Chapter 3

Cindy Evergreen

Every year despite its numerous challenges, enrollment within the Free Use program always tended to max out. The reason why, however, is more obvious than one might think. Even after the total capacity had been more than doubled since its initial creation, up to twenty thousand from the initial ten, there still wasn’t enough space. The program only has a limited number of slots available after all, and better a single year of probation than a full prison sentence.

Thus, as Cindy Evergreen stepped out of her car, a brand-new current release Mercedes, it was only with a minor semblance of pride that she slung her business jacket over the bright red collar wrapped around her neck. A collar that would have gone to some other poor and poverty-stricken criminal in need of rehabilitation had she not paid her lawyer an obscene amount of money to reduce her twenty-year charge of insurance fraud to a mere twelve months of having to wear a stupid little ring around her clit. She really had to go and thank her old acting professor for that. The jury had bought right into her sob story of having been tricked into it by her boss, who as a result of her confession was now rotting away in a maximum-security cell with a government issued chastity cage secured around his dick.

The expression on his face as he was led away by the bailiff was priceless. Thirty-nine years in total, twenty from his sentence and nineteen from hers. Well, as the saying goes, no honor among thieves. A shame really, though it wasn’t as if he was ever that much of a friend. She had spent way too much time on her knees and underneath his desk to ever miss him. Three inches long at best, and that was only when he was right about to ejaculate into her mouth or onto her breasts. Which probably explained why he never bothered to fuck her once in the ten years they had worked together ever since she had graduated from college. Nothing but his endless daily blowjobs and the occasional remote-controlled vibrator shoved up her pussy in return for helping her climb the corporate ladder so they could both get rich.

“And to think that he even told me he wanted to marry me after it was all over,” she scoffed under her breath, “As if he even had the slightest idea of how bad he smelled.”

Making sure that her car was locked, Cindy picked up her purse to walk down the street. The office building was only a couple of blocks away from the parking garage, and the sharp click of her heels echoed smartly off the pavement. Prim and proper, she held her head high, just the way a lady should be. Especially one who had fought her way up to her current position as the head of the marketing department with nothing but her wits and a smile on her face. The fact that she had built up a reputation for weeding out the competition beforehand was just a coincidence. It was hardly her fault that the company’s sexual harassment policies were so strict. And if she just so happen to leave an extra button undone on her blouse every now and then and people just so happen to stare, then who could say it wasn’t her right to dress the way she pleased?

The front doors of the building greeted her, Eric & Ericson, and she strolled into the lobby as she always did. A quick swipe of her keycard, a tilt of her head, and she looked around the open room almost as if she owned the place. And why not? She was Cindy Evergreen after all, business queen of ice. She had fought the law and had even managed to win back her court fees.

Audentes fortuna iuvat, she thought sweetly. Fortune favors the bold. If the police couldn’t stop her, then who else even dared?

Or at least, two weeks ago that would have been the case. Today was different, and as she walked over towards the front desk and the elevators that lay behind it, she found herself staring straight into the face of a certain Jeremy Winston, security guard and receptionist, who was at the moment the last person she wanted to see. And who had very quickly become the bane of her existence ever since she had been enrolled in the Free Use program for the Correction of Convicts.

“Morning, Ms. Evergreen,” he said with a smile, “Busy schedule this week?”

“Fifth floor please,” said Cindy curtly.

Even as she said that though, the man made no move to stand up as he leaned back in his chair.

“Oh, the one with the conference room,” he said, “In a rush for a meeting today, are we?”

“Yes, I-…,” said Cindy.

“I wonder if the CEO is going to be there,” he said, interrupting her, “You know, the woman with the huge tits. I see her every now and again when I’m checking out for the night shift. You’re important enough for that, right? You’ll have to tell me all about it afterwards. Sometimes, it’s almost as if she doesn’t even know that I exist down here.”

He looked up from behind his desk, and she shot him a glare that would have sent even the most senior of managers scurrying out of her office. How dare he treat her like this. In return, however, all she got was the slightly bored expression of a man who couldn’t even bring himself to care. The look of the most common denominator, whose only raison d'être was the fact that they got paid.

Useless slackers, the entire lot. Her disgust wasn’t made any better as the man picked up the metal detector wand from besides his computer and waved it almost as if it was a fan in front of her face.

“Anyhow,” he said with a yawn, “That’s enough for today. You know the rules. Clothes off, feet apart, and down on your hands and knees.”

“And if I don’t?” said Cindy scowling.

“Then I’m afraid I won’t be able to let you pass,” he said, “You didn’t expect to just waltz in here and do as you please, did you? There are regulations to follow, you know. Surely you can’t expect to be above that.”

He smiled again, his eyes lingering this time across her chest, and she grit her teeth as she stared down at him. Strictly speaking, that last part wasn’t exactly standard procedure as outlined in the company guidelines. Neither was any of what came before that when it came to standard full-time employees. In this case though, things were only just ever so slightly different due to the bright red collar wrapped around her neck. Even if it was only a legal technicality that existed only because of her sentence.

