Though an accomplished and confident woman, Monica was more nervous than expected on her first day as the new Chief Information Officer. It wasn’t a new position for her as she’d been a CIO for two companies prior to this one. The difference was the reason she’d been asked to resign from her last post, which she’d successfully kept secret during her interviews, but on the job now, she worried it might not remain a secret. The IT community is one where it seems everybody knows everybody else, so her reputation might follow such channels and come back to haunt her.
She started the day with many introductions, as the CEO took her to meet all the officers and VPs. She was usually pretty good at remembering names, but the names started running together by about the tenth person. Next were her immediate subordinates. It went better having an organizational chart to study beforehand. Each wanted to introduce her to the next level of staff, but she postponed that for a time when her memory had more capacity.
She met with each supervisor to get a feel for them and their current tasks and projects. She would start with System Administration to get a feel for infrastructure and then DBAs for health checks on several major systems. Development was next broken into two teams: one for ERP programmers and the other for web developers. The Help Desk fell within the responsibilities of the Sysadmins, but she wanted to meet the people that many employees would see as the face of IT. Each meeting went well, though males and females alike were initially stunned by the image of their first female CIO.
Monica was a beautiful woman, and though she dressed conservatively for work, she had an innate sensuality that came through regardless. Long, straight, naturally blonde hair was the first thing people found unusual on a forty-something professional. Her face was strong and confident, with small but full plump lips and piercing blue eyes. Her Nordic ancestry had also blessed her with an equally inviting body. With some of the maturity of her age, it was nonetheless one that a woman of any age would be proud to have. A shapely form of average height, with a well-defined waist and long legs, was further enhanced by sumptuous, firm breasts and a pert bottom.
She usually dressed in business-like pant suits and various expensive tops, but her pants and underwear were selected, even tailored, to show off what she saw as her best feature: her perfectly tight ass. She loved to turn around and catch passing men who’d noticed her body stopping to stare at it. She visited a gym a few times each week to keep her overall figure but with more exercises to maintain its matchless shape.
As the days and weeks passed, she eventually met all of the hundred or so employees in her charge. She was struck by how young many of them were. Typically, there was an older supervisor, one or two more experienced staff members, and the rest that looked to be just out of college, probably their first job after getting their computer science degrees. She figured it was a result of the company’s rapid growth that made it difficult to quickly find enough well-seasoned recruits. Still, there were few complaints about IT in general, so they must have been doing their jobs adequately.
Settled in her position and familiar with the projects in process, she got busy with her work. There was a quarterly report due soon, and her reports were something she’d always excelled at. A fan of outlining reports and other lengthy communiques, she needed her favorite outlining app installed and called the Help Desk.
“Yes, we have that app. A couple of other executives use it, too. I can install it remotely right now if you like.”
“I’d prefer someone installing it in my office where I can keep an eye on what they’re doing, so please send someone up?”
“Of course, Monica! Someone will be there shortly.”
She was both pleased and surprised that he’d used her first name in addressing her. Not usually a fan of ‘Miss’ or ‘Ms,’ she had instructed all her staff as she met them to call her Monica, but it often took longer than this for them to start doing so, and the further down the corporate ladder the person was, the longer it took.
A few minutes later, there was a knock on her open door. She looked up to see one of the younger staff waiting obediently at the door to be invited in.
“I’m from the Help Desk, Miss Moore. Come to install that app you wanted?”
“Come in! I’m afraid I’m still learning names here. What’s yours again?” she asked.
“Simon, Miss Moore. Simon Dupree.”
“Hello, Simon. You can call me Monica, and thank you for coming so quickly,” she said as she got up from her desk to let Simon "drive."
“You’re welcome, Miss … um, Monica,” he said hesitantly as he took her chair.
She smiled at the shy young man as he took the thumb drive on a lanyard from around his neck and plugged it into the laptop. She sat on the edge of the credenza behind him and smiled at how many times he turned slightly to see if she was still there. He was done installing the app in a few minutes and rose from her chair.
