The tale I am about to relate was told to me by a dear friend of mine. I had known her for about twenty eight years when she came to me with her story. I shall call her Nancy, which of course, is not her real name. Over the years she has shared many of her thoughts and troubles with me, and she certainly had plenty to share. A husband, whom I shall call Kevin, is an alcoholic and transvestite. He cannot perform sexually unless he is dressed in female clothes, and try as she might, Nancy can’t cope with this.
This ceased to be a problem, at least in one respect, when Kevin about five years into their marriage gave up all sexual activity with Nancy. This however left Nancy with the problem of what to do about her own sexual needs. Nancy is a person with a strong sexual drive, and one way of overcoming her difficulty was via a series of lovers.
Of course, Nancy could have got out of the relationship, but she tried to hang on for the sake of the two children Kevin had managed to sire on her in the early years of their marriage. At the time of the episode that she related to me and which I shall shortly pass on to you, Nancy was in her early fifties; she had been married twenty nine years, and there were by then grandchildren also to be considered.
In addition, Nancy felt sorry for Kevin and believed he would fall apart completely if she left him. So the marriage dragged on and Nancy adopted a strategy that, alongside her lovers, gave her some relief from the pressures of home life; she went house sitting for people going on vacation, and included in this was taking care of pets.
It was through house sitting that she came to take on a more profound role in one household. She house sat for a husband and wife, let us call them Dan and Vera, who are both lawyers. This marriage too, was almost on the rocks, but it did manage to produce “The Twins.” They were somewhat disconcertingly named, “Robert” and “Roberta”.
The busy work and social life style of this legal couple meant that Nancy was often called upon to baby sit the twins. This began very soon after they were born and Nancy came to play an extremely important part in the lives of the children. In fact, she became something of a substitute mother.
When the twins were around three years old their parents’ marriage finally broke up. This came about because Vera came home unexpectedly to find her husband in bed with her best friend. Dan departed the house to live with the best friend and Nancy came to play an even more important part in the lives of the twins.
Then Vera took on lovers herself, and this often meant trips away with her paramours, some extending over two or three weeks. Dan and Vera provided liberally for the children as far as money was concerned, but were too busy with their work and amatory affairs to provide the sort of love and nurturing that the children needed. I should point out that Dan’s extensive love affairs did not cease once he moved in with the “best friend.”
So Nancy was frequently shuttling back and forth between her own home, and the home of the twins, leaving the inebriated Kevin to manage on his own for a while.
That Nancy was deeply fond of the twins was undoubted. She is a very affectionate and loving person anyway. It was equally certain that the twins loved Nancy.
The years went by, as they tend to do, and it was when the twins entered their teenage years that a shift in their relationships with Nancy took place. This was initially most marked in Roberta. She became extremely petulant, insolent and contrary.
Oddly, the promiscuous parents of Roberta were very determined that their daughter remain virgo intacta. Roberta, on the other hand, had an equal determination to sacrifice her maidenhead at the earliest possible moment. Thus when Nancy took over the household during Vera’s amorous absences, she had the burdensome task of trying to restrain Roberta from sneaking out of the house on a boy hunt.
Robert, who knew of his sisters sexual activities, referred to her as a “slut” who was having it off with every boy in the neighbourhood. No doubt this was something of an exaggeration, but it did put a great deal of worrisome responsibility on Nancy’s shoulders. One might add the thought, “Woe to the parents who prize too highly their daughter’s virginity, the girl will always find a way of disposing of it.”
Finally Nancy spoke frankly to Vera, saying she could no longer cope with Roberta. The result was, that during those times Nancy was house sitting for her and, let’s face it, still sitting the now seventeen year old twins, Roberta, spitting, hissing and snarling like an infuriated tigress, was removed from the house to stay with a draconian aunt.
This left Nancy with the house and Robert to look after.
Robert was passing through his teenage years in a manner very different from Roberta. He tended to be shy and introspective and, having failed to get the love and affection he needed from his mother, he drew even closer to Nancy.
