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The Tutor's Descent Ch. 02 - Full Prerelease
🕑 Added 2025-02-27 16:17:20 +0000 UTCIf you're enjoying this story so far and have already read the previews, you may want to read this entire prerelease. There is a small chunk of completely new text at the end, but I also made some changes throughout that I think improve the chapter.
Also, chapter one was published on Literotica today, and I'd greatly appreciate a nice rating and favorite if you enjoyed it here already. The more traction it gets, the more likely I am to dedicate as much time as possible to this.
You all are the best. Chapter 3 is already in the works.
******
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.
She shook his much larger hand a bit nervously. “Hi, yes. Mr. Taylor?” She noted the small lines around his eyes, but instead of making him look old, they added to his charm. He had the same sparkling eyes and athletic build as Dan, just a more seasoned version. “Nice to finally meet you,” Olivia added politely.
“Call me Jack,” he said warmly. “Glad to see Dan here pulled himself a real treasure,” he continued, unabashedly scanning her body to enunciate his point.
“Alright Dad, that’s enough creepin’,” Daniel joked. He wouldn’t show it, but he was a little concerned with all of the attention Olivia was already getting from the other guys. He couldn’t blame them though; she was gorgeous, but most importantly, all his.
“Hope you guys are hungry,” Jack called out, as he turned his attention back to his smoking cooktop.
Olivia followed Daniel to a table nearby where he removed his shirt and kicked off his shoes. She did the same, pulling her dress up and off of her body in one smooth motion. Feeling the open air on her exposed skin, she quickly grabbed a towel and draped it over her shoulders. She looked up just in time to see Matt dart his head away from her. He had undoubtedly been watching her undress, but she chose to pretend not to have noticed. Daniel led the charge to the shimmering waters and lept into them, making a big splash. Soon, the three young adults were submerged and acclimating to the refreshing coolness of the pool.
After some idle swimming around, Olivia observed that Matt was keeping his distance, likely shy and unsure of how to act around his estranged older brother. “You guys should race or something!” She blurted out, trying to encourage some form of game that could ease the tension. The boys agreed, Daniel the more enthusiastic of the two, and they took their positions on either side of her. “I’ll be the judge. Ready… Go!” The men took off, the older brother unsurprisingly the better swimmer with a nearly perfect stroke. He effortlessly built a greater and greater lead on Matt, somersaulting beneath the water at the opposite end of the pool, and returned to Olivia victoriously.
He wrapped his arms around her and pulled her in for a kiss, surprising her with the public show of intimacy. She felt her pulse quicken the slightest bit, the skin on skin contact and sudden forwardness of his actions teasing the beginnings of a feeling of arousal. Daniel waited for Matt’s arrival before he let go of her. She began doubting her decision, realizing that an athletic feat was probably not the best activity for Matt’s shaky confidence.
Before she could suggest something else, Daniel doubled down on the challenge, splashing his brother as he finished his lap. “I bet I could swim here and back twice before you even get one in!”
Matt looked at Olivia, who appeared slightly concerned for him. On one hand, it was embarrassing to be bested in front of her, but he figured that if he continued playing nicely and allowing the day to go smoothly, he would get more opportunities to ogle his tutor’s exquisite body. He wasn’t really into swimming in the first place, and was only participating because of her presence. “Fine, let’s do it,” he accepted, brushing the dark mop of wet hair from his eyes. The race was on once again, and Matt pushed through the water as quickly as he could, almost immediately finding himself in the wake of his brother’s kicking legs. About halfway on his journey back to Olivia, Daniel passed him in the opposite direction. There was no way the older sibling would be able to win, and a mischievous idea occurred to Matt. He continued his frantic paddling straight towards the alluring woman, who was now unguarded.