“You do know I work here, right?” she tried.

The only response she got, however, was another laugh as if he hadn’t just seen her come in every single day from nine to five for the last week.

“Technically you do,” said Jeremy, “But technically you’re also a criminal on probation. As such, it’s my job to make sure that all guest visitors aren’t hiding any contraband in… well, let’s say in any surprising and unconventional places.”

He waved his hands about as if in apology, his eyes never once moving away from her front.

“And besides,” he said with a grin, “I’ve been staring at you for the better part of ten years ever since you came in as an intern. Don’t you think it’s finally about time for you to show me what you got down there? It’s only polite you know, given your reputation for being so… receptive.”

If it weren’t for the fact that she really would go to prison this time, she would have slapped him right then and there. Cindy fumed. Even when coming from someone like him, the words had stung more than she had expected. Taking in a deep breath, she looked up at the clock and sighed as she counted down the minutes she had left inside her head. Less than half an hour until seven, and her meeting was due to start in exactly fifteen minutes after that. At least the lobby was empty at the moment except for the two of them. From past experience, she really didn’t want to wait until the rest of the company arrived.

Slowly, she reached up to undo her blouse, her fingers fumbling for the buttons before moving down to her waist. A short pull of the zipper, and she shivered as her pencil skirt came away to leave her standing there in only the black lace of her bra and her panties. Lace that cost more than what the man sitting across from her made in a week. The cold air of the building blew across her skin, and she tried not to notice the way her nipples poked up from underneath the fabric.

“That’s it,” said Jeremy, “Take it all off. Just like that.”

“You know I can have you fired with just an email,” she said weakly.

It was an empty threat and she knew it. Halfway through taking off her clothes, her arms were currently held all the way behind her back, and she winced as the man leaned forward to give her left nipple a twist.

“Sure you can,” he said, moving on in the next moment to give her other side the same treatment, “Just like how a simple phone call is all I need to have you arrested again for non-compliance. You wouldn’t want that now, would you? Unless, of course, you rather enjoy the thought of sitting around in a jail cell with a chastity belt locked around your waist.”

Another pinch and he moved down to trace over the soft outline of her slit. Cindy couldn’t help but gasp as his fingers found the tiny hidden nub of her clit hidden in between. Even through the thin layer of her panties, a single touch across the delicate organ and it felt like her entire mind had been reset. Doubly so when she currently had an orgasm suppressing ring wrapped around the base. An entire year of not being able to cum, all while she had to bend over and spread her legs for anyone that asked.

Already at two weeks in and it was starting to get hard to sleep. She tried not to think about it. The longer she spent the longer it would take, and she reached down to pull away the last bit of protection she had before stepping out of the garment and setting it aside. Spreading her feet apart until her pussy was on full display, she slowly bent over to place her hands against the edge of the desk.

She was ready now. Standing up at last from his chair, Jeremy walked over to look down at the smooth and unblemished skin of her rear.

“I didn’t know you were shaved down here,” he said.

Cindy blushed.

“Well, I am,” she said, “Anything else?”

He ignored the jab, choosing instead to run his hands over the sensitive skin of her thighs and up in between.

“Which one today?” he said.

“Does it even matter?” she sighed, “Just get it over with already.”

Staring down at the marble pattern of the floor, she shivered against the feeling building up between her legs. Jeremy smiled, and she could practically see him leering down at her body as he spread apart her cheeks. First her pussy, his hands brushing across the sensitive folds of her labia, and then her anus as he pressed down against the tightness of her ring. A dull point of pressure, and then gathering up some of the natural wetness that was already starting to leak out of her, he slowly pushed the very tip of his finger in.

“So smooth,” he said, watching the muscles of her opening stretch, “Have you ever thought about letting anyone use you back here?”

Cindy clenched her jaw in response, resisting the urge to spit a scathing retort back at him. Don’t think about it, and it would be over before she even realized it. Tightening her grip, she tried to focus on the sharp edge of the metal underneath her palms, grounding herself in the sensation. The fact that she had to put up with this for the entire next year was already bad enough as is. The last thing she needed to do now was to give him the satisfaction of seeing her come apart in front of him.

They had only just started though. A second finger joined the first, opening her up even further as his other hand moved down to massage her clit, and she stumbled forward a little as he pressed her up against the desk. Another minute of absolute wrongness, the feeling of something entering here where nature never intended, and she heard him drawing down the zipper of his pants. It was all she could do to not clench. Especially as she felt the tip of his member press up against her labia and her pussy.

“Tell me you want it,” he said.

“Screw you, asshole,” said Cindy.

A pause as he seemed to think about it.

“Are you sure?” he said.

“Wait, I didn’t-…,” said Cindy.

The irony wasn’t lost on her as he suddenly shifted himself upward to press against her anus instead.

