Henry’s Home for the Summer Ch. 03

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Arianna Sinn

This is part of a series. It will make more sense if you read the earlier chapters. There is some reference to bodily functions, so if that offends you, read no further. This story also relates to female domination, so if that bothers you, I’d also suggest you skip this story. All characters are 18 years old or older.


Henry, who was 18 and home for the summer from college, became accustomed to having to submit to the governess his mother had retained to supervise him for the summer, Margaret Ames, an attractive young woman in her 30s who was experienced in supervising boys. She was responsible for him when he returned from work and in the morning before he left.

This was a pleasant job for Margaret because she had her days to herself, as Henry’s parents were well-off and there was plenty of household help, so Margaret was not asked to do anything around the home. She had been given Henry’s room and he was ensconced in his older sister’s room, she being away in Europe for the summer. Henry was still wondering about his sister’s clothes that were in the drawers and closet in his room, as they seemed large, as if they had been altered to fit him rather than his sister.

Margaret was making him wear panties under his suit and now his girlfriend Kathy had inserted a butt plug in his anus to prepare him for when she was going to try out her strap-on.

He enjoyed his work at an investment banking house where his father had arranged a summer job for him. Henry was outgoing and bright, so the staff there liked him and did not resent his presence, knowing of course that he was just there for the summer. However, he had impressed his supervisor and the others in higher positions, so it was likely he would be offered a permanent job. The bankers also liked the idea of having a relationship with someone close to Henry’s father, someone who could offer them plenty of opportunity to attract his father’s investment, should Henry decide to go with them.

Henry returned home as usual and Margaret had him submit to a panty inspection in his room. She told him to drop his trousers and lower his panties. She was training Henry to prepare himself for this daily inspection by having him turn the gusset of his panties out for her to scrutinize for stains.

Henry now had learned that if he wiped himself carefully when he used the toilet, and made sure he had shaken his penis after pissing, his panties would pass inspection by the governess. Margaret had become friendlier, he noticed, and he wondered if she actually was attracted to him.

Margaret bent over to look at his panties and found them fine. Henry had had a look then down her cleavage and saw that she was reasonably well-endowed and liked to wear clingy tops that showed off her bust. He was developing an attraction for her, although he didn’t want to push it for fear of her spanking him and also because he was very fond of his girlfriend Kathy.

Margaret had allowed Kathy to spank him but now things had been resolved between Henry and Kathy, and they had an understanding. Kathy had told him to tell Margaret why he was wearing the butt plug she had inserted ataşehir escort bayan in his bottom.

When he did just that, Margaret’s face actually reddened a bit in embarrassment, which was surprising given her own somewhat unusual interests that had led her to become a governess. She told Henry to follow her into the bathroom that was between his room and hers. He wondered what this was all about but did what he was told.

When they arrived in the bathroom, Margaret rather unceremoniously rucked up her skirt and pulled down her own panties, which, Henry observed, were bright yellow, and sat on the toilet. Soon as he watched her in some fascination, for she had a nice-looking, trimmed bush of auburn pubes above her lovely-looking slit, and she released a long pee stream that Henry could hear but not see as it hit the toilet bowl water.

He was then a bit surprised to hear her release what must have been a fairly sizeable bowel movement but he did immediately sense the smell of her shit. Margaret then turned around and Henry could see her cute bottom as she held her bottom cheeks open and told Henry she wanted him to lick her clean back there.

Henry was somewhat repelled but fascinated by Margaret’s showing him her cunt and her asshole, even if it meant he had to lick the latter instead of the former, which he would have enjoyed. He bent down and knelt before her on the floor and proceeded to lick her acrid-tasting asshole which had only faint traces of shit around it. She told him to get his tongue inside and then he tasted what he assumed was some of her movement.

“You’ve done that quite nicely, Henry,” she said, as she turned back round on the toilet seat. “I’m going to let you lick me in front now and if you bring me off, you will be rewarded appropriately.”

He now sensed that Margaret was hot to trot and that he might even get to fuck his governess if he played his cards right. She asked him how he had enjoyed his date with Kathy the night before and he smiled and said he liked Kathy a lot and they had talked and had a very nice evening.

“But you fucked her, didn’t you?” Margaret said quite bluntly. He was again surprised to hear her use that word but he answered, “Yes, we did have sex and it was really nice.”

Henry’s parents were out for the evening and all the house staff had gone home for the day. Margaret knew the house was empty except for them so she told Henry to come into her room, which, of course, had been his room.

She instructed him in how to unbutton her blouse and unzip her skirt. Then she turned so he could unhook her bra and he saw her very nice 36C tits which she invited him to suck. He did that and looked up lovingly into her face.

Margaret was now in her panties and she told him to take off all his clothes. He did that and she told him to lie on the bed on his stomach. Once he did that, she reached between his cheeks and took out the butt plug. It was a bit dirty so she put it down in the corner on the floor.

Now she lay down beside him and held her arms open for him to hold her. He enjoyed the feeling of holding her in his arms and pressing escort kadıköy against her tits. She was a nice-sized, curvy woman in her 30s and it made Henry feel much more mature to be close like this to his governess rather than be spanked by her.

