Tiffany and Shelly meet each other for the first time. Ever. In history.

"Soooo..." Shelly started off with a playful smile, "Tell me about her."

You raised an eyebrow, "Who?"

"Tiffany Brian, obviously!" Shelly exclaimed, stopping at a red light and turning to you, "I never got the chance to ask you how you managed to convince this girl to take your v-card. I mean, seriously, it hasn't been that long ago since you and I just started our sexy brother-sister bonding. Then all of a sudden, you not only got a new girlfriend just a few days ago, but also managed to have sex with her too? Clearly, me sucking your cock has given you a huge confidence booster."

"It's not like that." You sighed tiredly, "My relationship with Tiffany is more complicated than what you're assuming."

"Pfft, I mean, yeah. I got that already." She chuckled, "Unless this girl has had her eye on you for a long while now, there's no way she would be so quick to the boning phase unless she's a total slut."

You felt an angry tick in the back of your mind, feeling the need to warn Shelly, "Please don't call her that."

Your tone must have been rougher than you meant it to, because Shelly gave you a knowing smirk, "Oh? Ooohh~? Did you get offended on her behalf because I said a bad word? I didn't realize you two were so close already to become her white knight."

You were about to rebuke her, before slowly realizing that she kinda had a point there.

Despite it all, you still didn't really know Tiffany that well. You’ve only gotten the chance to know her for like, what, a couple days now? And this was only just literally a day after you went in your date with Bella.

Frankly, you’ve only now just realized how extremely fast you’ve been getting into relationships with various women...

And yet it doesn’t ever feel like that when you’re actually with them... For some reason, when you actually sit down to talk with them, whether it’s Tiffany or Bella, you feel like you’ve gotten to know them for much longer than you actually spent time with...

It’s a weird feeling to have...

...

No, what’s more weird here is the fact that you’re realizing that you’re starting to get more attached to Tiffany despite the fact that your relationship together isn’t even real to begin with. She’s not your actual girlfriend, she’s just using you to try to get Zeke jealous as punishment for him for being a prick of a boyfriend.

Yet you still couldn't help but conveniently forget that sometimes...

How to explain this relationship to your sister...?

“Well, whatever kind of relationship you two have, you clearly need more time to sort things out.” Shelly chuckled, shifting her car forward as the light became green. “Don’t worry too much about it, I won’t pry if you’re not ready to explain it yourself.”

You gave a quick glance at your sister in your seat.

Well, Shelly has already made it clear that she wasn’t going to be jealous of this new relationship you had with Tiffany, even since yesterday. For some reason, all the girls entwined within your romantic tree seemed completely fine with letting you get away with dating other girls...

Bella keeps saying that she doesn’t mind and even seems almost annoyed at the fact that you keep apologizing to her about it.

Shelly seems almost completely supportive about it in every single way, almost as if she’s proud of you being able to bang girls other than her.

Tiffany-

Aw crap, Tiffany had no idea that you were in a relationship with other girls, does she? Obviously due to the fact that this conversation never came up to begin with...

Does it matter though? I mean, you and Tiffany aren’t even actually a real romantic couple anyway... Like mentioned earlier, this was all just a ploy to get back at Zeke...

...

Why do you keep forgetting that?

“I guess on the topic of relationships...” Shelly suddenly started off awkwardly, her tone shifting to a less playful and more serious voice.

You brought yourself out of your thoughts, “What’s up?”

“Erm... so, uh... What happened this morning was kind of a doozy, amirite?” Your older sister couldn’t help but give an awkward chuckle, “I think you kind of... bared your honest feelings at me near the end... Gonna be honest with you, I wasn’t expecting that to happen...”

Remembering what happened this morning with Shelly, you felt yourself blush. You did say something embarrassing to her during that whole fiasco, didn’t you? Right before you kissed her.

Fuck, and now a whole new problem has just entered in the situation. Your newfound feelings for your sister...

“Right, sorry about that... I guess I just...” you stated slowly, trying to get your thoughts in order, “When I realized that I might not ever see you again, I guess I just felt like I had to... you know...”

Despite trailing off, Shelly nodded along, “Right, right. I get you. I get it.”

Another stop light pauses you both in your track.

An awkward silence filled the air.

You both turned to each other, not knowing what else to say next.

After a while, you asked, “Does this change our relationship? From before?”