Olivia cheered as Matt edged closer to her, Daniel’s arrogance proving to fall short of his abilities. Even though it was not a fair challenge, hopefully the younger brother could gain a morale boost from the win. As he drew within a foot of her, she realized he was not paying attention and was about to crash into her. Before she could dodge him, her tutee swam headfirst into her chest, his limbs splashing wildly. In the brief moment of chaos, Olivia could feel Matt’s hands grabbing at various parts of her body to steady himself.
“Fuck, my bad!” He exclaimed, gasping for air. The sound of Daniel’s continued splashing was still a fair distance behind him.
“No p-problem. Um. You can let go of me now,” Olivia stammered. Matt’s long fingers were firmly clutching her bare waist, pressing into her soft skin and jiggling her chest every so slightly as he treaded water. Something about the hungry look in his eyes, cornering her at the edge of the pool just out of reach from her boyfriend, stirred something in her. He complied just as his brother returned, returning to her side innocently.
“Damn! The little bastard didn’t cheat did he?” Daniel asked her, catching his breath.
“Oh, fuck off…” Matt muttered.
“No, he won fair and square, babe!” She replied, remembering to keep the mood light.
“Well, I still want my prize anyway,” the chiseled man stated, enclosing Olivia’s petite frame in his and planting his lips onto hers. He knew his brother had been getting an eyeful of his girlfriend’s mouth-watering assets, and couldn’t help but boldly display his claim over her. Daniel knew better than to get too confrontational with Matt that day, especially after the accusations of childhood bullying that had been made. He would continue to assert his dominance in other ways though, and planned to give the younger man a stern talking to when they were alone.
Olivia’s eyes widened as Daniel darted his tongue into her mouth, increasing the intensity of their kiss and further stoking her building lust before releasing her suddenly. She bobbed back into the water, feeling the flush of embarrassment on her face upon noticing Matt gawking at her. “I think I’m going to lay out for a bit,” she suggested, wanting to escape the tension surrounding the group. “Play nice,” she called out, climbing out from the pool and selecting a well-sunned lounge chair to occupy.
The antics beneath the waters had left Olivia feeling horny, and she couldn’t help but laugh to herself at the thought that normally she would get into the pool to cool off. The men began wrestling, and she watched them while the rays warmed her body, hoping they would remain playful and respect each other’s boundaries. As she observed the brothers grappling one another, she became aware of Mr. Taylor, who appeared to be staring at her from his barbeque station. Olivia felt exposed, the flimsy two-piece doing little to hide her glistening skin, but a part of her decided to do nothing about it. She couldn’t deny the excitement she felt to have all three of these men taking such an interest in her. She reasoned that just looking was harmless, and allowed herself to just revel in the flattery. The thought of them drooling over her did little to stave off the tingling she felt between her legs though.
“Time to eat!” Jack announced at some point, and the others slowly gathered around a large circular table. A picturesque spread of grilled chicken, steaks, and various sides were strewn about, and there was also a fancy cooler nearby filled with various chilled beverages. Olivia accepted a hard seltzer that Daniel offered her and took a generous sip, the crisp, bubbly liquid hitting the spot. The family served themselves and began digging in, saying little at first. Olivia noted how stiff they all seemed with each other, and wondered what exactly might be going on under the surface. Jack seemed relaxed and friendly enough, though there seemed to be some sort of barrier between him and his wife. She remembered Daniel’s explanation of their troubled relationship, though his dad’s first impression on her was not what she had expected given his description.
“So, thanks for coming you two,” Mrs. Taylor stated, finally breaking the silence. “I just want to express my appreciation for you and all your efforts to help our Matt here with his education,” she added quite formally, raising her glass of wine towards Olivia.
“Cheers to that,” Mr. Taylor added, and everyone took a sip from their drink.
“I’m more than happy to do it. You guys have been so kind to me, and I’m very pleased to be finally spending time with Daniel’s family,” Olvia said appreciatively, unintentionally mirroring the mother’s proper way of speaking.
