Day 8. My first ffuck
Themes include fisting, leather, bondage, poppers and domination. Average reading time: 20 minutes.
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Christ, what have I become? Today was by far the most intense experience of my life... Now I know exactly what Carl meant when he said he'd take me past the point of no return. After all, how can I possibly go back after what's just happened?
The day started calmly enough. We had slept together and I've got to confess that it bought back all of my feelings from my first night. Yes, I wasn't locked in a chastity device back then and yes, my hole wasn't being held painfully open by a butt plug and yes, I'd only just lost my anal virginity to Carl BUT apart from all that... I was lying next to the man who had introduced me to the pleasures of gay sex and a big part of me wanted more. However, an even bigger part wanted to be looked after, and being Carl's spoon felt amazing.
A couple of times in the night I could feel his big schlong firm up and prod my arse. I spent the night hoping that the feeling of my butt cheeks nuzzled in his direction would tip him over the edge, but unfortunately Carl was way too controlled to take advantage of any midnight lust. He didn't even fuck me with his morning wood. I know that I was plugged, but a boy can dream, right?
Come daybreak I was woken by him gently shaking my shoulders. It took me a moment to work out where I was, but looking into the deep, languid pools of his eyes was a wonderful first sight. "Morning Bobby" he smiled, "time to get up. Going to be a fun day - for both of us!" With that he stood up from the side of the bed and I saw that he was dressed already. That didn't matter - even though he was covered up I couldn't get enough of his body. In fact, his choice of a loose black t-shirt and a pair of black shorts with red detailing made him look all the more alluring. Just the suggestion of what was there was enough: the outlines of his muscles and the prominent bulge of his dick shifting before my eyes. I could feel my cock fighting the constraints of my metal cage as I lapped it all up.
Carl threw me some similar clothes and told me to get dressed. For once it was nice not to be in a jock or an aggressively tight pair of shorts. This, combined with the light streaming through the windows and Carl's comfortable demeanour made me feel optimistic. Whatever was going to happen today I felt as if I could handle it... Sure, the program was progressing but I was with Carl. What was the worse that could happen?
We sat down at a small table to eat a light breakfast. It was the first time I had actually had a chance to talk to him and like an anxious young pup I tried to make conversation, saying how much I liked his room and how good it had been to spend the night with him.
The words were barely out of my mouth before he turned it around and asked whether I enjoying my time at the School. I could feel my face colouring as I answered. I didn't want to piss him off, but it felt like this was my opportunity to be honest. I told him that I'd actually been pretty shocked by what had happened to me so far. That I had been held against my will by a bunch of sexual terrorists and that what they were doing to me broke all laws of nature and decency. That I was being forced into becoming-- before I could finish he cut me off.
"That's not how I see it Bobby... I've seen the tapes, I've looked over your CiS files. It's pretty clear to me that you were the one fucking yourself on those toys yesterday. No one forced you to ride the bench. And no one forced you to suck Jay's cock."
I tried to rebut him. "Well, yes... but I didn't--"
"Didn't what Bobby? Didn't sign up to lose your virginity of your own free will? I don't remember anyone making you do that?"
"But, that's not the same--"
"And you took that fuck train like a complete pro! Trust me Bobby, you've been blessed with a lot more talent and ability than you realise. All the School is doing is building on top of what you've already got. We're just digging deep and uncovering what's buried inside of you... Hell, nobody could take that much cock in one train if they didn't really want it!"
He was saying this all so smoothly, but surely he knew this was all a lie. I could feel my anger welling up. "I wanted to lose my cherry Carl, not be turned into a fucking... pussyboicunt!" I shouted. It was the first time I had said the word out loud and it shocked me.
"Calm down Bobby" he replied. "You know what your trouble is? You haven't accepted who you really are. Don't give me that bullshit about only wanting to lose your cherry - guys like you think about sex non-stop. Are you seriously going to tell me that you didn't enjoy being fucked by me? Or by Jay? Or that the 30 guys in your fuck train didn't satisfy you? I know I satisfied you in the gym when I double dicked you. Christ, even last night I bet you spent all your time thinking about my cock ploughing your pussy...? Yeah, that's right, I could feel you massaging my dick in your sleep, trying to seduce me. You want what's happening to you, you want it big time, you're just not prepared to admit it."
