To Teach a Boy a Lesson Ch. 02

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Middle-aged woman gets carried away with guy's lesson.
9.3k words
4.56
71.5k
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Part 2 of the 2 part series

Updated 10/29/2022
Created 06/26/2009
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Latisha's (dubious) Plan Unfolds

It had been two weeks to the day that Jamie next walked back into Latisha's office, but this time he was there because she had asked him to visit -- had something to tell him, she had said, when she had bumped into him in the supermarket earlier that week. Now Latisha felt back in control. Duncan had finally been true to his word and the images on the website had gone. He of course did take pleasure in telling her to look after his mates in the future, or he would put them back up there!

She didn't take him too seriously.

Now with the youth, Jamie, standing back in her office, Latisha had quickly gotten to the point of her meeting with him and produced a small tape machine from her desk drawer.

It was an old Dictaphone that she used occasionally. Latisha had learnt from an old boss of hers many years ago, that it was a good idea to record meetings with clients candidly for numerous reasons, one of which was to cover your arse in case of some litigation claim, but mostly in case you had forgotten something important.

She plugged her desktop speakers into the machine and hit play.

Jamie listened to the clear recording with uneasiness -- it was an edited version of the 'meeting' he had with Latisha a fortnight before.

"So what?" Jamie mumbled arrogantly as Latisha turned the machine off.

"So what?" Latisha repeated, "Jamie, I have my evidence now. There is enough there to take to the police...and you'd be a goner!"

Jamie looked at her now with obvious concern, his face going pale.

"And another thing, now that you're over nineteen...you'd go straight to the big house."

"What?" he asked slightly confused at her suggestion he was nineteen.

"Your birthday...two weeks ago you said you had just turned nineteen?"

Jamie remembered his little lie, "Oh yeah...right."

He was worried of course -- really worried!

"I'm...I'm sorry, Miss, truly I am, I know what I did was wrong...really wrong," he said most sincerely, "It was only meant to be a bit of fun...you know. I thought that just maybe you were a bit of a slut...and just maybe you would...well, you know," he stammered nervously, "Please don't go to the police. I'll give you the money back?"

Latisha smiled -- now it was her turn to be surprised at how easy it had been. The table had well and truly turned!

"I want you to promise you'll destroy all images of me that you have...wherever they are," she said firmly, as the boy stood silently, almost hanging his head in shame.

He nodded, "Okay, is that all?" He was getting off lightly, he thought, far too lightly.

"And I also want my knickers back, you bloody thief! They're part of an expensive set you know, French too! My husband would not be at all pleased with me if he noticed them missing!"

He nodded again -- although he wasn't too sure if he could give them back to her, as unfortunately he had let his friend Eddie keep them.

"Is that all, Miss? Can I go now?"

Latisha looked at the youth shrewdly, somewhat surprised at how remorseful he now appeared to be. He was not at all the arrogant, stand-over young man of a couple of weeks ago and she wasn't too sure she should now go through with the rest of her plan -- the part where she had intended on teaching the boy a bit of a lesson.

Then she thought about the humiliation and degradation she'd felt because of him two weeks earlier -- no bugger him, she thought, she would go ahead with her plan.

Thinking he had been dismissed, Jamie turned to head for the door.

"Not so fast...you know I'd said I wanted to see you... for...maybe two hours," Latisha chuckled, a wicked smile forming as she looked at the worried youth.

He nodded, "Umm, yep, what else can I do then?"

"I want to show you something," Latisha said cryptically.

"What else ya got ta show me?" the boy snickered, "Pretty much seen it all, huh, 'cept of course ya tits!"

Well, that did it for Latisha; she was determined to go through with it now, as she saw a glimmer of the same young smart-arse that had tormented her earlier appear just beneath the facade.

"It's not here...its a few minutes drive away. We'll go in my car...you can put your bike in the office," Latisha informed him as she shutdown her computer and prepared to leave.

Barely ten minutes later, Latisha drove down an overgrown driveway to a ramshackle house on the edge of town and stopped under an old wisteria-entwined pergola. Jamie sat next to her quite sullenly not saying a word.

The property belonged to an old client of Latisha's who was terminally-ill in hospital. He had given her the keys some weeks ago so she could get some documents from his study. No one else lived there.

"Wait here a minute," Latisha said to Jamie, as she reached over to the backseat of her car and grabbed a small backpack.