The group engaged in a mostly shallow, light-hearted discussion about the young couple’s own plans for the rest of their schooling and eventual careers. Olivia, still wearing nothing but her bikini, caught the men’s wandering eyes on several occasions. At some point Daniel started stroking her thigh, which felt better than it should have given her state of heightened arousal. She was also a lightweight when it came to alcohol, and was already feeling a bit tipsy by the time Mr. Taylor handed her a second drink. The man had been knocking them back since she’d arrived and even began slurring his words a bit.
Mrs. Taylor was pulled away from the group once again by a phone call. The woman was seemingly always on the hook to respond to any issues that arose at her office. The others decided to hit the hot tub, which looked highly inviting with thick clouds of steam rising into the orange light of sunset. Olivia closed her eyes blissfully as a powerful jet of bubbles massaged her back muscles. She absent-mindedly sipped on her seltzer and enjoyed the warm comfort of the water while the boys talked sports.
Matt wasn’t contributing much though, the topic uninteresting to him, and was instead stealing glances at his tutor whenever he could. She looked so incredibly fuckable, her face flush from the heat and her bare feminine shoulders breaching the surface. The man was rock hard recounting how tender her taut midriff had felt when he’d groped her earlier. If only he could find a way to get his hands on her again. He squeezed his aching erection in frustration while he fantasized about drifting towards her and rubbing it all over her sexy little body.
Olivia noticed Matt studying her, and wondered if he was trying to think of a way to initiate a conversation. She smiled at him, and he shifted over to her side of the tub. “You having a fun day?” She asked.
“Actually, yeah. Normally I’d just stay in my room for this sort of thing, but then I’d miss out on hanging out with you,” he said bashfully. And depositing about a thousand bikini pics into my mental spank bank. Matt’s brain was overwhelmed by lust, and an idea occurred to him.
“Oh stop it,” she responded, giggling. “I’m glad to see you and Daniel are getting along.”
“Yeah. Hey, can I get a selfie of us?” He asked, dismissing her comment and flicking droplets from his hand before reaching for his nearby phone.
“Uh, sure,” She agreed. Matt was already scooting in to sit up against her. He held his phone outwards to get them both in frame, and she felt his body squish up against hers, as if there wasn’t already plenty of room to capture them both. She then felt his arm snaking behind her and wrapping around her torso, his fingers lightly digging into the soft skin just below her ribcage. “Cheeeeese…” She held her smile while he moved his phone around, capturing different angles. She noticed Daniel shoot her an inquisitive look, and she shrugged at him, the casual response signaling all was well. With a subtle nod he turned back to his heated conversation with his father. Matt was pulling her into him very firmly, like a child possessively clutching his favorite toy. Olivia felt his fingers ever so slowly crawling upward as he swayed, stopping just as they barely made contact with the delicate flesh at the bottom of her left breast. Her ass lifted slightly off of the seat as he hoisted her up, and she felt the cool air on her bikini top as he snapped more photos.
“Okay Matt, I think that’s enough…” She felt something brush up against her right forearm, which had drifted out towards him a little, still under the surface. What’s that? At first she didn’t think much of it since their bodies were so closely touching already. It was warm and soft against her skin, yet rigid, and seemed to be running vertically, perpendicular to her arm. Oh my God, what is that? She almost automatically reached out to feel it with her hand and identify it, but stopped herself. There’s no way he has his penis out right now, right?. “Matt. Please let go of me,” she said sternly, but quietly enough to not alert the others.
“Okay, no prob. I was just trying to get the perfect picture,” he explained innocently, drifting a mere few inches away.
Olivia thought she detected the slightest bit of smugness under his expression though, like he was proud of himself for pulling one over on her. His hands had disappeared into the dark waters, and she could only imagine what they were up to. She didn’t know whether to confront him though. Was it an accident? Deep down she knew it probably wasn’t. Connecting the dots, it was becoming obvious that he was looking for excuses to touch her, but was his boner really that hard to tame? He was apparently losing control in his battle with sexual starvation in her presence.
