Preamble.

Once upon a time, there was a world where there were no mobile phones, no internet, no dating apps, no cable or streaming TV services, and very few broadcast channels.

If you wanted to talk to someone, you had to find a telephone (if they also had one!), or write a letter and wait at least a week for a reply; much longer if it was an 'airmail' letter. This all made communicating outside your immediate community very slow and difficult.

It was also a very difficult time for young people to learn about sex.

Of course, there was no internet porn, and the new medium of video was hard to access. Mainstream films were 'rated' by age and highly censored, and the more sleazy cinema clubs in the back streets wouldn't admit young people. There were 'top-shelf' magazines, intended to be out of reach to young people, but also very restricted in what they could show.

'Sex education' in schools was pitifully inadequate. It often involved an embarrassed teacher talking about 'the birds and bees', communicating nothing of any meaningful value. Parents were equally embarrassed, and often even more ill-informed. No wonder the youngsters were embarrassed to talk about sex too! They didn't even have the proper language to talk about it.

Contraception was clumsy and not easily available, and again, misinformation ruled at a time when abortion was illegal, and it was not uncommon for a pregnant young girl to be banished from the parental home, or even her community. This was true even in the so-called 'Swinging Sixties', in London. Fear of pregnancy and 'STD's' was a real inhibitor in those days, when the Pill was still a new and rather scandalous issue.

Grubby magazines circulated amongst friends, as did ridiculous rumours, theories, misinformation and misunderstandings. Gay sex was illegal (ridiculously enough, so was suicide, although Capital Punishment was still in force!) and any departure from the established norms of appearance or dress code was regarded with great suspicion.

All of this may still be true in some parts of the world even now (and some supposedly sophisticated countries may be rapidly heading back in that direction!) but this was in the so-called 'developed' Western world. It is astonishing to think how recently all this was true in both the UK and USA, and may return.

It was in this period that young Simon tried to learn and to develop his own first relationships. When he was in his late teens, he was the first of his family to go to University, and was still a virgin, despite some tentative fumblings with local girls.

He had managed to see “The Graduate”, and identified very much with Dustin Hoffman's character. He also dreamed of having a “Mrs Robinson” to take him under her wing and educate him in the ways of the world. She was probably the original MILF, though the acronym wasn't popularised until the Eighties at earliest, and maybe even the Nineties.

The Freshers.

Simon joined University nervously, as a Fresher (or a 'Freshman' in the US), knowing nobody at all. He still lived at home, having chosen a local University, to keep his expenses low, and still worked a part-time job at a warehouse, to contribute to family expenses. However, his fellow undergraduates came from other towns and cities, and a different stratum of 'society'. He felt rather excluded.

He had always had very little spare time (and money) to socialise, but he had earlier managed to meet a local girl, and strike up a tentative relationship. Like him, she still lived at home, fairly locally, and worked part-time at a local store. Unlike him, she had opted to go to a University further away and would soon be leaving for her first term there.

Sue was a very attractive girl, the same age as him, but both were quite naïve in many ways. They were both virgins, but both wanted to start their University lives without that burden. So they both decided to have their first sexual encounter before they parted and went their different ways; it was not impossible that they would meet again during term breaks, when Sue would return home.

She invited Simon round to her house, for the very first time, and introduced him to her mother; the father had left them both some time ago.

Simon was astonished by the youthfulness, and indeed the beauty, of her mother Jill. She was in her late Thirties perhaps, having had Sue at an early age, but she was very similar in many ways, and could easily have passed as an older sister.

They were both shapely, but the mother a little more so. They both had long legs, ample breasts and long raven-black hair curling down below their shoulders. They were so similar that Simon wondered whether Jill had modelled Sue on herself, or whether Sue had simply copied the mother she admired.

The introductory conversations were difficult, not least because Simon was already very aroused by the promise of sex with Sue, and that was exaggerated by her mother's presence. He felt that she knew what was planned between her daughter and Simon, and he was unsure whether she approved.

There was a glint in her eye which puzzled him a little, and it shone brighter when Sue boldly announced that Simon was going to stay the night. Jill smiled her understanding, and at the end of the evening, left them alone.

