Whitemailed Ch. 02

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Dave Sisler lives a fantasy.
6.8k words
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Part 2 of the 4 part series

Updated 09/22/2022
Created 05/31/2004
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"Five minutes to Four in the Goddamn morning," Caroline spat when she turned the ignition of her car to start it, her voice hoarse from the previous seven hours she had just spent alone with her Ex-Husband.

"I gotta get home and at least try to get a few hours of sleep before work... " Caroline half dazedly muttered before stopping in mid breath when she saw the message light blinking on her charging cell phone.

"That can't be good," she groaned, not immediately recognizing the number on the display.

"Hi Caroline... this is Dave Sisler... from the office. Its about 8:30 or so... a couple of other things came to mind that I wanted to run by you. Don't worry about calling me back... if you can though... maybe try to get to the office an hour or so earlier in the morning... I think you can be a really big help to me on this project Caroline... thanks again and I'll see you in the at 7 maybe," her Boss' voice trailed off before the click that ended the call slapped her across her sleepy face.

"Shhh... iitttt," Caroline groggily hissed, her hope of getting at least a few hours of sleep and still being able to get to work on time, now dashed.

"You could always go in late and say you didn't get the message," the fibbing part of Caroline's psyche offered even though she knew deep down she had a good thing going at the office and didn't want to mess up the goodwill she had already forged.

"And Besides... a long day at work will be a good thing... you'll need something to take your mind of what happened with Steven earlier tonight... because you know your gonna feel like crap as soon as these endorphins start wearing off... not to mention the guilt that's gonna come with it... "

______________________________________

Somehow, Caroline had been able to drive herself home, sneaked in an hour's worth of shuteye, showered and got herself to work 15 minutes before Dave Sisler arrived at the office. Propped up by more coffee than any human should have rightly consumed in one day, Caroline had made it to 5 o'clock but as she headed to her car for the ride home that evening, she was mentally and physically spent.

Checking her cell phone for any new messages, Caroline for some explicable reason felt crestfallen when there wasn't anything from Steven on her answering service.

"What... like you thought he was gonna actually call you after last night?" her inner voice mocked. "He's your Ex-Husband and he just wanted a lay... wasn't that the same thing you wanted too... and now you feel guilty and mad that he didn't call?"

Deep down, Caroline knew how silly and useless that pining for Steven was and thankfully, with each passing day, Caroline was able to put the events of that illicit and ill-fated rendezvous with her Ex out of her mind. As the holidays approached however, Caroline was frequently reminded of her current situation. She was still single, still bitter, still poor and with the office Christmas party coming up the following weekend, she didn't have a clue who to find for a date.

Considering she was more than a little older than most of the single men at the Firm, not to mention, black and still new around the office, Caroline had no idea which way to turn until she arrived at the last dreaded option, a blind date.

Giving in and allowing a friend of hers from business school to fix her up with one of her cousins, Caroline didn't meet Larry until a day before the party.

He turned out to be handsome enough, 41 and the divorced Father of two and upon seeing him in his tux and how good they looked on each other's arm, Caroline figured she could have done worse. Still, as the evening progressed, it became clear there just wasn't any chemistry between the two. The party itself was an ordeal, and Caroline was glad the open bar was free and Larry was driving.

The fact that so many of her co-workers were happily cavorting with their spouses or significant others, while she was forced to fake it with a man she barely even knew, made it that much more difficult.

The fact that Larry didn't want to dance made the time move even slower. Sharing a few polite trips out onto the dance floor with various men from the office, Caroline tried to be the best social butterfly she could as the bourbon slowly dulled her cares away.

Doing the best she could to soak in the sights and scenery around her, Caroline gradually became drawn to the only other seemingly single person in the room, her boss, Dave Sisler. Having heard through the grapevine he had divorced before she began working at the Firm, Caroline couldn't help but notice how Dave seemed to share quite a number of dances with various girl's from the secretary pool.

"They're all just networking," she laughed to herself in between failed attempts to get Larry to take her out on the dance floor. "Besides... he's the only single Partner at the Firm... just look at the way all the other wives of the Bigwigs have their Husbands by the ear keeping them from dancing with any of the younger girls."