Once again, Olivia found herself conflicted with feelings of compassion for her tutee, and the alcohol wasn’t helping her straighten out her thoughts. She rationalized that he hadn’t necessarily crossed any hard lines yet, and that the problem would go away if she could successfully help him land a girlfriend. The part she had trouble admitting to herself though, was that twisted excitement she felt to be driving him so mad with so little effort. His big dick had apparently just leapt out of his swim shorts from the smallest amount of physical contact with her, and that thought turned her on immensely.
Matt tugged at his swollen hard on while measuring Olivia’s reaction. She’d just grazed his bare cock, and practically let him cop a feel of her tit. Yet she was still there, right next to him. Her delicious, barely clothed anatomy within his reach. Either she was completely oblivious, or she was secretly enjoying the attention. At any rate, he was buzzing and ready to explode from the risky encounter.
“I need to use the bathroom,” Olivia announced suddenly, climbing out of the tub and retrieving her phone, intensely aware of Matt’s eyes following her every move. She caught her boyfriend’s attention again, who gave her a simple set of directions and asked if she needed help. “I’ll be fine,” she replied, wrapping herself in a towel and strolling back into the house and through the living room towards the guest bathroom that Daniel had described. It was locked, and she could hear running water coming from the inside. She figured Mrs. Taylor must be in there, who’d disappeared from the group a while ago. Needing some time to cool off and calm her mind, Olivia decided to explore the house a bit. Maybe she’d find another bathroom along the way.
She eventually ended up at a staircase, and figured she’d peruse the second floor, climbing the opulent looking steps. She spotted what appeared to be a washroom at the end of a rather large hallway, and something caught her eye while she approached it. To her right, an ajar door provided a look into what she could only imagine was Matt’s bedroom. It was fairly messy, and she spotted some of his clothes she’d seen him wearing crumpled on the floor. Despite her better judgement, Olivia’s curiosity got the better of her, and she quietly ducked into the room for a closer look. She lied to herself and reasoned that perhaps she would find something that would provide some insight into how she could help him more effectively. Though there was a shred of truth to that, she mainly just felt like snooping and getting a small peek at how he lived.
The room was easily twice the size of her own childhood dwelling, but also twice as cluttered. The walls were adorned with posters covering posters amidst shelves lined with various trinkets. She got the sense that she was surrounded by a disorganized timeline of the boy’s ever-changing interests. She fought the urge to more closely inspect the many oddities, but her internal clock told her she’d trespassed long enough.
Olivia froze at the sound of footsteps approaching down the hall. They were getting louder, and In a thoughtless scramble to avoid being discovered, she ducked into the dark closet beside her. The opening was just wide enough to slip past, but still concealed anything inside. She fought to calm her breathing as the alarming sound of Matt’s bedroom door closing struck her. Maybe someone passing by shut it? Nope, shit. The footsteps continued, and her tutee’s shirtless figure appeared in her limited line of sight. If he goes to the closet, I’m so screwed. Olivia’s heart pounded relentlessly in her chest as she realized the possibility of him fetching a change of clothes in his present state was a likely possibility. Maybe he’s just grabbing something real quick… But why close the door then?
The trembling girlfriend watched as Matt hurriedly slid his swim trunks down to his ankles and sat at the edge of his bed. Her mouth fell open as his thick, hard cock sprang into view. The impossibly girthy, veiny shaft jutted out from his slender frame as if nature had deliberately overcompensated for the rest of his anatomy. Olivia stared in shock as he wrapped his fingers around the obscene thing and began stroking it in an up and down motion. Two heavy balls, that matched the rest of his package proportionally, bounced beneath his fist as he began furiously jerking off. His expression was the picture of absolute desire, his teeth bared as he bit his lower lip with determination. She then realized he was fixated on his phone, clutching it fiercely in his free hand while he serviced his big dick, grunting, “Ungh… Fucking hot… Bitch…”
Olivia knew she should look away, but she couldn’t tear her eyes from the erotic scene. Maybe it was her previously aroused state, but something about witnessing the young man in this carnal, private moment was intoxicating. She cursed herself for not stopping him and making herself known sooner, because it seemed too late. She didn’t have the courage to stop him now. Hopefully he would finish up soon and head back down to the others, leaving her free to sneak out and pretend like it never happened. The others… How long had she been gone? Was Daniel wondering where she was? Her anxiety seemed to manifest itself into the worst possible scenario, and she nearly screamed as her phone vibrated in her hand.
