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Blackmailing Jane (Alessa and xxCloud26xx)

Alessa

Planetoid
Joined
Nov 15, 2011
Location
Alabama
Jane hunched over her computer, typing madly away in an attempt to catch up on her e-mails. She had taken an extra day off of work in order to enjoy a three day weekend, but she was paying for it now. Work was piled up on her desk, and her inbox was drowning with messages.

Tucking a lock of brown hair behind her ear, she nibbled on her lip absently as she responded about an upcoming legal case. She was 26 years old and quickly on her way to becoming one of the most powerful, potential parts of her legal defense team. She was proud of her accomplishments and focused her life on doing more. She had been a bit of a wild child growing up, never doing anything horrible but enjoying excitement, and now she just wanted to make money and earn a comfortable life.

She was careful to keep her appearance up, as that was an important part of success. She had a healthy, short body at 5'3", with pert 34C breasts and very little body fat from her hobbies of jogging and yoga. Her brunette hair hung past her shoulders, and her brown eyes tended to be bright and attentive.

A pop-up appeared on her computer notifying new mail, and it caught her attention. The delivery address was hidden, and she couldn't tell who it was from. Frowning in curiosity, she clicked on the e-mail to open it.
 
What a simple day it was for Jake. Nothing to do but lounge around in the cozy comfort of his apartment he shared with a female partner. Though it was unusual for people to room with people of the opposite sex straight after college, the two were actually very good friends during college so they decided to room together. Of course Jake had no problem with since he was a natural growing man, but there was something different about Jake that separated him from his peers… he was unbelievable cunning and smart; In fact so intelligent that he could have been a professor at a top rate institute in that area, but another odd thing was, he didn’t have a job.

Letting a long loud yawn escape his lips as he pulled himself up from the nice comfortable bed in an opposite room as his roommate, Jane, Jake sat up looking at a mirror that showed his reflection. Medium cut black hair that stopped midway above his ears, giving him a vintage, classy look all at the same time, as his crystal clear blue eyes peered at the image that looked back at him. He was about 5’9’’ though he was quite a slim guy weighing in at only a hundred-and-twenty pounds. Finally getting up out of bed, his long black pajama pants concealed the tan complexion of his feet, as he walked to the kitchen to prepare himself a cup of coffee.

“Ehhh, she must be gone,” he mumbled to himself taking a sit of coffee before sitting down at his lap top. An evil look stretched across his face as he opened up the browser to his email; now composing a mail to Jane that would change her life forever. A devilish smile conjured up from each corner of his face as he began to type furiously.

“Dear Jane,
I hope you enjoyed that wonderful party last Saturday, because I know I did. Though you probably don’t know I was there, and also I was the main attestant to your “actions.” These are some pretty nice pictures I would say haha. You have a nice figure hmm, and I guess somewhat of a C bra size if I could guess myself. Anyways my dear Jane, if you don’t want these pictures exposed you will do as I say.
~Yours truly
Anonymous<3.”

“Oh this is going to be great!” Jake exclaimed slamming his lap top shut as he walked to the sink to pour out his coffee. “Humans are so fun to manipulate,” he stated giving a wry smile to himself. To him this was all just a game that he had conspired on his own.
 
She read through the e-mail.. looking as it stated that they were at the party last Saturday.. and she immediately started blushing. He talked about knowing about her actions.. about the pictures that he had. And she would have to.. do what he said?

Oh my God!!!

There were pictures of.. of.. but no, surely there couldn't be! Wouldn't she have known if pictures had been taken? She decided it had to be a bluff.

Taking a deep breath she hit reply, and typed,
"I have no idea who you are or what you are talking about. You must have the wrong e-mail address, and I must say it is very wrong to attempt to manipulate women in the way you are trying. You need to learn to respect women more."

Reading through it once more, she clicked "Send" and tried to regain her focus. She was breathing fast, her skin flushed and a light sheen of sweat on her forehead.. surely it couldn't have been real.. It had the right name, but.. but surely it couldn't.. couldn't have been real. Could it?
 