Jamie watched the blonde woman as she unlocked the front door to the house. He just couldn't imagine what she was up to -- but he was worried.

Quickly he pulled out his mobile phone. He would like to have called his friend, Eddie, but he was nearly out of credit -- an SMS would have to do.

A few moments later, Latisha came back out from the darkened old house -- minus the backpack, and waved him to come inside.

With some trepidation, Jamie got out of the car and followed Latisha inside. She led him down a musty hallway to a large bedroom at the rear of the house, an ancient wrought-iron and brass bed sat in the middle of the room beneath a noisy ceiling fan. A tallboy set of drawers were against one wall and a worn red-leather divan was against the other, opposite a small window that had some sheer-netting curtains let in a small amount of natural light.

"What are we doing here?" Jamie asked a little incredulously.

Latisha looked at the worried youth, "Oh, you'll see soon enough. I wanted somewhere private to have a chat to you...somewhere we would not be disturbed," she said mysteriously.

* * *

Eddie and his older brother, Jacob, rode their bikes as fast as they could toward the address that Jamie had sent, while Eddie explained the situation as best he could to his brother. Eddie hoped it was not some sort of stupid trick Jamie was playing on him -- the message was a bit vague after all -- something about the blonde woman taking him to an old house and he was scared?

Scared? Not like Jamie at all, Eddie had thought.

Just over twenty minutes later, the two boys arrived. They could see a small, red BMW coupe parked discretely down the end of the driveway and Eddie was pretty sure it belonged to the blonde. Stashing their bikes, they cautiously snuck down toward the house. They had decided to just look in discreetly if they could, as they really had no idea of what to expect! They thought that maybe the blonde woman had a couple of heavies in there and they were going to rough Jamie up a bit for blackmailing her or something?

Slowly creeping down the side of the house, they checked each window for sounds, but heard nothing.

That was until they got near the rear -- then they heard it! It sounded like someone cry out sharply in pain -- not mortal or anything, more like someone who maybe had been pinched or something.

"Fucks sake, Jacob, I think they're may be torturing him!" Eddie whispered close to his brother's ear.

The two boys moved closer to the small window from where the sound had come from. Squatting beneath it, they noticed that it was partly open and silently, they watched the curtain flutter out every now and then, while they listened.

"Ouch! You really are a sick-bitch, aren't you?"

It was definitely Jamie's voice.

Cautiously, the two boys raised themselves a bit and peered through the gap in the curtain.

And they could not believe their eyes!

* * *

Latisha stood momentarily with her back to the window. She wore a tight black-leather corset that was tightly laced up at the back as well as the front. The three-quarter bra cups struggled to contain her heaving breasts as she pranced around the room in front of her 'quarry'.

She had black fishnet-stockings on which stopped just short of her buttocks and were held up by thin suspenders. On her feet was a pair of cheap platform stiletto shoes of a transparent acrylic.

Her hair was pulled up in a scruffy ponytail above her head and ringlets of fine curls hung down either side of her slim face, just in front of her ears. A cat-woman type of mask hid part of her face -- while her heavily rouged-lips stood out seductively.

Upon her arms she wore black gauntlets of a satin material that went almost all the way up to her armpits -- and in her right hand was a long, thin riding-crop that she waved around menacingly, while in her left, a pair of chromed handcuffs dangled loose.

The best part though, was her firm tanned-buttocks. They were quite bare -- with just a thin wedge of leather emerging from the cleft of her rounded arse, an integral part of the tiny leather g-string that afforded her some modesty when viewed from the front.

It was an outfit Duncan had bought her, but she had never worn for him and she now looked every bit the part of a dominatrix -- or so Latisha had thought. She was of course, a total novice.

Only several minutes earlier, Latisha had told Jamie to wait in the bedroom for her as she went into another room to change into her outfit.

When she had returned -- feeling more than slightly embarrassed -- the youth's eyes had nearly popped out of his head. Never had he seen anything like it for real before!

Her heart had pounded fast in her chest as she'd stood there smiling at him -- and she'd felt the power -- and suddenly it had excited her more than she could have ever imagined!

She paraded in front of him -- purposely -- teasing him -- taunting him.

And when her back was to him briefly as she dropped the handcuffs down carelessly onto the bed -- Jamie had tried to touch her -- and she had turned suddenly and whacked his hand with her riding-crop, making him cry out.

