Rooftop Relationships

You bent over and put your hands on your knees, breathing heavily from running all the way up to the rooftops. Tiffany, however, doesn't look any worse for wear.

She leaned her head down to your level and asked, "You alright?"

"Yeah... I just... I'm not good with running up stairs..." You gasped, before clearing your throat and getting your bearings. "Right. I think I'm okay for now."

Tiffany smiled at you, before gesturing you to sit down next to her against a wall.

You nervously do so, wondering if she was gonna try to pull any more moves on you. You admit, today was a pretty weird day already. The fact that Tiffany Brian, most popular girl in school, cheerleader captain, and your past middle school crush, had chosen you out of all people to be in her...

Be in her... Uh...

Well, honestly, you have no idea what's going on. Everything happened to fast for you to comprehend. You think you're her new boyfriend now?

How in the hell did you even manage that?

And also another thing that's been bugging you...

How does she know your name? You were under the assumption that she had forgotten who you were, or never even knew you existed. It's almost shocking to you that she even recognized you.

After moment of silence has passed, Tiffany turned to you with an embarassed look, "I am so sorry about this, John! I didn't mean to get you roped into my mess!"

"You're s-sorry?" You stuttered, confused by her sudden shift in attitude.

"I got too hot headed and didn't think clearly. I just wanted to piss Zeke off so that he'd get upset. I didn't mean to suddenly get you involved..."

"It's fine, I think... I mean..." You awkwardly scratched your head, "Well, I guess I got caught off guard with that sudden kiss and the fact you declared me as your new boyfriend after breaking up with Zeke."

She laughed with an embarassed blush, "Right... Again, really sorry about that, John! If it means anything, I didn't actually expect you to be a good kisser. Sooo, there's that?" She complimented.

"Uh... Thanks... You're pretty good too..." You complimented back.

She chuckled, "Man... First time we met up like this in a while, and it's only after something as stupid as this..."

Uh... What? What did she mean by that, you wondered...?

Well, since this was the rare opportunity to talk to Tiffany Brian herself, you might as well take this time to talk with her while you still had the chance.

"Tiffany... I gotta ask, how did you know who I am?" You started asking, "Do you know me or something?"

Was she like the other students? The ones that you've been hanging around with during lunch, where they all seemed to know you and your name. If so, what exactly was going on here? How was your name getting out? You're kind of grateful for the sudden attention, but you're also curious why it got started in the first place...

She answers in a way you didn't quite expect.

"What do you mean? Of course I know you!" She told you as if it was the most obvious thing in the world, "You're John Doe. We used to go to middle school together."

"Oh." You blinked, "Heh, that's... Wow, okay. I didn't realize you still remembered me. I mean, it's kind of a surprise since you and I never really even hung out during middle school."

Tiffany has been acting completely different than how she normally acts with others. Instead of being the pompous popular girl like you thought she is, she actually acted like a normal girl. Almost like a friend...

Maybe you've had the wrong impression of her this whole time?

"We..." She looked at you strangely, "We never hung out in middle school?"

Hm? What's up with that look?

"J... John?" She slowly asked, "How much do you remember about me since we've first met?"

Since you've first met?

Since you've first met... Hm...

"Well... Uh... I don't think we technically had a first meeting at all. I'm pretty sure we just sort of saw each other in the school cafeteria. The first day I saw you was when you... I think you transferred from another school mid-semester or something, right?" You asked her.

She just stared at you like you lost your mind.

"Uh... Okay... Right..." You coughed, awkwardly continuing, "So anyway, I would see you around lunch. But I don't think we've ever said hi to each other or talked. Like, ever." You looked away for a bit, "Since I'm now apparently you're new **** boyfriend for Zeke, I guess it's fine if I admit it now. I used to have a small crush on you back in middle school, actually. You were cute, but I didn't have the balls to really speak up or say anything. Then I found out you were dating Zeke, and... well, that ship sunk really quick."

Tiffany stared at every inch of your face, trying to look for something.

"That's seriously all you remember about me? That I showed up out of nowhere mid-semester? Nothing else?" She asked.

"I... I don't... know exactly what to say here..." You awkwardly rubbed your neck.

"You seriously don't rem-..." She suddenly got quiet, thinking to herself.

You're lost again. Was there something you're missing here? You kind of feel like an asshole right now.

