Gray Areas

One day, in a comfortable lull in the conversation, Candace asked, "Why is it that, even though I was introduced as Candy, you've never called me that?"

To which he replied, "Somehow I get the feeling that using the diminutive, Candy, would be demeaning to such a strong woman as yourself."

Eventually, over the course of a few weeks, after many cups of coffee and pastries, Matt requested Candace as an escort—ostensibly checking out the service—he said he needed a date to accompany him to a large charity gala. Dressed in her finery, and playing the part of his consort to a tee, they enjoyed a wonderfully pleasant evening together. It surprised Candace that, not only didn't he enquire about or request sex, he neither said nor did anything inappropriate or suggestive. Still, it seemed to Candace that, maybe, he was becoming just a tad infatuated—as, perhaps, was she; although she would never admit it.

In any case, it was quite clear to others that they were both equally fascinated with one another.

After a while, Matt began requesting Candace more and more frequently, for dates of various kinds. He quickly faced the fact that he was, indeed, very much attracted to her, and started to see that, although she initially resisted it, she was becoming attracted to him.

Candace was amazed, especially given her circumstances—and perhaps he was, too—that, all of their interaction had remained chaste. He was ever the gentleman—handsome and engaging, and they were, it seemed, forging a bond that was something far more than just a carnal attraction.

On subsequent dates Candace learned more about Matt, whom she often simply forgot was not a friend, but the target of her investigation. She found out he loved to cook; he loved small children, as long as he can give them back, like nieces and nephews; he played guitar; he was well-read, with tastes similar to her own.

Candace never really made a conscious decision to fuck the boss, her target, although, in retrospect, it would have become necessary, eventually, if she were going to avoid suspicion.

They slipped into intimacy without fuss or fanfare. It just seemed so natural—so inevitable. Candace rationalized, telling herself, "This is what a real escort would do, anyway. I'm just playing the part." But the sex was tender and gentle—and fabulous. She had trouble containing her feelings, keeping her mission in mind.

Really, from the very beginning, that very first time they'd actually 'dated', she'd had to keep reminding herself that he was a client and she was his paid escort; he was the boss, she his employee; he was her target, she was an undercover investigator; he was a criminal, she was the law. Now she'd had to tell herself, over and over again. "There is no love involved here—sex yes, love no. We are just fucking—not making love!" Deep down, she knew that she was just pretending to let herself believe that she was convincing herself.

Suddenly, Matt's social calendar got very busy, and he needed an escort several times a week. Long and frequent evenings spent together, led to a richly blossoming relationship, smoothly morphing into an intimate companionship. Neither of them dared consider it love, yet, but whatever it was, it continued to grow—and flourish. In order to further the pretense, Matt continued to pay the going rate for each and every 'date', adding, each time a tremendously generous tip.

————— OXO —————

Candace, of course, had other clients. A typical date began with meeting her 'date' in the parlour, and schmoozing for a few minutes over a drink. During that time she would assess the client, tentatively deciding whether he was a sexual partner candidate or not. Generally, they would, then, either go to dinner or attend some function or other. Following that they might go to a bar or a club, then she would allow him to take her 'home'—back to the parlour, unless he had become one of her select few, in which case, she would accompany him back to his hotel room for a sensuous romp. Candace didn't put out very often, but when she did, she put out one hundred fifty percent. Whether her evening include sex or not, the high quality of her performances was repeatedly confirmed by the size of her tips.

Candace tried to keep her emotional response to her success in perspective: "I am a police officer, on assignment. This is all just role playing, disguise." Notwithstanding, she knew that she was getting, perhaps, a bit too comfortable with the escort business. In fact, she realized, with some misgivings, that she had taken to it 'like a duck to water'. Furthermore, Candace was amazed at how quickly her personal bank account was growing; and even more amazed at the fortune she was amassing in the private, secret account into which she deposited all the tips—bonuses—Matted lavished on her.

But it was her dates with Matt that she really looked forward to. Candace had long since given up trying to resist her attraction to him. Repeatedly, she pointed out to her law-enforcement self that he didn't really seem like a bad guy, at all; just a businessman in a somewhat shady field. And for all her time with him, in his world, she had uncovered no solid evidence of anything nefarious. So, as she had nothing to report, she stayed rather incommunicado.