Now Latisha sized-up her prey.

"So you like what you see, do you?" Latisha asked him wistfully.

He nodded vehemently. He could not believe how his luck had suddenly changed so dramatically. Was this meant to be some form of punishment?

"I'm pleased," she said, slowly licking her lips, "Now I want you to do something for me, Jamie."

"What?" he asked her, raising his eyebrows with obvious interest.

"You can start by taking your jeans off."

"What...what in the fuck for?" Jamie snapped nervously.

"Pretty obvious isn't it?" she said, "You saw my pussy the other day...now I want to see your penis!"

Jamie looked at the old bed, and then back at Latisha, "You gonna...you know...umm, you gonna fuck me then, too?" he gulped eagerly.

Latisha laughed, "Maybe...is that what you want?" she asked seductively.

He didn't answer directly, but instead, he hastily began to fumble with his jeans as he did his best to undo them in record time. Strangely, it was now Jamie who felt embarrassed under the scrutiny of Latisha as he let his jeans drop to the floor.

"And...your undies too, please!" she said slowly as she smiled.

The lad pulled a face as he slid his jocks down his legs until they dropped around his ankles and stood back up, hoping she would not laugh at his shrivelled penis.

Latisha looked on at his discomfort with satisfaction; she wanted to humiliate him just a little, like he had done to her, if that was at all possible.

She glanced down at his flaccid penis, "Play with it!" she ordered, "I want to see it hard!"

"I...I don't think I can get it hard, I...I need to see something to get me excited first," Jamie stammered softly.

"What! And me going to all the trouble of dressing like this! What's wrong with you? Are you gay or something, maybe that's why you didn't screw me when you had the chance...not because of any guilt-thing at all?"

"I'm not gay ya fuckin' bitch!"

Latisha lashed out with her riding-crop again -- but this time she clipped the end of his penis as it dangled between his legs!

"Ouch!" he cried out, quickly covering his groin in case she took another swipe. Even though his cock stung a little, it had kind-of felt good -- in a weird sorta way, he thought, and he started to play with himself.

"That's it, Jamie, start wanking it for me now, alright!"

Slowly the youth began to stroke his penis and Latisha watched it lengthen considerably, but it did not appear to grow very hard.

"Christ's sake, is that the best you can do? And you wanted to fuck me! That's a joke; you're really just a boy, aren't you!" she said contemptuously.

Nervously, Jamie continued to stroke himself slowly. He felt extremely embarrassed of course, as never before had he masturbated in front of anyone.

"I don't think you had too much of a problem the other day...when you were looking at my hot, dripping pussy...did you...maybe you would like to see it again?" Latisha purred suggestively.

Now Jamie could feel a familiar stirring in his loins; the blonde woman's crude suggestion titillated him.

"Oh, you like that idea, hey? Cock starting to come to life is it?" Latisha observed wryly as the boy's penis grew steadily less than an arms-length away from where she stood watching with more than a bemused interest.

"This help you a bit more, Jamie...hmmm?" Latisha asked as she rubbed herself lightly through the front of her tiny leather g-string with her right hand, "Maybe you'd like me to take them off too?" she asked as she slowly inched the front of them down a few centimetres, exposing the better part of her mound with its little patch of short pubic hair.

Jamie nodded, and he looked on excitedly as his cock began to grow steadily larger, and larger.

"Mmm...now that's looking better...but now I want you to take the rest of your clothes off too," Latisha ordered with excited emphasis.

The boy complied readily this time, his earlier embarrassment waning. She watched him strip off completely, and then stand before her naked, his large erection stood out several inches at around a forty-five degree angle as he continued to stroke himself for her amusement.

"Hmmm...looks quite impressive now, young man!" Latisha nodded, as she ran her tongue around her rouged-lips sensuously.

It was not only his hard penis that impressed her -- no -- but his firm young body that looked delightful. He was toned to the max, with not the slightest amount of flab anywhere --quite a rarity in this day and age of juvenile-obesity, she thought.

"Take your hand away," she said huskily, "and stand-up straight for me."

Slowly, Latisha ran her riding-crop across his hairless-chest, and down his flat stomach -- hesitating just above his groin, while he stood there anxiously -- gradually she moved her crop down even lower, to the base of his hard penis, and very carefully, she traced its outline with the cracker at the tip of her thin whip. Latisha could see just a hint of clear pre-cum oozing out from the end of his circumcised-glans -- and she smiled wickedly. She was going to enjoy 'torturing' him a bit more.

