A Jock in the Machine Ch. 06

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Cassie and Tim finally go on a date. But will it be good?
6.2k words
4.28
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Part 7 of the 13 part series

Updated 06/10/2023
Created 07/22/2020
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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 06: Shifting Gears

'Ugh.' Cassie sighed as she shifted anxiously in her chair. It was one minute past three.

Tim had told her he'd be there to pick her up at three. Well, he'd said around three, but Cassie wasn't about to take any chances and not be ready. Even though she nearly did that, by obsessing over what to wear for the better part of two hours. She'd originally gone for a dress, then immediately reconsidered, thinking it too formal, swapped to jeans and a t-shirt, and immediately thought it was too casual. And then she repeated the same process over and over a few dozen times over the next couple hours. In the end, the outfit that stuck wasn't even her choice really. It simply won the war of attrition as Cassie ran out of formal clothes to swap back to. Every single article of clothing that Cassie had discarded lay in various piles around her room. She'd worry about them later. Tim would be there soon, and she had to be ready for him.

Makeup took far less time. She hadn't worried much about it. A bit of blush on the cheeks, a faint purple eyeshadow and liner and she was done. Then the dilemma of what to do with her hair came upon her. Pigtails? Nah, too slutty. Pony tail? Could do, but maybe... Braids? Nah, no time! In the end, with only two minutes left to three o'clock, she'd just left it down, hanging just a few inches past her shoulders and down her back.

She'd put so much effort into being ready on time for Tim, and he was late! It was now two and a half minutes past three. Cassie was intently staring at the clock, noting each second passed. If that boy didn't show up soo-

The doorbell rang out. Cassie practically leaped off her chair, nearly sprinting to the door. She took just a second to compose herself so that Tim wouldn't realize just how much she'd been waiting for him. Of course, the sound of her quick footsteps was still a dead giveaway.

'Hey Cass' It was all Tim managed to say before Cassie came fully into view as she opened the door. He'd planned on something witty to say but seeing her made him forget all about it. Her looking good shouldn't have surprised him anymore, but it still did. She'd put on the tiniest pair of jean booty shorts he'd ever seen, and they looked amazing. Above them, a dark gray tank top left both her waist and midriff fully exposed, and showed a splendid amount of cleavage to boot. The open plaid shirt she'd put on to bring a bit of modesty to her outfit barely registered in Tim's mind.

'You're late!' Cassie crossed her arms under her breasts. While it did make them stick out even more, and Tim would've loved to just stare at them, he really didn't want to start off the date like that. Still, with her face being just as beautiful as the rest of her, he wasn't disappointed to look up at her. 'You said you'd be here at three.'

'I said around three, all right?' Tim chuckled.

'I don't care. You made me wait. Now you're going to pay me back for it.' Even though she was doing her best to sound angry at him, Cassie was quickly turning into her usual playful self when around Tim.

'Oh yeah? And how do you want me to do that?' Tim stepped in closer.

'Mmm, I can think of a few ways.' Cassie finally closed the door behind her and locked it.

She leaned back against the door just in time for Tim to fully close the distance between the two. The two had made such amazing progress, a full minute without jumping on each other. Yet all that progress went to waste as their lips connected and their bodies intertwined. Now that was certainly the best way to pay Cassie back.

'Mmm, as much as I really want to just invite you back in,' Cassie said as she broke the kiss. She bit her lower lip before pushing Tim gently off her. 'You promised me a date. I'm getting that date.'

'Sheesh, I thought you wanted me to pay you back.' Tim chuckled. He definitely wouldn't have been against her inviting him back in. 'So, where do you wanna go?'

'What do you mean, where do I wanna go?' Cassie looked him over teasingly. 'You're the one taking me out. That means you plan out the date, take me on it, and if I like it I might let you take me out again.'

'You could have told me that last night, you know!' Tim really hadn't thought this far ahead. And sure, Cassie wasn't being serious. But he did want to make the date great regardless. 'Hmm, where can we- Oh! We can go to the amusement park!'

'That's your big plan?' Cassie giggled. She liked the idea. She just wasn't going to let him know it yet. 'And since when is there an amusement park in town?'

'It opened like, uhh, two years ago? Not sure exactly.' Tim moved in closer to Cassie again. She held her breath as she saw him close in, expecting yet another kiss. She was surprised, and almost disappointed, when instead of going in to kiss her Tim wrapped his hand around her waist and pulled her off the door she was still leaning on. 'C'mon, it'll be fun!'

