Anna the Nanna

by Tony Tiger

Copyright© 2018 by Tony Tiger

Historical Sex Story: A household helper with secrets influences many lives with her hot body.

Caution: This Historical Sex Story contains strong sexual content, including Ma/Fa   Teenagers   Sharing   Pregnancy   .

Anna was of farm stock. Sturdy, only barely attractive, but dependable and able to corral two early-teen boys. Exactly why she’d held her post as nanny for five years.

This woman of indeterminate age, they guessed in later twenties, was somewhat of a mystery. She was close-mouthed, never speaking of family. One her one day a week off, Sunday, she got on her bicycle Saturday night and rode into town, to reappear promptly early Monday morning.

Geoffrey had turned sixteen and was a good student as well as helpful around the estate. Besides the great house there were several outbuildings set on two hundred twenty acres of mostly tillable land with a few small forest copses. His father was a banker, having inherited the land, so much of it was rented out to tenant farmers who occupied humble dwellings once used as lodging for employed farmhands.

This eldest boy was a curious one and had long wondered where Anna went on her day off. One Saturday evening conditions were right so he followed her at a discreet distance as she pedaled along the lane to the village, about five miles away.

She went to the poorer part of the village and entered the door of a shabby upstairs flat. Continuing down the street he spied a bakery. Purchasing a sweet roll, he asked the baker if he knew an “Anna” who lived nearby. Tradespeople like this knew everyone in their neighborhood. He had to clarify by giving her approximate age.

“You must mean the one who works all week out at that estate in the country.” Geoffrey confirmed that and the man continued, “She lives about six dwellings down on the right with her husband. No children though. She’s usually home come a Saturday night but no doubt she’s ‘catching up’ right now.” He gave a broad wink at the boy.

Geoffrey thanked him with a parting comment, “I’ll stop by another time.” As he pedaled home his mind was busy with how to best use this new information. He wished no ill will towards Anna. She had been good to him and his brother. But there must be some reason she had withheld her marital status from the family.

Then it dawned on him. Something that might be good for both of them that a little blackmail could expedite.

The opportunity appeared when his parents took his younger brother to an event that he was able to beg off from. After Anna served dinner, he said he had some questions that maybe she could help him with. Of course, she would.

Geoffrey had a tutor two days a week beyond his regular school attendance. It was important in the society of that era to know at least one European language and he was learning French. He had an aptitude and had gained some proficiency in both the written and spoken forms of the language. He enjoyed reading books in his father’s library and happened upon an erotic novel somewhat hidden. It was fascinating since his parents had never mentioned the subject to him.

This was the nature of the questions the adolescent had for the married woman. Keeping a mutual confidence was very important and gave him the leverage he thought he needed.

“Miss Anna,” as he addressed her since he was always respectful, “I have been reading about sex and have some questions that a married woman, like yourself, might be able to answer.”

She turned white and a fearful expression covered her face, “How do you know that?”

“Never mind how. I will keep the knowledge private if you will assist me.” Geoffrey said in as reassuring a tone as he could muster. When she nodded with eyes downcast, he thought “It is working!”

He had carefully selected some passages in the book which began with simple issues of terminology. She did not have all the answers but was trying to be helpful. He upped the game with anatomical questions and seemed befuddled by the verbal answers. Then he suggested that actually seeing the parts in question would be the most helpful.

Anna objected, “I can’t show you my private parts. You are not my husband.”

Geoffrey had thought through likely objections at this stage and had a ready answer. “Of course I’m not, but this is for education. Many women have removed their clothes for artists without shame. Is this not equally noble?”

She could find no argument and began by removing her blouse and undershirt. Brassieres were not widespread among the lower classes. As he visually examined her firm and nicely rounded bosom, he asked questions, culminating in the desire to know the texture. She acquiesces, getting a bit of pleasure out of the exercise already. Only her husband had ever seen this much or touched them.

