Upping the Ante Ch. 01-02

[This story is the latest in the series of stories about Margaret, the shy widow next door, and her evolving relationship with her new Master Will. It has many aspects and could have also been listed under the Mature, Anal, Exhibitionism, and BDSM categories, among others. It has references to bodily functions, so if that bothers you, I suggest you read no further. All characters in this story are well over 18 years old.]

chapter 1

Margaret's Old Friends Come Visit and WTF?

It was now over a month since Will had met Margaret, the shy widow who had moved into the apartment next to his in their apartment complex. Things had rapidly heated up as they realized they shared a deep interest in dominance and submission. Margaret had enjoyed an array of fetishes and kinky sex with her late husband Paul for two decades, and was plunged into a deep void left by her sudden bereavement. Once she discovered that Will, her much older neighbor, was a devotee of the same depraved and exotic practices and was understanding of her desperate needs, she happily gave herself to him as her new loving Master.

Will, for his part, was utterly charmed with Margaret's quirky ways. Her deep shyness expressed itself in a coping strategy of an attachment to propriety, to protective layers of lingerie and foundation garments, and to personal dignity at all costs, which made her susceptible to humiliation, embarrassment, and mortification at every turn. Perversely, it was those emotions that fueled her craving for debasement and exquisite punishment leading to ecstatic release.

She was undoubtedly a "piece of work", requiring skillful handling. Unsurprisingly, this was too weird for most men to take on, but Will had risen to the challenge with a droll aplomb, and a knowing intuition of how best to stoke her fires, yet tamp them when required. It was a delicate dance that they were still both learning.

* * *

Now that they were "an item", they'd taken to spending much time in each other's apartments, a situation that made them wish they could just cut a doorway through their adjoining walls and have a roomier shared space. Of course, the property owners would never allow such a thing.

The next best thing was to act as if their apartments were a two-part suite, in which either was welcome. Of course, there were certain limits to this arrangement. Margaret gave Will a duplicate of her apartment key, granting him access to her space at any time under any circumstance. That was Will's prerogative as her Master.

Margaret, however, had to knock on Will's apartment door and request entry. Moreover, she was required to walk the short distance from her apartment to his door, clad only in her slip, bra, and pumps, knocking and waiting for him to answer, anxious all the while that another neighbor might spy her nearly-naked in the hallway. This arrangement mortified Margaret, of course, but it also excited her and made her pussy drip.

Will also gave a specific guidance to Margaret for her journeys out into the neighborhood to go shopping or to the library or to other public venues. Recognizing that Margaret received solace and comfort through wearing her striking wardrobe of '50s-style lingerie, foundation garments, stylish dresses and lovely high-heels, she was required to be thus attired when out and about, with the added condition that she have either a modest butt-plug in place or a devilish chastity belt with twin quim and anal pegs inserted. This gave her a certain halting gait, especially when she wore tapering ankle-length skirts, and 4-inch heels that restricted her walking to almost comically mincing mini-steps.

The poor woman would return from such expeditions in such a state of humiliated arousal that Will was forced to have her disrobe immediately and then would briskly apply a quirt to her buttocks, both to bring her off and to bring her back down to earth again. Margaret was a complex woman, but Will seemed to grasp her needs.

* * *

All this continued as a rather comfortable arrangement for some time, and then one day Margaret came knocking at Will's door in only her slip and bra and almost leaped upon him hugging and kissing him when he let her in.

"Well, my pet, what has you so excited?" Will queried. "This is most unusual."

"Oh, Master, I just heard from my dear friends, Constance and Neville Smithers, and they hope to pay me a visit. My husband and I used to play very naughty games with them sometimes, back before Paul became ill, and when we were able to invite select friends for a weekend of deliciously bizarre eroticism and taboo behavior. Connie and Nellie were just the best - so outrageous, and yet so poised - can I invite them to stay for a weekend and play with us? It will be super-fun!!"

Will was intrigued. He was hardly through with familiarizing himself with Margaret's fetishes and past history, but this sounded like an opportunity not to be missed. He knew little about Margaret and Paul's side-pastimes, but he sensed that this might be an introduction into Margaret's deepest kinks. He nodded his approval.