“How gullible can they be?” He questioned himself as he let the faucet run to wash as he rinsed his hands under the soothing flow of the hot water. Turning the faucet off, he walked back to his laptop almost prancing now from excitement. “Oh what fun this is going to be,” smiling, he pried open the laptop, and the screen flashed on revealing the e-mail icon. Clicking it, the message displayed on his screen with a black crystal clear font.

Knowing that she was already going to deny the fact that this was true, the pictures of her secret naked rant at the party were already attached in an email he was ready to send. “What a predictable girl,” he thought to himself. Looking at the monitor with a dull expression, he propped his head in the warm palm of his hand as he quickly typed with one hand.

“My dear Jane, don’t fret as I won’t do anything with these pictures… that is if you listen to my commands. You see I have a few requests that I’ve been ordered to give you. I’m not sure what the purpose is, but I’ve been told to tell you that there will be a grey box in the fourth stall of the ladies restroom; my orders are to tell you to retrieve it and wear the clothes that are placed in it before returning to your apartment. Also my dear if you don’t believe me I think you’ll find the pictures in the attachment to your disdain. Anyways sweet heart, be a good girl now you wouldn’t want these pictures to get out to every computer in the world would you?
~Love Anonymous<3.”

With that, Jake shut his laptop and carried it with him to the couch where sat up parallel to face the oddly strategized game of chest, made up of five pieces, that sat on the table in the center of the living room. “What a brilliant plan,” he complimented himself before moving a black pawn next to the white queen.
 
It wasn't long before Jane's work was interrupted with yet another e-mail from an anonymous source. she wished she could at least figure out where in the world it was coming from! Sighing, she opened the e-mail.. and then promptly minimized it before anyone could see it! It was a picture of her naked.. at the party.. She flushed redder than ever as she turned her monitor for more privacy and called it back up again. The e-mail was short, telling her to do what she was told and no one would have to see the pictures. The fourth stall of the bathroom? What in the world was it talking about??

Curiosity got the best of her, and she locked her computer before standing up and smoothing out her gray skirt. She always dressed professionally and modesty, not wanting to use her appearance too much. It was important to not have people think she slept her way up the chain of command. Checking her white blouse, she approved her appearance and walked on her short heels to the bathroom to see if there was actually anything there. Surely there wouldn't be.

When she opened the door, there were no other women there. She paused for a moment at the sink, looking at herself in the mirror framed by the flowered wallpaper and wondered what she was doing. Why was she even entertaining this? The picture, of course.. that would ruin her reputation in one swoop. There was nothing illegal, but no one would ever respect her again. They would just think of that lewd image. How had someone even gotten it?? She thought she had known everyone at the party!

Finally, she couldn't put it off any longer, at the risk of someone else coming into the bathroom, and she took a deep breath and walked over to the fourth stall, her heels echoing in the room, and opened it. There, sure enough, was a gray box. Bending at the knees, the picked it up and opened it, looking inside..
 
Opening his laptop expecting another e-mail, he laughed as the screen was blank. Flailing his arms in the air he began to rejoice as if he’d gone crazy. “Ha, she must have already gone for the package. I guess she’ll be an easy one to use,” now returning back to his calm composure, he leaned over resting his face in the palm of his hand as he looked down at the chest board smiling. Adding another pawn to the table one space above the white queen, he laughed, “This is going faster than I planned.” Kicking his foot up against the arm of the sofa and letting his head use it as a pillow, he lay staring up at the ceiling wearing a wry smile that consumed his face. “I wonder what tonight’s events will unfold.” Knowing that she’d be wearing a demeaning dress home, it never crossed his mind as to how he was supposed to react.

Indeed Jake was at the party, but it he was wondering whether she knew who anonymous was. It’d obviously had to be a first had witness at the party, but there were only a few in the room at the time where she was naked. Shaking the thoughts from his mind, his ego boasted as he began to get cocky. “Of course she doesn’t know,” he thought frowning, “I made it seem as if there were two guys working on this project, she’d never assume it was me,” a soft chuckle escaped from his lips, “In fact she’s too much into a mental shock to even begin to analyze the possible suspects.” Now being over confident in his plan, he thought there was no way she’d know who did this.