I sat there speechless, trying to process his words. I couldn't believe it, but just enough of what he said rang true that it hit home.
"Push back all you want Bobby, but by the end of today I think you're going to feel very differently. You're going to have to let yourself go though... you're going to have to let the true Bobby out. Can you do that for me Bobby?" He reached out and took one of my hands in his. I felt dumbfounded but the sudden warmth of his touch comforted me and I couldn't help but nod.
"There's a good lad Bobby, I know you don't want to disappoint me."
He let those words hang in the air before releasing me and saying it was time to get ready. Okay, Bobby, positive thoughts... Unsurprisingly he directed me to the bathroom and told me to use the enema hose and then have a shower. The automatic flushing program did its work and soon I was back in his room, naked except for my cock cage and the plug harness.
However, the room was different. The blinds had been closed and it was much darker. Carl was different too... Fucking hell, once again I could feel my cock fighting against the metal of my cage. I didn't think it was possible for Carl to get any hotter but he looked a fucking dream. He was wearing skin-tight leather chaps that perfectly framed his magnificent dick and low-hanging balls. The chaps had a single red stripe running up and down each side, and red piping around his crotch too. His upper body was naked except for a thick leather harness that drew attention to his firm and muscular hairy chest. He stood in front of me, confident and poised, an inch or so taller from his heavy engineering boots. I had never looked at anyone before who so embodied a sexual ideal... I wanted him. Despite all my fears, wherever he went I would follow.
He flipped a wall switch and a screen unfurled to reveal a secret space. Truly, it can only be described as a fully fledged sex dungeon. The floors and walls were dark and the room was lit with a red light. It cast dark shadows over the intimidating sex furniture and the racks of toys lining the walls. It all felt eerily familiar from Trent's classroom, except for one thing: the leather contraption hanging from the ceiling. I knew enough from the constant porn I had been forced to watch that it was a sling, designed to let a bottom be fucked easily.
In total delight I immediately asked whether Carl was going to fuck me.
"Bobby, I'm not going to fuck you, I'm going to fist you" he replied.
Fist me?! My mind went into total meltdown. Whatever I had been expecting, whatever I had been ready to do with Carl just moments ago went straight out of my mind. I may have been a relatively naive sexual virgin until a few days ago, but I knew enough to know what fisting was. There was no way I was going to let someone stretch my hole enough to take a fist!
"Please, Sir! You have got to be joking" I said with all seriousness. "Is that what you mean by accepting who I am, to let myself go? To be fucking fisted?!" I was getting more angry and frustrated. "This is becoming a sick joke that has got to stop! First you rape me, then you gang fuck me, then you stretch my hole--." Finally the fucking penny dropped. I stood in front of Carl, dumbstruck. Yes, this is what the program has been leading up too. This is what they meant by being a pussyboicunt. A fisted, used and abused pussyboicunt.
Carl stood in front of me shaking his head. "Dear god, the youth of today... You guys need way better sex education. Black and red Bobby!--" motioning to the stripe running up and down his chaps "--that means handballing. All the clues have been right in front of you for days."
Carl's dismay at me not `picking up' the clues didn't help. I wilted in front of him. "Please don't fist me Sir, please don't do this to me, I'm barely past being a virgin, I'm not ready for this..." I pleaded.
"Oh, you're ready all right. I don't think I've ever seen anyone so ready for this. The size of plug holding your ass open? My hands are going to be able to slide in like you were born to it...
Now, you may not think that you're going to be able to take my fists--" with this he stretched his sizeable hands in front of me "--but I know you can. Look at all the things you've taken up your pussy so far. When you arrived I bet you thought you wouldn't be able to handle any of them. Well you have. You have a hell of a lot more talent and ability than you realise, Bobby. You just need to believe in yourself... Besides, I thought you liked me... that you enjoyed being fucked by me? Surely you want to do this with me?"
