Stuck Studying With Sis

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Stuck Studying With Sis
Tagline: Imminent exams and unexpected cold weather lead to an unusual proposition between an estranged younger sister and older brother.
Notes: I suggest skipping this if you're not in the mood for a slow start. I hope you enjoy this not-so-short story with a focus on portraying character motivations through dialogue and actions.
– shykite 2021 © Originally written back in 2017
Disclaimer: All characters are over 18 and consenting adults. All of my stories are fiction based purely on my imagination, and any resemblance to real events or people are purely coincidence. This work was originally written by shykite and is not reproducible without permission from the author. If you see this story posted elsewhere please let me know.
"Open up, it's the police."
The command emanated from an oddly high-pitched gruff voice from in front of the entrance to an older, faded-brick building. The sidewalk to the doorway was partially covered with a thin layer of ice and a solid barrier of snow that had captured the footprints from a few individuals braving the cold and shuffling their feet on the slippery pavement. A muffled "crap" and the stomping of feet could be heard through a light-gray wooden door.
"One minute, officer, I'm not fully-dressed," said a slightly frantic male voice.
"You have ten seconds before we bust this door down." The unusual voice paused a bit before beginning to count down.
Right after two, the door opened to reveal a tall, disheveled young man only wearing a crumpled white shirt and forest green boxer underwear. "I'm sorry for the wait, off-" began to come out before he saw who was actually on the other side of his door and he just groaned in response. "Jane, you have to stop pulling these sort of pranks on me. You're already 19 for crying out loud!"
"But, dear brother of mine, you know you love me," said the teenage girl, drawing out the last two words as she entered the apartment. "Score's now one to zero with 'The Magnificent Jane' taking an early lead. Anyway, what you been up to today, Scotty boy?" Jane asked as she casually strolled to a beat-up couch and placed her purple backpack on its sunken cushions. She then removed her thick bright-red winter coat and fur-lined boots before returning her attention to her brother.
Scott just stared incredulously at his troublesome little sister before finally deciding it wasn't worth igniting an argument and replied, "Not much. All my classes were canceled since Thursday due to the unexpected snow. It's too cold to do anything but study for finals next week and play a few rounds of CS to relax once I'm done. You? Also, why are you here, Jane?"
"Are you sure that's all you've been doing today?" she asked with a mischievous smile.
"Yes…?" he said, hesitating with the expectation of more trouble to come.
"That doesn't agree with your story," she pointed to the unbuttoned flap of his boxers and a noticeable bulge partially visible through the gap. "So who were you masturbating to today?" she said excitedly. "Wait, I know! It's got to be that one girl you liked so much. What was her name again? Riley Re-"
"Y-You're getting a little carried away there, Jane! I wasn't doing… that, the fly — it just opened because I had to rush to the door. Besides, even if I was masturbating how would you know anything about which kind of girl I like? I've never talked to you about that sort of thing," he said angrily and somewhat confused.
"Easy, I borrowed your computer once while you were out and happened to notice the dozens of suggestions starting with 'po' that popped up when I tried to search for multi-compound polymers to prep for my Chem 1001 test. Almost all of them were bookmarks of a certain brunette. Score two to zero in favor of me," she said shooting a smug grin back at her brother's pale face.
"Jane, this isn't something we should discuss. Let's move onto another topic," he said with a hint of exasperation as he buttoned his boxers and went to his room to put on some pants to prevent future mishaps.
"You're no fun. Why shouldn't we be open about a topic as important as sex? Everyone wants to get laid but admitting we all have sexual desires is still somehow taboo in society," Jane frowned as she shared her thoughts before brightening at a related thought. "I could tell you about the guys I fantasize about if that helps you stop being such a fuddy-duddy," she said teasingly while placing her coat on a hanger inside the closet.
"You need to stop. You're my sister and this discussion is one hundred and ten percent off limits," he said while shaking his head to try and clear the unwanted thoughts from his mind. "Why are you here? You never answered," Scott said while reentering the living room. He was still pulling down a loose t-shirt over his head but at least he was fully clothed and wouldn't have to endure another round of embarrassment.