It was NOT a night to remember, unfortunately. Both were very anxious, for numerous reasons, not least her mother's presence in the neighbouring bedroom. Sue wanted them to be as quiet as possible, and wanted Simon to use a condom; at least he did have some, but both were unfamiliar with the processes. He found the donning of the condom very difficult... there was no education in such matters.

Sue was concerned at the size of Simon's cock, though it was the first she had ever seen; Simon was concerned that his throbbing balls would shoot their load too soon, especially when he found her pussy hidden by her dark bush, and struggled find his way to force his sheathed cock inside her.

They fucked silently for their first, very short, time. Simon came, of course, but Sue showed little reaction, and seemed rather relieved when he withdrew, with his cum safely encased in the condom. Inexperience and the fear of pregnancy had almost neutered them both.

They cuddled together afterwards, and were both relieved that they were no longer technically virgins, but each of them wondered what all the fuss was about. Secretly, they both thought “Was that it?” behind their forced smiles at each other.

Sue set off for university that very weekend. Despite her promises to keep in touch, his letters went unanswered. He flirted and dallied with a few girls, but still thought of Sue as his girlfriend, and did not engage in any serious sexual encounters. When vacation time came, a couple of months later, Simon went round to her house to see if Jill knew when Sue was returning, as he had heard nothing from her at all.

The Entry Examination.

Jill welcomed him and offered him a home-cooked meal. She said that Sue had called her to say she was staying in her new city through the vacation and had started living with a boy she had met there. Simon was devastated and asked whether Sue had said why she was no longer interested in him.

Jill consoled him, and said no doubt he had found other girls, since Sue went away. He admitted to that, but nothing 'serious' had developed, and he had harboured hopes of rekindling and developing his relationship with Sue, when she returned. It seemed that that was unlikely now, and he was disappointed.

Jill offered Simon a drink and sat alongside him. Her voice was soft and mellow, and he felt very relaxed in her company. Their conversation began to range around how difficult relationships could be, and what was necessary to keep a strong partnership. It seemed that Jill had had a fairly adventurous sex life, with numerous partners, before she became pregnant with Sue, and Simon was amazed (and rather aroused) by her candid stories.

Jill then surprised Simon by admitting that it was her own unfaithfulness during her pregnancy that had led to her divorce, and that the need to provide for Sue had then dominated her life until now. She felt very alone in Sue's absence after all these years. She had not been able to form any new partnerships while caring for Sue, and was feeling very frustrated. She was supposedly 'free' again, but seemed unable to take the very first steps.

The drift of this conversation was exciting Simon, though he knew that was 'wrong' in some way- after all, this was the mother (albeit very attractive) of the girl he had hoped to continue to bed, though hopefully more successfully.

Jill then said, “Sue told me about your first night together, Simon. She was a little disappointed, but I guess that was just inexperience on both sides. I know she had never had sex before.”

Simon blushed a deep red at the thought that Sue and Jill had discussed his performance, and stumbled with his words. Jill said, “There's no need to be embarrassed, Simon! We all have to learn, and find our way through these things... sex is a minefield. Believe me, I know!”

At that moment, her hand fell to rest on his thigh, and he jumped involuntarily.

Jill looked him in the eye and simply said, “Simon, do you find me attractive?”

Before he could even stutter a reply, her hand slid up his thigh and stroked his erect cock. She seemed impressed, because her hand stayed there, caressing him more and more firmly, while her eyes locked with his.

“Would you like me to give you the benefit of my experience?” she breathed. “It would be a pleasure to teach you what a woman needs from a young man like you.”

Simon could hardly speak, but certainly did not resist when Jill guided him to his feet and knelt before him. He was in awe of this older version of Sue, her hazel eyes shining from a perfect face, framed by her long, shining black curls reaching down to her shoulders. Her brows and lashes were also dark and well-defined, and her pouting lips were scarlet red, with her pink tongue flickering between her pearl-white teeth. Her long fingers were tipped with long scarlet nails, which stroked his cock as it pressed urgently against the denim of his jeans.

She looked up at him, while she slowly unbuttoned her white blouse, and revealed her proud breasts topped by firm, erect brown nipples. He sighed loudly and had to look away, up to the ceiling, while he felt her deft fingers unbuttoning him. Then it was Jill's turn to sigh, as she finally revealed Simon's cock, and traced his throbbing veins from tip to base, with the edge of a long scarlet fingernail.

