The Great Hand Job of '06

Levi Summers

Levi felt very self-conscious as Olivia stared expressionlessly at his exposed member. He had no idea what was going on in her head, and it was filling him with apprehension. He kept anticipating her to get angry or burst out laughing. The reality that she wasn't doing either made him more anxious from the suspense.

As for what Olivia was pondering, she could have been more impressed by it, though she wasn't unimpressed either. The woman had expected it to be smaller due to his lanky body, but its length was pretty typical. More noticeably, its thickness was above average.

Letting out a soft sigh through her nose, Olivia popped her knuckles, flexed her fingers, and cracked her neck with a simple head turn, all of which were instinctive motions she did when she was about to dive into a fight. She then wordlessly went to her knees and leaned towards Levi, making the young man reflexively scoot back in his chair as if worried she was coming in to attack him. In response, she flashed him a glare that silently told him to stay put, to which he nodded and did his best to remain stationary.

After taking another moment to sigh once more, she extended her hand and allowed the tips of her fingers onto his shaft.

BONUS: First to Touch Masters Dick: +5 VP

Levi shuddered, a motion that the woman felt between her fingers but didn't comment on.

'Let's get this over with,' she thought.

Levi struggled to hold in a moan as Olivia made the first move, repeatedly sliding her fingers from the tip to the base.

There was no loving passion in her strokes. She didn't bother to look at Levi's face or consider how he felt. She was here to get a job done, and the fact that Levi was required to be part of it was an afterthought. He might as well be an inanimate engine she had to get working.

Of course, the lack of tenderness wasn't due to inexperience on her part. Nor did she feel any shame giving a consenting stranger a handjob, having done plenty of one-night stands in her life. It was just that, despite her intentions, she couldn't overlook that she was only doing this out of necessity rather than choice, which didn't exactly stir up her fiery side. In other words, she was under no illusions that this was anything more than a required chore.

Of course, Levi would have never known she was half-assing it. To him, this was the most passionate experience of his life. Sure, he had previously touched himself, but having it done by another was entirely foreign to him. All his body knew was that it loved it. His hips instinctively thrust back and forth mere inches in rhythm with Olivia while also clenching his toes to the silent rhythm.

It was here that Olivia shook it up by literally adding a twist to her pumping, letting his erection rotate between her grasp.

He couldn't help but wheeze, the tiny extra movement elevating the experience to new heights. Had it not been for the "Your Body Will Know What To Do" boon he received at the start of the show, he would never have had the experience or endurance to avoid going over the edge already.

'He sure is easy to please,' Olivia thought as she glanced up at his expression, briefly acknowledging that the dick she had tasked herself with belonged to a person.

Azure

The redheaded host had an enormous grin plastered on her face as her eyes were glued to the live feed of Olivia jerking off her master. The camera angles shifted as she went, constantly swapping between closeups, wide shots, and whatever was required to give the most titillating exhibition. The host and her enslaved editor knew that this was a moment many fans had been waiting for, and they were dedicated to not disappoint. Azure couldn't help but chuckle at the thought of how Levi might react if he knew the thousand of viewers who were masturbating in time with the handjob he was receiving.

"Alison, I think I'm in love," the host said to her blue-haired assistant, standing behind Azure, watching the show with her signature indifference.

"That would be unprofessional favoritism considering your hosting duties," Alison replied.

"It's a figure of speech," Azure sighed. "She's finally starting to get Levi to understand his role. She's practically doing my job for me."

"You must be very proud," the maid responded unenthusiastically.

Azure ignored the obvious sarcasm. "I am. In fact, I'd better start thinking of what name to give when she's awarded with her new title."

Alison glanced over at her. "Yes, you mentioned they'd get a title change when they first made the master orgasm." She then looked over at the scoreboard on a smaller monitor, specifically the subtitles each contestant had been given. "But I still fail to see why you call that a reward. It doesn't impact the rankings at all."

"You need to understand showmanship. The title change is a badge of honor, showing they've taken the first steps away from their old life and towards their new ones as Levi's property."

She began typing on her keyboard without looking, not wanting to take her eyes off the live footage. "Let's see, what did Kaitlyn call her?" she asked herself. "Oh yes, I remember. 'Dommy Mommy' sounds appropriate."

"Very creative mistress."

Azure waved her hand dismissively. "Mock me all you like. Unlike you, she actually exceeded my expectations." She then laughed. "Maybe I should give her your position."

The maid said nothing, knowing it was an empty threat and would be unattainable even if it weren't. Seeing that Alison wasn't taking the bait, the host continued.

"In all seriousness, this is a significant breakthrough. At this rate, it won't be long until Levi loses his virginity."

The most minor, microscopic change in expression fell on Alison's face towards something that might be considered confusion. She squinted at the monitor, which gave an in-depth closeup of Olivia's hand sliding along the precum moist shaft.

"It would seem that has already been accomplished," she said dryly.

Azure rolled her eyes. "Don't be silly. They might be adjacent to one another, but handjobs aren't sex," she explained as if this was something everyone knew.

"I fail to see the difference."

Azure chuckled. "Of course you wouldn't. You don't even have a pussy, Mrs. Barbie doll."

Alison finally tore her eyes from the screen and towards Azure. "It's fascinating that your quest to find defects in me grows ever more specific."

