High-Tops to High Heels: Part 2

The first step in any plan of attack was research, of course, and that meant scouring Bobby’s socials for flaws and weaknesses. Kimberly knew this was classic jilted ex behavior, spending hours scrolling through his Instagram and Facebook photos, but she was doing it with a purpose. God, it was excruciating seeing so many photos of his smug grin: at parties with his basketball teammates, at the beach, at the mall.

There were action shots of him in games, all of which were drowning in “hearts” and “likes” from his many admirers, and his status updates were always some stupid, faux-inspirational line with a dumb hashtag, usually #STRIVE4GREATNESS. The most painful photos were of them together, of course. Bobby hadn’t bothered to delete or untag any of them, instead choosing to let them get slowly crowded out by photos of him with other girls, one of whom would surely be his new girlfriend soon. Yes, Bobby Vickerson was heartless, callous, and could apparently do no wrong.

But then she found exactly what she was looking for. It was a tagged Facebook photo, uploaded not by Bobby, but by his mother -- which was honestly a bit of a surprise. At Jefferson High, Bobby was the undisputed main attraction, no questions asked, but in the Vickerson household, there was another one, and her name was Serena. Kimberly had never actually met Bobby’s older sister, who now lived mostly in either Paris or New York, but she had heard the name plenty, and Bobby’s mom had posted enough photos of her to emblazon the pouty brunette fashion model firmly into her memory.

Being the best high school basketball player in Green Lake was one thing, but being an up-and-coming model who had already done her first spread for Gucci was another. Plus, Bobby’s basketball talent had only really taken off in the past few years, while Serena had seemed destined for stardom from an early age. Both of Bobby’s parents obsessed over Serena’s modeling career, and even now that she was out of the house, she usually took priority -- in fact, they were currently in NYC to support her at one of her shows, meaning they’d missed the St. Ceylan’s game completely.

That was why at first, Kimberly figured this particular photo was a typical boomer screw-up, and Bobby’s mom had been meaning to tag her daughter, not her son. The photo showed an extremely pretty little girl, maybe nine or ten years old, wearing a powder blue princess-style dress and smiling nervously for the camera with a look in her eyes that made it clear she would rather be just about anywhere else in the world.

Kimberly looked down at the caption and her heart leapt. Bobby’s mom had captioned it as follows: “Halloween 2013, put him in Serena’s old pageant dress, oh my gaaaawd they grow up too fast!! Love u Bobby, my lil’ prince(ss). LOL.”

And just like that, Kimberly had a plan.

#

When she showed up to school the following Monday, Kimberly was dressed to kill: low-cut halter top, short skirt, “Instagram baddie” makeup, the works. She would be the first to admit she’d let herself go a little after Bobby dumped her, in the sense that she’d worn leggings, sweatshirts, and a pony-tail way too many days in a row. But for what she had in mind, she needed to be using every advantage she had over her ex, and one of those advantages was still her sex appeal.

Sure enough, when she sauntered up to Bobby’s locker after math class, Jefferson High’s finest did the same double-take as all the other guys she’d caught ogling her. “Hey, Kimmy,” he said, still casually using the nickname he’d come up with when they were dating -- God, did she ever hate that. “Looking hot today.”

“I’m enjoying being single again,” Kimberly said acidly. “Good game on Friday, by the way.”

Bobby gave a boyish shrug. “What can I say? I don’t lose.”

“You probably should have, with all those free-throws you missed in the third quarter,” Kimberly said. “You were one for six, right? Yikes.”

Bobby rolled his eyes. “Just an off night at the line,” he said. “Yesterday in practice I sank a hundred in a row. I probably won’t miss another all season.”

“A hundred in a row? You really expect me to believe that?” Kimberly asked in a saccharine tone. “There’s no way you can even make fifty in a row.”

Bobby smirked, shutting his locker and leaning against it. “You want to bet on it?”

These were the exact words Kimberly had been hoping for. During the three months they dated, it had become a running theme -- Bobby loved betting, and almost always won. He usually chose the prizes. Kimberly would have to wear a sexy outfit for him, or give him a lap dance, or make him a sandwich, or something of that sort. Now, seeing his ex all dolled up and looking hot again, he was right back in the same mindset.

“Sure,” Kimberly purred. “Fifty free throws in a row. In the school gym. With witnesses.”

“Piece of cake,” Bobby said. “But we need to decide what’s at stake, first.”

“You know my mom’s salon?” Kimberly asked. “Well, for my birthday she gave me a voucher for a total makeover, all expenses paid.”

“Yeah, I’ll pass,” Bobby said, making a face.

“Or I can take the cash value, which is fifteen hundred dollars,” Kimberly added casually. “My birthday, my choice.”

Bobby blinked. “Whoa. Fifteen hundred? I know you said business was good, but…”

“You’d be able to buy those Lakers tickets you’re always dreaming about,” Kimberly pointed out. “Pretty good seats, too. Weren’t your parents supposed to take you to a game last summer?”

“Went to fashion week in Milan, instead,” Bobby muttered. He had a far-away look in his eye, no doubt fantasizing about seeing his favorite team. Then he shook himself, returning to reality. “Look, Kimmy, there’s no way I lose that bet,” he said. “We both know that. But I also can’t pony up fiteen hundred for it to match the stakes, so it wouldn’t be a real bet anyways, and that wouldn’t be fair.”

