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SPANKING REGGIE'S STEPMOTHER

by Jack Crawford


1. Reading of the Will

Reginald Ovington Idlewine, Junior, sat quietly thinking in the attorney's office. It was a formality, really, as Reggie knew the contents of the Will that was being read, if not the specifics. Barely 18 years old, Reggie had just become one of the wealthiest persons in America, if not the world, with his inheritance of an estate valued in double digits of billions of dollars. It was a forgone conclusion the moment he'd heard his father had plummeted to his death in a climbing accident in the Andes Mountains.

The sudden wealth did not occupy his thoughts; Reggie had grown up (as much as an 18-year-old can grow up) in extreme wealth. His great-grandfather had amassed a fortune and his grandfather and father had only made the wealth more staggering. Interestingly, each generation had sired only a single son which left Reggie the sole heir to the massive wealth. His great-grandfather had had the vision to convert his inheritance to a family trust and his grandfather was the first in the family to use an unusual pre-nuptial agreement to stave off gold diggers who wanted him only for his wealth.

Reggie's father followed Reggie's grandfather's example and utilized the unusual 'pre-nup' not once, but twice. Reggie's mother had died when he was just six years old and Reggie had directly inherited her (comparatively) small estate (though it was administered by a trustee, the same attorney who was droning on this very minute, until a couple of months ago when Reggie turned 18.) The pre-nup was used again when Reggie's father remarried when Reggie was 12.

And it was his stepmother, the only other person in the attorney's office with him that occupied Reggie's thoughts. Syndee (Reggie always wondered at that spelling) had been 22 when she'd married his father and that made her just 28 years old now. He had disliked Syndee from the moment that he'd met her, and had grown to hate her with a passion. Reggie thought about the pre-nup and realized that the object of his hatred was about to disappear.

The combination of pre-nup and family trust effectively excluded his hated step-mother from sharing in the wealth. Essentially, the trust excluded all but direct blood descendants which, in this case, was only Reggie. Add to that the unusual feature of the pre-nup and Syndee was effectively frozen out. She had signed the pre-nuptial agreement and taken the $5 million pay-out on the day of her wedding. For all intents and purposes, Syndee got her part of the estate 6 years ago. I hope she didn't piss it all away, thought Reggie as he mused about the situation, realizing that, the bitch probably doesn't have a dime left, the way she went through money.

It wasn't his problem, but that thought did cause him to smile. Oh, how Reggie hated his stepmother! From the very first day that she'd moved into the sprawling mansion, Reggie had disliked her. But, insisting that Reggie call her 'Mother' sealed her status in Reggie's eyes. He reluctantly called her 'Mother' ... never 'Mom', 'Mum' or 'Mommy'. It was always a long, drawn out pronunciation of 'Mother' that he would utter with a heavy emphasis on the last syllable.

The spankings had started the first time he had sulkily said, "MothER." She thought he was being disrespectful (of course he was!) and the child needed to learn his place. The first time she simply bent him over her knee and gave him a few whacks over his pants with her hand, but the spankings eventually became full-fledged hairbrush spankings on his bare bottom. His last one was four months ago when he was 17. Seventeen! Reggie couldn't imagine any of his friends of his own age being spanked, but he'd had to endure it.

When Reggie had complained to his father about the spankings (which he did frequently) his father had answered, "She's your mother now." Then he would add, "I don't think she doles out a spanking unless you've earned it, so learn from your mistake. In any event, it builds character." And then the matter was closed until the next spanking.

And there always was a next spanking. Syndee seemed to go out of her way to find excuses to bare Reggie's bottom and tan it. In all likelihood, Syndee probably disliked Reggie just as much as he hated her. Oh, well, thought Reggie as the attorney continued to read, she'll be out of the house quickly and won't have anyone else to humiliate.


It was as much of a burden for Syndee to sit through the reading of the Will as it was for Reggie. She knew her situation and could only hope for some additional crumbs to be thrown her way, but her husband had diligently followed in his father's footsteps and she was left only with what remained of her $5 million pay-out from the prenuptial agreement.

And what was left was only a few hundred thousand dollars. The rest had all been squandered on 'things'. She could sell some of her jewelry, but she'd never get back what she had paid for it, and the clothing she had (there were rooms in the mansion converted to closets just for her clothes) could not be sold. In many cases the clothing could not be worn again because it was no longer this season's fashion.

In short, Syndee was not destitute, but she was no longer filthy, stinking, rich. As the Will was being read, she pondered her situation. She didn't own a car of her own and would have to spend her money on a place to live ... but what could she afford and how could she maintain it with what she had? She had no marketable skills and it had been six years since she had been swept off the stage at the upscale 'Gentleman's Club' where she had been dancing by the wealthiest man she would ever know. Syndee still had her 'stripper's body' and could command the attention of any man with just her appearance, but finding a suitable replacement husband would take time.

