A Jock in the Machine Ch. 10

She'd meant to hug him tighter after saying that. She hadn't counted on him wrapping his arms around her in turn and pulling her closer first.

'I won't.'

A couple of minutes passed. The two didn't move. They didn't even speak. They just stood completely still embracing each other. And even so, for all the peace and stillness around them, they could still feel each other's heart pounding wildly away in excitement.

'So...' Cassie broke the silence first. It had felt nice to stay like that for what felt like several hours to her, but there were still things they needed to talk about. 'What now? Do we... just go back to how things were?'

'No.' Tim let go of her. They really did have things to discuss. He slowly moved over to sit on her bed. 'I, uhh, I think that's where we've been going all wrong.'

'What do you mean?' Cassie moved over to sit next to him.

'We've been acting like nothing's changed, you know. Like everything is like it was before you left.' Tim turned to look at her again. 'But it's not like that anymore. Things have changed. You've changed, I've changed. So I think we shouldn't pretend like everything's the same. Don't know if that makes any sense to you.'

'Surprisingly, it really does.' Cassie smiled back at him. If she was just doing it to be polite or if it really made sense to her, Tim couldn't tell. 'So, we should just, start over?'

'Yeah, I think so.'

'I don't think I know how to do that.'

'Me neither.' Tim sighed, looking at the wall. 'I love you.'

'I love you, too.' Cassie rested her head on Tim's shoulder.

'That was it.' Tim chuckled.

'Mm, what was?'

'That was the start.'

Cassie tilted her head up to look at him.

'You telling me you love me was the start?' She smirked. 'I knew that. I've always known.'

'Well, yeah, but that's the first time I've told you since we started over.' Tim wrapped a hand around her shoulder. 'Come to think of it, we haven't even had our first kiss yet!'

Cassie stifled a giggle. This whole thing was so dumb. And it was so working.

'Well, sure, but what comes after the kiss?'

'After it?' Tim closed his eyes as he slowly went in for that kiss he'd talked up. 'We'll think of something.' he slowly slid his free hand up Cassie's pajama covered leg, inching closer and closer to her cro-

'Well, well, you two sure work things out fast.'

'Mom!' Cassie leapt back in shock. Sure enough, there she was, Lara standing right by her door. 'What are you doing here?!'

'I live here.' Lara smirked. To Tim, it looked incredibly strange, not even half an hour ago she'd been shouting at him to get him to move and act, and now she was just making jokes? 'More importantly, what are you two doing?'

'Nothing! Get out of my room!' Cassie reached behind her and threw a pillow at her mom. A pillow that she easily caught.

'Mhm, don't believe you at all.' Lara said as she fluffed the pillow a few times and set it aside. 'I think the two of you were about to have sex, weren't you?'

'No we weren't! We were-'

'Yeah.'

'Tim!'

'I'm pretty sure she already knows, Cass.' Tim nodded meekly as Cassie gave him a look of pure surprise at his admission.

'It was pretty obvious really, with where your hand was going, Tim.' Lara's smirk became even wider. Yet her voice was completely serious. 'Do you even have any idea what you're about to get yourself into?'

'I know Cass has a, uhm...' Tim couldn't quite say the words.

'A dick?' Thankfully, Lara knew exactly what he meant.

'Yeah.'

'And what did you think you were going to do with that di-' Lara couldn't even finish her question before another pillow came flying at her.

'Shut up, mom! We weren't going to do anything with it if he didn't want to! Stop butting into other people's li-'

'Uhh, Cass, actually, I, uhh...' Just as Cassie had interrupted her mom, she was now herself getting interrupted, by Tim no less. 'I wanted to try it.'

'Wait, are... are you serious?' Two weeks ago she'd have jumped at the thought of getting to bone Tim. Now though, with everything that's happened, Cassie wasn't so excited. Especially with her mom in the room. 'Why?'

'What do you mean why? Because I love you, all of you!' Tim looked almost shocked at her question. But immediately after, he lowered his head. 'But I guess there's one more thing. After, you know, Monday and Tuesday, I, uhh, I just keep thinking back to it and I just don't want to do anything that reminds me of it, you know? Including the sex.'

Suddenly, Cassie gloomed down.

'No, no, no, I didn't mean it like that, Cass!' Tim immediately apologized. Damn, his choice of words was poor. 'I wanna do it with you, just, you know, not, uhh, me doing you. Fuck, what I mean is-'

'Need some help finishing that sentence there, Tim?' Lara interrupted. She could see how uncomfortable discussing sexual things was for Tim. It was quite precious, just how innocent he was, even after everything.

