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High-Tops to High Heels: Part 6

Kimberly put the conversation with Beverly out of her mind before she showed up to Bobby’s house, dressed as casually as possible, bearing snacks and some “spa” stuff, just as if he was a female friend instead of a horny ex. To her surprise, she was greeted at the door by both of Bobby’s parents. It was rare for them to be home at the same time, and last time she checked, it didn’t take two people to answer the door.

“Hey,” Mr. Vickerson said. “Kimberly, right?”

“Of course it’s Kimberly,” Mrs. Vickerson scolded. “They dated all last year, you’ve met her before… Oh, wait, unless that was Beverly? Sorry, dear. Bobby loves his cheerleaders.”

“I’m Kimberly,” Kimberly said through her teeth. She had met Bobby’s parents on several occasions, of course, but usually in a brief coming-or-going situation. They were both tall, good-looking, and well-dressed people, who usually exuded confidence -- a more tempered version of Bobby’s old cocky bravado, actually. But tonight, for the first time she could remember, both of them seemed a little awkward.

“Of course, of course,” Mr. Vickerson said. “Bobby mentioned you were coming over.” He glanced over his shoulder, then lowered his voice. “Can we talk in the kitchen for a second?”

Kimberly blinked, then nodded wordlessly, unsure where this new development might lead. She followed Bobby’s parents to the kitchen, and, at Mrs. Vickerson’s gesture of invitation, pulled up a stool. “Uh, what do you want to talk about?” Kimberly asked. She could guess the basics.

“It’s about Bobby,” Mrs. Vickerson sighed.

“What isn’t?” Kimberly joked, with a fake smile. Bobby’s parents didn’t seem to get it -- they looked at each other in confusion.

“Uh, well, I’m sure you’ve noticed that he’s having some problems,” Mr. Vickerson said. “His grades are even worse than usual, and he’s spending a lot of time… Home.” He scratched his head, as if it was an unfathomable concept. “He used to always be out with his basketball buddies, or girlfriends.”

“We’re very concerned about him,” Mrs. Vickerson said. “It’s just coming at a bad time, is all. Serena has a show coming up in Rio, and we’re flying down to attend.”

“Do you know what’s going on with him?” Mr. Vickerson pressed. His face turned slightly red. “I think he was involved in some sort of prank, a little while ago? The whole crossdressing thing?”

“He really did look gorgeous in those salon shots,” Mrs. Vickerson said, smiling off into space. “Not the same attitude as Serena, not the same poise, but…”

“Anyways, Bobby’s behavior has been a little strange since then,” Mr. Vickerson interrupted. “I don’t know what’s going on with him. Do you?”

Kimberly gave him her most wide-eyed, innocent stare. “I really don’t,” she said. “Not entirely. But I think the most important thing, like, the best thing you guys can do for him? Is just give him space. Let him figure it out. Don’t try to talk to him about it, don’t do the “we love you no matter what” spiel -- he’ll get freaked out. Just act like everything is normal.” She gave a beatific smile. “That’s what we learned on LGBTQ day.”

Her phone buzzed, and she saw a message from Bobby: You here yet or what?

“I better go upstairs,” Kimberly said, hefting her spa kit to make it as obvious as possible. “See you guys!”

Mr. Vickerson was slightly pale in the face, while Bobby’s mom, on the other hand, looked slightly intrigued. Kimberly did her best not to look too gleeful as she entered Bobby’s room. He was lying on the bed, wearing his usual baggy sweats and hoodie, but he sat upright the second she shut the door.

“You weren’t talking to my parents, were you?” he asked suspiciously.

“Your mom wouldn’t shut up,” Kimberly lied. “She wants me to join her hot yoga class.”

