Whitemailed Ch. 04

Haziran 5, 2021 0 Yazar: admin

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In the hours following Caroline Jarrett’s surreal encounter with her Boss behind the closed doors of his office, the middle aged divorcee fought to make any sense of what had happened.

“You just went against everything you’ve ever stood for Caroline,” her saintly inner conscience berated. “Not only was it unprofessional to let that happen in the first place, you let it go on for nearly a minute, then you made a Goddamn fool of yourself when you tried to leave spilling your purse all over the floor. Is that the way you want to get your promotions…by being the Boss’ personal slut?”

“But you didn’t do anything wrong Caroline…You were the one that put a stop to it before things really got out of hand…you looked into his eyes after it was over…you saw that look…he knew he was a guilty as you were…two consenting adults who obviously made a mistake but put the brakes on before things boiled over…his apology sounded genuine Caroline…nothing will come of this,” the glass is half full part of her psyche tried to reassure.

“But how are you going to walk into work tomorrow and act like nothing ever happened?” she openly wondered.


Dave sat alone in the privacy of his office for nearly an hour after Caroline left.

“What just happened?” he kept asking himself over and over, the whole time allowing the faint taste of Caroline on his lips to tease his palate.

Swirling side to side in his deluxe sized office chair, Dave rubbed his fingers against his right temple as he fixated on the spot on the floor where the two had shared their brief but passionate kiss an hour earlier.

“I want her…even more than I did before,” he said dryly, knowing his best chance at having her had dissipated the instant Caroline tore her lips away from his and started to fumble for her things.

“Unless…,” another more ghostly entity deep inside his psyche dared to whisper as he turned his gaze towards the spot on the floor where Caroline had accidentally spilled her purse.


A Month Later

For the first time since their Pre-Christmas hotel get-together, Dave had acquired the services of Sheila and Destiny, this time for a lazy Sunday afternoon tryst.

Seated in one of the upscale hotel’s luxurious chairs, Dave sat smirking at the beautiful black girl kneeling between his legs and felt his veins pulse at the way her thick cherry lips distended and churned around the girth of his grotesquely aroused manhood. Nearly hypnotized by the way repetitive way Destiny’s mouth bobbed up and down on his crotch, Dave would steal the occasional glance over to Shelia on the bed and smiled at the way she casually rubbed her right hand over the panty clad triangle of her strawberry blonde public fleece.

“So…you’ve invited another girl along to join us?” Sheila asked, her curiosity tweaked as to her john’s motives for the meeting.

“Yeah…I figured the more the merrier,” Dave joked. “Actually…I met a girl at work a while ago and we were fooling around for a couple of weeks…one night the subject somehow got to what us three did a few months back and she seemed like she’d be interested in something like this …so I decided I try to set something up…You don’t mind the added company do you?”

“No…not at all…it sounds exciting,” Sheila smiled. “Plenty of everything to go around!”

“Good…She should be here pretty soon…I just figured we’d get a head start…so to speak,” Dave quipped before rubbing his hands over Destiny’s head as she continued to briskly lather his cock.


“I really should have called his cell first to make sure I was at the right place,” Caroline Jarrett groaned as she struggled to make her way through the labyrinth of hotel corridors until she finally reached to her destination.

“Here it is…Room 447,” she mumbled, checking the hand-scribbled note in her pocket one last time just to make sure. “I can’t believe I’m here working on a Sunday…Dave said this would be rare and how could I tell him ‘no’ when he asked me to come along to help tie up the loose ends of this big contract so we could have everything in writing for first thing Monday morning.”

“At least they picked a nice hotel,” Caroline chirped, admiring her ritzy surroundings, the whole time filling with a sense of vindication and pride that her and her Boss had been able to get past their passionate interlude a month earlier in Dave’s office and have him still trust her enough to invite her along to help with such a big assignment.

Patting her sweater and hips, and making one last attempt to caress her hair was straight, Caroline plastered on her friendliest smile and knocked on the door.

Several moments later, Caroline braced herself as a set of footsteps crept closer to the inside of the door. Taking a deep breath as she waited for the door to open, Caroline’s face went ash white and she felt as if the floor had collapsed esat escort beneath her the instant she first peered inside.


