Ann's Awakening Ch. 02

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Ann recruits her boss's wife to her lifestyle.
5.9k words
4.65
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Part 2 of the 2 part series

Updated 09/22/2022
Created 11/14/2006
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Calandria
Calandria
336 Followers

Ann's life had changed, and it had changed for the better. She had no sense of being a 'kept woman' even though Victor had provided her with her apartment. She paid him rent, and continued in her job – it was just that he took her out, and understood her urge to show her body off, to wear provocative clothing, and he wasn't jealous.

Finding the right clothes to suit her newpersonawas not always easy. She didn't have much trouble with her tops. Although tight blouses and jumpers showed off her prominent nipples to good effect, and she sometimes wore them, she much preferred loose, soft items, like silk blouses, which allowed her smallish, pointed breasts to jiggle when she walked. If she chose pale, plain colours, and light, translucent materials, so much the better.

Skirts were more problematical. She liked to wear flared silk or pleated cotton miniskirts, but they were not always practical, and were too revealing, even for Ann, and could be construed as indecent, in working environments, so she often settled for a simple full skirt, just above knee-length, which gave her a nice sense of freedom, allowing the breeze to waft around her shaven pussy, reminding her of her naked vulnerability, which she could heighten by inserting a pair of Chinese balls into her hungry vagina, keeping her 'on the edge' all day. Lately, she had experimented with a small-size rubber butt-plug, which she had had some difficulty in pushing into her tiny arsehole, even with the help of liberal quantities of lubricant. It hadn't been a great success, as she had not been able to keep the plug in place for very long, but Victor had suggested a different model, as he was eager to have her anus available to him, so she thought she would extend the experiment.

Ann's awakening had extended in another direction too. She had become interested in the concept of restraint. It wasn't, strictly speaking, an exhibitionist tendency, she knew, but the truth was that the tight skirts she had had to make herself were so form-fitting that they left nothing to the imagination, and nothing could be worn under them at all.

For day-wear, she made two skirts which were just below knee-length, so tight that she could only walk in tiny little paces, the effect increased by dint of the teetering needle heels she always wore. For evenings, she hobbled her legs in a sheath of silk, whilst her breasts were unfettered in the loose tops she wore. Victor had other ideas, and had given her a pair of tiny gold nipple clamps, which she had yet to try out. She had decided to save them for a special occasion.

Living in the apartment she rented from her lover pleased Ann so much that she asked him if she could extend her lease, and he readily agreed, then suggested they throw a sort of house-warming party to celebrate.

'That would be nice,' said Ann, 'but the flat is too small, surely?'

'Oh, we'll have it at my house,' he said, 'and we should call it a pyjama party.'

'But I don't have any pyjamas,' she protested.

'I know, so let's call it a nightdress and pyjama party.'

'That sounds better.'

They advertised it amongst friends, and at the Silk Traders' Club, where they had met, and Ann got her friend Tina to help get food and drinks organised well in advance. After giving it some thought, she even invited one or two people from work, including her boss, Justin, who she knew had the hots for her, and had an inkling of her taste in clothing. To all invitees, they made the 'dress code' for the evening clear.

When the evening came around, Ann spent a long time preparing herself, and when she walked into Victor's study, to find him sat in a pair of elegant silk paisley pyjamas, he was stunned at the sight of her.

'If I were anyone else, I would say that you can't possibly go to a party dressed like that,' he said, as she posed for him under the overhead light.

She wore a long shimmering silver transparent nylon nightgown, with spaghetti straps, deeply cut away between her breasts and at the back, and tied at the waist with a silver ribbon, the ends of which hung down behind her. Her feet were in silver high-heeled mules, and through the nightgown's material could be seen a heavy silver chain she had draped around her slim waist. Less obvious was a more delicate chain she raised her skirt to show Victor, that she had clipped to her clit ring at one end, and her waist chain at the other. Anyone looking closely enough at her would be able to see it through the gown.

'God, you look fantastic, Ann,' said Victor, and massaging her breasts through the gown would certainly have led to a pre-party fuck, had not the door-bell rang there and then.

It was Tina, with a long black cape wrapped around her like a vampiress in an old movie. When she stepped into the study, at Victor's invitation, she whisked off the cape in a dramatic gesture and was left wearing scarlet nylon baby doll pyjamas with a fur trim at the neckline and hem, which was at waist-level. The tiny matching panties were as sheer as the top and were tied with ribbons at the hips. She wore four-inch heeled stilettos, and heaps of jewellery.