"It's not that I don't like you Carl... it's just that I don't want to be fisted. I thought that being selected for this fucking `program' was about a state of mind - about being some kid of slut - not that you were physically going to turn me into a cunt. I don't want my hole to be fucking ruined!"
"It's too late for that Bobby... Anyway, who says your hole is going to be ruined? If anything, everything we've done so far has made it better. There aren't that many guys your age out there with a hole as capable as yours.
Besides, you're right... we are making physical changes to your body, but being a pussyboicunt is a mental state of mind too. You just need to embrace it... as soon as you do I know you're going to love this. Now, if you've stopped whining shall we begin?"
I had no choice. Carl was stronger and bigger than me in every sense of the word. He came over to where I was standing and gently lifted his right hand up, cupping one side of my face. He looked straight into my eyes. I could smell his body and the tight leather warming up in the heat. "Don't worry kid, I know you're going to be a natural at this. You'll be riding yourself on my fists before you know it. Now, get into the sling."
Despite his gentle caress, his instruction to get into the sling felt like an order. He released his hand and nudged me into the sex dungeon. I tentatively walked over to the sling, unsure as to how I should climb in. Somehow the porn videos never showed this part and my mind was doing too many revolutions to think clearly. Carl quickly explained how, and in moments I was lying back on the thick leather, my legs wide open and pointing upwards, my hands by my sides.
Carl stood in front me. "Now, I want this experience to be as good for you as it is for me. I want you to totally embrace what's happening, to give yourself up to my fists. I want you totally focused on one thing and one thing only: being the best cunt you can possibly be. To help you make that choice, I'm going to make it easier by taking away the choice..."
As he spoke I realised he was securing leather buckles around my ankles. They were no longer just supported, but locked in place. I tried to struggle to escape. "See, that's what I'm talking about. If you struggle, the tougher this is going to be... especially with my fist in your ass!" he laughed.
In no short order my hands had also been secured, but now up in the air above and behind my head. The final touch were two thick leather straps that went diagonally across my chest, from shoulder down to my lower stomach. I was literally locked to the sling, my ass defenceless and sitting proud. There would be nothing I could do to escape Carl's fists. I was his for as long as he wanted.
"Now... onto the final touches..." he said as he held up a thin piece of transparent tube. It looked like a heavy duty version of one of those nostril things that old people wear in hospitals to help them get oxygen. Surely not though? "This, this... will make everything easier for you" he said. WTF? He was going to drug me?!
Carl evidently saw fear and panic in my eyes. "Don't worry Bobby, it's just a poppers delivery device of my own creation." I was confused. Poppers? Carl soon explained that they would help dilate my blood vessels and my ass muscles. They'd also make me light headed - all things that would help in his goal.
"I'm surprised you haven't been introduced to them in your anal stretching sessions, but Trent has never believed in being conventional. Probably a good thing to be honest - if you can take the hole reamers he's been using on you without poppers, then my hands are going to be a synch!"
Somehow this didn't reassure me, nor did having the tube wrapped around my face and inserted into my nostrils. All of a sudden I could feel a stream of fresh air going straight into my airways. I tentatively sniffed, though I couldn't discern any flavour, scent or effect.
"Not so fast pig, you're only going to get a dose when I want you to" said Carl. He lifted up some kind of foot pedal that had been lying on the floor. "See? I just press this down and you'll get a nice big hit". He grinned and put the device back down. He was clearly enjoying this.
He walked me through the final touches... bringing over a large open canister of lube to the business end of the sling. Positioned at just the right height for him to dunk his hands in as much as he needs. And then a full length mirror, angled on a stand so I could see both my entire body, tightly secured to the sling, and Carl in leather standing in front of my ass. I've got to say, it was a hot sight.