'Fine, fine!' Tim's eyes were almost glowing with excitement. Even if Cassie hadn't wanted to go, and that definitely wasn't the case, she would never have said no upon seeing him so excited for it. 'But you're winning me a prize!'

------------------------

'I was joking about that prize, you know.' Cassie pouted. Tim had just missed the stacked cups. Again. For the third time. 'C'mooon, let's go already.' She said as she pulled on his arm. It was no use, he was already getting money out to try again.

The whole amusement park date had gone much better than Cassie had expected. The park was absolutely huge, and it was packed full of people. Probably because it was an actually sunny and warm day, something quite rare that late into autumn. Groups of friends, families with their kids, other people on dates, all were enjoying themselves on the various rides, shops and attractions.

Cassie and Tim had gone on a few rides as well. They'd started out slow, the Ferris wheel, then the spinning teacups, then one of the slower roller coasters. But Cassie had quickly pressured Tim into going to the more extreme rides. He really wasn't a fan of those, but he did make her come with him, and he sure as hell wasn't going to tell her no. So, accepting that he's going to scream like a little girl, the two had headed for the park's most prized ride: A 160 foot drop tower.

The drop tower was a sight to behold even if one wasn't getting on it. The insanely tall structure towered over everything in the park, and over most of the town as well. People had said the view from the top was amazing. If only one had any time to enjoy it before being plummeted down towards the ground at insane speeds over and over again.

Cassie and Tim had waited in line for the tower for over ten minutes. It seemed like the moment Cassie had pressured him into going, the entire park had uniformly agreed to get there before the two. All the waiting in line had quite a different effect for the two. The closer they got to the tower, and the more times it went up and down, and the louder people's screams became, the more Tim got terrified of it. But Cassie, Cassie only got more and more excited. She was positively buzzing once they finally managed to get to the front of the queue.

That one inch of height Cassie had gained when she was 14 proved a lifesaver, as it meant she was over the "You must be this tall to ride" requirement by, that's right, exactly one inch. She nearly swept a reluctant Tim of his feet once they were allowed on the ride, sprinting to it to take their seats. And then the biggest downer of the day happened.

See, to get on rides that go at high speeds or dangerous angles, one needs to be properly secured to them. On this one tower the town amusement park had, the method they used to secure people was a metal harness that came over the shoulders and above the chest. Standard stuff, nothing too uncommon. The problem, however, was that it was incredibly tight to the body, so that people wouldn't get lifted off their seats when they came crashing down to the ground. And in Cassie's case, this meant it was incredibly tight on her breasts. The metal bars dug into HH cups painfully, and even then they couldn't properly close. Cassie just couldn't get strapped in. The ride crew had tried their best to accommodate her, but without the proper safety precautions, they eventually had to force Cassie off the ride, much to her overwhelming disappointment.

Tim had been relieved that he no longer had to go on the ride he so desperately didn't want to. His relief hadn't lasted long as he had seen Cassie's pained and sad expression as she walked away from the ride. She had really, really, REALLY wanted to get on it, and she wasn't allowed. Thinking as fast as he could, he had pulled her away from the crowds and led her to the part of the park that contained all the games. She'd barely looked anywhere other than at her feet the whole walk there, but once they finally stopped, she peaked up. It was one of the most classic fairground attractions - try to knock over a stack of upturned cups with a ball, win a prize. In the case of the one in front of them, knock over three stacks with three balls, win a giant pink teddy bear. And by giant, it meant almost as tall as Cassie. Her eyes had lit up seeing it. But then Tim had completely missed the first time he tried to win it for her. And then the second. The third one he barely knocked over half the cups in the first stack.

'Just a few more tries, Cass.' Tim said as he threw the ball for his fourth try. He missed completely yet again. His aim had gone quite poor. 'Again!' He handed the clerk another five dollars.

The game, of course, was rigged, as many games like it often are. Cassie knew it, and she really didn't want Tim to spend any more money on it just so he could cheer her up. In hindsight, she really shouldn't have gotten so upset over a stupid ride. And now, Tim was spending all his money on-

The ball flew directly into the between the two cups on the lower right. It knocked them down, and the rest of the followed. That was the first pile down.