BZZZ BZZZ.
Olivia’s heart practically leapt out of her chest as the deafening sound rang out. Matt stopped his movements immediately, and looked towards his closet like a deer in headlights. “Hello? Who’s there?” He asked shakily, fumbling around nervously with his manhood. The tutor dared not answer, praying silently that he would disregard the interruption and move on; but to her horror, he bravely stood and began cautiously approaching the darkness that concealed her. Olivia made a last desperate attempt to duck behind some of the clothes hanging around her, but it was no use. The space was too shallow and cluttered to hide away that quickly. She simply held her palms out in front of her, trembling with fear and anticipation as he clutched the knob.
The door swung open forcefully, Matt’s own fear causing him to expose the potential threat as if he was ripping off a bandage. The cramped closet was flooded with light and the two locked eyes in silence for a moment, the sudden face to face encounter too surreal for words.
“What the fuck?” Matt muttered in shock.
“I’m sorry! I don’t know! I was–I got lost and…” Olivia stammered in a panic.
Matt was again trying to conceal his erection instinctually, but could do little to hide it with just his hands. “Were you spying on me?”
“No! I mean–I didn’t mean to! I just panicked!” She had the urge to flee, but he was blocking her way out.
The young man’s expression transformed slowly as he realized there was no real threat. In fact, a miraculous opportunity had just fallen into his lap. “You panicked, so you decided to watch me get naked and say nothing?” He asked accusingly, no longer trying to hide his bare cock.
Olivia quivered as the gravity of the situation became clear to her. She knew she was in an incredibly tough spot, having basically violated his privacy with no good excuse for it. “Matt, I know it looks bad, believe me. But I–”
“Why the hell would you hide? What were you doing in here anyway? Are you secretly some kind of creep?” He continued his barrage of accusations.
“No!” Olivia shouted in desperation, tears welling up in her terror-struck eyes. “I swear I’m not! Please, Matt. Please, can we pretend this never happened. I won’t say a single thing to anyone about this ever!”
“That’d be awfully convenient for you, wouldn’t it? What about me? I have to just live with the fact that my tutor spied on me jerking off in my own bedroom?”
“I know. I know. It’s not fair. But I promise you that it was an accident. Please let me go. I’ll do anything. You can have all the rest of the paychecks your mom gives me,” she begged him.
Matt took his still hard cock in his hand, and stroked it gently. His demeanor shifted again, and she saw the lust return to his eyes. “Okay, relax. I won’t tell anyone…”
Olivia released a massive sigh of relief, emptying her lungs of all the pent up anxiety.
“...But we have to make this fair for me... And I think it’s only fair if I get to finish…”
Her pupils dilated as the realization of what he was suggesting dawned on her. “But… Matt…”
“Shhh. I’m giving you this one chance to make it up to me. I want to see the real thing instead of that shitty pic we took. Now drop that towel,” he ordered.
The defeated woman shuddered with shame and disbelief at her predicament, her racing mind trying to grasp for some perfect sequence of words that would buy her freedom. She looked into his dark eyes submissively, silently pleading for forgiveness. Matt did not waver, and his command lingered in the air around them. The tables had turned, and the normally shy, timid boy was now in control. Her eyes fell slowly to his engorged member, which looked even more formidable now that it was inches away and pointing straight at her. He stroked its length slowly but deliberately, idling while he waited for her to expose herself for his pleasure. She was out of time, and with a heavy heart, Olivia let the towel fall to the floor, revealing her petite frame before his lustful gaze.
