tagMatureMaggie May Ch. 06

Maggie May Ch. 06


To familiarize yourself with the characters, it would behoove you, dear reader, to start at the outset of this series to tag along. After all, prolonged foreplay leads to the greatest climax.


All I needed was a friend to lend a guiding hand.

But you turned into a lover, and Mother what a lover.

You wore me out.


Charlotte's inadvertent mistake when she had assumed Maggie had the phone to her ear led to the plan that John and Maggie had now concocted. Once the two had shared various insights and intuitions, they became convinced that Charlotte's ultimate intentions, though certainly carnal in nature, were anything but altruistic.

It was a far different plan than the one that they had shared with Charlotte, who was under the impression that the duo in the hotel room was seriously contemplating Charlotte's invitation for a private party at her house on Sunday evening, just the three of them. While on one level both Maggie and John found the offer incredibly arousing, they were also prudent once they had mutually discussed Charlotte's actions and potential motives. So, Maggie and John had decided on the best of both worlds for them, to have their cake and eat it, too. So to speak.

Maggie began to get dressed as John lay on the bed and watched her admiringly. She was still caked in cum, and her body oozed the scent of the pair's intense sexual sessions over the past many hours. John had taken Maggie up on the suggestion that he utilize the spacious hotel suite and luxurious bed to slumber for the evening, understanding that Maggie had to be home in time to make breakfast for her teenaged daughter in the morning, but couldn't help but to inquire, "Aren't you going to at least shower before going home to the mad doctor?"

Maggie stood in front of the mirror, but instead of brushing her mussed and curled and semen-matted hair back to some semblance of normalcy, she tossed it into even greater disarray. "Nope, my daughter will be asleep, and I want him to see me like this. Since he was kind enough to finally divulge that he's been fucking a twenty-eight year-old with big tits, I'll leave it up to him to surmise that his trophy wife just got thoroughly fucked by a twenty-eight-year-old of her own." Maggie glanced down at John, still prone and naked on the mattress. "With a BIG cock, mmmmmmm." Maggie bent down from the waist while still clasping her bra over her breasts, her nipples still pointing like bright pink pencil erasers, to place a slow, wet kiss directly on John's purple cock head.

She rose and continued gathering up her accessories and the rest of the belongings. "So, tell me again what Charlotte did at the divorce trial? And, how do you know the facts?"

John rolled over onto his side and propped up his head with three or four of the feathery pillows, and emitted a loud, exhausted sigh. "I told you, my best friend is one of the editors of the Daily News. The paper was kind of strong-armed into not revealing all of the sordid details of the divorce trial by Old Man Olson's powerful legal firm, but my buddy told me the inside scoop. And, they are juicy. And kind of eerie." Mrs. Olson was the epitome of the scorned, manipulating, vengeful woman in the private eye, while maintaining an angelic-like, Mother Theresa persona to the public.

What had been reported by the local print and television media was that one Charlotte Olson, local Main Line socialite, debutante and on the boards of numerous philanthropic agencies throughout the Philadelphia region, had won a seven-figure settlement in her highly-publicized divorce case against her philandering, hot-shot attorney partner of an international law firm husband, several years back.

What John had discovered on the sly from his newspaper crony was much more detailed. John was indeed a conspiracy believer by nature, and the sidebars shocked but ultimately did not surprise him.

Almost a decade ago, Charlotte Olson had numerous reasons to believe that her wealthy, powerful husband had been engaged in numerous extra-marital activities. She had secretly conspired with one of Counselor Olson's own partners in his law firm, a man who Charlotte knew had long been a business enemy of Mr. Olson's, and irrationally jealous of his partner's ruthless rain-making abilities.

Charlotte had enticed her husband's partner with that most powerful weapon of seduction, her own pussy. After several weeks of fucking the partner, Charlotte had convinced him that the most effective way to undermine her own husband's alleged unethical legal behaviors was to secretly install a series of pinhole camera in his office, augmented by listening devices.

The end result was even better than Charlotte could have hoped for. Though the tapes ultimately were ruled inadmissible as evidence at trial, the damage had ben done and was irrevocable. Both Charlotte's husband and her lover were dismissed from the bar, and Charlotte's husband permanently relocated in shame to the Cayman Islands, a shattered career and family life in his rear-view mirror, crushed personally, professionally, and financially.

