Day 7. Cock and toy worship
Themes include big dicks, cock sucking, dildo fucking, toy challenges, plugs and domination. Average reading time: 15 minutes.
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That was the most uncomfortable night of my life. If I'd thought that having Carl sleep on top of me was tough, sleeping with my hole prised open all night long by a hard, inflexible hollow butt plug was nearly impossible. None of the cocks (and dildos) I'd taken in the last 6 days had prepared me for the misery of being stretched out non-stop.
Neither my mind or my body would let me fall asleep. If I wasn't lying awake staring at the ceiling and thinking about how my hole was being permanently reshaped, then my hole was keeping me awake as powerful (and painful) ass spasms desperately tried to eject the plug and tighten back up.
At one point I couldn't help but explore the edges of the plug (and the harness that locks everything together) with my fingertips. I was pretty shocked. The plug has a big flange which means I can't touch my hole, but what I can feel are the edges... which feel really puffy and swollen. God damn. Those are not words that any guy my age should ever have to use to describe their backside.
However, I must have drifted off to sleep eventually because in the morning I was woken by Jay's giant cock in my face. He must have climbed astride me in my sleep, and was now using the position to wipe the juicy tip of his morning wood across my mouth, cheeks and nose - leaving slimy trails of thick precum behind.
At this point I thought that this was some kind of sick hazing ritual or just one more way of humiliating me further... After all, my admission banned me from taking dick orally. Having said that though, I couldn't help but involuntarily pant for his dick - the amazing combination of heat from its thickening shaft, the musky smell of heavy, overnight ball sweat and free-flowing precum was pure intoxication.
The stimulation on Jay's cock was obviously having a good effect for him too, as his dick got thicker and harder. Actually even his flaccid prick was monster thick, but now it was fully erect it was often blocking out my view of his face. When I could see past it though there was an evil leer creeping across it. I knew that look... I was about to get fucked and this was the warm-up.
I was completely wrong: this was the unexpected main event.
Seconds later Jay rested the tip of his dick against my half open mouth and said "that's right bitch, if your tight hole is too worthless for my dick, then your face cunt is the next best thing! I don't give a fuck that you signed up to a nil-by-mouth cock diet, I need to nut!"
Before I had a chance to think -- I hadn't signed up to any of this shit you dickwad! -- he was holding my head in place with his hands and feeding the massive girth of his cockshaft into my slack-jawed mouth. Thank god he was going slowly (for Jay at least) as in my entire life I had only sucked off one other guy, and he had a thin cock at that. This was in another league and completely filled my mouth full. Inevitably, as the inches pushed deeper I could feel my gag reflex beginning to pulsate...
"Breathe through your nose bitch, breathe... My cock isn't going anywhere except down your gullet so you better get used to it!" However it was clear that he knew the burgeoning limits of my throat and backed off ever so gently, just a smidge for me to grab some air. Even so, he didn't lose much time before I felt the immense pressure of his helmet on the back of my throat again.
Despite the challenge of deep throating his dick, I've got to say that the sensations in my mouth were fucking amazing! The thickness of his fireplug cock completely filling me. The taste of his precum and the sharp tang of whatever sexual conquests Jay had plundered the night before being reactivated by my salvia. (Jesus! I can't believe I've just written that!) The warm texture of his skin and the veiny shaft wrapped around my tongue. The smell of his ball sweat filling my nostrils and his pubes tickling my face...
But above all, the sheer strength imposed on me by a powerful man implanting the life-force of his genitals directly inside my face. I could feel his hold over me; that I was servicing his needs. It was spellbinding, all I wanted was more of his dick. I groaned and moaned in appreciation, anything to signal that I wanted more. That I could take it.
Jay obliged in spades. He slowly built up from letting my mouth adjust to the gigantic size of his dick to a steady face fucking rhythm and then to a full-frontal, balls deep, face-fucking attack. I guess I should have known from his ass-fucking style that this would also be brutal. My eyes watered and I could barely keep up, but all I knew was that I wanted more. I wanted Jay's load.