Bobby rolled his eyes, and grabbed the remote to set up Netflix. As they settled in on the bed, he initially protested the facial masks and nail kit, saying she’d done enough damage to his masculinity already -- if only he knew. But once he was engrossed in an Adam Sandler comedy, she took advantage of his distraction to start buffing and filing his nails, something she’d done now and then while they were dating, before applying a pink-tinted varnish to each one. He only noticed when she snapped a photo with her phone.

“Hey, what are you doing?” he demanded, jerking his hand away. “I didn’t say you could paint my nails!”

“It’s just a varnish,” Kimberly said. “I took a photo to compare before and after. It’s just your hand, see? Nobody would even recognize it, so who cares?”

“Whatever,” Bobby said, returning his attention to the movie, but keeping his hands nervously clenched into fists. Maybe she had overstepped a little bit, reminding him too much of the whole makeover thing, but she had taken the photo for a reason. As soon as Bobby left to go to the bathroom, she opened up her MacBook Air and posted the photo on the LiveJournal account of “bboy2003.”

“Doing my nails today, still too nervous to grow them long though. What would my teammates say? But still, I love the pink. What do you guys think? First photo, haha. #BOY2BABE #NAILSDID #STRIVE4REALNESS.”

The most important part, of course, was the fact that Bobby’s Tomcats team jacket was in the background, with the team name in plain view. Another breadcrumb for the curious people in the comment section, and another piece of evidence in the case of Barbie vs. Bobby Vickerson.

“Ready to do this thing?” Bobby asked, returning from the bathroom with his dick hanging out of his pants.

“Nope, so put that little thing away,” Kimberly said. “And I mean now.”

Bobby groaned, but he stuffed it back in his pants. Kimberly had to admit she was a little impressed. With all the female hormones in Bobby’s system, his male sex drive was probably cut in half, and she knew that the estrogen pills would be making it harder and harder for him to get, well, hard. Even so, he had a decent erection.

“Got any more pillows?” she asked, getting comfortable on the bed again.

“Dunno,” Bobby said sulkily. “Check the closet.”

She rolled her eyes and got up, walking over to the walk-in closet. As usual, it was a disaster zone. Clothes were thrown everywhere, and there were definitely no pillows. She did notice a big plastic box she’d never seen before.

“Jeez, would it kill you to use a hanger?” she demanded. “This closet is a freaking mess. And what’s in the box, pornos?”

“Hey, wait, don’t look in there!” Bobby shouted, flying off the bed with surprising speed.

“In here?” Kimberly asked innocently, lifting the lid.

She was fully expecting to see a bunch of old Sports Illustrated issues, particularly the Swimsuit Edition kind with stuck-together pages, so what she saw instead left her momentarily speechless: an assortment of MAC makeup products, an expensive-looking blonde wig, a pair of high heels, and several bra-and-panty sets -- including the hot pink Valentine’s Day lingerie from Victoria’s Secret that he’d pulled out of his locker last week.

“Bobby, what the fuck?”

#

Kimberly stared down into the box, at a discovery that defied all explanation. She had definitely considered planting some incriminating things in Bobby’s room, but it seemed Bobby had gone ahead and done that himself. Was it possible that losing the bet and getting made over as a girl had shaken his confidence so badly he was questioning his sexuality? Were the hormones she was sneaking into his protein powder somehow affecting his brain, as well as his body? Was this the weird behavior his dad had been talking about?

“Okay, what’s going on?” Kimberly asked, too flabbergasted to even fake a concerned voice. “I mean, seriously?”

“It’s not what it looks like,” Bobby snapped, shutting the lid. “I can’t believe I invited you over for sex when this whole thing is your fault. You’re the one who started all this.”

For possibly the first time in his life, Bobby was correct. She had started all this, but now, clearly, somehow, it had taken on a life of its own. As she inspected Bobby’s face a little closer, an incredulous grin spread across her face.

“I thought you weren’t sleeping well, but that’s mascara!” she exclaimed. “Did you try to take it off with soap, or something? Try actual makeup remover next time, it’ll go a lot better.”

