πŸ“š the tutor's descent Part 1 of 4
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The Tutors Descent Ch 01

The Tutors Descent Ch 01

by lapislit
19 min read
4.5 (55200 views)
adultfiction

Disclaimer: This series deals with themes of cheating and dubious consent. This first chapter mainly sets the stage for many spicier additions that will follow.

I hope you enjoy it, and feedback is always appreciated.

*****

Olivia adjusted the rigid straps of her backpack in an attempt to alleviate some of the added weight from her newly acquired text books. "I still can't believe how much these cost," she complained to her boyfriend. "It's absolutely criminal!" The twenty-one year old student was seething, having just watched her modest materials stipend vanish before her eyes.

"I know, totally unfair," Daniel agreed. "I would've bought them for you, you know..."

"We already talked about this. I appreciate the offer, but I want to make my

own

way," she reminded him, silently cursing her own need to feel independent. Olivia Moore was a bright young woman who had earned her way into the prestigious university through means of a scholarship. Unlike her boyfriend, she did not come from a wealthy family, and her financial awards barely covered the cost of the schooling, let alone the ever rising price tags on the required texts.

Though she was living that stereotypical "poor college kid" life, it certainly wasn't all bad. Olivia was beginning her third year at the school she'd had her sights set on since she was a young teenager, and was well on her way to achieving her dream of becoming an aerospace engineer. Having grown up in a small town all her life, she was still adjusting to the explosion of new cultures, ideas, and types of people she was now surrounded by in the lively college town. She intertwined her slender fingers with Daniel's, another dream that had practically fallen into her lap the previous year. He was tall, athletic, and handsome - the kind of catch she would never have expected to notice her a few years back, nevermind date her.

A late bloomer, Olivia still hadn't gotten used to the fact that she was now what most would refer to as objectively attractive. She'd considered herself below average in the looks department for her whole life, and never received much attention from the opposite sex growing up, despite finding herself drawn to many of the boys in her classes. It wasn't until after high school that she finally grew into her awkward, gangly body, her womanly curves filling out nicely and her face clearing up. The deep-seated feeling of being undesirable did not go away overnight, and even after her transformation, it took time to gain confidence in herself. The nerdy men she was often surrounded by in her engineering classes were not bold enough to make a move on her, further prolonging the negative sentiment.

Daniel Taylor had been one of the first men to approach her romantically, and he had been the main catalyst for her finally coming out of her shell over the past year or so. They locked eyes in a study group for a general education class one afternoon, and to Olivia's surprise he began flirting with her in a way she'd only observed as an outsider. She was completely tongue-tied, but Daniel found her innocence charming, and asked her out on the spot. They soon were dating exclusively, and she eventually lost her virginity with him. Though she outwardly remained relatively conservative in her sexuality, the neglected girl within her was elated to continue the exploration of that new frontier. The couple had sex fairly regularly, and she enjoyed the intimacy, even though she felt a bit shy and awkward most of the time. Sometimes Olivia would wonder if she was doing

it

right, but her boyfriend seemed satisfied, so she didn't dwell on the matter.

"You could always get a part-time job," Daniel suggested, admiring the way her dark-brown hair wisped across her bright blue eyes in the light breeze.

"Yeah... I looked into a few around campus, but the pay sucks. It's barely worth the effort." She recalled the job she had at the bookstore the previous year, where they demanded more and more of her time until she had to quit due to the workload of her many courses.

"I might know of an opportunity actually..." Daniel started, trailing off in a way that suggested his reluctance to share the idea.

"What?" Olivia inquired, her interest piqued by the mere fact that her boyfriend seemed to be harboring something interesting.

"Well... I happen to know that my parents are looking for someone to tutor my little brother, but..."

"But what?" She asked, perking up at the idea of an easy gig that she might be suited for.

"I dunno... He's... Kind of a weirdo? I guess? Sort of a lost cause if you ask me," Daniel explained.

"A lost cause? That's kind of messed up, don't you think? What is he struggling with?"

"He's just always been a strange loner. And he's always on the verge of failing. Barely made it through high school by the skin of his teeth. He took one year off after that, and basically did nothing. My mom's forcing this to make sure he gets off on the right foot at the community college this year. Anyway, we never really got along that well. I don't know how to explain it."

