Getting Ready 2

It was the perfect day.

Sun was shining, birds were singing, and the mailman was on his way to deliver packages in his neighborhood without a care in the world.

Whistling a happy tune, he inserted various packages inside various mailboxes as he went down the street, one by one in meticulous order.

As he finally reached the last house here, he remembered the last time he delivered a package to this location, where he was nearly scared out of his wits by a young girl somehow hiding her voluptuous body behind the skinny mailbox.

Learning from experience, he took extra caution to walk behind the mailbox just to make sure he wasn’t in for a scare like last time.

After making sure that the coast was clear, he gave a relieved sigh and went to open the mailbox.

"Hi, Mailman!"

"GOD DAMN, FUCK!"

The mailman nearly jumped about two stories high, startled by the blonde girl waiting for him from behind.

Cherry gave an oblivious smile as the mailman stared at her like she was a psycho for suddenly appearing out of nowhere, as she asked, "Got anything for Cherry Kulkin?"

The poor man took a moment to calm his heart nearly about to burst out of his chest, as he warily gave her the package in his bag. From the way he acted, you'd almost think he was getting robbed.

She had an excited gleam in her eye as she held the package in her hands, before rushing inside her house with a quick, "Thanks! Stay safe out there!"

"Stay safe, my ass. Thought I was gonna die for a second there..." The mailman sighed with a disgruntled tone.

That definitely was not a fun way to start his day.

Shaking nerves off, the mailman proceeded to continue on his route, feeling like he somehow aged five years ahead before everyone else did.

Opening the package in her room, she meticulously counted each medal token and made absolutely sure that she got the entire collection without missing anything else.

After what happened last time, Cherry learned her lesson in trying to jump the gun for the best deal possible, and now instead properly did her research before moving to buy anything.

Not wanting to embarrass herself in front of her little brother like before, this time she came prepared. For the past three days, in order to fully understand more about the toy Ross liked and how it was supposed to work, she spent the time binge-watching the entire series of Kamen Rider OOO without taking a single break. This included all forty-eight episodes, the four movies starring the titular character, and the other three crossover movies that aren't even canon to his main storyline.

She was so dedicated to watching the entire thing as soon as possible, her Dad had found her passed out on the living room couch while she was on a streak, continuously watching for sixteen hours.

It was tiring, for sure. She had to call her workplace and use up one of her vacation days just to be able to keep up.

But it was worth it, because she was now finally knowledgable enough to intrinsically understand the series that her little brother likes to a T, which includes all the knowledge that comes with how the toys are supposed to work.

No more embarrassing moments like the night of their last date together. She wouldn't be surprised if she somehow knew more about the season than Ross himself.

Using this knowledge, she was finally able to buy the correct bundles and accessories that were supposed to have come with the original toy belt in the first place. Of course, it costed her a pretty penny just to be able to afford getting every single medal token for every possible transformation combo, especially the popular purple dinosaur medals. She might need to go on a diet for the next week or so, because of those specifically...

But it was definitely going to be worth it if she was going to see her little brother's awe-struck reaction to how hard she's worked just to get it for him!

She laid the entire collection down in perfect color-coded order inside a large display case, before standing up and wiping the sweat off her brow as she admired her hard work.

Once he gets here, the first thing Ross was going to see will be the entire collection on display, all just for him. He'll be sooo impressed with her, it'll be enough to make up for her mistakes for sure!

She had a brief thought of maybe also laying on top the display case completely naked as an added bonus, before shaking her head with a shameless blush.

"Down girl, you'll get your treat soon..." Cherry whispered excitedly to herself, stopping a hand from unconsciously going down to her crotch. "Stay unsoiled for him until then..."

This second date was going to be even better than the first, she just knows it!

He stared at his phone screen like a mindless zombie, the Parallel Lovers app waiting for him to make his move.

Was he going to be ready for this, he wondered? What exactly was going to happen between him and Cherry during their next date today?

Even though it's been a decent while since the last date happened, the whole entire thing was still stuck on his mind even now. He never stopped thinking about what they did.

Will he still be comfortable around her? Will things get even more awkward from here-on out?

