The College Bet

The only upside of the long boring lecture that threatened to put Jack to sleep was the beautiful teaching assistant, Ava. The slim brunette always looked incredible, and Jack didn't know if it was for the professor or for some of the students. She was outgoing and flirty with everyone, even Jack, which increased his daytime fantasies about her.

"You're starting to drool." Violet, Jack's older sister, said. "Oh, and you might want to hide that hard-on before she returns the tests."

Jack and Violet were the complete opposite in every aspect of life. Violet loved the spotlight, and she was attractive enough to command it. Like Ava, Violet knew how to flirt and how to look good enough to disarm any man's defenses. Even other women weren't safe from her charm. Although Jack had never seen it in person, there were many rumors that Violet had broken up a few relationships by seducing the girl. Knowing his sister, he wouldn't put it past her.

Jack, on the other hand, hated the spotlight. He didn't want to be noticed and preferred to limit group engagements with strangers. But that was impossible with Violet as a sister. She was simply the talk of the college, despite being a few years older than her classmates. After high school, she had traveled for one year on her parent's money and one more year on her wits. When the money had run dry, her father had forced her to go to college before seeing another penny from him. To make Jack's life miserable, she chose his college and the siblings had entered their first year together.

With Jack's cock tucked under his waistband, he glared at his sister. Violet was no stranger to sex and openly teased Jack while they lived together. Walking around nearly naked and openly flirting with her brother were just two of the many things she did daily to make her brother uncomfortable. And like the horny college kid that he was, Jack then used the memories of his sister to jerk off in the shower. It was a secret he'd take to his grave.

Ava walked by and smiled at Jack. "Better luck next time, Jack."

The teaching assistant put the paper down showing a 49%. Jack grabbed it and sank in his seat as he stared at his own failure. Ava put Violet's down and Jack saw the 95%.

"Great job as always, Violet." Ava said. Jack couldn't tell if it was friendly, or flirty, or both.

It was a complete sham that his sister had done better than him. While she had gone out partying and socializing, he had stayed in and studied his ass off. Yet somehow, she had aced the exam. There was no way she was that smart on her own. Violet had a way of building rapport with people and this was no doubt the case with the older professor. Jack liked to believe that a college professor would be prepared for the platoon of whores that would be marching through his classes. But as Jack had experienced personally, some hot girls knew exactly what buttons to push and his sister was one of the best he'd ever seen and a master at her craft.

"Oh, how unfortunate. Mom's going to wonder why you can't be a star student like your genius sister." Violet said.

"Screw you, Violet. You think I don't know you did something with Professor Norton."

"Are you calling me a slut?" Violet said in a mocking tone. "Good luck convincing mom."

Jack didn't respond. There was no point. She could mock him all she wanted, but they both knew he was right and he wasn't going to be baited into arguing with her.

***

The test result soured Jack's mode so much that his confidence was shaken for his plan to ask his longtime best friend, Chloe, out. He knew all about the friendzone, but there was a spark there. Both of them were just afraid to make a move that might jeopardize the whole friendship. Regardless of the result, Jack was sure their friendship would stay the same. That was if he was riding the high of a great test result. Now, all he could do was make excuses for why he had failed and why that meant he couldn't ask Chloe out in his current state of mind.

"Mom's here." Violet said as she walked by her brother's room.

For their first year of college, their mother had insisted that they share a place to live. However, it was starting to become a challenge, especially with Violet's late nights and active sex life. If he had to hear her bed bang his wall one more time, he would go in and knock the guy out. However, there was no way to get out of the living arrangement. For the remainder of the year, he was stuck with his stupid slutty sister.

Jack entered the kitchen to find his mother, Eden, enjoying a coffee with Violet. Like his sister, his mother had been blessed with the genetics of a bombshell. However, unlike his sister, she used less of her influence as a beautiful woman and more of a manly intimidation to convince people to do things her way. Eden obviously felt that relying on sexual behavior was a weakness and she didn't want to fall in that habit. One day she would lose her beauty and where would that leave her?

"Jacky, your sister tells me you failed your test." Eden said.

