Catching the Boss

Originally Published on WordPress October 8, 2018

Catching the Boss

Jessica let out a wanton cry of pleasure as her orgasm erupted through her lithe, trembling body.  Her slender fingertips continued sliding in and out of her quivering, clenching pussy.  She clutched the oversized pillow against her chest and screamed into it, muffling her howl of pleasure.  No sooner had her body’s convulsions stopped than her iPhone’s alarm went off.  Gasping softly, she reached over and tapped the surface of the phone, silencing the alarm.

“Damn,” she muttered.  “I was hoping to get a short nap after that.”  Jessica rolled out of bed with a weary sigh.  “Work, and another day of sexual frustration await.”

Jessica took a peek outside her bedroom curtains at the early morning sky, and quickly decided on the day’s wardrobe.  She walked into the bathroom and started the shower.

Damn it, what does it take to get that insufferable man to notice me, she fumed.  I’ve done everything but tear off my clothes and throw myself at him.  Some friend Karen is, giving me that advice too.  I’d likely get fired and a reputation as a slut. 

Jessica hurried through her shower and wrapped her towel around her.  She rushed through styling her curly deep brown hair as well.  She walked into her closet and pulled a dark blue dress from the rack.  She held it out in front of her, studying it for a moment and then sighed.

“Stuffy and dull,” she lamented.   “No wonder I can’t get him to notice what great tits I have.”

Jessica’s gaze ran slowly over the rows of neatly hung clothes on each side of the closet.  Her eyes fell upon the small section of clothes that was intended for dating; all of them tasteful yet provocative.

“It’s been ages since I’ve been on a date,” she sighed.  “if I can’t get laid that way, maybe…”

She pulled a white semi-sheer blouse off the rack and stared at it.

“Well,” she sighed nervously, “maybe it’ll get his attention without going TOO far…”

Jessica bit her lower lip and stared at the blouse.  She quirked an eyebrow, let out an uneven sigh and dropped her towel from her lithe frame onto the floor.  She slipped the sateen garment on and buttoned it up.  She left the top few buttons undone, leaving the top of her impressive cleavage exposed.  She took a deep breath and turned around, looking into the full length mirror at the end of the closet.

Jessica gasped, slapped both hands over her breasts and turned beet red all at once.  “Oh my God, my nipples and areola are too dark to do this.”  “They’d be visible clear across the office,” she gasped.

“I can do this,” Jessica said softly.  “I just need to be a little less Karen and a little more lady-like.”

Jessica rummaged through her lingerie drawer and found a sheer, lacy cream colored bra and matching panties.  She quickly unbuttoned the blouse and slipped it off.  She ran her hands softly over the curve of her full 34D breasts and imagined Mr. Jacobs fondling her.  The thought sent an erotic chill down her spine and made her clit tingle with hungry anticipation.

27 years old, and I can’t stop fantasizing about a 40 year old man, Jessica thought.  Maybe I do have daddy issues…

Jessica slipped into the bra and fastened the front clasp.  She turned side to side, examining the bra’s fit and ability to hide her large, dark nipples.  She cocked her head to the side uncertainly and then pulled on the blouse again.  Repeating her routine, she saw that the combination of the bra and top was as close to ideal as possible.  If one looked closely, they could see the lace detail of her bra through the blouse, and just a vague shadow of her areola as well.  Sexy, but in a subtle way that Jessica decided she could live with.

She glanced at the clock, and realized she needed to hurry if she was going to get to work on time.  She grabbed a pair of thigh high nylons and rolled them up the soft curves of her legs.  Then she dark skirt that clung alluringly to the curves of her hips.  Perfect for this situation, she thought.  It came as close to complimenting her firm but slender rear as any of her clothes.

Jessica wished she had the ass to match her boobs, and imagined if she did, that she might have better luck attracting men.  Her friends and dates had all told her that she was gorgeous, but that didn’t stop her from being self-conscious about the modest curve of her petite behind.