Olivia felt slightly triggered by her boyfriend's sweeping description of his own brother, remembering back to her own days feeling like an outcast. "Well if he's your brother it can't be that bad! I'm sure he just needs the right encouragement," she argued, finding herself suddenly impassioned about this boy she'd never met.

"Maybe..." Daniel looked uncomfortable.

"Interesting," she muttered as she studied his apprehension. "So does this have anything to do with why you never talk about your family? And why I've never met them despite how close they live?"

"I guess, a little. My family's just odd in general. We don't always see eye to eye. I didn't want you to meet them too soon and get scared off, ya know?" He answered honestly.

"Hey, I get it, we all have weird families. Mine is across the country and barely speaks to me. They don't define who we are." She wrapped her arms around his neck, flashing a bright smile as his demeanor relaxed. "So... how much are they paying?"

"Not sure, but knowing my Mom, I'll bet it's beyond decent," he couldn't help but return her infectious smile, her adorable dimples melting his heart as always. "You want me to set it up?" She nodded cutely, and planted a firm kiss on his lips.

******

The arrangements had been made, and Olivia found herself parking her beater of a car on the curb beside a very well manicured and expansive lawn on a clear Saturday afternoon. "Wow," she murmured under her breath as she beheld the impressive house tucked into the refined landscaping. It wasn't quite a mansion, but certainly the dwelling of an affluent upper-middle class family. It felt strange to be visiting her boyfriend's childhood home for the first time without him, but he was busy with other obligations. She stepped out onto the street and closed the door to her embarrassing hunk of metal, cringing at its signature squeal, which seemed more out of place than ever in the present neighborhood. After wrestling with the thought to move her vehicle someplace more remote, she straightened out her dress shirt, which was tighter around her chest than would be ideal, and made her way up the paved walkway to the front door.

Upon reaching the entrance, she rang the doorbell and waited nervously, again fidgeting with her shirt and attempting to rub out a wrinkle she'd just found. A minute passed, when finally the large door swung inward to reveal an elegant middle-aged woman, who met her gaze with a closed lip smile. "You must be Olivia, please come in."

"And you must be Daniel's mother, nice to finally meet you," Olivia greeted the tall matriarch warmly. They shook hands, and she allowed her eyes to wander around the large foyer. "What a magnificent house!" She added in admiration.

'Mother?' 'Magnificent?' I don't think I've ever used either of those words.

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"Mmm," Mrs. Taylor acknowledged the compliment wordlessly, wearing the same half-smile. "I'm sure your time is valuable, Matt is just through these doors." She floated across the room, leading Olivia into another space which appeared to be some sort of sitting room where a small table had been placed in the center. A wiry young man with jet black hair was slumped in one of the chairs, and lazily rolled his head towards the newcomers.

"Come meet Olivia," the parent yapped at her son, who reluctantly stood from his chair and sauntered over. "You had better take this seriously," she warned him. "I'll leave you both to it then." Clearly in a hurry to be elsewhere, Mrs. Taylor swiftly departed behind the closed doors and left the two students awkwardly facing one another.

"Hi. You're Daniel's brother, Matt? I'm Olivia." Her eyes quickly scanned his thin frame. There was a vague resemblance to her boyfriend in his facial features, but the young man was nearly opposite to his sibling in most physical aspects. His complexion was darker, like his mother's, and there was seemingly little to no muscle on his almost skeletal structure. She reached out to shake his pale hand, and he took hers weakly, his eyes shying away from hers, and focusing mostly on her body. Olivia was suddenly reminded of her ill-fitting shirt, and felt exposed.

Is he staring at my chest?

"Hey." He said simply. He was taller than her, but a good deal shorter than his older brother. His hand lingered on hers marginally longer than socially acceptable, before he withdrew it and sat back down at the table. Olivia joined him in the empty chair beside him. She had tutored a few young children whilst in high school, but starting the process with someone who was basically her peer felt strange. She decided the best way to dispel the awkwardness was to dive in.

