Peggy

Add To Cart

EXTRACT FOR
Peggy's Dilemma

(Imelda Stark)


PEGGY'S DILEMMA:

CHAPTER ONE

 

Margaret Sanderson had a problem. In fact, it was a very big problem that had haunted her for many years, ever since she was a quite confused teenager. And now that she was thirty and had been promoted to Vice-Provost at Holy Redeemer College for Young Ladies, this particular difficulty seemed to be only getting more complicated. That maddening complexity was fast approaching the boiling point where she was afraid she would have no choice but to act on her powerful, confusing feelings. And if she did so, the lovely raven-haired woman feared that there would literally be Hell to pay.

For this is exactly what our Peggy (the nickname Margaret had been called by since girlhood) believed. She had been brought up in the apostolic Protestant faith since earliest memory, and for her there was a God and a Savior and a genuine Satan waiting to catch unwary sinners in his clever nets. Many of the things that had happened to her over her life had been confusing, especially the sexual things. So she had always prayed and listened to her pastors and done her best to be good, but sometimes especially the last part was terribly hard. And recently, for a variety of complicated and bewildering reasons, being good was getting even harder.

One of those reasons for Peggy's growing confusion was her boss, Provost Edwards. He had been in that role for her since her promotion two years earlier from her original job as the physics instructor at the college. Now she still taught the physics classes, but in addition she worked administratively for half her day under the careful (and way too sexy) blue eyes of Jason Edwards. The fact that he was a bona fide six-foot two-inch hunk of muscular manhood certainly didn't make her life any simpler. But her romantic feelings towards her dreamy (and damnably single) boss were complicated even further by one of her roles as his assistant.

The particular task that was further bedeviling (so to say) our heroine was her role as chaperone for the corporal punishments that were the strict policy of the school. As a biblically inspired institution, HR (as it was called by the faculty) took quite literally the Old Testament injunction that to spare the rod was to spoil the child. And especially with several hundred energetic college girls whose hormones were causing them to chafe against the restrictions of a strict moral and behavioral code, several spankings each day seemed to be required to maintain proper order.

The role of disciplinarian in such matters at the school was reserved to the Provost. Of course, since he was the only male at the establishment (the classroom teachers all being female), a chaperone was necessary in order to ensure that nothing untoward took place during spankings. And this duty always fell to the Assistant Provost. A miscreant student would be sent to the office with a note from her teacher explaining the nature of the infraction. The school secretary would pull the girl's file and remove her disciplinary record so Mr. Edwards would have convenient access to the punishment history of the culprit. Then Peggy would be summoned to take the record into the Provost's office. Meanwhile the distraught student awaited her fate under the watchful (perhaps a bit gloating?) eye of the secretary.

Peggy and Jason would then discuss the appropriate consequence for the infraction in question. For first offences or minor infractions such as whispering in class or passing innocent notes, perhaps a hand spanking over the uniform white-cotton bikini panties would be in order. The minimum number of spanks was twenty-five per bottom cheek, and this dose seemed to suffice for the uninitiated. This escalated with repeat offenses until a ceiling of a hundred swings of his powerful right arm per moon was reached, after which more severe penalties ensued. Mr. Edwards liked delivering hand spankings, in that they were the only time he actually got to feel some of the very appealing firm young buttocks he was charged with punishing.

Of course, as Peggy soon realized, Jason Edwards rather enjoyed administering any kind of spankings. She could hardly mistake the rather large and intriguing telltale bulge he would get in a certain critical area of his pleated khaki's during the course of chastising some of the more attractive bottoms among the student body. Many of the teachers wondered about this, though their always-thoughtful leader never behaved with a single bit of impropriety in any setting. In fact, before Peggy was promoted, she and some of the younger single instructors used to giggle that they wished they could volunteer for a spanking, just to get closer to their dreamy and apparently imperturbable boss. Our Peggy suspected that she was the only one of them who meant that fantasy quite literally, for reasons that will become apparent as her story unfolds.

But we digress. Let's return to the ritual pre-spanking discussion of the penalty to be suffered by the misbehaving female rear end in question. In most instances, Peggy and Jason were dealing with a multiple repeat offender or with crimes exceeding the lowest rung of the disciplinary ladder. This would then involve the lowering of panties until they resided around the knees of the now-blushing offender. Who was no doubt totally mortified to have her naked bottom revealed to the two Provosts. More severe infractions required the direct administration of consequences to the unprotected buttock skin of the culprit. And her embarrassment was considered an important additional punishment.

