Henry's Home for the Summer

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Henry's mother has hired a governess to supervise him.
3.9k words
4.35
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Part 1 of the 8 part series

Updated 06/08/2023
Created 04/28/2017
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Although Henry was 18 and had finished his freshman year in college, he still looked young for his age. He was not happy about going home for the summer because he knew that he would soon be back under his mother's thumb at home, after enjoying a delightful two terms of freedom at his university.

He had tried to schedule some courses there for the summer to get ahead of schedule and to avoid returning home, but his mother and father had insisted that he return. His mother was very controlling. He knew that she dominated his father when they were in their bedroom as he had seen her tell him to go there when he said or did something that she found unacceptable.

She had brought him up under strict discipline as well. Henry had been spanked from when he was a child all the way through high school and he knew that when he got home, he would still not be spared. But he finally faced up to the fact that he had no way to escape a certainty of an unhappy summer in front of him.

So he packed his bags and set out for home. When he arrived, he walked in and his mother was sitting in the living room reading, as she usually had been. She rose and have him a swift peck on the cheek and told him how happy she was to see him in her misleadingly sweet tone that masked a will of steel.

She accompanied him upstairs where she told him, much to his surprise, that he would be using his sister's room, because she, his mother, had taken his room for her use. His sister was off in Europe on a fellowship, so as much as he resented losing his own room, with his own things, he decided he'd better not make a big deal out of it.

His sister had been just as dominant as his mother, so he was satisfied in reminding himself that at least she wasn't there to come down on him too.

But now as he looked around his older sister's very femmy room—all in pink and white with delicate lace bedspreads and curtains, he started to get annoyed. Then he opened the chest of drawers and as he would have expected, he saw Cynthia's underwear and tops and the like, along with dresses and skirts hanging in the closet.

But he took a closer look at these clothes and realized that they were in a larger size, closer to fitting him rather than his petite sister!

Henry figured it was better not to say anything about this because it would just stir things up. But he now anticipated that his mother had things in store of him that he was not going to like.

He went back to the living room and asked his mother where there was room in the closet and chest for his things.

"Oh," his mother answered in a calm tone, "there's an extra drawer for you and room at the right of the closet." She then went on to mention that his father had set up two or three interviews for him for office jobs that she was sure he would be well qualified for and which would allow him to save some money for school.

"You know that we're not millionaires, Henry," his mother said rather bluntly. "You have to help earn some money this summer to help pay your way." Again, he kept his thoughts to himself. He knew that his parents were rolling in dough. His mother was smartly if conservatively dressed, and the house was quite substantial. His father may have been dominated at home but he made a fine living as an investor and hedge-fund partner.

"I wanted to take a little time to relax," Henry said calmly. "I don't want to start right in Monday on working."

His mother looked severely at him and answered, "Your father has been good enough to go to some effort to line up these interviews. You will go to them, do your best to satisfy them as to your abilities, and you will accept the one which pays the best."

"Can't I get a little consideration?" Henry rejoined, momentarily losing his cool and letting his anger surface. "I've worked hard at school all year."

"I don't like the attitude you seem to have acquired," his mother snapped back. "You obviously have not had the disciplining you need and I intend to do something about that."

"I'm too old to be spanked like a little kid," Henry complained.

"You are not," his mother answered in a very firm tone. "In fact, we will go up to your room to do just that." With that, she took him by the ear and led him back upstairs to his sister's room, now his.

His mother sat on the bed and told him to take off his trousers. He realized he had to comply, that as always, she was in charge, so he dropped his pants and took them off. He stood in front of her, feeling already like a younger boy, in his white y-fronts, the jockey shorts he still preferred.

"Take those off too," his mother barked.

He complied and stood there totally embarrassed already, not two hours home.

Then his mother motioned to him to take off his shirt and his undershirt, which he did.

Now she had him lie across her grey flannel-skirted lap and then suddenly he felt her spanking hand start inflicting hard spanks on his bare white bottom.