Shelly awkwardly glanced away, “D-Does it need to change? It can’t be categorized as the same thing as it always been? Just me and you fooling around for fun?”

“After what happened this morning? It really can’t, no...” you shook your head, “I don’t think I can fool around with you and only think that it’s just for fun anymore...”

“Well...” Shelly thought carefully about what to say next, “Huh... no, I guess not then... I kinda feel like I’m on the same boat...” After a while, she suddenly offered, “If we’re more serious than fuckbuddies now, then maybe... I’m your girlfriend then?”

“Girlfriend...?” You repeated incredulously to yourself, “Even though I already have...” two? You trailed off before you could finish.

“A secret second girlfriend then?” She casually offered, “A side chick? Sister girlfriend? Secret mistress? Emergency booty call?”

“You’re kinda making this relationship feel even weirder than it should be.” You deadpanned.

“Kinda gone past the weird threshold a long time ago, little brother. Like, the moment I started plucking your dick in my mouth for the first time long ago.” She giggled.

That... is a good point she made there...

You two continued thinking hard about your relationship together as Shelly drove you to school.

---

When you finally saw the front doors of your school as Shelly pulled you up, the first thought you had to yourself was-

Shit, why does it feel like it’s been years since I’ve been here?

You knew why, though. You just wanted to ask to be a prick. A deep deep frustration with a certain author from the internet came to mind, as you can easily imagine him shirking his responsibilities to play Dragon Quest XI these past few months. Fucking asshole.

“So, we’re here.” Shelly brought you out of your thoughts as she parked her car.

“R-Right...” You stuttered.

Despite yourself, you didn’t leave the car yet. A hanging topic was still leering over the both of you, and you didn’t feel comfortable enough to leave things like they were now without putting this to rest.

Shelly stared at the steering wheel in her hand, looking deep in thought just as much as you do. It seemed she was taking this seriously just as much as you are, which was a change in pace compared to how she usually acts.

This whole thing was really weighing on her mind, wasn’t it? Enough to make her act more serious and less like playful teasing sister that she usually was.

Maybe... this relationship with her was a mistake? On top of what you were already going through with Bella and Tiffany, having this right on top of it would just spell trouble in the future.

Not only that, but the close call you had yesterday with your mom catching you in the act should really act as a wake up call that your actions will have consequences...

Maybe it would be better if you and Shelly decided to just... stop this whole thing before it got out of hand. Go back to how you two usually were...

Go back to... just being normal siblings with her...

“Let’s cross the line together.”

The face she made. The warmth of her body. All the memories we shared...

Do I really have to forget all of that?

“I know that face you’re making.”

You blinked, before turning to your sister.

She had a casual yet annoyed look on her face as she leaned on her arm, “You were making that one face that says that you’re about to take all the responsibility yourself and planning to do something serious even though you really don’t want to.”

...

“I have face like that?” You asked perplexingly.

“Every time you’re about to do something serious, yeah.” She grumbled, “It always pisses me off whenever I see it back when we were kids. You always act way older than you should be, and make all the big choices yourself, like you’re some sort of messiah or something. Would it kill you to rely on your big sister and act like a selfish kid for once?”

Apparently, this is something you do. How strange to establish this as a fact now all of a sudden.

“C’mon, tell me what you were thinking about before deciding on something yourself. This is supposed to be our relationship we’re trying to figure out here, my opinion should have more weight than snails.” Shelly demanded.

You awkwardly scratched your neck, realizing that you almost unintentionally left your sister out of the conversation.

“I was just thinking... that...” you started off steadily, before pausing in thought.

You looked at Shelly again as she patiently waited for you to get your thoughts in order.

“Do you think we should stop and go back to how we used to be? Before this relationship causes trouble that can’t afford to get into?” You asked seriously.

Shelly raised an eyebrow at that, almost like she wasn’t taking you seriously.

Then with a sigh, she leaned back in her chair and took a hold of your hand, “Is that what you want? Do you want us to stop this?”

You looked down awkwardly, “It... it’s not exactly what I want, but...”

Sigh... things were way too complicated for a boy your age to handle... Even though you were at the age of consent, you were nowhere near close enough to be considered an actual adult. Your brain can’t handle all of this mess weighing down on you...