She slipped on a pair of running shoes, and stuffed a pair of 4” Prada stiletto heels into her work bag.  Jessica left the closet and cast a glance towards her jewelry box.  She carefully went through it, looking for just the right pieces to accent her outfit.  She decided on a diamond solitaire pendant on a chain just long enough to place the diamond barely within the valley of her cleavage.

After putting on matching earrings, Jessica quickly did her makeup, gathered up her stuff into her work bag, and scurried out the door.  She’d barely made the train but arrived at work on time, keeping her perfect record intact.

Jessica wasn’t expecting the looks she got as she got off the elevator.  It felt like half the office was undressing her with their eyes.  Even Brandi, who was openly lesbian, licked her lips as she passed Jessica on the way to their respective desks.  The look Brandi gave Jessica made her blush and press her thighs together as she walked.

Jessica felt a little dirty, dressed this way.  It was exciting and embarrassing at the same time getting all the looks she did.  Maybe, just maybe…  This will finally be what it takes to get Henry Jacobs to notice me, she thought.

Jessica opened the door to Mister Jacobs’s office and stuck her head in the door.  As expected, he was in there working away already, studying reports and dealing with paperwork.  He’d come in to work early every day since his wife had filed for divorce six months ago.

“Mister Jacobs,” Jessica said, “I… I’m here.”  She shifted back and forth and let out a nervous breath.

“Perfect timing, Miss Clark,” Mister Jacobs replied.  “Come in, Jessica.”

Jessica flashed a brief, lopsided smile.  “Timing and ability to anticipate what you need are part of why you hired me, sir.”  Jessica entered the office and then quietly closed the door behind her.

“Very true,” he replied with a light chuckle.  “You’re an amazing assist…”, Mr. Jacobs started.  He looked up from his paperwork and his train of thought became completely derailed.  He stared at Jessica, speechless.

“Is… something wrong, sir?” Jessica asked nervously.

“Uhm, errr…  no.” Mr. Jacobs said.  The focus quickly returned to his face.  “I have the list of things I need you to do today.”  “I’ll send the list via intra-office email.”   “I… will be in meetings with other some of the other Vice Presidents and other executives all day.”

“…Oh,” Jessica replied.  She sighed and slouched slightly forward.

“I’ll need you at a few points today to work up memos on the results of the meetings,” Jacobs said.

“Of course, sir,” Jessica said as she straightened her posture.

Jessica left the office and sat at her desk just outside.  She spent the day making phone calls, scheduling meetings and travel for Mr. Jacobs, and handling emails and paperwork as usual.  The few times she was called in to talk to Jacobs were brief and almost coldly businesslike.

Five PM came and went, and the rest of the office went home for the weekend.  Ever dutiful, Jessica stayed at her desk.  She sat with her elbows on the desk and head in her hands.

Why do I put myself through this, she asked silently?  Every night I work late for him, and hope he notices me.  All I get for it is barely better than average pay raises.  She glanced back at the closed office door and took a deep breath.  One last all or nothing attempt, she told herself.  If I can’t get his attention, I’m done with this, she fumed.

The office door opened and the division president walked out.  “Good meeting, Henry,” the president said.  “I like the ideas on the merger in particular.”  “Work up a final proposal and I’ll submit it to the board.”

“Good night, Mrs. Davis,” Jessica said.  “Have a good weekend, ma’am.”

“Thank you, Jessica,” the president replied.  “You too.”

The president exited the office without another word.  Jessica sighed and stood up.  She looked at her faint reflection in the blank computer monitor.  Taking a deep breath, she unbuttoned her blouse one more button, opening it nearly to the bottom of her breasts.  She sighed and picked up the FedEx envelope from her desk.

She knocked on the office door and slowly opened it.  “Mister Jacobs?” she asked.

“Come in, Jessica,” Jacobs replied.  “What are you still doing here?”  “We closed an hour ago.”