He had not experienced her strong spanking hand on his bottom for a long time—almost a year. She clearly had lost none of her prowess in inflicting a stinging spanking. The spanks kept raining down on his bottom and he especially felt them now aimed at the tender curve from the base of his bottom onto his thighs.

It wasn't long before Henry was unable to hold off tears as the spanking, which hurt just as much as he now remembered. He couldn't see how red his bottom was becoming, but finally, after he had been made to plead for mercy and cry, things he had vowed never to let himself do any more, the spanking ended.

****

Henry duly put on a nice suit, shirt, and tie to go to the interviews his father had arranged. The jobs were surprisingly interesting, at least from the descriptions the men, slightly younger than his father, provided. He was pleased that he actually would be getting a decent intro to the financial world.

That night at the dinner table, his father questioned him carefully about the interviews. His penetrating questions made Henry think hard about the different aspects of each office where he could be working.

"We need to decide this quickly," he said to Henry. "Have you a strong preference?"

Henry thought for a moment and answered that he liked one at which the executive to whom he spoke seemed to take more of an interest in Henry's particular skills and school course background.

"That's fine," his father said with a satisfied look. "He will indeed look after you well."

Despite his longing for some free time, Henry reported for work the next day. He had worked in offices before, but this time, he admitted his father had done well by him. The executive who hired him made sure Henry met everyone involved in the operation and had given instructions to include him in all the important tasks that would benefit both Henry and the firm by Henry's learning to play his assigned role.

When Henry came home, he was exhilarated. But he saw the look on his mother's face and his face fell. She told him he was responsible for cleaning his room every morning and that he had not bothered to make his bed or tidy up his things that morning.

"Can't you ever give me a pass for once?" Henry complained. "I'm starting this job and it really looks good and I really do appreciate what Dad did for me, but I still do need a little time to adjust."

"I don't like your speaking to me like that," his mother snapped. "But I've decided on a new way to deal with this problem." She motioned to Henry to follow her into the house.

Sitting on the living-room sofa was a stern-looking, dark-haired young woman who was likely in her 30s, quite mature and smartly, if conservatively, dressed in a severe-looking white blouse and a grey-flannel skirt with sheer hose and pumps.

"This is Miss Ames," his mother said. "I've retained her for the summer and she will be your governess. I'm placing her in complete charge of you from the time you come home from work—which, incidentally you will do, as there will be consequences if you come home late—until you leave the next morning. I don't need to bother myself any more with this particular problem.

Miss Ames then smiled at Henry and said, "Your mother tells me that you haven't been very good about cleaning up. We'll start out by working on that."

Henry was totally nonplussed by this whole turn of events. "I don't need a governess," he said loudly, "I need some time of my own."

His mother looked over at Miss Ames and said to her, as if Henry were not present, "You see what I mean. He's totally obstinate and you will have to deal with that."

Before Henry realized it, Miss Ames stood up, walked to him, and grasped him by his ear, in time-honored fashion of governesses about to discipline a charge.

"Henry," she said softly but very severely, "you will learn that you do better by following my instructions. If you don't you will suffer the consequences, usually immediately."

Without further words, she carefully removed Henry's suit jacket, unbuckled his belt, unbuttoned and unzipped his trousers, and crisply pulled down his white jockey shorts. Seemingly in one motion, she sat on a straight chair and took him right across her grey-flanneled lap.

Before he could utter anything more than a high-pitched whine of "Nooooo!" she was spanking him, crisply and in what appeared to be an even more powerful manner than his mother, who was no mean spanker, had done the previous day.

Margaret Ames was an experienced disciplinarian. She herself was a business-school graduate who now taught at a well-regarded university nearby but was now herself on summer break. She had worked her way through school taking care of difficult children for parents who had run out of options when regular caregivers spurned their charges. Word of her strict effectiveness at behavior improvement had circulated among the better-off segment of the community.

Henry was now amazed at how much this spanking was hurting, his sense of self as well as his bottom, which had not yet recovered from the hard spanking his mother had inflicted on it. He also was embarrassed that he was aroused by Miss Ames, and couldn't help imagining even while over her lap and being spanked severely by her.

