The College Bet Ch 02

***

Jack

Although he had his sister under his control, Jack couldn't help but be bummed out by his texts with Chloe. Evidently, his nerves had been rightly placed. So Jack settled into the only cure for a brief spell of depression: video games.

After playing for several hours, he heard a knock at the door and before he could react, his sister waltzed in wearing a conservative blouse and jeans. Now that Violet thought she had him under control there was no need for trying to tease his primal urges.

"Jack be a good boy and give me an update on my assignment," Violet said. She half-paid attention as she pulled her phone out and texted.

The thing about video games was that it was impossible to pause an online game. So, Jack snapped his fingers and said, "Freeze."

He briefly looked back and saw an unmoving Violet staring at her phone. If only he could keep her as a pretty decoration. At least then she'd be useful. Jack continued his game until it was finished and then shut it off to deal with his sister. A few ideas crossed his mind. Video games did a bit to dull the pain of rejection. But his next plan was going to ease the pain completely.

Jack left the room and gathered a few items. When he returned, he had the music box armed and ready to go. He sat back down and ordered Violet to unfreeze. The music box was already playing and before she could get two words out, her head sunk to her chest. With his sister under his control, Jack gave his new commands revolving around two stacks of paper, one blank and one full of writing. After ensuring his sister understood her instructions he woke her back up. This was going to be fun!

***

Violet

"Yes, Queen Empress Violet."

Her obedient little brother handed her the stack of papers and she saw hours and hours of work for a very well done assignment. And she didn't even have to sleep with a teacher! Hypnosis was the best. Not wanting to deal with her brother any longer than she had to, Violet was about to leave but a second stack of papers caught her attention.

"What is that?" Violet asked.

"None of your business," Jack said. He got up to grab it, but Violet pushed him back.

"Jack, be a good boy and tell me what that is," Violet said, pointing to the other stack of papers.

"Yes, Queen Empress Violet," Jack said. "That is an assignment for one of my classes. I'm submitting it tomorrow."

"Is that so?" Violet said with a sadistic smile. She still hadn't forgotten the STD prank and sabotaging his grades was completely unnecessary now that she had hypnosis. But what kind of big sister would she be if she let him get away with slut shaming.

"Jack, be a good boy and ask me to review your assignment."

"Yes, Queen Empress Violet," Jack said. He got up and handed her the assignment. "Can you look this over for me? I think it's pretty good, but it could use a second set of eyes. "

Violet grabbed the stack of papers. "It would be my pleasure." With her brother's assignment in hand, she left him alone and headed back to her room to plot her prank.

Lying on her bed, Violet read the title of the assignment:

'The Stepford Program'

The contents of the assignment were appalling. As if a college would ever assign something so sexist. All of Jack's recommendations and conclusions were ridiculous and would never work on any woman, let alone a college-educated woman.

Each page made Violet angrier and angrier, but then an idea crossed her mind. If she carried out the crazy tasks and proved him wrong, not only would his assignment be a failure, but she could expose him as a misogynist. Not that she believed he was one, but if she had to be labeled with an STD, he could get used to his own poisonous, self-inflected label.

With her plan set, Violet turned back to the first task of the program and read the instructions.

'Step 1: Beauty: Before you begin anything, you need to look in the mirror and give an honest assessment of yourself. You need to find your strengths and work with those, whether that be your tits, your ass...'

Violet skipped to the next part. She didn't need to read how to be hot as fuck. That part she could do in her sleep. It was the next part that intrigued her.

"Once your dolled up and beautiful, it's time for Part 1..."

***

Jack

Jack scrolled through Chloe's Instagram page, fantasizing about a girl he may never get with. But her photos were a welcome consolation, especially the beach pics. Unexpectedly, Jack's door slowly opened and Violet walked in.

"Holy fuck," Jack muttered under his breath.

Violet's face was done up like she was going on a sexy date with pouting red lips, blush, and, mascara bedroom eyes. Her body was barely hidden by the tight top pushing her tits up for maximum cleavage, and her bare midriff and thong showcased her wide, child-bearing hips. The black fishnet stockings and impractical high heels completed the uniform. If she hadn't been wearing a white headband or white frilly arm cuffs, Jack would have had no idea that she was masquerading as a maid. As if to further emphasize her beauty, she wore matching diamond earrings and a necklace.