You felt a hand under your chin pulling you up, seeing your sister stare at you. Then with a smile, she suddenly leaned in to give you a kiss on the lips.

You blinked a bit as she pulled away, as she started off, “To be completely honest, I don’t want to stop what we got going on here. Even though it started off as just us fooling around, I’m... kinda starting to realize that I might like you more than normal.” She brushed your cheek a bit as she gave a small blush, “Like... way more than a normal sister should feel for her brother...”

You couldn’t help but blush as well from the confession. You didn’t realize that she felt the same way. This was different from how she used to feel when she explained that she didn’t have any feelings for you the last time you asked. What changed since then?

“Besides...” she continued, “Thinking back to how we used to be? Before this whole crazy thing between us started? After everything we’ve gone through and how closer we are now, I don’t think I want to go back to that kind of life. Going through the halls, barely acknowledging each other’s existence, living everyday without even saying a word to each other? No way, that’s way too big a change to what we have now.”

“...yeah... I know what you mean...” you nodded back understandingly.

You’d never have gotten this close with your sister if this whole thing between the two of you never started. You’d rather be closer to your sister like this instead of how you used to act...

But...

“What happens if we get caught again? No way to bullshit Mom a second time... or worse, Dad catches us?” You brought up, “What do we do then?”

She smirked, “You let big sis worry about that. Out of the two of us, I’m the one that’s more suspect if something goes wrong. I guess I could make something up, like being a bit too much of a slut that I manipulated my own little brother along just for the fun of it.”

You furrowed your brows, “Thats not fair. Why do you get to shoulder all the responsibilities and consequences, but I can’t?”

“Cuz I’m older than you. Get use to it, twerp. Life’s never fair.” She chuckled teasingly.

Jeez, what kind of double standard is this?

...

“So... you’re willing to go through all that trouble... just to be with me?” You asked embarrassingly.

“I’ve dated tons of guys at this point, and I’ve never been in a successful relationship so far. Might as well take a stab at my own brother instead.” She giggled.

“Even though I’m already taken by another girl?” You muttered with a bit of guilt.

“I dunno how serious you are with this Tiffany girl, buuuut...” Shelly smiled back, “I’m willing to stick around to see what happens. Who knows, something hot might play out.”

The idea of you, Tiffany, and Shelly all touching each other in one huge bed comes to mind, and you could feel yourself flare up from the thought.

Jesus, you are a pervert...

...that brings up one last point though...

“Um... that’s got me wondering, actually...” you hesitated to ask, “you’re not dating some guy right now, are you?”

Shelly raised an eyebrow, before a playful smile pursed her lips, “Ooooh~? And why should that matter, hmmmm~?”

“C’mon, I’m serious. You know about my other relationship, it’s only right I should know if you’re in a relationship too.” You asked impatiently.

She giggled at your frustration, “For your information, I was still a single pringle before the thing between us happened. The only guy I’m fucking right now is literally just you.”

You gave a sigh of relief at that, “Oh... I see...”

“So I’m guessing that it’s totally okay to go find a guy on the side, right-“ Shelly began to casually ask, before you immediately interrupted her.

“No! Absolutely not! You can’t date anyone else!”

Shelly blinked in surprise at your rough declaration, before giving you a smug smile.

It took you a while before you realized how serious and commanding you sounded. After that, you couldn’t help but feel a bit embarrassed at the outburst.

Apparently, you had strong feelings about this...

“Sooo, you’re allowed to date other girls besides me, but I’m not allowed to so much as even look at a guy unless he’s you?” Shelly asked teasingly, poking at your blushing cheeks, “Bit of a hypocrite, don’t you think?”

“I...” You mumbled awkwardly, “I... I know... I’m... sorry... for some reason, I just... the idea made me really jealous and mad...”

Even you had to admit, it wasn’t quite fair for only you to be the only one to be openly dating other girls. But still, you couldn’t bear the thought of Bella, Tiffany, or even Shelly to go after anyone else. The idea literally hurts your heart.

“Don’t be sorry, little brother...”

You felt Shelly scotch in closer to you all of a sudden as she began to wrap her arms around your shoulder. Looking up, Shelly’s face was practically in front of you and your lips were almost touching.

“I like it when you act selfish and possessive like that~” Shelly admitted with a husky voice, her eyes staring at you half-lidded like a predator, “I promise I’ll be yours and yours alone... so don’t ever worry about that, okay?”

