Spoiled, arrogant, and from a wealthy family, college boy Josh Adams fatefully thought he could put his housekeeper in her place when she required him to perform household chores during his summer vacation. The tables would be turned, and oh so soundly.
Cocksure Vanity
Josh Adams stepped through the terminal doors and faced the airport traffic. He watched the cars and buses go by and almost got nailed by a taxi as he stepped off the curb to get a better look. No, he didn’t see the Bentley. As he kept vigil, he noticed a girl looking at him, obviously flirting so they exchanged smiles. She was with her family and leaned towards her mother and spoke into her ear. They both checked him out, smiling. Josh was a handsome young man and wore his short and close-trimmed beard very well. Skinny jeans nicely accentuated his muscular build, especially his ass. Josh did have a big, muscular bottom which the guys on the soccer team teased him as his junk in the trunk. Too arrogant to blush at the flirtation, he knew how hot he looked and just smiled again while the family with the cute girl waved at him as they drove past.
Chauffeured Bentley
“Too bad, it wasn’t meant to be, Baby,” he thought as he waved. Then he heard the horn and saw the silver Bentley as it angled towards the curb and the trunk popped open. Mr. Summers, dressed in his chauffeur’s togs, loaded the trunk and with a slamming of doors, they were off.
“Your grandmother sends her regrets as she won’t be back from the Grand Caymans till late August. When do you start back to university?”
“I’m not going back till September, I guess I’ll get to see her for a week or so. Just as well, I love Grandma, but sometimes she drives me crazy.”
Summers guided the Bentley from the airport lanes onto the freeway. “I know, young Joshua, she’s a pill alright, but you gotta love her.”
Summers looked a bit older, but he was still a handsome man, now more distinguished looking. He’s been driving for Grandma for at least fifteen years or so. He remembered the younger Mr. Summers, playing ball with him and throwing him into the pool. And he remembered him always threatening to spank him, but it was only a joke. There was no spanking in Josh’s family from any adult, at any time, and look how well he turned out.
They left the freeway onto the boulevard, lined with luxury apartments and large homes, clearly the affluent part of town.
“So, I guess it will be me and you till Grandma gets back,” Josh inquired.
“Not exactly, after you left for school last year your grandmother hired a house woman.”
“A house what?” came Josh’s perplexed response.
“Woman,” Summers drawled with emphasis.
“What the hell is a house woman?” Josh asked with growing exasperation as he leaned forward.
“She’s like a governess, you know, takes care of the house, manages the staff, the maintenance, and me, she sort of runs everything, and is a close companion to your grandmother. The old girl is crazy about her. You’ll meet her, odd sort of person. Her name is Miss Alcott.”
“Is she hot?”
Summers busted out laughing, “Well, kid, if you think a very tall, sixty-nine-year-old spinster is hot, well, then try your luck.”
“She’s sixty-nine years old? Well, that’s probably better for Grandmother anyway, I’ll be going out to the clubs, making the rounds.”
“I’m sure you will, and you won’t have any problem.” Summers cut the wheel to the left and the car bounced into the drive, past the gates as the big Victorian loomed ahead.
“Grandma is still keeping this museum up, eh?”
“Actually, Miss Alcott is. The place got ahead of your grandmother for a while, but, now, everything is spiffy and runs like clockwork. Let’s get you inside so you can meet the dragon, I mean Miss Alcott.”
As they both turned from the car, the front door opened and the dragon, I mean, Miss Alcott stepped out onto the porch.
“Ah! Young, Master Joshua! You have arrived!” She stood with sort of a smirk type of smile on her face. “Summers, please take his bags up to his room. Your room has been prepared for you, Joshua.”
“Call me Josh,” as he stuck out his hand, which she shook limply. “Everyone else does,” he encouraged.
“I suppose Mr. Summers told you that your grandmother will be back late August. We’ve talked about your visit.” She looked at Mr. Summers, visually dismissing him. “Your grandmother and I, that is, both of us feel that since this is such a lengthy visit, you may benefit by assisting with some of the responsibilities around here. I shall help you get organized.”
She turned and strode into the house then veered off while Josh followed Summers upstairs to his room.
“Dragon lady for sure, as well as a big, walking ice cube,” lamented Josh.
