My Sister's Bully, My Bully

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Caitlyn's little sister's bully sets her sights on Caitlyn.
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CopyCat13
CopyCat13
240 Followers

Unlike the vast majority of recent college graduates, Caitlyn actually had her life together. Despite the fact that she was only a year out of college she was already an associate at a respectable advertising firm and on the fast track for advancement. Luckily for her, the company put a lot more stock in ambition and talent than in how long someone had worked there so she was able to advance quickly. When she'd just been an intern, she'd come up with a brilliant advertising campaign for a local restaurant which landed her the job in the first place and a few months later another brilliant idea earned her a promotion. In fact she'd already been promoted over one of the women who'd been working there for 5 years. Caitlyn knew that as long as she kept churning out new ideas she'd be a top manager in the company in only a few more years.

The only down side to a company that would let her advance so fast was that she could be knocked down again just as fast. When every brilliant campaign idea can earn you a promotion and a pay raise any bad campaigns can easily get you demoted or even fired. Cailyn knew all this of course so she worked extra hard and stayed late to fine tune and polish all her ideas before presenting them to her boss. She'd gotten a bit of a reputation for never letting anyone know what she was planning or even giving hints until she revealed them to her boss.

Outside of work, Caitlyn was also a lot more together than most 23 year olds. She had a wonderful boyfriend named Mark who was in law school. They lived together and while she was paying for his schooling, she knew that in a few years he'd be the one making the real money. Even so, Cailyn wasn't above flirting with men in clubs or at bars or even at work if it meant she got something out of it. At work that might be a favor but in the clubs a free drink or a nice dance or even attention from a hot guy was enough.

Caitlyn was always fastidious with her wardrobe. She knew what looked good on her and always did her best to impress. She knew her big butt was what got the most attention so she tried to dress in tight skirts and pants to show it off as often as possible. Her chest on the other hand was sadly lacking. Every day Caitlyn wore a heavily padded push-up bra to give the illusion that she had a respectable C-cup. In fact, only Mark and a handful of her friends from college had ever seen her without her padding so almost everyone believed she was a C-cup. Caitlyn was so scared of anyone else finding out that she even went to a gym more than an hour away so that no one she knew would see her without the padding.

While it may seem odd to some people, Caitlyn had come to associate her self-image with her chest. All throughout high school she'd been bullied for being smaller than the other girls and it had killed all her self-esteem. In college, she started stuffing her bra and found that she not only got a lot more attention from the boys but everyone seemed to take her more seriously. Her teachers started paying more attention to her and her grades noticeably improved. Her padding made her feel more mature, more like an adult, and more importantly everyone around her started treating her that way as well. It wasn't long before she replaced almost all of her bra with ones with extra padding so she wouldn't have to stuff every day.

Caitlyn had been recommending to her little sister Stephanie that she start stuffing her bra as well because Steph was just as flat as her big sister but so far she'd refused. Caitlyn always got sad whenever she talked to her little sister. Stephanie was so much like her right down to the part where she was constantly bullied. Caitlyn knew that if Steph just started stuffing her bra and got some confidence then the bullying would stop and she'd be much happier. But Steph never took her advice.

That's why Caitlyn was thrilled one day when her boss handed her a new project to work on. Caitlyn was going to be in charge of running a new advertising campaign for the local college that she'd graduated from and that Stephanie still attended. Her boss also handed her a resume and told her that she'd be working with an intern from the college. Caitlyn was shocked when she looked at the resume and realized that it was Lisa Silvers, Stephanie's freshmen roommate and her biggest bully. Caitlyn realized that this was a golden opportunity to get a little well deserved payback on behalf of her little sister.

Caitlyn spent the rest of the day smiling mischievously as she imagined all the things she was going to make Lisa do. And best of all, she would be able to excuse it all as actual work so if Lisa complained too much she would probably get fired. And even if she didn't get fired, her internship was only going to last a month after which Caitlyn would be sure to give her a horrible review so she wouldn't stand a chance of getting a job anytime soon.