“That is impressive, Simon,” she said, “it is one of the biggest I've seen, and so, so hard! Sue doesn't know what she's missing, I think.” She giggled girlishly, and added, “Not that I'll be telling her that, of course!”

“The greatest lesson you can learn, Simon, is that of self-control. No matter what else you learn, the most important thing of all is to delay your release, until you and your partner can wait no longer. The anticipation, the expectation, the longing for satisfaction is heightened to almost unbearable levels if you can wait... and wait... and wait, until your partner cannot. There are many other things I could teach you, Simon, but that is by far the most important, and it only comes with practice.”

She raised herself to her knees, and pressed Simon's cock between her ample breasts, squeezing them tightly around him. Slowly she moved herself up and down his hard shaft, while her hands squeezed her breasts around him, and her thumbs teased her own hard nipples.

Simon groaned, still trying not to look down at the most exciting vision he had ever seen in his life. Eventually, though, he just had to look. And as soon as he did, Jill dipped her head to envelop the head of his cock with her lips. He shuddered as he felt her tongue circle the swollen head, and she sucked gently on him.

She withdrew him and said, “You've already done very well, Simon! Many more experienced men would have cum already, so I think you have great potential to become an expert lover. We will take a step at a time, though. Have you ever cum in a girl's mouth before? Has Sue ever sucked you off?”

He shuddered again at the very thought, and said, “No! This is the first time I've ever felt this! Do you mean you want me to cum now?”

Jill laughed and said, “Not quite yet, Simon. You will have to wait while I prepare myself, so keep holding on!”

One hand, lubricated by the saliva which dribbled copiously down his shaft, stroked firmly down his cock, while the head stayed motionless inside her mouth, and was teased by her tongue.

Her other hand slipped down between her open thighs, lifting the hem of her skirt, and tugging her brief panties to one side. Simon could see that, unlike her daughter, she was almost hairless, and watched in fascination as she inserted a finger deep inside her wet pussy, spreading her lips apart, and teasing her clit with her thumb.

Her head began to move up and down, in sync with her finger penetrating her cunt, and she began to grunt in rhythm. She looked up at him, and her eyes told him, without words, that she was ready for him to cum. Her movements became quicker, more determined; her eyes focused on his, staring deep inside him.

Simon was surprised that he had detached himself sufficiently to survive this treatment, so far, but now Jill's eyes gave him permission (indeed, they demanded) that he should cum. He held her head gently between his hands, his thumbs pressing into her ears, and his hips moved very slightly back and forth. He was uncertain how active his participation should be now, but he was suddenly overwhelmed by a biological imperative to thrust into Jill's mouth as deeply as he could. She gagged as he hit the back of her throat with each thrust, and tried to restrain him a little with her hand, but he slipped easily through her grip.

She looked up at him again, and when he froze still inside her mouth, his cum began to pump into her. She swallowed as much and as fast as she could, while her eyeballs rolled up under her lids, showing the whites of her eyes, and her lashes flickered furiously.

When her hazel eyes refocused, and his spurts subsided, she withdrew his cock and gasped for air, while white cum dribbled from the corners of her red lips. Her lower hand was clenched tight between her thighs, which shook uncontrollably.

Simon's legs were shaking too now and he had to step back and sit down, while his whole body trembled with the release of accumulated passion.

Jill rose from the floor and sat alongside Simon.

Still a little breathless, she said, “My God, Simon! You are the perfect student; there is SO much I can do with you! I think you could be a great student, with all the emphasis on 'STUD'.”

And so it was that Simon embarked upon studies that would change his life. Jill was a keen and committed tutor, and he was an avid and conscientious student.

The Oral Examination.

Simon neglected his academic studies more than he should have, but felt that the lessons Jill taught him were more relevant to his future. She had no expectations of forming a permanent relationship with her student, only seeking her own pleasure in the course of educating him.