Matt grunted as his tutor’s bikini-clad figure came into view right in front of him. He’d been secretly ogling her all day, but now he had a private showing and he could inspect every detail as openly as he wanted. “Come into the light,” he muttered, taking a few steps back. She followed him reluctantly, her arms straight and awkwardly pinned to her sides. She stopped in the door frame, trying to maintain some distance between them. “Closer…” She obeyed, and drew nearer until her flat tummy was inches away from his rose-colored mushroom tip. The man could barely contain his excitement, the endless possibilities at his disposal overwhelming him. It was his first real sexual encounter with a woman, and it was to be his gorgeous tutor, an absolute dream come true. He took a deep breath and fought off his most base desire, which involved immediately pouncing on her and shoving his aching cock into her pussy. He yearned to take her completely, shedding himself of his virginity, but his better judgement told him to hold back. He had leverage, but if he leaned on it too heavily it could break, spoiling his chances to ever see her again.
Olivia had never before felt so utterly violated, reduced to a masturbatory visual aid. She stood on wobbly knees as her boyfriend’s brother pumped the skin of his shaft, his active eyes consuming every inch of her practically naked flesh. How in the hell did this happen? She couldn’t believe how quickly things had escalated to this point. One minute she was enjoying an innocent soak in the tub, and the next she was cornered in Matt’s bedroom while he openly jerked off to the sight of her. She was completely at his mercy, and prayed he would finish promptly. Too afraid to look him in the eyes, her gaze instead lingered on his huge cock. It was enthralling, the thick veins rippling all over the throbbing surface making it look almost unearthly. Even though she’d recently learned of the existence of such enormous packages, she doubted she would ever see one in person, let alone attached to someone so close to her. Matt certainly had not been lying when he shamelessly bragged about his size, nor when he suggested his older brother did not compare. She clenched her fists in shame as the dormant arousal within her came rushing back to the forefront.
“You are so fucking sexy… Turn around,” his instruction cut through her hypnotic state like a searing knife. She dared meet his eyes for a moment, and they did not suggest an ounce of patience. Olivia began turning her body away from him. “Slowly… Stop.” She froze, her back to him, and looked over her shoulder to gauge his intentions.
“What’re you… Gonna do?”
“Mmpf. I love your juicy ass,” he grunted, ignoring her question. She could feel the warmth radiating off of his body as he moved even closer. “You’ve been driving me fucking crazy, Olivia. Did you know that?” He whispered in her ear. His comment sent a shiver down her spine, and the growing wetness between her legs was more apparent than ever.
She didn’t know what to say. She had never intentionally teased him, but perhaps she’d let him indulge a little too much in the inappropriate conversations and recent touching. If only she had established that hard boundary to begin with, it was unlikely any of this would have happened. “I’m sorry…” Olivia replied weakly.
“I forgive you,” he muttered, still whispering. “You’re making it up to me now… Like a good girl…” His words chilled her to her core. How was this the same sheepish youth that she had been guiding? Was he merely playing a role now that he’d observed, or had his entire personality been a facade? Was his desperately horny man-brain pulling the strings and making him say things he normally would not have? Why was it turning her on so much to be objectified, helplessly waiting for him to take the next liberty with her exposed body.
Olivia nearly yelped as she felt his burning hot skin prod her naked ass cheek. “Matt… Please, no touching…” She begged him, realizing she had no idea how far he would try and push the encounter. He grumbled dismissively, and she could feel him rubbing the swollen head of his dick against her shapely bottom while he stroked the long shaft. His movements became more frantic, pushing into her and threatening her balance as he slathered her ass in slimy precum. His free hand shot out and grabbed her hip, steadying her as he continued his assault.
The vulnerable girlfriend’s breathing became heavier as Matt firmly held her in place while he tainted her creamy flesh with his mess. She felt his fingernails dig into her as he clutched her with more and more neediness. She clenched her eyes shut, trying to block out her senses and imagine she was elsewhere. Olivia detested the way her body was responding to the perverted situation, and a battle to win control over the vile urges was raging in her mind. She feared the man would discover just how damp her pussy had become, and take it as a sign of complacency.