“You know I never go home while you’re still here and might …need me,” Jessica said.  She tried to sound seductive, but her nervousness completely ruined her effort.

“Yes, you’re certainly dedicated,” Jacobs replied.  He paused, for a moment and then noticed the envelope.  “More paperwork?”  he asked, a bit of weariness showing in his voice.

Jessica nodded. “This paperwork should make your day though,” she said with a smile.  “It’s from your lawyer.”  “Your divorce is final and you’re free of that cheating shrew at last.”

Jacobs gave her a disapproving look.  “Language, Miss Clark.”

Jessica looked downward and nodded.  “Yes, sir,” she said meekly.  “You know I’ve never liked the way she treated you though.”

“I appreciate that.” Jacobs replied firmly.  “I don’t disagree either,” he added, almost cracking a smile before turning serious again.  “However, it’s not your place to comment, and you know very well that I insist on strict professionalism in the office.”

“Yes sir,” Jessica replied, her head still lowered.  “I apologize.”

Jessica brought the envelope over to Jacobs.  She waited until he had just begun to turn in his chair to face her, and then leaned forward to put the documents on his desk.  Feigning surprise, Jessica gasped and turned to face him, placing her full, lightly perfumed breasts inches away from his face.  Jessica did blush, but from embarrassment at such a desperate maneuver.

Jessica slowly moved away, leaving the papers on the desk.  “Oh…  my…” Jessica struggled.  “I… I’m sorry, Mister Jacobs.”

Jacobs, clearly flustered, struggled for a few moments to regain his composure.  “Uhm…  yes…  That… will be all, Miss Clark.”

Jessica sighed.  “Yes, sir,” she said dejectedly.  She moved towards the door, trying to put an extra sway in her hips as she walked.  She got half way to the door and dropped her pen.  She bent over at the waist, thrusting her butt towards a startled Henry Jacobs.  Jessica picked up the pen, sighed and did her best to keep the sashay in her walk as she left the office.

“Have a good weekend, Miss Clark,” Jacobs said as she closed the door behind her.

On the verge of tears, Jessica packed up her things into her work bag.  How could I be so stupid, she sobbed mentally.  All I accomplished today was humiliating myself and acting like a desperate tramp.  She picked up her bag and started to leave, too dejected to even change shoes, when she heard a faint moaning coming from Mr. Jacobs’s office.   Oh my gawd!  Is he having a stroke or a heart attack?  She dropped her work bag and darted into the office.

She stopped in the doorway, her mouth open in complete shock.  There in front of her, sitting in his office chair with his pants around his ankles and his hand on his manhood, was Mr. Jacobs.

“WHAT…  THE…   FUCK!?!” Jessica blurted out.

Jacobs sat there shocked, unable to find anything to say.

“Is THIS your idea of professionalism?!?” Jessica demanded.  “If so, I really don’t think HR is going to fucking approve.”

“Now wait a minute…” Jacobs said, half panicked.  He tried to get up, but Jessica shoved him back down into his chair.

“Were you whacking off thinking about me??” Jessica demanded.  “Were you??”

“Y…  yes.” Jacobs said with a humiliated sigh.

Jessica backhand slapped him across his surprisingly muscular chest.  “Do you have any idea how that makes me feel, you bastard?!?”

“I…  I’m sorry,” Jacobs stammered.  “Please don’t go to HR though.”  “This would ruin my career and reputation.”

“Maybe you should have thought of that before you exposed yourself and started yanking your pud while thinking about your executive assistant in the next room.” Jessica growled.  “After all I’ve done, I deserve better than… this.”  She crossed her arms and glared at Jacobs, her expression twisting into a wicked smile. “Well, looks like the shoe is on the other foot now…”  “You’re going to give me what I want or HR is going to hear everything.”