“What? No! Why would I wear mascara?” Bobby shouted, completely flustered as he rubbed at his eyes. Suddenly, all the fight went out of him and he slumped onto the bed with a groan. “Aw, screw it,” he said. “Okay, I’ll tell you what’s going on, but you can’t breathe a word of this to anybody.”

“Scout’s honor,” Kimberly said, since she had never been in the Girl Scouts, putting her hand on her heart with exaggerated solemness.

“I wasn’t kidding about it all being your fault,” Bobby said. “It’s that freaking video. You know, of me. Where I’m like…”

“Hi, I’m Barbie Vickerson, and I’m going on my first date,” Kimberly quoted. “Wish me luck! Kisses!”

Even though he was probably hearing it for the millionth time, Bobby’s face went red. “Yeah,” he muttered. “That one. Before you took it down, some perv found it on YouTube, and I guess he liked it. A lot. He freaking hacked me, Kimmy.”

Kimberly was too taken aback to even object to the use of her nickname. “Hacked you?” she demanded. “How so?”

“I dunno,” Bobby said. “Computer savvy? But he got into all my accounts, like, all my socials, and even my school email. He could prove it, too. The worst part is, he hacked my webcam and saw me, uh, you know. Spanking the monkey? Taming the one-eyed snake? And he threatened to send the video to everyone I know. Friends and family.” Bobby winced. “It was to a picture of one of Serena’s model friends, except Serena is in it, too. I covered her up, I swear, but that would not go over well.”

“Okay, one, that’s gross,” Kimberly said. “Two, this guy is blackmailing you for what, exactly? It’s not like you have money.” She glanced at the box in the closet, and it dawned on her. “Oh, wow. Seriously?”

“Nothing sexual!” Bobby blurted. “But this guy was obsessed with the Barbie video, Kimmy. He keeps sending me this shit in the mail, like, from Amazon, and I have to watch the porch like a hawk to make sure I pick it up before my dad does. Then he wants me to send him little videos of me, you know, dressing up. Doing my makeup. Walking around in the high heels. He even sent me a freaking dress.”

Kimberly was doing all she could to contain her sheer delight. “I don’t believe it,” she said. “Show me!”

“The dress?” Bobby asked quizzically. “I stuffed it in the bottom of my laundry hamper. The creep said it was expensive and not to wrinkle it, and screw him, right?”

“Not the dress,” Kimberly sighed. “This whole blackmail business. Where’s your laptop?”

“Why do you care?” Bobby demanded. “Haven’t you done enough damage already? If it wasn’t for you, that Barbie video wouldn’t exist, and this wacko never would have found it.”

“As far as I’m concerned, this “wacko” is just a convenient excuse for you to get dressed up,” Kimberly said, though she was desperately hoping otherwise. “You loved it all along! Admit it!”

“Hell, no!” Bobby snapped. “You think I’m doing this because I want to? Are you nuts? Here, I’ll prove it, I’m already logged in…” He passed her his MacBook and flopped back on the bed miserably. “This is the reason I’ve been playing like crap lately,” he said. “I’m freaking out about this whole thing. I keep thinking he’s going to send the jerk-off video to my grandma, or something.”

Kimberly let Bobby ramble on while she read through his emails. The most recent message from his secret “admirer,” whose email address was “mountaindew18@yahoo.com,” was right at the top of his inbox. With a strange mixture of excitement and indignation -- who did this anonymous weirdo think he was, trying to get in on the girlify Bobby Vickerson game without her permission? -- she clicked on it.