Candace was surprised by the numerous charities Matt generously supported. Consequently, they attended many gala events and benefits.

Considering how she had initially become acquainted with him, Candace was intrigued by Matt's expressed emotional aversion to pushing girls into prostitution. He argued that this was not an oxymoron, as one might, at first, assume. What he did, he maintained, was provide the girls that wanted to prostitute themselves—as they were going to, anyway—a safe place for them to conduct their trade—a choice of venue, as it were.

Matt's escort business was truly successful. A bonus, though, was that it offered an ideal opportunity for laundering dirty money. He also confided to Candace that he used his import and distribution acumen to develop a very lucrative cocaine and marijuana trade; however, with the legalization of pot, that whole end of the business had become too bureaucratic.

Candace continued to sail along within the escort business, seeing Matt frequently, but always as a paid date—keeping it all on the up and up, as it were. She found herself becoming much more picky when it came to adding sex to her other evening trysts; indeed, she was quickly shying away from participating in any casual sex during dates, in favour of waiting for Matt. "He is, after all, the target of this ongoing investigation," she repeatedly reminded herself.

Actually, Candace was terribly puzzled about her developing relationship with her investigative target—the crime king. She was beginning to think it was neither intimate nor platonic, but, rather, existed, indeed thrived, in the gray miasma between.

Of course, she continued to have other dates as well; some of which were with figures connected in various degrees to Juan-Mateo's organization. Surreptitiously she kept her ear to the ground, learning to elicit information about the various arms of the business, without appearing to be nosy. Surprisingly, most of her clients were gentlemen. Many dates were strictly platonic, simply female companionship in a strange city; while others were more intimate, ranging from suggestive banter and innuendo, to mild necking, to serious groping. Ending the encounter with full-on sex was becoming the increasingly rare exception.

Well into her tenure, Candace found herself 'escorting' a pair of wannabe policemen. Dwight and Chuck, were 'officers' in Michael's private security force who had been instrumental in thwarting a cheating scheme on the casino floor. Michael left word with the dispatch desk that they be comped adjoining rooms each with the girl of their choice for the night. He had allegedly said, "Make sure the girls know how to keep them happy."

Anyway, the thugs had been there before, so they knew—or thought they knew—what to expect. They felt that, because of their positions, they could demand favours of girls, with impunity. Swaggering loudly about the parlour, they made a big deal out of choosing their escorts—as if they were doing those girls a huge honour.

While Roxy put on a smile, and joined Dwight, Candace quietly informed Chuck that, she was an escort, not a call-girl, and, as such, sex was not one of the services she offered. "Just to be clear up front."

"That's okay," he replied with a predatory grin.

Candace was unsure of how deeply the two were involved in the criminal aspects of the business, but they most certainly were to some degree. At dinner, the pair proved to be loud and obnoxious, crude and insensitive. Still, much to Candace's satisfaction, they spoke openly and boastfully of illegal activities. Candace listened intently. Later, in the room 'for a nightcap,' Candace tolerated their groping caresses for a while before diplomatically declining further advances.

"Fuck that noise!" Chuck growled.

"Oh, come now," Candace purred. "I did explain my position at the outset of the evening."

Dwight jumped up, throwing Roxie, his date, aside, and grabbed Candace, pinning her arms behind her. "In fact, there ain't no way you're gonna get out of here before you've fucked us both!"

"Several times!" Chuck gloated, shooting a hand out to tear at her neckline, rending the fabric down to her tummy, exposing her luscious tits. Not one of the girls had ever declined their advances before, and they weren't about to let Candace be the first. "You and your holier than thou haughtiness..."

Candace kicked and squirmed but to no avail. Squeezing her bare boobs with both hands, Chuck leaned in and bit her nipple hard. She stopped struggling, stifling a scream. "Now," hissed Dwight, in her ear, "we can do this easy or hard. It's up to you, but it's going to happen!" He pulled her elbows tight behind her back as Chuck ripped off the rest of her dress, leaving her naked except for shoes and stockings.