Summers laughed.
Josh shook his head, “Man, she’s in for a rude awakening, I’ve got plans, I’m not going to be her hired help. Fuck that!”
“Shhhhhhh,” warned Summers with a finger over his mouth. “She doesn’t like foul language, just about took me over the coals for using the same fucking word.”
The two of them laughed, but at the bottom of the stairs, out of sight, someone was not laughing.
The Good Life
During his first week, Josh swam, played tennis, and went to the bars. Miss Alcott left him a short list of tasks that she wanted him to accomplish. It wasn’t much, but it wasn’t happening. Unfortunately, this arrogant young playboy didn’t realize who he was dealing with, yet.
At the end of the second week, summer was on and Josh had some friends over for an informal weekend pool party. Feeling like the lord of the manner, they had drinks while Josh felt free to order Miss Alcott to be their server, she complied but Josh, oblivious, did not see that she was seething. That was over the weekend and that little party was the final straw. Monday came and it came hard.
It was Monday evening and Josh was leaving, he needed a hook-up as the babes at the club were smoking hot and waiting, but as he walked by the living room he was verbally collared.
“Mister Adams!, a word please!” Josh stopped and regarded the Alcott dragon.
“Yes, what is it?”
“We need to come to an immediate understanding, young man.”
“Well that’s all well and good, but I’m going out now.” Josh turned towards the door, but she moved into his path.
“This will only take a moment, into the parlor, please.” She did a grand directional gesture towards the room, to which Josh complied and they both went in.
“Sit down!” It was an order and Josh bristled, but stifled himself. “Both your Grandmother and I run this house. You being a full-time student are only visiting for the summer. Despite your grandmother’s wealth, you cannot live a life of sloth and debauchery while you’re here. I made it quite clear that you are to have some responsibilities while staying, which, by the way, is something that most households of nearly adult children maintain, or at least, should.” She cocked an eyebrow at him. “Yet, Joshua, you insist on acting like a spoiled, petulant, and disobedient child.”
Josh’s face flushed. “I said call me Josh, not Joshua, and you are the help, I am the family! In case you didn’t know, Miss Alcott, we have all kinds of people hired to keep this place up, from the pool company, to the landscapers to Mr. Summers, and besides lady, I am twenty fucking years old!” With that Josh stood up and strode out the door slamming it hard. He was quite pleased with himself as his manly and forceful response seemed to put the old dragon in her place. That cast iron face of hers looked for a moment as it just had been slapped. He drove off thinking that he set things straight. But, he should have seen the tight smile on the dragon’s face as she watched him leave.
Josh had a great time at the club: He hooked up with some friends, met some babes and got a couple of numbers, and was as getting half-looped. When he got home at two thirty in the morning, the porch light was on. After putting the Bentley to bed, he crept quietly through the door, and then stopped. “Why am I sneaking in like a high school kid who broke curfew? This is my house, and she’s the help”. He smirked and strode through the grand entrance and up the steps two at a time, fueled by too much beer, he strode down the hall to his bedroom, and slammed his door shut. “Fuck the dragon lady,” he thought with bravado.
You Work for Us – Got It?!
The next morning after his shower, Josh left his bedroom heading down for breakfast and a morning swim, but as he opened his door there was a note tacked to it. Ripping it down, he read:
Good morning, Joshua:
I trust you had a good time last night. As we discussed, here are the chores that you need to accomplish, today:
1) Clean the pool,
2) Wash and wax the Bentley (since you’ve been using it),
3) Cut the lawn.
Thank you,
Miss Alcott
“The fuck I will!” Josh railed, balled up the note, threw it down, then strode down the steps following the smell of coffee.
“Good morning, Joshua! Have some coffee and breakfast, then you can start on those tasks. Just so you know, Mr. Summers is happy to have you wax the Bentley, since you’ve been driving it so much. We’ve already pulled out the riding mower for you and until I find a new pool company, taking care of the pool will be your responsibility.
“If you start now, there will be plenty of daylight left for a swim in the pool, so, the sooner you get started, Joshua, the more free time you’ll have for your (she cleared her throat) other activities.”