“I’m well to do, but hardly filthy rich,” Jacobs replied.  “I’m not sure what you’re hoping to get from me, Miss Clark,” Jacobs replied in a tone that was a mixture of nervousness and annoyance.

“You stupid man,” Jessica growled, “I’ve never cared one bit about your money.”  She moved to the chair and straddled it, sitting on Jacobs’s lap facing him.  She started unbuttoning her blouse.  “You’re going to fuck me… good, long and hard.”

“What the hell has gotten into you, Jessica?” Jacobs demanded, completely shocked.

“What has gotten into me is the indignity of hoping for three long years that my boss would notice how I’ve wanted him to take me to bed and claim me as his.” Jessica replied angrily.  “Three years of going home and having to use toys to satisfy my needs and fall asleep alone.”  “Working late, supporting you through your divorce with that frigid bitch…”  “All to only find out after practically begging you today to fuck me, that you’d rather jack off than have the real thing.”  “Well if taking it is the only way I’m going to make it happen, so be it.”

Jessica tossed her blouse aside and unclasped her bra.  She ran her fingers through Jacobs’s thick hair, aroused by the touch of silver at the temples of his otherwise light brown hair.  She draped the bra around his neck and then pulled on each side of it, bringing Jacobs’s head up against her breasts, then arched her back and shook her chest, jiggling her breasts against Jacobs’s head.  Jessica smiled as she pulled back and saw the shocked look on his face.  She climbed off his lap, grabbed him by the tie and pulled him out of his chair.

“On your back, now,” Jessica commanded, pushing against his chest.

Jacobs half fell backwards and ended up on his back laying on the dark carpeted floor of the office.  Jessica quickly unzipped her skirt and pulled it and her panties down at once.  She gave Jacobs a predatory look of hunger.  She got down on all fours and crawled over Jacobs, and then sat on his chiseled abs.  She hungrily loosened and removed his tie and then unbuttoned his shirt.  She ran her hands up his toned chest, and through his light chest hair.  Jessica scooted up and pinned Jacobs’s arms with her legs, sitting on his face.

“Eat my pussy,” Jessica commanded as she began rocking her hips, grinding her pussy against his mouth.  Jacobs did as he was ordered, slowly, uncertainly at first.  His tongue darted inside and along her wet slit.  With each passing moment, his efforts became more focused and earnest until he was ravishing Jessica’s womanhood with an almost crazed passion.

Jessica squirmed and bucked with every lick and kiss.  She cried out in pleasure repeatedly as her breasts bounced and jiggled wildly.  ‘Oh…  gawd…  YES!” Jessica screamed as her orgasm exploded out of nowhere.  She clutched her breasts with one hand and steadied herself with her other hand on Jacobs’s chest as her body shook almost violently.  Jacobs gave her no relief though as he continued to tongue lash her wet pussy like a starving man.   Orgasm after orgasm rocked Jessica’s long denied body as she thrashed and cried out in ecstasy.  Panting and covered in perspiration, Jessica finally jumped back off of Jacobs’s face as her eighth or ninth orgasm hit.

“Oh… Fuck…” she gasped.  “Nobody has made me… cum like that before.”  Jessica slid down Jacobs’s body and lay there pressed against him as she caught her breath.  She slowly and sensually licked her juices from his face, then leaned in and kissed him deeply.  She stared deep into his eyes with a wicked look.  “Starting to see what you’ve been missing all this time?” she asked mischievously.  Jessica gave his balls a light squeeze and then began stroking his muscular seven inch cock.  She waited until he was moaning softly and rock hard.

“Good boy,” she said with a wicked grin.  She got to her feet slowly and then gave Jacobs a lewd look.  “Now get up,” she said firmly.  “You’re going to fulfill a fantasy I’ve had since I first saw you.”

Jacobs gave her a confused look.  His expression and body language telling that he was still in shock over what was happening.  Uncertain how to react, he climbed to his feet.  Jessica grabbed his wrist and pulled him towards the desk until they were where his chair normally sat.  She kissed him passionately on the mouth then along his jaw line until her lips came to his ear.