Hey beautiful, I loved your last video you sent me, you’re so gorgeous and you can really work those high heels now lol, I love it, but your makeup is still a B-, needs improvement lol, so I want to see you practicing, here are some tutorials to help out… Oh, and remember beautiful, SMILE for me this time or your whole contact list is gonna get a BIG surprise ;)

The email was accompanied by links to several popular MUA channels on YouTube, full of high school girls showing, in detail, how to achieve “Smoldering Bedroom Eyes” or “The Perfect Date Night Glam Look.” Kimberly couldn’t help but get a little thrill at the mental image of hotshot Bobby Vickerson locking himself in his room with a makeup tutorial and a mirror, desperately trying to figure out the difference between bronzer and foundation, or choose the right shade of lipstick to complement his skin tone, but she was even more intrigued to see the video Bobby had sent that elicited such a reply.

“So that lingerie in your locker was from him?” Kimberly asked, putting two and two together. “I thought it was a prank by one of the football players!”

“Yeah, no, it was Mister Perv,” Bobby sighed. “His first “present,” actually, so I didn’t realize what it was. Just saw it on the porch as I was heading to school. It was addressed to me, so I stuffed it in my backpack and forgot about it until practice. When we were getting changed I opened it to see what was inside, and Chet looked over and saw the Victoria’s Secret tag, and, well…” He trailed off, grimacing. “Then when you were talking to me, I got the first blackmail message on my phone. That’s why I took off running.”

Kimberly scrolled down to the next email in the chain and opened the video attachment. It was obviously filmed on webcam, showing Bobby’s room, floor surprisingly clean, from a low angle. The picture was a little grainy, but even so, Kimberly’s stomach gave a flutter of delight as a pair of dainty feet clad in strappy high heels appeared in the frame. A pair of tan, slender legs came next as Bobby walked backward to get in the picture, stepping with surprising ease despite the four-inch heels. Whoever this guy was, he had made Bobby shave his legs, and for that he deserved some credit.

Bobby was now fully in view of the webcam, and grainy picture or not, Kimberly could hardly believe how good he looked. The dress his admirer had bought him was neon pink, clingy, and incredibly short, forcing Bobby to tug nervously at the hem as he checked his image in the webcam, and it made the work of the hormones clear as day in a way sweatpants and hoodies never could, showing off his rounded booty, dainty waist, and, unless Kimberly’s eyes were deceiving her, a hint of honest-to-God cleavage. He had done his best to brush out the wig, which fell in blonde waves around his face, and his natural beauty was enhanced by mascara -- a little clumpy, admittedly -- and a sticky pink lip gloss. He even had a pair of large silver hoops in his ears. As he grimaced at the webcam, still tugging at his sky-high hem, he looked for all the world like a hot, pouty blonde dissatisfied with a new dress.

“So this is why you kept your ear piercings?” Kimberly demanded, utterly delighted.

Bobby flushed. “I’ve been covering the holes with liquid foundation,” he groaned. “He insisted the earrings stay.”

Kimberly kept watching the video, transfixed as Bobby strutted away from the camera, placing each high-heeled pump directly in front of the other, hands on his rolling hips. At the far end of his room, he made a clumsy pirouette, tossed his hair, and came strutting back with an aggrieved “shoot me now” expression that actually only added to the fashion show vibe. Whoever this guy was, he had been making Bobby practice walking in heels, to the point the former jock was now sashaying like a beauty queen. It was incredible. Maybe Bobby had subconsciously picked up a few things from watching so many of Serena’s shows.

And no wonder her ex hadn’t been going to any parties -- he had been spending his weekends home alone learning how to be girly for his secret “admirer.” She realized she had been giving herself too much credit. Bobby’s decline on the basketball court and collapsing social status at school weren’t just the product of her makeover scheme and hormone campaign. Bobby was getting hammered from two separate fronts at the same time. For a minute, Beverly’s words came back to her, and she almost felt sorry for him.

“Yeah, I know, it’s super gay,” Bobby sulked, watching himself swish and prance on the webcam. “I don’t know how girls stand all that dumb shit. Guess it’s genetic.”