Of course, contact between Mr. Edwards' hand and the naked rear ends of his charges was out of the question. So the next consideration he and Peggy would have to make once a bare-bottom spanking was prescribed was the implement to be used for its delivery. The least severe of the options was a brown leather paddle whose oval business end (roughly the size of Jason's large and surprisingly hard palm) was placed on the end of a six-inch handle. One step above this was the very same instrument with approximately a hundred holes drilled through it to enable trapped air to escape so it could make a more telling impact on its squirming target. The students called this paddle 'The Whistler' because of the sound the air made passing through its many holes as it was swung, and it was universally loathed by its customers.

As with hand spankings, the dose of each implement began at twenty-five spanks per youthful buttock. As warranted it would be raised in increments of the same number until the threshold of a hundred was reached. After that point, an unwelcome (to its recipient) graduation to the next most severe weapon was in order. This would be the wooden paddle, a fearsome instrument constructed of light ash wood in the shape of a small hand mirror. It connected with its targets with a terrifyingly loud crack and an even more horrifying sting. Only the very most rebellious and naughty of girls ever required as much as a full dose of a hundred per cheek of the wooden paddle. It was dubbed 'The Stinger' in fearfully whispered student lore.

So first a decision was made between the two administrators about the state, either clothed or naked, of the buttocks to be punished, and the implement and dose to be administered. Then the often-weeping miscreant was fetched from the outer office by Peggy. Who by this point usually found herself somewhat flushed with her own rather shameful excitement. This was on several counts. The first of which was her terrible crush on the Provost, whom she found rather infinitely desirable. So any tĂȘte-Ă -tĂȘte with him was likely to bring a blush to her lovely cheeks, as well as a certain telltale moisture between her legs. The second reason for her high coloration would be her secret eroticization of spanking. This had its origins, as for most submissives, in her early life, about which we will learn a great deal more later. And finally, and most shamefully of all, our Peggy was excited because of her biggest secret of all: her hidden bisexuality.

Now you must understand that for a dedicated evangelical Christian woman, the fact of a powerful sexual attraction to other females was a living nightmare. There was no place in the far-right wing of the church for tolerance of such feelings. So the fact of her undeniable sexual response to seeing an attractive female bottom bent over the Provost's desk, let alone being the one to raise and pin up its uniform pleated plaid skirt, and further to even lower the white cotton bikini panties to reveal the all-too-often totally succulent naked backside was the source of infinite quandary for our Peggy. She had made valiant efforts to overcome this reality of her erotic wiring, as we will see below, but so far with only limited success.

But whatever the source of the Vice-Provost's arousal, the ever-observant Provost was only too aware of it. In fact, wondering about this and about the possibilities it might open up for him with his lovely assistant was never far from Jason Edwards' rather naughty mind. He often laughed inwardly about what his whole strait-laced community would do if they knew what he was truly like under his carefully cultivated disguise of impeccable rectitude. But the former Marine's iron self-control meant that he had never once stepped out of line at HR to gratify his secret penchant for sadomasochistic sex. He did his job, attended church and taught Sunday school, and courted pretty single women until he discovered whether they had any resonance to his darker side. Once he found they did not, he would deftly withdraw and move on to the next candidate, of which there was never a shortage for the stunningly handsome man.

In the meantime, Jason would happily take the gratification that delivering several spankings a day to quivering young female buttocks afforded him. In fact, he had set up a secret camera in a cabinet behind and just to the side of the position in front of his desk where the recipients of his disciplinary efforts were bent over. Later each night he would masturbate to powerful climaxes while watching some of his favorite backsides take their medicine. But his greatest secret longing was a real live wife with whom he could show his full nature and find a willing recipient of the painful attention he so enjoyed dishing out to deserving feminine rear ends.

So the dominant man always kept a part of his awareness on his succulent assistant during their shared secret pleasure of spanking a student. As time went on, it seemed more and more possible that she could be the one he was hoping for, but he was reluctant to make the first move. After all, if he was wrong, he had a very great deal to lose. Their community would reject him faster than an AIDS infected condom if there was ever any whiff of scandal involving their Provost and any of the females under his command. So any approach he made to his smoldering assistant was going to have to be clearly initiated by her, not him.

