The Tutor's Descent Ch. 05 - Preview 2

Hey all, this next chunk of chapter 5 contains a lot of set up, but as I'm sure you can imagine, everything is in place for a spicy follow up. Stay tuned!

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After taking care of her needs more than a few times with Matt’s pungent scent on her, Olivia scrubbed off and set out to carry on with the rest of her day. She had plans to meet up with her new friend Hannah at the campus coffee shop and dig into some homework. The girls had been teaming up regularly for the past few weeks, finding they could get a lot more done when they put their heads together.

“Oooh, he’s cute,” Hannah said quietly, looking over her classmate’s shoulder at one point. Olivia shot a quick, subtle glance behind her to see the young stranger that had just entered the venue. “Don’t look now!” Hannah urged with a stern whisper, causing them both to giggle. It was commonplace for their conversations to end up on the subject of guys and dating. Besides Matt, Hannah was the only person Olivia knew that had even less experience than her, and she came off borderline obsessed with the topic at times.

“Are you gonna say ‘Hi’ this time?” Olivia asked, lightly teasing her extremely shy friend.

“No! I… Not right now… We’re too busy with this,” the woman stammered nervously, her glasses slipping down her nose as her face buried itself into her text book.

Olivia smiled at her jittery study buddy. “You know you have to put yourself out there a little if you want to find someone.”

“I know, I know…”

An idea suddenly occurred to Olivia, and she was surprised that the thought had not come to her before. Could it be possible to somehow bring Matt and Hannah together? It would kill two birds with one stone, but was it the right move? She knew too much about Matt’s insidious side, and wondered if putting her innocent friend in his crosshairs would be a disservice to her. Then again, his behaviors had just been motivated by the need for sex and companionship, as far she could tell, and Hannah had also been quite preoccupied with the same desires. They were both socially awkward virgins, and they were both lacking many of the same experiences. The more she thought about it, the more it seemed like a reasonable solution.

“I might know a guy who is looking for a girlfriend…” Olivia spat out the suggestion, still uncomfortable with the notion of integrating her boyfriend’s problematic brother into her friend’s life. 

Hannah perked up immediately, staring across the table with anticipation to hear more. “Really?”

“Yeah, maybe…”

“Details please!”

“Uhhh. Well, Daniel’s little brother is single…”

“Daniel’s brother!? The one you’re tutoring? Does he look like Daniel?” She was clearly excited about the prospect, and had never made much of an effort to hide the fact that she found Olivia’s boyfriend exceptionally attractive.

“Not really. But I suppose he’s kinda cute in his own way,” Olivia explained, already regretting bringing it up.

“Got a picture?”

“Um, I don’t think so.” Other than a few pictures of his cock, she thought. “Hmm, are you free Saturday night? There’s a big halloween party at Daniel’s buddy’s house. Maybe we could all meet there. That way if it gets awkward it’s not just a one on one thing or whatever.”

Hannah looked hesitant. “A real college party eh? I don’t really go to those…”

“First time for everything,” Olivia encouraged with a smile, hiding the fact that she was equally nervous about the whole thing. “They can be a little wild, but I’ll be there to look after you.” She’d suddenly began orchestrating the plan with little to no idea how it would turn out. Would Matt and Hannah even hit it off? Would he try something unsavory with her that would ruin their friendship? How would her boyfriend feel about the fact that she was inviting his brother without asking? Surely, he was going to be pissed. She’d have to find a way to get in front of that and let him know so that he wasn’t blindsided by it. There were a lot of moving pieces, and the stress began setting in as she contemplated all of the possibilities.

“Olivia?” Hannah waved her hand over her classmate’s glazed over eyes, snapping her out of her frantic thinking.

“Huh?” 

“I asked if you have a costume yet. I haven’t dressed up for Halloween since I was like, twelve,” Hannah explained.

“Ha, perfect, I still need to pick one out too. Let’s go right now!”

The women were in agreement, and headed to a nearby costume shop to select their outfits for the upcoming party. After a bit of browsing the many aisles, it was becoming clear that Hannah was gravitating towards the “sexier” options, likely eager to use the unique opportunity to break out of her shell and to spite her repressed past. Olivia, though normally opting for a more conservative look, got caught up in her friend’s excitement and didn’t want to deny her the opportunity to be bold for once, so she encouraged it. After selecting a variety of skimpy costumes targeted at college girls their age, they hit the dressing rooms together to make the final decisions.

Hannah went in first, leaving Olivia alone with her thoughts and the collection of potential party attire in hand. Any one of them would undoubtedly turn heads, and be a little outside of her comfort zone. But that’s what Halloween is for, right? She reasoned that most girls would be dawning similar costumes, and that Daniel would probably be into it. Not to mention Matt… 

The olive-skinned, reserved girl reemerged shortly in a bright red, skin-tight halter top dress with devil horns. “This feels completely wrong…” She muttered unconfidently.

“Wow! You look hot as hell!” Olivia encouraged, genuinely shocked at the curvy figure Hannah had been hiding under her frumpy hoodies. Her breasts were on the smaller side, but still provided a decent amount of cleavage which was assisted by the low cut dress that propped them up nicely. Her narrow waist gave way to wide hips, and the silky material hugged her body perfectly.

Hannah’s face quickly matched the color of her costume as she smiled in embarrassment. “Thanks… You don’t think it’s too much?”

“I mean if you’re going for sexy, you nailed it. I think we have a winner already.”