Finally, the reading was finished and Syndee and Reggie thanked the attorney for his time and trouble and accepted his condolences for their loss. They then drove back to the mansion in the separate cars they had taken to the attorney's office.


It did not take long for Syndee to corner Reggie in the sprawling mansion. She shed a few pitiful tears of loss over her husband's death, but it was difficult for her to put up the front for very long. The funeral had been a week earlier and Syndee had cried herself out at every opportunity as she had tried to ply Reggie for sympathy. The tactic hadn't worked earlier and it wasn't working now as the two protagonists sat opposite each other in the massive (and hugely impressive) library in the mansion.

Ever the cunning tactician, Syndee quickly summed up the situation and decided that Reggie would not be manipulated with her tears and, as her stepson, she thought it would be too risky to attempt to flirt with him. Reggie might be a horny 18-year old, but there was too much history between the two of them for her to successfully manipulate the young man with sex.

The only possible avenue of attack at this point, Syndee reasoned, was the truth. So, with a final dab of a hanky at the corner of her eyes, she steeled herself for the inevitable derision her situation was about to incur. She had no choice; honesty was now the only policy!

It was probably the most honest five minutes Syndee and Reggie had spent with each other over the past year or two. Reggie showed considerable restraint as he listened impassively to Syndee's detailed and nearly clinical explanation of her financial situation and the relative 'hardship' a sudden change would engender. Syndee was equally restrained in her description, choosing not to embellish her situation with any emotionally charged descriptions. When she'd finished, Reggie thoughtfully considered what his erstwhile stepmother had said, seemingly searching her for clues with his eyes as he sat motionless. His elbows rested on the arms of his chair, hands raised with steepled fingers over which he contemplated Syndee's request to remain in the mansion.

And then Reggie replied to her request with a maturity beyond his years. "I know my father loved you very much," he said in a measured voice, "and it would disturb him greatly if I just tossed you out. You need time to grieve, perhaps," he added. Watching her closely he actually believed the only grieving she would experience would be the grief for her new circumstances. But, Reggie continued, "And you'll need time to situate yourself and maybe find a new man for yourself." He smiled almost knowingly and it unnerved Syndee just a bit.

Syndee waited patiently ... hopefully ... as Reggie continued. "There certainly is enough room for us both in this house," he said with a broad smile. A smile reciprocated by his, as he was beginning to think of her, former stepmother, encouraged him to continue. "So, I see no reason why you shouldn't continue living here for the foreseeable future." You could see the relief in Syndee's face and hear the sigh of her previously held breath. Just as she was about to express her very real gratitude, Reggie continued.

"We just need to set some ground rules," he noted with suddenly cold calculating eyes that unnerved the young woman. "First," he said, holding up his index finger, "you may continue using anything you've had access to in the past. Stay in the master bedroom, use any of the cars, whatever. But, you will get permission to spend any money in advance. I won't be unreasonable and I'll have to think about establishing something like an allowance if that would make it easier. I'll think about that, but for now ... you need my OK in advance."

Syndee nodded her agreement.

"Second..." he lifted a second finger, "you may entertain here if you like, but no guest comes upstairs." He smiled a wicked little smile of retribution over that. "It's sort of like my limits were on bringing girls upstairs."

Again, she nodded in agreement, thinking this was going far better than she would have hoped. For his part, Reggie was making all this up on the fly as thoughts popped into his head. At this point, he was rather pleased with himself.

"I guess that's the main stuff," he said, "but it is all subject to revision at any time." And then the thought struck him. "I, by the way, will no longer call you 'Mother'," he told her. The look in his eyes unnerved Syndee as that look had the same quality her late husband exhibited when he was very, very serious. That look brooked no argument. "I'll call you by your name - Syndee," he concluded.

The young woman realized that the power dynamic in the home was officially changed as she, once again, nodded her concurrence. She looked up at him and gave Reggie a weak smile of acceptance along with her nod.

And then the imagination of the 18-year-old reared its ugly head and beat back the rational adult thinking Reggie had just been employing. With a wicked grin he said, "And, Syndee? The spankings are going to change. You are no longer going to spank me ... it will be the other way around: I will spank you."

The look of shock on her face would forever be etched in Reggie's mind, and that shock only deepened when he added, "And I think now is an excellent time to establish that fact!"



© Jack Crawford
Not to be reposted, reproduced or distributed, in part or whole.