“All done! Is there anything else I can do for you?” he asked, unable to look her in the eye. “These cables to your docking station are a jumbled mess. Would you like me to straighten them out?”
“Yes. Thank you!” she said, still enjoying watching the trim young Simon work. “How long has it been since you completed school?”
“Almost two years. I interned here for my last year, so I’ve kinda been here three years now,” he said proudly as he untangled the half dozen cables leading from the back of her docking station. “That should do it. We have various kinds of cable wrap that would make that all look neater if you like?” he said, seemingly looking for reasons not to leave.
“That would be great, but not right now, okay? I’ve got a report to write now that I have my outlining tool. Thank you for coming, Simon. It was nice to meet you!”
“You’re welcome! It was nice meeting you too, Miss Monica!” he replied, heading for the door.
She smiled as he left. He reminded her of someone at her last job who was overly polite, but she didn’t dwell on the thought, afraid of where it might lead her.
In the following months, any occasion to call the Help Desk resulted in a visit from Simon. He always seemed happy to see her, but he never changed how he addressed her as Miss Monica. She took more notice of his trim but pleasing body over time. He had broad shoulders but an undeveloped chest that didn’t enhance it as well as it might. In addition to a handsome but youthful face, she also noticed his nicely shaped, not-so-youthful ass when he’d been crawling around under her desk taking care of another cable problem.
It was nearly a year since she’d started this job, and everything was going well professionally but not personally. Divorced for over a decade, she’d had her share of men, but those her age never met her unusual requirements. She found the younger generation more pliable and willing to bend to her wishes, though that had gotten her into trouble before and cost her her last job.
She tried hard to resist the temptation, but last night’s date had been such a disaster. After weeks of tame dates with this man and equally tame sex, she’d had enough. It was early morning as she sat with her coffee, lamenting the state of her romantic life, when Simon showed up unannounced.
“Good morning, Miss Monica! I have a security update that needs to be installed at the user’s station. May I?” he asked in his usual polite tone.
“Good morning, Simon, and yes, you may,” she replied as she surrendered her chair.
Standing more to his side rather than behind him, she noted the exuberance with which he handled every problem with her. Whether it was his handsome form or the dismay regarding last night’s debacle, she felt a familiar twinge between her legs. She cautioned herself that this was how it started last time, but it didn’t seem to help.
“All done!” he said, jumping up from her chair and interrupting her reverie.
“What? Oh, thank you. Thank you, Simon,” she said with a sad smile.
“Is everything okay, Miss Monica?” he asked, noting her mournful look which was such a contrast to her usually friendly demeanor.
“No,” she started absentmindedly, revealing more than she wished. “I mean, yes. Everything is fine, Simon. Thank you again,” she said, still with an element of melancholy in her voice.
Her eyes followed him out the door and down the hall, still feeling that touch of arousal. For some reason, it occurred to her that she’d never had anyone else from the Help Desk come to her office. Others had answered questions and offered help on the phone, but when an office visit was necessary, it was always Simon. She decided to find out why and picked up the phone to call his supervisor.
“Help Desk! Eric speaking.”
“Good morning, Eric. I have a question.”
“Of course! What do you need to know?”
“It seems that the only one of your people who comes to my office is Simon, and I’m wondering if there is a reason for that?” she asked.
“Yes,” he chuckled, “I’ll tell you if you promise not to tell him I told you.”
“Um. Okay,” she replied with intrigue.
“The first time he did some work for you, he came back gushing at how nice you were as well as how pretty he thought you were. Really! He went on and on!”
“Ah! I see,” she replied, chuckling herself.
“Seeing how taken he was with you, we let him take all your tickets that call for a personal visit. Is that a problem? Is he bothering you in some way?” he questioned, wondering if he should have told her.
