Penny's Progress

This story is dedicated to the real Penny who requested it, inspired it and helped to shape it. The people and events portrayed, however, are the product of the authors' imagination.

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Most women have a secret indulgence: chocolate, maybe, or shoes; jewellery for some, soap operas or magazines for others. Penny's indulgence was lingerie, and where lingerie was concerned she had firm principles, which didn't include thrift. Her underwear wardrobe was extensive, varied and expensive.

Penny was thirty-seven. Her large breasts were firm and looked good in bras that made the most of her nipples; her round arse was at its most provocative in silk or satin; she liked tight sheer panties that moulded the mound of her vagina and the cleft of her shaven labia, though there were times when she wanted them half concealed in french knickers that allowed easy access for exploring fingers. Curiously - and she was unable to explain this to herself - she found white cotton helped when she was preparing to masturbate. Variety contributed much to her sex life. Penny liked to fuck and be fucked and she knew how to turn on a man - usually Mark, her husband, but not always.

Much of her intimate shopping was done by mail order, but one day she saw an advertisement for the opening of a new lingerie boutique called Intime. Although the opening times were conventional she was intrigued by a note that clients could be seen by appointment out of hours. The voice that answered when Penny phoned was feminine, polite and unassertive; no hint of a hard sell. After she had given details about herself, they agreed an appointment the following day.

"I shall look forward to meeting you," said the woman. "My name is Carla and I specialise in offering a personal and completely confidential service to my clients. That's why I prefer the appointment system. Where lingerie is concerned, privacy is preferable - don't you agree?"

Penny decided not to tell Mark until after her first visit; perhaps she would return home with a pleasant surprise for him. It didn't occur to her that she herself was embarking on a course of action that would lead in time to a very pleasant surprise.

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Carla was a well-preserved woman of about fifty, Penny guessed; a slim brunette wearing a dark, tailored suit over a white blouse. A knee-length skirt and black stockings emphasised shapely calves. They were seated in an upper room where Carla had offered coffee or wine. After a brief exchange of small talk, Carla said, "Do you have anything specific in mind or would you like to see my catalogue?"

Two large loose-leaf tomes were produced. "These," said Carla, indicating the first, "are my conventional lines. Everyday underwear. But, of course, tailored to make the most of your assets. That explains why my prices are not exactly High Street."

Penny turned the pages of photographs of models, of various ages and shapes, modelling bras, knickers, bodies, pantyhose, stockings - a comprehensive selection.

"And then I can offer a wide range of high quality wear for more special, more - " she paused" - intimate occasions. I like to stress the quality of these items - there is so much inferior material offered via the Internet, or in sex shops. This is not a sex shop. I'm not, for example, in the rubber or leather trade. I only offer materials - silk, satin - that are guaranteed to make the wearer feel - well, let's not mince words, sexy."

The second book, even larger than the first, fully justified Carla's claim to offer seemingly unlimited choice, but if Intime was not a sex shop it was certainly able to compete in that market. Models displayed peephole bras, miniscule bras, open crotch knickers, crotchless pantyhose, suspender belts, basques, slips that looked conventional until certain see-through areas became apparent; everything, it seemed, designed to emphasise, albeit subtly, a woman's most intimate features.

Thinking about wearing some of these garments gave Penny a familiar tingle. But she was embarrassed to find that each time she looked up from the pages she had been turning her eyes met Carla's. The woman's smile may have been no more than her professional demeanour, but afterwards Penny found herself wondering if there had been something more.

Carla said, "Please don't feel under any obligation to buy now. You may want to think about it, talk to your partner. Then you can order by telephone."

"Yes," said Penny, "I think that would be a good idea."

"Shall we just take some measurements? Then we needn't trouble you again."

"Yes. Of course. Shall I ...?"

"Just slip off you dress, if you will. It will only take a few minutes."

Pleased that she had come prepared for this possibility, Penny still felt a little apprehensive as she stripped down to black bra, french knickers and hold-ups. Carla stepped back a pace to assess Penny. The strange half-smile flitted across her face for a moment before she spoke.

