The Tutor's Descent

Disclaimer: This series deals with themes of cheating and dubious consent.

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

******

Olivia woke the next day to a text from Daniel, asking her if she'd like to grab dinner with him later that day. She felt a pang of guilt at reading the message, remembering her naughty escapade the previous evening, but told herself again that she was simply blowing off steam. Once she made up with her boyfriend, there would be no reason to stumble back into those darker corners of the internet.

After a routine day of classes, the couple met up at their favorite restaurant. Daniel was the first to speak, clearly eager to bury the hatchet and move on. "I'm really sorry, babe. I know I overreacted, and I feel terrible. Will you please forgive me?"

Feeling no inclination to continue living with the uncomfortable rift between them, Olivia forgave him immediately, squeezing his hand across the table reassuringly. She had the passing thought to come clean herself and explain to him that her last session with his brother had gotten a little strange, but feared it would just upset him again and ruin things between them irreparably. She also still wasn't sure whether or not there was any truth to Matt's disclosure about how his big brother had bullied him, but decided to keep the matter to herself for the time being. The attractive pair enjoyed their meal together, keeping the rest of the conversation light-hearted and amicable, before returning to Olivia's apartment for some after-dinner entertainment.

Olivia had heard the term "make up sex" before, and was secretly looking forward to experiencing if it truly was some heightened form of the act. The sex ended up being fairly routine though, and she found her mind wandering more than ever before. She had never given much thought to

how

her boyfriend felt inside of her, just that he was in there and that's what sex was. The obscene porn she'd viewed was fresh in her mind, all of those filthy examples of big, girthy dicks stretching holes open plaguing her thoughts as Daniel's much smaller tool slipped in and out of her.

Were those women in the videos really having orgasms from just the penetration alone?

It had never happened to her, and she'd usually tend to her own climax after he was done, or not at all. On occasion, he would lick and rub her clit after finishing himself, which sometimes got the job done. Often though, she would feel too pressured and couldn't actually get off.

Daniel eventually came, filling the condom with his seed, and collapsed beside his girlfriend. She'd done her best to fake a climax to avoid him prying into her thoughts. It's not that the sex wasn't enjoyable - Olivia still enjoyed the intimacy and pleasure they had shared. It was just the nagging idea that she was quite possibly missing out on some unknown potential. She ran her fingers along her boyfriend's muscled chest, admiring the physical specimen that she was now questioning for some reason.

What is wrong with me? Most girls would kill to be dating this beautiful man. One stupid little trip to "pornville", and now I'm doubting my sex life?

She thought about how ridiculous it was to be letting the barrage of thoughts affect her so suddenly, but deep down the questions had always been there.

******

Olivia drew a deep breath and exhaled her nervous energy before emerging from her car on the well shaded street.

No reason to act weird

, she reminded herself, determined to be calm and mature regardless of what Matt might say to her. She worried that he would somehow know that his comment had contributed to her racy internet search, but that was of course impossible. Mrs. Taylor greeted her at the grand entrance, ushering her inside with her usual air of floaty elegance.

"Matt's first big exam is the day after tomorrow. I trust you'll make sure he is prepared," the woman spoke suggestively, smiling, but with a glint of authority behind her expression.

"I'll do my best!" Olivia answered with enthusiasm as the mother vanished through a different hallway, clearly occupied and already speaking to someone else through her ear bud. The tutor quietly opened one of the doors to the study and closed it behind her. "Hi Matt," she called to her student, his face buried in his phone as usual.

He greeted her casually as she joined him at the table, his eyes thoroughly scanning her feminine figure. She looked stunning as usual, and her presence was enough to fuel his already aroused state. Matt had considered relieving himself before she arrived, but decided against it. It would be better to save it for after their time together. He squeezed his erection, which ran for a considerable length down his thigh. He noted that Olivia's attention momentarily shifted, apparently aware of his subtle movements beneath the table.

"So how do you feel about that upcoming exam?" She asked, brushing off the discovery that he already appeared to be touching himself.

"That it's gonna suck..."