And just like that, the feeling sorry for him thing was gone again. It was amazing how he could do that. Ignoring her ex, Kimberly swiftly forwarded herself the whole email chain, so she would be able to study it further later. Bobby was right about one thing: whoever was blackmailing him was definitely a huge perv. And huge pervs were often susceptible to blackmail themselves, so if she could figure out who was behind it, maybe she could use them as another way of getting at Bobby.

“First thing’s first, we need to find out who this guy is,” Kimberly said. “And I know just how to do it.”

“How?” Bobby asked. “He’s a hacker. They’re all freaking geniuses. They, you know, cover their tracks or whatever.”

“He might be a genius,” Kimberly admitted. “He’s definitely horny for you.”

Bobby dry-heaved.

“Or for “Barbie,” whatever makes you feel better,” she said, rolling her eyes. “The point is, horny makes smart people stupid. I’m thinking a honeypot, sting operation kind of thing. You’re the honeypot, obviously.”

“And he’s what, Winnie the Pooh?” Bobby asked glumly.

“Sure,” Kimberly said. “Except, you know, horny.”

“Forget it,” Bobby said. “I’m not going to do some dumbass Mission Impossible honey sting whatever and risk pissing off the perv who can give my grandma a heart-attack with one click, okay?”

Kimberly ignored him, instead focusing on the email server’s chat function, where she could see, in plain sight, that “mountaindew18@email.com” was currently online. Frowning, she tapped out a message:

Can we talk?

The reply was almost instantaneous: Sure beautiful, what’s up? Turn the webcam on lol I want to see your pretty face ;)

Thinking quickly, she responded: I don’t have my makeup on yet and I don’t want you to see me without it... I want to look pretty for you, haha.

There was a long pause as Bobby’s blackmailer, obviously confused, typed and backspaced several messages. Very funny lol, but seriously, put it on, then we can talk.

“Hey, what are you doing?” Bobby demanded, grabbing the laptop. “You’re freaking chatting with him? What the hell, Kimmy?”

“What, you’ve never seen To Catch a Predator?” Kimberly demanded. “This is how it works, Bobby. We have to gain this perv’s trust.” She snatched the laptop back. “Look, do you want this hanging over your head for the rest of your life? Or do you want to go back to being Bobby Vickerson, superstar asshole extraordinaire?”

Bobby grimaced. “I’m still a superstar,” he muttered sulkily. “I’m just coming off the bench, that’s all.”

“Let me catch this creep for you,” Kimberly persuaded. “Like you said, this whole thing is my fault, right? So let me help fix it.” She grabbed the old stand-alone webcam from Bobby’s desk. “Look, I’ll sync the video chat to this instead of the laptop cam. That way I can do the typing off-screen, while you sit in front of the webcam. Easy.”

A new message appeared from the blackmailer: Bra and panties too please ;)

Bobby’s face paled. “No,” he said. “Screw this.”

“What’s the big deal?” Kimberly demanded, knowing full well what the issue was -- if Bobby took off his baggy sweats and hoodie, he would be showing her exactly how badly his work-out regimen had gone. “I’ve seen you in a bra and panties before, remember? At the salon? Heck, I’ve seen you naked.”

Bobby swallowed. She could see the conflict on her ex’s face, pride warring with his desire to be free of the blackmailer, embarrassment over his rapidly developing curves fighting his need to tell somebody about it and get it off his chest. He grimaced, sighed, and rubbed the back of his head.

“There’s something else going on, too,” he said. “You know in the video, with me in the dress, I look kind of…”

“Curvy,” Kimberly supplied.

Bobby flushed. “It’s not padding,” he said in a small voice. “I’ve got this, uh condition. Totally normal, for guys going through puberty.” He took a deep breath. “I’m growing boobs. There. I said it.”

“You’re not growing boobs,” Kimberly said, trying to contain her delight. “That’s crazy. I mean, maybe you’re gaining weight from stress. Who wouldn’t, with all this blackmail stuff going on?”