It turned out the Mr. Olson had used his own office to conduct most of his illicit deal-makings of the sexual nature. Months worth of videotapes had shown the esteemed, distinguished, brilliant lawyer in less-than-dignified various acts of debauchery. Cross-dressing. Dominance and submission. yet the most damaging tape of all was the rather disturbing video of Mr. Olson raping a young, male first-year lawyer at his firm, the young man bound and gagged and blindfolded on his couch, being pummeled by a nude, whip-bearing Mr. Olson, who shouted threats in the young lawyer's ears that he would tell NO ONE.

Yep, that was worth a hefty seven-figure settlement by the prodigious law firm to not let that piece of tape be made public. Mrs. Olson agreed to the settlement offer under the condition of complete confidentiality. The firm further mitigated its potential public-relations damage by using its substantial local influence upon the publishers and station managers of the local print and electronic media, respectively, to keep this entire incident on the hush-hush.

Everyone lost something in this whole unimaginably sordid situation, even the now filthy rich and newly independent Charlotte Olson. She had sold her soul to the legal devils in return for several million dollars and got to keep her board positions and public image unblemished. However, Charlotte's only daughter, Sarah, at the time a young college student in the Carolinas, who admired and revered her father and found her own life to be irrevocably shattered by the familial humiliation, was determined to never speak to her mother again. What price does one pay for wealth, Sarah would always wonder.

Maggie pondered this entire situation as John recanted his insider's knowledge of Charlotte's background and character. While John spoke, Maggie's mind flashed back to some of her own interactions with Charlotte, now rather curious with the benefit of clarity of data and hindsight. Charlotte had been the one to actively encourage Maggie to engage in her own extra-marital affairs as justifiable revenge and retribution for Maggie's own husband's infidelities.

Maggie now questioned to herself why Charlotte had gone so far as to lend Maggie the Hilton Head villa, as well as a willing and waiting young paramour, for Maggie's own excursion into extra-marital encounters. Maggie now began to also ponder why Charlotte had seemed so unreasonably agitated when Charlotte had discovered that Maggie's unplanned second tryst in Hilton Head, with the charming maitre'd of the Sea Pines restaurant, had not taken place at Charlotte's house.

Maggie had been lured in and convinced by Charlotte to film her latest encounter with John under the auspices that Maggie and Charlotte could view it together and derive tremendous voyeuristic pleasures. Maggie was at first understandably hesitant, yet her reluctance waned when Charlotte showed Maggie snippets from Charlotte's own personal collection of sex tapes, starring none other than Charlotte Olson. Charlotte's various co-stars in the films were numerous, young, well-endowed, well-built young men, who serviced Charlotte, long and hard, acquiescing to Charlotte's demands and incredibly voracious appetite for cock.

The image of the video of Charlotte fucking three young studs who appeared to be barely out of their teens danced in Maggie's head. She had never seen nor imagined a mature woman acting in such an unfettered, uninhibited, and yes, whorish manner. When Maggie had first viewed the tape in Charlotte's den, with Charlotte narrating the action to Maggie in a soft, slow, animatedly seductive voice, Maggie thought she would flood the couch with her excitement. Maggie drove home shortly thereafter, and had to stop several times along Lincoln Highway to manually relieve her own pent-up arousal. Maggie was reeled in by Charlotte, she had to admit it, hook, line and sinker. Maggie's own deep desires and energies had been repressed for virtually decades, and with Charlotte, she had found an experienced and nurturing source of encouragement for Maggie's own pursuits of sexual explorations.

She also wanted to experience such electronic activity herself, and at the time, she was more than eager to share with her personal mentor. Maggie had no way of knowing, until now, that Charlotte had a history of using such illicit videos for personal leverage. Armed now with this knowledge, and her inherent trust in John and his well-conceived plan, she was determined to turn the tables of Charlotte and attempt to beat her at her own game, though without the domino-like painfully punitive repercussions on many lives. The plan that Maggie and John were prepared to enact would only entrap Charlotte in her own salacious web. She gave John a soft, slow, passionately grateful kiss as a sincere 'thank you' for the most incredible sexual afternoon and evening of her life, yet Maggie's kiss contained more meaning for her.

