This story is part of a series. It will make more sense if you read the earlier chapters. If you are offended by bodily functions or female domination, please read no further. Everyone in the story is 18 or over.
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Henry woke up the next morning after the get-together with Kathy and Margaret ready to go to the office and wondering what might happen next. It was quite an exciting evening to have had sex with both his girlfriend and the young woman who had been hired to be his governess.
Margaret had come into his room while he was dressing that morning and left him a pair of tiny red panties to wear that day. He was hoping that as promised, she would let up on making him wear panties in another day or so. He put on a conservative suit to go to the investment bank where his dad had set him up with a summer job and enjoyed himself as usual. The others there were not threatened by him because he was a summer employee so they seemed to enjoy his easy humor and willingness to work.
When he came home that day, his parents had gone out for the night, which was common, since his father and mother kept a busy social schedule in their set. Margaret had arranged for a light supper for the two of them and then she invited him again to join her in her room, which had been his room.
She told him that Kathy had called and asked to stop by soon after dinner which brightened Henry's spirits. He was fond of his blonde girlfriend, who had shown her moxie by taking on Margaret. The governess, while in her 30s, had been awed by the audacity of Kathy, whom Henry had not recalled as showing such as strongly dominant side. He figured Margaret had gotten more than she had planned for and was now showing her own submissiveness.
Soon Kathy joined them and the three all cuddled on Margaret's ample bed and everyone took their clothes off. Kathy commented on Henry's red panties, and Margaret answered that he now no longer needed to wear them daily.
Kathy grinned and said that his initiation was just beginning.
She put on a minimal harness and inserted a sizeable dildo into the slot on the harness. Then she had Henry get up on the bed on all fours and hold his cheeks open while Margaret prepared him by rubbing some lube around his tight little anal opening and then inserting her lubed finger into his hole.
Henry liked that feeling of her finger massaging his prostate inside his anal opening. Then Kathy came over with her own lubed dildo protruding naughtily from her harnessed crotch (she had picked a double that extended deep into her own vagina too). She placed the tip right up against Henry's anus and softly let it pass through his anal ring as she slowly eased his sphincter to allow her entry.
Henry had been wearing the thin buttplug that Kathy had inserted in his anal cavity but now he was learning what it was like to be filled. It did stimulate his prostate even more and he felt himself getting hard. Kathy began moving her dildo in and out of him, always slowly and gently. Henry was amazedβin a weird way he realized, once he had gotten past the pain he had experienced when the thick dildo first penetrated his rectum, he was learning what he had figured only girls ever knew: what it was like to be fucked.
Margaret had crawled round so that now she was next to him with open arms and legs and as she embraced him, she also tugged on his erect cock. Finally she positioned herself so that Henry could proceed to enter her waiting vagina and engage in some nice sex with the governess while his girlfriend kept fucking him in his ass.
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Later that day, Margaret was relaxing in the living room when Henry's father appeared home a bit early from his office. He smiled at Margaret and asked her how she was enjoying herself.
Recalling how Henry's mother had commented on his father's sloppiness in terms of wiping himself as evidenced by the skid marks in his undershorts, combined with how she had so readily submitted to Margaret's dominance, the young governess decided to test these waters.
She smiled at Henry's father, whose name was Edward, and said that Henry's behavior had improved significantly. Then while continuing to smile affectionately at the confident businessman who was about 50 and in good shape, she commented that she had understood from Henry's mother that Edward had been negligent in keeping his underwear clean.
Edward almost involuntarily cringed and his face reddened. He was not accustomed to being criticized at all, and for his personal hygiene habits to be so directly criticized by this attractive and clearly assertive young woman took him by surprise. It did, however, appeal to his desire to be taken in hand by just such a woman. He himself had been subjected to a governess's control when he was a young boy. Immediately his mind was transported back to those days when Miss Denton had ruled his life.
Gazing at Margaret, he recalled how he was unable to look Miss Denton in the eye. She was merciless, he remembered now. She spanked him and put him to bed early as punishment. And when he got in trouble for sneaking into his sister's panty drawer, she made him wear a bra and red panties for several days. He had fantasized about Miss Denton's lingerie, not that she ever let him get the slightest glimpse of her undergarments.
"Oh," he responded in an attempt to deal with this inquiry in an off-handed manner, "I suppose I don't always take the time to be as tidy as I might."
Margaret made a tsk-tsk sound and Edward found himself incredibly excited by her dominant tone.
She noticed his reaction and also the bulge in his suit trousers.
"I think I see indications"βshe lowered her eyes to focus on his crotch, making him aware she had seen his bulgeβ"that you may need some supervision," she said firmly.
"You know," he said calmly, giving away the story he had kept to himself for so long, "I did have a governess for a time when I was young."