A Jock in the Machine Ch. 01

'Hey, what the fuck, let me go, you bitch!'

'That's not a very nice thing to say now. And wasn't it you melting in my hands not even five minutes ago.' Cassie unbuttoned her jeans. 'Can you imagine our disappointment when it came time to step up and Eric just didn't deliver on his promises?' She shifted herself to get her legs out. 'He was nowhere near as big as you!' Cassie tossed her jeans at Sam's face. He could no longer see her. 'Or me.'

Thud!

Sam felt a large object crash down on top of his cock. The sheer weight of if it made it feel as if someone had punched him.

'Bitch, what the fuck is that! I can't see! Get these, ughh, jeans off me!' He shouted shaking violently. Finally, a small creak came from the bed. The cuffs dug further into his skin, making him groan in pain.

'Again with the bitch. I told you that wasn't nice!' Cassie laughed. 'Tell you what, why don't we play a game?'

'I ain't playing any games, bit-' he felt the large object get lift off from him before it came crashing down again. This time it hurt even more and it felt even heavier.

'Rule number one. You can't say bitch anymore, or you get punished.'

Sam didn't reply. He panted hard and heavy, groaning in discomfort and lingering pain.

'You accept then? Good' Cassie said as she moved in closer. 'The game is simple: you guess what I have on top of you, and I remove the jeans.' She moved in even closer.

'What the hell kind of game is that! Get these damn jeans off me!' Sam struggled to no avail.

'Guess.'

'I'm not- Aargh! Fuck!' he cried out in pain as the cuffs on his hands started digging into the bones of his wrists.

'Guess.' cam Cassie's cold, commanding voice.

He couldn't move. He was bound in place. His wrists hurt. No matter how much he tried to escape, he had no choice. 'Ugh, is that, uhh...' It felt long, whatever it was. And thick. And burning hot. 'Is that your arm? Or your leg?'

'Very good try! You're so close. Let me give you a hint...' Cassie exclaimed as she moved ever closer.

Sam felt whatever it was moving further up over his body until suddenly, something warm and soft pressed between his legs. 'The fuck is that! Is that a fucking strap-on?!'

'Oh, Sammy boy, so close once again! But do you really think a strap-on can do this?' Cassie flexed, tensing up her entire body.

Oh, god, what did she do? It was growing! He could feel it! He felt it sliding further up on top of his body. Are those veins? Did it just... throb? 'No way...'

'What was that?' Cassie teased him as she flexed once again.

No way. It's far too big! 'Is that... Is that your...'

'Is that my fat fucking cock?' Cassie took the jeans off his face. 'Ding! Ding! Ding!' she yelled, accentuating each ding with a throb. 'We have a winner!'

Sam didn't want to look. He really didn't want to look. But he couldn't look anywhere else.

It was huge. Massive. Bigger than massive. She was sitting between his legs, but her cockhead was nearly up to his chest. It looked bright purple, swollen bigger than his fist and gushing more precum than his entire load.

'Can't take your eyes off it, right? I get that a lot' Cassie leant forward, grabbing her cock with both her hands. She couldn't fully encircle it even with both of them. 'It likes you a lot, too! In fact, it can't wait to get better acquainted! All twenty-two inches of it!'

Sam's eyes widened further than they'd ever widened before. Surely he'd misheard. Twenty-. No way. That's not possible. But looking down at it, it was definitely there, defying all reason and logic. And she wants to-.

'What the hell! You crazy bitch! Get that thing awa-' Sam suddenly felt something clog his mouth. He couldn't get it out, and when he tried speaking only muffled groans came out. He looked down in fear, but much to his relief it wasn't what he feared it was. Cassie had put a ballgag on him.

'Bad pet.' Cassie pouted as she finished tightening the gag. Pet? He wasn't a- 'You broke the rule of the game again. Every time you break a rule, you have to be punished.' She heaved her colossal cock off of him before crashing down on him again with full force. This time it hurt even more. Her fully hardened beast felt as if someone had dropped a bag of rocks on top of him. He screamed into the gag, but only a few barely audible sounds came through.

'Now, since you won round one, it's time to move to round two. Aren't you excited, pet?' Cassie laughed as she slid down the bed, going further and further until her entire cock was no longer on top of him. Instead, it was now between his legs, her menacingly large cockhead dangerously close to his ass. The entire time she did this, Sam continued shouting pointlessly into the gag, shaking violently as the cuffs dug hard into his body. 'The rule for round two is simple, pet. You can't cum before I do.'