"Right, time to get started..." he said. Determined to put me at my ease, he ran his large hands across my body, stroking me gently. I felt myself calming down, before Carl said he was going to remove my plug. And the cock cage. He unlocked the straps and threw the leather harness to one side. It felt so good for my cock to be free, even though it wasn't exactly standing proud at the moment. Running scared more like.
Carl then grabbed the plug in my ass and started to pull it out of my hole. He teased me though, pushing the wider part of the plug in and out. I could feel it raking my prostate and temporarily lost myself in the feeling of the stretch - after so long wearing the plug it felt good to have movement down there.
"Jesus Bobby, you're juicing up already!" Carl exclaimed. He pointed down at my dick, which had started leaking a thick stream of crystal clear pre. Damn!
"See how much you like this? Your dickslop means one and one thing only. Your body wants this, you want this and your hole needs it."
I was scared but I couldn't deny it. However, I didn't want to admit it - I didn't want to give Carl the satisfaction of being right.
After massaging my hole with the plug for a few more moments he finally withdrew it, pulling it all the way out and holding it in front of me. Jesus fuck! After all this time I finally got to see just how big the plug was that Trent had locked me up with yesterday. The thing was fucking mammoth and I could feel my hole spasming as it adjusted to its new found freedom.
"Don't get too comfortable boy, my fists are going to be filling that space before you know it" said Carl.
Oh fuck... seconds later Carl was on his knees and rimming my hole. This was only the second time I'd ever experienced a rim job, but this time was even more electrifying. The gang fuck and the near continuous toy sessions seem to have given Carl more to work with, and it set my hole on fire with lust. I could feel his tongue sucking and licking and burying itself deep inside me, way deeper than I possibly could have imagined. My entire body groaned with pleasure. I accidentally caught a glimpse of myself in the mirror, which forced me to take a second, longer look. Carl was kneeling in his black and red leathers, his hands separating my ass cheeks apart, his face buried in my pussy. It was unbelievable.
"That's a sweet hole kid, way better than when we first met. The only thing that can make it better is for it to be bigger..." He embedded his face in my ass again, his stubble super sensitive against my tender flesh. I never imagined anything could feel like this.
He rose to his feet, a satisfied but eager look on his face. Like someone who knows the appetiser is good but the main course is going to be the real deal. His face was flushed and his cheeks were wet - wow, he really did go deep! He wiped his face off with one hand before transferring the surplus fluids to my pussy opening. That, and his extensive rimming, had made me dripping wet and receptive. Straight away I could feel his fingers probing my ass and it was immediately clear that I was slack enough that he could get a couple of fingers in without even trying. Damn!
He held my eyes with his and, without looking, took his hand away from my hole and plunged it into the lube bucket. It came out covered in a white, thick, gelatinous liquid that clung to his fist. As if drawn by a force more powerful than either of us, his hand was back on my ass and I could feel the coolness of the slippery liquid against my hole.
"Man that's a sweet hole Bobby... Its way too tight though, but we're soon going to change that together..." as Carl said these fateful words I could feel him slowly pushing more and more of his fingers inside of me. I could literally feel the slimy lube beginning to line my ass, preparing me for the moment his entire hand would force its way in.
Whatever my trepidation against being fisted I couldn't deny that the feelings in my ass were pretty spectacular. The fucking and the toys had made me so ready for this moment. It also felt amazing to have something real in my hole again, not the inhuman, firm rubber of an imitation cock, but a genuine, warm, flexible human hand. After yesterday's session - where I had had to bench fuck myself on the toys - I was loving that someone was once again taking control of my ass. Here I was, securely bound... there was no way I could escape what was happening to me. Despite my fear of fisting it all felt right.
Carl constantly reinforced the feelings emanating from my pussy by guiding my thoughts. I can remember him telling me that he was slowly and gently opening me up... that (of course) in the future I'd be able to take a fist without the hassle of all this warming up, that it would just slide in as if my hole was made for it... I couldn't deny it, right now I did feel as if I was born to it. The stretch felt so good, so right, that it felt like the most natural thing in the world. I wanted this, I wanted more. I had never felt so connected to any one moment - to any one person - in my entire life. This was it, this was my future.