Josh’s face flushed hot and red with anger as he poured himself a cup of coffee. The tirade began: “You ancient bitch! You just don’t fucking get it, do you?” He glared at her, walking towards her and that’s when he realized she was taller than him, he adjusted his eyes a bit upward. “You’re the fucking help, I am family, you do not tell me what to do and when to do it. Got it!? Now, I’m going to swim in that pool and I am not going to clean it!” She stood there like a statue, her face unreadable. As far as he was concerned, he was going to lean on Grandma and get this stupid bitch fired.
The morning was beautiful, sunny, and warm, no way was he going to wax the car or cut the grass, even though the tractor would make it easy, and he certainly wasn’t going to clean the fucking pool. His blue Speedos worked hard to encase his ass and clearly were to blame for those tan lines angled across those shapely cheeks. After a good swim, he toweled off bent over to get his legs, while inside Miss Alcott was watching, admiring, and preparing. It was time to teach this overgrown brat a good lesson: She had the authority, the physical strength, the method to do it, and, most of all, iron resolve. Poor Joshua had no idea of the bond she and his Grandmother had formed as they both agreed to prepare the boy for the responsibilities ahead. But no one had any idea how much Miss Alcott would enjoy “preparing” him.
An Old Fashioned Disciplinarian Emerges
“Joshua! In here, now! We are going to talk.” She stood within the open French doors of the music room, one of the many common rooms that opened to the pool and patio.
“What do you want now?” Josh entered the room, and for a brief moment, Miss Alcott had to steal herself as she took in the young man’s perfect form – soon to be naked and in pain.
“Obviously, you think you can bully me. You cannot, boy! I will not tolerate it!”
“Boy! You’re calling me boy?” Josh was further outraged raising the volume of his voice. In contrast, Dragon Lady spoke in low tones forming her words succinctly.
“Yes, I am, because you are acting like one: A spoiled, recalcitrant, child, therefore I am going to treat you exactly like one!”
“Really! Who the hell do you think you are? My grandmother is . . . ”
She stepped aggressively toward him getting in his face: he froze. “Your grandmother is what, Joshua? Go on, your grandmother is what?”
He blinked, as the saying goes, and she moved in. “Your grandmother and I are on the same page! I am not your maid, Joshua, nor am I here on some kind of whim. You are going to learn, Joshua, and, I am going to enjoy teaching you!”
Naked for a Strapping
“Teach me what?” Josh tried to muster up more bravado against the dragon lady’s sudden, overbearing aggression. Actually, it was more than aggression; it was a larger-than-life dominance of the likes he had never experienced.
“Take off those trunks!”
“What!?”
“I said take off those swimming trunks, now!”
Josh was shocked, she was so in his face, yet she was not yelling or screaming, but her voice had authority, and it scared him.
“No, I’m not taking off my trunks, I’ll be naked, what the hell’s wrong with you? What the fuck do you think your doing?”
She gave him a tight-lipped smile that was quite unnerving. This experienced senior woman was full of indignant rage fueled and amplified by another, somewhat impure, motivator, wonderfully blended for a perfect storm. Josh did not know that her dominant personality was now a runaway train with no brakes. It was time to move, time to act; she seized his ear and twisted it, hard.
“Owwww! My ear! Leggoof my ear!”
“Remove those trunks, now!” she commanded as she increased her hold on his ear.
“No! Ow! Your hurting me! Let go! Let Go!” Then, suddenly, “Please!”
That was a win, now her excitement was not running as hot as her anger.
“Please what, boy?”
“Please, let go of my ear”. Not just yet, she thought, and twisted his tortured ear a bit more as he howled and turned his head into her grip.
“Want me to let go of your ear, then remove those damn trunks now!” Her voice was low and strong.
And winning the first round, Dragon Lady one, Josh zero. As he bent to remove the trunks, she relinquished her clamp on his ear. She thought she heard a whimper as he stepped out of the wet Speedos, then stood facing her in total, glorious, nakedness.
”Wha-what are you gonna do?” His ear was as crimson as his face.
“Why, I’m going to give you a life lesson, Joshua”, she stated sweetly with delight. A lesson you’ll remember for a long, long time.” He got the chills, as she smiled at him her expression almost seemed evil.
