To Teach a Boy a Lesson Ch. 01

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Latisha has to deal with another blackmailer.
9.6k words
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Part 1 of the 2 part series

Updated 10/29/2022
Created 06/26/2009
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"Excuse me Latisha," Rosie called as she peered around the office door to see her boss working steadily at her desk.

Latisha looked up, "Yes, Rosie?"

"There's a young man out in reception that would like to see you."

Latisha looked at her watch -- it was close to four-thirty, "Did he have an appointment?" she asked as she checked her Outlook calendar.

"No he didn't. But he said it would only take a few minutes of your time...I think he may just want something witnessed...he has a folder under his arm," Rosie offered casually.

Latisha looked at her young red-headed personal-assistant for a few moments, witnessing documents annoyed her, no money in it directly but it did occasionally lead to a new client and was, after all, just another a part of the game.

Latisha sighed, "Oh, alright then, send him in, thanks Rosie!"

A few moments later, Latisha looked toward the doorway as her impromptu visitor appeared and almost gasped with surprise.

"Oh hello...have you come to talk about cars or something?" Latisha asked, smiling a little more candidly than her professional manner usually allowed.

A tall boy with unruly-looking fair-hair stood nervously in the doorway and stammering slightly, he said hello back to her.

Latisha smiled up at the good-looking lad; it was only the day before that she had almost bumped into him when walking to her car -- her head in her handbag absently looking for her keys -- although he was partly to blame too as he had been sitting on his mountain-bike diagonally across the footpath only a few metres from where she was parked blocking the way.

They had exchanged pleasantries at the time and the lad had asked Latisha about her car, of which he seemed to know a bit about, but of course, what red-blooded boy these days didn't know a bit about cars?

"Come in...come in. What can I do for you then? Are you after some legal advice or something...mmm? Or maybe you have some documents that need witnessing?"

"My name's James...but people call me Jamie."

Latisha stood up from behind her desk as the youth walked into her office, closing the door behind him.

She offered her hand, "I'm Latisha, Jamie, pleased to meet you again."

Shaking his large hand, Latisha looked up at the youth, who now appeared to be trying to act quite nonchalant. He was really quite tall she noticed, probably a bit over six feet -- and quite lean-looking too, but in a healthy, athletic sort of way more than just skinny-looking. His eyes, as Latisha had noticed the day before, were piercingly blue and because of his sun-tanned complexion they stood out noticeably. She guessed him to be around nineteen or so.

"Sooo...are you on the bike again today?" Latisha asked, not knowing what else to say at that moment.

Jamie nodded.

"I'm sorry if I got in your way yesterday, miss..."

"Latisha...call me Latisha, please Jamie."

The boy coughed lightly, clearing his throat, "Latisha...I do apologise...but I just had to be certain it was really you," Jamie said somewhat cryptically, his voice wavering slightly.

"Pardon?" Latisha said, cocking her head to one side, "Had to be certain it was me? Whatever do you mean, Jamie?" Latisha asked curiously, as she sat back down behind her desk and began fidgeting with her pen absently.

Jamie cleared his throat again, "I've gotta say...Latisha...you're even prettier in real-life though."

"In real-life, Jamie, excuse me?" Latisha frowned, starting to get a little annoyed.

Jamie offered Latisha the manila-folder he had been fidgeting with, and smiled at her with growing confidence as she accepted the folder and opened it.

Latisha gasped quite audibly as she looked down at the contents of the folder -- and Jamie knew then, almost for certain, that it just had to be her.

"It's you, isn't it...Latisha, the photos are of you, aren't they?"

Latisha was horrified, "Oh my god-father, whatever has possessed you to come into my office and show me...pornographic photos of...of...well someone who sort of resembles me!"

"Sort of?" Jamie retorted smugly, reaching down to the half-a-dozen coloured photos and selecting one in particular.

Jamie held it up boldly, "Sort of?"

Latisha blushed quite uncontrollably as she looked at the photo. It was, after-all, an almost a full-frontal of, well...of her!

There she was dressed in the little outfit her son-in-law, Duncan, had given her the first time they had 'been together'. There was no doubt in her mind -- Latisha instantly recognised the lovely figure-hugging bodice of red-lace that had at the time struggled to contain her breasts. Then of course there was the very-short black leather mini-skirt barely covering her buttocks and a pair of fish-net stockings, which were only just visible above the beautifully-made thigh-high leather stiletto-heeled boots she wore.