'No, he doesn't! I get it, okay!' As if on cue, Cassie snapped back at her mother. She'd have thrown another pillow at her, but regrettably was all out.

'So then, dear, what are you going to do about it?'

Both Tim and Lara looked at Cassie. She blushed a deep red color almost instantly.

'Well, uhh, if Tim's sure about it...' Tim nodded. Damn, he was sure. 'We're just going to... We're not doing it with you in the room, mom! Get out!'

'Not until you tell me how you're going to handle this.'

'What?! Get out!' Cassie reached over and grabbed her teddy bear from the side of the bed. The same teddy Tim had won for her. It too flew directly at Lara, and was just as ineffective as the pillows. Her mom wasn't going to budge on this. 'We're just gonna do it, alright? Now get ou-'

'No, you aren't.'

Cassie gasped. What, was her mom going to just forbid them now? She had no right to do tha-

'Listen, honey.' Lara continued before Cassie had had a chance to respond. 'I know I haven't given you the best of advice recently, but you should at least listen to the one I gave you last week.'

'Which one do you even mean?' Cassie was having none of it. She just wanted her mom out of the room. She wasn't even in the mood for sex any more. Her mom had completely ruined the moment.

'You should ease him into it.'

'Oh, great advice, mom. I don't even know what that means!' Cassie shouted out. Ugh, why wouldn't her mom just leave them alone already?

'I can see that.' Lara's smirk was replaced by a very stern expression. She'd gotten to the really uncomfortable part. She just had to follow her own advice now. Ease them into it. 'Thankfully, I'm here to prevent you two horny idiots fro-'

Lara actually caught herself that time. But it was too late - she'd let slip the wrong word. She truly hadn't meant to, but it was too late. She knew exactly what was coming. And she was right. In almost perfect unison, both Tim and Cassie leapt up from the bed, shouting at her.

'SHE'S NOT AN IDIOT!'

'HE'S NOT AN IDIOT!'

Cassie and Tim looked at each other immediately. None had expected the other to say that.

'You two are just so cute when you do that!' Lara couldn't help but let out a giggle. Which, of course, ruined the moment for the two of them. But she had business to get back to. 'As I was saying, lucky for you that I'm here to make sure you two don't do something stupid and ruin things.'

'What's that even mean?' Cassie's eyes suddenly went wide. 'Oh, no, no, no. You are not fucking my boyfriend!'

'Cassandra! What the hell are you even saying! Of course I'm not!' Dear God, sometimes her daughter just said the stupidest things. It seemed subtle clues weren't going to be enough to get to her when she was all angry. Lara would have to be blunt. 'Sorry about that, Tim. I really am. But, I have to ask you, do you happen to know what my job is?'

Just as Cassie had somewhat calmed down from her outburst, her eyes went wide again. That's what her mom mea-

'Uhm, no, ma'am.' Tim shook his head.

'Why don't you tell him, dear?'

Oh, damn it. Now her mom was making her say it. She had definitely planned this.

'She sells, uhh, adult stuff.'

'Really, honey?' Lara raised an eyebrow at her daughter for just a moment before turning back to Tim. 'I sell sex toys, Tim. Dildos mostly.'

Tim didn't reply. He wasn't really sure what he could even say in this situation. He had no idea why Cassie's mom was even telling him this.

'And we're going to use said dildos to get you stretched out for my daughter.'

Oh.

'What! WE aren't doing anything like that! I can d-' Cassie wasn't allowed to finish her sentence, which at that point had become the norm in the situation.

'No, honey, we are. I'm not letting you rush things and ruin them. And trust me, this is going to be just as uncomfortable for me as it is going to be for the two of you. But it's for the good of both of you.' Lara sighed. She hoped she wouldn't really have to do anything else to convince them. She knew it was foolish to think that, but it was incredibly awkward for her to even talk about that. 'So, if you two would please just come downstairs with me and we'll-'

'No way! We're not doing that, that's insa-'

'Cass, maybe we should do as your mom says?'

Oh come on! Cassie really hadn't expected that. She had hoped Tim would back her up in this, but he wasn't. And the worst thing was she knew that she'd have to agree to it now, too. For him.

'If your mom says it's for the best, I want to be ready for you.'

God damn it, she had no way out. He was already doing it for her. And she was definitely not going to let him suffer alone.

'Fine. Just, once we're done, please never speak of this again.' Cassie pleaded. Both her mom and Tim nodded.