For a litany of reasons, Dave Sisler had been left somewhat numb and confused in the days following his stolen kiss with Caroline. Even though the tenderness and warmth of Caroline’s lips still resonated on his a full month after the brief interlude, what Dave kept coming back to was the photo in the wallet Caroline had spilled on the floor when she scurried to leave.

“That girl in the picture…that girl in the picture…that girl in the picture…it just has to be a coincidence,” he would tell himself before a sadistic need to know pressed him to investigate further.

Tantalized by the damning ramifications of his potential discovery, Dave had spent the following evening planted on a barstool near the stage of the club where Destiny danced.

Steadily becoming drunk as he tried to compare the sweaty face of the stripper on stage to the yearbook photo that tumbled from Caroline’s purse, once the pretty black girl’s last dance was done at a little after 1am, Dave excused himself out to the parking lot, and the stealth of his car, and patiently waited for the young college girl to make her way out of the club to leave for the evening.

Jotting down the license number as Destiny got in and started the engine, later the next day Dave called in a favor to a friend of his at the Illinois Division of Motor Vehicles and in a short order, his suspicions were confirmed.

That nugget of information safely embroidered into every fiber of his brain, Dave then had to decide what, if anything, he was going to do with the knowledge of who Destiny really was.

“Nothing…you’re not going to do a damn thing with it,” he would frequently tell himself in the days following the discovery Even though he found himself digging deeper into Caroline’s past and present, and inevitably, other slices of interesting data continued to rise to his attention.

One of the more useful bits of information in Dave’s search turned out to be the discovery that the college scholarship Caroline’s oldest Son was getting happened to be sponsored by a company that Dave had a friend on the board of. A friend that conveniently Dave had first hand knowledge of several potentially embarrassing extra-marital affairs. A friend that would certainly be willing to trade the anonymous revocation of one of his company’s scholarships to keep word of his private indiscretions away from his unsuspecting wife.

So as Sheila cautiously opened the hotel room door and stepped aside so the middle aged black woman standing there could see all the way in, Dave’s adrenaline crested in fear of how the next few moments would play out.

“Caroline…Glad you could make it,” Dave said dryly, the words having no effect juxtaposed with the image of a young black girl kneeling between his legs with his dick snugly embedded inside her gaping mouth.


Motionless, Caroline’s heart skipped as she stood in the doorway. Expecting to see two grown men, perhaps dressed in suits going over a pile of paperwork on a table when the door swung open, she had no way to prepare herself for what she did see several feet in front of her.

“That…that almost looks like…like…Tijuanna on the floor,” Caroline dreadfully mumbled, her eyes turning to cubes of ice in their sockets.

“It can’t be…it’s just a girl that looks…like…her,” Caroline’s inner and almost aimless rambling continued until an audible gasp escaped her throat.

“What’s…what’s…going…on in here?” she choked out loud, teetering side to side now on her pumps, knowing she was going to probably hate the eventual answer to her own question.

Still standing only half inside the doorway, Caroline felt as if a wrecking ball had rammed her gut when the young black girl kneeling at her Boss’ feet turned to face her, with Dave’s cock still lewdly wedged between her puffy lips.

“OH…MY…GOD…,” Caroline muttered in slow motion the instant her maternal recognition kicked in.

“Ti…Ti…Tijuann…a,” the older woman babbled, her honey brown cheeks now the color of paste as she watched Dave’s sloppy, wet dick dangle free from her Daughter’s trembling mouth.

“M…Ma…Mama,” the young black sexpot’s voice cracked with horror, her half naked body noticeably cowering on the floor as the gravity of the moment overtook her.

Smirking ever so slightly, Dave watched the scene play out between Caroline and Tijuanna, knowing it could explode at any moment. Taking his penis into the safety of his right palm, Dave blindly traced the fingertip of his index finger along the ridge of its still throbbing cockhead, unable to tear his morbid gaze away from two generations of the Jarrett family locked in an apocalyptic stare.

“Get your clothes on and get out of here,” Caroline growled through gritted teeth at her etimesgut escort Daughter, her normally serene and caring face now ulcered with anger as she paced to the center of the room.

“I don’t know whether to kill him or you first?” Caroline added, with no hint the statement was a hallow threat.

“GET OUT OF HERE,” her voice boomed once more, this time causing Tijuanna to spring to her feet and grab a sheet from the bed before making a tearful beeline to the door and out into the hall before she could fully wrap the sheet around her bra clad torso.

