Maggie May Ch. 01

Story Info
A beautiful cougar wannabe seduces her young boss.
3k words
4.45
151.2k
53

Part 1 of the 7 part series

Updated 10/31/2022
Created 09/27/2009
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Wake up Maggie I think I got something to say to you
Its late September and I really should be back at school
I know I keep you amused but I feel I'm being used
Oh Maggie I couldn't have tried any more
You lured me away from home just to save you from being alone
You stole my heart and that's what really hurt

John walked into his office with his head down on this rather dreary Monday morning only to startled by a most eye-catching, alluring sight. Long, stocking-clad legs were draped over one of the cushiony chairs in front of his desk. He immediately raised his head, already knowing instinctively who these legs belonged to, Maggie Cox.

"Good Morning, Sunshine, I understand your weekend was not the best."

John stopped dead still at not only the unaccustomed sight of one of his department managers in a much shorter-than-usual black miniskirt, but also because he was dreading that the word had already gotten into the gossipy world of his department store that he and his girlfriend had finally broken off their sometimes stormy relationship. Well, in actuality, his girlfriend had broken it off, and worse yet, for another guy, that bodybuilder jerk off from the local-yokel small town police department.

John sighed mournfully, while simultaneously feeling a surprising stirring in his suit trousers, as he couldn't help but notice that the always impeccably attired Maggie was looking more daring today than perhaps he had ever seen her. She was adorned in a while silk blouse to augment the beautiful skirt, and her auburn hair that was sexily speckled with salt-and-pepper streaks on her temples had apparently been highlighted over the weekend. Yes, John noticed such details, especially on Maggie.

Even though she was almost twenty years his senior, John had always had a wild crush on Maggie. Yet he deemed her unapproachable and off-limits for a variety of reasons, not the least of which was her age. Also, Maggie was married, he assumed happily so, to a very prominent physician in this small community. Quite frankly, John felt as if he was out of Maggie's league, chronologically, socially, and sexually. From the first time he saw Maggie at the store meeting that was held several months ago to announce his promotion from a position in the home office in Philadelphia to the store manager in this swanky upscale suburban store, John felt his pulse quicken immediately. Three simple letters came into John's mind every time he saw Maggie, from up close or from afar. "Wow!"

He tossed his briefcase towards his desk, which missed and clunked noisily to the floor, and he sighed deeply again. "Maggie, please, please, tell don't me that the word is out already about Kathy and me."

Maggie uncrossed her long, lean legs, very pleased that John watched her intently as she did so, and she made it a point to not even attempt to lower the skirt which had hiked to mid-thigh, exposing her stocking tops, as she rose and moved towards him. John flinched backwards as Maggie eased towards him, her five-foot-nine inch frame augmented further by her 4-inch black heels, and glided ever so gracefully into John's personal space, now inches from him, so close that John could feel Maggie's soft, spearminty breath on his cheek, and smelled the intoxicating scent of Maggie's perfume.

Today's choice of perfume was AnaisAnais, John realized, because it was the same scent that Kathy fancied wearing recently. John's mind flashed back to that scene no more than a week ago as he visualized himself again buried between Kathy's legs, tasting that wonderful nectar of Kathy's cunt that was enhanced by this sweet cologne, that Kathy enjoyed liberally spreading on her inner thighs. John wondered in this instant if Maggie did the same.

Maggie did something she had never done before, though truthfully, both Maggie and John wished they had done to each other long before: invaded the other's personal space. She took her beautifully manicured, slender fingers and ruffled them through John's curly hair. The couple froze for a second, unknowingly immortalizing this moment as the one that would forever change not only their own relationship, but inalterably affect their very lives. Maggie smiled at John with a matronly look of sympathy as she gazed deeply at John with her sultry gray-blue eyes.

"Yes, John, the word is out, and you know why?" John shook his head slowly, conscious that Maggie's fingers were now softly stroking the nape of his neck. Goose bumps arose on his forearms, and another more prominent lump arose well below. He fidgeted uncomfortably.