Don't cum? That was the easiest thing ever in his situation. There was no way he'd ever even get hard let alone-. Wait? Before she did? Did that mean...

Sam's trail of thought was interrupted by a wet, sloppy sound. He peeked downwards, completely aware what the sound was but terrified of it nonetheless. Between his legs, Cassie was jerking her colossal, throbbing cock with both hands, every now and then reaching over to her spewing head to grab a large dollop of precum. 'She's lubing it! Oh no. No no no no!' Sam's thoughts raced as he became fully aware of the inevitable. He had nowhere to run, no way to stop her, and worst of all, she had finished lubing her cock up.

Once Cassie was satisfied with how well coated her cock was, she reached over behind Sam's head to take one of the pillows. As she did, her nipples brushed past his forehead, and for a blissful moment he forgot all his ills and focused on the magnificent rack on his face. The moment didn't last however.

'Lift up your ass.' she commanded him. He refused. He was no pet and wouldn't play her sick games. 'Lift up your ass, or I smack you again.' Oh fuck, he was still feeling the last time she smacked him with that thing. He did not want to feel it again.

Defeated, bound and about to get fucked, Sam twisted and shifted until he was finally able to lift his ass off the bed for a slight second. It was all it took, as Cassie deftly moved the pillow under him, leaving his ass raised off the bed. The perfect position for her to fuck it. Giving one last tug to make sure she was still well lubed up, Cassie moved between his legs, her python snaking its way up until her fat, glistening cockhead planted its sloppy kiss on Sam's rosebud. Sam's eyes widened, as if about to pop from their sockets. There was no way something that big would fit inside him. It was thicker than his forearm! And he had the biggest forearm in school!

Without giving him any further warning, Cassie pushed forward. Sam tried to resist, to clench his muscles but it was futile. The pressure from her massive cockhead was too much, far too much...

With a loud pop, she was in. her entire head in one motion. Sam screamed as much as he could into his gag, he thrashed and turned, trying desperately to free himself and run away from his torturer. The pain of the cuffs digging into his limbs was nothing compared to the pain of his ass being ripped open. Tears fell rapidly down the side of his face. And yet barely any sound came from him. The bed barely creaked. No one would hear him. No one would help.

On the other end of the cock, Cassie was pleasantly surprised at how easily she'd entered him. When her fingers had gone in without any resistance earlier she'd began to suspect that Sam's butt wasn't as pure as she'd thought, and now, with her getting in it in less than a minute she was certain of it. She'd have to keep it in mind for later. But back to the matter at hand, now that the hardest, or easiest in the case of Sam's greedy ass, part was over, it was time to really get to work. Cassie repositioned herself, standing on her knees as she gripped his hips for leverage and began pushing herself deeper. And sure enough, she was making progress. Inch after inch after inch slowly entered the jock's ass.

Sam was in hell. If he'd thought her entrance had been rough, her actually moving blew it out of the water. Lube or no lube, he was being fed a mammoth of a cock at such a slow, agonizing pace that he could feel every single one of her criss-crossing veins as she burrowed in him. He felt so full, and yet it just kept coming. And coming. And coming. And... he was hard. He looked down, completely stunned. And sure enough, despite the immense pain and hopelessness of his situation, he saw his own cock standing completely erect.

Cassie had barely managed to fit a quarter of her cock inside Sam when she felt him tightening around her. Looking down, she saw his painfully hardened member pulsing and throbbing. It looked so small by comparison.

'Bet you didn't expect that, huh?' she turned to face him, a stern, focused look in her eyes. 'I just hit your prostate. Felt good, didn't it? Does it also feel good when I do this?' She flexed her cock inside of him, briefly getting it even thicker, pushing back against the clasping walls of his ass.

Sam nearly fainted. His cock throbbed, leaked and spasmed. What she'd just done hurt more than anything before. She stretched him even more than he'd thought she would and despite all that he nearly came from it.

'Good pet. You liked that, didn't you?' she teased as she took a firmer grip on his hips. 'Then I bet you'll love this!'