It was with great difficulty that Candace finally accepted that resistance was futile. Finally, in an act so contrary to her natural response, she let herself to go limp, becoming completely passive. Her lack of active response, enraged her rapists. They were confounded that suddenly they couldn't arouse even the least bit of protest from her. Employing Roxie to get them hard between assaults, they each fucked her missionary, doggie, anally. Pushing a semi-turgid tool between her lips, into her mouth may have been taking a chance, but Candace realized that to bite down on the intruder would probably be signing her own death warrant.

They had cum three times each by the time Chuck sawed back and forth to erection in Candace's mouth. Dwight had also finally got stiff and hard under Roxie's oral ministrations. Chuck wormed his way under Candace and pulled her virtually limp body atop, spearing her with his upright woodie. Sensing what was up, Roxy tried to intervene, but, with a firm backhand, was told to mind her own business. Abandoning Roxie, Dwight fitted himself between Candace's legs and pushed himself insistently against her rosebud. Chuck pulled her hips down hard, until her genitals were resting tight against his pelvis. Then, with a relentlessly steady stab, Dwight pushed past her sphincter until he was balls deep in her ass. They picked up a rhythm that she couldn't help but echo, accelerating until, finally, pounding mercilessly, they pulled each other over, flooding both of her orifices with their last few spurts of pecker-snot!

They each stepped back, leaving Candace lying inert on the bed, and Roxie sitting knees up, stunned in the easy-chair, and did up their clothes, glaring at the women with looks of undiluted disgust. Chuck snarled, as he drained his unfinished drink, "Not so special now, eh bitch? Just another whore like the rest of them. And don't bother reporting this. We're security, ergo, we are 'the police'. Who are they gonna believe anyway? It'll be our word against that of an annoyed whore's."

Laughing, Dwayne said, "Look on the bright side: 'likes rough sex!' That's something you can add to your CV!" The two bastards then walked out, slamming the door.

Candace told the dispatcher, although she didn't make a big deal of it. She wondered what her character would do. Brooding on it, she consciously didn't report the incident to her investigative handlers, choosing instead to stay silent, well entrenched. Surprisingly, during the very next date with Matt, he casually mentioned, a if it were just a tidbit of gossip, "A couple of our security team—wannabe-cops— died the other day. I believe you've met them, Chuck and Dwight." Raising an eyebrow, Candace remained silent, as he continued. "They snorted an unauthorized sample of product—coke cut with fentanyl. Sadly, they both OD'ed."

Receiving some secret communication from her handlers, wondering when she was going to contact them, or come in, Candace remained silent. "They'll just have to wait," she muttered to herself. "Nothing's been resolved, nothing really has even been discovered. I haven't decided what to do, yet."

Candace was sensing a dawning awareness that Matt was quietly looking out for her—for her well-being. More than just that, she had begun to realize that Matt was protecting her; without appearing to be interfering, he managed to keep her from being exposed to or sullied by the nature of his business. More so than her investigative handlers. And that impressed her; it warmed her. She felt herself struggling with the ideas of loyalty and betrayal. To whom did she owe what; the establishment and their bureaucracy, that had sent her into this deep underground, or Matt, and their growing mutual attraction? The breadth of gray area between the two was totally dependent on one's point of view.

————— OXO —————

Watching Matt, as they spend time on a 'date', schmoozing at yet another gala, Candace feels herself becoming enchanted, once again—overcome by her blossoming relationship with Matt. A smile creeps onto her face as she reminisces on how they'd made love that first time. They had hardly spoken a word. I just happened, gently, smoothly. Like it was meant to be. The delicious feeling of him in her—thick and stiff, sawing long, slow strokes; their arousal merging into one; the liquid warmth of their shared climax. Even now, those incredibly sensuous details of their first sexual encounter elicit a tingling in her genitals, glowing amidst her recollections. Try as she might to deny it, deep down Candace knows she is falling in love.

More and more, lately, after making love, Candace and Matt's pillow-talk conversations have turned deep and candid. Candace is surprised by Matt's frankness, and the ease with which he often seems to reveal little bits of information that could, maybe, be used to bring down his whole operation. Candace constantly argues with herself about her responsibilities. "I am, after all," she repeatedly reminds herself, "still a deep-planted undercover agent, charged with collecting intel for the ultimate exposure of Matt's criminal empire." Yet she can't help thinking of him not as a really bad guy, but rather as a very successful businessman in his chosen field. "In a lot of ways," she tells herself, "he is a good guy—a really good guy!"