"Oh, thank you, Sir, I promise you won't be disappointed. Connie and Nellie are . . . well, you'll see. There is really nobody else like them!"

* * *

Margaret worked out the arrangements and before they knew it, the exciting weekend was upon them. Will and Margaret conferred and decided that Connie and Nellie would sleep in Margaret's apartment during their visit, while Margaret would sleep with Will. That afforded the couples a certain modicum of privacy, but also an intimate proximity.

The visiting couple rang up Margaret's phone to let her know they had arrived and were just outside the front entrance to Will and Margaret's apartment complex. The hosts went down to help bring up their guests' belongings in the elevator, and they soon had all the baggage piled into Margaret's apartment. It was an impressive load, as if the guest couple had plans to stay a week, or plenty of equipment to stage an elaborate kinky scene. Margaret and Will were prepared to deal with either possibility. This was a special occasion, soon to warp beyond anything either anticipated.

* * *

Constance - or "Connie" - had a unique presence. She looked to be near Margaret's age, in her early forties and very self-possessed. Her makeup was impeccable, with carefully shaped arched eyebrows, rouge accenting her high cheekbones, dark eye shadow and mascara, and an oddly cruel mouth accentuated by black lip gloss. Her hair was jet black and bobbed like a flapper's of the 1920's. Her aura was not that of a bull dyke, however, but of a quite feminine Domina who was used to getting her way, and would reward those who pleased her.

She was not especially tall, perhaps 5' 8", but there was something curiously odd about her body's shape beneath her billowy pleated dress. It gave the impression that she wore a bullet-proof vest, or perhaps an umpire's protective padding. Her figure was formidable, but muted, as if she was carefully wrapped up to avoid displaying too much of her physique. Will's curiosity was piqued. What was that all about?

Her husband Neville - or "Nellie" - looked to be the same height as Margaret, 5' 3", and of delicate build. Extremely self-effacing, he made shy Margaret seem gregarious by comparison. He had an effeminate air about him, enhanced by a light patina of makeup and natural looking pink lipstick. Nellie gave the clear impression that he would acquiesce to whatever his wife, or anyone else, told him to do. For all that, he was a very pleasant fellow and quite lovely to look at.

There was no question that Connie and Nellie Smithers were an odd pair, but there was a clear logic to their mutual dynamic. Will supposed that the same could be said for Margaret's and his emotional interplay, but he felt that theirs was anchored in a deep love, while Connie's and Nellie's was rooted in what? . . . love perhaps, or an assertion of sheer power and acquiescence? It was hard to tell with first impressions, but Will was careful to withhold judgement until he got to know Margaret's friends better.

* * *

Margaret could hardly contain her excitement now that her old playmates were here. She was loyal to her Master Will, just as she had been to her husband, Master Paul, but she loved to be allowed special little treats now and then, when she could greedily indulge her utter sluttiness with almost no limits, just let herself go and work herself into a frenzy of debasement and dishevelment. She had spent so much of her life trying to keep her shameful cravings under her own control, or that of her Masters, that these special play-binges were like brief visits to Paradise, where all propriety and respectability went out the window.

Earlier, knowing that Connie and Nellie were soon to arrive, Margaret had treated herself to an especially striking ensemble for the day. She had put on seamed lavender stockings and fastened them to a matching garter belt. She then drew up lace-trimmed lavender knickers, watching herself in the tall mirror on the wall. Next came a matching lavender bra which nicely lifted her generous bust and created some tantalizing cleavage. Then a lavender half-girdle that tucked in her little belly and made her feel firmly controlled. This was followed by a sheer lavender slip, and the whole ensemble was topped off with a form-fitting deep purple button-up dress with large lavender decorative buttons in front. In a nod to practicality, the dress was sleeveless, allowing some ventilation to her otherwise firmly encased body. As a final elegant touch, she stepped into purple four-inch pumps. Oh, and let's not forget the long purple gloves that matched her dress and pumps. She turned and admired her reflection in her mirror. She wished to look her very best for her dear friends' arrival.

With her guests seated in her living room, Margaret served them and Will some nice tea and biscuits as a welcoming gesture. She noted Will looking slightly puzzled as he gave Connie's outfit a bit of a stare.