Another divergence from the Roberta life style was that as far as Nancy could tell Robert was still a virgin. He did not seem to associate with girls or for that matter not much with boys, and the reason for this puzzled Nancy considerably. I have met the twins and their parents, and both the children have inherited their parent’s good looks. If anything, Robert seems to favour his mother’s blond hair and brown eyed features.
Now I should point out that, for all the difficulties that had beset Nancy in her life, she always looked at least fifteen years younger than she actually was. She has auburn hair, always worn long and, one must admit, now regularly dyed; she looks out at the world with very tender blue eyes; her wide mouth with full lips always ready to smile; and a slim figure with breasts, despite her earlier breast feeding, still nicely firm. In short, a very presentable and desirable lady, as witness her rather intricate sexual affairs.
She had a habit, and for all I know probably still does have, of dispensing with bras and panties when at home in hot weather, and home included when she was house sitting. The movement of her breasts beneath a soft shirt or dress, and the obvious outline of sweet little nipples, left little to the lascivious imagination.
I mention this because I don’t want you to have the impression that Nancy was like some of those Nannies you can see portrayed in films or on television; rather stern and unattractive. Nancy was far from such an image.
I have by implication suggested that Nancy was a Nanny, and of course she was really. The twins called her “Nan,” and that is why I have adopted the pseudonym of Nancy for her.
So it was when Nancy was in her early fifties, and looking in her mid thirties, that she came to me and told of her – what shall I call it? – “Her dilemma”? She seems to come to me with all her marital and love-life problems. I suppose I must have a sympathetic manner.
The dilemma began when Nancy was called upon to house sit for Vera once again. At that time the twins were eighteen years old, and Nancy felt that they were past the age when they needed “baby sitting,” and since Roberta would be carted off to the draconian aunt, she said to Vera, “Surely Robert could look after himself.”
You must understand that Nancy was not attempting to reject the task; on the contrary, she knew she would miss it badly, especially where her beloved Robert was concerned. But Nancy had a conscience about being paid for a job she did not feel warranted the money.
Vera protested along the lines that Robert would not eat properly and the house would get into a dreadful mess. Nancy mentally shrugged, thinking that if mother didn’t mind paying up, why should she worry about taking the money?
So Nancy moved in with Robert for a three weeks stint while Vera and her latest lover took off for distant lands and long sessions in bed.
Nothing untoward happened for the first couple of days, except that Robert seemed to be more affectionate than ever, and rather dejected. Looking, as she did, upon Robert almost as her own child, or even grandchild that he could virtually have been given her age, she tried to discover what ailed him.
His response to her early queries about what was troubling him was, “Oh, nothing really.” Nancy, having some understanding of boys that age and the moods they go through, did not pursue the matter, hoping the mood would pass. However, it did not pass, and it was during the evening of the third day of her stay that things came to a head.
It was Robert’s habit that, when he had completed any study projects he had to do, he joined Nancy in the lounge in the evening. It was also his habit, and for that matter Nancy’s habit, for them to cuddle up on the couch. Nancy is a very tactile person generally, and she had cuddled up with the twins since they were babies. Roberta, of course, had long renounced such “silly” ways, no doubt getting her cuddles and lot a more elsewhere.
Robert, on the other hand had, in recent years seemed to want more hugging than ever, and took any opportunity to touch and embrace Nancy.
Nancy accepted Robert’s hugs that evening but she expected that they would eventually lead up to a revelation of what was troubling Robert. Hugs with Robert had often before been the time when he talked about things that were troubling or concerning him.
On the evening in question Robert had his head lying between Nancy’s breasts, and she noticed that his lips were very close to one of her nipples. This was nothing unusual because Robert had lain against her, his head in that position, many times. Additionally Nancy confessed to herself and me that now Robert was no longer a child, but a young man, it was rather delightful to have his head lying between her breasts.
Nevertheless, Nancy was a bit disconcerted partly because Robert’s lips were very close to her nipple, and partly because she was having one of what she called her “liberation days”, being free of bras, panties and wearing one of her more loose and filmy dresses. She also noticed that Robert’s hands were rather restless, and seemed to be wandering over her body.
For a long time they lay together and when eventually Robert spoke he asked what seemed an innocent enough question.