"I studied my ass off, mom. The only reason she passed is because she fucked the professor."

"Jack Daniels, don't you dare use that kind of language with me." Eden said.

Jack and Violet exchanged looks he rolled his eyes.

"Sorry, mom."

"He just called me a slut." Violet said.

Their mother gestured to Violet's revealing outfit. "I'm not stupid, honey. I know how men work."

"So, she's in trouble?"

"No. Although the goal is to learn at college, the system is already screwed up. So, I don't blame your sister for using her best skills, and I don't want to know what those are." Eden said

There was an awkward silence that Violet eventually broke.

"So mom, tell Jack and I why you're here."

Jack took a seat on the other side of the table. His mother seldomly showed up for visits and when she did, it had always been to relay something. The only time visits weren't for something is when they came home for dinner and that was usually for money related reasons.

"Your father and I were discussing how privileged you two have been growing up and we wanted to give you both an incentive to work a little harder in your first year." Their mother said. "So, what we've decided is that whoever has the highest grade point average by the end of the year will get their own place paid by us next year."

"Holy crap." Violet said.

"And what happens to the loser?" Jack asked.

"We will still cover tuition, but either they live at home, or they find a job to cover their rent."

"This is bullshit." Jack said. "Literally all her professors are men. She's going to fu...bang her way to a house."

"I can't run your sister's life, Jack. If she wants to let creepy old men use her for an arbitrary number that will mean nothing beyond college, then she's going to have to live with those memories."

Jack wasn't sure if that was an insult or compliment to Violet, but his sister took it as confirmation that she had everything she needed at her disposal to win. If there was any hope of winning, then he needed to even the playing field. He needed to start playing dirty. And he knew exactly where to start.

**

Violet lay on her bed filling up her cart on Wayfair. The competition her mother had set up was going to be the easiest thing she would ever win. Her poor brother couldn't catch a break and now he'd have to work even harder next year to make ends meet. There was no way he'd move back into their parent's house because then he could say goodbye to any chance with a girl. Which was weird because he acted so strong-willed and confident with Violet. If only he applied that to other girls, then maybe he'd have as many partners as she has had.

With bedtime coming soon, it was time to taunt her brother and gloat over her impending win. Violet stripped down to her sexy underwear and cat walked into her brother's room.

"So, you think you really got a shot here?" Violet said.

Jack looked up quickly then back down at his phone. Then he did a double take at Violet's sexy body.

"Why don't you save us both the trouble and just come in here naked." Jack said.

"Wouldn't you like that."

"You seem to like showing me your body. I think it gets you off more than it does me."

"Yes, but you're the one that fantasizes about this." Violet said and then motioned down her body.

"In your dreams. You probably get off to me getting off to you." Jack said.

He hopped out of bed and stood face to face with Violet.

"If you want to drop to your knees and suck my cock, just let me know sis." Jack said. "I won't be offended."

Violet knew that whatever psychological game he was playing, it wasn't going to work. Jack was just using his fake bravado to hide how he truly felt. And Violet wanted to prove to him exactly how things really were.

"Like I would ever let you put that gross thing in my mouth."

While maintaining eye contact and without saying a word, Violet reach behind her back and undid her bra. It fell to the floor between them and they continued to make eye contact for another moment. Then, despite his best efforts, Jack became no match for his own sexual urges. He tried to do it discretely, but his eyes bounced back and forth between Violet's eyes and her tits. Soon enough, Violet felt something poke her leg and she stepped back when she realized it was Jack's boner.

"Come on Jack, I'm your sister."

"You literally took your tits out." Jack said. He kicked her bra under his bed. Quickly he lifted his phone and took several pictures before Violet realized what he was doing and covered herself up.

"You delete those you little pervert." Violet said, trying to grab Jack's phone.

Jack pocketed his phone and grabbed Violet, throwing her on the bed. Then he pulled out his phone and took a few more photos of Violet topless on his bed.

"How about you stop trying to taunt me with your body." Jack said. "And maybe I don't send these to mom.'

