Visiting his ex-girlfiend.

Well, "ex-girlfriend" maybe a little misleading. Back in his sophomore year of high school, after realizing that Kendra wouldn't be available anytime soon, John set his sights on a different girl. Her name was Jennifer, but she always went by Jen. She was short, only around 5'4'', with long brown hair. She was Latina, although her skin was relatively light. She had a cute face, usually adorned with black-rimmed glasses. She had small, though assumedly perky, breasts and a tight little ass. She also had a bit of a punk aesthetic, typically wearing black outfits and occasionally getting highlights in her hair

John had decided to take his chances and ask her out. Although Jen was by no means a bad person, she did have a tendency to be a bit brash. After a firm rejection, John still refused to give up. He challenged her to a bet, winning and forcing her to date him for a month, hoping to win her over in that time. He did not.

Since then, John had always held a bit of a grudge against Jen. It was somewhat irrational, but he just couldn't get past it. And so, John decided to pay her a visit. He didn't have much of a plan of how to convince her to bet him, as he didn't believe he would need it. Jen was stubborn, hot-headed, and wasn't exactly the brightest. She wasn't an airhead, but John believed that it wouldn't be too hard to trick her.

So after an uneventful night, followed by a morning of classes, John set out to meet her. He knew that she had stayed in the city, albeit at another college. He also knew where she lived, having been there a couple of times when they were "dating". She still lived with her parents, although they would frequently leave on business trips and the like, so she was most likely alone.

Having finally arrived at Jen's house, John knocked on the door.

"Coming!" A female voice yelled out from inside.

The door opened, revealing Jen wearing a plain black top and tight black jeans. Her hair was a bit different than John had last seen, with a blonde streak on each side.

Jen's face went through a few variations when she saw John. It began neutral but quickly changed to shock before settling on mild annoyance.

"What are you doing here?" She asked, annoyed, and genuinely confused.

"Hi, Jen. It's been a while. I heard you had stayed in the city and decided to pay you a visit. Can we talk?" John said, hiding his emotions as best he could.

"Uh, sure I guess," she responded hesitantly.

John followed her into the house, to a fairly large living room, where he sat down on the couch as she took a chair.

"So what do you want?" Jen asked, clearly not in the mood for small talk.

"Right to the point I see. I didn't like the way that our relationship ended and I wanted to see if we could try again," John responded, already knowing what Jen would say.

"Relationship? You fucking **** me to go out with you on a bet! Fuck off."

"I thought you would say that, so I have a different proposition. Let's make another bet. Not for a relationship this time. No, this time all I want when I win is to fuck you," John stated matter of factly.

"Fuck me? No way! Also, what do you mean when you win?"

"Well you seem to think you can win, so what's the problem. Also fucking isn't that big of a deal, especially compared to a month of dating."

Jen's face said differently.

"Why does it seem like you don't think so?" John asked rhetorically. "Oh my God, you're a virgin aren't you?"

Jen looked like she wanted to refute his claim, but didn't say anything, reaffirming John's idea.

"Alright, I understand. How about this? If I win our bet, I'll only take your mouth, so you don't have to worry about losing your virginity."

"I still have no reason to make a bet with you," Jen said defiantly.

"Hmm, alright then. If you win, I'll give you my apartment."

"What!?" Jen couldn't believe what she had heard.

John smirked, knowing he had her. "You heard me. I've been living on my own for a while and I know that you've been wanting to move out. If you win our bet I'll give you my apartment and even pay the rent and utilities."

Jen was conflicted. John's offer was great, but she knew how good he was at betting. Eventually, she decided that this chance was too good to pass up.

"Fine. I'm choosing the competition though. Since I know you like to prepare a lot, I'll pick something you'd never expect. A spelling competition!" Jen said triumphantly.