'There we go.' Tim chuckled as he aimed at the second stack. 'Just had to get my aim right.' He threw the ball, this time aimed at the lowest left cup. The stack crumbled under its own weight once the cup flew off the table.

Cassie and the game clerk were both stunned, mouths open as Tim almost effortlessly got two of the three stacks down, when other people rarely got past one.

'And the last one...' The ball came flying, this time aimed dead center of the stacked cups. And sure enough, just like the last two, once the center of it this time was gone, the other cups followed suit. 'There. See, Cass, told you I'd win you a prize. Now, which one do you want?' Tim turned with a cheeky smile. Cassie, still stunned, couldn't respond verbally. She just pointed to one of the largest teddy bears, a light blue one. Somewhat reluctantly, the clerk took it down from the shelf and handed it to the two, still in disbelief. He'd worked there for well over a month, and so far not a single person had even come close to getting one of the big prizes.

'Hey, Tim?' Cassie spoke up as the duo headed away from the booth. 'How'd you do that?'

'What, the game?' He looked down at Cassie as she nodded. She was really hugging that teddy. 'Well, I may have worked at that particular booth over the summer...'

'Wait, really? So you cheated?'

'I didn't cheat, Cass. I just...' Tim put his finger up to his chin to drive home the point. 'Have a bit more insider info than most. We're lucky the owner wasn't here or he'd never have let me play. You feel better now?'

'Yeah...' Cassie suddenly stopped in her tracks. Tim turned around to look at her just in time to see her face getting closer. 'Thanks.' She said as she gave him a quick kiss.

------------------------

After that small little hurdle, the date had continued as before - amazingly. Much to Tim's relief, Cassie had stopped pushing for the scarier rides. The two'd just walk around the entire park, taking in the sights. It really was packed on that day. Amidst the masses of people, Cassie and Tim once again, as per usual, stuck out. Except this time it wasn't due to the two being overly into a kiss, or Cassie showing people not to mess with her. It was simply because of the massive teddy bear she was lugging around. It was quite weird, actually. Cassie had been used to turning heads and making people jealous, but that was usually due to her looks, not due to a giant stuffed animal. If the plush toy wasn't careful, she might consider it competition.

The duo were just leaving a photo booth where they'd taken pictures in dramatically oversized hats when they finally saw someone familiar. Tim had really struck gold with the idea of coming to the amusement park on a date. He was definitely not the only one: Right as they had turned to leave, someone poked Cassie on the shoulder. She turned around, already pissed at whoever had done that only to be met with Clive's grinning face.

And for a change, he wasn't alone. Right by his side, as Cassie was much more used to seeing him, was Terry. Cassie immediately jumped to give him a hug, leaving Clive and Tim to awkwardly look at each other.

'It's good to see you too, Cass' Terry said as he tried to gently nudge her away from him. Not that he minded the hug or anything. He could however clearly see Tim's rather uncomfortable expression near them.

'I haven't seen you in like a week!' Cassie exclaimed as she finally let go. 'Where've you been?'

A small "ooph" escaped Clive's lips. Cassie turned around to face him just in time to catch him scratching the back of his head.

'Cass, let's no-'

'Ah, chill out, will you?' Terry interrupted him, taking him by the hand. Well that was certainly some progress, from two guys who couldn't even admit their feelings less than a week ago to being so open in public now. 'It's fine, Cass. I, uhh, was taking care of my lil' bro.'

'Your- Oh! I'm sorry! I forgot!' Cassie instinctively put her hands up to her mouth in shock, which just caused her to stuff her face full of teddy bear.

'I said it's fine, sheesh! You're worse than him!' Terry nodded at Clive. 'Oli's fine now, alright? He just gets too anxious easily, but he's fine. Should be back in school on Monday. Now can the two of you just drop it already?'

'Okay, okay, sorry.' Cassie turned back towards Tim, who hadn't moved at all since seeing the two. She pulled on his elbow to come closer. 'Have you two met yet?'

'Cass, we go to the same school,' Tim protested. 'Everyone's met everyone.'

'Yeah but you weren't my boyfriend when you two last met, were you?' Cassie gave him a playful look. 'So, Tim, this is Terry. And Terry, this is my boyfriend.'

'You don't have to go around telling everyone that, Cass.' Tim wrapped his hand around her waist and pulled her next to him. 'I'm not a toy, y'know.'

'Mmm, no, you aren't.' She closed in for a kiss. Instead of kissing him however, she stuck her tongue out at him playfully. 'But you are mine, though.'