Violet rolled out of the bed and knelt on the floor. She grabbed her bra from under the bed and quickly put it back on before standing up.

"You wouldn't dare."

"Try me, whore."

Violet gave him the middle finger. Her taunting session had completely backfired and now Jack had some dirt on her.

"Fine, I'll dress normal around the house." Violet said. "But don't you dare use this against me in our bet."

"What's stopping me from doing that?" Jack asked with a smile.

Nothing. Nothing was stopping him from doing that.

"Don't you worry, I'm going to beat you at your own game." Jack said. "I don't need this to win."

Violet didn't know if she could trust him, but she had no other option left. Somehow, she'd get those photos off his phone, but it wasn't going to be when he was focused on them. She had underestimated her brother, a mistake she wouldn't make again.

Backing away from her brother, Violet left the room. There was no way he'd win the bet when she could sleep her way to the best mark. Soon enough she'd have her own place and then she wouldn't have to deal with living with her brother ever again.

**

Jack sat down at his desk and scrolled through the photos of his topless sister. It wasn't his plan to get photos of her, but she had always pushed the envelope of teasing him and it had become the perfect opportunity. Now he had her in all her glory taken by his amazing phone camera. He didn't intend to send the pictures to their mother, although it would be funny to see her scold Violet. However, he could think of other uses for them. If he was going to beat Violet, he would have to play just as dirty as she did.

Turning on his computer and putting on his gamer headset, Jack started up one of the many online games he played with his friends. After several minutes, the gang was back together and playing online.

"Hey Tortoise. You still good at photoshop?..." Jack asked. "Good, because I have a few things I could use your help with."

***

Violet checked herself out in the washroom mirror, flipping her hair and puckering her lips. She was looking extremely delectable and with good reason. Today she was planning another seduction to increase her marks. Despite how easy it sounded to Jack; it was far from a smooth process. Each professor was different and had their own tastes. Some only liked blow jobs, some liked sex and some were into completely different kinks. There had even been a few professors in the past that also paid her money on top of increasing her mark to degrade them. It was fascinating to get a look behind the door of what made men tick and she had learned to never judge a man by his lectures. Even the strictest professors might end up as her little bitch behind closed doors.

The first professor, Mr. Wagstaff, was a familiar face and someone who was already putty in her hands in the brief time she had been at college. She knocked on his door and waited patiently, but in a sexually suggestive pose.

The professor opened the door and instead of playing it cool, he grabbed her and pulled her inside his office, shutting the door behind them.

"What the hell, Paul?" Violet said as she made sure her outfit still looked sexy.

Paul took a sheet of paper from an envelope on his desk and slammed it into Violet's chest.

"When the hell were you going to tell me about this?" Paul asked.

"Tell you about wha..." Violet said. She looked at the sheet and saw that it was a medical report stating that Violet had the clap. "What the fuck? This isn't true. I don't have any STDS."

"I'm getting tested, but we're done." Paul said. "Now get out."

Violet was ushered out with the piece of paper. She had nothing further to use on Paul. Even blackmail wouldn't work because he was a single, young man. Going after his job would only lead to her getting expelled too. Besides, she was not one to stretch the truth. The only option left for his class was the worst one: actually studying.

The medical report in her hand was clearly fake. And Violet knew exactly who the culprit was.

**

Jack was eating his dinner on the couch while watching television, his usual nightly routine. The front door slammed, and Violet stormed in.

"An STD, are you fucking serious?" Violet said.

Jack kept his eyes on the television. "I don't know what you're talking about."

His tone couldn't have been more of a slap in the face. Violet stood in front of the television.

"All my professors won't even entertain me because of that stupid rumor."

"Oh no." Jack said with exaggerated shock. "I guess you'll actually have to study for once. What a shame."

"Fuck you, Jack." Violet said.

She rushed to her room and shut the door behind her. It was going to be a miserable night for her. But not for Jack. Riding the high of seeing his plan work, he had finally decided to tell Chloe how he felt through a text. And then, when they became a couple and he won his new condo, everything would be perfect. His plan was all coming together.