She shook her head and smiled sadly to herself, "No... Maybe this is for the best. Erase it all and start over fresh..."

Excusez moi?

Then, like a flip of a switch, Tiffany started acting differently. She laid back against the wall with a carefree smile, and with a smug tone, she explained, "Alright, listen up buddy. The next few days are going to be the luckiest days you've ever had in your life, because you'll be spending it together with me. Zeke and I are having a falling out. So I need someone who's stud enough to replace him as my boyfriend, and make him absolutely jealous until he's practically begging me to take him back."

What the hell is with this shift in attitude? She's like a completely different person now.

"Thankfully for you, I've decided that you're the perfect guy for the job." She condescendingly poked your forehead, "So here's the dealio. This won't be a permanent relationship. I just wanna make it clear right now. As much as I'm angry at Zeke, I'm just doing this to punish him so that he'll be more considerate of my feelings next time. So, all I need is for you to act like my perfect boyfriend for as long as necessary until Zeke learns his lesson."

You furrowed your brows, not taking kindly to the way she's treating you like some servant. "And why the hell should I go along with that?"

She pulled her finger away, confused at your angry tone. She coughed and recovered her composure quickly, before smiling mischievously, "Now, now... I'm not asking you to do this for free. There's a reward waiting for you if you do this for me... When Zeke eventually wants me back, I'll be breaking up with you behind the gym during after school hours." She held her hand up in an O shape, and started jacking off the air. "But not before rewarding you with a nice, long, hot 'Goodbye Breakup' quickie. And if you do an exceptionally well done job, I'll throw in a bonus of doing it completely topless too. So what do you say?"

You silently stared at her with an indignant and angry glare.

Tiffany noticed your look, and slowly grew nervous. But she doesn't say anything else.

Welp, that's your cue to leave.

You wordlessly got up and walked back down the stairs.

"W-wait! Where are you going?" Tiffany ran after you, "What, did I not offer enough? Did you want something more than-"

You turned around and held a hand to her lip, "Okay, so let me stop you right there. If you want an answer to that extremely stupid deal, the answer is no. No, I do not want to help you punish Zeke by making him jealous. I especially don't want to do it because you think you can just pay me off with a topless handjob, as if I'm just some mindless pervert."

"B-B-But I thought you said you had a crush on me since middle school?" She stammered in bewilderment. "Wouldn't you want to-"

"Had. Keyword, I had a crush on you back in middle school." You corrected her, "I stopped and moved on when I found out you were dating Zeke. Even if I did still have a crush on you, the fact that I would only be your pretend boyfriend DOESN'T make this deal sound any more appealing. So how about, you take this deal, shove it up your ass, and go find some other boytoy to do it. I'm sure there's tons of horny bastards around here that's more than willing to let you manipulate them for a chance to get their dongs touched."

You start to move again, before Tiffany latched on to your arm and refused to let go.

"No! Please! Just please wait! You don't understand!" She pleaded, "You're the only guy around here that I can trust! All my other guy friends are already in their own relationships, and I don't know anyone else well enough to trust them! Plus, I already went ahead and announced to the whole school that I would be dating you, so I can't go around and get someone else, otherwise it'd make me look stupid!"

"I don't see how any of that is my problem! You should have thought this through before suddenly kissing me out of the blue!" You began to rub your head frustratingly, "I don't fucking get you at all! You're a complete mystery to me! One moment, you're acting normal and friendly towards me, then the next minute, you're suddenly acting like a condescending bitch!"

Tiffany looked up to you in shock, slowly releasing your hand. Taking your hand away from her, she flopped her arms down and slowly asked, "I... I was acting like a bitch?"

"Yes, a real condescending and arrogant one! I also don't appreciate the fact that you think you can just pay me with sexual favors and that I'll just do whatever you want without question. That's more demeaning than if you had just- just fucking ASKED me to be your boyfriend and then suddenly break up with me later without telling."

Tiffany looked down at her feet with a remorseful expression, tightly hugging one arm. "I... I see... I'm sorry... I didn't mean to come across like that... I thought I was... I dunno, I thought I was acting sexy and cool in front of you."

You were almost about to scoff and leave her again... But you paused, looking her over once more.

She does seem to be feeling genuinely guilty over how she acted.