Bobby scowled. “I’m hardly gaining at all, but my butt got bigger somehow,” he admitted. “I think I’ve been doing too many squats at the gym, and not enough bench. But the main problem is the boobs. It’s called...” He frowned. “Guy, knee, coma… Something.”

Kimberly swallowed. If Bobby had gone against his usual doctor distrust, and taken a blood test, some very strange results were sure to show up. “Have you, uh, sought medical attention?” she asked, crossing her fingers behind her back.

“Why would I?” Bobby asked scornfully. “I have the internet right here.”

Kimberly breathed a sigh of relief. “Yeah,” she said. “Web MD always knows best.”

“Exactly,” Bobby said. “I’m not going to go get felt up by a doctor who will tell me shit I already know.” He held up his phone. “Here. It’s called gynecomastia. And it says nearly all cases go away on their own.” He gritted his teeth. “I just have to hang in there, and not let anybody see me shirtless, that’s all.”

“Then we better deal with your blackmailer before he gets any more demanding,” Kimberly pointed out, redirecting her ex’s attention. “Come on, Bobby, let’s bust this guy. I’ll turn around while you get changed, okay? And I promise I won’t laugh.”

Bobby hemmed and hawed, but in the end he sighed, closed his eyes, and gave a curt nod. “Alright,” he said, opening them again. “Screw this perv. Let’s catch a predator.”

Kimberly smirked. “That’s the spirit, Barbie.”

#

As agreed, Kimberly turned around while Bobby changed, and the anticipation was kind of killing her. She wasn’t sure why, but the whole thing -- Bobby being blackmailed, Bobby growing boobs without knowing why, Bobby agreeing to put on lingerie for the webcam -- was really, really hot. In a weird way, yes. But still hot.

No matter what she saw when she turned around, though, she reminded herself that she needed to downplay her reaction. The more Bobby freaked out about his body, the more likely he was to get an actual doctor’s opinion, and she had no idea how she was going to handle that particular can of worms.

“Okay,” her ex said at last. “Ready.”

But when she turned around, she completely failed to suppress her gasp. She probably should have paid “Skeeter” twice what she had for the hormone pills, because they were going above, and beyond, the call of duty. Bobby Vickerson was a bombshell. He was wearing the Valentine’s Day set from Victoria’s Secret, and she had to deal with the very real possibility that he might be pulling it off better than she ever could.

His growing boobs couldn’t be bigger than an A-cup, but the hot pink bra’s gel padding and underwire trickery made the most of them, molding them into a tempting little rack of cleavage. The matching bikini-cut panties hugged his girlish hips and bulge-free crotch, and when he turned she got an eyeful of curvy butt that was in no way male. To top it all off, his tiny waist and flat stomach still didn’t have an ounce of extra fat on them -- it was almost infuriating.

“Oh, my God,” she said, completely forgetting to downplay her reaction. “Uh, Bobby? What do you do in the locker room?”

He heaved a deep sigh, making his boobs quiver, just slightly, in their silky cups. “I’ve been showing up early to change, and leaving late,” he said in a tiny voice, staring at the floor. “Nike makes these awesome compression shirts, and they work pretty well to keep everything, uh, flat. You know, when I’m actually playing.” He grimaced. “But I think people might be starting to notice. Chet was looking at my chest funny the other day.”

“Yeah, I don’t doubt it,” Kimberly said, blinking. “And, um, your crotch?”

Bobby flushed deeply. “The creep sent me a YouTube video, like, how to ‘tuck.’ Same thing you did with that tape.”

“Well, you did a great job,” Kimberly said, clearing her throat. “But you know, now that I’m looking at your chest up close, it’s really mostly the push-up bra,” she lied. “Seriously, I’ve seen bigger mosquito bites. I think half of it’s in your head. Here, let me help with your makeup.”