“I think I wanna try the black cat one instead, that feels more me,” Hannah said.

“Go for it!” Olivia exclaimed, waiting as the woman shuffled back into the cramped room. A minute later, the slatted door opened to reveal a very different looking Hannah. Her skin was now tightly wrapped in multiple pieces of matte black material which barely covered her pelvic region, exposed her tummy, and supported her breasts similarly to the previous attire. Dark thigh highs drew the eyes to her exposed upper thighs, and a furry set of ears completed the revealing outfit. The bashful girl wearing it was grinning from ear to ear.

“I didn’t think you could top the last one, but that looks perfect on you! You make a very sexy kitty.”

“Thanks! I think I’m going with this one for sure,” Hannah giggled, beaming. “Okay, your turn!”

“Alright!” Olivia said, intoxicated by her friend’s jubilant disposition. She rushed into the dressing room and weighed her options. After some internal deliberation, she opted to try on a “Little Red Riding Hood” costume, as it seemed simpler than the others, which involved too many straps and other elements that seemed cumbersome. It was anything but innocent though, the mini-skirt leaving very little to the imagination, and the tiny blouse tied off in the front covered little more than the most private areas of her ample chest. She pulled the silky, red hood over her head and stepped back out into the open to get Hannah’s reaction.

“Oh my God, Olivia. You look… Exquisite…” She admired, practically drooling.

“You think?” Olivia asked, performing a little twirl.

“Hell yes. You have to wear that.”

The scantily clad tutor peered in the mirror again. She had to admit, the outfit did look amazing on her, but it was something she wouldn’t be caught dead in under normal circumstances. She reminded herself that it was just for the party, and that she couldn’t back down now given how brave Hannah was being. “Well I guess that’s settled then,” she said, forcing a smile and earning a cheer from her friend.

The women changed back into their normal clothes and purchased the costumes. “Thanks so much for getting me to do this,” Hannah stated, hugging her, and oblivious to the fact that Olivia was equally pushing the limits of her boundaries. “So Daniel’s brother will be at the party? What’s his name anyway?”

Olivia felt her stomach churn, having nearly forgotten the proposed meeting. “Uh, his name is Matt. I’m not sure yet if he’ll be there, but I’m gonna ask him.”

“Okay! You think he’ll like my costume?”

“I’m pretty damn sure every guy there will,” Olivia answered. Hannah seemed like a perfect candidate to capture Matt’s attention, but she worried that her own presence would cause some complications. The girls said their goodbyes and parted ways, leaving Olivia with the burning question of how she would navigate the upcoming days.

******

“Oh fuck… Yesss, just like that…” Matt cooed as his sultry tutor rapidly jerked his big saliva-coated cock.

“C’mon, cum for me,” Olivia encouraged, having gotten used to uttering such phrases in the throes of their masturbatory sessions. Her pupil had coerced her once again, despite her reservations, which had been recently bolstered by the close encounter with his father. If everything went according to plan, this would be the last time she would have to do this for him.

“Nnnghhh… Yeah… Ask me again,” Matt groaned, rising to his feet and taking his position to empty his heavy balls all over her.

Olivia rolled her eyes, obliging to get it over with. “Gimme that big nasty tribute all over my tits…” Matt moaned deeply, signaling his climax, and his throbbing dick began shooting hot semen at her exposed flesh. Olivia took each thick rope, fighting the urge to touch herself as usual, and milked him for every last drop until he collapsed.

“So what’s my special surprise for passing the test?” He asked lazily through heavy breaths. He had insisted on some form of a unique service, but Olivia had urged him to be patient, explaining that she had something in mind and would let him know at the end of the session.

“First of all, you got a B, mister. Last I checked, that’s not exactly acing,” Olivia teased as she wiped the many globs of pearly white seed from her exposed breasts.

“Close enough!”

“It’s a pretty good score, I’ll give you that… Anyway, your surprise is that I’m inviting you to a super cool Halloween party at my University!” Matt looked slightly underwhelmed. “...And… I found a really cool girl that I’m gonna set you up with.”

“Huh?” Matt felt a sting of disappointment, but was also intrigued.

“Trust me. Tomorrow night. It’s gonna be a big party, and my friend Hannah will be there. She’s super cute, and has been looking for a guy like you. I think this will be a really great opportunity for you. Just give it a shot, okay?” 

“Hmm… Doesn’t sound like my scene. I have to dress up?”

“Well, yeah. Just grab a cheap costume. It doesn’t matter,” Olivia explained. “You're in college too. This is your chance to get out of the house and put some of those new skills we’ve been working on to the test. Who knows, you and Hannah might even end up really liking each other.”

“What does she look like?” Matt asked, worried that this “very available” friend couldn’t possibly measure up to his tutor.

“She’s a little shorter than me, and has a great body. Nice eyes and a nice smile… But she doesn’t even know it. I guess you could say I’ve been helping her open up a little, same as you.”

Matt paused to contemplate as Olivia finished cleaning herself off. A diamond in the rough could be a nice prospect. Even if he didn’t take to this mystery woman, there would probably be lots of hot girls to ogle at the very least. “Does Daniel know I’ll be there?”

“...Yeah. I’ll smooth things over…” Olivia lied, hesitant to give him any more reasons to decline.

“If I go, he better not fuck with me…”

“I’ll keep him out of your hair. Don’t worry. So you’re coming?”

“I’ll think about it.”

******

To be continued...