“Now…” she whispered in a breathy, seductive tone, “You are going to fuck me and make me scream your name the way I’ve dreamed about.”  “…And I am going to show you how a real woman satisfies a man and make you forget all about that bitch.”

With her heels on, Jessica was nearly as tall as the 6 foot 1 inch Henry Jacobs.  She grabbed his cock in one hand, just under the tip, wrapped her left leg around him, and positioned his cock right at the entrance of her wet pussy.

I must have rehearsed this scene in my mind a million times, Jessica silently gasped.  Now, I’m finally going to have him inside me.

Jessica laid back on the desk, pulling Jacobs on top of her and skillfully guiding him fully into her in one single move. Her back arched as she felt him deep inside her.  “Oh god, YES!” she cried out.  “Give it to me!”  “I want all of you!”  She wrapped her long, slender legs around Jacobs’s hips loosely and began rocking her hips.

Jacobs began thrusting into Jessica’s clenching pussy.  The look on her face told her that her control was driving him wild.  That in turned drove her to a ravenously hungry state as she rocked her hips to meet his every passionate thrust.  Jessica wailed in pleasure between passionate shouts of “Yes!”  To Jacobs’s surprise, his eager young executive assistant had her first orgasm in under a minute.  Jessica screamed at the top of her lungs as her body spasmed and convulsed.  Her pussy clenched his cock hungrily and quivered as she grabbed for the edge of the desk trying to ride out her orgasm.  He was even more surprised when she looked at him as the orgasm subsided and demanded more.

“More,” she demanded hungrily.  “I need that magnificent cock.”  “Fuck me like you wish you could have fucked her.”

Jacobs obeyed, fucking her with a hunger that almost scared Jessica and clearly rivaled her own.  He leaned down and began kissing and suckling her breasts, massaging them with both hands as he rutted against her.  Jessica climaxed again, and again… she’d lost count but knew it must have been around a dozen times when she finally felt Henry Jacobs’s body tense and his thrusting become more urgent.  His earlier soft grunts became loud moans of pleasure.  Jacobs started to pull out of her when Jessica wrapped her legs tightly around his waist locked her ankles together and pulled him deep into her.  With a loud cry of pleasure, Henry Jacobs tossed his head back and pumped his cum into Jessica’s body.

She tossed her head back and wailed in ecstasy as she felt her deepest fantasy fulfilled.  The orgasm was her most intense yet, and her body shook wildly as she squirted all over her boss’s twitching, throbbing cock.   Her energy gone and her long-starved libido now satisfied, Jessica collapsed limply against the desk, panting and gasping.  She looked weakly up at the shocked Jacobs.

“Was that your plan, young lady?” he demanded.  “Get yourself pregnant and live off child support?!?”

“N.. no…” Jessica stammered, caught briefly off guard by the allegation.  “I’m on the pill,” she replied plainly, regaining her wits.  “Even if it happened, would it be so bad having a woman who craves you finally give you the heir that bitch wouldn’t?”

Jacobs took Jessica firmly by the shoulders and sat her up on the edge of the desk.  “And just what makes you think you’re worthy of taking her place, or entitled to make that decision at all?” he demanded, giving her a stern look.

Jessica now was completely shocked.  The overwhelming thought that she’d pushed things too far completely disarmed her.  “I…  I adore you.” She stammered weakly.  “You… must see that.”  “Ev… everything I’ve done, all the extra hours I put in.”  Her jaw trembled slightly as she looked up at his stern, disapproving eyes.  “You deserve somebody who wants you as much as I do…”  Some… somebody willing to treat you like a man should be.”

“What I deserve…” Jacobs said sternly, pulling her over to his chair, “is an assistant and woman who knows her proper place.”  He pulled Jessica prone over his lap and began spanking her hard.