Cassie lunged forward. Hard. Her cock sank in fast and deep, earning a muffled moan from Sam. Or maybe it was a yell? She didn't care. All she cared about was sheathing her entire cockmeat inside him, and after that last thrust, she'd managed to get just over half of it in. But that wasn't the best part.

Sam's entire world broke. He saw her bracing. He knew what she was about to do. But nothing could have prepared him for this. In one savage push, a huge part of her dick speared him. He couldn't move. His arms and legs felt like jelly. He couldn't scream. He could swear he could feel a bulge in his stomach. His eyes almost rolled to the back of his head. And just like that, he came.

Sam's ass clamped shut on Cassie's cock as he shot his load. It was even more forceful than the first one. The way he was positioned meant this time he had no chance of steering it clear of his face, and the first shot landed square on his right cheek. The second landed further down, coating the gag and his lips. The rest landed all over his chest until finally the last few drizzled out of him. And then, he was just as painfully hard as before.

Cassie laughed, enjoying the feeling of his clenching ass on her. 'Bad pet. I told you, the rule is to not cum before I do! Now I have to punish you.' she giggled as she began to pull out. The friction on the way out was almost worse than on the way in, but at least after a while Sam no longer felt like his prostate was getting jackhammered. Cassie withdrew almost all of herself, leaving only her bulbous head inside. She repositioned herself, planting her hands to the sides of his waist and getting up on her toes, her butt in the air. She raised her head to see Sam's reaction. 'Here comes your punishment, pet!'

The bed creaked, almost sounding like it would give way. Sam screamed his soul out into the ballgag. His cuffs rattled as he shook with them. But all the sounds were drowned out by the loud wet smack that resonated in the room as Cassie hilted herself in Sam in one monstrous push. Going from zero to a hundred in mere moments, she'd shoved her entire length and girth inside him until her fat, churning balls smacked his ass with such force that they left small bruises on it. There was no rational thought left in Sam's head. No thought of any kind really. She'd rearranged his guts to accommodate her massive beast. She may have even broken something in him. He wasn't sure. He swore he could feel her in his stomach, or maybe his throat, or his mouth, he wasn't sure of that either. What he was sure of was that he had cum in his left eye and that it was his own.

'You know what the punishment is and you broke the rule again!' Cassie shook her head at him. 'I don't think I can keep you as a pet anymore. You're far too bad.'

Her words brought Sam out of his orgasm crazed trance into a brief moment of lucidity. Did she mean she was going to let him go? Would he even be able to leave? How was-

'But I can keep you as a good slut!' she laughed as she watched the color drain from his face in utter defeat and terror. 'Now then, you need to be punished, slut!' Cassie withdrew all the way to her tip.

Oh no...

Again, she hilted herself, this time even harder and faster than before. His body was losing all form of resistance against her as with every thrust she molded him into her perfect cocksleeve.

He came again, less than before. His balls were starting to hurt. The force of her nuts slamming against his cheeks felt like it burning. And just like that, the exit motion began, much easier than before.

Another impaling, another wet smack of grapefruit sized balls on muscular ass cheeks, another dwindling cumshot.

And another.

And another.

Her rhythm never changed. Slow. Hard. Powerful. She left just enough time for him to finish one orgasm before giving him the next. Two more full thrusts. After the first, he barely dripped as his balls drained the last of their juice. After the second, they tightened painfully hard, but no cum came out.

'You didn't break the rule, slut!' Cassie exclaimed, almost sounding proud. 'Let's just make sure you didn't get lucky with this one.' She pulled back in the all-too-familiar motion, before rushing back in, gutpunching him from the inside. There was no resistance on her withdrawal, nor on her push. She could see him orgasming under her, but his spent but still painfully erect cock didn't leak a single drop. 'Perfect. It seems like you've learned your lesson, slut. Should we move on to round three?'

He didn't have choice really. Even if he wanted to say no, he was gagged. He felt her pull all the way back, just like she'd done so many times. He braced himself, even though he knew it was pointless. It was coming, and it was going to hurt. He closed his eyes and then... Nothing.

Cassie loved his futile attempts to prepare for her. But she had other ways to punish him, and they needed to be done. As much as she just wanted to jackhammer him immediately and completely break him physically, she was nowhere near done breaking him mentally. With that in mind, she pulled completely free from his ass. A loud pop rang around the room, prompting Sam to open his eyes.