As if he’d discovered her attempt to mentally distance herself, Matt abruptly twisted her, spinning her back around to face him and his lewd intentions. He took another step forward, pinning her against the wall. Though the younger man was only a few inches taller than her, she now felt as if he towered over her petite frame. He once again subjected her to his bulbous tip, smearing his liquid desire all over her bare midriff as he pumped his meat. He leaned in, his face dipping towards her barely protected chest, and his free hand soon followed. Olivia shivered as his fingers brushed her bikini top. “Please don’t,” she repeated the simple plea in vain as he pulled the fabric from her luscious breasts, practically drooling as they fell out into the open.
Matt inspected her soft naked curves with wonderment, jerking his cock with a renewed enthusiasm as the image of the deliciously full orbs of flesh burned into his brain. He knew he wouldn’t last much longer, and had enough sense to finish before they were caught, smiling wickedly to himself at the thought of future encounters with the enchanting woman. “Oh my God, they’re fucking perfect…” He mumbled. He’d seen countless tits online, but never before in person, and his tutor had exactly the sort of pair that he preferred. They stood proudly on her chest, ample, yet perky, and filled out her slender frame beautifully. “Just a little touch…” He squeezed at one, admiring the texture and pillowy quality. The pink nipples were small, but stiff, and he pinched one between his fingers.
Olivia chewed at her bottom lip as her tutee explored her exposed breasts. He touched her awkwardly, his inexperience apparent in the way he groped her. The forbidden nature of his caressing was hot though, and her struggle to suppress her instinctive reactions was far from over. As he began grazing her sensitive nipples, Olivia felt a fresh wave of arousal grace her pussy. When he firmly pinched one of the rigid buds, she was unable to stifle her body’s response. “Ohhh…” The light moan slipped out of her lips before she could swallow it, and the shame that followed reddened her already flush face further.
“Mmm… That little moan was so hot. So you like this?” He pinched her nipple again, relishing in the girlish whimper that she failed to completely choke down. He squeezed her tits in his palm roughly, alternating between the two. “Nngh. I think these are my new favorite things,” he said admiringly, his voice strained as he drew closer to his peak.
Olivia was dripping with arousal as he manhandled her, the unique mix of humiliation and physical stimulation driving her senses out of control. She felt the wetness he was spreading across her belly becoming thicker, and wondered how he was able to produce so much pre-ejaculate. She hoped it was a sign of him nearing his orgasm. Every second they spent in that room was an increased risk that Daniel would discover them, or that Matt would move on to the next logical step and remove her bottoms. If he touched her pussy he would know instantly how horny he was making her, and there was no telling what he’d do after that. She had to get out of there before it was too late. “Matt, please finish.”
“Ohh fuck. You want me to cum?” He asked raggedly, his fist lightly slapping into her stomach as he worked himself to completion.
She knew the encouragement could be misinterpreted, but she didn’t have the time to qualify her intention. She just needed it all to be over with, and mirrored his words. “Yes. Please cum. Cum for me,” there was a slight edge of seduction in her tone, a subconscious choice to coax him over the edge by any means possible.
“Nnnyeahh… I’m gonna fucking cum so hard… You wanna see it?” Matt was right on the edge, more worked up than ever before. His brother’s sultry girlfriend was his sole focus, and the walls around her seemed to darken.
“Mhmm, please. Do it. I wanna see it,” she cooed, again feeling very much not herself, saying anything to bring an end to the vile act. Her support seemed to do the trick though, and she watched him tense up, groaning deeply and swaying with a handful of her tit. Is he going to turn away, or grab a tissue or something?