"Good...very good, and now I want you to put these on," Latisha said, handing him a pair of red g-strings of hers that she'd tucked beneath the bottom of her tight-corset earlier.

"What for?" he asked, frowning cynically.

"Thought you liked women's underwear, Jamie?"

"I do...but not to fuckin' wear, you sicko!"

Latisha shook her head and clicked her tongue several times, admonishing him, "Be nice now, my dear boy, won't you," she said, as she slowly reached out with the riding-crop again, and stroked the underside of his long penis, "Just put them on, would you...and I'll promise not to tell anyone...anyone," she said demurely.

Jamie stood there thinking for a moment as she continued to stroke his cock gingerly, "Tell ya what...I'll put 'em on for ya...but only if you take yours off...deal?"

She looked at him astutely for a few moments as a tingle fluttered in her pussy -- his lewd suggestion had managed to incite her exhibitionist tendencies almost instantly. Latisha also tried to quantify it with the belief that it would also help torment him even more -- and after all that was what she wanted to do, she mused.

"Mmm...okay then...I guess," she said softly, her dominatrix act appearing to falter.

Jamie smiled, and took the red g-strings from Latisha, then stepped into them and pulled them up into position. His cock stuck out somewhat ridiculously from the band of the small garment as he now stood there expectantly waiting for Latisha to fulfil her part of the bargain.

Latisha could feel her pulse racing through her veins -- and she wondered whether she should stop her little charade then and there. She was after-all, only ever planning on teasing him a bit -- certainly not give him too much of a thrill.

But seconds later, and thinking little more about it, she released her grip on the handle of her whip, and let it dangle from its strap around her wrist. Looking pensively at the youth, she slowly ran her finger-tips down along the outline of her breasts, and down the sides of her slim, corseted-waist, till she came to the narrow straps on either side of her hips. She unclipped the small buckles with little difficulty, and sliding her high-heeled feet apart, she opened her legs quite provocatively, and let go of the tiny, triangular piece of leather and it fell to the floor.

Jamie grinned excitedly, looking down at her bare quim, his cock throbbing with excitement, "Now what...do you want me to keep tugging me self?"

Latisha wasn't too sure -- but she was acutely aware of her own increasing state of arousal -- she would have to be careful!

The boy's eyes continued to drink in her near-nudity, and Latisha was certain his already impressively swollen-member grew even larger! But now strangely self-conscious, she placed one foot in front of the other, closing the gap between her legs, while she was thinking of what to do next.

Then she remembered the collar!

"Wait a minute," she said as turned to walk out of the room.

Jamie lent back against the foot of the bed and watched her intently as she walked out in her ridiculously-high shoes with her hips swaying sexily -- he really thought her stockinged-legs looked shapely and he just loved the way her lovely arse jutted outwards provocatively -- almost beckoning to be smacked!

"Pssst...Jamie!"

Startled, Jamie looked over toward the bedroom window not more than three metres from where he stood and saw two grinning faces appear from between the tattered curtains.

"Eddie, Jacob! Geez you'se gave me a fright! Can you believe this, huh?" Jamie whispered, quickly covering his erection with his hands.

"Are you alright?" Eddie asked in amazement, looking at his friend dressed in no more than a pair of ladies red g-strings.

Suddenly Jamie could hear Latisha's footsteps approaching on the polished-floorboards -- she was returning! Quickly, he nodded to his friends he was okay, "Shush, won't you," he whispered, putting his forefinger to his lips warning them to be silent.

They both nodded, and disappeared beneath the sill of the window.

He felt his confidence rising again now knowing he was no longer alone with the devious older woman.

Latisha sauntered back into the bedroom while carrying a black-studded collar and a silver dog-chain in her left hand. She was of course completely oblivious of the company that was just outside the window.

Jamie frowned as he looked at the chain and collar that was in one hand -- and the riding-crop that she was still holding in her other hand. But then he glanced back at her crotch as she stood facing him with her feet several inches apart. He just loved the way the little strip of pubic hair above her slit helped accentuate her smooth, hairless vulva. Nice, he thought, very nice! He really found it hard to believe she was as old as forty-two!

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