“Now turn around, and place your hands on the arm of that chair, yes, that one, and hang on tight! Do not let go, understand?!”
“No, please.”
“Do it.” He did, his arrogance evaporating like water on hot concrete.
She laughed inwardly at how easily he was intimidated.
“Now, boy, spread your legs! I said spread them, Wider! Wider! Yes, that’s it.”
Bent over, afraid to move, he was truly scared.
A Lesson Taught With Spanking Leather
“Oh, my God! Whaat are you gonna doo?“
“Quiet! Now, present that bottom!”
“What?”
“I want you to present, like this.” She placed one hand across the small of his back. At the same time, she used four closed fingers of her other hand, turning her palm up, and placed those fingers in his crotch just behind his balls. The touch shocked him.
“Hey!”
“Never mind, just let the motion of my hands direct you, and that bottom will roll up, and out to me. Yes, that’s it, very good. Now, keep it like that. Up on those toes, boy! Do you understand?
What a sight Joshua was. Broad-shouldered, trim wasted, muscular legs spread and his posterior, that muscled posterior, rolled out, and opened up like a brand-new flower. She was getting wet.
“Now, we will proceed till I’ve decided that you’ve learned something, and stay up on those toes!”
“Wait, proceed with what? No! I don’t . . . “
“Woosh! Crack!”
“Yeeooow!” His butt cheeks were suddenly on fire.
Josh’s knees gave out and he tried to look back at her.
“Get back into position, Joshua,” she stated in an almost pleasant tone. “Head up, young man, eyes forward!”
Miss Alcott has just applied a very wide, doubled-up, leather strap viciously across the boy’s bare bottom burning both cheeks at once. A nice imprint of deeper color appeared. Joshua regained his position just in time for the second stroke of the strap.
“Oooww! No! No!”
“No? Oh, Joshua, are you still telling me ‘no’?”
The third lash landed, expertly placed higher than the first two.
“Oooww! Oh, God!”
“Keep those legs apart. Up on those toes! That–a-boy! Now let’s have another, shall we.” She sounded almost cheerful like she was offering him a second piece of cake.
“No! No! I’ve had enough! It burns terribly!
“Oh, poor Joshua, I decide when you’ve had enough.” He couldn’t see her smile, and that was probably just as well. She was enjoying herself so much, and as enjoying a great meal, she was going to make this last. This arrogant, spoiled boy was now being taken down a peg, and what a target, what a specimen! It made her ever more excited as he was so deserving of her “life lesson”. Clutching the supple strap she delivered three consecutive snaps in quick succession. They burned hot and wicked.
“Eeeooooooowwwhh!” His hips dipped from side to side. She placed an open, up-turned palm gently against his solid belly just inches from his erection. Erection? She was tickled pink! “Well, well,” she thought, “Joshua, what a big boy you are!”
“My goodness, little man, what a big, round, naughty bottom we have — so much territory to cover.” She giggled, she really giggled. “Just look at what you make me do!” as she turned her attention to the lower part of his bottom.
“Roll that bottom out for Miss Alcott. Yes, like I showed you, roll it out. See, you can cooperate.”
He looked back at her, the expression on his face was priceless.
“No please, no more!”
The strap ignored him and two more snaps blessed his bottom.
“Oh, my God!”
“Now don’t be a shrinking violet, Joshua, keep that beautiful posterior out for me, I’m not finished painting it.”
Another solid lick landed a bit higher than the previous two.
“Owww! No, no, please, I can’t take no more!”
“You mean, Mr. Joe College, you cannot take any more! Well, that is just so unfortunate, young man, so unfortunate because there is so much more to take.”
Josh whimpered like a scared, little boy.
She administered six licks of the strap in lightening-fast succession, starting from the tops of his thighs, then revisiting those low under curves that drove Josh up on his tippy-toes almost dancing in place. Frantically he shook his hips from side to side as if desperately trying to shake off the burn.
“Ahhhhoooooo-pleeezeeee!” A pitiful tone framed his response that sounded like one long, protracted word.
“Now, Joshua, (she was smirking), remember you told me you are a big twenty-year-old, yet, listen to you fuss. Why, you sound like a big baby.”
The bitch was all smiles as she draped the strap over her shoulder and admired her handy work.
