Gray Areas

The gray areas had become very wide and ill-defined, their edges fuzzy. There was very little, it seemed, that could be seen as simply black or white. Not good or bad, right or wrong; not happy or sad, love or hate, best or worst; neither interest or indifference, nor concern or apathy. The list just went on—nothing was absolute. Just shades of gray.

Nora Dyson was thirty-two years old. Tall and long-legged, slim but shapely, she was well-proportioned, with a nice rack. At five-seven in bare feet, she touched six feet when she wore her outrageously high stiletto heels, as she often did. Nora was naturally graceful and statuesque, and she knew just how to move, to best display those qualities. While it might very well have been all muscle, Nora had enough flesh covering her bones that her shapeliness was undeniable, and she often wore long, clingy evening gowns, usually with halter-top neck, no bra, and high side-slits that emphasized the voluptuous aspects of her body.

She looked the part of an exclusive call-girl. She certainly didn't look like a seasoned detective working undercover to infiltrate a criminal organization in the city.

Nora was proud to be a police officer. She had chosen the field while still a freshman in high-school. In university she had proven herself, sailing through her undergrad program then almost effortlessly earning a Masters' degree in forensics. Following university, after breezing through basic training at the Police Academy, Nora was snapped up by the Metro Police Force. After a few years she met and fell in love with Marco, a fellow officer, so that, at twenty-seven, thoroughly enjoying her work, she loved her life, and thought it really couldn't get any better.

But, Nora's charmed life had gone for a shit all at once, in a sudden sort of triple-whammy. First, she had caught Marco in the act of fucking the neighbor. Subsequently, when confronted, it was revealed that he had been habitually and dispassionately unfaithful. He admitted to having several partners going at any given time. It was a statement not a confession, without even a hint of apology. So much for eventually getting married.

Second, before she could get over the shock of his betrayal, she found herself being questioned in connection with an investigation into his alleged pilfering of drugs from evidence troves. He had been suspected of liberating evidence for his own recreational use. Another unforgivable, in her view, transgression that he would have had difficulty explaining.

Sadly, before she'd even had a chance to confront him with that, she was delivered the news that Marco had been killed in a drug bust operation. He had apparently broken with protocol; being a bit of a cowboy, they had gone in with guns a-blazing, figuratively at least—flash-bang stun grenades and tear-gas. It would have been better if the 'guns a-blazing' had been more literal, as that's what the bad guys responded with. In the end, he, unnecessarily, got himself shot dead.

What a crazy fucking world. If the good guys can be such creeps, does it follow that the bad guys can be saints. Time would tell, perhaps.

She took Marco's multi-leveled betrayal badly. Nora grieved for Marco, and herself, and her wounded naivety; then, steeling her lost innocence, she threw herself back into work, with a gritty intensity, that was, by turns, impressive and frightening.

Without the slightest hesitation, she volunteered for a dangerous, deep cover infiltration operation. Given an intensive briefing, she was released into the nether-world of organized crime. Distancing herself from her previous reality, Nora smoothly became Ashley—her undercover name—and transformed, almost magically, into an elegant and sophisticated, soft-spoken sylph with an understated sensuality. She swiftly succeeded in getting hired onto a specific escort service, that was one of the suspected fronts of the target organization.

————— OXO —————

On the shadowy side of the law, the business was, in itself, still legitimate, but Nora's—Ashley's—handlers proposed that it was a convenient 'foot in the door' in terms of access into the mob, and, as the plan went, eventual contact with the gang's head honcho, Juan-Mateo.

The Good Company Escort Agency operated out of a small, elegant parlour next to a high-end restaurant, just off the casino floor of a five-star boutique hotel—which had an extremely complex pedigree. The agency was run by Michael—not Mike, please—Irvine (pronounced Er-vin.) Michael was Juan-Mateo's right-hand man—his first lieutenant, as it were.

During her orientation, Ashley was advised, just as she'd been told to expect, to take an escort persona. So, feigning taking a moment to think about it, she chose the pseudonym Candace, which she could shorten to Candy, as in 'Eye-Candy', or 'Arm-Candy'; although, as it turned out, she rarely did. Observing from the sidelines, Michael became, for some reason, suspicious of Ashley/Candace. He just didn't trust her, although he couldn't put his finger on why. Maybe her responses were just too pat, just too prepared. "Whatever," he thought. "I'm going to have to watch that one."