 


CHAPTER TWO

 

In the meantime, the couple gingerly explored their shared perverse erotic universe indirectly, through the medium of collaboration in the spanking of the impudent buttocks of misbehaving students. And these ritualized punishments went something like this. Peggy escorted their frightened and often weeping subject into the Provost's office, ostentatiously locking behind her the door into the outer office where the culprit had been waiting. This sent the chilling message that the proceedings were not going to be disturbed by any outside agency.

Both of the administrators could sense each student's heart sinking as the dead bolt clicked into place and her bottom's impending painful fate was sealed. Then the miscreant was made to stand in front of Jason's antique oak desk, facing her inquisitors. A discussion of the sin being atoned for would take place, including the student's history of previous punishments so that the current prescription would be understood in context.

In the example we will be describing, Mary Jane was a lovely blue-eyed senior girl who had been caught smoking behind the gym. This was a very serious infraction, in that it not only broke rules but seriously endangered her health. This was the tall, voluptuous blonde's second offense for the same crime, and took place in culminating a series of rebellious acts stretching back to her freshman year. So all present were aware that the outer limits of the severity of spanking were to be tested that afternoon, since her last offense had warranted a hundred spanks from the Stinger on each bared buttock.

Mary Jane was the most frequent customer for Jason and Peggy's disciplinary services. And secretly, the curvy senior was an erotic favorite for the two administrators. She was the daughter of their local pastor and had been in covert rebellion against the constraints of their religion and her position as a supposed role model since girlhood. At least once each month since her arrival at the small private college over three years earlier, Mary Jane had been bent over the desk for her comeuppance in a long and painful conversation between some implement and her behind. Spankings through panties were a relic of the distant past, and her bare bottom had been the sole target since the fourth month of her freshman year. She was the only girl who received the Stinger each time, an honor earned by her uncontested title as the most recalcitrant young woman at the school.

And even if it had been weeks since her last spanking, once her panties were lowered the beautiful student's bottom always bore the aftereffects of punishment she must have received at home. Clearly, the pastor practiced what he preached when it came to corporally punishing miscreant offspring. Mary Jane never cried or whined before her spankings, always displaying a certain subtle brazenness on her lovely features as she awaited her fate and was escorted into the Provost's office. This discreet lack of contrition actually added to the pleasure that Jason and Wendy took in their task. There was not even any vain attempt to evoke their pity as was the case in most of their subjects.

This time, it seemed that new heights were going to need to be ascended in the severity of her punishment. The pre-spanking discussion had taken unusually long because of this, and as the inwardly trembling miscreant stood before the solemn administrators, she knew this did not bode well for her poor buttocks. Sitting comfortably was likely to be out of the question for most of the next week, especially if her parents caught wind of this latest offense. If they did, she could count on a long trip over her Mother's hard lap as soon as she got home for an excruciating conversation with the backside of her walnut hairbrush. And then once her Father returned and her crimes were discussed at length over dinner, she could expect to be bent over the table after she had cleared it. Her mother would lower her panties and his wooden paddle would be used to administer a third dose, just to drive the point home. Of course, the intelligent senior knew that each of these extra helpings of buttock pain were actually being administered so that each of her parents could assuage their embarrassment that their only child was so publicly rebellious.

What none of them seemed to realize is that simple stubbornness was only a part of why such a bright young woman seemed to be in trouble so routinely. The real reason was much more complex. Actually, since several years earlier, Mary Jane had begun to experience strange and exciting sensations between her legs during her spankings. She investigated those unmentionable structures 'down there' as she lay sobbing on her belly on her bed, and discovered a fascinating and quite pleasurable sensation when she touched certain parts of her genitalia. And then she was amazed to find that she could continue to massage the little button at the top of her slit in just the right way and feel even better. Then if she persisted, an incredible explosion of pleasure caused her whole body to shake and writhe for many seconds before she would slump in blissful relaxation and fall off to sleep.

So provoking a spanking became a way for the repressed and rebellious girl to subtly co-opt her jailers into giving her the greatest pleasure in her otherwise celibate life. In fact, Mary Jane didn't even like cigarettes, but the spanking she received for this offense was by far the hardest she had ever gotten. And in turn, as she had learned from long experience, the greater the pain her poor bottom cheeks had to endure, the more amazing the pleasure she got when she masturbated afterward. The blonde beauty matter-of-factly decided that this was a trade she was more than willing to make as long as those in charge of her insisted on doing their part.