Ross went to check on his text messages again to reread the last few texts he had gotten from Cherry in the other dimension.

Courtesy of Parallel Lovers, they were kind enough to act as a messenger for them both, sending their texts between dimensions free of charge.

Talking to her through text seemed decent enough, although neither of them ever acknowledged what happened that night of their first date. When they talked about plans for the second date, she seemed excited enough. If he didn't already know better, he would have almost been convinced that blowjob she gave him never really happened.

She was going to have the whole house to herself today, and they'll be spending the entire date at her house to watch some movies in her room or something. Dad in the other dimension had a conference to attend out of town, so he won't be back until after the weekends. Surprisingly, the other Ross was apparently going to go attend a soccer match against another high school and won't be back until night time.

"I play soccer in the other dimension?" Ross muttered confusedly, "I don't even like sports..."

The difference between their two reality wasn't the main concern, however. The real concern comes from spending the entire date over at her house with the two of them alone in her room. He wasn't sure how to handle the idea, since the last time they were alone in her room, he cummed down her throat in a fit of lustful passion.

Were things going to be weird around them, or will the date be normal and go exactly the same as the first? He had no idea, and that was what worried him.

Even though the blowjob was probably the best thing to have ever happened to him, he honestly didn't want their relationship to change so drastically already. Even if Cherry was just an alternate version of his sister, he still considered her to be his sister...

With that said though, when he thought about what he wanted between the two of them... the answer always seemed to come up blank.

Hopefully, by the time the second date starts, he'll snap out of his weird funk and just have fun with her like they did the last time.

He wasn't sure whether he should bring up what happened between them to her so that they could try and talk about it though... On the one hand, it'll be nice to get some closure to see what her thoughts about it were. On the other hand, it was going to be a weird-as-hell topic and probably make the whole date awkward between the two of them.

Sigh... things can't ever be not complicated, can they?

Chances are, he was probably overthinking it anyway.

"Movies, check!" Cherry listed off in her checklist, roaming around the house to make sure everything was according to plan. "Fridge containing Ross's favorite snacks and drinks (sans ****), check! Airconditioner, check! A warm blanket, check! TV in both living room and bedroom functional, check!"

Opening the door to her bedroom, she double-checked her medal token collection hiding under her bed, "Special gift for Ross, check!"

Making sure she was absolutely alone in the house, she cautiously rotated her head around the vicinity like a night owl before opening up her cabinet drawer.

"Condoms and lube, check!" Cherry smirked happily.

Finally, she went up to the mirror to admire her fashion style for the day. A strapless and easy to remove white shirt baring her midriff, and a cute short black skirt to go with it. A bit floozy than what she regularly wears and not something she'd want to be caught dead wearing by anyone outside, but perfect for what she had in plan for tonight.

Cherry pulled down her shirt and skirt to reveal the new matching set of silk lingerie she got the day before, before redressing herself and signing her checklist, "Battle-armor, check!"

Everything was prepared and ready for the date. If things play out right, things will lead up to a very very wonderful ending tonight.

First, once he arrives, she'll take things slow. Let him get comfortable, watch a couple movies with him, eat dinner together, make it so that things between them are less awkward and weird as possible. No need to go on the offensive and try to flirt him up, since that might intimidate him and inadvertently push him away. She was going to let the cute outfit to do all of that, while she pretended to be the same responsible and happy big sister that she's always been. Let him sneak a peek here and there, maybe bend over a few times if she had to, but basically just make him riled up on his own without needing to be overtly obvious.

Then, when the sky goes dark and day becomes night, she'll invite him inside her room and hand him her gift. By that point, he'll be so happy and horny, it should only take one smoldering look to bring down his defense before beckoning him to join her in her bed. Whatever happens next will be out of her control as nature takes its course.

Her face became flushed as she bit down her pen, fantasizing what was about to come later tonight. For a second time, she willed herself not to touch anything below her waist, wanting to keep herself ready by the time she finally reaches that point. The build-up was excruciating, but the payoff will definitely be worth it if all goes to plan.

Suddenly, the sound of a door opening snapped her out of her imagination.

