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Online lit meeting leads to sex challenges.
1.3k words
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Part 1 of the 2 part series

Updated 06/10/2023
Created 10/02/2020
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Instruction, Experience, Evolution, Control

Preface

This first installment is a real slow burn without any real sexual narration. Having said this, it is absolutely critical should you be intrigued to follow and possibly play along!

It began gradually over a series of conversations over a period of several months. Grant was a married man soon approaching fifty years of age. Though basically settled down and married for the last ten years, his life had been one of complete sexual exploration albeit with some limits. To say that Grant had limits was very much true but even still, Grant's self-imposed boundaries had eventually settled far beyond the territory of what the average sexually healthy individual might consider as 'normal'.

The much younger Belinda had just celebrated her thirty-fourth birthday along with the finalization of her divorce. This unfortunate result had come from the realization that the man whom she had married was not to be the lifelong partner she originally believed him to be. It was nothing dramatically specific that had brought the union to an end but rather the mutual realization that any spark or excitement that had once kept the marriage fresh had long since been extinguished.

Belinda initially felt as though her sexual resume was fairly well-rounded and typical at least by the comparisons she had considered among her closest friends. But as the aforementioned discussions began between her and Grant it quickly became obvious that there was a great deal she had yet to experience. The friendship between them had developed slowly and built upon a foundation of comfort and trust that had allowed their topics of conversation to venture into areas normally reserved to closer, more intimate relationships.

To say that their relationship hadn't become intimate would be clearly wrong. But it was not intimate in the sense of love or physical connection. Grant was happily married and though he would never stray emotionally or otherwise, his wife supported his keen interest in writing erotic tales and the thrill that came with bringing sexual excitement to others with mere words. This happened to be how Grant and Belinda came to know each other.

Belinda had never been an avid reader of erotic literature and had she not happened to stumble across a tale entitled, 'Crowd Surfing' on Literotica there would be no story to tell. She had not actively searched for porn or erotica it had just come up as a link to one of the articles found one boring night of surfing the web. As for any particular story or author, it was nothing more than random chance that had led her to read one of Grant's stories.

Belinda was surprised at her own enjoyment of the erotic story. It was not her usual thing to read this type of stuff and the subject matter though tame by Grant's perspective, was really not about anything that had ever entered her usual fantasies. But that one short story had led her down the rabbit hole of searching for others and finally to read all that Grant had published online.

Grant loved to write the stories for others and often pleasured himself with thoughts of all the orgasms he was helping to bring to the many unknown readers that stumbled across them. It was ever encouraging to receive the feedback, compliments and suggestions with new subject matter he hadn't considered writing about.

Belinda's message had been simple but intriguing: 'Your's is the first work of erotic literature that I have read and I must say, it was very enjoyable. It made me realize that it is time for me to expand my own fantasy boundaries even if not in actuality. Thank you very much.'

Grant couldn't put his finger on why this one comment of many he received stood out in his mind but for whatever reason he had been thinking of it constantly for several days. Finally, he decided that it might be exciting to learn more of this reader and see just where these boundaries were and more of far more intrigue, where they might move to.

It quickly became obvious to Grant that his new penpal had led a fairly mundane sexual existence. She had lost her virginity in the last week of highschool shortly after her 18th birthday. University found her a number of short and medium term relationships before dating the man that she would eventually marry following graduation. Aside from one drunken hookup with a guy she met at a bar that came on the heels of a breakup with her loser boyfriend that had cheated on her, there was really nothing else of interest to share.

As the trust between them developed Belinda also shared that she had become a fairly practised masturbator over the years but of late, as her romantic existence had devolved, so had her interest in even self-pleasure. Even with this disclosure Grant came to conclude that Belinda's own experience had been so limited that even in the security of her own private moments, the fantasy material she relied on for self-gratification was tame bordering on boring.

Grant quickly became excited with the idea of helping another to experience the sexual liberation he had come to know and live by. At first, he just wrote a few stories with Belinda in mind and with her name within the story as the main character. Eventually, he had persuaded her to provide an idea of something that was way beyond her limits but that she thought would be exciting. This is the motivation that had caused Gordon to imagine the story, 'Jailhouse Rockin'.

As Belinda's comfort level expanded and their discussions focused more directly on how she might further explore more of her own sexuality, a plan began to develop in Gordon's mind. It took a fair degree of gentle prodding but eventually Belinda agreed to his proposal and that she would do her best to live up to the expectations of 'The Challenge'.

Together, they had decided to refer to it as 'The Challenge' but in truth is was really a long series of ever increasing suggestions or more honestly, demands that were solely decided by Gordon. By design, the successful achievement of each series of challenges would broaden Belinda's comfort zone and though all were at Gordon's direction, none could be experienced without Belinda's choice of whether to submit which really meant that the entire experience would be of her own choosing. Essentially, Gordon would provide the roadmap but it was up to Belinda to decide how far she would travel.

Belinda admitted to a measure of unease at agreeing to submit so completely. She hoped that her new sexual mentor would be sensitive to her current level of experience and not make demands that were beyond her tolerances. She considered just how crazy it was to be jumping into this with someone she had never met in person. In fact, she had never even seen a picture of him. To keep some healthy boundaries they had mutually agreed that they would not speak on the phone or on camera. Their online relationship would remain just that and they had agreed that no personal details -- aside from sex which had become the whole point of the text exchanges -- would remain private.

It was a project designed specifically for Belinda however as Grant became more intrigued with where it all might lead he came to realize that his suggestions to her and the tasks that would be required might be equally exciting to any other female reader with an interest in further exploring their own sexuality. And so it was decided that as opposed to emailing Belinda directly, her instructions would be posted on Literotica for she and all others to enjoy.

This series of challenges will soon be posted as a continued telling of this story in the weeks to come. If you choose to participate please feel free to tell me of your progress and level of enjoyment.

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