A Jock in the Machine Ch. 11

Disclaimer: All characters mentioned in the story are over eighteen years old. Most of the main cast is exactly 18, but none are younger than that.

Chapter 11: There at the End-ish

'Hey.' Cassie pouted as she opened the front door.

'Just hey?' Tim raised an eyebrow. He'd picked that one up from Cassie without even realizing it. 'No kiss?'

'It's 9 PM. You made me wait all day long, so now...' She turned to walk back into the house. 'You'll have to earn it.'

Before she could even make a couple of steps, she felt Tim grab her hand and yank it backwards. It wasn't a forceful yank by any means, as Tim had always been gentle with Cassie. But it did have a great amount of purpose behind it. Spinning around, Cassie fell straight into Tim's arms. He in turn spun her around and pressed her back to the now closed door. Before she could say another word, he planted his lips on hers.

Cassie had planned to tease Tim a bit, make him really work for a kiss. She'd have of course caved quickly, but he'd completely turned her plan on her. And she found herself loving it. She'd nearly given up all hope on ever getting that sweet, fuzzy feeling she got when Tim kissed her. But here it was again. It made her toes curl and her arms fervently move all over his body as if to make sure he was really there. And just like that, it was over. Tim had really gotten good at ending his kisses just shy of Cassie losing her mind. She wasn't sure if she liked that at all. Either that, or she loved it.

'You could've let me have my fun for at least a bit!' She smiled, looking up at Tim's eyes.

'Nah, I had to wait all day for this, couldn't possibly wait longer.' Tim smiled back before continuing. 'Plus, this was fun, wasn't it?'

Cassie brought one of her hands to grasp her chin as if she was deep in thought. The other, however, still roamed Tim's body incessantly.

'Mmm, no.' Tim had just a split second to be shocked at her response before she got closer. 'It was hot. And I want more.'

Tim had been caught off guard and Cassie easily managed to pull him down to her. She wasn't wasting any time, her tongue finding his immediately after their lips connected. Tim's hands began moving on their own accord, but they were much more focused than Cassie's were, immediately travelling down her back and hooking under her butt, lifting her entire body up. Cassie thankfully took the hint and wrapped her legs around his back. Damn, he'd missed this, Cassie making him so hot just by being there. The tongue battling his helped too.

Entwined as the two were, it was a complete miracle they managed to make it up the stairs and into Cassie's room without breaking the kiss for even a moment or tripping and falling over. But they did make it, and it had been a spectacular sight, a hurricane of roaming hands, deep moans and clothes being hastily taken off and thrown around. By the time they'd made it to the room, the only things that were still on were their respective tops, a tiny white tank top that should have been fired for the abysmal job it was doing containing Cassie's ample breasts, and a simple T-shirt Tim's mom had so painstakingly ironed. Taking them off would have required the kiss being broken, and neither one wanted that to happen.

Once the duo had made it to the bed, and they only realized they'd gotten there when they tumbled over the edge and fell on the soft mattress, Cassie finally found some brief resolve to push Tim away.

'Before we... ohhh God... before...' She could barely form words let alone sentences. Laying as she was on the bed with Tim on top of her, she had the perfect support to bring her hands up and halt him when he went back in for the kiss. As much as she just wanted to let him get back to it, she had something to ask first. Something vital. 'Wait, please... just... one, ohh...'

Tim backed up. If she wanted to wait, he'd wait. And then he felt just how out of breath he was as well. Damn, the two must have really been going at it. They'd made out in school quite a few times the previous week and he'd never gotten tired from it, but now he could barely grasp for air.

'Before we continue...' Cassie spoke up. Tim had been able to match her in intensity, but she recovered much faster still. 'Did you, uhm, did you do as mom said?'

Oh. OH!

'Uhh...' Tim wasn't quite sure how to respond. Or rather, he didn't know how to best put it to words. 'No, no I didn't.'

Cassie's face went blank in an instant.

'You... didn't?' Damn it. 'W-why? Did it n-not fit or...'

'No, I didn't really try at all.' Tim looked at her and saw her entire body tense up. He quickly tried to explain himself. 'But that's only because-'

'N-no, it's fine. I... I understand.' Cassie sighed. She was barely holding back her tears. Damn it. 'My m-mom just forced you into it and...'