It didn't take long before his long-dicking strokes morphed into shorter and more urgent thrusts. He was grunting and getting faster... Christ, this fucking cock cage! Jay got me so used to wanking whilst writing and now I'm on full lock down. My dick is fighting the metal tube so badly it's painful!!!
Anyway, he came! Man, did he cum. He'd pulled back his dick a good few inches to position his meaty head on my tongue - I guess so I could taste every drop. Who said Jay wasn't a considerate fucker?! However, the first volley of spunk shot into my mouth so hard it splashed off the back of my throat and overflowed my lips, cascading like a waterfall over my chest. Even then he kept on cumming, pumping volley after volley of thick tangy goop into my mouth. I was forced to swallow just to breathe. Not that I'm complaining though, it tasted fucking delicious. The essence of power.
And then it was all over. He withdrew his cock and it deflated in front of my eyes. In fact, I'd never seen Jay's cock lose it's erection so fast. For such a cocky bastard, he was suddenly incredibly quiet and withdrawn, almost sheepish. I didn't know what to think, and tried to say just how much I had loved swallowing his load, how lucky I was to be rewarded-- but he cut me off. "Stop Bobby. I can't deny that wasn't good for me too, but we can't speak of this again. You got it? Never. Understand?"
He looked so apprehensive and stern that I quickly nodded my agreement. I could feel that the memory wasn't going to leave me quickly though. Sucking Jay off had reminded me just how much I liked dick in my mouth, and just how great cum tasted. I wanted more.
He climbed off my body and directed me to the bathroom for my enema hose-down. Once again it felt hugely demeaning but... He then sent me off to my next lesson with Trent. I was dressed in my powder blue locked t-shirt and my jock/plug harness. I had cum in my belly and all my thoughts were of wanting more cock in my mouth and wanting the plug still wickedly stretching my hole out.
The bench
As soon as I arrived I knew that this was going to be a very different lesson compared to the previous days. Nearly all of the furniture had gone - the stirrup chairs and mattresses cleared out. All that was left were a couple of very long, black, padded benches, each one studded with dildos every metre or so. Just before each toy was a metal grip of some kind - an upside down U rising from the bench about half a metre in the air. The toys and grips ran the entire length of the room, so even at a glance I knew that they must be at least 10 toys on each bench...
Trent was standing in the middle of the room, and expansively waved me in. "Today we're going to do something very special: bench fucking" he said. Looking around I understood exactly what he meant: the bench nearest to me looked to have all the dildos I was so familiar with from my last two lessons arranged in size order. It was obvious that I would have to take each toy in step and that the metal hoops were handles for balance. That didn't stop Trent from mansplaining the day to me. FFS
"The challenge is to squat and fuck yourself onto each toy in sequence. You may of course recognise some of the toys we've used so far, but there are also a fair few new ones I've added from the wall..."
However, it was then that things got a little bit more complicated. I should have expected the School to make things tougher then they needed to be.
"These may all look like the regular toys you've used before but in fact each one has had a significant upgrade. All of them now have a cock tube running up the centre of the toy connected to a heavy-duty lube pump. This means they're all self-lubricating and will never dry out, no matter how hard you fuck yourself.
In addition, each one has a set of sensors built in to the shaft. This tells the computer--" (he nodded towards a large digital counter at the end of the room) "--just how much of the dildo you've inserted..." I must have been looking pretty perplexed as he ended by saying I would pick it up pretty quick as we went along.
He gestured to the first bench, the one with the toys from my last lessons. "Let's start at the beginning and work your way up. I want a clear 25 strokes on each toy, you hear?"
I knew what was expected of me, but before then I had to speak to Trent about yesterday. I was plugged with a brutal stretching device because of him and his fucking rectum `tightening' cream. As far as I was concerned my massive discomfort was all his fault. My protestations were laughed away. "Sorry Bobby, I should have said that the cream may have unintended consequences. Maybe it's a good thing though? It sure means you're going to ace today's lesson! Christ, I bet you're stretched out like a wind tunnel right now..."