“No. Not a problem at all. He’s friendly, polite, obedient, and helpful to a fault. Once he thinks he should do something else, it isn’t easy to talk him out of it, but that’s a good thing in my view. You can continue to follow this practice,” she finished, wondering if Eric would think it strange.
“Thank you, Monica. Is there anything else?”
“No. Thank you, Eric,” she finished and hung up.
She was at war with herself about whether she should take advantage of the situation. She was nearly certain that Simon would be a more-than-willing participant in what she’d been thinking about, but the angel on her shoulder told her to be cautious. "I can be cautious and still have some fun," she told herself but tabled the matter until the following day.
She went home, having nearly decided to abstain from the daydreams that had been plaguing her all afternoon. What she had in mind wasn’t all that risky, but it would likely lead to situations that were. Despite having made a decision, the thoughts didn’t subside and, in fact, became more insistent as the evening wore on.
Standing in front of her mirror in her underwear and nightgown, she took stock of her appearance, wondering if there was anything she needed to work on at the gym. She decided there wasn’t, and the specter of Simon entered her mind again, thinking he’d love to get his hands on her body.
Tearing off her nightgown, she made for the king-sized bed, pulled the covers back, and threw herself on the surface with one hand on her tits and the other between her legs. As fingers played in her wet slit, images of Simon’s face between her legs appeared in her mind’s eye, and her breathing accelerated quickly.
"That’s it, Simon! Take my panties off!" the dialog played in her head, and she pulled her panties down and off. Both hands slid up the inside of her smooth thighs and plunged into her clean-shaven pussy. Two fingers inside curled up to find that special spot while the other hand coaxed her clit out of hiding. Her middle finger slid up and down her sodden slit while her thumb maintained pressure on her clit.
“Oh! Oh! Oh yeah! Oh yeah! Ha, ha, ha, HA!” she gasped aloud as her fingers fucked her needy pussy, but it was her clit that brought her to the brink of orgasm and pushed her over the edge.
Between one of her better self-induced climaxes and the imaginary presence of Simon, her decision not to pursue Simon came into question again. She fell asleep while plotting what she might do tomorrow.
The morning brought more conflict with the two sides of her conscience. One argued that he was much younger, she hardly knew him or how he’d react, and it wasn’t worth the risk. On the other hand, her needs had been unsatisfied, almost neglected for so long, and she was confident he had a submissive streak a mile wide that would keep him from telling anyone about it. The "other hand" won, and she dressed for work as she’d planned last night.
Nearly everyone noticed the change in appearance, which she ascribed to a hot date that evening, a partly true lie, or so she hoped. It wasn’t that it was overtly sexy, just that they hadn’t seen her in a skirt very often, and this one was shorter than the others. She enjoyed the attention of men and women alike, catching them ogling after she’d passed by.
A colleague of Simon’s rushed to tell him what she’d seen, knowing he had more than a passing interest in Monica. "Wow!" was the word that finished her observation, leaving Simon hoping he’d be called to her office for something, anything today.
He had to wait till mid-afternoon, but he rushed to her office when the call came in. “Wow, is right,” he said aloud, but softly to himself when he saw her from the hallway, pacing in her office and talking to a recording device. Her formal white blouse wasn’t tight but showed her assets in the best light. The skirt, probably part of a business suit, hugged her hips but was not overly tight from below to its hem a few inches above her knees, which allowed her to walk easily while showing off the thighs no one had seen before. He stopped in his tracks just to enjoy the view but was embarrassed when she looked up directly at him.
“You like, Simon?” she asked when he finally entered her office.
“Yes! You look very nice today, Miss Monica!” he said, hoping it didn’t sound too enthusiastic.
“Thank you. I’m hoping to meet someone later,” she explained with a smile, wondering what he’d think when he knew it was him.
“What’s wrong with your computer?” he asked as the ticket had just said several things weren’t working.