'Cass, wait, it's not tha-'

Cassie had retreated into her own little world at that point and didn't even register Tim's voice.

'Y-you just didn't know what you were getting, getting into' The first tear broke through the dam. Damn it! 'A-and it's normal that you wouldn't like it...'

'Cass, would you just lis-'

Cassie moved up on the bed, her back resting on the pillows.

'I mean, I knew you probably wouldn't, it's just... I hoped maybe you'd...' She wasn't even really aware she was talking, or what she was saying at that point. DAMN IT! 'B-but you don't and...'

'Cass, that's really no-'

'And you probably don't want me anymore either, and-'

A pair of hands gripped Cassie by the shoulders. Where his words hadn't managed to snap Cassie out of her trance, the good shake Tim gave her succeeded.

'Would you stop that already!' he yelled. The flash flood of escaping tears that ran down Cassie's cheeks stopped at the sound of Tim's voice. All Cassie could do was stare at him. 'Of course I want you! And I do like it!'

'T-then why didn't you...'

'Because I don't wanna do it with some stupid dildo, ok? I wanna do it with you! Is it really that difficult to understand?!'

The tears started back up just as abruptly as they'd stopped. But this time, they were tears of joy and relief.

'So, will you just relax? I'm not going anywhere, alright? Hell, I've been thinking about you all day!'

Tim wasn't yelling anymore. He'd stopped at the first hint of a smile on Cassie's face. Phew, that was a scare. But now there was business to get back to.

'Besides, it's not like I didn't do anything at all with that dildo...' Tim smirked mildly, hoping Cassie had seen it.

'W-what do you mean?' She spoke up meekly, still recovering from being on the verge of emotional collapse. The mere thought that Tim might not want her anymore had nearly broken her.

'I could tell you...' Tim's hands left her shoulders. They slowly made their way down her body. 'Or I could show you.'

Throughout the uncomfortability, awkwardness and emotional turmoil that had just taken place there had been one thing that had remained a constant. And now that Tim's hands had reached their destination, it was time to address the elephant in the room. Or rather, the elephant's trunk.

Before Cassie could say a single word she felt Tim's hands wrap around the one part of her that she could always count on to annoyingly betray her subtleness. The moment she felt his touch, all tenseness disappeared from her as she slid down a bit towards him, now laying entirely on the bed with just her head on the pillows. If she'd died right there and then, she'd have been perfectly fine with it. But Tim didn't stop with just grasping, no, his hands began moving. Cassie shuddered from the feeling, closing her eyes and biting her lower lip.

Once again, Tim found himself head to, well, head with Cassie's dick, and it was every bit as enormous as he remembered it. If it wasn't for his hands wrapped around it, he would have doubted his eyes that it was real. But barely being able to encircle around it with both hands made him certain he wasn't just seeing things. Having moved to sit on his knees between Cassie's legs, Tim slowly moved his hands up the enormous shaft. The low moan that came from her lips signalled that Tim was doing a good job. So, naturally, he continued slowly dragging his hands along the everpulsing length, feeling every single vein along the way. God, they were like a spider's web, but then again, they had to be to sustain such a beast and keep it so incredibly hard and burning hot.

'I've been thinking about this so much...' Tim involuntarily let out as his hands finally reached the bright purple tip of Cassie's cock. With how he was sitting, it came all the way up to his sternum, maybe even a little bit past it.

Hearing those words, Cassie opened her eyes. She would have spoken up, but she was too late - Tim's lips connected with her lower head. Oh God, they were so soft! She closed her eyes in bliss, but the feeling of her entire cockhead, swollen and pulsing as it was, being completely enveloped by Tim's mouth made her immediately open them back up. That's what he'd been practicing! The day before, he'd barely managed to get his lips around half her tip when her inhuman girth had blocked him from going further. But now, now he was taking the entire head in! And then some! With how large her dickhead was, Cassie had no doubts it was filling up Tim's mouth completely. And now that he'd taken a few more inches of her dick, she was definitely knocking on the entrance of his throat.

This was it. Moment of truth. Tim had practiced quite extensively on the dildo that Lara had given him throughout the day. Just a few moments ago, he was certain he'd be up for the task. But he hadn't imagined the real thing being so different. A cold plastic dildo couldn't possibly compare to Cassie's scalding hot, incessantly throbbing and leaking cock. Tim looked up for just a split second. It was enough. Seeing Cassie watching him, barely blinking in what he was certain was bliss, gave him all the incentive he needed. Taking a deep breath, one he was certain was going to be his last for a while, he dove forward.