"Fine," she said dejectedly. "I want your help. You're way better than I am at Calc. My grades haven't been the best this semester and I really need to do well to get an A. Please help me study for the final? Pretty please with cherries on top?" she asked with a well-practiced puppy dog pout.
"No," came flatly from his mouth. "Before you start begging and trying to manipulate me with a date as a 'reward', the answer will stay a firm no," he said with finger-quotes around reward. "I need to focus on my own finals. Failing means I won't graduate on time or with the GPA I want, throwing all my future prospects into the dumpster for at least a year."
"But I can guarantee this date won't be as bad," she said vehemently with a knowing look in her eyes. "Chloe owes me for not telling Beca about that time she accidentally scratched her car. Plus I can tell she thinks you're kinda cute," she finished a little quieter before immediately going back to pouting.
"Not interested. Chloe's not my type anyway," he said with immediate mental warning signs starting to flare up at his unintended admission.
"Oh, so she's not a petite brunette that can pleasure dick like a world-class porn star? That's going to be hard to find for anyone, even me," she muttered just barely audible with a frown on her face. He was about to sputter a half-hearted response but there was no point in denying it any longer. Jane began to play with a strand of her hair as she thought this new problem through. "None of my friends really fit the bill if you're going to be so picky. Maybe we can trade something else?" she asked hopefully.
"What do you have to offer me?" he asked with a smug look crossing his face. "Face the facts, sis, you'd have been better off talking to someone else about extra help. You could have asked for tutoring earlier from a TA or classmate. I'm sure at least a few guys would be more than happy to help a pretty girl out," he quickly muttered the last part under his breath.
Jane had become a headstrong person ever since entering high school two years after him. Rarely asking him for any help with homework, rides to the mall, or typical teenager requests of elder siblings. Prior to that point, they had a fairly close relationship that had grown throughout their childhood. She had loved to hang out with her big brother and watch movies, play games, read books side by side, and ask questions.
When she had suddenly decided to cut their typical hangouts out of his life, he had simply shrugged and spent more time with friends and disastrous attempts at dating. The primary form of interaction between them had rapidly evolved into regular attempts to pull one over him no matter the circumstances. The only reason he'd even had a first date with Marlie was as an apology for a particularly disastrous prank that had resulted in rumors that he had gotten mono early junior year.
He lost himself in the memories of that amusingly terrible date for a minute before refocusing on his surroundings to glance over to his sister. Jane was still deep in contemplation, playing with her slightly mussed up, burnt-caramel and milk chocolate locks while fidgeting on the cheap couch. He could see a small furrow cross above her button nose as she scrunched her face in concentration. She was wearing a surprisingly thin outfit considering the poor heating inside the college dorms — just a polka-dotted v-neck shirt and grey sweatpants. He was about to comment on her outfit when she suddenly started and turned to him with glimmers of excitement sparkling in her eyes.
"I've got it; I could be your live-in maid for the weekend! You can barely cook a decent meal, your apartment is a cluttered mess, and you could use my help to focus on your own finals instead of having to fend for yourself. I'll even make your favorite cookies for dessert," she said with a wide grin.
Scott was extremely tempted in spite of his better judgment. He thought her offer over while looking for any signs of deception but didn't see any hint of imminent trouble cross her hazel eyes. He was certainly tired of eating cheap ramen and meh microwavable food so practically anything would be better sustenance. On the other hand, he could always just order out or attempt a simpler recipe, one that didn't have any complex instructions like not accidentally burning the eggs. On second thought, maybe having to share his private space with another person, let alone his troublemaker of a sister wasn't that important. His grumbling stomach definitely didn't seem to care so he made up his mind.
"Fine. But you need to follow my rules before we go through with this arrangement. No pranks, we sleep before 1 AM, and no more talking about any masturbation habits either of us may or may not have," he watched her face for any sudden twitches but her widening smile put him slightly at ease. "Capisce? You need to focus on your finals just like I do. Deal?" he asked and held out a hand.