Sitting up now, he flipped open his flip phone as he began to make a call. “Ring! Rin-!” The phone was picked up as a male with a deep voice answered it. Jake began to speak to the man in a calm, commanding voice. “I assume by now she’s taken the box. Slip they key under her desktop it should be the one with either a locked screen, or an e-mail minimized or in a separate tab, and don’t screw this up, or else I’ll make sure you don’t get what you want.” Abruptly, Jake shut the phone hanging up on the man giving him no time to reply. Resting his arms on the top of the sofa, he slouched as he watched the clock. “Times ticking Jane,” she was trapped in his game now, and it had just begun.

The gray box was framed with gold, and a key hole. Folded and wedged inside of the key hole, was a small slip of paper that read a set of instructions.

“Keep the box until after work, and keep it out of sight from your co-workers. Before you leave work use the back entrance, and make sure you change into it before you get in your car. If you don’t I’ll know, and I’m sure you wouldn’t want any ‘accidents’ to happen would you? Also be on your best behavior tonight I’m watching you
~Love Anonymous.”
The box contained a skimpy black maid outfit that would reveal every curve and show the imprints of every body part on Jane. It had a loosely laced back revealing her back and cleavage to the point that her breast would slip out if she wasn’t careful while walking. If she put it on I’d be tight around her ass complimenting her firm bottom and hour-glass shaped curves.

After being on the phone with his associate, he opened up his laptop again as he began to get ready to compose another e-mail to Jane. Typing in her email address, he couldn’t help smile at his ingenious of his plan.
“I’m sorry I forgot to mention about the key. I placed a key underneath your desktop; it’s the key to open the box. By the way my love put those clothes to good use, you wouldn’t want to waste that nice bust and body would you? Anyways hope you enjoy the attire I’ve made for you
~Your Master
Anonymous <3”
 
Jane picked up the gray box and examined it, noticing the key hole on one side. It was light, not appearing to have much of anything in it. If it was clothing, it must not be a full set of clothes. She quickly tucked the gray box under her arm and hurried back to her desk, trying to avoid her co-workers. Stepping back into her office, she set down the box and sat back down, wondering how in the world she was going to get the locked box open, not that she was eager to do so. Logging back into her computer, she noticed that there was another blasted e-mail from Anonymous.

She pulled it open and read the message from her new blackmailer. There was apparently a key under the box, and that she was to enjoy the attire that he made for her.. she assumed it was a he, anyway, but the package was found in the women's room. Could it be a woman? Her head was spinning trying to figure out who was doing all of this.

She peeked under her desktop computer, and sure enough there was a small golden key that looked like it would fit perfectly in the lock. A frown formed on her thin, red lips as she stared at it. Finally, with a trembling hand she unlocked the box and opened it. On top of a silky black fabric, she saw a note and read it.

She was supposed to keep the box hidden until after work, leave by the back door, and make sure she was dressed before she got into the car. They'd be watching? They were here at work, maybe? Oh God, did she work with this blackmailer? But that would make sense. The key under the computer..the package left for her to find! She found herself looking around the office, trying to see if anyone was watching her, but they were all hunched over their computers doing their work!

With a flush of deep red, she saw the outfit that was in the box. Some kind of fetish maid outfit. She quickly put it back in the box, looking to see if anyone saw her with it, and placed it in a corner under her desk where no one would see it. Could she even wear that?? She.. she had to. It would be highly embarrassing, but at least her pictures wouldn't get out after she did this and she could pretend it all never happened. Surely her roommate would understand. Maybe she could say it was a dare from a girlfriend, or she picked it up for a costume party at work. Oh, that was it! A costume party for work.. she would go for that excuse.

She opened the e-mail program, and hit the reply button. "I'll do this to keep the picture from getting out, but you're no master of me. I have no intention of enjoying wearing this ridiculous get-up, but if it gets your juvenile, masochistic attention off of me, I'll do it. You are sick and need to get help."

She pressed the send button and felt better after venting some of her anger.