Bobby nodded glumly, taking out his array of cosmetics and donning the wig with surprising ease. Clearly he had been forced to learn by trial and error, but watching the intense focus on his face as he adjusted the lace front, the same kind of focus he’d once applied to his basketball drills, was oddly titillating. She took over on the makeup front, applying some eyeliner and mascara, using a pencil on his brows, and coating his lips in a coral pink lipstick. Nothing too advanced, since that would look suspicious, but it was a lot faster than letting Bobby do it all himself.

“Quit fidgeting,” she ordered, as her ex flinched away from the mascara brush. “Keep your head still and your hands in your lap, okay?”

Blushing furiously, Bobby reluctantly did as he was told, folding his hands on his smooth thighs. Wearing sexy lingerie in front of her was obviously not doing much for his macho pride, and even as he kept his head still his eyes kept darting nervously towards the webcam he would soon be put on display for.

“Did you sneak this stuff from Serena’s room?” Kimberly asked, as the thought suddenly occurred to her.

“Are you kidding?” Bobby scoffed. “Some of it I got from my mom’s bathroom, some of it the creep sent me. Serena’s room is the freaking Ark of the Covenant. You open it, you get your face melted off by my mom. Everything has to be perfect for the ten days a year she’s actually here.”

“Your mom’s kind of obsessed, isn’t she?” Kimberly asked conversationally.

“They both are,” Bobby muttered. “Always have been. You know, the only time my mom ever even…” He trailed off. “Never mind.”

“Spill,” Kimberly said. “Girls actually share their feelings, remember? You need to get into character.”

“Forget it,” Bobby snapped.

“Fine,” Kimberly said, giving his blonde waves a final fluff-out. “Okay, done. Just sit there, look pretty, and pretend to type once in a while. Make sure the sound is off, and that you keep your hands off-screen so he thinks you’re on the laptop. I’ll be over here typing the whole time, but don’t look at me, or it’ll be suspicious. Got all that?”

“Got it,” Bobby muttered sulkily, maybe chafing at the realization that his only part in the plan was to, once again, shut up and look pretty. He took the webcam and set it in front of him on the bed, unconsciously flicking his blonde hair out of his face with a very feminine gesture. Kimberly stationed herself out of sight and used Bobby’s laptop to start the video chat, careful to select the right webcam.

I did my best, she typed. What do you think?? Haha.

The blackmailer had obviously been waiting with bated breath for “Barbie” to make “her” appearance, because the reply was instant: Wow you look so sexy, you really did a great job, I’m happy lol. Pout those lips for me, beautiful! Please ;)

“He’s a fan,” Kimberly said. “Bobby, pout your lips for him, then give him a smile.”

A brief expression of revulsion crossed her ex’s face, then he reluctantly made his best “duckface,” fluttering his eyelashes at the same time.

The blackmailer was struck dumb for a second, then typed: Nice lol. What did you wanna talk about, beautiful? Better not be trying to wiggle out of our little arrangement ;)

Kimberly cracked her knuckles. Time to put her scheming brain to good use. I have to confess something, she typed. I actually like getting dressed up for you… I know I act like I hate it, but it’s because I’m not “out” yet… You saw me as Barbie and somehow you knew right away it was the real me, even though nobody else saw it. That’s, like, amazing… I wish you had just messaged me instead of blackmailing me, tho.

There was a long, almost unbearable pause. Bobby, blissfully unaware of what was being said, started toying idly with a strand of his wig, looking for all the world like a hot blonde all dolled up for a webcam date with her sugar daddy.

The reply came in a rush: I KNEW IT! Wow this is so great, beautiful, this makes me so happy, for real :D You’re taking hormones, aren’t you? Not that you weren’t perfect before lol.

Kimberly gritted her teeth. She had to steer the conversation away from hormones -- if it came up again in his messages to Bobby, the jig might be up. Yes, but please please please don’t even type that word, she typed. I didn’t get them legally and I don’t want to get in trouble if the FBI or something finds out. Just pretend I’m blossoming… Like any other girl… Please? Haha.