"Connie, why don't you relax and make yourself totally at home? I know you must feel yourself a bit confined by your travel gear. Feel free to have Nellie unwrap you, if you like. I'm positive that your unveiling will be a real thrill for Will." She addressed a loud whisper to Will, just loud enough for her guests to hear. "Connie's a bit of an exhibitionist, Sir, and she loves to display herself to appreciative eyes. I promise you are in for a real treat!"

She and Connie exchanged knowing smiles, as Connie and Nellie rose from their seats. As if in a well-practiced ritual, the diminutive man attended to his wife, standing behind her and carefully unbuttoning the back of her dress, starting at the nape of her neck and working his way down. That done, he quickly came around and lifted the dress off of her, in a dramatic flourish worthy of vintage burlesque.

Will was struck dumb, trying to process what he saw. Connie's whole trunk, from her armpits to her waist, was wrapped in layers of plastic wrap tightly containing what appeared to be two stupendously massive breasts reaching down past her belly button to just short of her hips. Will immediately sprung a boner at the awesome sight, letting out a low whistle.

Connie smiled coquettishly and lifted her arms and placed her hands behind her head, exposing her smoothly shaven armpits as if she were the goddess Venus on the Halfshell. Nellie began freeing his wife, methodically walking around her and unwrapping her layer by layer.

"I suppose you are wondering why I have this done to myself," Connie spoke to Will. He nodded, his gaze fixed upon the emerging sight. "I've found from hard experience that if I go out in public without minimizing my bust, I cause car crashes and more. Bras only accentuate the problem, and besides, it is nearly impossible to have custom brassieres sewn that are practical or comfortable for titties like mine.

"I suffer from a rare condition called Gigantomastia, where one's breasts just keep growing and growing, often as puberty hits. I apparently had some endocrine and estrogen imbalances which caused them to grow well after most girls begin to slow down. That condition also had another side-effect which I will display for you as soon as Neville finishes his present task."

Just as Connie said this, Nellie made his final circumnavigation and squatted by her feet and began to gather up the heap of plastic wrap.

"Nearly done, dear!" Nellie said brightly in a quiet loving voice. "Er, Miss Margaret, where would you like this to go? In the recycling?"

"No, no, just stick it in the trash bin in the kitchen. I don't think plastic wrap is allowed in the recycling."

Once Nellie finished that task, he came back in and spoke to his wife in a solicitous tone.

"Sweetheart, what can I do for you now?"

"Neville, my Little Man, would you be so kind as to pull my knickers down so that we can display my other anomaly to our gracious hosts? Please do so from behind, for better effect, and when you are done you are allowed to stick your nose between my buttocks as your reward for being so helpful."

Nellie blushed in humiliation, but he licked his lips in anticipation of this special favor. He quickly knelt behind his wife's big fleshy bottom and carefully gripped the elastic top of her sizable knickers on either side of her hips and slowly pulled her knickers down to her ankles and waited as she stepped out of them. He then donned the fragrant knickers like a hood, but with his nose and mouth sticking through one thigh-hole. With shaking hands, he gently pried Connie's soft globes apart so that he could insert his nose into her sweaty arse-crack as far as possible, positioning it up against her filthy unwiped sphincter and sniffing deeply.

"Neville, dearest, if you can still hear me, I'll even let you kiss and tongue my anus clean as well. As you are quite aware, I am extremely sensitive there and I think our hosts will enjoy the effect that your oral worship and cleansing of my shit-hole has upon me."

As rude licking and smacking sounds began to filter out from deep within her cheeks, Connie stood with her legs well apart and playfully announced "Voila!" Margaret knew what was coming, but Will did not and his eyes bulged out as he caught sight of the 'anomaly' unfurling itself out of its hood atop Connie's swollen and elongated labia. It was her freakish clitoris, which was growing before his eyes, until, in its excited state, it was nearly the size of his own stiffened cock tenting the front of his trousers. For the second time that afternoon he was rendered speechless.

"It's called 'Hypertrophy of the Clitoris' and sometimes accompanies Gigantomastia under certain conditions. I got hit with both, big time. It was not something I would have wished upon myself, but I've gotten used to both conditions, and they do have their advantages."