With that he came towards me and unlocked the harness holding the plug. With a sharp yank (and a loud fart from me) he pulled the plug out of my distended hole. Christ, did that make my eyes water! My hole immediately felt barren and empty. And open. Oh my god, so open. I could feel the overstretched muscles in my pussy trying to contract, but my hole could barely collapse in on itself.
I had no time to think before Trent told me to get going and he led me over to the first bench. "Right. 12 toys in size order, 25 strokes on each one, in your own time. Go!"
I squatted over the smallest toy - the one that I had selected at the beginning of my first lesson. To be honest even to my novice eyes it now looked like a micro-toy, so puny was it compared to the others. And Christ did it feel puny when I lowered myself down. I could barely feel it inside of me. I'm not sure it even touched the sides! I was so surprised that I lifted myself off it. Immediately the room was filled with a loud gameshow style `EH-ERR!' noise that startled me.
"That noise means you didn't complete a full stroke. Try again" said Trent.
I lowered myself down, this time bottoming out on the bench before lifting myself all the way up. This time a satisfying `pock' noise sounded and I could see the big counter at the end of the bench light up: 1. I had the hang of this and I started fucking myself on the toy, pock, pock, pock... this was easy.
"By the way, don't get complacent. If you don't bottom out and ride the full height of each dildo your score will start going down. An incomplete stroke doesn't count and you'll just end up having to fuck yourself even more. You want to get all the practice you can get with these easy toys."
By now I was on the fourth toy and I began to see what he meant. The squatting was actually fairly tough (thank god for that circuit training!) but it was the shape of the dildo that made the real difference. I could already tell that those with a pronounced helmet were super tough to easily ride a full up-and-down-stroke each time.
That wasn't the biggest problem though. The more that I progressed the less I found I could focus. Surrounded by all these imitation dicks and yet all I wanted was one flesh and blood cock. Jay's cock. In my mouth. And his thick glorious cum. No matter how hard I rode, my mind kept on coming back to his dick in my mouth.
Trent could tell that I wasn't all with it. The eh-err' buzzer keep on going off and I had to keep on making up lost' strokes. He started getting angry, telling me to pay attention, that all this should be easy for someone at my `stage'. I tried my best and put all my energy into the last few toys. It was really hard work. Yes, the big toy Choad was still ahead of me but the last few leading up to it had gigantic helmets before really narrow shafts. A full stroke was a punishing stretch over the head - a real meaty pop! - before sinking down a slowly widening shaft... Of course on the way out my hole would clamp around the helmet flange and it took a lot of effort to pull free, no matter how much lube was sliding around.
The time between pocks got longer and longer. I was definitely beginning to feel the burn in my legs and the stretch in my hole. Finally, agonisingly, I made it to the end - 300 strokes on 12 dildos. I was dripping with sweat and my tank top was soaked. God I was exhausted. After that punishing ride it was no wonder that all I could think of was that sucking Jay's cock was infinitely more pleasurable.
Trent let me rest for the briefest of moments before telling me that now I had the hang of it I could move onto the more advanced bench. At this I looked around at the other line of dildos. Up till now I hadn't paid the second bench much attention, but when I took a closer look it was obvious that this collection of toys was way more hardcore. Tough, awkward shapes that would be the very devil to take. Some of them looked as if they had been based on animal dongs, others on aliens or mythical beasts. And was that a... arm stump over there? WTF?
Trent told me that I had to do another 25 strokes of each toy, but that this time the computer would decide in which order I had to ride them in. Something about the toys having the same clutch sensors as the stretching plug, and that the computer would optimise the order in real time for the most effective stretch... I didn't have time to take it on board before Trent hit a button on the counter board and I was off: the fifth dildo along - a short, black and very wide toy with tons of bumps and humps - lighting up and commanding me to ride it.
It was fucking tough. And intense. I was moved up and down the bench, seemingly in a random order, but I'm sure to some twisted masterplan. Going from toy to toy in completely different sizes made me realise just how loose my pussy was getting (something I wasn't so aware of when working up in size order on the first bench). Some toys felt more slack than others, though I still feel the general shape and girth of each dildo - I've evidently still got some clutch!