'Wow,' said Victor, 'you look great Tina, too. If all the girls look like you two, I'm not going to be able to move from the chair in these pyjamas.'

Ann ran her hand down his trouser-front and found the reason. His pyjamas had a big slit at the front, and he wore nothing underneath – he had taken the pyjama-party idea seriously!

Asif and Lisa turned up soon, Asif, slim and dark in short pyjamas, and Lisa in a long, flowing black silk nightgown, completely backless, which contrasted beautifully with her extravagantly long blonde hair.

'Who the fuck are they?' asked Tina, who had never met Lisa and Asif before. When Ann told her, she whistled and said, 'I'm going to have to go to bed with the both of them before I'm much older!'

'From what I know of them,' said Ann, 'I doubt you'll have much of a problem!'

Soon, guests were rolling up, clad in fur coats and wraps, which they left on the tables in the entrance hall, as they entered the well-heated and spacious lounge, where they had music playing.

All the women were in nightgowns, mostly transparent or flimsy silk affairs, whilst the men wore silk pyjamas. It made for very interesting dancing!

Ann was just starting to enjoy herself, dancing with a variety of hunky men, when in walked her boss, Justin Price – she hadn't really expected him to appear. He was clad in loose silk pyjamas, and held the hand of a lady who was, presumably, his wife. Ann had never seen her before. She had rich auburn, shoulder-length hair, and wore a very classy looking peach-coloured long nightgown, which might have been Janet Reger. Ann and Victor greeted them at the door, and Victor made sure they were supplied with drinks, but Justin's eyes were for no one else but Ann, and, as a slow number had just been put on the sound system by Tina (by accident or design) he asked her to dance, while Victor led his wife, Sarah, into the crush on the floor.

Instantly, Justin's hand went to Ann's near-naked buttocks, and as he pressed her to him, she felt the entire length of his rampant shaft thrusting against her belly.

'You're a naughty boy, aren't you, Mr Price?' she said.

'I'd very much like to be,' he replied, and she wriggled against him, the points of her breasts rubbing his chest, as he nibbled the lobe of her ear.

Tina, in charge of lighting now too, turned the lights down really low, as the highly inappropriate 'Three Times a Lady' played, and Ann risked reaching down through the slit in his pyjamas, and briefly running her palm around the crown of Justin's torrid erection.

'Oh no,' he moaned, 'do that once more, and I'll cum, right here!'

She desisted, and, peering through the darkness, saw that Victor was sat with his arm around the shoulders of Sarah on a sofa beside the dance floor, deep in conversation.

When the music changed to another slow number, she saw that Tina was now dancing with Asif, and, as they passed close by, she noticed with a shock that Tina's panties were now missing. Then she saw the red ribbon trailing from the top pocket of Asif's pyjama jacket.

'You cow!' she mouthed to her friend, who smiled back knowingly.

When, as she disentangled herself from Justin after the dance had finished, she looked around for Lisa, she saw her sitting on a couch at the back of the room, holding hands with a tall black girl in a white negligee, who must have come from the Silk Traders' Club, because Ann didn't recognise her. Curious, she watched them out of the corner of her eye for a minute, and the black girl leaned across and kissed Lisa, long and tenderly, stroking her long blonde hair, while Lisa's hand sought the black girl's breasts through the thin nylon of her garment.

Ann's reverie was suddenly interrupted by Victor. 'Pretty sight, they make, don't they?'

'Yes,' she replied.

'I've been talking to your boss's wife.'

'I know, what's she like?'

'She's OK, but inhibited. She's seen the effect you have on her husband, and wants you to help her. Will you?'

'Of course, but on one condition.'

'What's that?'

'That you fuck me, now!'

'Then I have a condition of my own.'

'Oh yes, and what's that?'

'Come on, you'll see!'

He went over. Leading her by the hand, first to Tina, to ask her to keep things going, then to Sarah to tell her that she had agreed to help her, and then he led her up the wide staircase, several pairs of eyes following them as they went, knowing full well what was their mission.

When they got into the privacy of Victor's bedroom, he flipped the lock.

'Now what's the condition?' Ann demanded.

'On your knees!' he told her, and she knew what his condition was. It was what they had both wanted for so long. Maybe she was ready for it – she wasn't sure. Her cunt was wet through, with the excitement of wearing the nightgown and showing off her body all night, the dancing with so many men, the feel of Justin's hardness against her. She had worn a butt-plug several times, so it wasn't as though her arsehole was completely virgin, and yet.....

