Because, Why Not?
Caution: This Sex Story contains strong sexual content, including Consensual, BiSexual, Heterosexual,
Desc: Sex Story: Chapter 1 - Dramatis personae: Sydney ... unmarried, bisexual, 32-year old mother. Megan ... Sydney's aide / confidante. Jackson ... Sydney's 14-year old son. Additional casting ... TBA. Drama: A voyeur's delight - - a free-spirited mother who thinks progressive education, her version of home schooling, includes ... whatever. A precocious son who, despite and because of his unconventional mother, was turning out well. The setting: Penthouse floor, Capital Hotel, Little Rock.
Sydney Worthmore might have been a better fit had she lived in San Francisco in the 60s rather than Arkansas in 2015. But Sydney Worthmore didn't give a fuck about being a better fit. Nor a worse fit, nor any fit.
Sidney didn't march to her own drummer, she conducted her own orchestra.
Sydney, born to Texas money and Connecticut money, bought the top floor of the posh Capitol Hotel in Little Rock. The hotel is in the River Market area, down by the Arkansas River and not far from the Clinton Presidential Center. The top floor wasn't for sale, nor was any other floor. Sydney bought it anyway.
Sydney's closest friend and confidant was 77-year old Taylor Hutchins. Hutch was a professor emeritus, retired from a vaunted philosophy career at Yale. He was a lifelong celibate. By choice.
Sydney had been tempted, briefly, to marry her primary lover, Emma. But Sydney knew herself, knew it wouldn't work for very long. She didn't like commitment, the feeling of being tied down. Not that she minded being tied up once in a while.
Sydney's son, Jackson, had never seen the inside of a classroom. As she told Hutch, "Fuck a bunch of public schooling. Not for my Jacks."
By the time Jacks turned 8, Sydney stopped hiring tutors for her son. They were unneeded and unwanted. To keep the so-called authorities off her back, she had her assistant -- her loyal and discrete assistant -- 55-year old Megan Meacham drive Jacks over to the school district office to take whatever dreary exams they insisted upon.
Because Sydney traveled extensively, and moved in with a series of lovers -- men and women -- for extended periods, Jacks grew up sort of like the male version of Eloise. Except in the Capital Hotel rather than the Plaza. And Little Rock rather than New York.
Sydney kept her Greenwich Village townhouse, but spent more time in Arkansas, a choice that puzzled her East Coast circle. The consensus was a shrug and the often-voiced, "That's just Sydney."
Sydney had chosen Little Rock partly because Hutch retired there. And partly because Emma was from there and talked about it all the time. And partly ... because, why not?
Both Sydney and Jacks had vivid, lustrous, red hair, fair skin, no freckles, and slender bodies. They carefully trimmed each other's pubic hair when Sidney was in town. Sydney formed Jacks's into a triangle that pointed down to his generous cock.
The waxing process was surprisingly painless, almost gentle. Megan found some wax that was honey-based in Singapore. There was the slighted tugging sensation as pubic hairs were pulled out, but that was it.
These days, Sydney wore her vivid red pubes in the shape of a tiny heart. She showed it to Hutch, "Such a fucking cliche, but I still like how it looks."
"Very sexy, I love it, Sydney."
Sydney had an amazing smile. It was like the sun coming up. Jacks's was a slightly milder version, but still magnificent.
Sydney's assistant, Megan, traveled with her everywhere. When Sydney took up residence with a lover, Megan moved in also. Not only was Megan discrete, she was unflappable. She had been hired by Sydney's mother right out of Miss Porter's School.
When Sydney was born, rather a surprise pregnancy, the baby was turned over to Megan. Megan served as mother, nanny, tutor, confidant, co-conspirator against Sydney's parents, assistant, and most importantly, friend.
Sidney didn't have a fuck-you attitude toward the world, she just didn't much care what other people thought. If she wanted a woman to lick her pussy, or wanted a couple of young studs to double-fuck her, Sydney didn't give a rat's ass who saw her doing it.
Jacks was smart enough to have figured out early on that it wasn't conventional to watch your own mother having sex. As he grew older, he went from casually interested to curious. With some considerable excitement thrown in. As always he talked openly with Megan.
She didn't try to explain Sydney to him, certainly didn't try to justify his mother's behavior. She simply told Jacks, "Sydney goes her own way."
The first time Jacks spurted off while his mother was trimming him, Sydney told Megan, "Teach him about sex. Or contract with a couple of whores."