One evening, the discussion has turned to the morals of selling coke. "I don't create the addicts," Matt explains. "I just exploit the market they create!"

"But what about the young ones trying it for the first time?"

"Come on... Everyone knows the risks, nowadays," he says, rolling his eyes. "They're risk-takers. If not coke, then something else." His smile betrays the fact that he knows that he's rationalizing to some extent.

Candace finds, as she often does, she has a hard time arguing with him. He is a very logical, persuasive debater, and she has become increasingly convinced that right and wrong are no longer absolutes. Perhaps they never have been. "Life, it seems," Candace muses, resignedly, "is made up of mostly gray areas."

As their relationship continues to grow, Matt often talks about changing their lives. Until, one day, he, enigmatically, declares, "I think it's time to lift you out of the escort business, altogether, and free you from your various other entanglements."

Candace is puzzled by his choice of words, but he disregards her questioning look, and doesn't elaborate. In a sort of conspiratorial whisper, he goes on to say, "I am seriously considering retiring, as it were." Then, gazing lovingly into her eyes, he adds, "We could make our escape together." He punctuated the remark with an exaggerated wink, as he rose from their bed to dress, leaving Candace's mind in a molten turmoil.

Candace is completely out of sorts over the next few days—feeling what?—adrift and foundering—discombobulated. The idea of leaving it all behind, of getting away, her and Matt alone together—suddenly seems too wonderfully inviting—more than she could hope for. On the other hand, turning him in for his crimes against society seems to be unspeakably cruel, and heart-wrenching. She is totally torn between what is right and what is best and what is unspeakably unacceptable! Everything, it seems is gray—neither fish nor fowl. Nothing is simple; nothing is clear.

In fact, she realizes that she is not all that clear on her own identity—no longer even sure who she actually is: Nora or Candace, Ashley or Candy. Furthermore, she comes to the sad understanding that before she can establish who she is, she has to decide what she wants to be. Candace—just to keep it straight forward—recognizes that she truly loves Matt, and she believes he loves her.

"So?" she asks herself, "Now what? Where do we go from here?"

Only a few days later, while bathing in the afterglow of an immensely satisfying session of afternoon delight, Matt rises onto his elbow to look at Candace directly. "Well, I've been thinking about this for a while," Matt says, watching her face intently. "Actually, I have it mostly set up, already. How about we take our retirement on a Caribbean beach, and leave Michael back here, in charge of the business?"

"Michael in charge; that kinda scares me."

"I know. He doesn't like you—he doesn't trust you."

"I really think he'd as soon kill me as speak to me."

With a tiny grin Matt flippantly agrees, "Oh, probably."

Yet, suddenly, Candace just can't stand that she has been continually lying to the man she has come to realize is the love of her life. She can no longer abide this living a lie. Sick of always being on guard—sick of the constant deception, Candace finds herself confessing—even though it might just cost her her life. "Michael doesn't trust me with good reason. His suspicions are true." Candace reveals that Michael has been correct all along. And that he, Matt, has been the object of a deep undercover investigation of which she is an integral part. She is responsible for gathering evidence to facilitate his ultimate arrest and conviction. "But I just can't continue. I just cannot do it."

"I know, dear." Matt smiled at the shocked look on Candace's face. "You've had Michael quite worried." Her jaw hanging limp, fear radiates from her eyes. "I'd asked him, you see, when you first showed up, to find out all about you, or, at least, as much as he could. He thought you were a danger from the start—desperately wanted to eliminate you, in fact. I asked him to wait, because I thought I'd seen something that interested me."

Reaching in, Matt gently strokes Candace's cheek. "And I guess what I saw was an alternate ending."

"Omigod!" Candace whispers.

"Oh yes," Matt chuckles, wryly. "You were right in fearing Michael—in feeling that he would kill you, given the chance. We know all about your history—and your job. Indeed, Michael has a complete dossier on you." Matt studies Candace's wide eyes, contemplating for a moment. Before continuing, he cups her chin, holding her gaze. "But I also know that you have not yet passed on any of the tidbits of info I've recently fed you. So..."