"Well, Penny, there's plenty there for us to work on, isn't there? I must say i envy you your legs - for more intimate moments I would certainly recommend suspender belts. Black against your skin will be excellent. But let's start with the bra."

She stepped forward with a tape measure, made a note on a pad, then placed her hands gently under Penny's breasts. "You will obviously be grateful for some support there, but we won't need anything excessive."

Carla's hands remained in place but Penny said nothing.

"I need to ask a question you may feel intrusive - so I won't be offended if you decline to answer. I just wonder if you are interested in peephole bras? many of my clients are."

Penny took a deep breath, then nodded.

"In that case, I shall need to be clear where to insert the apertures." She paused. "Would you mind if I asked you to stimulate the nipples for me?"

Nothing had prepared Penny for this moment and she was surprised, thinking about it later, that she acquiesced so readily. Maybe her secret tingle was prompting her. In any case, it needed no more than a little stimulation between thumb and forefinger to produce an effect. Carla nodded dispassionately, took more measurements, made more notes.

"Thank you," she said. "Now the knickers. Do you always wear french?"

"No. Not all the time. It depends on ... the occasion, my mood, you know." There was a new confidence in her voice. Penny's nervousness had given way to a kind of suppressed excitement. This was not diminished when Carla walked behind her and ran her hands gently over the curves of her bottom. Penny held her breath while the older woman made more checks with the tape measure. There was a moment when she felt the slightest suggestion of pressure between her legs, but Carla's hands moved on and another note was made.

Finally, she said, "Thank you, Penny. I think that's all. Take your time to think over your needs - I like my clients to feel completely satisfied. When you are ready, pop in and see me again - or just telephone. I'll give you my card."

While Penny dressed, Carla went on, "I've really enjoyed meeting you, Penny. And I shall look forward to being of service."

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During the following months, Penny became one of Intime's most frequent clients, adding to her extensive lingerie wardrobe a number of items, all chosen from Carla's second catalogue, that received Mark's enthusiastic approval.The new garments also had successful outings when Jason, a friend they had found on the internet, joined them for a threesome.

If that was predictable, Penny was aware of a less foreseeable consequence that affected her masturbatory habits. A high sex drive had always led her to seek self-relief on days when there had been no other sexual activity. It was her custom to indulge when the house was empty. She would sit in a favourite armchair that allowed her to lift her skirt, spread her legs and slide a hand inside the waistband of her knickers. Replaying in her mind a recent session with Mark or, better still, their latest threesome, she invariably had no difficulty in inducing her orgasm, sometimes repeating if the sensation was particularly intense.

However, as her visits to Intime developed, Penny found an entirely new source of stimulation surfacing from her subconscious mind. She abandoned the white cotton that had previously accompanied her masturbation. Instead, she wore knickers from Intime. The images that came into her mind were no longer of her husband or Jason, but of women acquaintances. Most frequently, Carla. The swinging Penny had done with Mark had involved other men, but now she began to consider how she might react to another woman.

Then, one day when she was stroking her clitoris very slowly to prolong the pleasure, the phone rang. Penny swore, considered ignoring it, but eventually had to respond to its summons. To her surprise, the voice at the other end was Carla's. Unthinkingly, she said, "Oh, Carla, I was just thinking about you."

"Ah. Did you have a new order for me?"

Hastily she ordered her thoughts. "Well, not exactly," she said, "I was only thinking it was about time I refreshed my wardrobe. There's no hurry." Then it occurred to her that Carla had originated the call. "But what can I do for you?"

"Well, I was just ringing to say that I'm having a little get-together for some of my special clients, and I was hoping you'd be able to join us. Next Thursday at about two-thirty, if that would suit you. I shall close Intime at noon and we can meet at my home - I'll give you the address. We'll take the phone off the hook and have an enjoyable afternoon, all girls together. Do say you'll come."

Penny, in her high state of self-arousal, her pussy still wet, masturbation incomplete, didn't hesitate.