She lay back, held her lovely legs open and told Henry he could get between them and lick her split. He started and liked the taste of her secretions, as her vagina was obviously flowing aplenty.

Soon she began to move her hips and she began making small moans. She looked into Henry’s eyes, took his head up to her face and kissed him deeply. Then she whispered to him to put his cock in her right then and there.

He did and began to thrust, enjoying most the idea that he was actually fucking his governess. Margaret had not had sex for a while so she enjoyed the feeling of a large cock in her cunt. Henry made his hard-on last. He thrust and pulled out then plunged back into her honeypot.

This was a real experience and he found fucking Margaret much more exciting than even the nice sex he had had last night at Kathy’s house. He couldn’t believe that he had actually had to lick Margaret’s dirty asshole.

Soon they both reached a climactic moment and Henry spurted strongly deep into Margaret’s vagina. She relaxed as his erection softened. Then she told him she was going to dress him that night in his sister’s clothes, which had been altered to fit him by his mother. She took out a cute padded bra and a new pair of matching lilac panties which he was told to put on.

Then she found a nice navy skirt with an elastic waist and a plain white top, which he put on over the bra and panties. Now Margaret handed him sheer hose which she showed him how to roll and slip on his legs. Finally, she retrieved a pair of burgundy pumps.

She had Henry sit down in front of his sister’s dressing table as she made up his face and fixed his hair as best she could into a sort of pageboy. No sooner was Henry cross-dressed than the bedroom door opened and Kathy appeared.

She giggled when she saw Henry and then turned serious.

“You just went ahead and fucked her, didn’t you, you whore?” she accused Henry, who was her boyfriend.

“Yes…but,” Henry stammered.

“Don’t ‘yes, but’ me!” Kathy said firmly and with some anger. “You are going to be punished.”

Margaret looked on, somewhat taken aback and not in a position to say anything as Kathy took out a small cane from her handbag.

“You’re getting the cane, you bad boy,” Kathy intoned to Henry.

Margaret had thrown a towel around her as she emerged from the bed where she had just been fucked by Henry.

Kathy told her to lose the towel and sit right down next to her.

Then she made Henry bend over the edge of the bed and hold his bottom cheeks open.

“That way I can see your naughty asshole,” she said. Then she ordered Margaret to stand next to him, and hold the same position, with her cheeks held apart.

Kathy came behind them with her cane and started applying crisp stroked to each white bottom. Both cried out as each stroke was strong and stung.

“You maltepe escort two started without me,” she proclaimed.

She gave each of them four more strokes across the middle and base of their bottoms.

Then she told Henry she hoped he was ready to please her and she pulled up her skirt, pulled down her red panties, and lay back on the bed, beckoning him with her finger to lick her blonde-haired pubic area.

Henry succeeded in arousing her immediately and she enjoyed several orgasms quickly. Then she looked at Margaret and turned over so her pert bottom was spread. She grinned at Margaret and used the governess’s favorite finger motion to beckon her.

“You know what I want, darling,” Kathy purred and watched as Margaret dropped her towel and all nude, bent over to lick Kathy’s cute bottom-hole.

Henry was amazed by all of this. Little had he thought that his dominating governess would be put into the ignominious position of licking his girlfriend’s asshole.

Kathy loved every second of it and when Margaret had brought her to yet another wonderful cum, she kissed her on her lips and held her in her arms and the two drew together so that their breasts were pressing against one another.

Margaret looked a bit wan and gave Henry a signal to take her place with Kathy.

Kathy smiled a sweet, glorious smile and lay back and pointed down to between her legs, inviting Henry to make love to her while Margaret watched them.

Henry was really not used to this kind of threesome. He found himself thrusting now inside Kathy’s warm vagina and holding her tight in his arms. Margaret had come over to lie next to them and she alternated between teasing Kathy’s clit with her fingers and teasing Henry under his balls as he moved his cock in and out of Kathy’s engaging cunt.

Kathy suddenly shouted out her happiness as she felt Henry’s cock explode deep inside her while she herself had her greatest orgasm of the whole time.

Soon they all lay together on Margaret’s bed and then moved into the much-used bathroom where Henry adjusted the shower for the women and then joined them as each washed each other’s genitals. The women’s vaginas were flowing plentifully from the intercourse that had occurred and Henry’s cock was layered with feminine juices.

Each lovingly soaped the others and then rinsed them off. When they were toweled dry, Kathy and Margaret together selected some lovely beige panties for Henry and told him to model them for them to see. Kathy then had Henry get up on all fours on the bed and spread his cheeks as she re-inserted Henry’s butt plug and invited him to put hers back into her anal opening.

He found himself staring at her lovely little anal opening winking at him as he gently slid the slim plug back into her dark pink hole between her alabaster bottom cheeks.

Margaret giggled at their matching plugs until Kathy donned a strap-on, quite a large one, she had in her handbag and asked Margaret if she’d like to see how it felt. Margaret told her she’d love having it in her cunt while Kathy fucked her with it.

Kathy had her lie back, lewdly open her legs and hold her thin labia apart, then mounted Margaret and plunged the strap-on, all ten inches, into Margaret’s apparently commodious cunt. Henry watched, as he observed goings-on his first year at college had hardly prepared him for.

This really was going to be quite a summer, he thought.

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