When she got into work on Monday, Caitlyn finally met Lisa Silvers for the first time and immediately disliked her. The company she worked for had a very casual dress code and Lisa was already taking advantage of it. She came in to her first day of work in skin-tight jeans and a low-cut blouse. Honestly, her outfit wasn't all that inappropriate, Caitlyn realized but her breasts we huge and her figure basically perfect so literally every head in the office turned to watch her. Even the women.

Caitlyn had absolutely no trouble seeing how Lisa would bully her sister Stephanie. From her own personal experience, Caitlyn knew that the girls with the biggest boobs and the hottest girls tended to have a lot more confidence and that naturally made them act like alpha females. And then they naturally started to bully the girls around them. Caitlyn hated it but she knew it was inevitable. If only Stephanie would take her advice and start stuffing her bra maybe Lisa would leave her alone.

From the moment she saw her, Caitlyn couldn't wait to go to work on Lisa. She was looking forward to piling so much work on her that it would crush her. And after giving her the initial tour and filling out the mountains of paperwork she needed to get started, Caitlyn started piling it on. She made Lisa do all the grunt work not only for her, but for all her co-workers as well.

But to Caitlyn's utter surprise, Lisa was extremely hard working. She managed to do everyone's grunt work quickly and efficiently and still had plenty of time left over to get some real work experience as well. She talked and laughed with all the employees including Caitlyn and proved herself to be extremely intelligent and quick witted as well. And she did it all with a smile on her face.

By the end of her first week, Caitlyn had almost forgotten that she was supposed to hate Lisa. She was so charming and charismatic that even Caitlyn had fallen under her spell and was starting to consider her a friend. She stopped just giving Lisa the grunt work and actually let her work with her on the new campaign she was planning for the college. They made a great team and before long Caitlyn started to think that together they could easily rise to the top in the company.

Caitlyn hadn't completely forgotten that Lisa had been bullying her little sister for years but she was so likeable that she actually started to consider that maybe Stephanie gave her a good reason to be a bitch.

They were scheduled to present their plan for the advertising campaign on the Monday of Lisa's third week of work so the Thursday before that Caitlyn planned on pulling an all-nighter to finish the plan. That would give them all day on Friday to fine-tune and polish it all so they'd be ready to present on Monday. She mentioned her plan to Lisa at work and she immediately offered to stay up with Caitlyn to help her finish. Caitlyn gladly accepted her offer and gave Lisa her address so she could come over after work.

Lisa was the perfect house guest and was unfailingly polite and appreciative about everything. When she met Mark she was nice and started to flirt a little but then seemed to realize that it was inappropriate and stopped. Mark had an early test in the morning though so he retired to the bedroom to sleep early while the girls stayed up working in the living room.

Around midnight, Lisa suggested opening a bottle of wine and shortly thereafter the girls were starting to get tipsy and giggly. They opened a second bottle as they worked and the alcohol seemed to be helping. The ideas were just pouring out and they continued to work all through the night and right through a third bottle of wine.

Exhausted, Caitlyn finally fell asleep on her couch around 5 in the morning intending to just take a 2 hour nap before getting up for work. But apparently she slept through her alarm and the sounds of Mark getting up and leaving because when she finally woke up, it was already noon and her apartment was empty. She woke up incredibly hungover and strongly considered just calling in sick as she'd already missed half her work day anyway but she knew she had to finish putting the final touches on the presentation so she got up and went to her bedroom to get ready for work.

She was shocked however when she opened her underwear drawer to find that almost all of her bras were missing. She'd already done laundry for the week so she knew they weren't dirty so someone must have stolen them. All that was left in her drawer were her sports bras and her last remaining unpadded bra. Caitlyn decided she'd just keep wearing the bra from the day before only to realize she wasn't wearing one. She knew she'd had it on last night though so someone must have taken her bra off while she slept and then put her top back on over it.

Caitlyn was outraged but her headache was making it hard for her to concentrate on anything so rather than try to think of a solution, she just took a quick shower and got dressed in her unpadded bra and went to work.