She turned in surprise, wondering if Ross was already here. Pulling out her phone to check the time, she was a bit confused to see that it was still a bit early for him to arrive.

Putting her checklist away, she stepped outside the living room to check who entered the door, only to freeze when she saw Ross rummaging around in the kitchen.

At first, she got a bit excited to see her little brother already here, but after a second of thinking about it, she realized that there was a chance that this might actually just be the other Ross instead, coming home early for some reason.

Cautiously stepping into the kitchen, she called out, "Ross? Is that you?"

When Ross turned around to give her a bored look, she instantly knew that it wasn't the Ross she was looking forward to seeing today. She'd recognize that same bored apathetic look on her little brother anywhere. It was Ross Kulkin, not Ross Culkin.

"The hell kind of outfit are you wearing? You look like a schoolgirl ready to solicit her teacher for better grades in a porno set." Ross asked bluntly, giving her a weird look before going back to scrummaging in the fridge.

Giving a sigh, Cherry said tiredly, "I'm getting ready for my date to arrive. That's what the outfit is for."

"Oh, so you actually managed to snag a guy after all." Ross said in a bored tone, "When you said you were going on a date last time you were out, I thought you meant you were going out with a bunch of your girl friends."

"Weren't you supposed to be out for a soccer match or something? What are you doing back home so soon?" Cherry asked as she curled her arms up disappointedly.

"Relax, Cher. I didn't come home with plans to crash your date." Ross reassured, before pulling out a pack of energy drinks from the fridge, "If anything, I'm actually happy you're spending time with a different guy other than me for once. The more time you're with your new boyfriend, the less time you need to spend with me."

Cherry looked away awkwardly, knowing that it would be pointless to correct him on who she was actually spending time with...

"I'm just here to pick up some fuel for the match ahead for me and the team." Ross gestured to the energy drinks, "Spend as much time as you want with your guy friend and don't worry about waiting up for me. After the match, I'll be celebrating the winning-slash-losing party over at a friend's house and won't be back until tomorrow morning. So do whatever you want."

"You're going to be gone that long?" Cherry asked with concern, "Are you sure you'll be all right? I can whip something up for you to eat before you have to go-"

"Stop." Ross bluntly stated, making Cherry shut her lips tight, "Worry more about your date. I'm gonna be fine, this isn't the first time I've been out of the house by myself before. I can handle things on my own."

...

"Okay... I trust you, then." Cherry relented with a depressed frown.

Ross raised an eyebrow at that, seeming pleasantly surprised at the response, "Huh, that's a first. I usually have to fight tooth and nail just to get you off my back. This new boyfriend of yours is a blessing in disguise." Making his way to the front door, he turned around and waved, "Have fun with your date. I'm out for the night. See ya."

With that, he left the house without another word.

...

Cherry gave a depressed sigh as she sat down on the kitchen dining table in order to give herself a moment.

Honestly, she hated that so much about her relationship with her little brother. She hated how he never seems to need her anymore for anything at all. Not even to help make him food just to prepare for his night over at his friend's house even.

Would it kill him to at least rely on her for something as simple as that?

It made her feel useless as an older sister, not to be able to do anything for him. And without that, there'd be no way to stay close to him anymore if she couldn't be at least that to him.

At this point, he might just leave her behind someday and live his own life without her in it...

...

No, there's no point in thinking about it right now.

She had an important special date tonight with a different little brother. Even if the other Ross doesn't want to be around her, there's a Ross out there who does and will appreciate everything she's doing for him.

This is the Ross whose face will light up the moment he sees her in her sexy outfit, who'll love her once he sees the trouble she went through to get his present, and the Ross who won't be able to keep his hands off her body once the night is over.

As long as she at least has one little brother to rely on her, she'll be fine. Everything will be fine.

As long as she had one little brother to please, everything will be fine...

"You look like you're about to pass out," Cherry commented.

Was he? He did feel a little bit flushed, not gonna lie.

Christ, this second date was taking a toll on him worse than he thought. Seriously, what is with him?