"Oh, come on! You got this. Let's review everything we've worked on," she encouraged, taking control of his tablet. Olivia guided him through a few simple problems, gradually progressing in difficulty and reintroducing new concepts. Matt seemed unenthused, but was at least participating with the little energy he put forth. After completing a particularly tricky item that he struggled through, she felt his focus slipping, and tried to shake things up. "Nice! Alright, so how are things? Any girls in class catching your eye?" The second the impulsive inquiry left her tongue, Olivia regretted bringing up the subject.

"Eh... Well there is this one..." He started, playing coy as if he was reluctant to talk about it.

"Oh?" Her curiosity was provoked, and she figured this could be an opportunity to help him through something besides academics, which could make a big impact. "You can tell me."

"She's super hot, and seems actually smart and kind, unlike most pretty girls or whatever..."

"Hm... Okay, so have you talked to her?"

"A little. Not really though... What do you think I should say to her?"

"Well, it's less about

what

you say, and more

how

you say it; and how you present yourself. Assuming you don't say something weird or creepy..." Olivia realized she was talking to exactly the kind of man that

would

in fact say something off putting. He was going to need more specific instructions, and a bit of a makeover wouldn't hurt either.

But we don't have time for all that,

she argued with herself. Was she really going to cross this line and become a "relationship advisor" figure? On one hand, it seemed like she was biting off more than she could chew, but on the other, it could be the key getting this troubled young guy out of his shell and on the path to a more normal existence. If she was in the position to make that much of a positive difference in someone's life, she had to try.

"So cryptic. How the hell am I supposed to know what she finds creepy or not?" Matt asked.

"Let's finish another review question first," Olivia suggested, seizing the opportunity to have captured the key to his motivation. He agreed reluctantly, and they were able to carry on with the session at a consistently productive pace. Throughout their remaining time together, she offered him little tips and pieces of advice, mainly geared towards carrying himself as genuine and casual when approaching the mystery girl.

"And remember that if she's not interested, you have to just accept that and keep playing it cool. Rejection is a normal part of dating, and you can't let it throw you off," Olivia explained.

"Easy for you to say. No guy in his right mind would reject you..."

"Uhh, you'd be surprised. Your brother is actually my first boyfriend. I actually had a lot of trouble with this stuff until very recently."

"Wow, it's hard to believe you were an incel too."

"You're not an incel! You just have to be confident and put yourself out there. Things will turn around if you put in the effort, I promise," she argued, clasping her fingers around his forearm to punctuate her sincerity. Her touch was intoxicating, and he needed more.

"Um. So if she

does

agree to grab coffee with me or whatever, is it okay to like, hug her?"

"That could be fine. It all depends on the vibes I guess. If she seems receptive, you could go in for a quick friendly hug. Just remember to keep it casual." It seemed like such an overly specific question, but reminded her of her own past self, obsessing over the minor details of courtship and physical contact, having had no experience to draw from.

"Can you tell me if I'm doing it right?"

"You're asking for hugging lessons?" Olivia had to suppress a laugh.

"I know it's kinda dumb. I don't know what to do with my hands I guess..."

"Oh my God, Matt," she said, now giggling a bit at his expense. "Alright then. Come on." She stood and faced him. "Just a regular old hug. Don't overthink it."

He rose to his feet and took a step towards her with outstretched arms, wrapping them around her torso and pulling her in for a tight embrace. His strength surprised her a bit, and she chuckled as her hands found his shoulder blades. "Not too firm," she instructed, and his hold loosened a little.

"Like this?" He asked quietly, savoring every single microsecond that passed. The way her supple body felt pressed against his was almost magical, and no detail went unnoticed. Matt could feel her soft, full chest enveloping his as her flowery scent filled his nostrils. The young man felt his cock twitch in response to the alluring womanly figure assaulting his senses.

Olivia wondered if she'd made a mistake agreeing to the awkward embrace. The poor guy was clearly starved for physical contact though, and it seemed innocent enough.

Sometimes people just need a damn hug

, she thought, feeling charitable and allowing herself to sink into it. Then she felt something throb against her lower belly, and her eyes widened. The sensation was impossible to ignore, and she stood there, frozen in disbelief as something large and firm expanded between them. "Uhh, Matt?"