At the end of the work day, she leaned down to get the package and made her way to the bathroom. She peeked under the doors of the stalls to make sure that no one was in there, and placed the doorstop on the door to make it hard to open. She didn't want to be interrupted here. She unzipper her gray skirt and unbuttoned the side, letting it slide to the floor as she stepped out of it. Next, she unbuttoned her white blouse and folded it on top of the skirt. Standing in her white lace bra and pink, cotton panties she took a look again at the outfit, pulling it out of the box. There wasn't much to it at all. It looked like it would even barely fit.. she'd have to squeeze into it.. There wouldn't be a way to wear it with her bra and panties, either. Maybe a thong, but not what she was wearing. Groaning, she hooked the waistband of her panties and pulled them off before unclasping her bra as well. Nervously, she looked around still wanting to make sure there was no one there. Finally, she worked on squeezing her trim body into the tiny outfit.

After a few minutes, she was flushed from the effort but finally dressed. She eyed herself in the mirror and blushed hotter still, embarrassed at how she looked. Her breasts practically spilled out of the top of the corset-like top, making her actually breathe in shallow breaths unless they fell out altogether, possibly humiliating her even farther. She liked to be modest and professional.. she honestly had no idea what had gotten into her at that party. She had enjoyed a few drinks, some conversation, and then she was naked in a room of several men with, apparently, others watching and even taking pictures. Oh, if she had just skipped that party!!

The skirt was barely a skirt, hanging down just to the very top of her bottom. It was very tight, accenting her curves and she knew if she would bend over even a little, she was going to show far more of her body than she wanted to.

There was nothing for it, though.. she had no choice. At least this would all be over soon. With a deep blush and constantly looking around for anyone watching her, she walked carefully out to the back entrance of the building. She had to take small, mincing steps that made her hips swing lewdly while breathing shallow breaths, her arms only moving slightly to try and keep the outfit where it needed to be, and she was sure she looked like someone truly wanton. God, why was she doing this?

Going out the back entrance, she had to walk fully around the building in order to get to her car. She guessed this was where her blackmailers were watching her, so she couldn't cheat. She could never live with herself if those pictures got out. 'Just get through it. Just get through it,' she kept thinking as her heels clicked on the pavement.

Finally, she got in the car and climbed in, skirt riding high around her waist leaving her essentially unclothed below. She drove quickly, actively trying not to look at any of the other drivers that were bound to be getting a show, and with huge relief she pulled into the driveway, unlocking and entering the house. With any luck at all, Jake was upstairs and wouldn't see her at all. She stepped into the kitchen, prepared to race to her room to undress.
 
The whole time he was observing her actions secretly, by the hotwired cameras that served as his eyes along with his associates. All this time he’s been able to watch not just her moves, but the moves of people around her, and of course this was staged by him; the perfect work of a mastermind was just beginning to unfold, but to his dismay, his casual viewing was disrupted by the pixilated icon that, once again, filled the top corner of his screen revealing the e-mail notification.

“Another e-mail already?” He questioned himself aloud, not expecting to have received a reply so soon from his little puppet. “Dammit, I thought I explained everything that she needed to know, and how did I not see her typing that e-mail?” Now pondering, he opened the message that would hopefully clarify his confusion. As he read it he couldn’t help but laugh at the little attitude she showed. “You have guts women,” he said calmly to himself before resting his hands on the black, plastic keys of his laptop replying to her message.

“Ha, I like you Jane. You have some courage there showing your little flair of rebellion, but I think I’d be to your benefit if you change. You see, you’re already on strike one since you didn’t obey my commands completely. Hopefully your curiosity doesn’t matter to you as much as your reputation does; for I saw you trying to sneak a peek at the box to see what was inside beforehand. Thing like that will get you in trouble my love, especially if someone was to see that. Just imagine all the questions they’d have as they see your opening a package with such a “prestigious” dress. I gave you specific order for a special reason because as yourself, I care about you deeply too Jane, and I would hate for your reputation to get ruined.
~Anonymous
P.S: Don’t you dare remove those clothes when you return home, and since I’m being lenient, you have to wear the clothes every day before and after work, and if you fail to millions of people will have a myriad of pictures to select from, with you being the star. Oh by the way the dress looks great on you, it really compliments your figure.
~Love
Anonymous”

Shutting his laptop, he strolled to the kitchen gallantly with his head held high from confidence, lapsing over the brilliance of his plan before stopping at the island in the kitchen. “I suppose this is a good time to celebrate,” he said to himself opening the cupboard, taking out a slender green bottle along with a glass cup. Knowing he’d have to finish the bottle quickly, if he wanted his money’s worth of alcohol, he drank glass after glass indulging himself in the poisonous solution.