Olivia Booker

'He sure lasts a long time. Is this boy really a virgin?' Olivia thought, having expected him to cum over five minutes ago. He constantly looked like he was right on the edge but kept finding the strength to hold on.

All she had to do was increase her tempo the slimmest bit to tear his final wall down. He could feel his entire body tense up before experiencing the sensation of his whole essence concentrating within the tip of his penis before...

"Ahhhhgg!!!"

...he fired everything, his cum shooting out from between Olivia's hands, splashing right onto her shirt.

Handjob: +8 VP

Minimal Passion: -4 VP

Bonus: First to Make the Master Cum: +5 VP

Title Change: The Ball Buster => Levi's Dommy Mommy

A soothing calm and exhaustion rolled over him with a heavenly afterglow. It was really sinking in. A woman, an actual woman, had just given him a handjob. Regardless of circumstance, he had never imagined this day would come. He had always rejected such a daydream as too unrealistic; the idea that anyone actually wanted him seemed laughable.

Olivia, of course, wasn't paying attention to Levi. Instead, her first instinct was to look, not at her semen-stained shirt, but instead toward her arms. Any moment now, she was expecting them to bulge to their former glory. But after thirty unchanging seconds, she swore under her breath.

"Shit, that doesn't count, then? Fucking damn it.."

She got to her feet and looked down at Levi, examining the aftermath of what she had given him. She was unsure exactly what to say. Usually, her partners would express something afterward, but Levi seemed so blissed out that she wasn't sure he was even aware of where he was.

'God, he really IS easy to please.'

She briefly considered taking this moment to remove her own pants and fucking him in earnest right now. 'Surely vaginal penetration would count,' she thought. 'Otherwise, this was all a waste of time.'

She stopped herself at this. The woman had been focusing so much on regaining her strength that she had momentarily ignored the other reason she had done this. The points.

Like every other room in this castle, there was an electronic scoreboard. Instantly locating it tucked away in a corner, Olivia observed the shift in score her actions had caused.

Her eye twitched in irritation at the new subtitle she had been given. The Dom part didn't bother her as much as the insinuation of her being Levi's. Still, she was mature enough to not let Azure's childish name-calling get to her. Instead, what was more significant was her score, which went from zero to nineteen, placing her in first place.

'That many from just a handjob? This might be easier than I expected,' she pondered, oblivious that three-quarters of her points had been one-time bonuses.

She looked down at Levi, wondering if she could go another round with him and get 100 points in a single day. However, she quickly reconsidered. Though he was starting to regain awareness, he was clearly too spent to go into another, even more intense session.

"You're, uh, dripping," Levi said, snapping her out of her inner monologue. She looked down to see that the semen he had painted her with was starting to run down her shirt.

"I'll get a towel," she replied, gesturing at Levi's wet dick as well, though she was more concerned about herself, not wanting the substance to reach her leather pants.

"Oh," a third voice chimed up, startling the other two. Two post-sex adults snapped their eyes over to the entrance to see Kaitlyn. The cheerleader's eyes were wide with surprise, but this emotion didn't reach the rest of her blank face.

Levi yelped in embarrassment and reached down for his pants. Meanwhile, Olivia gave the girl a confrontational look as if daring her to criticize.

Deafening silence filled the air, only broken by the shuffling of Levi as he pulled and ripped up his pants. The young man felt trapped in a Mexican standoff of social awkwardness, fearing who would make the first move.

Kaitlyn sighed as the initial shock wore off. It made sense that someone would get to him first, and though she hadn't expected Olivia, she didn't intend to dwell on it. She wished to simply talk to Levi as she had planned, without commenting on what she walked into.

At least, that was what she wanted to do. Unfortunately, her mouth declared, "Hey, you two! Room for one more?"

She closed her eyes in annoyance but didn't express the same humiliation she had shown even a few hours ago. She was frankly too over it to care.

"I meant to say that we are having a pool party at 1 PM. You will be coming, Levi." Her tone clearly showed that this was not a request but an order.

"Ok," Levi nodded.

The Peterson sister rolled her eyes. "I don't care if you don't want to. You're going to-." Kaitlyn stopped herself at the realization of what Levi had just said. She had fully expected to fight him for it and had even prepared a tirade. "Well, good then," she nodded before getting awkwardly silent.

Olivia smirked, knowing what the cheerleader was thinking from her reaction. 'Looks like I beat her to it,' she thought, going to the tea table. The MMA fighter spotted some particularly fancy napkins with the Harem Hotel logo in golden leaf lettering. However, Olivia could not give any less of a fuck, and she used the classy napkins to clean her shirt like they were cheap tissue.

Kailyn cleared her throat. "We'll have lunch as well," she told Levi.

"Ok," Levi repeated.

Kaitlyn nodded once more. She turned to leave before a thought occurred to her: 'Don't give them a reason to punish you.'

She turned around and marched towards Levi, filling him with an instinctive desire to flee. But Kaitlyn was right on top of him before he could get up. She reached out her hands towards his face, making him cry out, fearing she was about to strangle him.

But, instead, she wrapped her arms around his head instead and pulled his face towards her.

Smooch: +3 VP

BONUS: The Masters First Kiss: + 4VP

BONUS IMAGE