“Nan, you’ve been like a mother to Roberta and me ever since we were babies, haven’t you?”
“Well, I’ve had a lot to do with you.”
“I think you love us a lot, Nan.”
“Yes, of course I do.”
“Yes. She doesn’t seem to want my love these days, but that doesn’t mean I can’t love her.”
“I want your love, Nan.”
“I know you do, darling.”
There was a long pause as Nancy waited to find out what was coming next, then:
“Nan, when we were little you used to bath us, didn’t you?”
“Quite often, yes.”
“Did you wash my co…er…penis?”
“Of course I did.”
“Did you mind doing that?”
“Well no…I didn’t mind.”
“It was very small then wasn’t it?”
“Yes, quite small.”
There was another long pause until Robert, apparently having decided to be bold, said a trifle breathlessly, “It’s huge now; you’d be surprised how much it’s grown, Nan.”
Nan being well aware of the male propensity to boast about the size of their sexual organ or feel inferior if they thought it undersized, responded diplomatically, “I don’t know about being surprised, it’s what I’d expect to have happened.”
“But Nan, it really is huge.”
Those lips had got even closer to Nan’s nipple and Roberts hand was stroking her thigh.
“Is it, darling,” Nan said, wondering where all this was leading.
“I wish you washed it for me now.”
Nan attempted a not very convincing chuckle; “I’m sure you can manage that yourself now, darling.”
“Yes, but it’s not the same, is it?”
At this point there came to mind some conversations Nancy had had with Dan. Over the years he had made several unsuccessful attempts to seduce Nancy, and as she had said to me, “It’s not that I don’t fancy him, but I’m not going to risk losing the work. If Vera found out I was having it off with her ex-husband, I’d be out on my ear.”
The specific conversations had concerned Robert and Roberta’s sexual welfare. As I have said, while both parents were concerned to keep Roberta’s virginity in tact, his father at least was more concerned that Robert should lose his.
“He needs to experience a woman, preferably an older woman at first,” Dan had said several times. His mother had never confided her wishes on this subject to Nancy.
As if casually the father had one day asked Nancy, “Do you know why so many of those boys that had nannies are so fond of them?”
“I suppose because they’ve had such close contact with them.”
He laughed; “Yes, and a bit more than that, Nancy.”
“They masturbated them when they were teenagers.”
“What!” I…I don’t believe you.”
“It’s true,” he chortled, “Some of them even had sex with the boys if the boys showed any interest.”
“You’re having me on!”
“I’m not. I know fellows who had nannies and they admit they screwed them. It was supposed to keep the boys happy and discouraged them from getting mixed up with the wrong sort of girls until they got married or something like that. Of course,” added Dan craftily, “They got paid something extra for their trouble.”
Nancy had rapidly changed the direction of the conversation. Dan’s drift was all too clear; Nancy was supposed to keep Robert “happy” and would get a bonus for doing so.
Now, with Robert suggesting that he would like her to wash his penis, she had little doubt that Dan had been having a “fatherly talk” with Robert. What the boy really wanted was for her to masturbate him.
Having had plenty of lovers Nancy was wise in the way of males, so she looked down at Robert’s groin and saw there a considerable bulge.
“My God,” she thought, “he may be telling the truth about his penis being huge.”
Robert’s hand had moved up her thigh until it rested on her mons.
“I wish you could see my penis,” he said, “You’d be able to tell me if it’s too big.”
Nancy, a woman easily sexually aroused, began to experience the first shivers of libidinous desire. She felt her vagina beginning to lubricate and her nipples starting to harden and extend.
She tried to overcome her heating emotions and said, “I’m sure it’s not too big, darling.”
His voice now muffled as his lips, now pressed right against her ripe nipple, he said, “Let me show you, Nan.”
Nancy was confused. She had an overwhelming desire to see this apparently oversized male organ, but at the same time felt she should stop the direction in which they seemed to be heading despite Dan’s obvious invitation for Nancy to service his son. Finally curiosity got the better of her and she said hesitantly, “All right, if it’s that important to you, darling.”