Playing along, Jack kept up the shocked charade.

"Violet, what are you doing?"

"I'm...umm...I just wanted to say thank you for doing my assignment, so in return, I'm going to clean your room."

"Dressed like that?"

Violet looked down at her outfit and her cheeks went red as a tomato.

"I wear stuff like this all the time around the house," Violet said.

"That's true," Jack said. "Well, have fun I guess."

She nodded and then went to work cleaning up his dirty clothes. He could tell by her slow movements and small steps that the heels were going to be a challenge for the entire job. Thinking back to what he had written, he had never specified her to wear such slutty heels, but he had ensured she chose sexiness over functionality. And it worked. Bending over took twice as long, giving Jack ample time to admire her perfect peach. The scene tempted him to whip his cock out right then and there, but he maintained his restraint.

After picking up and handling his clothes, including his dirty underwear, the new maid entered his ensuite to clean his bathroom. To be a fly on the wall inside her mind.

***

Violet

Violet could barely contain her laughter as she walked into the bathroom. As if the little twerp thought his program was working. She was playing her role to perfection and at the last minute she'd expose him for devising such nonsense. And to make matters even more fun, she had worn the sluttiest outfit to tease him.

After cleaning the sink, Violet was about to move on to the toilet, but then Jack entered.

"Sorry, I just need to take a quick piss," Jack said.

Like it was a normal thing to do, Jack moved beside his sister and took his cock out to pee. So surprised by his nonchalant behavior, Violet just stood and stared at his manhood while he urinated. It was bigger than she had expected. Far bigger. In fact, anytime a guy had the size of cock that Jack had, she would brag to everyone to raise his reputation. Her friends deserved a good fuck too.

When Jack was done, he took a piece of toilet paper and wiped the head of his cock then threw it in the toilet and flushed.

"Sometimes the little fucker dribbles in my pants," Jack said while his little fucker stayed out and on display. "So, are you like my maid then?"

Momentarily mesmerized by his crotch, Violet snapped back to the role she was secretly playing.

"Yes, I'm your maid, Jack. All I do is clean, clean, clean," Violet said. She stopped herself before her sarcasm ruined her whole plan.

"So, you plan on cleaning everything in this room, correct?"

"Yep, that's my job," Violet said.

"And because I'm in this room, I'll need to be cleaned then?"

"Umm...well I guess...yes because you are in here, I'm obligated to clean you, if you would like."

This had not been part of her plan, but she couldn't stop so soon after going through the effort of getting dolled up and dressed for the role. Besides, he wouldn't stoop that low.

"Ya, I think I could use a good polish," Jack said.

"Oh," Violet said as Jack's hands guided her to her knees until she was at eye level with his crotch. She looked up with pleading eyes. "You...you want me to clean your cock?"

"It is part of me, isn't it?"

Violet stared ahead at her brother's cock and already regretted her stupid plan. She had hypnotized him and could easily win their bet and yet here she was on her knees about to blow him in the hopes of eventually humiliating him. She closed her eyes and envisioned him being exposed for his assignment. It was all going to be worth it. Besides, it's not like she was unfamiliar with blowing a guy.

"Better get started," Jack said.

Taking a deep breath, Violet grabbed Jack's cock and guided it into her mouth. He looked down and made eye contact while she pleasured him. If he thought he was winning, he had no idea what she was up to. Without saying a word, Jack gently put his hand on the back of her head and rocked it back and forth to clean his cock. Not surprisingly, Violet's mouth was the perfect tool for the job, and she had her brother weak in the knees in no time.

Or so she thought. Violet had a reputation for giving great head, which she did not withhold in her performance on Jack. However, her younger brother seemed immune to her skill. No matter how fast or how much spit and gagging, Jack's stamina proved to be a fierce opponent. Was he going to tell her to stop at some point or was she expected to clean him until the job was finished? After polishing his cock for another ten minutes, Violet believed that she had the answer. It was one of the longest blowjobs she had given, and her jaw was starting to hurt. But she had a duty to uphold. After another few minutes of slurping up her own spit and more of his precum, it became apparent that her mouth was inferior to the task.