Man, it's so hard to understand her. You pegged her as one of those annoying pompous girls who would flaunt their fame and good looks towards everyone, but then you thought you just misunderstood her. Then she went back to being bitch, and you felt like an idiot for even thinking otherwise.

Now she's telling you that she thought she was just acting cool, and now you have no idea what to make of her.

Does she seriously not know how rude her behavior was?

Ugh, that damn pathethic look on her face was eating you away from inside...

You sighed.

...

GOD DAMN IT-

Fuck, you are going to regret doing this, aren't you?

"You and I have some very different definitions on what being cool means." You rubbed your head irritantly.

"I'm... sorry..." She apologized again.

"Whatever..." You calmed down, before starting, "Look, you just want me to pretend to be your boyfriend for the time being, right?"

She perked up and looked at you with a hopeful expression, "Y... You mean-"

"I'm doing this just to be nice, okay?" You assured her, "But I'm only gonna do this on two conditions."

"Anything!" She said in a **** tone, clasping her hands together to beg, "Anything you want!"

"One, don't ever act like that towards me ever again." You told her sternly. "I don't worship you, I'm not a mindless fan, I don't care that you're the captain of the cheerleaders. So don't act like I do. Instead, just act like you did earlier today! Be friendly and polite! I like you better that way."

"Oh... Okay, I promise to do that." She nodded.

"Secondly, please don't ever drag me into these sort of shenanigans again..." You sighed, "I don't know if you have any idea how popular you are, but because of what happened in the cafeteria, I'm pretty sure everyone in school will be talking about this. 'Long Time Highschool Sweethearts Zeke and Tiffany Sudden Break Up, Tiffany Dates Random Guy Instead!' That's gonna be the rumor spreading around. It's going to be completely awkward for me to come to school in the future now because everyone will start wanting to know who I am."

"R-Right... I'm sorry again, for that." She said sheepishly.

"As long as you keep those two promises, I'll help you out until Zeke learns his lesson. We cool?" You finished, sticking your hand out for a respectable handshake.

Tiffany looked down at your hand, but then looked up to you with a grateful smile. She suddenly lunged at you and wrapped her arms around your neck, "Thank you! Thank you thank you thank you! I promise I won't make you hate me! You just saved my relationship!"

Caught off guard by this, you awkwardly hugged her back.

She eventually let's go, but then asks, "But wait, what about the handjob I offered you earlier?"

You blushed at the reminder, but said, "What do you mean? What about it?"

"Like, do you still want it? I was actually serious when I offered it as a reward, not as a way to tease you or anything."

"W-Wait, you mean, right now?!"

She giggled, "No, silly! I didn't mean right now. I meant later, when all this is over! Offer is still on the table if you wanna grab it."

Oh jeez...

You place a hand around your heart and calmed down, "Don't get me excited like that..."

This girl is just shameless when it comes to sex, isn't she? Not even an ounce of embarassment showed up on her face when she mentioned it. Like it was the most natural and casual thing in the world to offer someone a handjob.

She checked her phone real quick, and then said, "Actually, we still have a few minutes before lunch period is over. If you want, I can give you a quickie right now."

...

Wait, what?

"A-Are you serious right now?!" You stammered.

"Sure. It can be an apology for... you know... how I was acting earlier, and making you go through all this trouble for me." She rubbed her neck in guilt, "An apology handjob."

This girl is crazy.

That, or she's just so naturally a slut, giving a handjob to a guy she barely knows doesn't even bother her.

It makes you wonder what her priorities were like if she got so upset at her own boyfriend for secretly recording her.

"I promise I'm really good. Like, Zeke usually has really high endurance from playing soccer all day, but I can easily make him cum in less than five minutes with just my hands." She reassured you, waggling her fingers as emphasis.

The thought of her skill gave your dick new life as it swells in your pants.

Fuck, you are seriously a perverted freak.

No, no, no, don't be tempted. Come on man, take the moral high ground. If you accept it now, it just defeats the point you were trying to make.

...

...

She waggled her fingers again.

FUCK, you hate your teenage hormones.

"F...Fine..." You muttered with a guilty blush.

She giggled, before leading you back to where you two sat and got down on her knees.

The thought of Bella crosses your mind, and you curse yourself for betraying her like this.

AAAAGH, you swear you were gonna make it up to her by furiously eating her out constantly later after school!

Please forgive this pathetically horny fool, Bella!