Penny's Pleasure

Literotic asexstories – Penny's Pleasure by pandsal,pandsal
This story was suggested by a lady who calls herself Penny, which may or may not be her real name. Penny is married and, it seems, enjoys sex with a man; we have seen photographs (though it would be improper for us to publish them) in which Penny, if that is her name, opens her legs to have her cunt licked, presumably by her husband, whose real name may or may not be Mark. Penny also claims to need and enjoy frequent masturbation. This activity, whether with her fingers or with artificial aids, is greatly enhanced, she claims, by a certain type of fantasy. This site already offers one such fantasy, Penny’s Progress, which was written with her guidance. Her latest request, Penny’s Pleasure, develops a similar scenario. Whether the events portrayed really are no more than a figment of Penny’s erotic imagination, or whether they are a disguised version of actual experiences, who can say? The reader may wonder whether Penny exists only in the minds of the authors but in that case the reader would be mistaken. We are in a world where the lines between truth and fiction are easily blurred. How much of what follows is true and how much invented, the reader must decide. We simply hope that when Penny reads these words and slips her hand inside her knickers she will recognise herself, be pleased – and ultimately satisfied.

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Boredom was never a problem for Penny. Her difficulty was finding time to indulge. There was a house to maintain, a husband to care for in and out of bed, a demanding child whose inquisitive nature had to be channelled away from sensitive areas, a sister in another city who claimed her attention from time to time. Now Mark was suggesting they should investigate the local swinging scene. Penny was tempted but from past experience she knew developing the right contacts needed long-term care and patience. If only there was an extra day in the week …

Yet Penny was also aware she needed an outlet for the sexual energy that had been building for some months. Maybe it would have been easier to sublimate if she had not had one earlier glimpse of the promised land. Her patronage of a new lingerie boutique had led her into a series of experiences which had opened her eyes (and not only her eyes) to the joys of bisexuality. The interested reader can find a detailed account, slightly disguised for reasons of discretion, in the story entitled Penny’s Progress.

At the time there had been every reason to believe that her involvement with the boutique proprietress, Carla, and a selection of her clients, would continue and flourish. There had, after all, been room for Mark’s occasional inclusion, too. But Carla had made the mistake of allowing into the circle a young woman who proved to be an undercover reporter for a tabloid newspaper. The resulting scandal led to the closure of the boutique and Carla’s hasty move to another part of the country.

Fortunately, Penny had not been present at the gathering infiltrated by the reporter and so had been spared unwanted publicity, but the narrow escape made her all the more cautious about seeking out local swingers. Her solution, only partially satisfactory, was to give rein to her penchant for masturbation which had been her favoured form of release since her early teens.

Before meeting Carla and acquiring a whole new wardrobe of provocative lingerie, Penny had been happy to please Mark by wearing black bra, knickers and stockings. But for masturbation she had formed the habit of wearing white cotton, no doubt some kind of subconscious throwback to the days when she had first experimented with self-pleasure. It was to this routine that she had returned in the aftermath of Carla’s disappearance.

On the rare occasions when she had the house to herself and could be sure of not being disturbed, she would sit in a favourite armchair, lift her skirt, spread her legs and slide a hand inside the waistband of her knickers. Closing her eyes, she liked to recall her initiation with Carla and a plainish, brown-haired woman named Sonia. Over time it was Sonia who gave Penny her most intense orgasms, and there was one image that always came into Penny’s mind as soon as her fingers began to stimulate her clitoris.

In her memory they were all three naked on the floor of a room at Carla’s home. Penny was on her back with cushions beneath her head and bottom. Carla’s tongue fluttered across her nipples. Sonia’s hands lifted her knees, widened her thighs. Penny tensed momentarily but was quickly persuaded to relax. Sonia’s fingers probed her labia, tested the inner wetness. Two digits, then three, entered, withdrew, entered again. Carla was murmuring into her ear, “It’s going to be very good, Penny. Your cunt will be on fire. Nobody does it the way Sonia does.”