Robert’s hand went down to his groin and undid his zip and the liberated penis reared up.
Nancy’s first reaction was one of disbelief at what she was seeing. She had seen many male organs before but never one this size. The long light brown shaft with its purplish head seemed painfully engorged with blood. Nancy began to quiver uncontrollably as images of that great organ entering her vagina flowed hotly through her head.
“Is it very big?” asked Robert.
“Well, darling,” quavered Nancy, “It…it…it is large, yes…very large.”
“Would you like to touch it?”
Fascinated by what she was seeing, and as if to confirm its reality, she reached out to touch it. Her fingers could not completely embrace its girth as she stroked along his hard rod. It was hot and she thought she could feel the beat of his heart throbbing under her hand. She moved her other hand to gently touch his testicles. They matched the size of his penis, large and swollen with the banked up store of his semen.
She understood his need and the torment of it and felt a deep compassion for him. Looking up at his young face she was conquered. She saw tears in his eyes as he whispered plaintively, “Nan, I’ve never been with a woman.”
She felt impelled to do something to relieve the obvious sexual stress that gripped him. She pressed him gently back against the cushions of the divan on which they were sitting, and saying, “Let me help you, darling,” she moved her fingers to where his foreskin lay nestling in folds beneath the great head of his penis and began to flip it quickly back and forth over the head.
He gave out soft moans of ecstasy and Nancy knew he was under her control. This was power over the boy. She could give or withhold release from his sexual thraldom, could have him begging for mercy.
The delight Nancy experienced at wielding such domination over Robert passed quickly as she saw his young body writhing under her manipulation and heard his frenzied cries. Knowing he was on the verge of discharging she speeded up her movements of his foreskin.
He reached out to fondle her breasts through the cloth of her dress. Suddenly Nancy felt his hands squeeze her breasts causing her delicious pain, and then he gave out a loud anguished cry of, “Oh Nan.”
His testicles where fulfilling their primordial function, sending sperm up his shaft. She slowed her movements but thrust back harder, almost as if she would tear his foreskin away from the head of his penis. Giving out gasping cries of, “Ah…ah…ah…” Robert gave upward thrusts of his hips to meet Nancy’s downward jerks on his foreskin.
The first ejection of hot semen burst out of his urethra. It shot up into the air several feet and came cascading down, some of it splashing on to Nancy’s face and dress. Eruption after eruption exploded out of him with a force Nancy had never witnessed with her lovers. She was fascinated by the sight of this massive discharge and Robert’s ecstatic cries, thinking how wonderful it was to be able to give such pleasure to him.
She began to think that he would never stop unloading his young seed, but at last the flow of creamy viscous sperm slowed to a dribble, and ceased.
Robert lay back gasping and she felt his hand that had continued to grasp her breasts began to relax as his penis slackened in her hand. He had discharged a huge amount of semen. In fact, as Nancy put it, there was “a hell of a seminal mess”.
Still holding his penis and looking tenderly into his eyes Nancy asked, “Feel better now, darling?”
“Oh God, yes Nan, it was beautiful…thank you…thank you…”
“Not a word to anyone,” admonished Nancy.
“No, never, I promise,” gasped Robert, still recovering from the powerful orgasm he had experienced.
Nancy had her own problem to deal with now. She had been powerfully aroused even before she started to relieve Robert, now, having witnessed the result of her giving comfort to Robert, she was in a worse state than ever. Her lubricant had run down between her thighs to create a sticky discomfort and she felt a torturing throbbing in her clitoris. If ever a woman was ready for penetration and impregnation, she was.
I hasten to add that Nancy was beyond the time when pregnancy was a possibility, but that did not stop her experiencing all the physical and emotional sensations that lead up to such an outcome.
She still held in her hand Robert’s slack shaft and as a means of getting her own pleasure and relief it was in that condition a fairly useless organ. In any case, two objections arose in her mind to any coupling with Robert. First, he had certainly enjoyed her masturbating him but, she felt that he was not likely to want to have sex with a woman nearly three times his age. Secondly, to have sex with Robert would be almost like incest since she had just about been a mother to him.