Megan didn't blink. She immediately started undressing. Jacks had seen Megan, his best buddy, naked dozens of times. Tall, dark-haired, quick to smile, Megan was usually 10 to 15 pounds overweight, much of which seemed to be in her bosom.
She took Jacks over to her suite on the west side of the penthouse to 'teach him about sex.' Over the course of the next several weeks, she taught him everything she knew, which was considerable.
Sydney watched Jax and Megan a few times, but didn't seem that interested.
It wasn't that Sydney was indifferent to her son, although Megan had a lot more to do with his upbringing that she had. It was just that Sydney believed her son should be independent, make his own decisions, his own choices, his own mistakes.
By the time Jacks turned 8, neither Sydney nor Megan had the slightest qualms about leaving him to live alone for weeks at a time. He had room service, daily maid service, the run of the hotel's restaurants. Jacks knew every staff member by name and was unfailing courteous to each and every one. Megan had seen to that.
Jacks also knew many of the residents and merchants in the River Market. Neither his mother nor Megan had told him to be wary of strangers. Nor careful crossing streets. It wouldn't have occurred to them; they expected Jacks to make wise decisions.
When Megan was satisfied with Jacks's sexual education, she kissed him one last time and said, "You're on your own, honey. Find your own pussy from now on."
"Thank you, Megan."
When traveling with Sydney, whether around the world or downstairs in someone else's hotel room for a week, Megan e-mailed or talked to Jacks every day, without fail. Sydney talked with him once in a while, always pleased to hear her son's voice.
After Megan, his mother's primary lover, Emma, was Jacks's closest friend. Emma loved teasing him. She often finished licking Sydney and went over to Jacks, kissing him deeply. Jacks was the only person she kissed other than Sydney.
Emma would whisper, "Taste your mama's pussy, Jacks."
Jacks would taste. And taste.
Emma was 34, a couple of years older than Sydney. She looked very prim. She wasn't. Dark hair, slender like Sydney but with bigger boobs. Jacks adored her and used to wish her mother would marry Emma. As he grew older, he understood it wouldn't work, not with Sydney being Sydney.
At home, and the hotel had always felt like home to Jacks, there was no dress code. Sydney wore whatever she felt like or nothing at all. Some days she wore underwear, others only panties. Some days only a bra, although she didn't need one and rarely bothered.
Jacks had received no instructions, no guidelines, no hints from his mother and Megan. Like most things in his life, it was up to him to decide. So far as he could tell, neither Sydney nor Megan cared what he wore. Or if he wore anything.
The daily maid service soon grew used to seeing Sydney, or Jacks, or both, in the nude. Jacks might be erect or not. The maids weren't as unflappable as Megan, no one was, but they were well trained by the hotel and well compensated by Megan.
The same casualness applied to masturbation. Once he started spurting off, neither his mother nor Megan said a word about when and where he should do it. The only stipulation came from Megan, "Clean up after yourself, honey."
His mother, or Megan, or both of them, might pause to watch him cum. Or they might not, depending on their day. Jacks liked it when someone watched, especially his mother. Because, why not?
One day in particular was etched into Jacks's brain. His mother was giving him his weekly pubic touch-up and he grew erect as he usually did. Sydney ran a fingertip up and then back down his 8 thick inches and said to Megan, "I may fuck him one of these days."
Megan shrugged, "Up to you, Sydney." Unflappable.
His mother hefted his large balls as if weighing them and said, "I just may."
Jacks not only remembered those words, he knew his mother meant it.
When Sydney and Megan moved in with one of Sydney's lovers for an extended spell, Emma usually came to stay with Jacks. Even though she never got used to Sydney's promiscuity, she never stopped loving her. Couldn't.
Emma slept in Jack's bed, snuggling up, the two of them nude.
Unlike his mother and Megan, Emma encouraged Jacks to masturbate several times a day. While she didn't touch him sexually, she insisted he jack off in her hands. She told him, "I just love the taste of your cum."
One time Sydney had strolled in and said to Emma, "Give me a taste."
Emma offered her hand. Sydney held Emma's wrist and licked her palm clean, looking at her son as she did. Sydney said, "Hmm," and gave Jacks her megawatt smile, saying, "Emma's right, baby boy, really yummy."
Not often, in fact only three times, Sydney had held out her own hands, a la Emma, and licked up her son's cum. Each time she flashed him her marvelous smile.