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

A few minutes later, Cassie and Tim were waiting in silence in the living room. They weren't really looking at each other: Cassie was fidgeting with her nails in anxiety, while Tim just looked all around the room. Both were feeling uneasy already. Just when they'd almost reached a point where they'd call the entire thing off, Lara emerged from the basement. She'd gone down there to get the things she needed, and she was now back with a large cardboard box, with different size dildos sticking out of it.

'Right, sorry for the wait kids.' Lara tried to calm the two down, as she could feel the discomfort the two were in. 'Now, I'm going to need you two to do exactly as I say, and we should be done rather quickly. Okay?'

Cassie and Tim nodded. They had gotten that far. They just had to go through a few more awful minutes. There was no other way. Tim wanted to do it for Cassie, and she wanted to do it for him. They were stuck.

'Splendid. Now, Tim, please take your pants off and get on the couch on all fours.'

Fuck. That did not sound good. Not to Cassie. Not to Tim. Especially not to Lara. She'd really hoped her daughter would've just figured how to do things on her own, but that hadn't been the case. Fortunately for her, despite the uncomfortable tension, Tim obeyed. Within half a minute he had taken up the requested position on the couch, head towards Cassie; bare, exposed butt towards her mom.

'Now, Tim, I want you to take a deep breath and relax.' Lara said as she put a pair of latex gloves on. Tim did as instructed. For Cassie. 'This will probably hurt. There's no other way. If you want to scream, go ahead.'

Lara rummaged through the box and took out a large bottle of lube, which she proceeded to pour some of on her index finger. Once she was satisfied with how wet it was, she poured some of the liquid on Tim's entrance. She was lucky, as either he shaved regularly or just didn't have any hair at all down there. The cold feel of the lube made Tim shudder, but he quickly tried to relax again. He managed to do that just in time, as he felt Lara's gloved finger push against his ring.

'There you go. You took it like a champ! Not even a grunt.' Lara tried encouraging Tim. Perhaps that would distract him from thinking about what was happening. She wasn't kidding either. Her finger had slipped inside rather easily. She only hoped the rest would be similar.

After moving her finger around Tim's anus for a few seconds, making sure to get as much of the lube off her finger and stuck to his insides, Lara pulled out slowly. That one elicited a small huff from him. The situation was far too awkward for anyone in the room to properly recognize what that huff really was: a moan.

'Do you need a minute? Or can we go on?' Tim nodded for her to go on. Cassie had slowly gotten closer to him. He took her hand in his, to remind him why he was doing this.

Without saying another word, Lara pulled the first dildo out of the box. It was five inches long, and just a bit thicker than her finger. Once again, she lubed it up and pushed it in.

'Nghh.' Tim grunted loudly. That one wasn't as easy to let in as Lara's finger. But he fought through the pain and did his best to relax. After a few more attempts, the dildo was successfully pushed deep inside him.

By that point Cassie had moved over until she had one knee up on the couch. Hearing Tim grunt in pain like that made her want to just call everything off. If he was hurting already, she didn't want him to suffer further. But Tim just held her hand tighter. She knew he wasn't about to give up, and as such, neither was she.'

Lara kept the dildo inside Tim for a few minutes, until she could see his body relax and his breathing return to normal. Then she knew it was time to proceed. She didn't even ask Tim that time. Speaking just made things even more unnecessarily awkward. If either of the two wanted to stop her, they'd tell her.

The next dildo up looked much bigger than the last: almost nine inches long, and nearly twice as thick as the five inch one. Upon seeing it, Cassie's eyes went wide. Tim turned his head up to look at her and managed to catch her startled expression for just a split second before he felt the dildo enter him. Fuck that was something completely different. It hurt like mad, and his body was desperately trying to not let it in, despite Tim's best efforts to relax. His breathing quickened, his free hand clenched in a fist that he slammed in the soft cushion. The one part of his body that he could control was his other arm. He made sure not to squeeze Cassie's hand any tighter, or he might end up hurting her.

After what seemed like far longer than it was, Tim's body got used to the new entrant. And just as it did, it was pulled out. The sudden withdrawal made Tim break eye contact with Cassie and his gaze fell upon...

'Cass...' Tim spoke up in a low hushed voice.

'Yeah?' Cassie replied in much the same manner.

'Are you, uhh, getting hard?'

