The Seduction of Jonathan

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Status: In Progress  |  Genre: Mature Sex  |  House: Booksiesilk Classic Group

Young Jonathan, who rents a cottage on an estate has a fantasy of dating the older woman who lives in the main house. He watches her undress most nights from a telescope in the cottage. Dianna, the owner of the house and cottage, is the local librarian. Yet she has a dark side to her, one that as a widow and divorcee, she loves her men younger. She refers to them as "her boys". Through her seductive ways, her telepathy and hypnotic powers, she will turn her tenants world upside down making him her lover and much much more. She brings him to a world beyond his wildest dreams and imagination.

chapter 1


Young Jonathan lived in a small community and had his first place since returning from the state college.  He lived in a cottage on a small estate.  He worked at a local lumber supply and attended the community college part time.  His landlord was a widow who worked as a librarian in the town library. In his eyes, she was gorgeous, Goddess like. 
Many a night he found himself fanticizing about being seduced by this woman who would turn out to be twice his age of 24 yet he thought she was probably in her 30';s.  The cottage had a telescope in it and he couldn't help but look through it and point it at the main house now and then.  While Dianna the widow librarian dressed prim and proper like something out of a 1940's movie when she left for work and returned each day, in the house it was though she was a different person.
The first thing she did after closing the door behind her was to undo her blouse and remove her bra.  She rarely buttoned the blouse back up and sometimes she just took that off and moved about the house topless.  Jonathan drooled at he body her looks, everything about her was perfect he thought.  He never saw men come in or out of the main house and on some occasions, he could see her undress and dress with the shade not drawn when she was in her bedroom. Then she would to on her bed and he could see her topless and sometimes touching her breasts, sometimes with her eyes open, often with them closed. The base board of her bed was too high for him to see through the telescope if she was self indulging, but he imagined she was, and wished he could see up close, he wished she would seduce him.
He tried to get up enough nerve to let her know he was interested in her, offering to help her carry in her groceries and do other odd jobs if she needed.  She took his help and always thanked him but he was stuck hoping she would make the first move but she never did.  He wanted to but then he thought what if she is offended and decides that she doesn't want me to live in the cottage any more, he would be forced to move back home with his parents  and he certainly didn't want that.
What Jonathan did not realize was he was the forth young man to occupy the cottage on the estate.  Each of the other tenants were young men like him, and each would become Dianna's lover over time and move in with her to the main house.When he had down time he found his way to the local library and read there using the time to watch her from a distance.  A couple of occasions she approached him and complimented him for being so studious, and took notice and said she liked what he was wearing.  A couple of times she came over to see what he was reading and bent down close enough that he could smell her intoxicating perfume.
She knew perfectly well why he was there and she was flattered that he was interested.  Yet, she was careful not to let the public around her witness that she had a thing for younger men so her actions were guarded and tasteful.  Still her command of vocabulary enabled her to pepper Jonathan with double entendres that he would recite over and over again trying to dissect if she meant it one way or if it was somehow her way of coming on to him.  Such recitations always happened in the cottage and were usually followed with some masturbatory endeavors on his part.
As he departed on Thursday afternoon, she caught his eye and said
"Going home early today Jonathan?"
"Yes, I thought it being a good day I would get a jump on moving the lawn and stuff."
As he left, she thought to herself
'Well if I time it right I will get home just as he is finishing up and i can invite him in for a cold drink.  Then I will ask him to stay for dinner, then I will make my move.'
Dianna's last lover had been a young man named Tony which Dianna always said his name was Toni with an I.  Toni was not as inwardly or outwardly masculine as Jonathan which made it easy for Dianna to mesmerize him and reel him in and mold him to be the kind of lover she desired.  Dianna was like two different people.  The meek librarian she showed to the public was one version and the woman at home was a powerful, control oriented, free spirited hedonistic woman who enjoyed the company and lovemaking of both men and women alike.  A widow and divorcee, she reached a stage in her life more than a decade earlier that she would not be hurt by men again and decided to invest in younger men whom she could mold and control to her whims and desires.
Dianna had a group of women that she associated with in the privacy of her other realm.  Lauren was her best friend who had been married several times and like Dianna, had a sexual appetite that was unquenchable.  Generations earlier they would have been referred to as nymphomaniacs. In more modern times some might cast them as sex addicts, they preferred the term Hedonistic.  They would go on those cruises for Swingers where people competed to see how many different partners they could bed before the cruise ended. 
Another woman in the group was called Suzie the Fluzie, who distinguished herself as someone who was a bbw big beautiful woman with massive breasts who like Dianna and Lauren was bisexual.  She was into fisting and enjoyed having a man or a woman push their fist and arm all the way to the elbow in both her pussy and ass as a means of getting her off.  Two others who made up the group were referred to as "the twins".  There was no blood relationship, yet they looked very similar in size and appearance.  They were Julie and April.  That their looks was similar came about because they both slept with the same plastic surgeon.Another common point was that they were both born with male genitilia, despite inwardly being women trying to live with discrepancy.
Julie had as yet had all of her male parts removed, but everything else was pure female. She often bragged she had the best tits money could buy.  April on the other hand was post operative, and yet in each case, the two women had small hands, small feet, and the surgeon had fixed all the other parts to make them present as the women they were meant to be.  Julie would share with the other girls about her experiences with men who either she picked up or  picked her up that didn't know she was gender fluid until they pulled down the panties and the stories were funny to contentious.
One of the rules of the group was when they got together for Ladies weekends, they were free to bring a date, but they had to appear and act like women.  That is where Toni, Dianna's last lover excelled initially.  Lauren worked at a local mall in the make up counter and ran a side line of helping cross dressers express their inner feminine beauty.  She did Toni's make up for one of their gatherings and he became so good at it he would often do Dianna's make up for her before the two went out to party, dance, and prowl.
The beginning of the end for Toni and Dianna came when Toni said he wanted to grow a set of his own tits.  His nipples were extra sensitive and he loved having them touched, teased, sucked and bitten.  He had them pierced first and would often use clamps and toys on them as part of their play. He was devoutly submissive and it did not take much in terms of training or reprogramming by Dianna to render him as her very docile live in male whore, slut and lover.Much of Toni's closet and dresser were filled with women's clothing and he wore panties and occasionally nylons beneath his male clothes to work.
Lauren told Dianna if he wanted tits of his own to buy him a set as opposed to going on estrogen.  Dianna let him attempt to grow them herself by taking estrogen and birth control pills.  The breasts began to swell up but not to the level he/she desired so Dianna bought him a set that the "twin's surgeon installed, and Toni finally felt like the woman he thought he was supposed to be all is life.  What Dianna didn't know was that in Toni's new feminine persona, her desire for intimacy had veered very much in the direction of men. 
One of Dianna's rules was they could be intimate with other people so long as it had Dianna's approval first, and the other person could present evidence that they were "clean" meaning they did not pose a risk for STD's.  Toni proved to be a good house boy for Dianna.  He drew her bathwater, bathed her, shampooed her hair, would give her awesome oil massages from her temples to her toes and he was adept at manicures and pedicures for his Mistress Dianna.  He cooked, he cleaned, he did anything the house maid didn't have time to do.  He would lay out Dianna's clothes the night before, would dress  her in the morning and undress her at night when she got home and have a drink waiting for her.
His sexual performance was good at first but diminished when he became more female.  Dianna was ok having what she termed a lesbian relationship with Toni whom she on occasion referred as Antonette. They had fun shopping together and would often pick up Lauren and the three of them would engage in people watching.  For Lauren and later for the couple, they were really sizing up people they wanted to invite as lovers.  If Dianna saw a hunky man or a bull she wanted, she didn't hesitate to pursue him, but she would make arrangements for Antonette to be occupied with companionship and get laid that night and then the two would share their stories when the dates ended.
More and more Toni wanted to suck the bull off or do a threesome with Diannawhich happened only once.  Toni wanted to be gang banged and Dianna after some hesitation agreed and set up a private party at a sex club they frequented.  The deal was, all parties had to have a card indicating that they were safe.  All Toni had to do is keep to the safe people and it would have worked, but he couldn't do that and had sex with multiple men that had not cards to show they were safe. Dianna was furious and banished him first to a guest room in the main house then back to the cottage before breaking it off with him and setting  him up with a couple who were both bi and wanted their own houseboy,
Jonathan would be Dianna's first new lover since Toni, so she was cautious about how she would come on to him, and what she would do mesmerize him and take him under her wings.  At the same time, Dianna was just as insatiably horny and Jonathan looked like a good mark. She knew he looked at her through the telescope, as did the three young men who lived there before he did.  It was after all,her telescope. 
She presumed he self indulged after watching her tirelessly nigh after night, month after month.On her ride home from the library she heard the Rod Stewert song on the radio "Tonight's the Night". and she knew what she would do.
Jonathan was just finishing up the yard work she pulled into the driveway. 
With sweat dripping off his body, He was happy to Dianna, and secretly hoped there would be some interaction that would break the ice. 
"Place looks good as always, you do such a great job, but you must come in and let me pour you some lemonade or ice tea."
Jonathan might have declined thinking she was just being polite but he surprised himself when he said
"I would like that very much."