"Deal," she said while shaking his hand in agreement. "Now let's hurry up and get started before you change your mind! Eat a snack and we can quickly drop by the grocery store a few blocks away after some work. I'm sure your fridge is missing all the ingredients necessary for an actually tasty, healthy meal," she said while pouring out the contents of her backpack.
Tutoring went pretty well, considering how the tiny amount of time the siblings had spent in peace together. Jane was surprisingly easy to teach and seemed to have a solid grasp of the fundamentals of Calculus. Her trouble arose with identifying the appropriate trigonometric identities to use when there were multiple angles of attack. They had spent the entire day working side by side over their respective textbooks with Scott occasionally going over to answer her questions before they both needed a break. Deciding to make a family recipe of Italian meatball subs with a store-bought marinara sauce for dinner, brother and sister had shared a delicious meal over a lighthearted discussion catching up about their respective classes, friends, and lives.
"So about the live-in part of this agreement. How exactly is that going to work? Why don't you just study over here and I'll drop you off at your dorms?" he asked his sister as she washed the dirty dishes while he placed them to dry and tidied up the tiny kitchen adjacent to the living room.
"We don't need to waste time commuting every day, silly!" she exclaimed exuberantly before listing off more reasons in favor of staying the night. "The weather forecast predicted a much heavier snowfall sometime this weekend, so it's likely we'll get stuck inside our rooms for hours before enough snow melts. Besides, I've got an extra outfit or two in my backpack in case of emergency but I'll need to borrow some spare clothes. An old t-shirt of yours should be fine to sleep in. I think I'll be warm enough on the couch with the spare comforter mom made you buy when you first got the apartment."
"You take my bed. I'll sleep on the couch," he said after looking the couch over.
"Are you sure?" she asked with concern. "It's pretty cold and this old couch isn't really fit for someone as tall as you to sleep on. You're practically one and a half times my height which is way too much for poor ol' Betsy."
"You named my furniture?" Scott chuckled and shook his head at her antics. "It's fine, I've slept on Betsy while blitzed before and it worked alright then. With a thick blanket and an extra layer of clothes, I'll sleep like a baby."
"What about if we double up like we used to as little kids? We'll both be comfortable that way," she said the sentence normally but there was something a little… off about her eyes. Whatever it was made Scott a little wary and fear some form of prank despite agreeing to his rules.
"Nope. It's already decided. It's almost midnight, I don't know about you but I'm exhausted so let's get to sleep soon," he said while rubbing his eyes.
"Night, Scotty." Jane approached and quickly hugged him before he could react. "Thanks for being such a great big bro," she whispered into his ear before heading to the comfort of the bedroom.
"Night, Janey." He stared at her retreating form for a few seconds before going to grab the extra comforter and some additional layers of clothing from the closet.
He shut his eyes impatiently waiting for the sandman to arrive when he heard the quiet sounds of tiptoeing passing by. Assuming his little sister just needed to get some water or something else unimportant, he rolled over and covered his head. The allure of sleep was too strong to be a busybody and he drifted into a deep sleep.
The dream he had that night was unusual. The premise was certainly familiar, though. It was a near perfect recreation of his favorite point-of-view doggy-style scene featuring a certain actress but some things felt off about the star of the fantasy. Her ass was rounder, the color of her hair wasn't dark brown, skin tone not as tanned, and perhaps most importantly, the noises she was making were ridiculously arousing.
The moans radiating from the petite woman bouncing on his dick weren't drawn out and loud like typical overacting. Each sound was a little subdued but he could still detect desperation and an obvious desire to cum overflowing from every whimper. The fantasy ended with a stifled cry that sounded surprisingly like someone saying a name. Maybe his name, he wasn't sure exactly. If he had to bet he would probably have guessed he was hearing the throes of someone he knew, but he'd never heard anyone sound so lewd before. An orgasm like that just didn't sound anything like his experiences touching real girls. He'd never gotten far enough to actually lose his V-card but he'd briefly crossed third base once.
The aftermath of the fantasy rapidly melted away as Scott awoke to near total darkness and a gentle hand shaking him awake. He rubbed his eyes and tried to identify where he was until he remembered falling asleep on the living room couch. Moving around a bit, provided an immediate reminder of the vividly realistic fantasy that had caused his dick to harden in his still tented boxers. He ignored the uncomfortable tightness of his shorts and looked up at the figure leaning over him to get an explanation for his abrupt awakening.