Carl must have seen the change in my body as I gave up all my apprehensions. I heard a hiss and suddenly my nostrils were filled with the smell of chemicals. This must have been a hit of the poppers and woah - my entire body felt flushed and my head started to float away! The sensation in my head matched the sensations in my hole: suddenly it felt more relaxed, more open, more receptive.
Carl took total command and started rotating and pushing his fingers more firmly against my ass. Never relenting or retreating. It was an amazing sensation... I knew that I was being stretched bigger and wider than ever before. I couldn't help myself. "Please fist me! Please Sir, I need it! Make me your cunt! I'm all yours!" I cried.
"You're damn right you are, bitch!" I heard Carl say and I smelt another big hit of the poppers. My head near exploded as his hand started to push even further inside of me.
"This is it kid, this is the last moment that you're truly going to be a virgin. I'm about to take your fist cherry and you're never getting it back..."
With that he forced his hand that tiny bit further and my asshole finally gave way. Carl's fist was fucking inside of me! My hole felt fuller and bigger than it ever been in it's entire life. I couldn't help myself. "Motherfucker! Take it out, it's too big! I can't take it! You're fucking ruining my hole!" I shouted.
"That's not a hole anymore kid, it's a cunt! And it's only going to get bigger from here on! Eventually your pussy will relent and give up the fight... then you'll feel the pleasure. Just hang in there kiddo."
And so it did. Whatever his determination to open me up it was clear he was a pro. Just like the first night... He slowly let me adjust to the powerhouse of feelings emanating from my new-found cunt. He was constantly firm and yet gentle at the same time. I slowly went from the shock of feeling his fists inside of me to being unable to imagine how I had lived this long without being fisted.
It was all down to Carl. He had taken both my cherries... surely that had to mean something? Here he was standing in front of me looking stunning in leather... taking the time, care and attention to lovingly open me up. This was the most intense moment of my life and I had Carl to thank for it. Damn, I think I've started falling for him...
I kept glancing across to the mirror. It was amazing to see my ass with Carl's hairy forearm disappearing into it, but actually it was even hotter to see that his dick was rock hard the entire time he was fisting me. I could see a thick stream of precum leaking from the fat helmet and pooling on to the floor. I was doing that to Carl! Me! I was the one responsible for turning him on and making his prick hard. It felt so good and the thought made me want even more...
I lost all track of time and space as his fists continually ravaged my hole. By now Carl had moved on to using both his hands, swapping from one to the other to continually stretch me out. Just when I got I used to the motion of his fists, he would change the direction or angle of attack to remind me that I was his. It was relentless. The only pauses were the occasional dunking of his hands in the seemingly inexhaustible container of lube by his side.
Carl felt like a machine, ready to go on forever. However, by this time I was actually beginning to feel pretty worn out. No matter how much I wanted to be used by his fists non-stop, my hole, body and mind were beginning to tire. It didn't matter how many hits of poppers Carl fed me, or how loose my hole was beginning to feel, I wanted it to stop. It was all simply too much.
Christ, even writing those words now makes me feel guilty. This had been so amazing that I didn't want to let Carl down. I didn't want him to have to stop before he was ready, but I just don't think I could continue... Maybe Carl felt it too as he relaxed the pace for a bit. I tentatively broached the subject, that it had been amazing - more than I ever could have imagined - but that...
"What is it boy? Say it" said Carl.
"My hole can't take much more Sir" I replied. I could see his eyebrows arch in dismay. "Sorry Sir, my cunt can't take much more Sir. I'm totally exhausted. It's been amazing - just like you said - but I don't think I can carry on..."
He looked me in the eyes. All the while we'd been talking his right fist had slowly been sliding in and out of my ass. Even though I was knackered I could feel just how loose and slack my hole had become.
"Very well cunt. Just another 20 minutes and we'll stop... I'm not going to quit the pace though. I want you to remember your first fist forever!"