“If you insist,” he said.

He thrust his hips forward and she grit her teeth. Despite his meager attempts to at least loosen her up first, the sudden movement of his dick against the tight ring of her backdoor had hurt more than she expected. As he began to speed up, however, it wasn’t long before the feeling of pain gave away to pleasure as her pussy started to leak. Damned ring, always keeping her trapped right on the edge. A second and then a third thrust, and already she could feel the familiar heat of arousal building up inside her suddenly empty sheath.

Groaning, she tried to ignore it. Two weeks of being fucked every day without even the slightest hint of relief and the feeling wasn’t made any better by the way her clit stood up on end. Biting down on her lips, she tried to push up her waist. In the short term it would only make the frustration even worse, but the faster she could get him to cum, the faster she would be able to get back to her office and get herself cleaned up before her meeting was due to begin.

Jeremy, however, seemed to be in no hurry to finish. His rhythm remained torturously slow, each thrust aimed in just the right way to press down against her g-spot through the thin barrier in between.

“That’s it,” he said, “Take it like the backstabbing bitch you are.”

Cindy grit her teeth so hard she thought they might shatter. She would never give him the satisfaction of watching her beg, but even as she braced herself against the edge of the desk, it was as if she was fighting back against the relentless tide of the ocean with nothing but her hands. She wanted to cum. No, she needed to cum. If she didn’t get an orgasm right here and now, she was going to go insane.

Then, another thrust into her rear, and he just had to reach his hand around to play with her clit.

“Getting close?” he teased.

Her body responded despite her mind's protestations. Inside her pussy, the slowly accumulating mass of frustration that was her orgasm felt as if it was trapped behind a thin layer of rubber stretched to its limits. A single push against the surface, and then it would burst. Except that even as her arousal dripped and dripped and dripped, there was no chance in hell that she was ever going to be able to cum with the ring secured around her clit.

One minute passed, and then another. The rhythm continued at the same pace it always had, driving her further and further up the cliff of desperation without ever once granting her a release. Then, just as she could feel her legs starting to give out from underneath her, Jeremy grunted one last time as he thrust himself into her rear. She felt his member swelling up, the tip pressing down against a spot deep inside her that she never even knew existed, and then…

“No, please, don’t stop,” she cried, but it was already too late.

One more stroke, just one more, and then she would have been able to finish. Never mind the fact that the signal would have been canceled out long before it even had a chance to reach her brain. Pressing her legs together, she desperately clung to the illusion inside her head, even as her pussy clenched down uselessly against nothing except empty air. Up above, she could feel a steady stream of warmth pouring out into her rectum as he emptied himself into her rear. Jeremy grunted and her body reacted in turn, squeezing down and milking the cock inside her as if doing so could somehow finally bring her over the edge.

“That’s it, tighten down for me,” he said, “Just like that.”

Cindy closed her eyes, panting in despair. Her ass felt so full she could hardly stand it. The only saving grace was that at least it was finally over at last. Or at least as over as it could get with pussy still clamping down hard around nothing as it desperately cried out for her attention. A mental image popped into her head of someone else stepping up behind her to take her there next. His cock would slide into her, slowly stroking all the bits inside of her that ached until she came hard around the shaft.

The lobby remained empty. There was nobody there.

“Well now,” said Jeremy, “That wasn’t so bad now, was it?”

He leaned in close to whisper into her ear, reaching down with his hands to give her one last pinch across the nipples of her breasts. Then, with one last squeeze, he slowly pulled himself out of her ass. The fluids of his deposit swelled up, threatening to spill out, and reaching into the drawer of his desk he quickly pushed a plug down into place. She winced, and as she stumbled over to where her clothes lay discarded on the floor, he smiled as he finally pressed the button to unlock the gate.

“See you after work,” he said.

Cindy shivered. The rest of what happened after that was a blur. Quickly, she got dressed, and as the elevators carried her upwards, she sighed as she finally stepped past the doors of her office. The clock ticked silently away on the wall above her head.

7:13 am.

Just a couple more minutes left until her meeting. Now, she just had to make it through the next eight hours of work before she could finally go back to her apartment and collapse in bed. Her nipples stood up stiff from underneath her bra and ignoring the way her clit rubbed up against her panties, she turned to face the webcam. A face popped up onto the screen. Someone important, someone that she should probably recognize.

Blink. Smile. Work mode on. Ask about the weather.

“Good morning, Mr. Johnson,” said Cindy, “How are you today? I know it’s a bit early, but I have the quarterly reports available for the meeting today if you would like to see them…”

The man nodded and yawned. More people joined the call. Shifting in her seat, Cindy smiled as the meeting went on, doing everything she could to ignore the plug in her rear and the semen trapped behind it.

A notification popped up on her computer. An email, from a certain security guard that she really did not want to open. Tomorrow, same time, it read. She quickly dismissed it. The next twelve months were going to be a pain in the ass.