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Where Carla lived was where the well-to-do lived behind high walls guarded by security cameras. The house, its wide wrought iron gates open, was approached by a sweeping drive. Parked cars told Penny that she was not the first to arrive. Carla greeted her with both arms, kissing her cheeks. Just for a moment, Penny sensed that her hostess's hands brushed across her, registering the protruding nipples beneath the soft material of her blouse. Her suspicion was confirmed when Carla murmured,"How very nice. I'm so pleased you were able to join us. Come and meet the others."

Three other women were present in a spacious, tastefully furnished sitting room. Two, side by side on a couch, were attractive brunettes, twenty-somethings, casually but expensively dressed. The third, who smiled up from a deep armchair, was closer to Penny's age.

"This is Penny," Carla indicated with an immaculately manicured hand. "This is Toni, and this is Miranda - " (the two younger women) " - and this is Sonia."

Nods and smiles were exchanged. "And now we're all here, I'll just close the shutters. If you are going to show off your outfits a little privacy won't hurt." While Penny reflected that nothing had been said to her about showing off outfits, Carla pressed a button in a hallway and shutters rolled noiselessly across the windows from the outside while heavy drapes were closed inside. At the same time the room was illuminated by a series of subtly-placed spotlights and wall lights.

"Now, Penny, make yourself at home." Carla guided her to an armchair facing Sonia who immediately crossed her legs, allowing her skirt to rise several inches above her knee. Sonia, with her light brown hair swept back, was neither beautiful not plain. Behind the counter of a bank or the reception desk of an office she would have blended easily into her surroundings. Yet when their eyes met, Penny looked away, uncertain how to respond.

Carla turned to Penny. "We were talking when you arrived about some items I'd had made for Toni and Miranda, and I was about to ask if they had been well received at home. Which was the point, I take it?"

"Well, yes and no." It was Miranda who answered. "There was each other, too. But this is the first chance we'll have had to find out." She looked at Toni and put a hand on her friend's thigh. Then she turned to Penny. "I take it you won't be shocked, Penny, to learn that Carla organises these occasional little get-togethers for married women who also have - other interests. Or did Carla already mention that?" She looked at their hostess who merely shrugged her shoulders, as though by now it was unimportant. Penny, her mind already pulling her in several unprecedented directions, said nothing.

"So we'll start," Miranda continued, pulling Toni to her feet.

For the first time Sonia spoke. "I've been looking forward to this. But if you don't mind, I'll sit next to Penny. I know how it feels to be here for the first time." She took a cushion and sat on the carpet beside Penny's chair.

In the middle of the room, Toni and Miranda had begun to undress each other. When skirts and tops had been removed they stepped apart to survey each other. They were wearing undie sets that were identical in all but colour. The bras were a clever confection of silk that lifted the breasts with the minimum of cover; Miranda's nipples were pink and round, Toni's brown and more pointed. The knickers were crotchless, revealing in Toni's case a shaved pussy, and in Miranda's a neat triangle of black pubic hair. Both wore suspended belts and fine stockings. Toni's outfit was lilac, Miranda's cream.

"Two of a kind," said Carla with a chuckle. "I didn't want to spoil the surprise and tell you that quite by chance you had both made the same choice from my spring collection. But I have to say, you both look gorgeous. Don't they?"

"Wonderful," Sonia agreed. Penny could only nod, unable to trust herself to articulate the thoughts competing for the forefront of her mind. While she couldn't take her eyes away from the two half-dressed women who had begun to caress each other, she was conscious of an awareness of Sonia sitting at her feet.

Miranda dipped her head to begin licking Toni's nipples. Ton's response was to tease her way into the opening in her friend's knickers. When Miranda sighed with unconcealed pleasure, Penny bent forward for a closer view. The tingle in her groin asked its familiar question. The answer was masturbation but Penny was in a situation where she didn't know the rules. But nobody, surely, would mind if she slipped her hand inside her knickers ...

Toni had taken Miranda to the couch, lowered her on to her back, opened her partner's thighs and buried her head between them. As her tongue began to explore the warm dark depths, Miranda co-operated by pressing her groin upwards and placing hand on the back of Toni's head to intensify the contact.