The Alcott Dragon patted his fanny.
“Oh, my Goodness! just look at this bottom! This twenty-year-old bottom, so much to learn, just so much to learn”
With that she placed her hand gently on his posterior and lightly rubbed his cheeks in soothing circles freely wandering down into forbidden territory, luxuriating in the light dusting of hair that was in the land down under. Josh moaned pitifully as her hand passed on either side of his drawn-up testicles.
Reluctantly she removed her exploring hand, took the strap and snapped it. Josh winced reflexively, hearing the snaps he pleaded openly.
“Please, Miss Alcott, please, no more!”
But it was not time to stop, tt was time to ice the cake. It was time to drive her point home. It was time for all good young men to be reduced to tears. In other words, the fat lady hadn’t sung yet.
The dragon resumed the merciless strapping of his tormented flesh without any hesitation between lashes. Her strap sang through the air and burned across both cheeks painting them top to bottom, then bottom to top, punishingly inflaming the fire red.
Joshua began to cry and bawled openly as his handsome head turned from side to side, obediently keeping a death grip on the chair.
Without missing a beat, she chided him.
“Oh, poor, little, Joshua, it seems you don’t like my strap. Well, I also have a paddle, and if need be, young man, there is always a place for you over my knee!’
Josh frantically danced on tip toes, from one foot to the other, shaking that throbbing, angry, red, ass and pleading loudly. In contrast, the dragon lady leathered him in a smooth fluid movement.
“Well now, Master Joshua, are you going to listen to me now?” the question was stated as the strapping bore on, relentlessly.
“You will cut the grass?” asked as the strap stung mightily.
“Owww! Ooohhhh! Yes! I will! I will!”
“My, such a dulcet baritone you have, young man, and oh yes, wax the car?” came the next question as she laid the strap well on.
“Pleeeezeeee! Yes! Oh yes! I will!”
“Clean the pool?” as the strap struck faster.
“Ohh yessss! Yes! Yes! Yes! Every day! I promise! I promise! No more, I’ll be a good boy, I promise!”
The final, fast and furious volley of searing lashes were placed across the low, meaty, sweet spots of his athletic ass, received them in perfect form as he stood up on the balls of his feet.
Josh bawled openly, his please and promises becoming unintelligible.
“Listen to you, such a fuss, over a little strapping! You act like a little baby, not a big, grown up twenty-year-old. Next time, little man, you will go over my knee.”
With his ears and face almost as red as his rump, and crying real tears, it was finally over. And if he thought this was his last spanking of the summer, he was very mistaken.
“Okay, Joshua, now you know where we stand with each other. And just so you know, your grandmother has fully approved of what I just did. Now, what are you going to do?”
Josh sniffled and rubbed the tears out of his eyes. Standing to face her, his humiliation burned as much as his bottom that he openly rubbed. He was so grateful that the house was empty and Mr. Summers was not around to witness this, or anyone else for that matter.
“I’m gonna cut the grass, (sniff) and then clean the pool.”
“And then?” as she placed her hands on her hips.
Josh was rubbing his bottom. “And, wax the car.”
“Very good, young man. We are done here, so you can get started”
She stood there smiling, the strap classically draped over her shoulder. Josh picked up his trunks and walked his crimson, angry red, thoroughly punished bare bottom up to his room.
“Ah, I’ll get dressed and start on the lawn,” he wisely resolved.
She nodded in approval, still sporting that tight-lipped smile, as she watched those perfect, muscular red cheeks go up the stairs. She turned just as Mr. Summers walked in from the patio smiling.
“That was quite a show, Miss Margaret Alcott, Margie,” he snickered, adding “I hope you follow through with that over-the-knee thing.”
“I certainly will keep you informed, Mr. Summers. “
The dragon lady turned to leave taking the strap off her shoulder.
“And I have to thank you, Mr. Summers, You were so right,” as she snapped the black, disciplinary leather a few times.
“This is exactly what he needed.” They both laughed.
A very well-written story! I loved the age difference between your heroine and the uppity antagonist. It was a very exciting and satisfying read of a strong-willed older woman taking the self-assuming grown man and reducing him to the whimpering little boy he actually was. Well done, sir. Kudos!