Connie continued to stand before her spellbound hosts grandly exhibiting and petting her outsized pink clit, though she backed up a small step in order to mash her rump even more firmly against her husband's face. His tongue was deep within her poop chute and he gave a little smothered cry as he reestablished his balance and continued his private worship service, causing Connie to emit a loud odiferous and rather wet fart.

"Neville dear, you are outdoing yourself today. I may even allow you to share the bed with me tonight, instead of sleeping in your dog bed on the floor. Would you like that?"

A muffled moan indicated his agreement. In the elated high of seeing her old friend Margaret and her friend's handsome new Master, Connie was feeling quite magnanimous and thoroughly horny. She was already scheming various scenarios she could lead her hosts through, allowing Will and her to assert divine mortifications upon Margaret and Nellie. She knew very well that during these special play visits, Margaret could be persuaded to do just about anything, no matter how filthy or painful.

Connie even had an intuition that she could enforce her will upon Will, so to speak, as he seemed truly in awe of her grotesquely enlarged body parts and she was well-practiced in using them as bizarre sex toys with which to dominate others. A little shiver of joy went through her body at the prospect and, as she fondled her clitoris, quickly expanded into an electrical surge through her nervous system. She gave a hoarse shout as an orgasm engulfed her, spraying her hosts with a mighty squirt of cunt juice.

The effect was contagious and Will felt himself helplessly exploding in his trousers, while Margaret just whimpered and gave off little ecstatic cries and sqeaks. Last but not least, Nellie was knocked backwards, off his knees and onto his back, by the impact of Connie's powerful cum. His little penis twitched and thrust in his pants as he too was overcome and soaked the pink girly knickers he was wearing under his pants. It was a delightful start to a very lewd visit.

chapter 2

After a certain interval of innervation, the two kinky couples recovered themselves and surveyed the erotic landscape. Each of them had cum in their own lewd manner, either squirting, ejaculating, or giving in to serial orgasms. That set the baseline for their debased playful encounter. There would be nothing too perverse or depraved to enjoy. At the same time, they wanted to ease into their obscene play, as none of them could be sure where personal taboos might erupt, or lines might be crossed.

Will's and Margaret's clothes had been soaked by Connie's squirted love juice when she had her titanic orgasm, and also by their own eruptions. Likewise, Nellie had spontaneously cum in his girly knickers creating a real mess as well. The two hosts proceeded to strip down, though in Margaret's case, this took considerable time as she had so many layers of coordinated lavender undergarments to remove. All eyes were on her as she removed her lovely ensemble piece by piece. They gave her a nice little round of applause when she finally stood before them displaying all her natural charms. She gave them her little smile, while blushing deeply. There was no question that she was a very charming sub.

Nellie had held back from disrobing, as he needed to get Connie's approval for such actions and Connie's eyes had been glued to Margaret's little strip routine. Now her gaze shifted to her husband's disheveled state. He knelt on the floor, with her knickers encasing his head like a hood, and the crotch of his pants clearly soaked with his own cum.

"Neville, what is this? I don't recall giving you permission to ejaculate!"

"No, dear, you didn't. I j-just couldn't help myself", he said contritely, his eyes locked in fear at her outraged expression.

"Hmph, as you well know, that is no excuse! And here we were doing so well, and now you've gone and spoiled it! This calls for immediate punishment. Please undress and hand me your polluted knickers this instant!"

She turned to her hosts and apologized for this unforeseen interruption to their proceedings.

"But perhaps we can turn it into a little love tryst as Neville gets his due. I believe if we position ourselves correctly together, we can all derive some pleasure from my husband's violation. Will, would you mind if I have Margaret attend to my quim while I am sodomizing Neville with my clit?"

Will had seen something like this coming and he figured such shenanigans were inevitable. Not that he particularly minded. He knew that Margaret had a long history of intimate play with Connie and Nellie, and he was curious to see what depravity they might all get up to.

Margaret was looking at her Master with her hands clasped, as if in prayer, and a look of extreme longing in her eyes. "Please, Sir. It's all part of our fun! I'll bet she has a treat or two for you as well!"