When he poked and then squeezed her mammaries, the nipples firmed up and protruded. She explained that was a sign of sexual arousal, or of cold temperatures. Geoffrey knew it was warm in the room so filed what was happening away for later use. He finished the session, not wanting to go too far too fast, by talking about nature’s function for breasts. Could he feel what it was like to nurse on them as was described in the book he was reading? By this time, Anna was enjoying the activities a lot more than just as a teacher so she encouraged him. His alternate sucking and nibbling of her aroused nipples caused the flood of pleasure that she rarely got with her husband. She could smell her crotch and hoped the young pupil wouldn’t notice. It needed to be dried out after she left him.

Geoffrey was delighted and had an excellent masturbation as soon as he was alone. He began planning for the next “lesson” when the opportunity was next presented.

In the meantime, he found opportunities to inquire more about her situation. It seems her husband was a farm foreman but was seriously injured in a work accident, leaving him able to walk only with assistance. She took this job as the best paying one available but hid her marital status since it was usually single girls who were so employed. Her husband had a woman come in to cook and do basic stuff while she was gone.

He had learned to be a clockmaker and had a part time job very close to where they lived. It paid enough to cover his care-woman.

Once again his parents and brother were gone for an afternoon. When Anna’s main chores were done, Geoffrey asked for her attention. He was so polite, and she had enjoyed the previous encounter so much, that she looked forward to this time together.

Translating from the book, the lower parts of the female were the subject of questions. Less shy this time, Anna removed her skirt and petticoat, leaving her blouse on. This was a “class” after all. Sitting down, she pointed out and named the parts. The place where pee came out was easy, as was the “birth canal”, but the clitoris seemed to confuse the young scholar. In mild frustration, she took his hand and moved it to stimulate her part, explaining that this felt extremely good and to watch as she orgasmed.

He was fascinated and looked for a discharge as it happened. His trousers were tented and she remarked that this was the big difference between a man and a woman. He acted puzzled so she told him to open his pants and let that stiff organ be free. Inwardly he was absolutely delighted.

Grabbing a nearby cloth to catch the eruption, she rubbed his erection until it spurted. He moaned and almost couldn’t stand up, this climax so much stronger than the self-inflicted ones. He hadn’t expected that!

She was smiling, thinking she had taught him about masturbation. What she HAD taught him was that having a woman cause one was SO much better. They sat together with parts exposed for a while. He was on a roll and translated a paragraph about oral sex. Anna blushed. She didn’t even admit to other women that she and her husband often used this form of sex because of his crippled condition. Women were supposed to abhor that kind of pleasure unless you were a whore, even though it was often done by even the highest class wives and mistresses.

Anna had to absorb what had already happened and demurred, saying it was a subject for another time. Geoffrey noted that she had NOT refused. Wonderful! More anticipation to masturbate to.

It was two weeks before another time presented itself. Anna thought about her young charge each time she was enjoying her husband orally or the rare vaginal intromission. Her spouse was good at cunnilingus and she shivered thinking of a strong young tongue possibly exploring her nether regions.

Her “proper” reluctance faded quickly as she assumed the role of instructor again and her student was very eager and compliant. It was delightful to be in charge since she was usually the one taking the orders. It was thrilling to look up at his rapturous face as his lovely hard organ discharged into her mouth, then transitioning to his lingual questing at her crotch. The wickedness of it multiplied the pleasure and she orgasmed strongly, trapping his head between her strong thighs.

She was profusely thanked and offered money. She was indignant, “I am NOT a trollop! I do this for you as my charge, not for monetary reward.” While it was not the whole truth, since it was meeting an unrequited need between visits to her husband, he apologized.

Anna knew where this was headed. Being little educated, she was still plenty street-smart. Her husband was rarely able to perform intercourse with his lower half being so poorly functional. With their limited sexual experience, the standard position and the way animals did it were the only ones they could conceive of. He knew that she felt shortchanged by the low frequency of penetration. His libido was low as well so he was receptive to the carefully proposal Anna made. She presented it as a teaching service being part of her role as nanny. That was sufficient rationalization for both of them. Her husband did not feel the least bit threatened by the much younger man.