**

Violet sank into her chair. For years she had tried to use her sexuality to influence Jack like everyone else she had encountered, but somehow, he had never fallen into her trap. Clearly, he was aroused by her and probably fantasized about her, but when it came time to act, he didn't. There had to be a way to get him wrapped around her pretty little finger. The internet was just the place to look for ideas.

After several hours of perusing various forums and YouTube videos, Violet came across a YouTube series called 'Hypnotizing Your Man.' Jack wasn't her 'man', but the concept was the same. She wanted control over him like she effortlessly had over everyone else.

The videos were a series and with nothing else to do, Violet settled in and played them, hoping to figure out the secret to hypnosis and ultimately the secret to putting her brother in his rightful place at her feet.

**

Jack struggled for hours to come up with the exact words that he wanted to use convey his feelings to Chloe. It was the most difficult passage he had to come up with and that included any of the essays he had ever written. Why was telling Chloe that he loved her so damn hard?

Because of the fear of rejection and change. If Chloe became too uncomfortable then Jack not only lost a romantic prospect, but he also lost his best friend. Jack threw his phone on the bed in frustration. He couldn't do it. Or maybe he needed the right mindset. Jack grabbed his phone and headed out to his friend's house. Before he ultimately altered his future for better or worse, it was best to do it with a clear head.

Tortoise greeted Jack with their secret handshake and Jack joined the group in Tortoise's basement. When they weren't playing together online, they were hanging out and doing other stuff.

Rochelle and Alyssa, two twins that had been friends with Tortoise and Jack since elementary school and were now beautiful enough to be clearly out of either of their leagues, occasionally stopped by for recreational reasons. Rochelle was preppy and high maintenance and Alyssa was athletic and bold. They were different in many ways, but what they did have in common was their love for weed along with the rest of Jack's friends.

Jack sank into the sofa between Rochelle and Alyssa, who were already feeling the effects of their joint based on their mellow disposition.

"You look tense, Jack. What's up?" Rochelle asked.

"Probably frustrated that he can't get into Chloe's pants." Alyssa said with a snicker.

Tortoise and Orlando, Jack's other best friend, laughed. It was the worst kept secret among the friend group.

"Bro, you need to man up and ask her. I've never seen a dude go on that many dates with one chick and not get anything." Orlando said.

"We're not dating, just hanging out, man. Like I'm doing here." Jack said.

"Ya, except there's a group of us." Alyssa said.

"How come I can be friends with you and not her without expecting anything reciprocal?" Jack asked.

"First, you don't pay for my dinners and second, I don't fall asleep and slobber all over your shoulder during a movie." Alyssa said. "Like I know all of you have probably fantasized about us, but it's pretty clear to everyone that it's always going to be a pipe dream."

Tortoise and Orlando nodded in agreement. Funny how women can call out their own attractiveness and not come off the same way as some narcissistic frat boy would. As if on cue, Rochelle handed Jack a lit blunt. She had always been the more understanding of the two girls. Dating was complicated and girls were complicated. Why couldn't there be an easier way?

**

After watching the video series twice and making sure she understood the process, Violet wanted to test it immediately while it was fresh in her mind. She heard the front door open and was glad that her prey had finally returned home.

Violet walked into the common area and found Jack sitting on the couch with his phone in his hand.

"Hey, do you think you can help me with something?" Violet asked.

"Like what?" Jack said, never taking his eyes off his phone.

"For one of my psychology classes, I have to try and hypnotize someone and then like report the results." Violet said.

Jack finally peeled his eyes away from his phone.

"Hypnosis? Isn't that all bullshit?"

"Guess that's the point of the assignment." Violet said. "If it is all bullshit, then you got nothing to worry about."

Jack laughed. "Like you need hypnosis to control anyone. All you have to do is open your legs."

"Look you little shit, I'm actually trying to do the work now, so are you going to help me or not?" Violet said with her arms crossed.

Somehow, on top of never being influenced by her, Jack always said things that cut deep. Not because they were mean, but because they were the truth and Violet hated that.

Jack sent a message on his phone and threw it on the couch as he sat back. He looked at his sister.