While her parents had no experience spanking anyone other than their maddeningly wayward daughter, this was far from true for Jason and Peggy. And they both knew that Mary Jane was different from any other girl they spanked, both in her attitude about being punished and in her responses. Almost no other student maintained the subtly challenging air that the blonde senior displayed before each punishment. And certainly no other miscreant showed the telltale signs in the crotch of her panties that even the apparent prospect of being spanked was incontrovertibly sexually arousing.

This apparent truth was borne out by observing the writhing senior's bared pussy once her spankings had begun. She would, as all spanked students, initially try to hold her legs tight together in order not to display her private parts to the carefully attentive administrators. But as was the case for every student they spanked, once the painful collision between an implement and their bottom flesh hijacked their awareness totally to that intersection, all thoughts of modesty fled consciousness. And the fruitlessly wriggling and plunging youthful buttocks clearly showed everything between them. In Mary Jane's case, this included the undeniable fact that as each spanking progressed, her sparsely blonde-furred pussy became steadily more moist with the exudate of her arousal.

Of course, this mutual observation was never discussed between the Provost and his smitten assistant. But each was aware that the other's eyes tended to wander toward this evidence that one of their regular disciplinary customers shared their eroticization of spanking. On the occasion in question, both had agreed that an unprecedented level of consequence was called for. Mr. Edwards communicated this unwelcome news in a stern but calm voice: 'Mary Jane, it seems that a hundred spanks with the wooden paddle to each of your bottom cheeks was insufficient to negatively reinforce your smoking behavior. Since any more swats with such a fierce instrument would risk causing damage to your body, we have decided to give you a warm-up hand spanking of a hundred per buttock through your panties before Mrs. Sanderson lowers them so you can receive your paddling on the bare. You may bend over the desk and assume the position.'

The tall blonde sighed as she complied, her stance and locale all too familiar after dozens of repetitions since she was a freshman. The fact that she had just turned twenty-one and yet was still being spanked like a little girl at least every week didn't seem at all discordant to her. She gripped the far edge of the desk, knowing that once her skirt was raised and pinned up, the Vice-Provost would come around and hold her wrists. She had never tried to reach back to protect her rear end from its well-deserved fate, but Ms. Sanderson still did this for every spanking. The blonde student had never actually stopped to wonder why.

The truth was, that because of the full-length mirror covering the back of the door leading into Jason's office, Peggy got the best possible view from this perspective of every nuance of reaction of each punished rear end. Even the Provost's hidden cameras, each perched in a cabinet beside the door to give him a stereo view, didn't afford such an ideal perspective. So once the bent student felt the older woman's cool hands raising her skirt and pinning it up to her white linen uniform blouse, the next thing she felt was the same firm touch on her wrists, pinning her arms in place for the duration of her first dose of painful medicine.

Mary Jane's perverse little heart had actually soared at the news of her additional warm-up spanking. She had been a dewy-eyed freshman since the last time her penance had been delivered by the Provost's hard hand to her pantied bottom cheeks. And, like what seemed to be every other heterosexual girl at the school, she harbored a secret crush on the handsome former Marine. The thought of his hand actually touching her buttocks, even through her panties, was as arousing to her as the sure knowledge that he would be seeing every bit of her naked rear end as she writhed and bucked her way through her eventual paddling.

As usual, he stepped to her left and steadied himself by placing a casual hand firmly on the small of her back. Then without further ado Jason delivered a brisk hand spanking to the delightfully voluptuous nether moons that strained tauntingly through their thin cotton containment. They were quite firm under their half-inch layer of feminizing fat, since the girls at HR were required to do an hour of hard exercise five days a week without fail. Indeed, the buttocks he was spanking with such relish seemed every bit as womanly as the ones the Provost often fantasized about in a similar situation as he caught his surreptitious glances at Peggy's rather charming backside.