Violet popped Jack's cock out and stroked it while she looked up. "I think I need to use another method to clean your cock."

"I personally think you're doing a great job," Jack said with a grin.

"Yes, but you're not getting clean."

"That is true. You have been going at it for a while. What did you have in mind?"

The lubed-up cock was making a mess in Violet's hand. She looked down at her state of dress and momentarily questioned why she was going through so much work. Effort was the last thing she exhibited in any task. Violet had always taken the easy route. And yet here she was playing the long game. If her mouth couldn't clean him, there were only two other options that she could try.

"Well, I think my pussy will be able to get the job done," Violet said.

Jack took a minute to ponder then shrugged his shoulders. "I mean, if that's what you gotta do."

He had no idea that he was setting himself up for failure. After working the logistics out in her mind, Jack stepped in and made a suggestion. Violet followed his orders and got on all fours hovering over the toilet so that her tits dangled between the seat. She felt the cock penetrate her pussy and it fully sunk in that her brother was now fucking her. All those years of teasing him in underwear and bathing suits and lingerie. Now he was finally getting a taste of the holy grail.

As she rocked back and forth on his cock, cleaning it with her pussy, the situation seemed off. Why was she letting him fuck her? What the hell was going on!

***

Jack

"Jack! Jack, what the fuck is going on? Get the fuck off me!"

"You're cleaning my cock, remember?"

Violet turned her head and glared at him. The cramped space next to the toilet made it hard for her to get away, but she started fighting back.

"Freeze," Jack said and snapped his finger.

Violet froze on all fours and stopped moving. Relieved that his freeze command still worked, Jack realized that Violet may have had to jump through a lot of mental hoops to conclude that fucking him was normal. If he was going to successfully utilize hypnosis, he'd have to rethink his triggers.

But in the moment, he wasn't going to ruin the first time he fucked Violet. Having her frozen only added to the unique experience. Jack grabbed her hair, pulled her head back for extra grip, and continued using his new toy. As he fucked her passionately, Jack slapped Violet's ass repeatedly. He enjoyed that he could use her body and not have to hear her annoying little voice.

Whether it was the lack of his extensive sexual history or because he had heard Violet with so many men, her pussy was tighter than he had expected. And as fun as fucking his frozen sister started, the image of her small frame vibrating under each of his thrusts combined with the warm sensation gripping his cock, Jack had his cock cleaned in no time.

***

Violet

The first sensation Violet felt was the stinging on her ass and then a warm wet sensation in her panties. This was surprising because the two balls in her mouth brought her focus back to the task at hand. Her memory was foggy for a few seconds then everything became clear. Violet had cleaned Jack's cock and she was now working on his balls so that he could be on his way. Then she would continue her mission of humiliating him by disproving his paper.

Jack held his cock up as Violet took his balls in her mouth and swirled them around for a good wash. Who knew cleaning a man was so much effort? When Jack was satisfied, he pulled his sack out, dragged it up her face, and then put his cock away.

"Looks like you're all clean," Violet said.

"Actually, I think there's one more thing, I need you to cleanse," Jack said. This time he unzipped and pulled down his pants and underwear. He turned around, bent over, and spread his cheeks with his hands. "Just a quick scrub."

If the world had any true opposites, it was a man's ass and a woman's face. One was perfectly prepared, polished, and beautiful. The other was unkempt, ugly, and chaotic. On principle, Violet had always rejected the act of a rimjob even from the most dominant partner. Why would she debase herself and her beauty for an act that brought her no pleasure? Usually, she turned the request around and had the man eating her out in no time.

But that was not an option here. She was the maid, and she was responsible for cleaning.

"It looks pretty clean to me," Violet said.

"Pretty ain't clean."

If she stopped now, cleaning his cock and balls would have been for nothing. She had to continue. Violet got on all fours and crawled towards her brother's ass. It was outrageous that her perfect pouty lips had to touch such a thing. She suctioned onto his ass cheeks and plunged her tongue forward into Jack's asshole. Her tongue branched both ways, licking whatever she came in contact with. The stench was unbearable, the taste was overwhelming, and the pleasure was...