"Huh?" He asked absent-mindedly in the middle of a daydream, before crashing back down to Earth. "Oh... Shit, sorry," He apologized, realizing that she must be able to feel his rapidly growing erection. It felt amazing sandwiched between their bodies, and he fought the urge to thrust his hips into her.

"Matt!" She shrieked, trying to push away from his unrelenting hold.

"Sorry!" He shouted, letting go of her and instinctively grabbing the large shaft tenting his shorts.

Olivia nearly fell on her ass, stumbling backwards and catching the chair just in time. She watched in bewilderment as her boyfriend's little brother frantically tried to tame his massive bulge, fidgeting with it before opting to sit back down and cover himself with his arms. Her heart was racing, but her feet remained planted in place despite a few moments of indecision with what to do next.

"I'm really sorry. I-I couldn't help it," Matt stammered. Olivia wrestled with the urge to reprimand him. He seemed genuinely apologetic, and it was just a normal human reaction. He was probably more embarrassed than her, she reasoned. "I swear I didn't mean to. You're just so-fucking-pretty, and I-"

"Okay, okay," she interrupted him, her expression softening. It was actually kind of endearing watching him squirm and try to explain away his body's response. If it wasn't such an inappropriate dynamic, she supposed she could even feel flattered for getting such a rise out of him with a simple hug. "It's fine, I know that... Er... Heard it can be kinda hard to control sometimes," she said understandingly, sitting back down and trying to act like nothing out of the ordinary had happened.

"It's

really hard

sometimes..." Matt muttered. The double entendre was not lost on her, but Olivia had to believe he didn't mean it that way.

"Well, I think that hug might've been a little too long for a new acquaintance, by the way," she laughed, cutting the tension.

He smiled widely. The fact that she hadn't run away yet was nothing short of incredible. "Noted," he answered. "What am I supposed to do if that happens again though?"

Now I'm expected to give him advice on how to conceal his big penis? How did we end up here?

"Uhh... I don't know what to tell you. You gotta figure that one out on your own..." Her eyes wandered down the length of his arm, and she noticed him squeezing his hardness. "Matt! I don't think continuing to touch it is gonna help!"

"Ugh, sorry," he grunted in frustration, removing his hand. Olivia failed to tear her attention away in time and witnessed his snake-like manhood visibly throb, as if it was a ticking time bomb about to explode. "It won't go away," he muttered, looking at her like he was in pain. The moment was surreal, and she found herself briefly wondering what it might feel like to be a man with a big uncomfortable erection trapped in your pants. Especially one this big. She could hardly believe it was even real, and considered the possibility that he had stuffed something in there to fool her, or feel better about himself. If it wasn't for those dirty videos she'd seen, the concept of that massive bulge actually being a penis would seem impossible. The creak of the double doors snapped her out of her daze, and she awkwardly shot into an upright posture upon noticing Mrs. Taylor entering the room.

"You're still here? Preparing well I see," the woman said with the slightest hint of suspicion in her tone. Olivia looked at her phone and noticed that they had gone over the allotted time by about twenty minutes.

"Heh, yeah. Gotta make sure we pass that test with flying colors, right Matt?" She saw in her periphery that he had dropped the tablet into his lap to conceal his tent.

"Mhm." He answered

.

"Okay, well I should get going. I think you're ready. Best of luck on your exam. Maybe read through that review assignment one last time before bed," she suggested.

"Can I get a good luck hug before you go?" Matt asked, smirking as he inched towards her.

"I-uh. Well..." Olivia stuttered, painfully aware that his mom was still observing their interaction.

It would be weird to refuse it, right?

"Okay..." She forced a smile and stepped into his open arms, which clasped around her tightly.

"Thanks so much for all the help today," he murmured.

She forced a light chuckle. "No problem. You got this!" She could feel his hardness again, swelling up against her own pelvic region before he released her and quickly turned away. Olivia giggled awkwardly as she joined Mrs. Taylor and accepted her payment. The woman looked impressed, probably not used to seeing her son in such good spirits.

