Going after his crush.

Kendra Garner. An absolute beauty, with long, red hair framing her flawless pale skin. Striking green eyes, perfectly set above her freckled cheeks. Only 5'7'', but with legs belonging to someone much taller. She was skinny, yet still had some meat where it counted. C-cup breasts with a plump round ass. John had a crush on her from the moment he saw her.

She wasn't just a pretty face either; she was the smartest student at their old high school and not nearly as cruel and vindictive as the other popular girls. The only problem was her other half, Trent.

Trent was a stereotypical jock, brown hair, blue eyes, and built like a truck. He wasn't very smart, but what he lacked in brains he more than made up for in brawn. And by bullying anyone he didn't like. Which included John. Any bet John managed to trick Trent into was both preceded and followed by a beating. He kept this out of Kendra's view, as she didn't approve of it, but even when she caught him she never dumped him.

And now it just so happened that they both went to his college.

After his classes, John immediately headed towards Kendra's dorm; the address to which he had managed to get from one of Kendra's friends. After a few minutes of walking, he arrived in front of her room. He knocked, hearing her coming towards the door. As it opened, John was once again stunned by her beauty.

"Hi Kendra," John said, quickly unstunning himself.

"Oh, hi John, what are you doing here?" Kendra said, only remembering his name after a few seconds.

"Well, I remembered that we go to the same college and I wanted to drop by and say hello. May I come in?"

"Um, I guess so," Kendra responded, clearly wondering why this guy she had bearly spoken to in high school wanted to talk to her now.

John entered and sat in the one desk chair. Kendra lived in a single so the room consisted only of a desk, chair, dresser, and bed. Kendra sat on her bed.

"I'm going to get straight to the point. I want to have sex with you," John said, breaking the temporary silence.

Kendra took a sentence to process what she had just heard before responding, "What the fuck? You come to my dorm just to say you want to have sex with me? You know I'm dating Trent and even if I wasn't...what the fuck?" Kendra seemed both offended and confused, taken totally off guard.

"Of course I knew you would say that," John said, completely calm. "Which is why I propose we make a bet."

"Why would I make a bet with you? Everyone knows how good you are at them. And besides, what could you have that I would be willing to potentially fuck you for?" Kendra responded incredulously. She really couldn't believe the nerve of this guy.

"Oh, I have what you want more than anything. I can get you into Yale." John said, a smug look on his face.

Kendra's dream school had been no secret. In high school, she would wear Yale shirts and constantly talk about their programs. As the valedictorian, most people expected that she would make it in easily, yet somehow she had been rejected and ended up following Trent to John's current college.

"How would you manage that?" Kendra asked skeptically after she had gotten over the initial shock of John's claim.

"A few bets here and there, I'm sure I could make it happen," John answered nonchalantly. "You deserved to be accepted in the first place, so it shouldn't be too hard. I mean, what did you get on the SAT, a 1500?"

"1550" Kendra corrected.

"Exactly. I got a 1200 and here we are, at the same school. Doesn't seem very fair."

Kendra was speechless, completely lost in thought. Could he really get her into Yale? Probably. But was it worth risking having sex with him? Probably. But could she even win a bet against him? As long as she had known John, she had never heard of him losing a bet. However, he had never made a bet with her. Kendra had made up her mind.

"Fine, I'll make a bet with you." Kendra finally said.

"Excellent. I have the perfect idea. Who has the bigger dick, me, or Trent? If I do, we fuck. If he does, I'll get you into Yale." John said smugly.

Kendra was once again taken aback. John seemed really confident about that bet. He couldn't possibly... It didn't matter.

"No, it has to be something else," Kendra responded after composing herself.

"Ah, Trent must have a small dick then," John said with a shit-eating grin on his face.

Kendra visibly grew angry but managed to hold herself back. "I will decide on the competition."