"So, which class are you working-"

"Listen, I really don't want to do this," Matt interrupted. "Feel free to just chill or whatever and I'll tell my mom you're helping me so you can get paid. I'm just here to get her off my back already," he explained, reclining in his seat and focusing on his phone screen.

It's gonna be like that then...

Olivia thought to herself as she observed the negligent nineteen year old. "Well since we're here, we might as well try a little, right?" She suggested, trying to mix just the right amount of enthusiasm into her voice.

"Nah," he grunted dismissively.

How am I supposed to get through to this guy?

She felt determination swelling within, her eyes darting around the room as she searched for an idea.

There's gotta be something he cares about...

"So you're not interested in going to college at all?"

"Not really..." He shot her a quick glance before returning his attention to his screen, and spoke again. "Mom's making me do it or else."

"Or else what?"

"Kicking me out. No allowance, no support. Bitch," he grumbled.

Olivia felt a slight shock at his hateful words, but paused for a moment and allowed her compassion to shine through. Afterall, she really didn't know a thing about the inner workings of the family's dynamics. "That's rough. What is it you

want

to do?" She asked, maintaining a neutral tone. He shrugged. "There's gotta be something... right?" Olivia pried gently again, crossing her arms and mirroring his relaxed posture. Still, the young man did not respond. "Matt, I promise I'm not here to pressure you into doing anything you don't want to. We can just hang out and get to know each other for now."

Matt's eyes panned back over to his tutor, lingering for a second before returning to the screen. Though he was pissed that he was being forced to take time out of his day to be with her, the fact that she was so attractive at least made it a little interesting. "Mkay," he said. He sensed her relax further upon hearing his agreement, and stole another quick peek at her body. The way she was sitting with her arms folded under her chest accentuated her tits nicely, and it was difficult for him to look elsewhere. He became aware of her staring at him, which gave him an odd feeling in his gut. It wasn't often that he had a beautiful girl taking an interest in him.

"So, what would you rather be doing right now?" Olivia asked after taking enough time to avoid being considered a pest.

Jerking off to the image of you taking that shirt off for me,

Matt thought deviously. "I dunno... Maybe like... Making videos and stuff."

"Well that's cool!" She replied encouragingly. "You could totally transfer to a film school or something I bet." Matt grunted, and sensing his hesitation, Olivia decided not to press him with a specific path. She was making progress. "I get it. Lots of people your-well,

our

age don't know exactly what they want to do with the rest of their life. But, that's why community college is so useful! You just get the basic stuff out of the way and it gives you time to figure all of that out."

"I guess..." He responded. The attractive tutor's charm was having an effect on him, and he found himself more inclined to comply with her, if only to keep her in his presence.

Olivia was feeling the fire of victory, but reminded herself to stay casual. "I bet you'll find these classes easy once you spend a little time with me," she giggled proudly, reaching across the desk to grab a sheet of paper and pencil.

Matt seized the moment to stare longingly at her alluring cleavage as she leaned forward. She might have been the hottest girl he'd ever been this close to, and he felt the sting of jealousy already at the thought that his older brother had access to her delectable body. He adjusted his increasingly uncomfortable crotch at the thought of her full, fleshy chest spilling out of her tight top.

The rest of the session went surprisingly well, despite Matt's initial reluctance. While he was still distracted and unenthusiastic, Olivia was able to help him through half of his Math assignment, demonstrating some of her personal tricks. He actually seemed to catch on, and she encouraged him every step of the way. She did notice his wandering eyes on her a few times, but chalked it up to normal "Guy" behavior, and didn't think much of it. If he thought she was cute, then that would only help her keep his attention, which she felt was a net positive towards her goal of turning him into a successful student.

As the hour-long sitting came to an end, Matt's mom appeared in the doorway once again. Olivia gave her a brief summary of what they had worked on, which seemed to satisfy the woman, who then offered her an envelope. "Is a check alright?"

"Uh, sure!"

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"I hope you find that amount fair and competitive. Please don't hesitate to let me know if it's insufficient," she explained with an air of formality. Olivia wasn't certain what the protocol was for that moment, and thanked her with a wide smile. She waved goodbye to Matt and was soon back in the privacy of her car. Only then did she open the envelope and inspect the check. She chuckled upon noticing that the elder woman's handwriting somehow matched her physical appearance perfectly. Then her jaw dropped after reading the number.