Lol my lips are sealed, beautiful, came the reply. I’m so so sorry I blackmailed you, I knew it was wrong but I just wanted to see you be yourself so badly :( I knew Barbie was the real you! I knew it!

You’re the only one who did, Kimberly typed. That’s why I always want to look my prettiest for you haha.

You’re not mad lol? came the blackmailer’s reply. Really?

Kimberly glanced over at Bobby, who was awkwardly adjusting the straps of his bra with a slightly pained expression on his face. “Pretend to type, dumbass!” she hissed. He flushed, but quickly lowered his hands off-screen again. As soon as he did, she played her masterstroke.

I was at first haha, she typed. But it was also kind of sexy? I keep wondering who you are and what you look like… Don’t worry if you’re not, like, super handsome, I don’t care about that stuff, haha. I just keep thinking about us actually meeting. Can we do that? Like, a date? Haha, only if you want…

The reply was not the instantaneous one she was hoping for. Instead, as Kimberly watched, the blackmailer wrote and backspaced what seemed like a dozen messages. Finally, a response appeared: Starbucks beside the bank this Sunday, 3:00 PM. I’ll be the guy in the red hat. Wear something sexy for me? Lol.

“Big smile, Bobby,” Kimberly said. “Big smile. This is it.” Bobby parted his pink lips and grinned as widely as he could. “Less big,” she ordered. “You look demented.”

You bet, haha, she typed. Oh my god, I can’t believe we’re doing this. This is so cool, haha. See you there, handsome ;) I have to go plan my outfit. Later!

“Blow him a kiss!” Kimberly ordered. “Quick!”

Bobby groaned, but did as requested, pouting his lips together and fluttering his fingers. Flushed with victory, Kimberly ended the video chat and turned off Bobby’s webcam. She deleted the chat history, to make sure Bobby never saw the word “hormones” and got curious, and closed the laptop. She had done it. The blackmailer might be able to cover his tracks electronically, but if they got him out in the open, in real life, he wouldn’t be able to hide his identity for long. All she would have to do is get her hands on his ID, and then the blackmailer blackmail could begin.

“Well?” Bobby demanded, folding his arms protectively across his boobs with a shudder. “What happened?”

“We’ve got him right where we want him,” Kimberly said. “You were a perfect little honeypot, Barbie. He thinks you’re meeting him at Starbucks this Sunday, and we’re going to nail him.”

“Okay, cool,” Bobby said, clearly excited despite himself. “So we watch from a distance, wait for him to show up, and what? Call the cops on his pervy ass?”

I’ll watch from a distance,” Kimberly corrected. “This guy might be lovestruck, but that doesn’t mean he’s a complete idiot. If he shows up and doesn’t see you, he’ll know something is going on. You’re the honeypot, remember?”

Bobby blanched. “Wait. You mean I’m supposed to actually go meet him? As Barbie?”

“That’s what you agreed to,” Kimberly said. “Come on, Bobby. We’re in too deep now to back out without pissing him off. And if we piss him off, you know what happens, right? Not only does he send the jerk-off video around, but he’ll probably send every single video you sent him as “Barbie,” too. It would ruin your reputation, like, for life.”

Bobby gave a low moan. “No skirt,” he said. “I’m not wearing a freaking skirt again.”

“No skirt,” Kimberly agreed. “Scout’s honor.”

High-Tops to High Heels: Part 6 High-Tops to High Heels: Part 6 High-Tops to High Heels: Part 6 High-Tops to High Heels: Part 6

Comments

Glad you are enjoying it! I have a couple other things in the works, but nothing ready to share yet. :)

Super happy to see you expanding KK and glad to subscribe! I do have a question though, are you currently working on any stories outside of patreon?

Nicegent42

I know and i have it, but this version takes it to a whole new level.

Nino Heđi

Melissa did a fantastic job on the images in the first version; it's just that I wanted to try it in my own style. :)


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