Everything in the room came to a complete standstill. Cassie immediately looked down and gasped. Lara, stunned, looked over Tim's body and her eyes fell upon the same thing that Tim's and Cassie's had - the long bulge that had formed in the right pant leg of her daughter's pajamas. Cassie's cheeks turned into a dark, deep red color.

'Oh my God! I'm so sorry! I didn't mean to! It's just that... I'll just go upsta-'

'Don't go. Please.' Tim interrupted her, his hand still holding onto hers and his eyes still transfixed on the bulge. He knew she was going to be big, Sam had told him while drunk. But he hadn't imagined it like that! 'Cass, can I... can I see it?'

Cassie blushed even harder, her cheeks starting to turn almost purple in embarrassment. Yet despite her embarrassment, her body was betraying her. A very obvious throb shook her pants at the sound of those words, a throb that the entire room saw. Cassie looked at her bulge, then at Tim, then at her mom, trying desperately to find a way out of the whole thing.

'Well, come on, honey.' Her mom finally broke the silence. 'You'll have to show him eventually, you know.'

Fuck. She was right. Cassie knew it. She should've been ecstatic at Tim wanting to see her, all of her. But now that it had come to it, there were two things she was feeling: shame, and fear. Somewhat reluctantly, she stood off the couch and hooked her fingers in the elastic band of her pajama bottoms. She took a deep breath and pulled them down.

Tim's eyes went wide. Wider than they had been before. Wider than they had ever been. Holy fuck! It was massive! No, not it, her! Cassie wasn't an it! But fuck, her dick was something he would never have though possible if he wasn't looking at it with his own two eyes. He looked up to make sure he wasn't dreaming or seeing things. The sight of Cassie cupping her eyes in shame and her bright purple cheeks made him certain this was no illusion. He returned his gaze lower and oh my God it had gotten even bigger! It was already as thick as a can of beer and reaching her knees! And it wasn't done growing! The realization that Cassie's mom was preparing him to take all that suddenly dawned on him and he immediately turned around.

He was met with something he hadn't expected at all. And by that point, he was pretty sure there was nothing else that could surprise him. Yet the sight of Lara pulling a large, thirteen inch dildo out of his ass was not something he was prepared for. Pulling! Not pushing! He suddenly felt his butt muscles contract and felt just how much he'd been stretched out - he'd been so transfixed on Cassie's cock that he'd completely missed Lara putting the next dildo in him.

This was insane! Tim turned back towards Cassie, who still had her hands cupped in front of her eyes. She really couldn't dare look at him at that point. Yet her body had no issue continuing to entertain its audience: her dick had gotten hard enough to start rising up, now sticking out in front of her body. With it like that, Tim could also see under it, and he was intently staring there, right at her balls. Balls that were so unbelievably large, he wondered how they had never slipped out of her underwear when she wore short skirts. They were unreal! Huge, full, completely hairless and hanging a third of the way down her thigh.

Cassie's body seemed to like all the attention it was getting. Out of the corner of his eye, Tim noticed her pole throb. Hard. He turned his gaze slowly, his eyes running along the entire length of Cassie's immense cock. The crisscrossing, pulsing veins covering the entire length made him certain that she was finally rock hard. Fuck, one of the veins was as thick as his pinkie finger! The path down her length seemed to take forever, there was just no end to that dick. But finally, after looking over nearly two feet of unreal cock, Tim came face to face with Cassie's other head. It had turned a deep purple color and swelled up bigger than his fist. And it was no more than two inches to the side of his face!

Cassie was in hell. She absolutely hated her body at that point. The situation had been bad enough as it was without her getting a mad erection. She had no idea what had even caused it! She had just been looking at Tim... on all fours... being so eager to get rea-

Cassie was snapped out of her trance by a sensation she was all too familiar with. She moved her hands from her face instantly, looking down in disbelief. Almost wishing she was wrong. But she wasn't. Down below her, at the very end of her flagpole of a cock was her swollen head. And Tim's lips stretched around most of it!

Fuck she was much bigger than Tim thought. He couldn't even get the head fully past his lips, and he was stretching his mouth as much as he could, to the point it was starting to hurt. Before him, he could see the impossible distance that Cassie's cock made between his head and her body. Without thinking, he turned his gaze up, only to meet Cassie's. The look of shock on her face didn't last, as the startle of seeing her watching him made Tim raise his tongue up, licking the underside of her dick. Immediately, Cassie's eyes closed. She bit her lip quickly, but not before a low moan escaped. At the same time, Tim felt something splatter on his tongue: it was gooey and sticky, but surprisingly sweet, almost pineapple-y. Pre-cum.