretty cool eh? Looks like you've still got a long way to go yet though boy."
And with that I was led back to Jay's room. I feel exhausted and traumatised. I'm naked and sitting at this crummy desk doing this. It's fucking hard to keep myself hard whilst writing this shit. It's sick. Jay says it's exercise time next and then I guess it will be another night with his cock inside my pussy. Sigh.
Next: Bobby takes his first double...
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