“Ahhh man, this is great!!!!” Now partially intoxicated his senses, along with his intellect, begin to dwindle as the alcohol took over. Down to the last glass, bottle empty and cup filled to the brim, the bottle was tossed aside and he lifted his arm to drink, before he was interrupted by the intrusion of the door. Fixing his gaze on the women now entering the luxurious apartment, he paused as his eyes went blank letting a drop of alcohol slip to the floor before he set the cup down on the marble countertop of the island. Turning around to completely face the girl, a conniving smile arouse from each corner of his lips prowling from uncontrollably to each end of his lips. “Well Jane it is my birthday? Or are you just strewing with me?” Still have drunk; partially incoherent with his surrounds, approached the girl getting a bit too close for comfort. Letting his finger run down the front of her torso, he stopped it after it traveled the hill of the perfectly round mound of delicate skin on her chest. She was still covered, partially, but he could feel every inch of skin as if it was bare. Of course this was not his original plan, but he was so intoxicated the alcohol took over his persona. Now closing in on her, he used his body to force her against the silver plate of the metallic fridge. “Are you even wearing anything down there?” He questioned. His breath was tart now with the wafting smell of alcohol as he spoke. Reaching his hand to gently brush the smooth skin of Jane’s thighs, he rubbed his hand along her inner thigh confirming his assumption

Though he greatly enjoyed the whole process, he failed to think about the consequences of his actions. How would she respond to all this? After all, this women was a women of integrity, always doing the right thing, but messing up here and there along the way. And also the biggest factor that played into his actions was his plan. Evidence was scattered everywhere from his lap top to the wineglass still lingering on the counter it once laid. He would surely not have an excuse for that… especially intoxicated as he was. It was amazing how much trouble one drink could brew up as he continued reprehensibly playing with her, not caring for her thoughts. And the worse question of all… What if she found out he was her blackmailer…?
 
Jane saw the last e-mail from Anonymous just as she was leaving the office, anger building in her as it told her she was in trouble for peaking in the box. How was she not expected to look ahead of time?? Then it said she couldn't remove the clothes at home and would have to wear them every morning and night! This was getting ridiculous! She had to find a way to get this to stop.

She finally got into her house, and her room mate Jake was drunk. He rarely was drunk, so this was definitely different to her. He was a very smart man, and had never seemed creepy or weird to her. In fact, he would be the only man she'd let herself be roommates with without being married.

But he was very drunk. Before she got a chance to get through the door, she noticed that he was eyeing her. She looked down at her own outfit and blushed hot. She could understand, since she was dressed so wantonly. Dress like a slut, get treated like one.. she had always believed that, and tried to dress modestly to avoid it. Now, here she was as he flirted with her, moving and letting his finger slide down her breasts and stomach, and then he stepped closer to her, his strength surprising her, and he pressed her back against the fridge, his body shoving into hers as he asked if she was wearing any.. any panties.. and then he slid his hand against her inner thigh and she knew he could tell she wasn't wearing any!

She couldn't take it anymore, pushing to get him off balance and sliding away from him. "You're drunk!" she exclaimed. "You wouldn't do this sober, even if I am.. am dressed this way. This horrible, horrible way! But.. but you've never done this before! You can't do this! Please.. please just sleep off your drink and.. and we can pretend this never happened, ok? We can just pretend that!" Tears streamed down her cheeks as she ran to her bedroom, her breasts falling out of the top and her smooth bottom revealed as she moved quickly, unable to control the horridly revealing outfit. She closed the door, leaning against it as her breath came in fast gasps.

What had happened to her sweet roommate? It had to be this outfit she was wearing. That horrible outfit. But what could she do? She knew she was going to wear it in the morning again to go to work. She knew she didn't have a choice.
 
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