Cassie squirmed on the bed. Her entire body began convulsing lightly. She'd had her dick sucked countless times, but it had never felt like that. It was like Tim's touch was making every single part of her infinitely more sensitive. She had to force herself to release her lip for fear that she might completely bite it off in her ecstasy. She leaned back in bliss, her hands tightly gripping the sheets. But she didn't want to stare at the ceiling while Tim was busy bringing her indescribable pleasure. No, she wanted to look at him, to admire him. But when she tilted her head down to once again do that, she found out that she no longer could: Tim had taken so much of her dick in his mouth and throat that his head was now hidden past the mountains that her breasts were.

Tim's eyes began watering. Damn it. He had, what, five, six inches at most left? But he just couldn't get them in. The need for air was becoming far too great. Still, it was a monumental achievement in his mind. Especially considering he hadn't managed to get past the halfway mark on the dildo at home. Pushing forward just one more time to check if maybe he'd manage to fully deepthroat Cassie by some sheer stroke of luck, and being met yet again with resistance, he reluctantly began lifting his head off her massive pole. Even though he was quickly pulling his body off her, it was still an insanely long way till he could take a breath again. Just long enough for a thought to pop into his head. A realization. He had absolutely no reservations about doing this. If it had been anyone else on the end of that gigantic cock he would never have even tried doing a thing. But it wasn't. It was Cassie that the dick belonged to. It didn't add to her, and it didn't take away, that's simply how Cassie was. And he'd do anything to please her. All of her.

'Wow...' that was all Cassie could say when her eyes finally met Tim's as he pulled his lips completely off her cock. Woefully understating just what she was feeling at that point.

'Yeah...' Tim said in between gasps for air. His breathing was normalizing rather quickly. Seemed like his body was enjoying things just as much as Cassie's. 'Sorry I couldn't get all of it down.'

'It's... mmm... it's fine.' What had Tim done to her? He was the one that had just had a foot and a half of dick down his throat, yet she was the one that was out of breath? 'I didn't... mmm... know you were so... adventurous...'

'Me neither,' Tim smiled. 'It's your fault, really. Still, I should at least make sure we get everything ready, right?'

Cassie propped herself up on her elbows.

'What do you me-' And she was instantly back down on the bed.

Damn, Tim had just perfect timing to interrupt all her actions. This time, it was the feeling of his tongue lapping around the last few inches of her dick that had remained dry that was the cause. God, he'd gotten so much of her down his throat, she couldn't believe it. People had gone deeper on their first try before, some even on their own accord, but none ever made her feel like this.

Tim didn't have to lick long to fully cover what little of her shaft had been dry. And then, he wasted no time going further still. Cassie's dick might have gotten a lot of attention, but there were other parts of her that hadn't. The moment he placed his hands underneath her sack, he heard Cassie gasp. Good, she was enjoying that too. But damn, her balls were even bigger than he remembered. They practically spilled out of his hands, and when he tried lifting them, he found out just how heavy they were. And how full. Had she really been carrying such a huge pair all this time? How did she even move, or cross her legs?

Tim's hands on her balls had been one thing, but his tongue and lips were a completely different beast altogether. Cassie couldn't believe just how lucky she was. After all the fuck ups and all the pain she'd caused Tim, he was now between her legs making her feel like she never had before. God, she knew he had gotten really good at kissing really quickly, but she hadn't expected those skills would carry over to him making out with her sack. But boy did they. He'd gotten the top of them completely slathered in saliva and had lifted them to lick the underside. God, just the feel of his breath on her skin made her tingle all over. He just had a little bit left to go and then... and then... Oh! My! GOD!

Tim felt the mattress shake repeatedly as Cassie punched it. On top of his forehead her balls churned even fuller. Her legs that had previously laid flat on the bed to his sides had now curled around the back of his head, pulling him in as close as they could. All that just from gently grazing her clit with his tongue? Then, Tim wondered, what would happen if he was to lick further down?