My mind kept on wandering to the taste and smell of Jay's cock though. I'd never signed up for hole training and all I came here for was to lose my virginity. Tasting the flesh of Jay's prick reminded me of how low I had sunk and that I didn't want to be here, riding inhuman toys till hole oblivion came. Jay's cock though? Jay's cock was--
Trent broke my reverie by clapping his hands. "Come on bitch, focus!" he shouted. "You're not putting your back into it! You're only on the fourth toy and given your speed on the first bench you should be on your seventh!" he shouted. (Never mind that the first bench was much, much easier than this one. Git!) "I'm switching things up a gear."
Even though I was mid-plunge on a thickly veined red animal cock, he hit a button and the counter reset to zero. "From now on the computer is not only going to be deciding in which order you ride the toys, but also the number of strokes and just how long you've got to do it. This is going to be a real roller-coaster of a pussy ride! Don't forget that the full-stroke rule still applies, except now you'll have two strokes deducted from your running total for each broken stroke. Given your performance so far you'd be in minus numbers by now so you better look sharp boy."
My body slumped. I was still half-way impaled on the animal pussyrammer I had been riding. I'm just not sure I could face this anymore. Trent could sense my defeat but wasn't having any of it. Suddenly I felt a huge jolt in my arse and I leapt off the toy in shock and pain!
Trent cackled, the bastard. "Oh yeah, didn't I mention? Stay too long on a toy and you'll fucking know about it!" The sensors and gizmos in each toy must be able to deliver an electric shock. I had just been electrocuted! I stood there in disbelief at this fresh hell before Trent clapped his hand again. "Better get started bitch. The longer you wait the higher the voltage goes!"
Fuck! I could see an illuminated toy in front of me and I raced over and furiously started bouncing up and down on it, resigned to my fate... And so that's how my afternoon paned out. Jumping from toy to toy, bench to bench, just existing stroke to stroke. Even with the threat of being shocked it was fucking tough keeping up with the sheer variety of different shaped and sized toys. Sometimes I had to ride a toy for just one stroke before moving on, other times 20, 50 or even a 100 strokes. I began to think that the computer was inherently evil and out to get me... The afternoon was punctuated with pocks, eh-errs, cries of pain and frantic countdown music to continually drive me on.
All the while though I couldn't help but think of two things. Yes, Jay's cock... but also the sheer degradation I was going through. Previously Trent had dildo fucked me with these toys, but now I was the one doing the fucking. I was forced to gut myself on toy after giant toy. Even though the computer was in control, I felt that I was the one responsible for this session, that I was the one stretching my hole, not the School or the program.
I tried my best, I really, really did... but I just couldn't keep up. I was too distracted, too damaged. Again a shock coursed through my hole and I flung myself off the toy with such force that I collapsed into a foetal position on the floor. I was in tears of despair before I had even hit the ground.
Trent came over and helped me to a sitting position. It was good to feel someone's arms around me, however briefly. He took a moment and then asked me what was wrong, that he knew the program was demanding but that I should be able to handle it...
My emotions crumbled. I couldn't hold back. I told him how tough I was finding it... and I told him about this morning's blow job. About Jay's mouthwatering cock and just how much better flesh is over these rubber rejects. About how I had been craving the taste of cum all day... How I wanted more than just an imitation cock in my arse. It was embarrassing but it was good to let it all out.
"Hmm, I see..." said Trent. "Well, I can't say that I agree with what's happened here. It sounds like an intolerable distraction and clearly something is going to have to change. Let's end the session early and I'll go and see what I can do about your cumlust... Till then, let me replug you. Hopefully today hasn't been a complete waste of time."
Fuck. I had forgotten about the stretching plug.
Trent grabbed the one I had been wearing when I entered the room. It seemed small in his hands, especially when compared to all the toys that had been inside my ass today. He lined up the plug with my hole and pushed it inside... Damn. There was barely any resistance and almost immediately it let out an angry, high-pitched whine.
Trent quickly pulled the plug out. "Ah! Good job. At least you've made some progress. Time to go up a level." He wandered off and came back with what I guessed must have been the next size up, even though it looked much bigger in his hand.