He began to think about what she looked like in bra and panties and even without any clothing. Did she shave down there like some of his college girlfriends did?

Margaret Ames felt his arousal on her lap and moved her legs so that his member was now caught between her stockinged thighs. She kept spanking him and soon was not at all surprised when he gave out a little cry that made it clear that he had lost control and spurted on her hose.

"I think we've had a little accident here," she smilingly said to Henry's mother. She had Henry rise and handed him a soft towel to clean himself up. She herself took the matter of her now wet hose in stride and told Henry to go to his room and that she would follow soon to go over "her rules" with him.

Henry was ashamed and quietly pulled up his shorts and suit pants. He then walked out of the living room as quickly as he could without running.

Margaret smiled at Henry's mother. "Don't worry about me," she said with a confident tone, "this often happens as these boys can't help thinking romantically. It's not me so much as the ides that a strict young woman whom they don't know is now in charge of them and can embarrass them the way I obviously was doing to Henry."

"I'm so sorry for what he did," Henry's mother replied. "He's not a bad boy but just needs some disciplining to keep him in line. He gets to do pretty much what he wants off at college, I know."

Margaret was intent on making the most of this assignment. Henry's mother had given her his room for the summer and she had moved what she need in there. She knew that Henry's family, although it tended not to show it, was one of the wealthiest in the area, so she wanted to leave this work with a good send-off.

She picked up her handbag and slowly walked upstairs to Henry's new room, the one that had been and essentially still was his sister's.

She walked casually into his room and smiled at Henry.

"I'm sorry we had to start off that way," she said calmly, "and I hope we can get on this summer. Your mother was very concerned about your messiness and your attitude. I'm sorry that you responded the way so many boys do when someone other than their parent spanks them.'

She then explained that she would be inspecting his room every morning after he left for work. She would give him a grade on both the tidiness of his things and the room as well as for his behavior during the time he was home.

"I know it sounds childish to you," she went on, "but I regard it as akin to a report card for a more mature person. This will tell you where you need to improve and where I may have to step in to make sure you do indeed improve. As you should realize, my primary tool for making this happen is your realizing that you will be spanked if you fail to adhere to these rules."

Margaret did not explain to Henry that she was not in the habit of accepting anything less than total positive response to her every command. Being a governess, especially for a college-age boy like Henry, satisfied her deepest impulses of control and dominance.

Henry was still in an embarrassed state but he also was annoyed at the direction this whole matter had taken.

"I still don't know why at my age I need this kind of babyish supervision," he remarked.

Margaret's face darkened for a moment and she said briskly, "Your parents still provide your support and they feel you need this. I'd think more about doing what they want, which isn't a lot, and also learning to grow up so we don't have the kind of thing happen that happened to you down in the living room, and I don't mean the spanking."

Henry's face reddened with renewed embarrassment. The last thing he wanted was to be reminded of his loss of control over Margaret's lap. But it was hard for him. She was attractive and was now in a position to embarrass him just by undressing him in front of her, or anyone else, for that matter.

A call came from downstairs that someone had come by to see Henry. Margaret told him he could go downstairs.

When he arrived, he saw that one of his old friends from high school, with whom he had occasionally gone out on dates, Kathy, a sweet-looking, blondish girl who was also 18, was waiting for him.

"Hi Henry," she grinned. "I heard you were home. Hope we can see some of each other this summer."

"That'll be great, Kath," he said, his mood improved greatly by this visit from a girl he really did like.

But Margaret now appeared and wore a stern look on her face.

"Henry," she said, "you need to finish cleaning up your room and take your shower."

"Who is that woman?" Kathy asked, with a look of complete amazement.

"Oh,..." Henry waffled, "she's been hired by my mother to make the house function better."

"Henry," Margaret now intoned sharply, "you will not dissemble about my role here. Miss..."

"Kathy," the owner of that name filled in the blank.

