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The Tutor's Descent Ch. 04 - Preview 1
🕑 Added 2025-04-04 22:47:14 +0000 UTC**
Update 4/10/25 - A new version of this preview is included in my more recent post, so feel free to skip this one and read that instead.
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This chapter is heating up for sure. I don't love posting a preview with such an abrupt ending in the middle of a scene, but at the same time, I do want to share what I have before the week is over. Enjoy this sneak peek.
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Olivia showed up right on time for her tutoring appointment, as usual, and as had also become customary, her stomach was in knots while she approached the majestic dwelling. Her motivation to return had once been explained by compassion, and the desire to persevere through hardship in order to be a positive force. While those more honorable reasons were still with her, they were now coupled with more seedy inclinations brewing deep within her. The knowledge that there was a real threat lurking within the walls, waiting to tempt her, lured her in with the promise of a most stimulating excitement.
The moment she entered the study, Matt bounced out of his seat to give her one of his signature inappropriately tight hugs, and Olivia just accepted it. She felt partially defeated, having given up so much ground already thanks to her greedy sexual urges. He pressed his body against hers, and she breathed deeply, calming her nerves as her soft chest flattened upon his. The unspoken mutual understanding of what had occurred the previous night hung heavily in the air, but neither of them acknowledged it for the time being. As always, his big cock began to swell immediately until its hardness was impossible to ignore, but she waited in silence for him to finish. It was just a hug, and it would be over with soon so they could get on with why she was there. He did not end the embrace within his already unorthodox time frame though, his arms firmly wrapped around her and applying pressure to the middle of her back.
The sensation of his rapidly growing erection on her lower belly was already beginning to turn her on. Though it was covered and out of sight, she knew exactly what it looked like, and exactly what it wanted from her. Olivia let out the smallest wince as her pupil started moving against her, his hips just barely thrusting to create friction. A sudden awareness that she might be in more danger than she’d anticipated started to set in. She shouldn’t have stepped into his lair that morning. She shouldn’t have done a lot of things. Her voice was dry and cracked as she spoke, “M-Matt. You can let go of me now.”
He ignored her, opting instead to squeeze her more tightly and help himself to a generous sniff of her hair. Her alluring aroma only served as further encouragement, and he subjected her to more of his aching cock. Olivia squirmed against him like a helpless fly caught in a trap as he dry humped her, her whole delicious being his for the time being. “Just… Let me…” He groaned in her ear.
“Seriously. You can’t do this.” She tried to reason with him, knowing full well her defenses were crumbling as his persistence deepened the growing wetness between her thighs.
“I need it. Just help me get me off and I’ll be your good obedient student again…”
“Matt, I–”
“Stop resisting it. I just need to cum.”
Olivia didn’t know what to do. Scream for help? Try to fight him? Maybe, but what would happen after that? Both options seemed too risky without careful consideration, given the rich history between them. She felt responsible for allowing the dynamic to reach this boiling point, and part of her knew there was likely no getting out of it now. She had fucked up in a major way, and now she had to deal with the consequences of her actions. “Okay, okay. Uh… Just go sit over there and finish, and I’ll wait… Like last time…” She stammered, hoping the directed consent would appease him and put her out of harm’s way.
“No. This time you’re going to help me.” Matt momentarily removed one of his limbs from her torso and created just enough distance to fish his manhood out from his shorts. He then roughly took her hand in his and placed it directly on his throbbing cock. The heat of it filled her palm as she automatically wrapped her fingers around the shaft. The helplessness she felt was almost overwhelming, and she dropped her chin in defeat, catching an eye-full of the thick veiny meat dwarfing her slender hand. “That’s it. Just play with it a little. I promise it won’t take long, and then we’ll go back to normal. No one will ever hear about this, I swear.”
She tried to withdraw her hand, but he held it still. She couldn’t bring herself to physically oppose him any further, and the longer she experienced the enticing sensation of his velvety hardness against her skin, the less threatening it became. “This is wrong on so many levels…” Despite her protest, Olivia’s soft grip lightly glided along the rippled skin all the way down to the root. It was her first time getting a feel of his full length so intimately, and she was not surprised by how foreign it felt.
“Don’t act like you’re not into this,” Matt said accusingly. Her blue eyes glared back at him defiantly. “Your secret’s safe with me,” he added through a mischievous grin.
Olivia felt as if she might suffocate in a cloud of shame, his gaze piercing her private struggles. There was no hiding from the fact that her “repulsion” towards his dirty text messages was less than genuine. She’d participated for too long, and continued to read and respond to each explicit word that was sent her way. She was trapped and exposed, at a loss for how to proceed. Would giving in actually be the easiest path forward? Was she seriously considering it? “You don’t know anything… If I do this, it’s only because you’re making me,” she replied, trying to gain back some semblance of dignity.