She got into work a little after 1PM ready to suffer through an agonizing day of work hashing out the finer details of the presentation she would be giving on Monday but as soon as she got to her desk her bossed stopped by. He informed her that overnight Lisa had gotten a stroke of genius and planned out the entire advertising campaign by herself. Before Caitlyn could speak up to tell him that she'd actually done a lot of the work her went on to tell her that Lisa had called the college and they'd had their meeting earlier that day. She'd wowed the representatives from the college and they'd gone out to lunch to celebrate. They'd be back to hash out all the details later.

Caitlyn was so shocked by all this that she didn't even notice that her boss kept glancing at her chest with a confused look trying to figure out why she looked so much flatter than before. Caitlyn wanted her boss to know that the idea had been hers and that she'd done most of the work but he didn't want to hear it. In his mind, Lisa had met with the clients and sold the idea so the idea was hers no matter who'd done the work. Before he leaves, he takes one final shot and mentions that if Caitlyn had been in to work on time she could have shared the credit with Lisa.

Caitlyn spent the next hour fuming at how Lisa had screwed her. And the worst part was, she knew she was to blame. She should have known that the devious, manipulative girl who'd been tormenting her sister for years would try to pull something like this but she'd let her guard down. Lisa had played her expertly and left Caitlyn looking and feeling like an idiot. Caitlyn got so enthralled with mentally beating herself up for being so stupid that she completely forgot about her bra situation so when Lisa and the clients got back from lunch she didn't even think to hide her chest from view to save her image.

The basic idea behind their advertising campaign was to take 2 students, a freshmen and a senior, and feature them in their pamphlets and commercials to show how much students would grow and mature over their 4 years at the college. Lisa had taken it a step further and when she pitched it to the clients she suggested that she and Caitlyn be the models since they'd both attended the school.

Caitlyn didn't want to do that but she knew that the only way to save face and keep her job safe was to just roll with it and act like she'd know about it the whole time. Caitlyn, Lisa and the clients sat in the conference room for over an hour hashing out all the details but the only one that really mattered to Caitlyn was when the clients mentioned that she'd be posing as the naïve freshmen while Lisa would be the mature senior.

When they first mention that, Caitlyn tried to speak up, "But I'm older...I graduated last year..."

Lisa just gave her a condescending look and glanced significantly at her chest reminding Caitlyn of her lack of padding. Caitlyn blushed at that and quieted down while Lisa smirked and the clients chuckled. Composing himself, one of the clients said that there was already a noticeable difference between them but that they wanted to maximize it for the campaign so that it would have a bigger impact on potential students. To that end, her cut a check to Lisa personally so she could go out and get her hair and nails done along with wardrobe for the 2 of them for the photo shoots.

The clients were treating Lisa like she was in charge instead of just and intern and Caitlyn is horrified to realize that they're right. Lisa had completely taken control of the situation and she'd have to scramble just to come out of this whole thing with her job and dignity intact. With the details hashed out and their meeting concluded, Caitlyn and Lisa decided (Lisa informed Caitlyn) to go to the mall after work to get their new wardrobe.

Caitlyn spent the rest of her workday wallowing in self-pity and suffering through her hangover so that by the time she got off work, she was feeling truly miserable. Lisa and Caitlyn drove separately to the mall where they met up and headed to the salon.

Lisa got her hair styles and her nails done while Caitlyn got her hair dyed blonde to match Lisa's. That was one of the details they'd hashed out that they wanted Caitlyn to make people think of a younger version of Lisa. Caitlyn thought she might look good as a blonde and since it was being paid for she was perfectly fine with that part. But then Lisa told Caitlyn's stylist to cut Caitlyn's hair short and put it in pig-tails. Caitlyn tried to protest but Lisa just reminded her that the clients wanted her to look as young as possible. The stylist just smirked and did as Lisa said without ever stopping to consider Caitlyn's protests.

When they were done at the salon, they walked through the mall toward the department store to get them both a few new outfits to wear for the photo-shoot. Caitlyn was dreading what sorts of outfits Lisa would pick for her in order to make her "look younger" so she didn't notice what they were walking past until Lisa stopped.