When Penny began to writhe and moan the two women immediately read the signs of approaching orgasm. The arousal was allowed to slacken off but not completely. Penny, having been so close to the edge, was afraid they might not take her all the way. She began to make thrusting movements with her pelvis, trying to encourage Sonia to complete what she had begun.

“Not yet,” said Carla quietly. “Much too soon. Are you all right?”

“Yes,” said Penny. “But please keep doing it.”

Nowadays, the recollection of the huge, heaving climax she was eventually brought to, Sonia’s mouth and tongue invading her cunt while Carla pinned her shoulders to the floor, invariably coincided with the conclusion her fingers had been working towards. Then it was time to clean up, drop the damp white cottons into the laundry basket and go about her business.

She needed a couple of passport size photographs and the nearest photo booth was at the local mall. Having checked that she had the requisite coins for the machine, Penny was exasperated to be confronted by an Out of Order notice. No indication of when it might be functioning again. Not wanting another wasted journey, she remembered a professional photographer on an upper floor. Probably that could provide what she wanted. Probably at twice the price of the booth but there was no easy alternative.

The photographer’s premises were open and not busy. A middle-aged, well-built woman greeted her, showed her into the studio and introduced the photographer, Gary, a young black man. Gary fussed with lights more than Penny thought necessary for a simple task but certainly went about his work confidently while making pleasant small talk. He told Penny how attractive she looked. Penny said she hoped the photographs would show as much but it wasn’t really important that they should.

Whatever the outcome it would have to wait. The woman in the front office explained that this was a professional job; their policy was to have the photos developed and to offer proofs from which Penny could make a selection. Penny stifled an impulse to be curt in reply. She asked if they would just choose what they considered the best, print off half-a-dozen and put them in the post to her. Could they do that before the end of the day? Of course they would be pleased to do so. Penny gave her address, paid and went home.

ID cards are are ID cards, not portraits for posterity. When they arrived in the mail, they had benefited from being properly lit and developed but hardly justified the extra expense. It was only when she was tidying later that Penny noticed on the back of the compliments slip a hand-written note:

“I hope these are what you require. If I can be of any further service please do not hesitate to contact me. You might be interested in some of the work we do – there are many opportunities for an attractive mature woman such as yourself. Why not arrange to comeand see us? If I am not here, my assistant, Alexandra, will be pleased to help.”

Frances Stertori (prop.)

Penny wasn’t thrilled by the word ‘mature’ but ‘attractive’ softened the effect. In any case, she couldn’t envisage herself as a model. She dropped the slip in the bin.

The circumstance that caused her to change her mind was strange. A few days later, during a deeply sensual masturbation session in which she several times brought herself to the brink before changing tempo to delay the orgasm, she found her mental images of Carla mutating into Frances Stertori. Thinking about it while changing her knickers afterwards, she realised that there was a striking similarity between the two. Like Carla, Frances was probably in her early fifties, well-groomed, full-bodied, softly spoken but with an authoritative air that was hard to define.

Perhaps, Penny mused, it was no more than a symptom of her now frustrated bisexual leanings. Carla’s policy had always been one of utmost discretion for the select clients whom she invited to her gatherings. Her guests never knew each other’s surnames, could never be sure that the names by which they were known at the parties were not invented. It was a rule that no phone numbers of addresses were exchanged. When they left Carla’s house they all retreated into secret compartments, into their separate lives. It meant that when Carla fled, Penny had no means of contacting Sonia with a view to pursuing their intense relationship independently.

Now here was Frances Stertori evoking comparisons Penny couldn’t dismiss. She tried telling herself the possibility that Frances might be another Carla was too much of a coincidence to be given credence, no more than an erotic fantasy. And yet …

Before she could gives herself time to change her mind, Penny went to the phone book, looked up the number and dialled. An unfamiliar voice answered, announcing herself as Alexandra. For a moment, Penny was tempted to say it was a wrong number but when she gave her name, Alexandra seemed to be expecting her call. Frances, she said, was hoping Penny would ring. They agreed a date for an appointment.