Candace sensed his unwanted attention. "I'm going to have to be especially careful around him," she told herself, deciding right away, she'd have to try to stay very deep, and keep her reporting out to an absolute minimum if she was going to survive.

The way the service worked was simple enough. The manager—madam—greeted the clients and set the rates. A cellular switchboard operator dispatched the girls, generally to a hotel room, and the agency took a one-third cut of the fees, leaving the ladies' tips alone. Candace was surprised and pleased to learn that the escorts were not obligated to provide sexual services. While some of the girls figured that was the point, clients were informed that any extra charges for intimate activities were to be negotiated with the escorts, separately. Candace had been wrestling with that possibility and was much relieved to find that she wasn't required to perform sex.

"That's optional, and personal," the manager told her, very matter-of-factly. "You have been hired as a companion, that's what the client has paid for. If you choose to offer sex, that is on you and you only. Some of the girls do so as a part of the package, a personal touch if you will. Some only for an extra charge. It's entirely up to you." As an after-thought, she added, "In fact, we don't even really want to hear about it."

Candace learned that she could hang about the lounge and sometimes pick up drop-in clients who came by to meet some of the escorts in person. Carefully, and surreptitiously, Candace pumped clients and employees for info—especially info concerning the big boss, all the while keeping a wary eye on Michael.

Besides the escort service, Juan-Mateo also ran a cocoa and licorice, spice and exotic herb import business. Candace's pre-undercover briefing intel had proposed that it was a front for a drug distribution operation, with prostitution on the side, but, so far, that appeared to be a completely unsubstantiated surmise. He didn't appear to be running a whore house either. The escort business seemed to be all above board and legit, at least, as legitimate as an escort business can be.

"Mind you," Candace mused, "could be he's importing illicit drugs along with the legitimate product." And, thinking back to the original undercover operation prospectus, Candace had seen absolutely no indication of any of the alleged human trafficking.

————— OXO —————

More than a month into her escorting career, Candace had become a popular 'date', while giving up nothing more than the odd hug and kiss at the end of an evening. She was beginning to actually enjoy the role. Looking absolutely ravishing, she was smiling as she tapped on the door of her next client. Sam, a short, chubby man, greeted her effusively, inviting her in with a sort of histrionic flare. Late fifties, or early sixties, Candace could see right away that he was someone well out of his depth. A rather fuddy-duddy businessman, he was, nonetheless, sweet, as he offered her a pre-dinner drink, attempting to be classier than he could ever possibly be. Candace appreciated his efforts, and they shared a pleasant drink before proceeding to dinner.

Dinner was lovely. Candace knew that reservations at Blue were very hard to get, nonetheless, they had a great table and a splendid meal. Interestingly, they never ran out of things to talk about, and chatted on like old friends. Over coffee and dessert, Sam began to confide in Candace. He told her all about his wife, and her passing away a year ago, and, wiping an errant tear from his cheek, admitted to his subsequent profound loneliness.

When they, reluctantly, moved to leave, pulling her chair as she rose, Sam asked shyly, "Would you, perhaps, join me in my room for a nightcap?"

Candace smiled at his shock when she replied, "I'd be delighted," taking his arm and gliding across the lobby to the elevators.

He poured them each a drink from the minibar—she a vodka and lime, he a bourbon, neat—and sat on the couch tentatively, leaving space between. Candace was amused, and yet flattered, by the earnest way he tried, with rather limited success, to be a sophisticated host. As they drained their glasses, Sam slowly just ran out of things to say— running down, like a wind-up toy.

As the thick, expectant silence folded over them, Candace watched and waited for him to break the hush, a flick of her eyes silently coaxing him to make the next move—whether that be simply a "Goodnight," or a chance for him to lavish her with a tip, perhaps.

He rose and took the empty glasses to the sideboard, then perching on the edge of the bed, he hesitated before sputtering, "Will you lie with me for a bit?" Surprised, but not really, Candace remained motionless, while she considered. Unable to endure the moment, Sam continued, "You're beautiful, and it's been a very long time!"

Slowly, Candace allowed herself a smile. She felt an affectionate sympathy for him. Furthermore, contrary to what he, and, indeed, everyone else in her circle of acquaintances, thought, Candace—Nicole—couldn't remember when she'd last had sex. It had to be months!