'You two are just so cute.' Clive teased them, making sure to get his voice as high as he could for the last part.

'Oh, shut up!' Cassie quickly gave him an annoyed look. 'And what about you two, huh? Holding hands in public? What would people say?'

'Oh, we've done so much more in public by now.' Clive chuckled as he took Terry by the waist, emulating what Tim had done to Cassie.

'Wait, really?' Her eyes lit up upon hearing that.

'Well, not as much as you two, but yeah.' Terry added. He didn't look uncomfortable at all admitting it. It was a huge change from how he'd been days ago. 'See, Cass, you're forgetting one big important detail.'

'What's that?'

'You can count on one hand the number of people bigger than us...' Terry began. And just like old times, Clive finished his sentence.

'Anyone got a problem, they're free to let us know.' He chuckled, turning around to briefly kiss Terry. 'So far, no one has.'

'Well, whatever works then. I'm really happy for you two.' Cassie smiled warmly.

'Yeah, me too.' Tim added. This was a first for him. He'd be ashamed to admit it, but seeing Cassie being so friendly with the two had gotten him at least a bit jealous. But seeing the two together, how they held each other and how they looked at each other made all his doubts disappear, for he recognized in their displays of affection the same ones he and Cassie were giving each other. 'So, what are you two doing now?'

'Oh, uh, we got a bit sidetracked coming here, to be honest.' Terry let go of Clive as he remembered their original plan for the day. 'We were supposed to be looking for a gift...'

'GIft? For who?' Cassie piqued up.

'Uhhh... Sam.' Clive added, somewhat quieter. He was very well aware of the history Tim, and especially Cassie, had with Sam.

'Oh...'

'Yeah, he got a conditional offer for college on Friday, so he's throwing this huge party tomorrow to celebrate.' Terry took the reins again, sensing the discomfort the talk was giving both Cassie and Clive. 'Speaking of which, you two wanna come?'

'To... Sam's party?' Tim looked at Cassie. She was just as surprised as he was. 'I, uh, I don't think we're invited.'

'Nonsense. We're allowed to bring whoever we want.' Clive interrupted him. 'So we want you two there. Plus Sam isn't going to know, he's been drunk since last night.'

'Thanks for the invite, guys.' This time it was Cassie's turn to interfere. 'We'll think it over. You should probably get going, though. Shops closing soon.'

'Yeah, we should.'

The two couples said their goodbyes and split. When Terry and Clive were finally out of earshot, Tim turned to Cassie.

'We're not going to that party, right Cass?' He really hoped she wouldn't want to go. He certainly didn't, but if she wanted he'd have a hard time saying no.

'Of course not!' Phew. That was a relief. 'Why, did you want to?'

'N-no, definitely not!' Tim laughed, easing himself. 'Can we change the subject, please? Like what do you wanna do now?'

'Hmm, I don't know, really. We've been all over the park and-'

A low rumbling noise interrupted Cassie's line of thought. Her eyes darted down, then immediately back up at Tim. He'd heard it as well.

'Hey, Cass, are yo-'

'Sorry, sorry, oh my God, I'm sorry!' She blushed immediately, her face turning the shade of an over-ripe tomato. 'It's just that I was so focused on getting ready and being on time and then I-' She started walking around frantically, barely even looking at Tim.

He'd had enough of her worrying over something so trivial. Quickly stepping behind her, he hooked his arms around her waist and brought her in close to him.

'It's fine, sheesh. You're cute when you worry but this is a bit too much.' Cassie jittered in place for a few seconds before finally calming down. 'So, you haven't eaten at all today?'

She shook her head, still embarrassed.

'Well, since we're still on a date, how about we go do just that? Anything you want in particular?'

'Idunno.' She finally spoke up, her voice low as she covered herself with the teddy bear.

'Come on, stop being so embarrassed, it's really nothing!' Tim squeezed her closer. 'There's this great sushi place nearby, you wanna go there?'

'Can it be something else? I, uh, don't really think I like sushi...'

'You don't think you like it? What's that even mean?' Tim laughed. He'd seen shows and stuff online about girls being indecisive but hadn't really paid them much attention. And here was Cassie doing just that.

'Well, I haven't actually had it but it's just raw fish isn't it?' Cassie finally confessed, her cheeks losing just a bit of their bright red color.

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