Latisha remembered discovering Duncan had secretly filmed their first time together and the photo the boy now held in front of her was no doubt a frame taken when she had, quite unwittingly, stopped to admire herself in the mirrored-door of his bedroom wardrobe -- just before she had decided 'to teach him a lesson or two', a decision that had changed the path of her rather staid-life considerably from then on!

Although the photo was not of the best quality -- slightly blurry and the pixels a bit large, she could never-the-less, just make out her son-in-law lying on his bed behind her -- dressed in all his finery, his hands trussed to the bed-head waiting for her to join him.

"Sooo...so you think that's me!" Latisha cried, trying to laugh, "Young man, I suggest you get out of here before I call the police!"

The youth stood firm -- smiling at her sardonically, "Here, what about this one then?" he said, holding up another photo.

This time it was a close-up of what was almost undeniably her face - with her tongue poking out as she licked the end of a large, erect penis that she held vertical in her small left hand. Her unique wedding rings were clearly visible.

"Maybe your receptionist would recognise who that is...and maybe she could tell me who it is you're impaling yourself on in this photo, too?" Jamie mused, as he held up another photo, this time of her riding the young man lying beneath her cowgirl-style, her head thrown back in apparent ecstasy, "I'm pretty sure it's not your ol' 'usband, hey?"

Latisha stood there quite dumbfounded -- she just did not know what to say!

Jamie, on the other hand, casually gathered up the photos into the manila-folder and turned for the door.

"Wait!" Latisha called urgently.

The youth stopped and turned to face her again.

"If it was me...and I'm not saying it is, what...what do you want from me?" Latisha asked softly, "Money...is that what you have come here for, money?"

Jamie smiled at her question; funnily enough he wasn't really too sure what he had expected her to do. He had thought it possible that just maybe, just maybe she would not care all that much about the photos -- maybe her husband already knew she screwed around on him -- and maybe he was fine with it too. But her facial expression now told him a different story -- she looked worried, very worried indeed.

He felt his confidence rising.

"Money? Mmm, yep, money would be good."

"Okay, okay...give me the photos...and I'll give you a hundred dollars," Latisha said, "Of course I'm not for a minute admitting they're of me you see...it's...it's just that one of the last things I want is for you to go out there with them and...and shock my young employee with...with pornography," she stammered nervously, "Rosie's a good church girl you see, Jamie."

With her heart pounding in her chest, Latisha fumbled in her bag for her purse. She was completely bewildered as to where the youth would have come into possession of the explicit photos, but one thing that she was certain of -- she did not want them leaving her office! They could ruin not only her legal practice in the small community, but even worse, her marriage and then of course her relationship with her daughter, Amanda, even if Duncan and her had been separated at the time of Latisha's adultery with him.

"A hundred, hey? Still don't reckon it's you? Tell ya what, see this one 'ere?" Jamie said as he held up another photo, "See?"

Sneeringly, Latisha looked up into the boy's eyes briefly and then down at the picture; it was a close-up of a woman bending over a couch with her skirt being pulled up by a man who was standing directly behind her, his clenched buttocks bare -- as are hers. Latisha could see quite clearly that part of the man's large erect penis disappeared between the blonde woman's slightly parted thighs.

"Could be anyone, Jamie, all you can really see are their butts!"

"Right! Why don'cha take a closer look...have a good look at the woman's left hip."

Latisha huffed, and then peered closer at the photo.

"See the tattoo? One of them bluebird thingies that were popular probably twenty years ago...or so I'm told," Jamie went on, "If you can prove ta me you haven't got an identical one on your hip, I'll take ya 'undred...so as not too offend ya receptionist out there as you have already suggested, and I'll never botha you again."

Latisha looked at him ashen faced -- waiting for the rest of it.

"Otherwise...I want two 'undred," Jamie continued, "and they're yours ta keep."

"Two hundred dollars now! Why you young extortionist!" Latisha sneered, "Listen, I'm not in the mood for playing along with your silly juvenile games, Jamie, so you can forget about me proving one way or the other as to whether I have a tattoo on my hip...and besides, even if I did...as you have said...they were pretty popular once!"

Jamie turned for the door again, "So what's ya receptionist's name?"

Latisha waited till he reached for the door handle, "Wait!"