Maggie had recently been awakened to many new adventures in her life, sexually and otherwise, and she intuitively sensed that she was about to embark on a new, tremendously exciting and powerfully fulfilling chapter of her sexual and emotional life.

On the other hand, as Maggie left the room and John wearily reached to turn off the light for an evening of much-needed sleep, he summarized the night's event in one word before dozing.


Fridays were always hectic in the department store and this had been no exception. Sixty percent of a department store's sales were made each week between the hours of noon Friday and close of business Sunday, so there were a lot of preparations for the weekend to accomplish. John conducted his weekly staff meeting with his department managers, and he and Maggie went about their business in the normal fashion, Maggie rattling off her sales projections and staffing plans in front of the group without the slightest indication that John's cock had been buried in each of her holes barely twelve hours before.

On the surface, she was her usual unflappable and impeccably attired self, the consummate industry professional. On the inside, however, from the recent unfamiliar pounding it had taken last evening, her mouth and cunt still felt stretched from the John's massive girth filling her fully. She wanted more, she was insatiable now. She knew John was going out of town this weekend, in conjunction with their plan, and she would not see him again until Sunday, with Charlotte. Yet, she burned for more cock, she needed it soon, she had to have it, something, in the next forty-eight hours. Rather than being exhausted, she was fervently energized with sexual adrenalin.

She thought of that age-old joke from her days as a country girl in her youth, told by her older, more daring schoolmates. "Cock-a-doodle-do, any cock'll do!" She made a call to a sitter for care for her daughter on Saturday night. She was going to go prowling for fun Saturday, she decided. Her pussy was still too sore to fuck, but she didn't have lockjaw, either. She was going to practice her oral abilities on some soon-to-be fortunate young man, a hard, young strangers's cock to suck, to hone her skills, to temporarily sate her desires.

For his part, the sleep had done John wonders, and he, too, was sharp and alert and invigorated by the sinister brilliance of their idea. In John's mind, the beauty of their plan was that they would beat Charlotte at her own game, but not until after they had enjoyed Charlotte's legendary sexual talents themselves.

Maggie had confessed to John that watching the beautiful Charlotte Olson demonstrate her body and sexual escapades on film had aroused a long-repressed wanting within Maggie to experience a woman for the first time. Charlotte had made this offer to them on the phone the prior evening, for a threesome to be held at Charlotte's house on Sunday night, yet John and Maggie had initially played coy and would not commit, at least not to Charlotte, much to Charlotte's dismay and dissatisfaction. Privately, though, the two conspirators had agreed that the premise had intrigued them tremendously. Despite her unattractive moral character, it could hardly be argued that Charlotte Olson was anything but a sensationally beautiful, desirable object of lust, by either gender. This would be a revenge fuck at its best, the tables turned on Charlotte this time.

John had booked his flight to Savannah, Georgia, for early Saturday morning, while also booking the return flight back to Philly for mid-day Sunday. Ironically, there were no direct flights to Savannah, so the connecting flight would be in, of all places, Charlotte. John had also made the call for an appointment with one Sarah Olson, now a young real estate agent on Hilton Head Island, for two o'clock on Saturday afternoon in Sarah's Palmetto Dunes office.

John had spoken to Sarah personally, and described himself as a business man looking for an upscale time-share opportunity on the island, explaining that Sarah had come highly recommended from a mutual acquaintance from Sarah's home town of Philadelphia. John promised to a curious, though flattered, Sarah that he would elaborate more upon arrival, but wanted to assure Sarah's undivided availability for few hours for some tours of the island homes on Saturday afternoon. Sarah, of course, had eagerly agreed to clean her schedule and accommodate any of John's needs for the day.

Almost as soon as John had hung up the phone to Sarah Olson, John looked up to se the source of the knock on his office door. it was Madeline, his trusted and loyal assistant. "Excuse me, Mr. Davis," Madeline softly said. Maddie only called John by his last name as a sign of respect when there was a customer or vendor waiting for John. John never made appointments with vendors on Fridays, so he correctly assumed that a customer wanted to talk with him, probably with some complaint, it came with the territory as the boss. "Mrs. Olson would like to talk to you."