Without her husband’s encouragement, Penny might still have backed out. Mark remembered the liberating effect of Penny’s involvement with Carla and the pleasure it had led to for them both. If that could be recreated, he was fully in favour. In bed, listening to Penny’s strange intuition linking Frances with Carla, he sensed the attraction. But it was so nebulous. He said, “Maybe. But that’s in the future. Who knows what will come of it? Probably nothing. But this is now. Feel this.” He guided her hand to his cock, already hard and demanding. “We’ll find another woman for you somehow, I promise. But don’t forget me. Fuck me, Penny.”

She knew he was right, and she didn’t intend to forsake the intimacy and the hungry mating that was sex with Mark. She turned on to her knees, knowing that Mark enjoyed nothing more than a fuck doggy-style. Taking his cock in his hand, he fed it into the opening of her cunt. She was wet and it was easy to absorb his shaft. He grasped her hips and began a driving rhythm. Instinctively she understood. All wish-motivated fantasies were banished as she concentrated on the animal-like nature of the coupling. It wasn’t always like this but sometimes it was good simply to give way to the most basic desires. She knew Mark couldn’t last long this way, wished that she could time her climax to synchronise with his but understood it was impossible. It was the eternal difference between the male and female orgasm. Even before she could reach beneath herself to finger her clit, a gasp and a final lunge signalled his discharge into her cunt. Mark clung to her for a few seconds, kissed her cunt twice and then flopped on to his back. Soon he was asleep. Penny lay awake musing about Frances.

**********************

Penny’s appointment had been made for the time at which the photographers closed for the day. “Then we won’t be interrupted,” Alexandra had said without explaining why that might have been undesirable.

She was welcomed by the proprietress and shown into an office. “First, let me thank you for coming,” said Frances Stertori. They were sitting facing each other on comfortable chairs. Behind them was a desk with a few papers, a phone and a computer. “We are always on the lookout for new models but we seldom come across one so attractive in your age-group.”

The flattery seemed sincere enough but Penny remained wary. In the back of her mind she knew exactly why she had accepted the invitation but she had decided that if any covert signals were to emerge they would not be from her. Rejection would be more embarrassing than she could bear. She declined a glass of wine but accepted the offer of coffee.

“Please call me Frances,” the woman said. “This is really just an informal little chat to see if you would be interested in any of our channels.”

“What would they be?”

“Oh, various types of photography. Across the whole range, really. I could show you some examples, but first may I ask you a few questions?”

“Of course.”

Frances reached for a file from the desk. took out a sheet of paper and attached it to a clip board. “We have the basic details – name, address, telephone and so on. No need to go through those again.” She looked up with a warm smile. “How old are you, Penny?”

“Thirty-nine.” No point in dissembling.

“Measurements?”

“Thirty-eight, twenty-eight, thirty-eight.” More or less, she thought. It was a while since she’d checked.

“Thirty-eight D – would I be right?”

Penny nodded. Frances made a note.

“You are married?”

“Yes.”

“Children?”

“Just one.”

“Scars? Stretch marks?”

These were hardly the questions Penny had anticipated but there was no backing out now. “No. None. I keep in shape.”

“Yes, I can see. How would your husband feel about you agreeing to model for us?

That would depend, Penny thought. She could foresee a situation that would meet with his wholehearted approval but nothing remotely close had been suggested yet. “Is there a reason why he shouldn’t agree?”

“It depends on the person. We have had difficulties. Jealousy mostly.”

“I would have to discuss it with Mark. And I would need to know what was involved.” Where were these questions leading was what Penny really wanted to know.

“Of course.” Frances made another note then looked into Penny’s eyes. “Lingerie photos, for example. Not all husbands would be comfortable with their wives posing in lingerie.”

“As I say, I would need to talk to Mark?”

“What are your own tastes in lingerie?”

When Penny hesitated, reminding herself that the black knickers and bra she wore were among her more expensive purchases from the heady days of Carla’s boutique, Frances said, “Please don’t be embarrassed. These are standard questions we ask all our potential models. If there are any you prefer not to answer, please say so.”

Penny remained silent. Although she felt the questions were becoming unnecessarily intimate she was curious to know where the interview was heading. Wasn’t this reminiscent of how things had started with Carla?