They agreed a series of practical exercises, to educate Simon in all the skills Jill could imagine, while pleasing herself in the process. As she had said in the very beginning, the most important skill was control and restraint on Simon's part, but also recognising the moment when the final explosion of passion was called for. He had made a good start in his very first experience of fellatio, but Jill was keen to teach him how he could please a woman orally.

That was to be his next lesson, but first he needed a thorough grounding in female anatomy, which had been denied him in his education to date. Drawings in Biology textbooks had told him something, but not much!

Jill invited Simon to study her, in every detail, and he did not object. She laid herself naked on her bed and suggested that he should explore her as he wished, and ask any questions he wished. She suggested that he should start his explorations at her feet, and move steadily up her body. He was happy to do that, but just the sight of Jill laying there, fully naked and exposed to his view, had the obvious effect on him, and that was obvious to Jill too. She said it was a further test of his ability to restrain his natural urges, and take time to please her, rather than just himself.

He stroked her feet, from the red toenails, to her ankles, and she made approving noises when her lifted each foot to massage it firmly, pressing his fingers into the sole, and spreading her toes. She said it was a delicious agony, and he should hone his natural skills as a masseur- his fingers were long and elegant, but strong too. She could imagine them playing all over her body, probing and teasing.

That is what developed, in fact. His hands moved firmly up her calves, his fingers stroking the crease behind her knees, and progressed up her thighs, parting them to gently caress the soft skin between them, and stroke upwards towards her pussy.

She tried to relax and just enjoy his touch- light, and at the same time, firm – but when he first touched her pussy, she squeaked involuntarily. He apologised instantly, but she giggled and said, “No, Simon! You must carry on exploring me- I'm loving it!”

And so he did! He had already noted that, unlike her daughter, she was waxed smooth, with only a short, neat triangle of hair pointing down towards her pussy. It suggested such sophistication and experience in his mind, and he felt honoured to be granted this access to her.

He spread her legs before him, and leaned close as he stroked her pussy lips from back to front. They were becoming more prominent and puffy as he teased them, and beads of moisture were gathering, oozing from between them.

“Mmmm, Simon,” she groaned, “you have to explore within! Open me up to your gaze, now, and take note of everything you see.”

He dutifully parted her slick lips, and spread her open, to see the darker well of her cunt, brimming with liquid honey. He dipped one long finger just inside her, and withdrew it slowly, hesitatingly bringing it to his mouth, for his first taste of an aroused woman. She was delicious, and he told her so.

“You should taste me at the source, Simon!” she said. “And then you must seek out my clit. It is vital that you learn how to play with it... it is SOO sensitive, you need to be very careful.”

He did as instructed, lowering his mouth to her cunt, and delving his tongue inside her, circling it around the rim, then delving inside again and again. As he withdrew, his tongue flickered upwards, while Jill pressed her hands against her mound, helping her clit to emerge in front of his eyes. He was fascinated by her red button, standing proud like a miniature cock.

When he placed his lips around it and sucked it between them, Jill squealed with delight, That was heightened when he slipped a long finger, then two, back inside her cunt, and probed as deep as he could, while sucking and licking her firm clit.

Her hips began to rock, pressing herself against his mouth and his fingers, and moved more and more rapidly, more and more urgently, while her breathing became more fractured. She reached down to hold his head against herself, pressing harder and harder. She did not want him to leave her now, until she reached her climax, and Simon understood that that was brewing rapidly.

He had never witnessed a female orgasm before, and his attention was so focused upon Jill, that he almost forgot his own throbbing erection. He rightly thought it would not be wise to touch himself now... his hands, fingers, mouth, lips and tongue were all devoted to pleasuring Jill to an ecstatic conclusion.

When it did come, it shocked him in its ferocity. She forced his head against her, and gripped him with her thighs so hard that he feared his skull might crack! She screamed loudly and shook bodily, tremors ran throughout her, and he felt the fluttering of her pussy while her cunt gripped his fingers rhythmically, squeezing and milking them as they would a cock.

He stopped moving at all, then slowly withdrew and disentangled himself from between her thighs, which still shook from time to time.

“Was that OK, Jill?” Simon asked nervously. “Are you OK?”

She burst out laughing and he was a little frightened that she might mock him. But no, that was certainly not her intent. She assured him over and over again that he had done everything right, and could not have done better. He was 'a natural' she declared.