So it was that feigning reluctance, the older married woman proceeded without undue delay to the intromission of a young phallus into her genitalia as the final lesson of the series. Because both enjoyed the encounter so much, and supported by her own husband’s permission, it was decided that regular and frequent practice was necessary for proficiency.

To put it in a more commonplace expression, they wanted to fuck each other senseless as often as possible. Finding opportunities was a challenge, but rarely more than three days went by when it was not accomplished, even if briefly.

The first time since conjugation began with Geoffrey that she had a day off, she was seeded just before riding home to her husband. When he was informed of that he was offered to taste her as she was or after a bath. He chose not to wait and she regaled him with her stories of the week. The tail-telling was interrupted by her mouth full of a spousal shaft spewing semen.

In subsequent weeks, the new copulators worked their way through the French book. They discovered other positions of congress. Anna was delighted to tell her youthful stud how certain ones could be used with her husband. He would be most appreciative. That thought of another hard shaft spewing cream into his first woman, even though it had undoubtedly done so many times in the past, was even more stimulating to Geoffrey.

Her husband repeatedly told her what a blessing it was that she was learning so much about an essential life activity. The look on his face when she positioned herself in woman-astride, both facing him and away, was like a second release of virginity. He could also spoon with her and loved to be embedded without even trying to ejaculate.

The following Monday, when they snuck away to the cellar and he quickly embedded himself in that honey hole, she gleefully said she had ridden her husband to a great outflowing of seed just that morning before returning. That thought, and the feelings of a slipperiness not from his own spend, set him off quickly and profusely. Anna complained that her men were SO messy! But she said it with a smile, being proud to elicit such responses.

Geoffrey was concerned about this loving woman’s life condition, often on the edge of financial failure. Knowing her husband’s experience, and checking to find excellent references to his skills, Geoffrey researched a proposal that they directly farm the best land instead of the mediocre return they got from the rentals. He did not want to be a banker, loving the land too much to spend all that time in the city.

His father was impressed with the business plan presented to him by his own offspring and suggested several additions and changes. They would give it a try on twenty of the two hundred acres they owned. Anna and her husband, Harold, would occupy the disused foreman’s cottage and a small pony cart was purchased so he could get around as he needed to.

When this was revealed, Anna nearly raped Geoffrey on the spot, she was so grateful. When she got him alone later he was dazed at her vigor. She was forever his on request.

This was a very different kind of farming. Instead of the traditional and low profit row crops, they would produce quality vegetables in quantity for inn and home. Town markets were the ordinary source for those foodstuffs produced on small plots. This plan would provide larger quantities of a few items at first. Hardy plants such as cauliflower and broccoli were chosen, as well as tomatoes. Another innovation was irrigation for the tomatoes if needed.

This was labor intensive but Geoffrey had figured that five men and five women could be hired locally at a reasonable wage. The men would do the more strenuous work while the women attended to detail. Anna and Harold could identify people who were reliable.

Although his father noticed that Geoffrey spent some time sequestered at the cottage, usually at the end of the day, but sometimes at the beginning, or both, he ascribed that to planning and/or management meetings. It was more like planting as the young man unleashed volley after volley of seed into Anna’s appreciative “garden”. He minded not that she might have her furrow recently prepared by her spousal planter.


Almost two years passed and the super-garden was producing more profit than all the rest of the farm combined. Geoffrey had quarters for the farmhands built next to the cottage with an office and sleeping space for himself included. Productivity noticeably increased with the workers having better housing and able to spend less energy and time travelling to and from the farm. Some were married couples so volunteers to show appreciation to Geoffrey were not lacking during Anna’s monthly. She remained his clear favorite though. Harold just waited it out, being much less horny than the younger man.

Geoffrey’s younger brother was approaching his sixteenth birthday when Anna was presented with a request to deflower him as a special gift. The boys’ mother, possessing a woman’s perception, had figured out her eldest son’s true relationship with the nanny and had confirmed it with the woman. She was pleased that he was spending no energy with the silly and greedy girls his age. It was she that proposed that way of initiation into manhood for Richard.

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