"Ohhh, ahhhhh...."

The orgasm overtook Violet's mind as her body convulsed beneath her. The more she licked the more her pussy vibrated with good feelings. Expecting the euphoria to pass, Violet lost herself in the task at hand, happily burying her face into Jack's ass. Her spit and saliva built up around her mouth as slight patches of makeup were left behind on Jack's cheeks. It was demeaning and Violet wanted to stop, but orgasm after orgasm kept her hungry for more.

It was only when Jack finally pulled away that Violet's world came crashing down with a final orgasm that left her blissfully screaming on the floor. Her brother stood up and looked down at her, content with her service.

"It looks like I'm all clean," Jack said and then left without further comment.

Violet sat up and immediately felt the state of her face and mouth. It was embarrassing, but not as embarrassing as Jack was going to be when she exposed him. She stood up and continued working in her current condition including the taste of Jack swirling around in her mouth as a constant reminder. With her maidly duties almost finished, she'd soon be onto the next step in the program and one step closer to completing her plan!

***

Jack

Sitting on the couch and watching television, Jack ran through the day so far in his mind. He had Violet right where he wanted her and yet there was a constant pull within him to forget the whole charade and just work on turning Violet into his little sexy slave. But he withheld that temptation. Partly because he didn't want to risk breaking the trance completely and also because watching her logically agree with his reasoning was entertaining within itself.

Although fucking Violet had been his favorite moment, he couldn't stop replaying the image of her on her knees, her cute face buried deep in his ass. Maybe next time they were in a heated argument, he'd create a trigger that would have her on her knees, tongue deep in his ass in no time. He'd never lose an argument!

The clack of the heels coming from the kitchen caught Jack's attention as his sister emerged from the doorway. The maid uniform was long gone and had been replaced by a red and white polka-dot apron that wrapped around her shoulders and waist. Her tits were pulled over the apron and hung down like two supple udders. Violet's hair was done up into a perfectly tight bun and her make-up was once again flawless. To Jack's further surprise, Violet wore what looked like their mother's old diamond wedding ring on her left ring finger.

Carrying a plated sandwich and a beer, Violet walked over to Jack. "Your sandwich and a beer, honey," Violet said in a cute innocent voice then giggled. She knelt beside him and held the plate and beer for his convenience.

Jack took a bite of his sandwich and was starting to get used to being pampered like a king. But how long before Violet's mind figured out what was really going on?

***

Violet

Kneeling at her brother's feet dressed like a housewife, smiling and holding his beer and homecooked food was almost as humiliating as eating his ass. But at least that had a weirdly powerful physical side effect. Being a human table did not have the same result.

However, it was part of the duty of being a housewife. Violet had already completed the maid training and had no urge to put the uniform back on. So, it stood to reason that Jack's paper was indeed bullshit. And after Violet made it through all the programs, she'd have the evidence to prove it.

So, she waited with her tits out like a piece of beautiful furniture while Jack slowly ate his sandwich and drank his beer. Before Violet had decided to see her mission through to the end, she had many plans for the evening lined up. Instead of attending one of the biggest college parties, one which Jack was not invited to, Violet was attending to her brother's needs. The trade-off sucked, but Violet was determined to prove him wrong.

When Jack was done, Violet took the empty beer can and plate back to the kitchen. She grabbed the sandwich that she had made for herself from the fridge and sat down at the table to eat it. Before she took the first bite, Jack walked in.

"I think you're missing an ingredient on that," Jack said.

"And what ingredient would that be?" Violet asked trying her best to not seem annoyed.

"Man gravy," Jack said. He walked over and stood next to her plate with his hands in his pockets. "And you're lucky. I've got the best source."

Did he really think this was going to work? But then Violet remembered that her duty as a housewife was to listen to her man. If Jack said she was missing an ingredient, then she was missing an ingredient.

Reluctantly, Violet unzipped her brother's pants and pulled out his cock. Like she was getting ready to use any other condiment, Violet stroked Jack's manhood casually, aiming it at her sandwich.

"So, are you and Chloe like a thing?" Violet asked.