After a pause which she seemed to take as approval to continue, Frances prompted her again on the subject of lingerie.

“I suppose you could say I like a range, everyday wear and – well, certain things for special occasions.”

“Would you have a problem with being in front of the camera in lingerie?”

“It would depend, I suppose. If that was what was required or …”

“How about posing nude? Would you do that?”

Penny decided enough was enough. She simply couldn’t fathom Frances Stertori and she was beginning to suspect that she could end up being exploited for basic commercial reasons. Not what she had in mind at all. “I would need to know a lot more,” she said. But thinking that she had sounded prudish, she added, “It’s not that I have a closed mind. It’s just – ”

“Please don’t apologise. We are all inclined to be wary about anything unfamiliar, aren’t we? The thing is, we get a number of requests for people of your – style. Attractive, normal women. Not what I call manufactured models. And I believe you would fit the demand perfectly.”

Was it sincere? Or mere flattery? If she wasn’t to find here what she’d been secretly hoping for, she might as well settle the matter once and for all, get the woman to put cards on the table. But she was pre-empted. Before she could respond, Frances went on, “I think you have reservations and that’s no basis for us to proceed. So I’ll tell you what we’ll do.” She picked up the phone from the desk. “Alex will let you have one of our sample DVD’s. It will show you the kind of work we do, and then you can make up your mind. Have a look at it and then we’ll chat again.”

On the way out Penny collected the DVD. Somewhat to her surprise, she was asked to sign for it. The DVD was in a plain wrapper marked only Demo. Alex, on the other hand, was anything but plain: a striking blonde with high, small breasts and long legs. “We spoke on the phone,” she said. “It’s very nice to see you in person.” She smiled. “And I’m not in the least disappointed.”

**********************

At the first opportunity when Penny had the house to herself, she slipped the DVD into the player and sat down to watch. The screen showed a date a few months earlier followed by a plain white caption on a black background:

PRIVATE DEMO Not for public exhibition

FS/AW/GH/TT

FS was obviously Frances Stertori, thought Penny. AW might be Alexandra, GH could be Gary, the photographer. But TT? Before she could speculate further, the screen opened into colour. The scene is a bedroom. There is a large double bed with expensive pale yellow drapes. A woman sits at a dressing table. She turns to address the camera. It is Frances Stertori.

“This is a private video which will introduce you to the area of our work we hope will be of special interest for you. The receipt you signed when you collected it includes an undertaking not to communicate to a third party anything you see here. Please respect that, and please excuse the formality of this introduction.” With a deprecatory shrug, she rises from the dressing table before continuing. “Well, that was the necessary small print. Now I’m sure you are curious to see what I have in mind, and while a one-woman show has it’s merits we can do rather better with two.”

The camera cuts to a door which opens to admit Alexandra, though not exactly as Penny had last seen her. Alexandra is now naked from the waist up. All she wears are a black suspender belt, black knickers, black stockings and high heels. The camera zooms in to frame her upper half, displaying high small breasts slightly uptilted, the nipples dark and pointed. “Hello,” she says, smiling confidently into the lens. “You’ve already met Frances. And I’m Alex. I’m one of the lingerie models but I also act as Frances’s secretary. Although there is nearly thirty years age difference, we think we get along together rather well.”

While speaking she walks to where Frances stands in front of a full length mirror dressed, much as Penny remembers her, in a dark business suit. The two women kiss, a long, sensuous kiss during which the camera moves round behind Alex. It pans down and zooms in to show Frances’s hands cupping her young assistant’s buttocks.

They break apart. A close-up shows Alex’s face, the delicate high cheekbones, the complexion flushed, indicating already her state of arousal, the eyes closed. Frances’s voice is heard. “Ready?” Alex nods. She is seen full frontal. Frances is behind her, arms reaching round, hands fondling the tight little breasts. As Frances’s fingers begin to tweak the nipples, Alex gives a little gasp of pleasure. The camera instantly zooms in.

A second head appears in the frame of the picture. Frances has moved round to apply her lips and tongue to the stiff dark peaks. She licks and sucks. Alex moans softly.