Jill looked down at Simon's hard throbbing cock and said. “You even managed not to cum! That is excellent, Simon! But now you need and deserve some relief, don't you think? You have certainly earned it.”

Simon stood between her spread thighs, and he expected her to take him in her mouth again, but she had different ideas. She took his cock in both hands, and stroked downwards only, one hand following the other, in an endless sequence, mimicking a continuous penetration, deeper and deeper and deeper, into a slick wet cunt.

He gasped that he could not wait much longer, and Jill assured him that was not necessary; she wanted to see his cum shoot from the swollen cock she held so tight. He threw his head back and roared as his hips thrust against her slick hands, time and time again. Then, just as before, he stopped still, fully forced through her grip, and she knew he was about to cum hard; one hand slipped down to hold his balls and feel them throbbing urgently.

She looked up at him and said, “Watch, Simon, watch your cum shoot over me.”

He did, and was shocked by the force and pure volume of cum which shot from him.

Of course, he had masturbated alone many times, but this! This was more than he had ever produced before, and shot fiercely above Jill's head, falling back into her glossy, long, black hair, dripping from her fringe, down her forehead, down her cheeks and from her chin. He was astonished that she seemed to enjoy this assault, and she smiled at him as rivers of cum joined to flow down between her pert breasts, across her firm belly, and disappear into its natural home between her thighs.

Just as Jill had done, he shook bodily, while she coaxed every last drop of cum from his slowly-softening cock, licking the final drops up with her pink tongue and drawing it inside, to please her taste-buds.

“I think we both need a shower, don't you, Simon?”, said Jill, smiling broadly at him.

That was yet another sensual experience he had never had before, and he quickly learned of Jill's sensitivity to his soapy exploration of her breasts and nipples, but much more was awaiting him.

The Graduation Ceremony.

The following week, Jill scheduled a lesson in actual fucking. They had discussed how Simon and Sue had abjectly failed to please each other; Jill was clear that it was not just Simon's responsibility, but the result of inexperience for both of them.

When Simon mentioned the need for a condom, and their joint fear of pregnancy, Jill said she fully understood how inhibiting that must have been. She herself was on the Pill, and had considered arranging for Sue to be prescribed before she went away to University. She had not done so, and now felt that was a mistake,,, it would have been the responsible thing for a mother to do. She did not subscribe to the “just say NO” school of thinking!

Clearly, there was no need for a condom, with Jill, and Simon was greatly relieved; his first experience with Sue had scarred him psychologically.

They undressed each other sensually, and Simon played with Jill's breasts as he had learned in their shared shower. She enjoyed them being squeezed and fondled firmly, bringing her nipples to full arousal and pinching them quite hard.

She laughed and complimented Simon on his rapid learning, while she stroked his hard cock, and complimented him on that too. She assured him that he was genuinely bigger than most men she had seen, and impressed by his thickness; she could see why he had found it difficult to put on a condom for the first time, with Sue, and how that might have disturbed their special occasion.

Simon, of course, was pleased to be reassured by a woman of such experience, and his cock seemed to swell even more, with pride.

They spent a considerable time on mutual foreplay, but only with hands and bodies pressing against each other. There was no oral preparation by either this time and Simon wondered whether he had 'passed' in that particular subject. He thought so.

Now, they were pressed together, his cock throbbing against her belly as she guided him to lay on top of her.

“I know we're not religious, Simon,” she smiled, “but I do think we have to begin with the Missionary position, don't you? This was what you tried with Sue, wasn't it, and I think we'd better get past that before we try anything more... adventurous.”

Simon wasn't even sure what other thoughts she might have had in mind, but he was very happy to continue like this!

She guided him to raise his body, and reached down to press his cock against her belly. “Look, Simon,” she said, “you can see how far inside me that gorgeous cock will reach! And even further when you slam it hard into me, and shoot your cum further still!”

Those images set Simon's mind spinning, and he had to reassert control over himself by looking away. This was nothing like the experience he had had with Sue!

Jill reached down between them, to direct Simon's cock between her thighs. She jolted as the head slid over her clit, but guided it down between her wet, open pussy lips. He did not thrust into her, much as he wanted to, but waited patiently while she located his cock at the opening of her cunt. He felt a slight gripping of the head as she angled her hips to accommodate him.

