"What did you just say?" Theodore wanted to make sure he'd heard his best friend right.
"You're not very bright, are you? I said that we make a bet that YOU can't pull off a trick on at least one out of three random people to make fifteen bucks." Ellie, a half human, half esper hybrid, repeated herself from before.
"No, I got that part. WHAT was the cost of losing?"
"Yeah, this is where things get fun. The loser has to switch gender for five years."
"Why, exactly?"
"It's fun, and deviates a bit from our usual bet."
"HOW is that fun?"
"It's fun for the winner. After all, what's more amusing than watching your friend be annoyed with you for the next five years?"
"How would we explain the random change of gender?"
"We wouldn't have to. People around us would only remember the 'new form' we have."
"And if we lose, we lose our original self?"
"Oh, no. I consider a non-wanted mental shift the same thing as killing someone. However, the attraction WOULD have to change. After all, me still being attracted to boys AS A BOY? No, I hate that kind of thing."
"...Still, five years is a really long time."
"You remember your old rule?"
"Which one?"
"The one about turning down bets."
"Yeah, I do. If I turn it down, I'm forced to take the next one."
"Right. So, the next one would be similar, just slightly longer and more embarrassing."
"That's not fair."
"Hey, you never plugged that loophole."
"True. In hindsight, I should have."
"Like I said, you just have to make fifteen bucks off of a random stranger in the park. I'll be nearby, but you'll have a monitor on you. The monitor will detect if I'm cheating by hypnosis."
"...Just fifteen bucks?"
"Just fifteen bucks."
Theodore thought for a minute. He had to make fifteen bucks, playing off of any random person's possible stupidity. If he won, he had a best friend who was a guy. He would be more comfortable talking to a friend like that anyway, even though he would know that her mind would still be dominant. However, the other side of the coin was that he became a girl for the next five years. Granted, one of his deepest secrets was a wish that he could know what a girl's life is like for a little while, but it was just a fantasy. It would never come to pass. However, she was threatening him with a deeper punishment for turning down the bet.
"...OK. We'll do it. Let's meet tomorrow at noon in the park in order to get this bet going."
"All right, that's fair. Later!"
"Bye."
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Theodore showed up a few minutes before noon, and looked through his wallet. Thirty bucks, all in fives. If he could manage to walk out of here with at least forty-five bucks, he won the bet. However, he only got to try three times. He prayed silently that he could find SOMEONE stupid enough to take the deal. Ellie arrived directly at noon, and smiled at Theodore.
"You ready?" Ellie asked.
"Yeah. Let's go."
"OK, here's the monitor. This will PROVE that you can't trick people like that, even though you say that some people could be that stupid."
Theodore went up to his first attempted victim.
"Hello, sir. Do you have two tens for a five?"
"Why sure, I have some money in my wallet.... Wait, how much did you say?"
"Two tens for a five."
"Kid, you're slick. I'll grant you that. However, I'm not falling for that trick."
Dang it, that's one down and two left...
"Oh well. Can't say I didn't try!"
"Hey, kid. That was REALLY smooth, though. You ALMOST had me. Here's ten bucks, how's that?"
"OK, thanks!"
Theodore sat down on a bench for a few minutes, then decided to try again.
"Excuse me, ma'am. Do you have two tens for a five?"
"Please, I know that trick. I love those comedians, and it's not working on me. Goodbye."
DANG IT! I need five more bucks by the end of the third attempt in order to win!
Theodore decided to try someone walking through the entrance. After all, they wouldn't expect to be swindled within a few minutes of walking in, right?
"Hello, sir. Do you have two tens for a five?"
"Wow. I was going to try that trick today. Have you tried it yet?"
"Uh, yeah. It didn't work on either of the ones I tried it on."
"Ah. Well, just because you had bad luck doesn't mean I won't. Later, kid."
Ellie, who had been following Theodore to watch him try three times, walked up to his side.
"Let me see your wallet."
Theodore brought it out, and Ellie chuckled.
"So, you managed to get someone feeling sorry for you and give you ONE ten for nothing. Still, that's NOT fifteen bucks. You lose. I TOLD you that people weren't that stupid. A bet's a bet, follow me."
On the way home, Theodore remembered a few of the older bets. Usually, if he lost, he would have to be Ellie's butler for a day or so. And if he won, he would make Ellie turn something she really liked in nature into something she hated. For example, there was one time where he made Ellie turn a butterfly into a tarantula. He smiled at that memory, remembering how much she wanted to hit him at that point. However, he knew that this bet was way more complex than a simple "service work". He lost, fair and square. Sure, he made ten bucks, but he lost something that was worth far more than that: some of his dignity.
-------------------
When the pair of friends reached Ellie's home, Ellie practically had to drag Theodore upstairs. In fact, the only reasons Theodore even went up the stairs were that he had lost the bet, fair and square AND her magic. She literally pulled him through mid-air all the way up the staircase.
"No chickening out. Or do you want to have the worse punishment?" Ellie smiled.
"Fine, you win. We're here, just get this over with."
Ellie started an incantation. Theodore closed his eyes in defeat, and opened them when the incantation was over. Ellie told him to stand up, and he did. When he stood up, he started to shrink. And not just a little bit; he shrank from five foot eleven to five foot two! His hair started to grow, changing colors from light brown to dark brown as it lengthened toward the center of his back. His face started to round more, his facial hair retracted and his eyes became bigger in proportion to his face. He felt a slight tingling sensation as his leg hair retracted. His legs became slender as well. His waist became more evident. His arm hair retracted in the same way his leg hair had, and he lost the slight bit of muscle he had on his arms. He felt a slight tugging sensation on his chest, and looked down to see breasts forming. They didn't seem as big as he had expected them to be, which made him somewhat happy; he didn't like large breasts. He cringed slightly as he felt his manhood slip into womanhood, then turned to Ellie.
"OK, can I go now?" He (now she) was shocked at the high-pitched sound that came out of her mouth.
"Nope. After all, there's more to the change!"
She looked back down at her new body, and saw her clothing start to change. The first thing she noticed was a support on her breasts; she had a bra. Her black T-Shirt started to shift, and as it did, it turned into a lighter and lighter gray. By the time her shirt had completely changed into a blouse, it was a pure white. Her jeans changed material, and started to merge from the center of the top. Meanwhile, the bottom of her jeans started to rise back up toward her knee. Along the way, the jeans were changing color. When they stopped changing, her jeans had become a vertically striped skirt that reached her knees, with alternating stripes of red and black. Her socks started to change next, changing from a cotton material to a fine, brown silk. They stretched up her legs until they became brown pantyhose. Her briefs became smoother, and started to contract toward her new genitals. When they stopped, she was sure that they had become panties, but she didn't want to check. Finally, the heels of her plain, white tennis shoes started to push out, making her seem a little bit taller, probably around five foot four. The shoes became black and smooth, yet firm.
"There. NOW it's done. So, Theodore doesn't fit you anymore. It's a guy's name, not one for a pretty young lady like yourself. I'll be nice and let YOU pick the name you want to be known by."
Theodore turned to look at the mirror in Ellie's room. She stared at the reflection for a little while, then thought of a name that she liked.
"Caroline. I like the name Caroline."
"Good choice. Things are going to be more interesting and fun for the next five years. Ready?"
"I guess. I don't really have a choice." The two friends looked out the nearby window, looking toward the future. Ellie smiled. Even though she knew that her friend was still Theodore, she felt more comfortable sharing more about her life now. Meanwhile, Caroline expected to have a great learning experience here, especially because she now could learn what a girl's life is like firsthand.