“No sound, no monitor and no webcam. I think I might have kicked something loose under the desk. These heels always seem to catch on something,” she replied, smiling at his glance down at her feet to see the three-inch spike heels.
She sat in her chair and rolled it back from the desk, inviting him to crawl under it to see what she’d intentionally disconnected.
“You just kicked the power cable to your docking station loose. Tell me if everything comes back on,” he instructed as he plugged it back in.
“Yes, it’s all working now,” she said as she rolled up closer to the desk, blocking his escape with her skirt hiked up another few inches to allow a wider spread of her legs.
“There’s something I can do to make sure…” he started but stopped, suddenly speechless at the sight of her spread legs and the tight white panties between.
She let him stare. His eyes averted only for a second to look up at her, wondering if she was aware of what he was seeing. Her smile told him she was, and he licked his lips while he stared for a few seconds more, now noticing the defined slit and plump lips on either side. He wondered if she was just teasing him or if she had a more interesting motive. Either way, he had no idea how to react to someone of her importance in such a situation. She rolled her chair back to allow him out from under her desk.
“I can make sure it doesn’t come out again. I need some wire ties and a couple of tools,” he said as he stood up, his body still quivering inside and hoping for another peek.
“Can you do it later? I have a lot of work I need to get done. Can you come back at six?” she said, smiling at his reaction to a time when nearly everybody would be gone.
“Yes. Yes, I can do that! I’ll see you then?” he said, only realizing his unintended double entendre after he said it.
“I’m sure you will! Thank you, Simon!” she said as she rolled back up to her desk and pretended to be busy while he walked out the door, noticing him taking another look back.
Tipping her chair back once he was out of sight, she congratulated herself on the first step in her plan, executed flawlessly. She’d felt her arousal starting as soon as he walked in the door and wondered whether he’d seen any evidence of it.
Six o’clock arrived, and the office was as quiet as a morgue. Simon showed up dutifully on time with his tools and went straight under her desk to do his work without saying a word. Already nervous, his agitation was ramped up when he heard the office door close. Working in the cramped space was difficult, but his excitement made it worse, and several times, he fumbled his tools and had to start over.
"Holy shit!" he thought when he heard her sit in the chair and roll it up to the desk again, just like before. He cautioned himself not to assume anything and wait for her to make her intentions clear, worrying at the same time whether doing so might let an opportunity slip away. He wasn’t good at being the aggressor, so he hoped her actions so far showed she was.
“All done,” he said as he squirmed out from the tight space under the desk drawers.
“Not quite, Simon,” she said in a sultry voice.
He turned to sit on the floor under the center desk section, expecting to see her spread legs and white panties, but gasped, “Hoh!” when a dramatically different view was offered. Perched on the edge of her chair with her skirt pulled up to her waist, Monica presented her smooth, bare pussy inviting Simon’s attention. Two plump pink lips with a well-defined slit, glistening with her arousal, separated as her legs parted further, revealing the inner folds, pale and pink, begging for his tongue.
“See something you like?”
“Yes, Miss Monica!” he sighed, his words expelled on a breathy gasp.
“Just Miss will be fine, Simon. Would you like a taste?” she asked, their eyes briefly connecting with a slight nod. “Eat me, Simon!” she said as she rolled forward an inch or two.
Reaching first with his hands, they slid up the warm, soft thighs he hoped to feel clamped on his head at some point. With a surprisingly gentle touch, his fingers played in her wetness, caressing the lips and tiny creases within while teasing her clit with fleeting brushes.
“Oh yeah!” she cried repeatedly, not expecting his sensual approach. Assuming an inexperienced young man would dive right in and, quite literally, "eat" her pussy with little or no finesse, she was quite pleasantly surprised by his tender touch.