Breathing deeply, Penny leaned back and found that her fingernails were digging into the fabric of the armchair. A moment later a quiet voice in her ear said, "Relax, Penny, relax and enjoy. Keep watching." Carla had moved behind her and was gently massaging the back of Penny's neck and shoulders. Gradually the tension eased and Carla murmured, "Let me help you." Bending forward, she slipped both hands inside Penny's blouse, insinuated fingers until they encountered the prominent nipples. "Ah, yes," said Carla, "the peephole. I thought it was."

This was the experience Penny had so often conjured in her fantasies, but was she ready to surrender totally? The gentle tweaking by Carla's fingers was having its effect. Penny closed her eyes and waited to see what would develop.

What happened next was another surprise. While registering that Carla was easing her out of her blouse, Penny became aware of a hand stroking her calf. Opening her eyes she saw that Sonia had turned her back on the pair on the couch and was kneeling between Penny's feet looking up at the breasts now fully exposed by Carla. Capitulation followed quickly. Aware that this was what she had longed for, Penny lifted herself slightly from the seat. Sonia needed no further encouragement. "Penny," she said as she slipped the skirt down willing thighs, "we can make this very nice for you. Is it the first time?"

Penny nodded. She had been stripped to her black french knickers, suspender belt and stockings. She was ready to accept whatever the two women had in mind.

First, Carla moved round the chair, still concentrating on stimulating Penny's breasts while Sonia undressed. As one garment after another was removed, folded and carefully laid aside, Penny let her hand rest between her legs. She knew she was wet; her clitoris was begging for her touch. Seeing this, Sonia said, "Good, Penny. I'll take over in a moment while Carla makes herself more accessible. Then we'll be better on the floor with some cushions."

Soon all three women were naked, Penny on her back with cushions beneath her head and her bottom. When it began, it was Carla's tongue that returned to her nipples, Sonia's hands that lifted her knees, widened her thighs, Sonia's fingers that opened her labia, tested the seeping inner folds with two digits, then three. Teeth gently nibbled an exposed and distended clit. Soon Penny began to writhe and moan; the signs were understood and the arousal was allowed to slacken off.

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

"Yes," said Penny. "Please keep doing it."

"Can you repeat?"

"I think so." With Mark she usually could and she was beginning to believe that in the present situation,too, multiple orgasms were exactly what she wanted. At that moment a series of sobs from the couch signified that Toni had taken Miranda to the point of no return. After the briefest recovery pause, they changed places and Miranda set to work on Toni. On the carpet, too, there was a realignment. Carla took over licking Penny's vulva while Sonia turned her attention to Penny's breasts, but with a different approach: firm hands moulding the orbs enabled Sonia to keep her balance while squatting across Penny's face. Instinctively, Penny understood. Using her hands to support Sonia's buttocks, she lowered the woman until she was able to probe her pussy with the tip of her tongue. From somewhere above, she heard Sonia cry, "Oh, yes. Yes!"

There were more changes, more variations, sometimes with vigorous penetration, more often with minute permutations of pressure and rhythm until at last Penny could control herself no longer. "Please," she said, "I've got to come now. Please do it for me now."

Even afterwards she couldn't be sure which of the two finally induced the climax. With her head thrown back, eyes closed, fingers clenched she embraced the explosion inside her, willed it to throb throughout her body until it gradually subsided into a delicious pulsing somewhere in her pussy.

Carla and Sonia watched as Penny came back to earth. Sonia said, "So how was the first time?"

"Amazing."

"Different?"

"Yes, I think so."

"Do you want to do it again?" This was Carla, smiling approvingly.

After a pause, Penny said, "Yes. I easily could. Though not now. That was very special and I'd like to remember it just like that. But I hope you will invite me again."

"Of course. But just because you've finished for the moment, doesn't mean that we have to. Why don't you just watch for a while - help yourself a little if you feel inclined. Nobody here minds. And what happens here stays here."

By the end of the afternoon, Penny had seen much and learned much, marvelled at the appetites of the four women who enjoyed each other in every possible combination. She noted that while Toni and Miranda gave and received with uncomplicated abandon, the participation of the two older women was infinitely subtle and concentrated, their orgasms less obvious but quiveringly intense and, in Sonia's case, skilfully prolonged. It was while watching Sonia that Penny found herself bringing on her own orgasm.