"I think Matt might have a little crush on you," she said teasingly as they left the man

behind and approached the front door.

"Heh, oh I dunno about that. I'm glad he's doing better in his classes," the tutorreplied, changing the subject.

"As am I. You've really made quite an impact already, young lady. I think we'll have a little family barbeque to celebrate if he passes this test."

"That'd be nice. Fingers crossed!" Olivia responded before setting off on the cobbled path. It had been a strange afternoon, and her mind was full of unprocessed thoughts. Had she really just felt her boyfriend's brother's big, hard dick pressing into her? Was his request for a second hug solely so he could feel her body against it again? Was he so attracted to her that holding her for a few seconds had made him that uncontrollably erect? She thought about how he couldn't keep his hands off of it, and how strained it seemed in the confines of his pants. She wondered if he was rubbing it at that very moment to the thought of her, unable to stop himself from chasing an orgasm with the fresh memory of sharing intimate contact with her. "Fuck..." She mumbled audibly to herself, in a daze. "Fuck!" She woke suddenly, realizing she'd missed her turn. "Get a fucking grip, Olivia," she told herself, trying to fight away the dirty thoughts and images plaguing her.

The internal battle carried on for the remainder of her short drive home, and well into the rest of the night. The unmistakable wetness between her legs refused to be ignored, and she eventually caved, shamefully rubbing her soaking pussy and watching porn in the privacy of her bedroom for the second time that week.

******

"It's pretty weird that this is the first time we'll both be at your family's house at the same time," Olivia said to Daniel, who was driving them both across town to the dwelling she'd been visiting and working at for weeks.

"I know, you're always over there while I'm at practice and stuff," her boyfriend replied. He wasn't in the best mood, and wouldn't have accepted the offer for a day of swimming and eating grilled meats if it hadn't been for Olivia's convincing.

"I think we both know there's more to it than that," she said suggestively. It was no secret that Daniel wasn't the biggest fan of spending time with his parents and little brother. Olivia wasn't showing it, but she was also a little nervous about the upcoming gathering. The true nature of the dynamic between her boyfriend and her student was still a mystery to her, and she wasn't sure how it would play out. Matt's strangeness and lack of appropriate social etiquette towards her was also worrisome, but she reasoned that having Daniel by her side would put an end to some of those behaviors. The hope was that by spending the day all together, they could shake out and resolve any of the awkward tension that might still be in the air.

"Well, here goes nothing..." The athletic man muttered as he parked his luxury sedan.

"Oh, come on! Let's just try and have a good time. We can relax our grip on the past a little for today, okay? Maybe this can be an opportunity for you guys to make amends and be cool again." Olivia encouraged him, and earned a quick kiss on the lips signifying his agreement with her optimistic approach. She trotted behind her boyfriend in her flip flops, feeling the sun on her shoulders. It was a warm day for late September, the last of Summer clinging to the land for its final days. The young girlfriend was sporting a light sundress that covered up her two-piece bikini. She'd had the thought that her swimsuit might be too revealing given the circumstances, but Daniel had bought it for her earlier that year and encouraged her to wear it. He couldn't pass up the opportunity to admire her body in the sexy garment.

The front door opened to reveal Matt, who ushered them inside. Olivia couldn't help but notice that he was sporting a bulge beneath his thin swim trunks. "Congrats on your test!" She barely got the words out before Matt's arms swung around her and pulled her in for a hug.

So we're hugging every time now eh?

She shot a glance at Daniel, who looked less than thrilled about the interaction, but didn't say anything. Luckily, the younger man let go of her in a timely fashion, and muttered an unenthusiastic greeting to his older brother.

As they made their way to the back of the house, Olivia got her first glimpse at the lavish living room and kitchen, which seemed to almost sparkle as she passed it. The backyard was no less impressive, the sprawling resort-style pool surrounded with tropical plant-life and expensive looking furniture. She spotted Mrs. Taylor across the yard, on her phone and animatedly talking to whomever was on the other line. A shirtless man with a deep tan turned away from a smouldering grill, smiling widely at her.

"You must be Olivia!" The middle-aged father greeted her, extending his muscled arm.