As Ross stood there in front of the front door, nervously flexing his fingers and working up some fortitude for the coming date, Cherry Culkin was sitting bored in her sofa seat, watching her little brother as she flipped through the channels on the TV.

Ross turned to look at her, seeing that she decided to wear some kind of floozy outfit for the day. Strapless black shirt with a v-cut showing her cleavage, with a short white skirt to go with it. He didn't bother to ask why she was wearing something like that at home, knowing that it was just her usual fashion sense that came naturally to her. If it didn't make her look like a schoolgirl trying to solicit a teacher to give her better grades in a porn video, it might as well not even exist for her.

"You know, it's gross when you stare at my body," Cherry stated without a hint of shame or embarrassment, much to Ross's chagrin.

"Oh shut up, you're the one who dressed up as a slut!" Ross grunted back defensively. "Wear decent clothing for once!"

Cherry shrugged it off, not even taking it as an insult. Resuming the topic, Cherry asked, "So what's got you so freaked out?"

"I'm not freaked out, just... Well..." Ross trailed off, before scratching his neck awkwardly, "I'm just going on my second date with this girl and I don't know how to approach her over something that happened between us last time we saw each other. That's all."

This is so weird, having to talk to his older sister about his feelings before he went out on a date with... well, his older sister...

"Wait, so you're actually dating a real girl after all?" Cherry blinked in surprise, "Huh... I thought for sure you were just making that up in order to look cool."

"I'm not that pathetic. Sheesh." Ross grumbled.

"Anyways, knowing you, you probably did something stupid like sexually harass her or something." She waved off, "If this girl is still crazy enough to agree to a second date, then you're good to go. No sense worrying about it."

"Will you ever have a higher opinion of me one of these days?" Ross muttered bitterly at his sister's casual approach in belittling him.

"All I'm saying, whatever happened between the two of you last time, she obviously doesn't care if you're already preparing on a second date." Cherry explained nonchalantly, "Worst comes to worst, you screw up this date too and she decides to dump you tonight. No big deal."

"If this is your attempt to help calm me down, it's not working."

"What?" Cherry turned to him in genuine confusion, "I wasn't trying to help calm you down. I was just stating facts."

"Gee, thanks." Ross deadpanned.

Turning back to the TV, Cherry said in a bored tone, "If you do get dumped tonight, you can buy me some ice cream to help make you feel better."

"Why in the world would buying you ice cream make me feel better?"

"Uh, because I would share some of it with you? Duh?" Cherry stated as if it was completely obvious.

"If that's the case, I can just get the ice cream for myself then."

"But then how would I get any ice cream?" Cherry asked in complete seriousness.

...

Ross gave a sigh as he shook his head.

For some reason, despite the annoying talk with her, he did feel slightly better since it put his mind off of the date for just a brief moment.

Maybe she's right... If Cherry from the other dimension agreed on the second date, it was because she didn't mind too much of what happened that night between them. Maybe things will work out just fine and he was seriously just overthinking it.

If the conversations about their last date come up tonight, then it'll come up naturally while they're having fun with each other. He didn't need to make a big deal out of it.

He definitely wasn't going to thank his sister for helping him calm down though. Knowing her, it was just an unintended side effect, not the actual goal in mind.

"Well, I'm off to go on my date now. Tell Mom that I'll probably be late tonight." Ross said as he prepared to leave.

"Do that yourself, I'm busy." Cherry mumbled distractedly, her attention glued to the TV screen already.

"Fine, fine..." Ross sighed.

"Also, if she doesn't break up with you after tonight, then someone is probably paying her to pretend to be your girlfriend. Just a heads up."

"Oh shut up!"

With that, he walked out the front door and angrily slammed it shut, much to Cherry's amusement.

God, what fucking bitch she was...

Whatever, it's fine.

At the very least, the Cherry he was about to go out and see will be loads better than the one at home. No sense worrying about anything else.

As the two duos from separate dimensions hold on tightly to their phones, their hearts raced together in unison. Ross, with wanting to make sure that this date doesn't end up awkwardly, and Cherry, with wanting to make sure this ends with her little brother's dick inside either of her three holes.