John felt a tinge of anxiety as he straightened his tie and walked to door to greet his unexpected visitor. He peered outside of the entranceway to see Charlotte sitting in one of the lounge chairs in the waiting area. She had her golden-blonde-tinted hair pulled back into a tight ponytail, making her appear much younger than her forty-eight years of age. She wore a V-necked maroon sweater that was cut extravagantly low for a Friday afternoon shopping excursion, revealing a set of magnificently and lightly-freckled tits. her legs were crossed over her designer jeans, and she had on a pair of open-toed stiletto sandal that illustrated ten toenails painted a bright red, a shade that perfectly matched the lipstick adorned on her lips, which brightened in a smile at the store managers' appearance. On the floor beside her chair was a large green shopping bag, with the green and gold colors and logo of John's department store on the bag.

"Mrs. Olson, what can I do for you today?" John graciously his hand in welcome.

Charlotte bent dramatically over the arm of the chair, facing John, purposely having the dual effect of both revealing almost all of her perfectly shaped tits spilling out of her sweater, but also putting her face at waist-level, no more than a foot from John's belt. She lingered in that position for a few seconds, feigning as if she were fumbling for something within the shopping bag, her eyes boring directly into John's crotch.

She finally stood up, pulling on the bottom of her sweater as she rose, which had pulled upwards to display her tan stomach and a belly button adorned with a large, gleaming diamond stud. John couldn't help but to glance down and notice the pronounced camel toe that was on display between the legs of impossibly tight, designer jeans that Charlotte wore. Madeline watched intently with matronly disapproval of Charlotte's rather blatant display of public exhibitionism, disgusted that a woman approaching fifty would go out in public dressed in that fashion. Meanwhile, one of the young college kids who worked part-time in the credit department down the hall banged loudly into the doorframe of the employee lounge, his gaze and thus his path distracted fully by Charlotte's sweet ass hugged by the skin-tight denim.

She extended her hand, finger pointing upward, in a condescending manner that would shame Marie Antoinette, the way that rich women who fell into money have of letting the other person know that they are simply TOO important to demean themselves with a conventional handshake.

"Why, hello, Mr. Davis, I hope I'm not disturbing you," Charlotte said, neither waiting for nor expecting a reply. She looked at John with her sky-blue eyes that had undoubtedly been the object of desire of thousands of would-be suitors, yet behind those eyes was a conniving mind that had wrecked a few careers and lives. "I was hoping to convince you to commit to my charity event at my house on Sunday evening. Might I have a few moments of your precious time? In private?"

Again, without waiting for his answer, Charlotte sashayed her way into John's office and seated herself at the one of the same chairs at his conference table where John had watched Maggie insert a shoe heel into her cunt just mere days ago. John shrugged over his shoulder back at Madeline, who playfully brushed her raised palm over her nose in an unspoken 'isn't she the snootiest bitch' gesture. John smiled as he closed the door, and noticed Charlotte was already reaching into her shopping bag even before the door clicked shut.

Charlotte emerged with a tube of lipstick and a tube of body lotion as she loosened her ponytail, causing her long blonde silky hair to cascade freely down her shoulders and onto her cleavage. She started to apply the lipstick while staring directly at John, puckering her full ruby lips and softly, seductively running the tube across them. "I purchased a few things from your cosmetics department, and wanted to try them out. Perhaps you could assist me?"

John fidgeted uncomfortably in front of her, still standing, shuffling his feet from side to side, unwittingly mimicking the inebriated dance of a fan at a crowded football game at halftime, waiting desperately outside of a long line at the port-a-john. "I thought we were here to discuss your, um , event on Sunday, Mrs. Olson?"

"Please, John, let's not be so formal, shall we? Call me Charlotte, I insist." Charlotte snapped the small vial of lipstick shut and dropped it back into her purse. She then fumbled at an attempt to open the jar of body lotion, acting as if the jar was too tight for her to successfully complete the adventure. "Oooh, my, my. I think I need a big, strong man to help me with this." She reached out to hand the jar to him, still impaling him visually with those seductive blue orbs, her eyes running up and down the length of John's tailored suit and crisply starched white shirt.

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