They were outside a designer underwear store and Lisa insisted on going in and getting some new underwear to go with their new outfits. They went in and Lisa found a sales girl to request a fitting. The girl brought them both to a large changing room and told them both to take off their tops and bras so she could get an accurate measurement. Caitlyn was a little embarrassed to be stripping in front of Lisa and a complete stranger but since it was the girl's job she figured it wouldn't be too bad.

The girl measured them both and informed them that Lisa was a very respectable 34DD whereas Caitlyn was a humble 32A. Caitlyn blushed at that while the sales girl chuckled and whispered something to Lisa that made them both laugh. Once they calmed down a bit Lisa said, "Yeah that sounds awesome, let's try that and see how it goes. Could you bring us a couple actually?"

Caitlyn had no idea what they might have said but the sales girl returned shortly bearing a few things for them both to try on. For Lisa, she has an assortment of sexy, lacy bras and matching panties for each of them. For Caitlyn...she has a couple training bras and panties with little cartoons on them. Caitlyn's first thought was that she hadn't even know that the store carried underwear for little girls before the reality of the situation set in and she realized that the little girl underwear was for her.

She's so shocked that it takes her a few seconds to find her voice but once she did she started yelling at Lisa and the sales girl that it wasn't funny and to bring her some real underwear. They both snickered as Caitlyn kept yelling at them for a few minutes until she ran out of steam. Once she did though, the sales girl remarked how cute she looked throwing her little temper-tantrum. Caitlyn could feel her cheeks burning both from anger and humiliation at the whole situation as well as feel tears in her eyes before suddenly realizing that her exposed nipples were rock hard. Lisa and the sales girl kept laughing as Caitlyn crossed her arms to cover her embarrassingly small chest.

Finally though, Lisa offered her a deal. If Caitlyn tried on all the underwear the sales girl had brought her and a single piece of it didn't fit, then Lisa will sign over the entire $1000 check to her and furthermore allow Caitlyn to pick her outfit for the photo-shoot. However, if every single piece fit her, then Caitlyn would have to wear them and stop complaining.

Caitlyn considered the deal carefully while looking through the underwear the sales girl had brought. Some of the pieces looked pretty small and she was pretty sure that at least one of them wouldn't fit her. After nearly a minute of silence, Caitlyn agreed to Lisa's deal.

Lisa and the sales girl both smirked as they watched Caitlyn try on each and every training bra and pair of panties. A few of them were a little tight but all of them fit her. Realizing her defeat, Caitlyn hung her head as Lisa pulled off all the tags and handed them to the sales girl along with the underwear Caitlyn had come in. She told the girl to ring up all the underwear and to "please throw out these old ugly things". Caitlyn would be wearing some of her new underwear out of the store.

Caitlyn sat on the bench in a stunned silence as Lisa tried on all the underwear the sales girl had brought for her before selecting a couple pairs to buy. Once they were both fully redressed, Lisa and Caitlyn left the changing room and stopped by the checkout counter to pay for Lisa's new underwear and thank the sales girl for all her help. The sales girl couldn't hold back a laugh at the look on Caitlyn's face as they left and Caitlyn blushed deep red all over again.

They proceeded to walk through the mall to the department store to pick out a few new outfits for their upcoming photo-shoot. Luckily Lisa had mercy and selected a loose fitting pair of jeans with a plain, sky-blue top, and a knee length dress. Nothing too embarrassing and Caitlyn knew that the outfits would prevent anyone from seeing her new underwear, but they also made her look like she should be in high school. While she was humiliated by it, she knew that it was exactly the look her clients were looking for.

Carrying their bags, Lisa and Caitlyn left the mall and started heading toward their respective cars. Caitlyn was loading her bags into the trunk of her car when Lisa grabbed her arm and turned her to face her. Caitlyn was surprised by how strong Lisa was, she tried to pull away as hard as she could but Lisa held her arm in place without any apparent effort.

"Oh and one more thing before you leave, don't even think about trying to get out of wearing your new clothes either. If you show up to work in anything other than what we bought today I'll bend you over your desk and spank your bare butt right there in the office. Understand?"

CopyCat13
CopyCat13
240 Followers
12