In her chair in front of the screen, Penny turns back her skirt, slides her hand inside the waistband of her knickers. Her cunt lips are wet and slippery.

“My turn now.” Frances has spoken, easing Alex away from their lascivious embrace. Alex says nothing, knowing what is expected of her. Slowly, she undresses her employer, the jacket, the skirt, the navy blue bra, the matching knickers. The camera cuts away to show the pile of discarded clothing. When it returns, Frances is leaning with her back to the dressing table, supporting herself with her hands and bottom on the edge of the surface behind her. Her legs are wide apart. Alex is kneeling in front of her, running her hands up the older woman’s calves and thighs, into the inner recess. Her fingers find the labia, part them, expose the prominent clitoris. Alex licks her lips, bends her head forward and begins her ministrations. The camera cuts between wide angles and close-ups. Nothing is left to the imagination as Alex’s clever tongue alternately titillates and delves. A wide shot shows Frances with her head thrown back, heavy breasts rising and falling. Suddenly, her hands abandon their support on the dressing table to clutch at the back of Alex’s blonde hair, willing her to finish what she has begun. Alex pulls away, looks up. “Do you want it now?”

“Yes. Yes! You know I do.” Looking down she sees that Alex still hesitates. She sighs. “No. You’re right, as usual. You know what’s good for me. It will be better later.”

“It will,” says Alex. “On the bed?”

“Yes. Let’s not hurry it. Please.”

Penny, whose own orgasm was only narrowly avoided by this break in the on-screen action, reflects that the relationship between the two women in the bedroom seems to have subtly changed. It is Alex who is in control.

The next fifteen minutes confirm that thought. While the camera pries, an ever-present voyeur, frequently changing its perspective to disclose every intimate interaction, the participants give full range to their increasing lust. When Alex raises herself so that Frances can remove her knickers, the camera follows the silky material all the way to the floor. Then it watches as Frances kneels to allow Alex to conduct a fresh exploration with that educated tongue; this time she is gently but insistently probing the anal sphincter. Frances can be heard encouraging her.

They change positions, curling comfortably into a sixty-nine embrace, both mouths now greedily at work. There is though, Penny observes, a difference. Whereas Frances, who is underneath, is soon in the throes of passionate effort, thrusting her groin hungrily upwards, Alex is cool and calculating, occasionally raising herself to control the degree of her body’s inner momentum. Frances appears desperate for release from the raging heat radiating from a cunt inundated with her own juices and her partner’s saliva. Alex looks as though she is fully capable of choosing her own crowning moment. And, it soon becomes apparent, that will not be just yet.

“Time for Gary, I think.” Alex is sitting up, having extricated herself from her employer’s entwining limbs and avaricious mouth. “Wouldn’t you like that?”

“Of course I would. You know I would. But don’t make me wait. For God’s sake, Alex, get him in here. Get him into me. I need to be fucked. And I need it now.”

The camera shows the door through which Alex entered. It now opens to allow Gary to make his contribution. As with Alex earlier, this is not entirely the Gary Penny remembers from having her photograph taken. Gary has no camera now. In fact, he is naked and the only thing in his hand is his cock. It is large and protruding at an angle for forty-five degrees. He has been semi-preparing himself outside.

Alex takes Gary by the hand and leads him to the bed. Her pale skin and his shining blackness present a striking contrast. Penny takes in the possibilities of what lies ahead, forcing her fingers to cease their friction. Like Alex on the screen, Penny wants to be in control but she is not finding it easy. Briefly, she wonders, now that Gary is a performer, who is operating the camera. Maybe the mysterious TT. Irrelevant, she thinks, focussing her eyes and thoughts on the events about to unfold.

Frances lies in the middle of the bed on her back. Her legs are wide apart and her knees are drawn up. A close-up shows cunt lips gleaming with seeping moisture. Alex speaks to Gary. “Mrs Stertori wants you to fuck her. No need to hold back. She likes it hard.”

But Gary has his part to play, too. “Do you think this is good enough for her like it is?”