Ann felt the fear of anticipation, as she knelt in front of his couch, her breasts cushioned on the soft upholstery, and he gently eased her legs apart, then threw her nightgown up over her waist, and trailed his hand the length of her soaking slit, toying for a moment with the ring in her clit hood, and then teasing her clitoris to erection, before poking two fingers easily into the steaming hot depths of her cunt.

His fingers traced her slit again, this time running up towards her arsehole, finding the puckered entrance. He rammed a finger deep within, and she knew something approaching total ecstasy, but was also aware that she should have to endure terrible pain when his thick cock penetrated her.

Two fingers, then three, worked their way into her, and tears flowed from her eyes as he violated Ann's tender arsehole, passing her sphincter with the aid of lubricant.

'You're ready, darling!' he told her, and, before she could protest, he was kneeling behind her, his knob forcing its unstoppable way into her virgin anus. Ann screamed with pain as he passed her sphincter, and knew the real meaning of passion for the first time in her life when a tremendous orgasm welled up and sent her to heaven. She came again and again, screaming, calling him names she should never recall, as he drove his great rod into her, tearing her, hurting her, she didn't care. Then she felt him stiffen and knew the joyous warmth as his hot load shot up into her bowels.

'Oh, Victor,' she said, 'why did we wait so long?'

The next day was Saturday – just as well, as she needed a couple of days to rest her sore arsehole, and cleaning the house up was no easy task either.

On Monday, almost as soon as she got to work, Justin called her to his office.

He sat behind his big desk, in sports coat and striped tie, and Ann came in, in her usual pleated skirt and silk blouse. They must have looked like just about anyone's idea of boss and secretary.

'Hi, Ann,' he said, 'my wife says you're going to help her.'

'If that's what she wants,' she said.

He looked at her in a strange way, and said, 'Look, Ann, can we forget our dance the other night? I mean, I fancy you like mad, as you know, but there are things you mustn't do on your own doorstep, as you know, and I think the world of Sarah.'

'OK, said Ann, 'I understand. How can I help? With your wife, I mean.'

He looked relieved. 'Right, here's what I want you to do. Take the day off work tomorrow, and spend it with her. She wants you to help her get a new wardrobe, will you do that?'

'Delighted,' said Ann, and left, clutching directions to Justin's home.

Next day was warm and sunny, so as Ann didn't have to go into the office, she decided on a pleated mid-thigh maroon cotton miniskirt, with a loose printed silk blouse. She wore a satin garter-belt and long white lace-top stockings, cinched to the straps, and metal-heeled stilettos.

When the Sikh taxi-driver opened the car door for her, she caught him admiring her legs, so she deliberately gave him a brief glimpse of naked pussy as she swung her into the seat. He gulped, and she saw him desperately trying to see her in his rear-view mirror during the short trip across town. She tipped him well.

Ann arrived at Justin's neat town-house at around ten to find Sarah waiting for her, dressed in jeans and tee-shirt.

'Would you like a coffee first?' she asked.

'That would be nice,' agreed Ann – anything to set the obviously nervous Sarah at ease.

As Sarah got the coffee, Ann sneaked a good look at her. She was not really pretty, but had strong, even striking, features, with huge almond eyes, and an aristocratic set to her face, She had a good body, with a slender waist and long, slim legs.

'Justin said you'd help me choose some clothes which would – er...do something for him,' she said.

'Of course,' said Ann, 'but it's a much a matter of attitude, Sarah.'

'How do you mean?'

'You've got to be prepared to show yourself, at your best. Are you?'

'I......I don't know.'

'Look,' said Ann, 'there's just the two of us. This is what I mean.' She lifted the hem of her skirt just enough so that Sarah could see her shaven mound, and further accentuated the act by running a finger lazily up her thigh, just to the very start of her naked slit.

Sarah's mouth dropped open, and her big eyes grew bigger still.

'Oh my God,' she said, 'you go into my husband's office like that! I ought to throw you out of the house, but..........but, well....he's so open about it, and so are you, Ann. I can't help but admire you. Let me go and think for a few minutes, will you!'

She stood abruptly and walked out of the room. Ann was left wondering what was going on in Sarah's mind.

In a few minute's, however, she was back, smiling.