Maggie continued, enjoying the impact she was most obviously having on her much younger boss. "Because that big dickhead cop was in here over the weekend bragging to some of the ladies in cosmetics about how he was nailing the store manager's girlfriend. Or, should I say, his now EX-girlfriend. I'm using his words, darlin', not mine."

John blushed, a strange combination of embarrassment, anger, and arousal that he had actually heard the sophisticated and classy Maggie use such a term, apt though it may be, to describe Kathy's latest bedmate.

"You're kiddin' me, right?", John asked sadly as he slumped down into his chair, unwittingly causing Maggie caress to cease. He didn't want that to happen, and was sorry he moved. "He actually had the, um, balls, to come in here and brag about it?"

Maggie hovered over him, her waist now eye-level and inches away from John's face. She did not move backwards. Instead, she next crouched in front of him, and lightly touched him teasingly on the lower thigh, just above the knee. John hoped that Maggie hadn't noticed the growing, twitching bulge in his pants, but she did. Oh, yes, she most certainly did.

Maggie softly cooed, "John, may I be very candid with you?" John nodded tentatively, and glanced over Maggie's shoulder and out of his office door, and hoped that no other arrivals were entering the outer office this early on Monday morning. Maggie and John were usually among the first in the store on a daily basis, and apparently, today was no exception. Thank goodness, John thought.

"I've been watching you swoon over that little tramp almost ever since you got here." Maggie paused for emphasis, and watched closely for John's reaction. Little did Maggie know that the reaction that John was now mainly focused upon was fighting, unsuccessfully, to keep his erection from bursting through his zipper. He was amused, though, at Maggie's use of the word 'tramp' to describe Kathy, and had to agree, in hindsight now, that it was pretty accurate. John had deduced for weeks now that Kathy's main intent was to bed the new boss, and having accomplished that, she moved on to her next conquest. The painful realization has not dawned on John until he had time to reflect on things during this past lonely weekend.

Maggie herself now glanced over her own shoulder. Once convinced that they were still alone, she moved even closer to John, her chest and torso now pressing into his legs, and her hands now more firmly caressing John's thighs. Maggie herself was now glad that her own arousal was not evident. Unbeknownst to John, her thigh-high stockings were attached to a crotchless garter belt, and her own juices oozed from between her legs. She was now in the role of gentle yet undeniable predator, seducing an unwitting prey, emotionally vulnerable, but, oh so, delicious.

"What you need, John, is a real woman, a mature woman, not one of those little girls that you seem to get caught up with." John gulped nervously. It was true, he was sometimes too much of a gentleman for his own good. For a 28-year-old professional and successful man who certainly did not lack from many an attractive woman's attention, John still was relatively naive. Up to now, his sex life was relatively uneventful, conventional, vanilla. That was about to be altered.

Maggie pressed even closer now, the tips of her fingers now tantalizingly close to the throbbing bulge in John's crotch. If she was concerned about any intruders interrupting this strange yet erotic scene, she did not at all let on. Her eyes never left his lap as she continued her synopsis.

"And, take that old girlfriend of yours, too. That ice queen, Stephanie. Remember when you started going out with her when you were working in Philly? Remember that she was my assistant here at the time? Do you know what she used to say about you?" John again shook his head, his anxiety fighting a tug-of-war with his very acute arousal. His hips rose instinctively from the chair, squirming in frustrated sexual tension.

Maggie smiled and licked her full lips lasciviously. She continued in a low-pitched ,sultry growl. "She used to whine that you were too big for her, that she couldn't take you all in, that you hurt her with your size. Can you believe that?" Johns eyes were transfixed on Maggie's now, and he saw a look in Maggie's eyes that he honestly didn't know that she could exude. Sheer unadulterated lust. "That would NOT be the case with a REAL woman, I assure you."