Just as she was watching Dave finish another quick dance with one of the other girls, their eyes suddenly locked. A few moments later, he had walked over and politely asked Caroline out onto the floor. Hesitant at first, not wanting to upset Larry, Caroline hemmed and hawed for a couple of seconds before nodding to her date and accepting her Boss' invitation out to the center of the floor.

"You do look beautiful tonight Caroline... your Boyfriend is certainly a lucky man," Dave complimented with real conviction as the two started to dance.

"Thank you," Caroline replied after spending a moment to organize her bourbon washed sense of balance.

"He's not my Boyfriend," she started to tell Dave before deciding it was too awkward and useless to explain her and Larry's arrangement.

Caroline self consciously seemed to feel everyone at the party's eyes train on her as she spun around the dance floor with her Boss, especially the sights of some of the secretaries Dave had danced with earlier in the evening.

"They almost look like their jealous," she laughed into her dance partner's ear.

"Let them," Dave cracked before whisking Caroline across the floor once again.

"You really are a good dancer Caroline," Dave whispered softly into her ear. "Most of these younger girls can shake a grind just fine but they have no clue how to actually dance."

"Thank you... you're not too bad yourself," Caroline once again babbled, feeling dizzier by the moment as her bosom pressed against Dave Sisler's chest.

"He doesn't look too happy," Dave commented a few moments later, catching a quick glimpse over Caroline's shoulder, at her date through the crowd.

"Who?" Caroline asked.

"The guy your with... he looks kind of bored over there against the wall," Dave added.

"Oh... don't worry about him," Caroline's chirped, her inebriated conscience thrilled someone cared enough about her to get a little jealous for a change.

"Not a bad position to be in," she thought to herself. "Sharing a dance in one man's strong arms while another's getting jealous over you on the other side of the room."

Within a few moments, the last song was over and Dave and Caroline shared a brief hug before she walked back over to join Larry.

Walking through the throng of revelers, Caroline couldn't help but soak in the sexual vibe that was percolating through the room. Approaching her date, Caroline gave Larry a giddy and knowing smile as if to say the fun for the evening might not be completely over.

"You ready to go?" Caroline offered with more than a hint of tipsy suggestiveness.

"Yeah... I guess," Larry dryly replied, helping Caroline to the coat room before the two headed back out into the awful, Mid December cold.

Once back in the comfort and warmth of Larry's passenger seat, Caroline let out a long sigh of relief when the car finally turned on the main road home. Rolling down the window a few inches when she lit a cigarette, Caroline's spine shivered from the duel sensation of the nicotine kicking in as well as the cool rush of air against her clammy skin.

"I had a great time Larry," Caroline beamed between puffs of her Kool, extending her right leg all the way forward in the floor board until her evening dress hiked up enough so that her thick, well toned thigh was clearly visible to her date.

"Good," Larry replied distantly.

"You OK?" Caroline finally asked, sensing a tone in Larry's voice.

His dick hardening in his pants at the way Caroline had her leg propped up and exposed, even though Larry could sense from the way Caroline was acting he could probably have his way with her when they got back to her place, like so many other times in his life, Larry allowed his mouth and his insecurities to screw things up.

"Do you always dance that close with your Boss?" Larry accusingly asked out of nowhere, taking Caroline by complete surprise.

"Wha... " was all the drunk woman in the passenger seat could muster.

"N... Nothing... its none of my business," Larry quickly added, immediately knowing he had turned over a rock he shouldn't have.

"Then why in the Hell did you bring it up?" Caroline incredulously spat. "I gave you every opportunity to get out there and dance with me and you said 'no' each time!"

"So... are you like trying to sleep your way to the top or something?" the man Caroline had known for all of two days sniped.

"WELL FUCK YOU," Caroline screamed, having to fight the urge to reach over and gauge the man's eyeballs out with her fingernails as he drove her home.

"I'm the one coming home with you ain't I?" Caroline tried to reason a few moments later which elicited nothing but more brooding silence from Larry.

"Act just like my fucking drunk Ex-Wife," Larry hissed under his breath about 20 seconds later, still loud enough though for his date to hear, which brought nothing but shock to Caroline, who had no clue, or care, that Larry's Ex had left him for her Boss several years earlier.