"Gad!" she realized, "it was before Marco went out on his ill-fated drug raid." She gave her head an imperceptible shake. "It was just before I caught him fucking that slut down the hall."

Poor sad-eyed, middle-aged Sam, took her hesitancy to be reluctance. He realized he couldn't expect her to just give it away. Tongue-tied, he tried to diplomatically ask about... "your fee schedule for extra services." Candace smiled warmly, soothing his discomfort, before actually rescuing him. "You mean how much extra for sex?" Suddenly she felt bad for teasing him. "That's negotiable."

Waiting a beat, he asked, "Is $50 enough?"

"From what I understand, the other girls that offer that service generally charge a hundred fifty, two hundred, or more." Sam's whole body seemed to sag.

"Oh..." He looked deflated, but Candace simply pushed on.

"Tell you what. For you, in memory of your late wife, two bucks. One shiny toonie."

"Really?" he gasped, but he was already fishing frenetically through his pockets, until he found a two-dollar coin. Holding it up, he raised his eye-brow in query. Candace nodded towards the night stand, and began to sway to the easy-listening music she had found on the TV set. She removed her dress gracefully and provocatively, smoothly hanging it over the wooden valet next to the bed, so as not to wrinkle it. She surprised herself at how easily it came—playing the part. How comfortable she was stripping in front of someone she had only met a few hours ago—someone to whom, under usual circumstances, she wouldn't ever be attracted. It struck her that it was all just a game, just role-playing.

As she stood, letting his eyes roam over her, painting her body with lusty desire, he tentatively reached his hands out to the hip-strings of her tiny thong. Wordlessly giving him permission, she allowed him to remove the last piece of clothing she had on—besides her thigh-highs—and, of course, her heels. As he drew them down her thighs, past her knees, his eyes fixed on her flat tummy, awed, entranced. And when he reached the carpet, she assisted him by stepping daintily out, leaving him fiercely clutching the warm scrap of material. He pressed it to his nose, reveling in its redolence.

Candace then proceeded to fuck him—surprisingly tenderly, and surprisingly expertly! He was small and, for the first go, anyway, hair-triggered. She grasped his circumsized stiffy in her hand and felt it twitch as she stroked him a bit. Then she leaned in to kiss the end; and felt it tremble. Rounding her lips, Candace slowly engulfed Sam's plum. She pushed her mouth smoothly over his glans, sucking him in, and holding the vibrating member for just a moment as she felt the radiating heat.

Sam's orgasm exploded virtually the instant Candace closed her lips around his shaft. Very suddenly he was jolting, and jerking, and jetting his nectar into her mouth and down her throat. As he came, as he threw his head back and growled, his hands went behind her head, gently pulling. His trembling fingers, entwining her hair, were, even in the throes of orgasm, more encouraging than insistent.

Somewhat surprised by the volume of his emission, Candace managed to swallow it all without gagging. Slowly withdrawing, a self-satisfied smile settled on her face.

"Sorry, sorry!" Sam croaked, hoarsely.

Looking up through her lashes, Candace grinned, then licked lewdly the final drips from his still quivering prick. "What are you sorry for?" she inquired sweetly.

"For cumming so quickly! For..."

"Oh, piffle," she said coyly, dismissing his concerns. Then, still holding his turgid member, she began to rise, sliding her fist along its length. She raised her brow in question—a silent, "Well?"

"Th-th-th-that was... That was... That was incredible!" Sam sputtered.

"Well, thank you," Candace purred.

"I've never had a... a... what do you say... blowjob before!"

"Really? A veritable felatio virgin!" Standing now, she gave his erection a playful squeeze.

"The wife wouldn't allow oral sex," he stated, rather sadly. "She thought the very idea was disgusting."

Candace pushed him back onto the bed and flopped down beside him, without releasing his thickening prick. Fumbling in his efforts to reciprocate, Sam leaned in and began kneading her left breast with one hand, while kissing and chewing the nipple of her other breast. At the same time, he snaked his right hand down over her tummy and petted her pussy. Candace, herself, was surprised as she felt her vagina begin to moisten in response to his caresses.

As he hardened in her hand, her other hand twiddled his nipples, until his cock began to twitch impatiently. She gently but authoritatively rearranged them both on the bed, until she was on her back and he was poised above her. Grabbing his ass cheeks, she pulled him into her, and they proceeded with a straight fuck, missionary style.