For the second time today he pushed a plug against the mashed up entrance to my ass. This time I could feel my body pushing back though - there was resistance. Trent couldn't help himself... it was the first time he had been close to my hole in 24 hours and obviously he wanted more. He pushed the plug in a bit and then pulled it back, in and out, a little bit further every time. He was literally plug fucking me.
Eventually, despite the evil and hard shape, Trent rammed the plug so far into my hole that my ass muscles sucked it inside. It felt fucking huge, my pussy spasming around the hard core and desperately being prevented from closing.
"Fuck Trent, I don't think I can take it! I feel like I'm going to burst!" I cried out. He hands were still down at ass level and I hoped he'd gently pull the plug out. Not a chance though, he was actually locking the plug to my harness! "I know Bobby, that's the idea. Jesus, how stupid can you get?" he said. "Anyway, you should be thanking me. Your old plug felt so slack in your pussy that I jumped ahead a few sizes! That fucker should keep you company for at least a couple of days. After all, we don't want your hole retreating in size, do we?"
I felt mortified. Just how big was the evil thing inside of me? Trent told me to take some deep breathes and that I'd soon get used to it... Yeah, right. He left me alone and said he'd be back once he'd spoken to some of the other tutors.
I wobbled around the room, my legs aching from all the squatting and bandy-arsed from the bench action and the plug inside of me. As I looked upon the lubed up remains of the toys I'd been savagely riding all day I had high hopes that my program could be changed or upgraded. Surely liking cum can't be that bad a thing?
It turns out it was.
About fifteen minutes later the classroom door opened and Carl entered. Carl! My cherry taker and the man I felt was my safe haven in all this mess. My mind raced... was I going to get to suck HIS dick? OMG, OMG!! Please let this be true!
All he said was "come with me boy" and held the door open. I slowly - out of necessity - went through it and followed him down the corridors. My heart was racing but I felt it best to keep completely silent. Soon it became clear that he was leading me to the place where my sexual journey had begun: his room.
We entered and the door clicked shut behind me. In seconds I was on my knees, begging in desperation for his mighty cock. "Please feed me Sir, please" I remember saying. Carl was having none of it though.
"Christ, you really do have a bad case of cumlust. We're going to have to totally shut that down" he said. "Jay went completely off-reservation face-fucking you this morning. He knows as well as anyone that when training a pussyboicunt, blow jobs and the taste of cum are the kind of confusion that a boy just doesn't need. That's his fault though and he's going to have to take his fair share of the punishment for it... Not that you're blameless in this sorry affair either. If you weren't such a cock hungry little slut I bet none of this would have happened. You knew that taking Jay's cock in your mouth was against the rules and yet you still let it happen. We've got a lot to talk about in the next couple of days boy...
Meanwhile, we need to get you back on track. You're going to be with me for a while." Much as I was disappointed by not getting to suck Carl (cum confusion... seriously?) and I was seriously baffled that somehow I was to blame for Jay sticking his cock in my face (really?) I felt overjoyed to be back with him. He looked so hot. Tonight he was just in regular jeans and a tight white t-shirt with the school's FHS initials embroidered on one side. I could just see his chest hair sticking out of his collar, joining up with his heavy stubble. If I wasn't still on my knees I would be weak at the knees.
"Your problem is that you're still in training, you're still being formed and shaped. You don't need Jay distracting you... Sure you may suck some cocks in the future - when you leave here - but not today and not this month. Cock sucking is a potential by-product of the program, not your aim.
No, being a jizz eater is not your purpose in life. That's why you're with me. It's important that we get you back on track... I'm here to take you past the real point of no return.
And I've got to confess Bobby, my feelings for you have been growing since we first met. In fact, I've become rather cunt-struck..."
Swoon. What else can I say?! I'm here, with Carl, in his room and about to go to bed with him. My heart wants to burst (ouch, burst! fucking stretcher plug is still inside of me though, maybe it will come out tomorrow?). Anyway, time for bed. Yay!
Next: Bobby takes his first fist...
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