Thankfully, Larry took out his misplaced and ill-timed anger on the car's accelerator and the two were back at Caroline's apartment complex in less than 10 minutes. Sitting in the car as it idled, Caroline waited for a few moments before getting out in hopes Larry would say something to prove the last half hour was nothing more than a bad dream.

"Maybe I'll call you sometime," he finally offered, revving the engine several times to break up the uncomfortable silence after the words left his mouth.

"Fuckin' hope not," Caroline answered before getting out and slamming the car door hard.

Fishing her keys out of her purse, the radiating heat of anger in her cheeks sure to evaporate any tears that dared fall from her eyes, Caroline made her way up the steps to her third floor apartment. Fighting to get the key into the series of locks guarding her door with her drunken and shaky grip, once inside Caroline groaned loudly before kicking her heels across the room.

Closing the door quickly behind her and collapsing against its supportive frame, Caroline didn't know whether to laugh or cry from how the night had turned out.

"Fucking sucks to be single," she spat before dropping her woozy body down on the sofa.

Rubbing at both her sore feet for a few moments, Caroline looked over at the clock and a brief sparkle glimmered in her eyes.

"It's only 11:35," she thought out loud. "Bet Steven hasn't gone to bed yet... "

"Don't even think about it Caroline," another voice quickly and thankfully interrupted. "The only thing you need right now is some sleep!"

There alone and motionless on the sofa, Caroline was left to fight all the demons that had so doggedly haunted her.

"I can't sit here and listen to this," she finally screeched out loud, pulling herself up from the sofa as her tightly bound breasts half spilled over the top of her dress.

"Thank God I've got tomorrow to sleep this off... I know I'm gonna feel like shit in the morning," Caroline inherently knew as she staggered down the hallway towards her bedroom.

Standing at the foot of the bed in the dark, having missed twice trying to turn the light switch on as she walked through the doorway, Caroline's head bobbed between her shoulders from the combination of inebriation and fatigue. Reaching down to blindly try lifting her dress up her body and over her head, she was forced to take a seat on the mattress before falling sideways on top of the comforter at the foot of the bed.

"GGRRRHHH," Caroline groaned as she tried to right herself, finally getting the tight sequined gown all the way off.

Catching her breath for a moment before continuing, Caroline then reached around her back and unclasped the duel snaps of her bra. A second later, both her full, matronly breasts were freed and bounced like a pair of dark, robust melons against her chest.

"God... that's better," she sighed in relief before folding the bra straps all the way over shoulders.

Raising her hands to her bosom, Caroline clumsily pinched and kneaded the chocolate brown orbs in attempt to get the feeling back in them after they spent the entire evening in such binding constraints.

"Every-fucking-body else at that party is probably getting laid right now... Well everybody but Larry and that's his own Goddamn fault," Caroline drunkenly giggled before her bitter malaise kicked back in.

Nothing left on her body but her lacy white, French cut panties, Caroline rested her weary body on the edge of the bed before making her first attempt to lift her left feet off the floor so she could begin sliding down her underwear.

"You're too old to be wearing things like these, Caroline," she chided herself, remembering the look of 'these must be a gift for your Daughter' on the clerk's face at the boutique when she bought them for the party, just in case something had happened afterwards.

The vague hint of her arousal slowly crept upwards as Caroline worked her panties off and dropped them to the floor.

"I can't even give this damn pussy away!" she chuckled with a mix of anger and emptiness that only humor could conceal before she collapsed backwards on the center of the bed.

"Just go to sleep Baby... just go to sleep" Caroline told herself several times even though her right hand kept brushing at the dense tangle of pubic hair between her legs and the still slick and buttery slit that it hid.

Laying there in the dark, her head spinning as she stared up at the ceiling, Caroline tenderly rolled her fingers side to side around the outer rim of her pussy until her index finger slipped inside the puckered folds.

"OHHH," she sheepishly squealed under her breath.

"Dont do this, Caroline," a guilty voice in her head scolded.