She looked up at him and said, “Simon, I want you to kiss me deeply and passionately, but keep your cock where it is until I tell you to fuck me! It won't be long before we're locked together at both ends.”

Simon obeyed, and their open mouths locked first, their wet lips writhing against each other, while their tongues darted and flickered into the other's mouth. They both became breathless, and Jill turned briefly aside.

Her hands grasped the cheeks of Simon's ass, and as she said “Fuck me, Simon, fuck me hard!” she pulled him into her just as their mouths re-engaged. That first deep jolt was wonderful; it forced the air out of their lungs, and into each other's. It was a total melding of two bodies into one.

For a moment, they lay there, deeply locked together. Then, Simon felt Jill's hips begin to rock as she angled herself to wring the maximum pleasure from the rigid cock deep inside her. She felt it pressing against her inner walls, while her pussy was stretched wide to accommodate his thickness.

He knew it was time to fuck, and began to move in and out of her slowly, steadily at first, but gradually with increasing force and speed. She was gasping with each thrust into her now, and her hips moved in harmony with him.

Simon was intent on controlling himself, and not disappointing Jill, but he need not have worried. She raised the pace, and began to grunt with each thrust into her; he recognised the signs of an impending orgasm from their oral encounter, and knew he could soon release himself.

Their clashes were deep, hard and fast now, until Jill suddenly let loose a howl of anguish and stopped moving, except for the quivering, shaking response to the surges of cum she felt pulsing up Simon's cock, and squirting deep inside her, filling her to the brim. Simon halted all movement and let himself empty completely inside Jill's trembling cunt, milking every last drop from him.

They lay exhausted together as their tremors subsided, still engaged in full. Slowly, Simon moved cautiously to withdraw from Jill, and she gasped as she felt the flow of cum from her stretched cunt, down between her thighs.

She looked up at Simon and said, “You passed your 'Finals', Simon, and with First-Class Honours!”

Simon grinned and replied, “I hope that wasn't the finale, Jill. I'm sure I could do better with practice!”

Jill said, “Oh, Simon, there are so many, many more ways to fuck... I don't think you have any idea! We will have to enrol you in the Masters Course next, as a First Class Postgraduate. That can take years, you know!”

They both fell into a deep, satisfied sleep.

The Post Graduate Trauma.

Simon had been looking forward to their next encounter, because Jill had told him how much more there was for him to learn. In truth, it is a never-ending process throughout life, but he was impressed with the long list of different positions she had quoted, and excited at the prospect of learning each in turn.

She wanted to help him to a Master's Degree in sex, she had said.

When he first saw her the following week, he immediately knew that something was wrong. Instead of the usual hugs and cuddles, leading quickly to the bedroom, she sat opposite him at the dining room table, and her face was serious. She was upset.

“We may need to take a break in your... education, Simon,” she said, “maybe permanently.”

Simon was in shock. He thought he had done everything right, and Jill had seemed ecstatic when they last met, full of plans and ideas for the future development of his 'coursework'.

Hesitantly, Jill explained that Sue had been in touch and it seemed that her newfound relationship there had broken up; she had had to move out of their shared flat. She had described her (now ex-) partner as selfish and inconsiderate, as well as being domineering, and potentially abusive.

Sue wanted some time back at home, to compose herself and reassess her life, and of course, Jill had told her that her room was still waiting for her. However, Sue had also made a point of asking whether Simon was still in the area, and whether Jill knew anything about him.

It had been difficult for Jill to answer; she did not want to lie to her daughter, but nor could she tell her the full truth! She admitted that Simon had come round to enquire after Sue, and had seemed upset when he heard about her new partner.

Tears rose in Jill's eyes as she explained all this, but she composed herself and said that she did not want to 'stand in the way' if Simon and Sue both wanted to rekindle their relationship. Sue was returning next weekend, to stay for a week or so.

Jill asked whether Simon wanted to meet her. Of course, he did, but he was also upset and confused now, his mind and body in complete turmoil. What was he to do?

Simon and Jill sat facing each other across the table, and both faced a dilemma! What will they do?