In close-up his impressive weapon is seen to be only semi-erect. Alex says, “We don’t want her to be disappointed. Let me see what I can do.” She gestures for him to lie on the bed beside Frances before kneeling at his side. She takes the black cock in her hand and licks the underside of the shaft up to the head. The sight of her white hand against the black flesh is almost more than Frances can bear. She groans with frustration. Alex opens her mouth and takes in a few inches of cock. Gary purrs, compliments her on her skill, tells her he can take plenty of suction, no danger of coming too soon. Frances puts her hand on her clit and rocks to and fro.

When eventually Alex releases the now fully erect member, she surveys the result of her technique with admiration. “Good,” she says. “Now fuck.”

Frances makes herself totally accessible, legs apart, knees raised, fingers holding open the portals to her inner secrets. Gary kneels between her legs, holds his cock in his right hand, steadies himself with his other hand on the bed and then drives his full length into the waiting cunt. He holds the position for a few seconds but Frances is demanding action. “Fuck me, Gary. Fuck. Do it now!”

Gary responds vigorously but, Penny notes, with clever variations of angle and pressure, each penetration drawing Frances nearer and nearer to her limit but no further. This is what she has been readying herself for, and soon she is moving in harmony with Gary’s firm assault. Alex, as the camera moves away to show, has found a vibrator and is on her back beside her employer plunging the phallus into her cunt while reaching underneath her body with the other hand to finger her arsehole. The sounds in the bedroom compose an erotic rhapsody: the buzz of the vibrator, the slam of flesh upon flesh, the resulting grunt from Gary, the slurp of a well-lubricated cunt each time he withdraws, the yelps of encouragement from Frances.

Suddenly, the older women cries out, “Now go for it, Gary, I’m nearly there. Alex, come with me.”

As Alex adds renewed vigour to his pounding, Alex rolls on to her side, tosses the vibrator aside and uses her hand to bring on her own orgasm while she sucks at Frances’s right breast. The effect is rapid and dramatic. With a long wail, Frances pushes her bottom up from the bed, closing her legs to hold the black cock in place while the intense sensation pulsates from her groin throughout her body. Gary, aware that he has achieved his objective, waits a moment until he feels the cunt muscles relax their grip. He withdraws, grasps his cock in one hand, jerks on the shaft and directs an arcing jet of pearly cum on to Alex’s face. Alex, with practised fingers, manipulates her own orgasm, in her own personal style, very controlled, very private, very internal. The camera fastens on Frances’s open mouth who is gasping through the wind-down recovery, then pans to Alex who is licking Gary’s cum from the side of her mouth.

The screen goes blank.

**********************

Late that night, when Penny told Mark about the video he instantly demanded to see it. Penny put the disc in the machine, pressed the play button – and nothing happened. No matter how they both tried, they couldn’t coax a single image on to the screen,

It was the first question Penny asked when she called Frances Stertori the following morning. The answer was indirect.

“Did you enjoy it?”

Penny admitted she had but had been frustrated in not being able to show it to her husband who was wondering if she had been hallucinating.

“Far from it,” said Frances. “But for our own security – and indeed for yours, too – that was a one-viewing disc. When the program was written, it included an instruction that at the end of the viewing it would self-wipe.”

While Penny said nothing, trying to absorb that information, Frances went on, “At least you will understand now the reason for my questions when you came to see us, and even more why it was best for you to have that introduction to what we do. Of course, we also do all the other things that are expected of a professional photographer, but this, as you will understand, is the lucrative side of our business.

“Now let me tell you how it works and what the safeguards are. We make videos to order. A client – and we have a substantial data base – supplies a scenario. We find the performers and film it. The client receives the video for his personal gratification. If he attempts to copy it, it will automatically self-wipe. Additionally, it will do the same after five viewings. Usually that is enough for the client in any case, but it also has the virtue of bringing him – or sometimes her – back to us with a fresh order.

“One other thing you should know. We do not supply clients in this country. All of our products go overseas. Where, I can assure you, there is considerable demand for performers who are mature and attractive. Like you.”

There was a pause.

“Would you like to pop in an discuss our terms?”

Penny said, “It will be a pleasure.”