Jamie stopped and looked back over his shoulder at her, "What?"

"You young scammer...two hundred, hey?" Latisha growled, as she opened her purse and quickly counted out four fifties, placing them on her desktop.

Jamie couldn't help but smile as he picked up the cash. How easy was that, he thought to himself?

"The photos please," Latisha said, trying to sound firm as she held out her hand.

Jamie looked back at the attractive middle-aged woman and felt an immense surge of power at what he'd just accomplished -- it was just too easy! She now stood there still blushing nervously with her hand out-stretched -- and he couldn't help but grin at her as he intuitively recognised her vulnerability. And then quite unexpectedly Jamie felt something weird, something primal happening to him -- at first just a tingling in his groin, and then as blood rushed to his penis, he could feel himself growing hard!

"Oh, and there's one more thing before you get the photos," Jamie said as he looked Latisha up and down smugly.

"And...and what may I ask is that?" Latisha snapped infuriatingly.

"Listen, we both know it's you in them photos, don't we? And I reckon you're no more respectable than the next cock-loving whore," Jamie said calmly, "So...I wanna see that tattoo...for real!" he smiled mischievously, "Yep, that's what I want...I wanna see your tattoo for real!"

Latisha felt as though she had been slapped across the face!

"You what? You want to see what? You have got to be kidding! Get out of here you cheeky young prick, before I throw something at you!" Latisha said angrily, tears welling in her eyes.

Jamie smiled cruelly and turned to walk towards the door yet again -- he still had the photos tucked under his arm.

"Stop!" Latisha called; she hesitated for a few moments as the lad turned back around to face her, "Why? I'm...I'm probably older than your mother...why on earth would you want to see a middle-aged woman's tattoo...why?"

Jamie raised one of his eyebrows and shrugged his shoulders, "Could'a said I wanted ta see ya cunt...'cause I've never seen one of them for real before! Well not a nice one...seen me mum's, but that don't count, she's pretty fat an' 'er cunt's all big an' hairy," Jamie answered matter-of-factly, "But you're pretty hot, Latisha, a real MILF I reckon, older...but there's somethin' fucken nasty about ya!"

Latisha had of course heard the term 'MILF' before, but she still couldn't really understand it. According to her former son-in-law, while justifying his own attraction to older women such as herself, he had said that a lot of young men these days wanted to experience an older woman -- and if they were married, well that was even better!

Latisha felt her cheeks blush even more at the boy's crude comments, but she also felt something else...strangely, she felt quite flattered too.

"Who else knows about the photos?" Latisha asked solemnly, stalling for time.

"Jus' me, I guess," Jamie lied.

Actually, a close friend of his named Eddie had given him the photos just a little over a week ago, soon after discovering them on one of their favourite MILF websites. At first the two boys had thought they were photos of a friend's mum they both had the 'hots' for her -- same long, curly blonde hair -- same body too. With a lot of wishful thinking, the pair of them had scrutinised the photos in detail closely for sometime, before quite disappointingly, they had to finally discount Mrs Baker. Ironically it was the tattoo, or more precisely, the lack of. Jamie and Eddie both remembered ogling Mrs Baker once last summer while she had sunbaked in just a small bikini in her backyard --and there was definitely no tattoo of any description that they could recall on either hip.

But still, Jamie was sure he knew the face from somewhere -- that of which he was certain of. It was only when Jamie had seen an advertisement at the local cinemas a few days later that the penny had finally dropped. There on the big screen, was a blonde woman he had seen around the local shops a few times -- a woman named Latisha promoting her small law-firm -- and a perfect match for their photos! What luck!

Latisha looked the youth up and down again and sighed, so young -- in another few years the girls would be clambering to get to him, she thought, as she looked at his ruggedly-handsome young face.

"Just how old are you, Jamie?"

"Just turned nineteen," he lied again; he really had only celebrated his eighteenth a fortnight before but he felt the extra year sounded better.

"Nineteen, hey, Jamie, I'm forty-two!"

"So!" he snarled.

"Surely there are some girls your own age you would rather be with?"

There probably were a couple of girls he knew from school who he could ask out sometime -- and they would probably do that for him -- and more. But there was just something about Latisha, he thought.

He looked at her closely; she had the classic hour-glass figure he noticed; and yes, there was definitely something undeniably attractive about her -- something that had now given him an aching hard-on!