Maggie then stood up abruptly, as she heard the rustle of co-workers entering the outer office lobby a nanosecond before John did. With complete pose and decorum, she pulled the hem of her skirt down her thigh as she sang in a happy, lilting voice, "So, boss, is it OK if I make a 2 o'clock appointment with you to discuss sales and staffing? I'll check your calendar with Madeline."

John moved his rolling leather chair tightly under his desk in the event that Madeline came into the office to offer her customary morning salutations. Madeline was a woman in her mid-sixties, and a protective mother hen to John, and she no doubt would want to come in and offer her own condolences over John's latest failed relationship. The last thing John needed was for Madeline to notice his raving hard-on literally bursting from his zipper.

On cue, Maggie twirled and leaned on the door frame of John's office entrance. "Morning, Madeline! Think you can spare me a half-hour of our boss' busy day later on this afternoon? Say, two-ish?" Madeline murmured her consent, and with that, Maggie winked and sashayed out the door, giving John a barely discernible last wiggle of her mini-skirt-clad tight ass. John's fleeting thought was that it was almost anatomically impossible for a 47-year-old to have a butt that firm. yet at the same time, the bulge in his pants made him very curious to discover more for himself.

"Jesus H. Christ," John muttered to himself. "What just happened here?" He then mouthed the one word that Maggie always seemed to evoke from him. "Wow!"

Two o'clock could not have come fast enough as far as John was concerned. Fortunately, as always on a Monday after he had the weekend off, there was a lot of catching up to do, so the clock moved relatively quickly. Madeline was inquisitive, but respectful when it became obvious that John would rather not delve into details on his break-up with Kathy. John had to admit to himself that the escapade with Maggie this morning had indeed served to essentially divert his thoughts way from his 'tramp' ex-girlfriend to what may transpire with his suddenly overly flirtatious 'mature' shoe department manager. He decided to take the proverbial bull by the horns once he met with Maggie at two.

Maggie was her usual punctual self and arrived at his door armed with loose-leaf binders and sales reports. Her arrival was preceded by the scent of that amazing perfume, so John knew she was in close proximity even before he saw or heard her. The scent itself produced an involuntary Pavlovian-dog-like response within John's loins. He shook his head and again uttered that magic word just before Maggie entered. "Wow! What she does to me."

Maggie's hair was brushed back from her forehead and slightly tossled. She had been primping herself in her stock room, and that included using one of the heels from her own 4-inch pumps as a impromptu masturbation device just minutes before the meeting. Maggie wondered if John could sense the unmistakable aroma of her sex mixed with her perfume. She hoped so. She wanted to drive him fucking crazy. John had no idea, just yet, how much Maggie had lusted after this handsome young man herself since he came into her life several months ago. Within the next half-hour, her intentions would be made quite clear.

John had already seated himself at his circular conference table and patted the chair next to him, indicating Maggie to join him in the next chair, under the auspices of mutually reviewing the reports. Maggie was pleased at this gesture by John, as it was the first time he had ever been emboldened enough to be comfortable with being so near. As Maggie gracefully lowered herself into the seat, her long legs again exposed to mid-thigh, she made it a point to rub her calves against John's, who smiled knowingly. he got off and called out the door, "Madeline, I'm going to close the door for a little bit so we can concentrate undisturbed, hold my calls for a bit, please, thanks!"

He turned to Maggie as the door shut behind him, and felt his cheeks rising with heat, blushing. "I want to thank you for getting my mind off of Kathy all day, that was very altruistic of you." Maggie smiled and curtsied mockingly, her bra visible through her blouse as she bowed. John's brow furrowed as it did when he was pondering something, a little idiosyncrasy that Maggie found cute and charming. "Now, I have a question for you." He paused while Maggie stared at him with those piercing, sparkling eyes. "Just what is it that I need in the perception of this real woman?"