Dave just shook his head, still somewhat detached from the surreal gravity of the Pandora’s Box he had opened.

“Your Daughter’s been keeping secrets, Caroline,” Dave said with a dry matter of factness, the cold tone of his voice seeming to smack his paralegal across the face as she stared down at him in the chair.

“Don’t even think about talking to me,” Caroline spat down to her Boss, the blood tingling in her fingertips as she fought the urge to reach down and choke him.

“Nothing has to come of this, Caroline,” Dave spoke softly, nodding over to Sheila for her to close the door to give the three privacy. “You’re one of the best employees I’ve ever had, Caroline…I’d really hate to lose you but again…that’s totally up to you. As far as I’m concerned none of this ever has to leave this room.”

“You Bastard,” Caroline muttered, unable to quite fathom the depths of Dave’s emerging depravity.

“I know this job’s pretty important to you Caroline…for a lot of reasons…I know your Ex has a pretty good job as well…as an architect I believe with a struggling firm here in town. Really be a shame if some of the businessmen I deal with suddenly stop using his firm for their projects wouldn’t it? You and him also have three kids in college right now…that’s got to be a burden!! I think one of your boys has a scholarship though…worked pretty hard for it from what I understand. Coincidentally…that company that sponsors his grant in aid…one of the guys on the board happens to be a friend…be a real shame if the funds to roll over your Son’s program were to suddenly dry up,” Dave spoke methodically until it was clear Caroline was grasping what he was not so subtly hinting at.

“You bast…,” Caroline started to say again, this time much more weakly than before until her mouth went mute.

“I’d love nothing more than to just see all this go away,” Dave announced several moments later, after allowing the weight of measured silence to press down on Caroline’s soul.

“…How?” Caroline relented, her body looking like a balloon with the air leaking out, hating the fact that she was being forced to negotiate in such a disgusting spot.

Stunned and somewhat disbelieving when he heard Caroline’s conciliatory tone, Dave rolled his tongue around his mouth before answering.

“Well…not to put it too bluntly but…I had arranged for some favors from your Daughter and her friend over there…there’s the money I left right there on the table for her but she obviously left a few minutes ago in a hurry for some reason I’ve yet to figure out without finishing what I had hired her for,” Dave droned, almost hypnotically.

“All I could really ask for, Caroline,” he continued, “Is for you to be responsible for your child’s dereliction of duty.”

“WHA…,” Caroline croaked, her head throbbing as Dave’s suggestion sunk in.

Stealing a quick glance over her shoulder at Sheila standing like a half-clad fly on the wall behind her, Caroline’s stomach rolled as she digested her Boss’ crude but clear offer. Vacillating, Caroline turned to face Dave once more and searched for any hint of decency in his eyes.

“His Goddamn dick is still hard,” she noticed, mortified that anyone could maintain an erection while backing another person into such a vile corner.

“I’d rather slit my own…,” Caroline started to say before her own tongue twisted and she went silent in mid sentence again.

“A couple of weeks ago you were standing in this guy’s office, kissing him as if it was the most important thing in your life,” Caroline internally berated herself. “Now THIS…why is he doing THIS to me?”

“Because he can,” the clear and decisive part of her psyche answered without missing a beat. “And you don’t really have that many options right now to deal with it!”

“All I’m really asking Caroline is for you to step over here and show a little goodwill in finishing the job your Daughter was hired to do,” Dave calmly beckoned.

A bitter tint of resignation colored Caroline’s cheeks as she stared down at her Boss openly massaging his crotch in front of her.

“You could just walk out of here and be done with it…just let the chips fall where they may,” Caroline’s inner voice chirped, but her feet didn’t move.

Even though the hotel’s air conditioning had the room freezing, Caroline could feel beads of perspiration dotting her brow as the walls of the ankara escort room seemed to close in.

“There will be Hell to pay for this,” her eyes clearly promised as she took the short walk forward, to the same spot on the floor Tiuanna had been only minutes earlier.

A nauseating riptide of Vertigo bristled through Caroline the instant her right knee pressed into the carpet and she caught her first whiff of the masculine scent of Dave’s arousal.

“Open your mouth, Caroline,” Dave quickly demanded, enjoying the way his erect penis caused an imposing shadow to sway across his paralegal’s damp forehead.