"So...ya gonna show me or what?" he said quite uncouthly, a crooked smile forming at his growing anticipation.

"Give me the photos first," Latisha said, holding out her right hand again.

"Half now, the other half after...after I've seen ya tatt," Jamie bargained instantly, selectively pulling out some photos to hand to her.

Latisha looked at the pro-offered photos; she knew if she was to take them she was more or less agreeing to his terms. My god, what was she considering? She shook her head and sighed deeply again -- then lent forward and almost snatched the photos from him and walked around her desk. Then, without looking at them, she fed them into her document shredder, waiting till they had completely disappeared.

Turning to face her young blackmailer, Latisha looked at him shrewdly -- such an evil mind in one so young.

"Just a look, okay...no touching, or anything, and no blurting it out to anyone...promise?" Latisha said as she stepped around to the front of her desk.

The boy had a grin on him like a Cheshire-cat and of course he readily nodded in agreement.

Latisha's heart was racing -- she could not believe what she was about to do -- but did she really have a choice? She finally consoled herself that it was after-all, no more than what she would normally show when down at her favourite beach to all and sundry.

Slowly, she turned to face the boy, then leaning back against her desk; she looked the boy squarely in the eye and told him to sit down first.

Again he nodded, and pulling up a black-leather and chrome office-chair from near the front of the desk, he sat down -- barely a metre away from her.

She knew she had to buy herself some time -- she was not stupid -- it would've been pretty obvious to anyone that the photos he held of her were more than likely, not the only copies. Even so, she could not afford him to carry out his threat of showing them to Rosie -- or to anyone else!

Latisha knew only too well how a little blackmail could turn into regular extortion and she was under no illusion that whatever the young prick demanded now would not be the end of it! Even so, she had to play along with it -- for the moment anyway, so as she could formalise her own plan.

Jamie looked up at Latisha expectantly; she wore a low-waisted black-polyester pleated-skirt of a respectable length that stopped about mid-thigh. On her feet she wore open-toed shoes with a modest heel of no more than six centimetres. Her white sleeveless-top fitted her snugly and was unbuttoned down low enough so as to show her ample cleavage. A slender gold necklace with a large pearl hung alluringly between the tanned cleft of her breasts, while a chunky gold bracelet of a similar link to the necklace was on one wrist and a gold watch on the other, both complementing the lightly tanned skin of her bare arms nicely.

"You really want to see it, do you?" Latisha stalled.

Jamie pouted his full lips and nodded slowly, "Not a glimpse either, I want a good look!"

Latisha toyed with the hem of her skirt and thought the boy looked more determined than before, if that was at all possible. She sighed again and slowly began to raise her skirt.

"You looked up my skirt yesterday in the car park, didn't you?"

"Might'a," Jamie sniggered; he had hoped to catch a glimpse of her tattoo then for confirmation as she'd sat herself in her car -- and even though her skirt had ridden up her thighs alluringly and he did catch a good glimpse of her panties -- he didn't see any tattoo.

But now the boy watched closely as Latisha's upper thighs slowly came into view.

"You're a sick little puppy, aren't you Jamie?"

"Fuck orf! Me sick? So who was it in them photos, hey? Fuckin' riding some young bloke's fat cock after suckin' him orf...and him all tied up and dressed like a fuckin' woman, who's idea was that, ya sicko?" Jamie retorted, "I reckon you're probably gunna get off doin' this too!"

Latisha could not believe her ears and she let go of her skirt so it dropped back down again -- the boy had absolutely no respect!

"Jamie, adults do weird things in the privacy of their homes all the time, it's only normal. What's not normal is for a boy of your age resorting to this to get your kicks!"

"Yeah, yeah, whatever, jus' show me ya tatt would ya," Jamie growled impatiently, "or I'm goin' straight out that fuckin' door and plastering ya fuckin' porn photos all over the fuckin' place!"

"Wait on, wait on!" Latisha said, alarmed at his sudden impatient aggressiveness.

Slowly she started to lift up her skirt again.

And Jamie smiled, "That's better."

He watched on as she continued to raise the front of her skirt up past her thighs -- till finally her panties came into view. She had a thing for lace, he noted, and this pair looked superb, sheer black-lace with little scarlet flowers on them, quite small looking. He wondered if they were g-strings.

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