Having grown up in a nice, conservative Christian home, masturbation was a topic, and an act, completely foreign to Caroline until she went away to college. Even then, meeting up with Steven so soon after enrolling, having a man whose sexual appetite was as healthy as his, the need to gratify herself never was an issue. Even after he had started sewing his oats elsewhere during their marriage, Steven still had enough left in the tank to satisfy Caroline the one or two times a week that she had grown use to.

Upon becoming single however, between the inability to find quality dates in the pool of available men and situations like she just had with Larry when she did find a date, Caroline gradually came to discover the joys, albeit guilty ones, of self gratification. So it was with great reluctance she added two more fingers to the one already inside her brimming quim at the same time she began rotating her thumb over the spiked nub of her clitoris.

"DAMN," Caroline huskily gasped, her body slithering on top of the sheets as she clamped her hand tight inside her swollen cunt with her powerful thighs.

Her glassy eyes half slitted open, Caroline could feel electrical pulses bombarding her brain each time she stabbed her fingertips through the oily sheath of her womb. Twisting her head to the side, Caroline caught a glimpse of the phone and the alarm clock sitting on the stand next to the bed.

"I bet he's still up," a needy voice inside of her murmured. "It's only 7 little digits."

"No... we won't be doing that... I don't care how drunk you are," the last vestige of Caroline's strength decided even though she pressed her fingers deeper inside her vagina when her mind fixated for the moment on her Ex-Husband.

Thrashing to the side until she had done a complete 180 on the bed, Caroline found herself flat on her belly with her hand still compressed on top of her fuming slit.

"God... these sheets are going to get filthy," she thought for just an instant before beginning to hump her crotch up and down on her painfully arched hand and wrist.

Raising her ass into the air slightly so that her crotch was a few inches off the bed, Caroline created a better angle to swipe her fingers through the stoked furnace between her legs.

"Let's get this over with quick," she seethed, desperate to get what little consolation from the evening she could before she collapsed and finally fell asleep.

Trying her best to conjure the quickest image to help her cum, Caroline was left with one bad option after another. Her first inclination was to think about her date for the night. The way that the evening had ended left such a vile taste in her mouth however, Caroline briskly slapped at her pussy trying to put Larry out of her mind.

Her next option, while more erotic and certain to get her off, wasn't at all healthy. Allowing her mind to slip back to Steven, as it always did in times of weakness, Caroline slowed the motions of her hand just enough until it felt like her pressed together fingers were a real cock jabbing at her cunt.

"Oh God that feel's good," she groaned as her fingers scissored through the damp, musky folds of her sex.

Knowing she could get herself off relatively quickly to the thought of her Ex, Caroline angrily fought that temptation until another equally perverse vision filtered into the fibers of her mind. Increasing the speed of the thrusts inside her pussy once again, images seemed to entangle behind Caroline's rapidly fluttering eyelids until she yelped out loud at the vivid memory of dancing in the arms of her Boss, earlier in the evening.

Her drunk and flimsy legs unable to support her writhing frame, Caroline felt her knees give way until her belly had collapsed once again on the covers below. Disorientated, Caroline kept her fingers wedged inside her cunt even though her legs were fishtailing steadily lower on the mattress. Spreading her feet apart as she grinded down towards one of the diagonal corners of the bed, Caroline blindly slapped and spun her fingers through her dripping wet pussy.

The tips of her toes tapping the floor as she franticly humped her own hand, Caroline could literally feel her rapidly building orgasm igniting inside of her.

"YESSS... SSSSS... SSSS... YYYESSSSSSSSSSSSSSSSS," her voice crackled through the vacuum of silence in the bedroom, every bit of fatigue, desperation, angst and need she felt fusing together inside her body in a massive and debilitating release.

The explosive power of her orgasm was so intense, Caroline's feet pressed down on the floor just before her entire body shot backwards, as if possessed, until her momentum had slammed her back flush into the 6 foot tall post rising from the corner of the bed. Her spine snugly in line with the hand carved, antique post, Caroline bucked and writhed against its unforgiving presence until she had scrubbed and squeezed every last bit of accumulated lust from her spasming snatch.

Her back lowering against the bed's support when her legs finally gave out, Caroline drowsily pulled her fingers free from her distended labia and fell forward, face first into the ruffled sheets below and within a matter of minutes, was sound asleep.

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