“Whatever you say,” he replied, reminding himself to stay calm even though his heart was threatening to burst from excitement. He could hardly believe it was actually happening – a handjob from fucking Olivia.
The subdued girlfriend stroked the meaty shaft slowly and carefully, acquainting herself with his anatomy. She was still facing him, her hip his prisoner, and his breath tickling her neck. His cock was so long and thick compared to Daniel’s, and she realized that pleasing it was likely going to be quite different, just mechanically speaking. Her angle was awkward, not to mention they were completely unshielded from the doorway a mere foot behind them. “Let’s sit down and get this over with,” she suggested. Matt complied, finally letting go of her and returning to his chair. She was technically free at that moment, nothing stopping her from fleeing to safety, yet she followed him. Olivia had already made her decision.
She sat next to him, in her own chair, and leaned forward, her elbows resting on her knees. Matt slumped into a relaxed position, the limpness of his body juxtaposing his straight, unyielding cock. Olivia gently took him in her fingers again, each digit coiling around his flesh one by one. Her small hand was just barely able to get all the way around, which amazed her. She squeezed, gripping him just below the ridge of the head, earning her a moan. The monstrous organ felt powerful and alive in her hold, and she was shocked that she could actually feel his pulse. She scooted forward in her seat to get better leverage for the task at hand, and noticed that her panties felt soaking wet already.
“I can’t believe I’m doing this…” Olivia muttered under her breath as her lightly closed fist began the long journey down his shaft. She stopped briefly to squeeze the rigid base, and then traveled all the way back up to squeeze the crown.
“Unnghhh fuck…” Matt groaned.
“Shhh. If I hear a single footstep this is over with,” Olivia whispered sternly, before doing another pass with her tender hand. She couldn’t help but smile inwardly at the seemingly profound effect she was having on her pupil. She’d been touching the man’s dick for all of thirty seconds and he looked like the definition of bliss. She pumped him a few more times before it dawned on her that the deed might take too long without any lubrication. Matt, somehow reading her thoughts, responded by leaning forward and drooling a thick strand of saliva, coating his mushroom tip and her knuckles beneath it.
“Ew…” It grossed her out initially to be subjected to his spit, but the filthiness of it stirred the bubbling arousal within her. Soon enough, Matt’s cock was slick, and she was jerking him off at a proper pace, her slender forearm moving rapidly. She paid close attention to his subtle reactions while slightly altering her technique, testing different speeds, grip strengths, and ways in which she handled the sensitive tip. She even involved her second hand, trying out some different patterns she had seen and inventing some of her own. Though Oilvia was hardly experienced, her analytical approach quickly had Matt quivering from overwhelming pleasure.
Her pupil seemed so harmless at that moment, just putty in her hands, but she recalled the aggressive things he had texted her last night. Like when he insisted that she was going to work all of the cum out of him like a “Good girl”. Welp… Here I am… She couldn’t make sense of why such a demeaning thing was such a turn on for her. Being a “Good girl” and pleasuring Matt’s big cock… Behind her boyfriend’s back… It was such an inexcusable, deplorable thing she was doing, and yet it made her want to rip her panties off and assault her aching pussy.
Olivia told herself that it was just an attempt to speed the process along, but the words that spilled out of her mouth were actually a ploy to get him talking dirty again, a shameful callback to her text from the night before. “You like that, you nasty boy?”
Matt’s glazed eyes sharpened a bit at hearing her, and he looked at her hungrily. “Fuck yeah… You’re gonna milk all the cum out of me?”
“If it gets you to focus on anything other than me for five minutes so we can actually get some work done today,” she replied, feigning disinterest.
“I think you like the attention,” Matt said impishly.
“Some of us aren’t constantly thinking about sex.”
“Maybe you should think about it more. You’re built like a fucking sex goddess–Fuck that feels good…”
“Oh shut it,” she muttered, suppressing a grin at his complement. “Are you close yet?” His slippery cock was throbbing in her hand and spewing more precum as she jerked it, but she couldn’t quite gauge the progress. Handling his huge dick was nothing like she’d experienced before.
“I’m getting there… You could make it go faster if you take your top off…”
“No way. Don’t push your luck–Hey!”
Matt didn’t wait for her approval, and reached over to pull down the loose neckline of her blouse. “Just a peek. To let them breathe a little…”
To be continued...
Comments
Taco
Olivia is such a sexy little minx. Love the slow burn
Yosh
Blueballed again lmao