His eyes trained like a laser on Caroline’s Revlon coated lips, Dave grinded his behind against the seat until her lower lip quivered, then ever so subtly dropped. Seizing the moment, Dave thrust upwards until the spongy head of his penis disappeared inside his employee’s mouth.

“I could bite his dick in half right now,” Caroline told herself, knowing she could end Dave’s sex life right there on the spot.

Still, whatever force was guiding her caused Caroline to sit there and perform her morbid chore.

Tilting his gaze over to Sheila once his cock was firmly buried inside Caroline’s mouth, Dave took a measure of satisfaction in the shocked expression etched across the redheaded escort’s face. Locking eyes with her long enough to convey a silent but clear message, Dave turned his attention back to the black woman at his feet.

“Bet you would have gone all out giving me head a few weeks ago back in my office,” Dave taunted, the level of passion in the kneeling woman’s act clear in the halfhearted way her mouth worked up and down on his pulsing shaft.

Knowing he could flood Caroline’s gullet with his cum any time he wanted, Dave kept cinching his fingers around the base of his penis each time he felt the tipping point nearing, in a clear and arrogant act to prolong the exquisite rush of having his dick wedged between Caroline’s taunt lips.

Nodding up to Sheila when he saw the stripper easing up behind Caroline’s left shoulder, Dave let out a chuckle of approval seeing she had followed his insinuated orders to a tee. Knowing Sheila was now in position, Dave turned his full attention back to Caroline and the way her face bounced up and down on his groin. Focusing his sightlines even lower, Dave’s gaze settled on the buttoned up front of Caroline’s blouse.

His mind quickly drifting back to how good Caroline’s breasts felt pressed against his chest during their shortlived kiss in his office, Dave’s hormones raged feeling her bosom rubbing the inside of each of his legs.

“Unbutton your shirt,” Dave sniped down to Caroline.

Several moments passed and Dave assumed his employee was ignoring his request.

“Unbutton your shirt,” he once again demanded. “I want to see your tits!”

His cock jerking violently in Caroline’s mouth when he saw her hands finally rise to the top button of her blouse, Dave took a great deal of depraved satisfaction when the middle aged black woman began fumbling with the clasps.

“MMMMMMMHHMMMM,” Dave groaned out loud, feeling the seed in his balls begin to simmer when Caroline’s lace encased titties came into view.

Caroline’s nasal exhales tickling his pubes, Dave lowered his right hand down on top of her head to hold it steady when he felt the slimy magma of his impending release jetting up the shaft of his cock.

“UURRGGHH…GGGOODDDDDD,” Dave grimaced a few seconds later, his hips rocking off the cushions below as he ruthlessly facefucked his kneeling paralegal.

“GGHHAAHHH…GGRRHHAAHHHHFFFUUCCKKKKK,” Dave shuddered over and over, keeping his grip tight on top of her scalp until every last drop of his pungent lust had settled in the back of Caroline’s throat.

Nodding for Sheila to take a few more steps closer behind Caroline’s turned back, Dave then slipped his fingers around the base of his cock and pulled the congealed slab free from his employee’s mouth.

“UURR…RRR…AAHHH,” he visibly shivered when the sensitive underside of his dick rubbed against the bottom row of Caroline’s teeth upon withdrawal.

Once his cock was removed, Dave leaned back in his chair and watched as several rivulets of cum leaked from the corners Caroline’s lips. He even marveled at the lewdness of how a milk colored bubble formed in the opening of her mouth upon her first exhale, at the same time several strands of his ejaculate trickled down Caroline’s chin just before splashing down to her smooth brown chest and cleavage.

Turning his gaze up from Caroline just as she began to shift her hand up to instinctively wipe the slimy residue from her face, Dave was startled by the suddenness of Sheila reaching down and grabbing Caroline’s hand before she could get it all the way up to her face.

Her hand trapped in Sheila’s grip, Caroline looked up to see the six foot tall feminine frame towering above. Before she could even begin to discern just why the redhead had taken a hold of her hand, Caroline’s already scattered brain was thrown for another loop when she saw a grotesquely huge faux phallus rising perpendicular to Sheila’s crotch.

“…Dear…God…what now?” Caroline moaned when the intense heat of Sheila’s stare cascaded down on top of her.

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