His breath rapidly became ragged, as he began to pound her frenetically. It was not long before he was, once again, roaring, and spewing his nectar deep within her. After just a brief respite, Candace set to wanking his softened tool, swiping her own pussy to gather natural lubricant. To a chorus of 'oooohs' and 'aaaahs' she manhandled his man-handle, until, just as she was considering giving it up as futile, his member swelled and bucked and spat one last time, covering her hand with his seed and leaving him virtually insensate.

Candace rose off the bed and retrieved a wet cloth from the bathroom. He lay enervated as she cleaned him off, staring up at her with a goofy grin, babbling, "Omigod! Omigod! Omigod!"

Even if the sex wasn't exactly inspired, and it wasn't, it was satisfying—satisfying in an almost ethereal way. In fact, Candace had a warm, fuzzy feeling, when they'd finished. It, somehow, made her feel that she'd actually done something good—something nice for someone.

"Thank you! Thank you!" Sam repeated effusively.

Lowering her eyes demurely, Candace replied, "No, no. Thank you!"

"Indeed," she thought to herself, "Thank you! Thank you for reminding me how much I like sex! Thank you for reminding me much I've missed sex!"

Smiling enchantingly, she pulled on her clothes and quietly took her leave. She considered her first 'paid' sex neither prostitution nor altruism, although she wasn't sure exactly what it was. Yet, quite apart from her mission as a police officer, and entirely separate from her objective in the undercover operation, she had serendipitously done something good. And that made her feel good.

At the realization, the reminder of how enjoyable fornication could be, Candace made a conscious decision to allow herself to enjoy casual sex if or whenever an acceptable opportunity presented itself—providing she felt so inclined. Still, she didn't overtly offer sexual services, but included them from time to time, at the end of a date as part of the package to select clients. "But I will not be a slut about it," she told herself, because, even then, it did not happen all that often.

So, especially alluring clients were treated, 'as part of the package.' She didn't charge, but, as some partners insisted—"You deserve it, Candy!"—she accepted a gratuity or, if they'd rather, an honorarium. This semantic sleight-of-hand allowed her to continue to believe that she was not engaging in prostitution. Consciously deluding herself that she was not a whore.

————— OXO —————

Staying deep undercover, Candace—actually, Nora the police officer—was getting frustrated by the lack of any evidence of a nefarious nature beyond, perhaps, pandering. Most of the business seemed legitimate. Still, Candace laid low, watched and listened. Finally, after what seemed like ages but was maybe five weeks in, Candace was introduced to Mr. Sanderington. Juan-Mateo Sanderingdon was, according to the police intel, the boss—the kingpin of the whole criminal organization. He was, apparently, just doing a walk-through of the various facets of the operation. Stopping in the parlour, when introduced to Candace, he nodded. "Just call me Matt," then he took her proffered hand and kissed it. Candace smiled coly, feeling just a little bit giddy, as he engaged her in light conversation. She welcomed his attention. The policeman inside of her considered it a big break in her undercover assignment.

But besides that, Candace thought he seemed like a really nice guy. His quiet confidence and unassuming manner were somehow entrancing. He appeared to be about forty years old, tall and fit and handsome.

While that first time, they really had a wholly unremarkable chat, interestingly, Matt began to frequent the parlour, dropping in unannounced, and asking after Candace. If she were available, he would ask her if she would share a coffee with him. What could she say? He was the boss, so they would often just sit and chat, about whatever.

Candace/Nora looked at every chat as an opportunity to gather intel. Indeed, after the first couple times, she was able to surreptitiously contact her handlers with news of her infiltration progress. But more than that, she found each shared coffee to be delightful and the anticipation of future visits to be tantalizing.

Sharing tidbits of themselves, Candace learned that Matt had been raised in a middle-class, blue-collar family, with three older brothers and one younger sister; that he'd been the only one in his family to ever attend college; and that he had a real honest-to-goodness MBA from a prestigious university. Candace had to be very careful not to blow her cover as she endeavored to stick to the truth. Divulging kernels of her own history, she told him that she was an only child; the daughter of a school teacher who died early in a traffic accident. Sometime later Matt alluded to the fact that one has to know how to run a business to be successful—whether the business was legitimate or not; hence, the MBA.