Henry's Home for the Summer Ch. 05

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Margaret takes on training Kathy's brother.
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Part 5 of the 8 part series

Updated 06/08/2023
Created 04/28/2017
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This is part of a series. It will make more sense if you read the earlier installments, but that is not strictly necessary. The story deals with both female dominance and bodily functions, so if you have problems with either, read no further. All characters are 18 or over.

*****

Margaret Ames, the thirtyish governess whom Henry's parents had hired to keep an eye on him over the summer, was thinking that although she had pretty much taken over the household in that she had already trained Henry to serve her and then asserted her dominance over his well-to-do parents, she might have worked herself out of a job.

Unless the parents really wanted to have her put them through their paces much of the times, which she doubted, there was little reason for her to stay on. Margaret had already done well in her career to date and the governess work was a summer fling for her, indulging her own sexual needs as well as providing a change of pace in her usual hectic business life. It was even better, of course, that she was in control.

She received a phone call while she was ruminating on this and it was from Lenore Hansen, Kathy's mother. Kathy was Henry's girlfriend, and she and Margaret had become fast friends, when Kathy realized that Margaret would include her in the training Henry was undergoing. Kathy was thus trained to dominate her boyfriend. The relationship had become quite intimate quite quickly as a session where Margaret was teaching Kathy how to control Henry became a very intense sexual threesome.

Kathy was a pretty, 19-year-old blonde and Margaret enjoyed the situation, especially since she knew it would not last and no one would feel they had continuing obligations of any kind. What happened ultimately between Henry and Kathy was up to them, Margaret blithely concluded.

Lenore, however, said she had a proposition for Margaret and invited her over for lunch that day. The Hansen home was not far away so Margaret decided to get a bit of exercise for herself, other than using her arm to spank or cane Henry or his parents. She walked over to have lunch with Lenore, whom she recalled meeting once when she had dropped Kathy off at home after a session training Henry.

When Margaret arrived, wearing a variation on her governess outfit, a navy skirt and a white blouse with paisley ascot and gold stickpin atop her usual sheer hose and burgundy pumps, she encountered Lenore in what looked like a collegiate or high school jumper, with a plain white blouse and espadrilles.

The outfit looked a bit juvenile, Margaret thought to herself, but she definitely wasn't going to criticize her hostess. Lenore had her come into the formal dining room and had prepared a lovely salad tray with all kinds of choices. Margaret helped herself to quite a few of them, as did Lenore, and then they looked directly at each other.

"I do appreciate what you have been doing for Kathy," Lenore said. "I do feel that it is good for a young woman to be able to assert herself with men, even boyfriends, or especially boyfriends, these days."

Margaret still held off commenting and thanked Lenore for inviting her over.

"I am having a problem with my son, Robbie, who just turned 18," Lenore went on. "He seems to think he can do exactly what he pleases here and acts like the lord of the manor. I was hoping I might persuade you to take charge of him as you did with Henry. Kathy tells me you've done a wonderful job there and I'd like to see some improvement here."

"From what I hear about him from Kathy," Margaret responded, "I suspect this will be a more challenging task. I gather that your son has had his own way for a long time."

"Yes, alas," Lenore said, "he has, and his father, who is not here much, and I, yes, I accept the responsibility, too, are to blame. Although, please excuse me if I mention that no, I don't want you to take charge of us." She couldn't help blushing in saying that.

Margaret ignored the apology but said she felt this would take some time and she would have to charge accordingly. She also said she'd have to ask Henry's mother if it was all right with her.

Lenore smiled and told her she had already cleared that hurdle. She was good friends with Lucille, and had spoken with her. Lucille had sung Margaret's praises and recommended her to Lenore.

Margaret smiled and when she heard the generous terms that Lenore was proposing, she immediately accepted. She went off with Lenore to check out both the room she would be occupying and the adjoining one in which Lenore's son Robbie was located when home.

****

Robbie arrived home later that afternoon and walked into the house to find the well-dressed Margaret sitting calmly in the living room. He knew who she was because he was somewhat friendly with Henry and had been even before the latter began going out with his sister.