Submitted: April 10, 2023

© Copyright 2023 j.d. davis757. All rights reserved.

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Add Your Comments:



Josh, have you looked at how to create a book on this site? The reason I ask, you basically have three chapters of a book here. I would recommend a book as opposed to serial short stories on the same topic. Easier to follow.

I would love to see more dialogue and less narrative. You have covered a ton of ground through narration just in one chapter alone. If you elaborated this short story, you could probably get five chapters out of it.

It's a fascinating situation, an older yet sexually alluring woman who somehow possess a rather large estate entices young men to rent on her property and incidentally provides them with a telescope in their rental, then parades around her mansion in the nude with the windows open! What an idea!

We do get misdirected a bit with this Toni (Tony) story, followed by all these vast numbers of sluts and trainees who get together for orgies. If you want to discuss Tony, why not start the story with him living in the guest house. Let's get through all that wild and wooly adventure first, then we will pick up Jonathin on the backside.

What I want to see you do is get into the details of day-to-day life with these characters as opposed to giving me a history lesson that is much more peripheral and much less enticing than an actual sex scene. Take off your wide-angle lenses and put this under a microscope. Give me conversation. Give me the moment-by-moment account of Jonathan's interactions. Make me live inside your creation.

Tue, April 11th, 2023 4:27am


The issue of Tony in the story is a bit distracting for me, although the whole idea of an older woman seducing and controlling younger men is appealing.

Wed, April 12th, 2023 2:02pm

j.d. davis757

Wonderful and insightful feedback. Appreciate your views and perspectives. Needs major rewrite and I think the book idea is worth pursuing, thank you, you are most kind and thoughtful

Fri, April 14th, 2023 4:59pm

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