“Ow!” Jessica cried out.  “Please, stop, OW!”  His hand came down over and over on her slender ass, leaving it bright red with every impact.  “Please, stop sir.” Jessica wept.  “I’m sorry.”  “I’ll do whatever you want.”

“We’ll see about that,” Jacobs snapped.

He moved Jessica off his lap and then pushed her into a bent over position on the desk.  Jessica gasped, terrified and not sure what was coming next as Jacobs tied her hands behind her back with his tie.  Before she could utter a sound, Jessica felt his stout cock slip back inside her.  She cried out in a mixture of shock and pleasure as he again filled her drenched pussy and began pounding away vigorously.  Jessica cried out as every thrust quickly reignited the flames of her desire, and took them down a dark path she didn’t even know existed inside her.

Jacobs grabbed a handful of Jessica’s hair and pulled her head back, firmly but not enough to hurt.  “You’re going to behave from now on, aren’t you?” he demanded.

“Ye.. yes, sir,” Jessica cried out in between shrieks of pleasure.

“And you’re going to be an obedient little slut for me, aren’t you?” Jacobs demanded in the same firm tone as he brought his free hand down hard against her tender, reddened ass.

“Yes!” Jessica screamed.  “I swear!”

Jacobs took Jessica from behind for almost a half hour bringing her to several more orgasms before cumming again deep inside her.  All the while she wailed in pleasure, and sometimes pain as he occasionally slapped her ass to remind her that he was now in complete charge of her body.  Her orgasm as Jacobs climaxed inside her that second time was so intense that Jessica felt her eyes cross and she almost blacked out.  She felt Jacobs slowly pull out of her, and the exhausted busty brunette rolled weakly over on the desk.  Jacobs gave her a stern look, pointed at the ground in front of him and snapped his fingers.  Something dark inside of Jessica compelled her to obey and she found herself intoxicated by the feeling of being controlled by this powerful man.

Jessica slipped down to her knees and without a word began hungrily licking and kissing the half flaccid cock in front of her.  She licked it clean, savoring the taste of their mixed juices on it.  Without a word she then took it in her mouth and began vigorously sucking on it, her head bobbing back and forth.  Jacobs let out a hungry growl as he felt his cock springing back to life.  Without another word, he pushed Jessica onto the ground, and mounted her.  He slung her legs over his shoulders, entered her again, and began taking Jessica with a wild abandon.  The ferocity of his desire scared and exhilarated Jessica, and pushed her to several more orgasms.  The last thing she remembered before passing out was Jacobs cumming in her once again and that pushing her to the most intense orgasm of her life before everything went black.


Two months later, Jessica sat by the pool in a gold bikini when her phone rang.  She rolled her eyes slightly when she saw the caller ID, then picked up the phone.

“Hello, Karen,” she said with an amused sigh.

“No, I don’t miss the job at all.” she laughed in response to her friend’s question.  “The new one is much better.” She added, glancing down at the huge diamond ring on her left hand.  She listened bemusedly as Karen said something in response.

“Nope, it hasn’t gotten old at all,” she replied.  “He treats me like a queen in public and his dirty little whore in bed, and I love every minute of it.”

Jessica laughed at the next question then rubbed her slightly swollen stomach.  “No, he’s so thrilled about it he’s even more frisky than before.”  “Good thing too, since my out of control hormones have made me almost as sex crazed as you,” she added with a slightly mocking laugh.

Jessica let out an annoyed gasp at the next question.  “NO!” she half yelled.  “You most certainly can not come over for a threesome!”  “Henry Jacobs is all mine.”  “I won’t even let him have a female assistant.”  “And I remind him every night why I’m all the woman he’ll ever need.”

With that, Jessica hung out the phone and stretched out on the chaise lounge.  Henry wouldn’t be home for another two hours, so she intended to enjoy the sunshine and rest up for what she was sure would be another passionately exhausting evening.

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