"Hi," he said. "Are you waiting for my mom or my sister?" he asked.

"Neither," she said crisply. "I'm here to speak with you."

"Why?" he asked. "I don't think I need you to do with me what you're doing with Henry."

"Well, your mother thinks I need to," she responded. "So we'd better talk."

"Not interested," he said, and turned to walk upstairs.

"Your room is locked," she said, "and if you want to stay here, you'll sit down, listen, and do what I tell you to do."

"Are you kidding?" he said, but was already getting fearful at the assertiveness of this woman.

"I certainly am not," Margaret said calmly. "You seem to have some growing up to do."

Robbie stopped himself from making a sarcastic remark.

"Really," he said, "did my mother bring you here to take me on as a project?"

"You could put it that way," she said. "Are you ready to cooperate? You will see that it doesn't have to be that painful...although I'm perfectly prepared if indeed that is your choice."

"O.K.," he said skeptically. "I'm game, but are you going to...spank me like a kid?"

"Yes," she answered brightly. "You will be disciplined according to your behavior and that includes how you clean yourself and keep tidy."

Then she stood.

"Stand up and drop your pants," she ordered in a soft tone.

"Do we need to do this?" he asked.

"If you take longer, you will add to your discipline," Margaret rejoined.

Robbie dropped his pants, exposing some tighty-whitey Y-fronts.

"Now pull those down to your knees," Margaret ordered, in a sterner voice.

He complied and she bent down to look at the crotch.

"As I expected, you don't spend much time wiping yourself properly when you use the toilet," she said bluntly.

Now Robbie was embarrassed. Even his mother had never checked his underpants for stains before.

"Turn around and spread your cheeks," she said.

He couldn't believe he was doing this because this woman was telling him to, but he did it.

Margaret peered in between his firm bottom-cheeks and actually inserted a finger slightly into his anus.

She withdrew it and looked at the tell-tale smudge on the tip.

"You are filthy," she said, and sat down on an armless chair.

"Get across my lap," she intoned, and Robbie now was caught up in the pattern she had established that he did not even think to resist.

Once he was across her lap, Margaret reached into her handbag and took out her trusty rectal thermometer. She also had a tube of Vaseline and she took the thermometer, rubbed a dab of Vaseline on it and inserted it slowly into Robbie's bottom-hole.

He had never had anything inserted there before and cried out at the intrusion.

"I'm sure you had your temperature taken this way when you were a child," Margaret said, "and now you will treated like a child until you earn a promotion."

She counted the time in her head and watched her wrist watch. Then she extracted the thermometer and read it. It was normal and she told Robbie that.

"However, we're going to start out with a spanking so you understand what is involved when you do what you're told and what you're supposed to do, and when you don't," she added.

She then began spanking his bottom cheeks alternately. Soon they grew pink and then rosy and finally, as he began complaining and then groaning, red.

Robbie's mind was going a mile a minute and he realized he was way behind keeping up with this woman, who had him by the short hairs figuratively, and soon, he figured, literally.

Once the spanking was finished, Margaret had him stand up.

"For now, "she began, "you will be wearing panties and using a potty for your toilet."

He started to complain about both of those indignities and she shushed him.

"If you don't like that, start behaving the way you're supposed to," she said firmly. "If you don't," she then warned him, "you will be demoted. That means you will be wearing diapers and I will be changing you. First, pull-ups and then regular tape-on diapers. Don't want that? Then do what you're told."

Robbie was sufficiently overwhelmed by all this that he nodded and then made himself say, "Yes, Ma'am."

"That's much better," Margaret smiled. Then she began to ask him about his life. He was free for the summer. Did he have a girlfriend?

It turned out that he didn't but he hung out with a mixed group that included a few girls from school as well as his longtime male friends.

"Do you get it on with any of them?" she asked.

Robbie knew well enough by now not to play games with this woman so he answered truthfully, "Yes, I have sex with two of them now and then."