"It's too cold in there. I can't sleep alone with this weather. Can you join me in bed? Please," Jane said drawing the word out long enough for Scott's eyes to fully adjust to the darkness.
"Fine. I'll come in a few minutes, sis. Just give me some space and I'll be right there before you know it," he said a bit hoarsely.
"Hurry. It's way colder than I expected," she said before skittering back to the bed.
Scott took the opportunity to grab a glass of water and relieve his slightly dry throat. Hoping he had spent enough time to not have a noticeable erection, he moved to the bedroom, dragging the comforter with him. All he could see on the mattress was a curled up bump covered by all the warm fabric he had available. As he approached the vaguely human bump, a small hand ventured out into the cold to try and pull him underneath the bundled up covers.
"Get over here. I need my personal heater."
He wiggled closer until the siblings were almost completely side by side before stopping, feeling the remaining empty space was an appropriate barrier. This was still not enough for Jane, though. She broached the remaining distance and wrapped her arms around her brother's torso. The feeling of a girl touching him so intimately began to bring up unwanted thoughts. Before he could object, his little sister gently placed her head on his chest. The regular movements of bodies softly breathing and combined warmth was strange but felt comfortable enough so he dropped his protest attempt.
"Why did you decide to help me out, Scott? I know you don't really need a maid or anything when you can just order take out if you're sick of cheap food. Your apartment really isn't that much of a pigsty either. We don't have the best relationship with all my pranks yet you agreed to help me anyway. Why?"
"'The Magnificent Jane' needed me. I couldn't turn you away when you were asking me for help for the first time in I don't know how many years."
She tightened her arms a bit in response and tilted her head to look into Scott's eyes. They stared at each other for a little while in comfortable silence before she responded.
"I really do love ya, bro. You know that, right?"
"I love you, too, sis. You mean a lot to me despite all of our differences. Having you here made my day a lot better than I expected."
He wrapped his right arm around her in a gentle one-armed hug. Another brief silence ensued as they basked in each other's comfortable embrace while the sounds of distant cars and city life filled the void with ambient noise.
"Scott, do you ever feel like there's something you wish you could just blurt out loud but you're worried about the consequences?"
"Yes."
"Me too."
"I'll tell you mine if you tell me yours."
"I don't know if that's a good idea… If you promise to take me seriously, then I'll agree to share but you have to go first."
"Deal. Before you came over, I did masturbate to a certain girl you were hinting at. I just didn't do that this morning. I fell asleep afterward yesterday night and neglected to fully button my boxers when you woke me up with your prank."
"Hehehe, I knew it! You had 'I just masturbated' bedhead."
"Oh, really, what does that look like exactly? I'm wondering how much I miss when I see a messy-haired person and just go on with my day."
"Well… you could just look at my hair once in a while and see for yourself."
"Wait, you masturbated before coming over? I didn't notice anything unusual when you woke me up."
"Yep. And it's possible, maybe even definitely probable that I may have rubbed one off while in your apartment."
"Are you serious?"
"Yes. To be fair, I did muss my hair a bit to make it a little less obvious but I'm a sexually liberated girl and I don't need to be ashamed of my needs."
"I can't believe it. If you don't mind me asking, when did you masturbate while here?"
"You were falling asleep and I just couldn't help myself. I tiptoed to the bathroom and went to town. I came twice before finally feeling satisfied."
"Huh, I never would have suspected… You pull off erratic hair pretty damn well. Since you already know a few of my fantasies from snooping on my computer, which I'm still a little pissed about, by the way, want to share what you were imagining?"
"Are you sure you want to know?"
"No boundaries tonight. I can handle it."
"I was rubbing myself to the thought of someone hearing me touch myself, opening the door, and taking me right there against the bathroom wall until we were both satisfied. You know, a really hard fuck, one that takes everything else off your mind and the world condenses to just a passionate moment shared between two lovers."

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