"Kathy," Margaret repeated with emphasis, "I have been retained as governess to improve the way Henry behaves and attends to his responsibilities here."

Henry now cringed with shame, but worse was to follow.

Kathy was already stupefied at this turn of events.

"I would like for you to remain here for a few moments while I indicate to you what this involves," Margaret went on crisply.

She then beckoned Henry with her finger and he stood in front of her while she again unbuckled his pants and unzipped them, pulling them and his shorts down yet again.

With a surprised and shocked Henry unable to say anything out of fear of embarrassing himself any further, she took him back across her lap as she sat down on a straight chair, and proceeded to spank Henry in front of Kathy as if it were the most normal thing in the world.

The spanking hurt like hell, Henry felt as his brain went into overdrive about how he would survive this, but it was so so much worse getting it in front of Kathy.

Kathy, for her part, was amazed at the proceedings. She really did like Henry and hoped she would be able to spend time with him this summer, but now she started thinking in a different direction.

Maybe she would get to know this incredible woman who was in charge of him and be able to take part in mastering him. She sort of was starting to like the idea of having a boyfriend she could wrap around her little finger...or perhaps place over her lap.

After Margaret finished spanking Henry in front of his friend Kathy, she sent the 19-year-old up to his room to clean it up. She then invited Kathy to sit down in the living room. Henry wondered what this conversation would concern, but he dared not listen in after the new governess, Margaret, had punished him in such an embarrassing way, in front of his friend. He had really had hopes for hitting it off again with Kathy this summer, as they had been quite close in high school.

"You noticed how I took charge of him?" Margaret Ames said to Kathy with a smile.

"Yes, Miss Ames," Kathy responded, slightly fearful herself but anxious to learn what she could about what looked to be quite the unusual situation prevailing in Henry's household.

"You may call me Margaret," that lady said, again smiling. "You look like a nice person and I would like to invite you to work with me on improving Henry's behavior."

Kathy smiled and couldn't restrain herself from showing quite a bit of enthusiasm at being let in on this project.

"Oh, Margaret, I'd be delighted to be involved with you," she gushed. "I really like Henry but it would be amazing to be able to exercise the kind of control you clearly already have established over his conduct."

"I assumed you were a serious young woman, Kathy," Margaret responded, feeling able now to compliment the younger woman. "Perhaps we might go upstairs in a few minutes and inspect Henry's room together? If he hasn't done what he was told to do, I might ask you to be involved in disciplining him."

Kathy felt her panties getting wet at the sheer prospect of disciplining, maybe spanking, this boy she really liked.

She grinned her assent and sat back contented.

After about a half hour had gone by, during which Kathy told Margaret about her own experiences thus far at college, the governess suggested that they pay a visit to Henry's room upstairs.

They walked very quietly upstairs and when they entered the room, which was very girly as it had been the room of Henry's older sister, now off for the summer, they were quite surprised to see Henry lying on the bed and his trousers were down. He was jerking off into a pair of his sister's panties that he had obviously removed from one of the drawers.

"Henry," Margaret said in a firm sharp tone, "is this how you are cleaning your room?"

Henry was devastated to have been discovered in such a shameful posture, made worse by Kathy's presence as a witness. But worse was in store for him.

"Henry, you have misbehaved when you were told what I expected," Margaret went on, scolding him as if he were a naughty child. "I intend to punish you severely. But perhaps it will be best if I ask Kathy to lend a hand, so to speak."

She then handed Kathy a small towel to place on her lap and told Henry to leave his pants down and get across his friend's skirted lap.

Kathy was now faced with Henry's already rosy bare bottom staring up at her. She had never spanked anyone before, much less a boy she wanted to be more than friends with. But she decided that this was her chance to take control of their relationship, so she went on in the direction Margaret had indicated.

"Henry, I'm disappointed that you would go up to your room, especially this sweet girly room that your governess has selected for you to use, and profaned your sister's lingerie so naughtily," Kathy said, trying to act like she had seen a real governess like Margaret act.

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