"Do you take appropriate precautions?" Margaret inquired, ignoring any idea that any topic was off limits.

"They're both on the pill," he answered.

"So you don't use a condom?" she followed up.

"No," he said. "I've known them for quite a while."

"Do they have sex with anyone else, to your knowledge?" she continued.

"I don't think so," he said, but there was a slight doubt in his voice.

"When I allow you to go out," she said, which conveyed a real tone of menace to Robbie, as he began to realize how his life might be restricted from now on, "You will start using appropriate protection when you have sex with them. No ifs, ands, or buts, no pun intended," she grinned.

He grinned in return, recalling in his mind how his girlfriend Sally liked it in the ass.

They now proceeded to his room where Margaret opened a drawer in his bureau and pulled out a pair of pink panties that were his size.

"Put them on," she ordered.

He didn't resist and put on the humiliating garment.

"Be grateful that I'm not dressing you like a schoolgirl," she said, thinking of the jumper his mother had been wearing.

She let him ponder that one, figuring that it would be good for him to imagine himself being made to wear a plaid skirt, a white blouse, cute little socks, and MaryJanes, as well, of course, as a training bra.

"Yes," she added, "if you misbehave, you will be dressed as a schoolgirl."

She had arranged for his supper to be brought up to the room and she sat there while he ate the childish meal. She had had them include things like rice pudding as well as mac'n'cheese and green beans.

Robbie found out what it was like to be put to bed at 6:00 P.M.

He was told that if he needed to go to the bathroom, he was to knock on Margaret's adjoining room but he was not permitted to go by himself yet.

This was the closest he came to putting up a fight but his heart wasn't in it. He had given in so much so far that it didn't make sense and she'd probably just spank him some more and that hurt like hell. He didn't even want to think about what other implements she might use.

He had to knock on Margaret's door once that night. She accompanied him into the bathroom and watched as he peed. She told him to shake his penis and use some tissue to wipe the tip so he didn't stain his panties.

She decided she would not make him sit down to pee...yet. That would be good to keep in reserve in case he needed some firmer discipline.

The next morning she was at breakfast with him, having dressed him in pretty much his normal clothes except for the panties under his sports shorts.

His sister Kathy was at breakfast, and so was his mother. His dad had as usual left already for the office.

"I'm going out this morning for a brief time," Margaret said. "I'm leaving Kathy in charge of you. If you want to avoid being punished, you will do what she says."

Kathy notice how compliant her usually difficult brother was already with the new governess. She longed to be allowed to spank him but realized she had to do exactly what Margaret told her if she wanted to be given that kind of privilege.

When Margaret had left, Kathy told him she had some work to complete in her room but that he would be allowed to watch TV until Margaret returned.

"You better not act like Miss High and Mighty," he muttered to her.

"OK," Kathy said brightly, "that will go down in my little report book. You will be sorry you started up with me, little brother."

He winced, realizing that he would be in for it when Margaret got back.

And so he was. Margaret's face turned sour when she read Kathy's report. She turned to Robbie and told him to drop his trousers and panties.

"Oh please, Miss," he pleaded, "you have to let me get used to her being over me as well as you."

Margaret listened but then called Kathy in. She told them both that Robbie now knew he needed to defer to Kathy's orders as if they were given by her. And then she glanced at Kathy and told her that she assumed he would become accustomed to doing that.

"You will be punished, however," she told Robbie. "I'm putting you under Kathy's supervision for the rest of the day. She will supervise you in the bathroom. Ad as punishment, she will watch as you sit down to do any of your business, including peeing, yes, like a girl. If you behave today, I may relent on that tonight."

Then she told him to bend over the end of the couch. She took her small thin cane out of her handbag and Kathy took a deep breath. She had forgotten how severe Margaret could be.

Margaret stood behind Robbie, lay the cane right across his bare bottom, flicked her wrist and snapped the cane across his bottom. He screamed from surprise as much as the stinging pain, which was major. This was repeated five more times and Robbie, for the first time in his life, had received six of the best.

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