A sharp jet of semen splattered against her tummy, and she jumped in surprise at the unforeseen sensation. Several equally powerful blasts hit her again as she realized he was holding her in place and his aim was intentional. She thrust her hips forward and looked down to witness the explosive eruption that was coating her midsection with sticky white goo. The young man’s enormous cock twitched violently as it spurted rope after rope of pent up seed directly at her bare skin. “Oh my God!” She exclaimed breathlessly, glancing up at his face in disbelief. He was too in the moment to acknowledge her reaction, his drooping eyelids and slack jaw indicative of the overwhelming pleasure coursing through him. For at least half a minute she stood in place, squirming slightly as each fresh stream made contact, and completely awestruck by the sheer volume he was unloading onto her. Her outward expression was one of disgust, but some primal part of her was incredibly turned on by the display of virile masculinity.
By the time Matt’s torrential release had waned to the last few drops, Olivia’s abdomen was absolutely plastered in his viscous cum, and much of it had dribbled down past her swim bottoms and to her thighs. He finally let go of her and looked her up and down, still very much in a daze, his lips curled up in a satisfied grin. The sight of his cum-covered tutor was something out of his deepest fantasies, and he couldn’t believe she was actually standing there. If only I could keep you in my bedroom forever, I would never need porn again.
Olivia was still in shock, the lewd feeling of Matt’s globs of seed slowly rolling down her skin completely new to her. Daniel had never ejaculated on her, and the few times she had given him a blowjob, she’d managed to catch his semen on her tongue before spitting it out into a tissue, never considering the volume could differ. The load coating her now, in contrast, seemed completely unmanageable, like it was a different substance altogether. She felt filthy and degraded, but also immensely horny at that moment. Olivia tried to bury the feeling, as it was in direct conflict with all her morals and beliefs surrounding what had just occurred; but there was no denying that being subjected to that massive angry cock and its uncontrollable need to claim her in such a depraved fashion was extremely hot. Her leaking pussy was craving attention, but she had just enough control to ignore it for the time being. The tantalizing thought crossed her mind that she could still duck into a bathroom to relieve herself.
BZZZ BZZZ.
The notification pulled both of their lofty consciousnesses back down to Earth, and Olivia reached down to pick up her device that had been dropped at some point. She hastily inspected the screen to find two texts from Daniel, the first of which was the fateful message that had ruined her hiding spot.
Did you find it ok?
Where tf are you?
She frantically tapped at her screen to reply.
Sorry, I have a stomach ache, and I had to go find a different bathroom. You still in the tub?
Olivia’s heart was racing as she waited for him to respond. If he had already searched around the house for her, she was in big trouble. “No, no, no…”
“Is it Dan?” Matt asked, offering his glazed muse a paper towel roll. It was in his best interest that she wasn’t caught, as that would surely spoil the potential for any future encounters, in addition to the fact that his brother would likely murder him. She ignored him, her attention fixed on the screen in her trembling hand. Finally, the text appeared.
Just getting out. Aw, sorry you feel sick.
I’m ok. Be back soon.
“He’s coming back inside right now. Can you make sure the coast is clear to the bathroom down the hall?” Olivia shot the man a quick, serious glance as she messily smeared his thick wads of semen from her body, heedlessly dropping each sheet of absorbent paper as it became fully saturated in the slimy substance. Matt cracked the bedroom door open and surveilled while she grabbed her towel from the floor of the closet.
“It’s clear,” Matt said with hushed urgency, unable to suppress his grin as she slipped past him through the narrow entrance, their bodies brushing together one last time. He continued to watch her as she scurried down the hall and disappeared into the bathroom. As satisfied as he was for finally having his first sexual experience, the hunger within him would only intensify now that he’d had a small taste.
****** To be continued…
Comments
NightSoulvane
Nice story so far I appreciate that you've done a bit more character building this time around. You've kind of flipped the script from TRA in that the well built muscular guy isn't hung like a horse. Admittedly it's a little awkward if she ends up leaving Daniel for the brother though. As I read it Matt comes off with kind of creeper vibes. I'd say I'm rooting for Daniel but honestly it's not really that kind of story like TRA was in my mind even after the Josh reveal.