He couldn't believe it! She was finally out of him! He felt so relieved. The worst was over. Sure his balls felt like they'd shrunk in on themselves, and his buttcheeks burned hotter than the sun, and his ass felt... empty. It felt like something was taken from it that it was desperately trying to get back. He looked down to see her, and her grotesque member. It was unreal. It hadn't softened at all, and if anything it looked even harder. And her balls looked even fuller. She got off the bed and started walking around it, coming near to where his face was. With each step, every part of her jiggled and glistened. Her enormous tits, her amazing ass, and her behemoth of a cock. He didn't know what she had planned next, but it would not be good. She reached around towards his head. He closed his eyes expecting the worst, not even knowing what the worst could be. And then...

The ballgag came off. He wanted to scream, to curse her, to say anything, but his throat and mouth had completely dried up and not a sound came out. All he could do was stare in horror as she got up on the bed, one silky smooth leg at a time and straddled his head. Her far sweaty balls came to rest on his forehead. And his eyes. And his nose. They were so big and full they covered half his face.

'Round three is simple, slut.' He heard her say above him. 'I'm going to feed you my cock, and I won't stop until your chin touches my skin. If you want to breathe, all you have to do is put some teeth on it.' She raised herself up and bent over, aiming her turgid cock at his mouth. 'Open'

He didn't want to do this. But if he didn't he knew she'd punish him. And he was afraid of that more. So reluctantly, he opened his dried up mouth.

'Wider.'

He opened up a bit more.

'I said wider, slut!'

He had no choice. It was going to happen. He opened as far as he could. This is what had happened to Eric, he thought, and hoped and feared that it would not be as bad for him. And just as he was deepest in his thoughts, trying to escape into his own world, he felt his mouth get stuffed to its limits. Her giant spongy cockhead entered his mouth, coating the inside in sticky precum. There was still so much dripping from it. It landed on his tongue and for the first time he tasted it. And it tasted sweet. Almost unnaturally so. Losing control of his body, he swirled his tongue around in what little of his mouth wasn't overfilled with cock for more of her sweet juice.

'Slut likes my cockhead, does he?' He heard a giggle from somewhere that he could not see. It didn't sound menacing anymore. Or maybe he just couldn't hear it. 'Then let's see if you like it when I do this!'

In one swift movement, Cassie rammed her cock deeper into Sam's mouth and into his throat and held it there. Much to her surprise, there was no retching or gagging at all. Either she'd completely obliterated his gag reflex, or he never had one at all.

'Oh my god, slut, your throat is sooo tight!' She exclaimed as she continued to lower herself in his throat. Inch by inch she went down, and still there was no negative response from him. If not for his curling toes and deep breaths, she would have thought she'd knocked him out.

Sam couldn't believe what was happening, and he knew that after everything he'd experienced, nothing should surprise him. But this did. He was taking her down his throat. It hurt like mad, his jaw, his neck, his throat, but he was taking it. And he could still breathe. Above him, he could see her large sack slowly getting closer and closer, becoming fuller with each moment. Eventually it was so close he could smell it. He gagged at the smell, his first gag in nineteen inches. As he gagged, he brushed her shaft with his teeth involuntarily.

'So even your throat has limits, slut? Shame, such a shame.' she said as she withdrew her cock all the way until only her leaking cockhead was still in his mouth. His tongue immediately went wild, tickling her all over. 'But now that you've used your teeth, you need to get punished.'

He gulped, swallowing a large amount of her sweet precum by doing so.

'The punishment is just as simple as the rule. Every time you use your teeth, I'm going to do this.' Cassie grabbed his spent balls in one of her hands and squeezed. Sam let out a shrieking whimper of pain around her cockhead, doing his best not to touch her with his teeth. 'Got it? Good. And remember, the round ends once I get this cock all the way down your throat.'

Sam steeled himself as she began to lower herself once again. He'd done fine up until her balls had touched his nose. He didn't know how much left there was but it couldn't have been much. All he had to do was get through the smell. Slowly but surely she entered him again, massaging the bulge in his throat her cock formed. He could feel it going deeper and deeper inside him. Her balls were drawing ever closer. They were almost near his face and... She pushed in. Hard. He felt his chin touch her flat belly. She was all the way in! The torture was over. Except she didn't move.

'Mmm, slut, this feels soooo good!' She moaned above him. 'I think I'll stay like this for a bit. You don't mind do you?'