Shelly’s sudden forwardness took you off-guard, and you couldn’t help but gulp nervously as you felt your dick growing rock solid.

Has your sister always been like this? You’ve never been on the end of her flirtatious side like this before, so this came as a bit of a shock to see. She’s acted horny towards you before, yes, but never this... seductive.

You couldn’t get another thought in before she already smushed your lips together and invaded your mouth again. She was already on top of you as she began caressing the back of your hair and moaning into your mouth.

Your hands moved on their own, grabbing her by her hips and slowly making their way upwards as they soon happen to latch onto your big sister’s giant heaving breasts.

Slowly, she pulled her mouth away from you, leaving a trail of your fluids leaking out.

Excited by your touch, she gave a purr as she started grinding against you and **** one of your hands further into her breast, “You think we have time for a quickie session? I’m seriously riled up right now.”

Even though you were excited yourself, you had to give an annoyed, “We seriously have to do something about your sexual libido, Shelly. You are way too perverted for your own good.”

“Pfft, like brother like sister.” She argued back, her other hand already on its way down your trousers to feel up your tent, “You think I’m bad? You’re just as much as a horn dog as me, Mr. Pot calling the kettle black.”

You had to give a sigh as Shelly began forcing your hand under her shirt to feel up her bra, “What the hell am I going to do with you, Shelly?”

*Tink tink tink*

You both paused from the sound of someone tapping the glass of Shelly’s car.

Shelly stopped what she was doing to turn around, also giving you a clear view of the person who interrupted your session.

Both of your eyes nearly bugged out when you both saw a very familiar short haired blonde girl giving a shy awkward smile and she waved at the two of you from outside.

“Er... Hi, John.” Tiffany waved awkwardly.

Immediately, the two of you got off of each other and hurriedly tried to make your clothes looked presentable. Shelly did her best to clean herself up as fast as possible while looking like she just fucked up again.

You weren’t fairing well either on the other hand, so you couldn’t exactly fault her.

Both of you opened the door and left the car, looking as natural as possible almost as if your life spans weren’t cut in half again by another samurai blade from this situation.

“Tiffany!” You started off nervously, “I-I didn’t realize you were outside! I thought you were already in class or something.”

“Um, yeah...” Tiffany shuffled around awkwardly, “I decided to wait around for you so that we could discuss our plans for later after school. I just... wanted to make a few things clear so that we could be on the same page...”

...

...

...

The awkward silence that ensued was deafening, and the tension in the air was thick enough to **** you.

Dear god, someone please kill you. Like, right now. A swift chopping motion right on the neck. Head, clean off. Please.

Shelly, for some reason deciding to stick around instead of driving away from the awkward situation like you were hoping she would, nervously stuck her hand out as she awkwardly smiled, “Hi! You must be Tiffany Brian! My brother talked a lot about you! Which is who he is to me. My brother. I’m his sister. We are siblings.”

What the fuck are you doing? You looked at your sister incredulously.

Trying to save your relationship? I don’t fucking know! Shelly stared back nervously.

“What you saw back there, earlier, it was definitely not what you’re thinking.” Shelly continued on as naturally as possible, only to feel as stilted and unnatural as an undeveloped robot trying to take the Turing test. “I was just... killing a mosquito that was stuck on his face! And he was just trying to... kill a mosquito that landed in my... bra?”

...

Please kill me.

Despite the incredibly awkward situation, Tiffany brushed her hair back as she politely smiled and shook your sister’s hand.

“Hi, Shelly. You look really good, all grown up.”

Tiffany’s response caught you both off guard for different reasons. You were completely surprised by how well Tiffany was reacting to seeing you making out with someone who just admitted that she was your sister.

For Shelly’s part, she was more taken aback by the fact that Tiffany apparently knew her already.

“You... know who I am?” Shelly asked confusedly.

Tiffany paused as she looked into Shelly’s eyes, almost as if she was searching for something.

“We... have never met before today, did we?” Tiffany asked cautiously.

“I... don’t... think we did...” Shelly answered back awkwardly. “D...Did we?”

Tiffany seemed to mull the answer in her head for a bit, before declaring, “No, we didn’t!” Then, as if the past few minutes didn’t happen, Tiffany went on to greet your sister welcomingly, “Hi, it’s so nice to meet you for the first time! I’m friends with your brother, John! I hope he only ever says nice things about me!”