Having developed a technique in college, he prided himself on his ability to please a woman with just his fingers and tongue, and, as a result, he was pretty popular with the girls who learned of his reputation. He’d lost count of how many pussies he’d tasted, as they were often one-time affairs with girls who just wanted to test him. Virtually all left him gushing, in more ways than one, about his exceptional skill, improved with each new experience. He quickly found he loved being asked or even told, to lick yet another pussy.
By the time he’d slipped a single finger inside, stirring her juices and grazing her G-spot, he was ready to give her his tongue. He kissed her savory lips, sucking on the tender tissue between them before extending his tongue, traversing her slit with just the tip, and dipping into her honey pot. He had her body squirming, pushing against his face as his light touches became licking and sucking. Expecting a starving man presented with a huge meal, she preferred the way he sampled her like a fine wine.
“Oh God! I’m gonna cum, Simon!” she gasped, surprised at how quickly and gently he’d brought her to this. With fingers in her pussy and his tongue concentrating on her clit, she passed the point where she thought she’d climax, the extraordinary tension building still.
Finally, with his head held captive between her legs, her body went rigid as the first wave crashed ashore, her hips jerking and thighs trembling as the unexpectedly incredible orgasm progressed. Smaller shocks came as he lightly touched and kissed her succulent snatch.
“Oh my God. Simon! Where did you. Learn to do that?” she asked between panting breaths.
“In college, Miss,” he answered with the skill of a comedian delivering his punch line, and she laughed. “It was an elective course,” he added, making her laugh again. “I had a girlfriend who really liked it, and she taught me how to please her. When she broke up with me, apparently she told others of my … ability,” he said after a pause. “Before long, I had girls coming to me, some brazen or drunk enough to just ask me straight out if I’d lick them.”
While he gave her the history of his learning cunnilingus, he would touch her again and kiss her shiny, wet lips as though offering comfort for an ordeal.
“I really love doing it, Miss!” he said, looking at her with pleading eyes.
“And it shows, Simon. Oh God, it shows! Are you up for some more?” she asked, showing unusual consideration rather than just taking what she wanted.
“Do you like facesitting?” he asked hopefully.
“On the floor!” she exclaimed as she jumped up and moved to the open space between her desk and the windows.
Simon lay down as Monica discarded her skirt to avoid it getting in the way. With her feet on either side of his shoulders, he smiled at the view of looking straight up into her crotch.
“You want more, Simon?”
“Yes, please, Miss!” he replied and watched her dripping wet pussy slowly descend toward his face, a couple of drops falling on his face, which he scooped up with a finger and licked clean.
She didn’t know whether it was the new position or the anticipation of another orgasm, but she felt a jolt pass through her body the second her lips touched his mouth. The "Oh my Gods" and "Oh yeahs" flowed freely as she ground her pussy into his unyielding face. It had been a long time since she’d done this on a floor instead of a bed and she cautioned herself not to press too hard.
Simon didn’t need to do much while her hips rocked to and fro, wiping his nose, mouth, and chin with her teeming pussy. Her exclamatory words became muddled grunts and gasps as she pressed her advantage. He was one of the many who stole looks at her exquisite ass, and while he couldn’t see it now, he enjoyed the feel of the perfectly round, soft, and smooth cheeks in his palms as he alternately squeezed and stroked them lovingly.
Her movements now jerky, it was time for his tongue to take over, running rampant through her slit and poking inside. He looked up to her face. With her eyes closed in rapture, her hands manhandled her ample tits, reminding him that that was where he usually started, and he wondered if he’d ever get to see or touch them.
“Jesus, Simon!” she exclaimed as she squirmed on his face while the effort of holding herself over him started to show. “I’m cumming! I’m cumming! OH!” she yelped when she felt a fingertip pushing into her ass, climaxing with the well-timed intrusion.
She fell forward, supported by her hands on the floor, as she quivered inside with the glorious orgasm. Sitting up, her body resting just above his hips, she reached back to feel for the erection he must still have. She smiled at him, feeling the prominent bulge in his slacks.