Contemplating her sexual and moral dilemma Nancy did not at first notice that the penis she still retained in her hand was hardening again. When she did notice it the organ had almost reached full stretch again and even then she could hardly believe what hand and eyes told her. None of her lovers had ever been able to achieve a second erection at such speed, yet here was the boy ready to go again.
Still Nancy might never have taken advantage of that mighty organ but that Robert made a move. She felt his hands move up inside her dress, caressing the naked flesh beneath. They reached her breasts and began to gently press them. In a quiet but tense voice he said, “I want you, Nan, I want you properly…please Nan…please…I’ve never had a woman…please…”
“We can’t, darling,” she said softly.
“Why not? Oh please, I want you so badly.”
“Darling, I’m too old for you and I’m almost like a mother to you.”
“You’re not too old, Nan, and you’re not my mother, so why not?”
“I just can’t, darling.”
“You said you loved me and you know I love you, so why can’t we?”
“I…I….” Nancy’s restraint was breaking down and one half of her wanted to find some reason why not to give herself to Robert, and the other half longed for his young red lips to close over her nipples, his tongue to lick her salt lubricant, and to have that great penis sink in to her female depths.
Robert broke the spell of indecision when he said, “I know you go with men, but you don’t love them, but you tell me you love me and you won’t do it with me, why?”
Nancy gave up the struggle to find some logical reason why not and said, “Darling, if it’s what you really want and you swear never to tell anyone, then just this once.”
“I swear I’ll never tell,” Robert replied in a choking voice.
Nancy said, “All right, darling, let’s do it properly and get undressed.” With that she pulled her dress over her head to stand naked before Robert.
She began to remove Roberts clothing while he whispered, “Your beautiful Nan, beautiful.”
Nancy pressed him back on to the cushions and leaning over him pressed her lips to his, her tongue probing for entry into his mouth. Robert seemed to know instinctively what to do, and his lips parted to admit her tongue. She explored his mouth, licking at his saliva as her hand continued to stimulate his penis and Robert’s hands convulsively pressed her breasts.
Nancy knew what Robert wanted at that moment – what so many men want – so she moved so as to bring a ripe pink nipple against his mouth. She had no need to do more because Robert sucked the sweet morsel into his mouth, sucking and licking it like a child hungry for the nourishment of its mother’s milk.
As Robert continued to enjoy her teat she drew his hand down between her legs and taking one finger, inserted it into her vagina and began to move it in and out. Robert got the message quickly, and soon he had three fingers working in her.
Nancy would have liked to sit astride his face and press her sex organ against his lips so he might give her oral sex, but decided that this was not the time. It was as if she knew this would not be the only time they would come together like this, and the moment would come when they would explore each other further. For now she would experience that massive organ penetrating her womanhood.
She came astride him and guiding his penis brought it to nuzzle up against the soft inner lips of her vagina. She did not let him penetrate immediately but moved the head of his penis in turn between her warm wet inner lips, letting him feel their moist warmth, and pressing it gently against her clitoris.
Robert responded to this with little cries and groans and after a minute of this teasing Nancy suddenly thrust down on him so that his shaft entered her vaginal tunnel.
I suppose most males before they ever experience copulation with a woman, have some image in their heads about what it will feel like to penetrate female genitals. Yet as most of them will admit, that image never truly conveys the sheer delight and ecstasy that is experienced the first time they enter the deep mystery that is woman, especially if that woman is experienced in the ways of sexual love.
Nancy was just such an experienced woman, yet she too was encountering something new. She had never been penetrated by such a massive sex organ before. She thought it might be painful, but instead it was sheer rapture.
As Robert entered her warm moist depths she felt for the first time ever her now distended sex organ completely filled. His shaft fitted tightly against her vaginal walls and pressed urgently against the top of her tunnel.
Having got his full length inside her she stayed still for a while, simply flexing her vaginal muscle round his organ. She got the extremely gratifying response of Robert’s almost delirious moans and whimpers, but it was when finally she began to move that he gave full voice to what he was experiencing.