For one hour?

The amount exceeded an entire week's pay at her previous job.

Maybe this is for the whole month or something.

Before leaving, they had agreed that she would show up for the same time the following week.

Guess I'll find out then.

******

That night, Olivia met up with her boyfriend for dinner at a casual restaurant near campus. He seemed nervous at first, as if she was going to wearily pronounce her new understanding of his issues with his family, but he steadily relaxed as she explained how the first appointment actually went. "He's definitely strange, and seems to lack confidence, but I think I can help him!" She explained, taking a bite of her food and chewing thoughtfully.

"If anyone can, I suppose it's you," Daniel replied. Though he'd rather his girlfriend and little brother not associate, he couldn't help but admire her optimism and conviction.

"He just needs some guidance I think, like a positive role model. I'm up for the challenge!"

"Something tells me it's going to be a challenge alright..." He murmured.

She shrugged off his comment, figuring most siblings had an element of conflict to their relationship. She didn't have any brothers or sisters of her own to provide personal context. "And the pay doesn't hurt either!" Olivia added.

"For sure. I knew it would be good. My mom can be kinda cold, but she is generous with her money when she believes in the cause," he explained. The couple carried on with their meal, and Olivia asked more questions about her boyfriend's mysterious family, learning that his mother was a successful business woman, and that his father had opted to partake in his hobbies full time, since the family finances were secured. Apparently this was a point of contention between his parents. "They fought a lot growing up, but over the years my dad has become sort of withdrawn and just does his own thing mostly. I think Matt takes after him more. My mom always favored me, but sometimes the pressure was too much, and we aren't exactly the closest anymore."

Olivia listened to his details with curiosity, realizing more and more how different their upbringing had been. Her parents had been warm and loving, supporting her in her endeavors. They may have been a little overprotective, but overall felt her family unit through childhood had been a healthy one. The young girlfriend realized that she felt a certain sense of responsibility to help those who had not been as fortunate as her.

******

The week progressed quickly, the hustle and bustle of settling into the new semester's schedule leaving little time for much else. Before she knew it, Olivia was back on the cobbled path through the immaculate landscaping for her new gig. Mrs. Taylor answered the door again, seemingly even more distracted this time, and gestured towards the "study" after a quick greeting. The tutor entered the quiet room and shut the entrance behind her.

She found Matt slumped in his chair, much like the first time she saw him, but this time his dark pupils were fixed on her. "Hey, Matt, what's up?" She asked cheerfully, all too aware of him scanning her body as she approached him.

I really need to remember to buy more clothes soon

, she thought, his stare reminding her of her tight fit.

"Yo," he answered, slowly straightening up.

God, she's fucking sexy...

"Ready to tackle some more Math problems?" Olivia asked, thinking she would have liked to have asked in a "cooler" way.

"I guess..." While he wasn't thrilled to work, he was looking forward to stealing peaks at her breasts for the next hour.

"Ok, so where did we leave off... That's right, systems of equations." She leaned in to view the homework question he had displayed on his tablet. "Do you remember the first step?" She asked, observing his eyes dart away from her chest at the last second.

"Uhhh..." He hadn't really heard her question, and fidgeted with his stylus for a while.

"You line up the variables, like this..." Olivia motioned to the numbers on the screen, instructing patiently as Matt rearranged the equations. "Good! So next-"

"What's your major?" He blurted out.

"Aerospace engineering," she answered, cringing at the slight tone of elitism apparent in her own voice.

"Wow, so like space stuff?" Matt answered, playing dumb.

"Kinda. Basically all things flying."

"Isn't that more like a guy thing?"

Olivia calmed her pulse after a moment of reacting negatively to his borderline misogynistic implications. He was just a sheltered, naive kid, she reminded herself.

He's nineteen actually,

her inner voice argued. "Um, well no. I mean, what you choose to study has nothing to do with sex or gender. Though I suppose technically that field is more historically male dominated. But that's changing. Anyway-" she felt herself getting flustered and stopped herself to focus on why she was there. "Do you remember step 2?"

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