Maggie rose from her chair and lifted her ass onto the table in front of John, sliding the paperwork and binders aside. She lifted one knee, the other leg dangling over the table's edge, and as she did so, her skirt hiked enough to give John a view of her upper thighs, so that he could see the lacy stocking tops, but no further. His breathing accelerated, and his face flushed even more. He was mesmerized at the view, and again that 'Pavlovian' rock hard response took over his other senses. Maggie had the unfettered attention of all three of the Committee members in this little meeting: From the Heart John, Between the Ears John, and Below the Waist John. Being the most prominent member, Below the Waist John was now canceling out any other votes from the other members.

Maggie adjusted her knee, pulling it closer to her chest, which resulted in her skirt hiking perhaps an inch higher, so that John could now see the outlines of her swollen pussy lips beneath the dark skirt. He certainly smelled her nectar as well, and for just a second, amused himself with the thought that men emit visible displays of arousal while women exude olfactory clues. "Viva la difference," he mused silently.

Maggie exhaled softly and asked, "John, may I entertain you with a story?" John, of course, nodded his assent, his eyes barely lifting from Maggie's crotch.

"Before I begin my story, you must answer this next question either 'yes' or 'no'. No 'maybes' or other disclaimers. Ok?" Again, John meekly nodded, completely in her spell by now, any silly aspersions that, as so-called boss, he would be in control of this meeting now cast aside. It was Maggie's ball game and she threw out the first pitch, a heater.

"Do you want to fuck me?"

This at least caused John to alter his gaze from Maggie's genital area. The butterfiles in his stomach leaped into his throat, and he struggle valiantly to maintain any semblance of composure. He blushed even more deeply, his face now a crimson, and Maggie spread the leg that was not pulled to her knee even wider apart. His lips moved, but no sound came out except the faintest of whimpers.

He felt hypnotized, almost entranced, and yes, scared shitless.

Maggie looked at him scoldingly as she ran her own hands under her skirt and raised her ass from the table, and pulled her skirt up to almost her navel, so that John could now see her pussy clearly, shaved, bare, gleaming with juices wafting over her lean thighs. She took one of her hands and cupped his chin.

"Don't wait too long, you have three seconds. One.......Tw...."

"Yes, oh my God, yes, yes, is that a trick question!?!?"

Maggie leaned down and held his chin more tightly and lowered her lips onto his. He tasted her myriad of flavors immediately, the strawberry lip gloss, the fresh hint of mint on her breath, the cool texture of her long, wet tongue lapping on his own, her full lips sucking him deeply into the warmth of the back of her mouth. Maggie swirled her tongue around the young man's mouth for a few teasing seconds, and then tossed her head backwards, releasing his face from her grasp. John felt like his cock could lift the table on its own, a magical levitation trick spawned by the sheer overpowering sensation of the blatant eroticism of Maggie's actions. If this was what he'd been missing when Maggie referred to a 'real woman', he was fully submitting and surrendering to this amazingly beautiful predator unilaterally.

"Very good, that was the correct answer. Now, it's story time." Maggie brought her other leg onto the table now, and grabbed her knees at the same time, fully exposing herself to John. She took two of her fingertips and pulled her labia apart, showing John the saturated slickness within her slit. A third finger slithered down and rubbed the hood of her clit, now poking through her folds. John leaned closer, but Maggie playfully shoved his forehead away.

"Behave, at least for the time being. Good things cum to those who wait. Such as, my pussy. But all in good time. Now, listen."

So, good readers, who wants to hear Maggie's story?

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11 Comments
RoryOmoreRoryOmoreover 6 years ago
Great song great beginning

Love your style.

Hope to read more.

equs64equs64over 7 years ago
Cheating wife stories

always get me hot. Especially those in the work place because honestly, that is where most affairs begin. I should know. I know I am going to enjoy the series.

AnonymousAnonymousover 11 years ago
me too

who doesnt?

AnonymousAnonymousover 11 years ago
me!

I do

FRSWRITERFRSWRITERover 14 years ago
wicked good

knew an older babe named maggie too she was great

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