Cassie's eyes went wide. She sat up on the bed so quickly that she nearly headbutted her own rock hard and jutting dick. Oh God! He was... and it was... mmmhhh! She couldn't think. Her heels dug into Tim's back as she tried to pull him in closer.

Cassie's heels didn't hurt Tim at all, however. They just let him know he was doing a good job, and while it might not have been obvious compared to Cassie's thrashing all over the bed, Tim was enjoying his work just as much. It was almost the polar opposite of working with Cassie's cock. Instead of a titanic record-breaking pillar he had been met with the prettiest, pinkest small pussy he'd ever seen. Granted he'd only seen a pussy in porn, but he'd watched a lot of that, and none could ever compare. And instead of having to work his best to cover the entire thing in as much spit as he could, it had taken just the tiniest prod of his tongue to have Cassie completely gushing all over him. Two things were the same however between both of her sexual organs: both were incredibly hot, and both were delicious.

Tim had managed to stick his tongue as deep as he could in Cassie and was just about to withdraw and do it again. That's when he felt it. Cassie's fingers streaking through his hair as her hands palmed the back of his head. Her legs coming closer together, squeezing his head in between her thighs. Her entire body tensing up.

Cassie had never felt like that before, and in a night where she'd already found herself thinking that multiple times over, it still rung true. She knew exactly what it was and she was hating herself for not trying it out sooner. She'd cum immeasurable times from that huge ol' dick of hers, but now that she was finally having a vaginal orgasm, it blew all the loads she'd ever blown herself out of the water. It was rocking her entire body, sending tiny jolts to each and every nerve. God, she never wanted it to end! A tapping on Cassie's thigh broke her out of her orgasmic trance. Oh crap! Tim!

Tim coughed and gasped for air as he stood back up on the bed. That was two times that night that he'd nearly blacked out on his girlfriend. That wasn't good enough. He needed to work on his breathing. Still, he'd managed to get her to cum, and that filled him with pride. But in front of him, Cassie's dick throbbed even more menacingly than it had. Seemed Tim hadn't finished the job completely.

'Hey, Cass...' Cassie didn't respond. She couldn't really form words still, though she did manage to at least turn to look at him. 'I know you just, uhh, came, but, uhh...' Come on, damn it, just say it already. 'Do you, uhh, want to go again?'

Cassie's gaze never left Tim's as she nodded. It was as if he had completely hypnotized her. She'd have agreed to anything he asked her at that point.

Tim's words had registered in Cassie's mind, despite her not showing any signs of it. Whatever he was going to do next, she'd love it, she was certain. Whatever part of her body his lips touched next, she'd... She'd... Tim hadn't meant his lips! He was turning around! Right before her eyes the boy she loved turned around and propped himself on all fours on the bed. This was it... this was it!

Tim tried to relax. That was much easier said than done. For all the stretching Cassie's mom had given him, Tim had made the conscious decision to let Cassie stretch him out to the limit herself. And as much as he loved her and wanted to do it all for her, he couldn't deny that he was absolutely terrified. Not only because it would hurt like hell. But also because once they've gone past that limit, everything between them would change. And he had no way of knowing if they'd change for the better, or worse.

The feeling of Cassie's wet, spongy and entirely too thick tip pressing against his ring snapped Tim out of his thoughts. A pair of shaky hands soon gently gripped him by the hips. Seemed like Cassie was just as frightened as he was. He just needed to let her know everything was fine, relax, and get skewered.

'Come on, Cass, I can't wait any longer.' That was a lie. He definitely could wait, but he knew that even if they waited they'd have to do this eventually. So instead he was going to encourage her to act. 'Do it.'

He'd expected Cassie to thrust forward upon hearing that. He'd prepared himself for it. But she didn't. Her cockhead didn't move at all. The only thing that moved were her hands, off his hips.

'D-don't say that... please.' Cassie spoke in a low voice, still exhausted from her orgasm.

Unfortunately for her, it was far too low for Tim to hear it. He was too focused on breathing steadily in preparation to hear her.

'Come on, Cass, don't make me wait!' He insisted. That's what she wanted, wasn't it? What did she want him to do? Beg? Because he'd beg. 'I'm begging you.'

'N-no, please, stop sayin-' Cassie had cupped her eyes before, but she now moved her hands to block her ears. She was too late.

'Fuck me!' Tim shouted out. He'd said it, now was she finally going to do it or wha-