Kimberly was a little taken aback by the integrity on display, until she reminded herself that it was just part of Bobby Vickerson’s “perfect” act. “That’s not a problem,” she said slyly. “See, if I win, you still get the prize. Except it’s the makeover. I take you to the salon, and then out on a date.”

“So you want to get a pedicure, couple’s massage, and go out for lunch?” Bobby raised one eyebrow. “Is this some weird attempt to get back together, Kimmy? Because I really wish you all the best, ‘namaste’ and whatever, but we were…”

“Oh, no, not that kind of salon visit,” Kimberly said. “I mean you’re going to get a full makeover, as a girl, and wear whatever I pick out for you. Like my own personal Barbie doll. You know?”

Bobby momentarily paled, no doubt having Halloween flashbacks, before he regained his confident swagger. “What, is that some kind of kinky fantasy for you?” he demanded. “You secretly into chicks, Kimmy?”

“You taking the bet or not, Bobby?” Kimberly demanded. “I mean, if you don’t think you can win, we might as well not bother.”

“Fifty free-throws for fifteen hundred bucks?” Bobby smirked. “You’re just giving it away. You got yourself a bet.” He looked her up and down again, with the old salacious glint in his eye. “By the way, did you gain some weight? It looks good on you. That ass is thick.”

Kimberly smiled at him through gritted teeth. “Friday. School gym. Fifty free-throws.”

#

As soon as she got home, Kimberly booted up her MacBook Air and made a brand new LiveJournal account, using the carefully-chosen name “bboy2003.” This was possibly the most important part of the plan, and she had to make sure she did it right. She had read through hundreds of Bobby’s status updates on Facebook to get a good feel for how he wrote, and now she was going to put it to use. Deciding the first entry was the most important, she labored over it for almost an hour, making numerous versions. After a few final tweaks, she sat back, satisfied, and read it over.

“I can’t believe I’m doing this, but I feel like if I don’t express myself somewhere I’m literally going to explode, so here it goes… My life is probably one most people would trade for in a hot second. I’m one of the popular kids at school, I won’t say which school. I’m an all-star athlete and team captain, I won’t say which sport. I’ve dated some of the hottest girls in my grade, I won’t name names. But the thing is, it’s all a lie.

Even with all that cool stuff going on in my life, my happiest memory, like, maybe my only happy memory, is this one Halloween when I was ten. Why? Because I got to dress up like a princess. Yeah, I pretended I totally hated it. But on the inside, I was in heaven. I loved being pretty. I loved being girly. I loved being MYSELF, because on the inside, for as long as I can remember, that’s been the real me.

For as long as I can remember, I’ve also been so scared people are going to find out -- that’s why I always have to act tough, why I always have to dominate in sports, even just in gym class, why I always have to be chasing girls. It sucks so much, living this total lie, pretending to be a tough manly jock when I wish I was a cute sexy cheerleader, but at least here I can be myself. My secret diary… #BOY2BABE #PRINCESSINHIDING #STRIVE4REALNESS.”

It was perfect. Kimberly cracked her knuckles, punched the enter key on her keyboard, and sat back in her chair. Now she just had to make sure Bobby lost the bet.

#

Thanks to the power of social media and Jefferson High’s obsession with all things Bobby Vickerson, by the time the final bell rang on Friday, every single person in school had heard about the bet. That meant a sizable crowd was already waiting in the gym when Kimberly arrived, phones out and ready to put the whole thing on Instagram. Bobby showed up a few minutes later, accompanied by his usual circle of teammates and suck-ups. When he saw how many people had showed up to watch, he broke out in a huge grin and started handing out high-fives and fist-pounds immediately.

“Alright, let’s do this thing!” he whooped. “Who wants to see me win a ton of money off a crazy ex?”

“Big talk for someone who choked at the line last game,” Kimberly said primly. “Fifty free throws in a row, starting with your first basket made. I’m sure your adoring fans can keep track.”

She pulled a basketball out of her bag and tossed it over, trying to look casual. Bobby caught it easily and immediately made a face.

“Nice try, Kimmy,” he said. “What are you trying to pull? This is covered in freaking Vaseline.” He held up his shiny fingers as proof. “You think I’m that dumb? I get to pick my own ball.”

Kimberly pursed her lips, trying to look disappointed. She had done her homework prior to arranging the bet -- not her actual homework, naturally, but her “revenge on Bobby Vickerson” homework -- but in a few minutes things would be out of her hands, and she would just have to hope her plan worked. DeShawn Baker, Bobby’s power forward teammate, was already wheeling the big container of basketballs out of the gym storage room.

Bobby wiped his hands off on his jersey, then made a big show of carefully selecting a ball, nose wrinkling slightly from the strong smell of Axe -- clearly somebody had set off another “body-spray bomb” in the locker room. He picked out a Vaseline-free basketball, spun it on his finger, and gave a nod of satisfaction.

“Well, here we go,” he said. “Just to restate the terms of the bet, like, for the Instagram… If I win, I get fifteen hundred bucks. Correct?”

“Correct,” Kimmy said. “And if you lose, you get a full makeover and wear whatever I decide, from the skin out, for a date at the mall. If you try to go back on the bet, you owe me the money.”

“Perfect,” Bobby said, mugging for the dozen phones recording him. “Let’s do this thing.”