And the twin moons danced quite fetchingly as his large, hard hand worked its way around them in his usual systematic manner. Their owner reacted in her usual way to her spanking: an immediate flow of tears down her lovely face always turned towards the side on which her punisher stood, and a single sonorous 'Aaah!' with each fearsome collision with her vulnerable nether cheeks. The Vice Provost kept her eyes glued to the image in the mirror, fascinated to watch the wet spot in the center of the crotch of the gyrating panties grow steadily in size as the spanking progressed. And as was her task, she called out a count of each blow until the final total of two hundred was reached and the room was silent save for the sniffles of the punished girl.

The Provost spoke: 'Very Well, Vice Provost Sanderson, you may take down her panties for her paddling.' The totally aroused older woman complied, walking around the left side of the desk to accomplish this task. She noted that the fascinating bulge in Jason's khakis was even more prominent than usual, suggesting that her ardor was shared by her boss. She didn't even dare to imagine that a substantial amount of his excitement was in response to her rather than the gorgeous young beauty they were punishing in such a sexy manner.

The Vice Provost always took the opportunity when she was skinning down a girl's panties to cop a feel of her bottom cheeks. Her boss was well aware of this and regarded it with a combination of amusement and curiosity. He suspected his assistant had a crush on him but found intriguing the possibility that she was aroused by females as well. If that were true, some very interesting possibilities could open up in the future he had been allowing himself to fantasize for them.

In any case, Peggy's method for removing a miscreant's panties was to reach up underneath them along the sides with her palms down, and then to turn her hands over and pull them down with the backs of her hands against the bent buttocks. In this case, the skin she came in contact with was quite hot and inflamed by the vigorous hand spanking just completed. Mary Jane moaned in relief at the delicious cool sensation of the Vice-Provost's hands against her throbbing nether cheeks. And conversely, the older woman was fascinated by the degree of heat that had been produced. She wondered what it might feel like to receive the very same treatment from her boss, and almost swooned at the rush of arousal that flooded her own crotch just as copiously as that of the garment she had just lowered to restrain the girlish knees of their subject.

Jason allowed just a touch of amused irony into his gaze as his eyes met Peggy's after her task was done and she had resumed her post holding Mary Jane's wrists. The assistant blushed even more fiercely at their shared awareness that she had been caught out more blatantly than ever before but lowered her emerald-green eyes in a silent admission of her guilt. What this would mean or lead to she had no idea, but she had an exciting and terrifying sense in the pit of her stomach that something was about to change, and soon.

In the meantime, the main thing that was changing was the state of their miscreant subject's buttocks. The vigorous hand-spanking they had just received was a love tap compared to the paddling they had coming. The Stinger smacked against them with its frightening loud crack and its even more horrifying agony. Of course, Mary Jane's tears resumed immediately, but this time her verbalizations changed in timbre from the sweet soprano cries of 'Aaah!' to hoarser, full throated shouts of uncontrolled anguish. And her bottom cheeks' charming dance through their encasing cotton also transmuted to much more vigorous (and even more delightful to her sadistic audience) clenches and bucks as her poor backside struggled to accommodate its unprecedented plight.

When Peggy had lowered Mary Jane's panties, she had noted that the student's pussy was already glistening with the liquid evidence of its arousal. Well, as the paddling progressed, so did this condition. The Vice-Provost watched spellbound as the punished girl's lightly-blonde furred crotch actually became so moist that a drop of its liquor fell to the office floor just as the spanking was coming to its climax. Both Jason and his raven-haired assistant found themselves slightly panting in sympathy with the incontrovertible arousal of their miscreant naughty girl. They all recovered in the sudden post-spanking silence after the two-hundredth blow of the second dose had been counted out by the assistant.

Spanked students at Holy Redeemer were always required to do half an hour of corner time with their blazing buttocks displayed to the Provost and his minion as they got on with administrative chores. This allowed the subjects of their disciplinary attentions time to get themselves collected to rejoin the student body. And for the two secret connoisseurs of spanked female teenage rear ends, it also enabled a good long chance to enjoy the fruits of their labors as the inflamed cheeks continued to twitch in remembrance of their ordeal. At last, Peggy raised Mary Jane's panties, their owner hissing at the pain as the garment slid over her lightly bruised and very swollen nether cheeks. Jason watched as his aide assisted the senior out his door, noting a slightly increased wiggle in the older woman's delectable backside as he fantasized about subjecting it to the very same attentions he had just administered. And its owner was imagining the very same thing, each parallel line of longing unbeknownst to them both.