“Friends, huh?” Shelly couldn’t seem to make heads or tails of what to make of Tiffany, and so instead proceeded to act as normally as possible, “He told me that you two were recently dating, actually.”

Tiffany glanced over at you questioningly for a brief moment, before turning back to Shelly, “So, he told you that we were dating, and yet you guys still...” She closed her eyes for a bit, before shaking her head, “Yeah, okay. Uh, nevermind then.”

The awkward tension still lingered in the air despite the girls best efforts to act as natural as possible. You only now just noticed that Shelly and Tiffany were still shaking hands throughout all this.

Before long, you felt you had to step in and politely stop the two of them from shaking hands any longer.

Realizing how awkward things still seemed, Tiffany coughed in her hand, “Er, right. It’s so nice to see you agai-.” She blinked for a bit, then adjusted herself, “-for the first time. Ever. In my life. Since we’ve never met before.”

“Right, same here.” Shelly chuckled awkwardly.

...

...

...

SERIOUSLY, WHAT THE FUCK IS GOING ON RIGHT NOW.

Shelly, presumably having enough of this shit, awkwardly turned to you and said, “Welp! Guess it’s time for me to leave! If you need me, just call for your Big Sister!” She turned to Tiffany, “Which is what I am. Nothing more. Just a sister.”

Tiffany nodded back politely in acknowledgement.

Shelly then turned back to you.

You looked around awkwardly, before playing along, “I will remember to do that.”

“Good!” Shelly smiled, “I am going to leave now.”

With that, your sister awkwardly trudged back into her car.

You and Tiffany both watched her as Shelly robotically started her car and slowly drove off to the road, leaving both of you behind.

When you were finally left alone, Tiffany awkwardly started off, “So... uh... you two seem pretty close...”

You couldn’t exactly tell how Tiffany was feeling right now when she said that. It was pretty fucking obvious things were weird right now, but you couldn’t tell if she was upset or not.

“Uh, yeah. Me and my sister, we’re both thick as thieves. Haha.” You replied back.

“Thick as thieves, huh?” Tiffany couldn’t help but chuckle at that for some reason, smiling back at you, “Must be pretty recent then.”

“I... uh...” You had no idea how to respond to that.

So... it seems that there was a some sort of agreement between all three of you to pretend to play dumb about what just happened.

You’re not exactly comfortable with this, but it’s not like you were exactly gung-ho about the idea of acknowledging what just happened either.

So you’re kinda in a mix right now...

With a gentle smile, Tiffany curled her hair back and said, “I guess I should be happy that only I was around to see you two. Things would probably have been ruined between our plans if anyone else saw you and Shelly... um, killing mosquitos in there.”

Okay, so Tiffany obviously didn’t fall for Shelly’s attempts to trick her with those extremely piss-poor lies. Good to know. Why are you all pretending to act dumb about it then?

In the distance, you could hear a group of guys hollering like a bunch of wolves.

“Daaaaaaaaaaamn boooooooooooiiiiii-“

“Except for those guys.” Tiffany awkwardly pointed, “Seems they might know what’s up. I probably wouldn’t worry about them though, no one ever takes them seriously.”

...

“Do... do you want us to talk about this...?” You offered hesitantly. “What just happened?”

“Like... maybe?” Tiffany seemed hesitant too, “Probably... Someday, I guess. Not right now though... We’re late to class, and I was serious when I said that I wanted to talk about our plans after school.”

“Right, right, our plan to make Zeke jealous. Of course.” You nodded along awkwardly.

...

...

...

Deciding that the awkward tension in the air was started to grate on her nerves, Tiffany slapped her cheeks around a bit before hugging your arm and giving you a cute smile, “C’mon, John! I got a list of things I planned out on our schedule! We are going to be going to SO many places for our fake-date!”

You weren't nearly as quick to adapt to the situation as Tiffany was, but her sheer **** of Will inspired you to try to play along, “R-Right. Sure.”

Jesus Christ, why are all the girls in your life so weird when it comes to catching you with other girls? Seriously, you were expecting at least someone to slap you across the face for it.

Tiffany happily tugged you inside the building as she went on to explain her game plan, while you listened diligently as she explained your role in all this.