“Mmm, I think I can take care of this!” she offered as she stroked it. Turning around, with her pussy and ass in his face again, she worked the closures of his slacks. He lifted his hips for her to slide them down, feeling them banded around his thighs where she left them. “Ooo, you’re full of surprises today, aren’t you?” she asked as she took his larger-than-average cock in hand, smiling when she heard him moaning his appreciation.
“Sixty-nine?” he requested, never having enough of a pretty and sweet pussy.
She didn’t reply but leaned over to take him in her mouth.
“Oh, Miss!” he cried as she swallowed him whole, feeling the tip enter her constricting throat. It was a first for him as none of his admiring college co-eds had ever done it. “Please, Miss?” he grabbed hold of her hips and pulled her down onto his face again, his tongue instantly in overdrive. She squirmed on his face again, humming her gratitude with a mouthful of his cock.
The two rocked, wriggled, and writhed as they both gave and got unprecedented pleasure. In incredible bliss, he started lifting his hips as if fucking her mouth and removed his mouth from her pussy long enough to warn of his cumming. Wetting his finger in her pussy, he pushed again on her backdoor and, getting it in to the second knuckle, he finger-fucked the tight, little hole.
“I’m cumming, Miss!” he warned again, and given no choice, he shot his load into her mouth.
His thighs trembled with the spectacular ejaculation, and while he pumped several strings of his creamy seed into her mouth, he still licked, enveloping her whole pussy into his mouth, slathering it with the flat of his tongue and pumping his finger in her ass. Seconds later, his face was again awash with her delicious nectar.
She rolled to the side, sitting on the floor next to his prone body, still stroking his shrinking dick. Neither said a word for a minute or two, relishing the incredible experience that rivaled the best they’d ever had.
Simon sat up with the sadness of a pleasure now past on his face. He couldn’t imagine this turning into anything but a one-time fling, let alone any sort of relationship. He readied himself for the common rejection of a woman taking what she wanted and giving little in return. He waited for her to say something before he made any overtures that might be declined.
Monica couldn’t believe how much better it had turned out. Having only expected this young man to scratch an itch, she was unprepared for these feelings, not only of the risk well worth taking but of a strong desire to do it again. Finally, she spoke.
“Simon, that was, I don’t know, extraordinary? Astonishing? Breathtaking?! I imagine you’re having mixed feelings about having just licked your boss’s pussy. You have nothing to worry about, and I want you to know I’d love to do this and more again if you’re willing,” she offered, stroking his cheek gently.
“Really! You mean it?” he replied, his answer evident by his reaction.
“Yes, really,” she smiled. “I’ll say nothing of this to anyone, and you must do the same!”
“Yes, Miss! I will!”
“I mean it, Simon! If I hear you’ve said anything to anyone, the consequences will be unpleasant and possibly painful!”
“I understand. I won’t say a word!”
She retrieved her panties from a drawer where she’d left them and put them and her skirt back on. He stood up to pull his underwear and pants back on and watched with an open mouth as she worked her tits back into place. She tucked her blouse back into the waist of her skirt and fondled them again, seemingly getting them comfortable. She’d noticed him staring when she started; the second time, it was for his benefit.
“Would you like to touch them?” she asked, his wide-eyed look all the response she needed. She turned her back to him, grabbed his hands from his sides, and pulled them around her, placing them on her tits and letting him enjoy their heft. Again, he handled her with a level of expertise she’d not been expecting.
She turned around, still in his arms, and kissed him twice, one short and one long, with her hands around his waist.
“Remember!” she said, pulling away. “Not a word!” she added and patted him on his butt.
He walked out the door in a state of euphoria, thinking it must be a dream and wondering what sort of painful consequences she was threatening.
--===<<<O>>>===--
Will he test her threat to find out what she meant by 'painful consequences? I hope you liked the beginning of this new story and remember to 'Like' and/or 'Favorite' it if you did. Thanks For Reading!!