And with that his actions became even more brutal, his commands even more explicit. "Tell me you want it, tell me you want to be turned into a cunt" Carl would cry. If I didn't answer he would ram his fists into my hole hard. I had no choice but to cry out that I wanted to be stretched, used and turned into his cunt. It was excruciating. If not answering his demands he was making me grunt with the power of his fist thrusts. I honestly couldn't go on much longer.
Thankfully I could feel Carl building up to the finish. His left hand was riding my cunt with renewed vigour, his right hand now furiously jerking his giant dick. It didn't take long before he cock exploded and I felt one last final deep and painful thrust of his fists as his dick shot thick ropes of cum across my chest.
Man alive, I was spent. Truly exhausted. My feelings were difficult to describe. The intensity was unbelievable and yet the last hour or so had been pretty tough. I had kept going to keep Carl happy and only now was it hitting home how tender my hole was. I suddenly realised that one of his hands was still inside of me and now I was aware of its presence it felt huge and painful.
Before I could say anything Carl saw me wince and struggle against the restraints of the sling. I was no longer horny and I wanted to be released. Needed to be released.
Carl told me to calm down and then said that I had done well for a first time, and that he hoped I wasn't too gentle for me. Fuck! That was gentle?! He told me to take a deep breathe in, and then exhale. On the out breathe he withdrew his fist from my ass in one smooth motion. For the first time in hours I was empty. Not that my hole could tell. I knew that the stretching and the toys and Carl's fists had fundamentally changed it forever.
Carl stood back and it honestly looked like he was admiring his handiwork. I was right, because in seconds he was rubbing his finger tips against the entrance to my hole. "Wow man, that's a nice set of pussy lips you've developed there. Looks like we did some good work today!" he said.
I didn't really appreciate what he meant. Pussy lips? At this point I was just desperate to be released and to move my legs and arms around again. I was suddenly very conscious of my body and wanted to be out.
"Hold on kid, let me go get cleaned up and get the lube off my hands. Then I can get you down."
I didn't have a choice. He left me and I soon heard the sound of running water. And then the sound of a shower. Fuck! I was in agony and desperate to be free. I wriggled my body as much as possible to distract myself but Carl seemed to be in no rush.
Eventually - finally! - he came back in, looking relaxed and wearing his shorts and t-shirt from the morning. He started to unbuckle my legs and then suddenly his mood changed completely as he looked at my cunt. He seemed disgusted at what he saw. "This simply won't fucking do kid. When I left your cuntlips were nice and puffy, surrounding a nice big gape. Now though? They're closing up! I'm fucking disappointed in you."
What the fuck? I had no idea what he meant. How was the state of my hole my fault?! He was the one who had been working on it for the day.
He evidently saw the complete confusion in my face as he repositioned the mirror to give me my first direct view of my cunt.
I was fucking shocked. I screamed in horror that my ass was ruined for life. It was a dripping, sagging, distended mess. I could see the flesh of my inner ass, red and undulating, surrounded by puffy lips that pulsated as my hole unknowingly and desperately tried to close. And he was disappointed in my progress???
"What the fuck have you done to me? I'm fucking ruined!" I cried.
"You're not ruined kid, I'll be the judge of that. But your hole should be way bigger than this by now. I'll give you a little leeway as I only took your fist cherry today but that's no excuse for the poor state of your pussy lips. I can see that it's time we stepped things up a gear. Looks like I took over your training just in time. I can tell it's been way too soft. Tomorrow your program starts for real..."
I think I must have fainted at that point because I have no memory of how I ended up in bed. I woke up to early evening darkness. I was famished and ate hungrily from the food laid out for me. There was no sign of Carl, but he had left a note. Told me I should eat as I would need my strength for tomorrow, and that I had been locked up again (cock and hole). Damn. I could feel that the plug was even bigger.
So here I am writing this. I can't believe what has happened. All the TVs are now showing hardcore fisting porn and the channel can't be changed. I think of the memory of my poor hole and I don't know whether to feel sick or be repulsed. What the fuck has happened to my life?
Next: Bobby gets machine fucked...
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