'I've had a good talk to myself, Ann,' she said, 'and it's not just that I want to keep my husband. In fact, I'm not even sure I do, between ourselves, as I have independent means, but I loved the scene at your party, and talking to your Victor.......' She let the sentence hang, then she continued, 'so, tell me what I have to do!'

'First,' said Ann, 'get out of those jeans. Let's see you in something more revealing, and then we'll have a look at what you have, and what we need to go and buy. How's that?'

'Come on upstairs, then,' she said, 'you can have a look at my wardrobe.'

As they had quite a large house and no kids, Sarah had her own dressing room, and Ann admired the big, mirrored wardrobes, as Sarah slipped off her jeans and tee-shirt. She stood, looking a bit awkward, in a pink bra and matching panties. Ann looked pointedly at her, and she nervously reached behind her and unclipped her bra, shrugging the straps from her shoulders. Her breasts were firm and nicely formed, with well-centred pink nipples.

'Don't be shy!' said Ann, and Sarah hooked her thumbs under the waistband of her panties and eased them off over her nicely-rounded buttocks, letting them fall to the floor, where she stepped out of them. She was naked but for her bedroom slippers.

'Well?' she asked, 'what do you think?'

'I think you've got a lovely body,' said Ann, 'and you ought to enjoy showing it off, but just one thing.'

'What's that?'

'We ought to do something about this!' Ann reached out and touched Sarah's bush of pubic hair, which grew in a dense forest all around her mound and in long wisps right up between her legs.

'Oooh!' she said, but meekly allowed herself to be led to the bathroom.

Ann sat Sarah down on a plastic stool, and rummaged around in the bathroom cabinet until she found scissors, shaving cream and two plastic razors, then she ran a bowl of hot water and set to work.

First of all, she used the scissors to clip away the majority of the hair from the whole of Sarah's pubes, getting her to open her legs and working her way right around to her arse. Then she lathered the whole area thoroughly and set about shaving every last vestige off hair from, firstly, her mound, then around her labia, then right up her crack to her arsehole, taking care to ensure that not a single hair remained.

'Now you must make sure that you keep shaving every two or three days, or it will itch, and stubble will grow,' she said, as she anointed the whole area liberally with aloe vera lotion. As she smeared the lotion around sarah's labia, she let her fingers linger a moment, teasing her, drawing a little involuntary 'Oh!' from Sarah's lips.

'What does it feel like, Sarah?' asked Ann, as the other woman stood up and walked about naked.

'Funny,' she said, 'kind of.......well, naked!'

'Wait until you are dressed,' said Ann, 'you'll feel lovely!'

It was time to inspect Sarah's wardrobe, and Ann prepared to be critical. She asked Ann if she was really serious about what she was doing, and Sarah replied that she was. However, having a quick look at the vast array of clothing that Sarah had in her wardrobes, Ann told her that she was proposing simply to put aside the things of which she didn't approve in one wardrobe, keeping the other two for things she considered 'appropriate' to Sarah's new lifestyle. She would do the same, she said, for her underwear drawers.

Into the third wardrobe went all Sarah's trousers and trouser-suits, evening dresses which Ann considered too boring, and many skirts which were, in Ann's view, 'neither one thing nor the other.' She was left with very few clothes in the other 'appropriate' department, and the third wardrobe was full to bursting.

When she attacked the underwear drawers, all panties were discarded immediately, and all but one or two bras were similarly tossed out. The ones that survived did so because they were 'platform' models, leaving the nipples entirely free. Ann found two garter-belts and some nice stockings, and kept these.

She turned her attention to shoes, and threw out all but three pairs, two of which Sarah said she'd bought for weddings, and one pair she said she'd forgotten she had. They were all stilettos, with at least three inch heels. Ann didn't like them very much, but decided they'd do at a pinch.

'Right,' she said, to Sarah, 'let's get ready and go shopping – perhaps have a bite of lunch out. It's a nice day; a shame to waste it, eh?'

Sarah agreed, and Ann laid some clothes out for her. It didn't take long.

'But.....but – I can't go out in just those!' said Sarah, waving at the skirt and blouse Ann had laid on the back of the chair.

'What do you think I'm wearing?' asked Ann.

Doubtfully, Sarah slipped on the cream silk blouse, and stepped into the blue cotton skirt, which was about four inches above knee-length. When she tucked the blouse into the waistband, Ann stood back to have a look at her.

Calandria
Calandria
336 Followers
12