“Oh God…Nan…it’s beautiful…don’t stop…please don’t stop…”
Nancy could have easily responded in like manner as she felt that great organ sliding up and down in her moist soft womanhood. Being Nancy she was in two minds what she wanted; whether to let it go on and on, or to release the orgasm she was fighting to hold back. The decision was finally taken out of her hands – or should I say genitals – by Robert.
He gave an almost animal howl and Nancy knew that it presaged his ejaculation. The orgasm that had been tantalizing her in the background as it were, she now let have its way with her. It hurled itself upon her, convulsing her entire body, and she gave forth with a piercing scream of tormented delight.
Shaking and shuddering she thrashed up and down on Robert as his semen erupted violently into her. “Make me pregnant…make me pregnant…” screamed Nancy, asking the impossible but responding to the primeval urge to create new life in her body.
In a sense that was the tragedy of the situation. As Nancy felt Roberts hot seed thud into her she desired fervently to be fertilised in a way she had never done before. As she engaged in this frenzied coupling with Robert she felt as if the years dropped away from her. There was no thought of age difference now; she was young again, a fecund young woman being impregnated by the man she loved.
She was in the grip of an overwhelming and desired only to surrender to this brief time of delicious torment as her orgasm reached its climax and stretched her helpless on the rack of that agonising blend of love and lust.
Robert completed his ejections, but Nancy continued to move on his now slackening manhood making soft, sobbing, whimpering noises as her orgasm continued to send diminishing shock waves through her. She dropped forward pressing wet kisses and licks over Roberts face moaning, “I love you…I love you…”
Thus far I have tried to put in writing what came to me from Nancy, albeit not in an orderly manner but in bits and pieces over several hours of conversion concerning her “Dilemma.”
As Nancy saw it, her world had been turned upside down. What had been intended as a once only coupling with Robert had extended beyond that.
“We can’t leave each other alone,” she sobbed. “I need him…I really need him, and he seems to need me. What am I going to do? From that first time we came together I knew no other man would be able to satisfy me again…that huge, beautiful…Oh God, it’s so big…I want him so badly.”
I could see that even just talking about it had aroused Nancy. Her face had turned bright pink, her lips moistened and she could hardly keep still.
She went on to tell me how they now slept together and copulated constantly but things might come to an end soon because Vera was due home in a few days.
“What are we going to do,” she moaned. “We need each other so badly.”
I saw her problem – or rather, problems. She could only stay in the house at the invitation of Vera and it would not be safe to take Robert to her own house. This problem I could help with, so I offered her the use of one of my bedrooms where they could meet and make love as often as possible.
The other problem was an insoluble one. There was the huge age gap but Nancy was not acknowledging this at the time. It was true, the new found “Love of her life,” as she called Robert, had indeed stripped away the years.
If before she began the sexual relationship with Robert she had looked in her mid thirties, she now looked even younger. I could see that there would be difficult times ahead for her when the heat of their passion had cooled and Robert began to see her as the age she was.
Another problem was the change in their relationship. As I have said, the relationship had been a maternal one. Perhaps something of the maternal aspect would remain, but now they were lovers with all the emotional and sexual intricacies that such a relationship entails.
One interesting and slightly amusing aspect of their affair was told me one day by Nancy.
“Do you know what Vera said to me the other day? She said Robert seemed to have changed a lot lately. He’s not so dejected and seems to happy and relaxed.”
I am writing this story almost twelve years after Nancy came to me with it. The final outcome is not yet known, but for about five years Nancy and Robert made use of the bedroom I had offered, coming together as often as they could. Then Robert moved out of home and into a flat of his own. It was there that they continued their sexual intimacy.
Robert got married and there has been one child from the marriage. Nancy, who did not seemed particularly upset about Robert’s marriage – in fact she even seemed to encourage it – is still visited by Robert. I am given to understand that Robert professes great affection for his “old Nan”, and under the cover of going to “see if she’s all right,” they have returned to using the bedroom I offered them so long ago.
If you have any doubt about Nancy’s ability to perform or Robert’s desire to, be assured I often hear their cries and moans as they enjoy each other.
I wonder if there is a message here for Nannies and mature women?