TAILS
FROM THE CRYPT
The Gypsy
by
Hawkwood
Louise was reasonably certain that she could achieve a similar fortune in a similar manner. She was perfectly willing to concede that Anna was the better looking, but that was like saying a Ferrari is prettier than a Land Rover: it depends on what you want to do with it. Anna was, by general admission, the most spectacularly beautiful woman in the company steno pool, with incredibly long legs, tumbling blonde curls and a slender model's figure than turned heads everywhere she went.
By contrast, Louise was shorter, darker and more, well, solidly built. No one would ever mistake her for a model, except maybe for some of those in the porno magazines. Her 38 C cup breasts seemed even larger on her shorter frame, and a matching dimension around the hips made her seem a little, well, matronly in street clothes. In a swim suit, however, she had been the cause of more than one sudden and painful erection in male observers. And none of the men privileged to share her bed had ever complained about her technique or enthusiasm.
There was, she discovered, no convincing Anna that the gypsy woman was a 14 carat fraud. Finally succumbing to her friend's insistence, Louise had gone with her to have the gypsy read her fortune. The old woman had frowned over Louise's palm for several minutes, and seemed to shake herself. In a halting voice, she told the skeptical brunette that her future was at a crossroads. She mus make some difficult choices in the months ahead, and the wrong ones could have dire consequences.
For example, she said, Louise should not, at any cost, go to her own flat tonight. She should find a hotel room, or stay with a friend, ANYTHING but spend the night in her own bed. Amused, Louise had asked if she should let some man take her home? The gypsy didn't see any humor in the suggestion, instead, she nodded her approval of the suggestion. That would be an excellent choice, she said, but not really necessary. The only thing that mattered was that she not go home.
Louise didn't believe a word of this bullshit, but she couldn't help being impressed by the woman's obvious fear. If she was playacting, she was doing a very good job. Anna, of course, was terrified and insisted that her friend spend the night with her. Rather than argue with Anna, Louise agreed to spend the night.
It seemed kind of spooky as the two women spent the evening pretending to be happy. Neither slept very well. And in the morning when they opened the paper, their mood was not improved. A gas explosion and fire had gutted an apartment complex, killing three people and hospitalizing a dozen more. Both women recognized the address of the complex immediately. They should have; one of them lived there.
Anna, of course, saw this as proof positive of the gypsy's skill. Louise was still skeptical, consider it more probably an amazing coincidence, but she was less sure than she had been. In either case, after they had taken the morning off to shop for Louise some new clothes (since hers had been destroyed in the fire) Anna had little difficulty convincing her friend to return to the gypsy on their lunch hour for more word about her future.
This time, the gypsy seemed almost puzzled as she laid out her tarot cards. Frowning, she told Louise that one of her choices must be between two men in her future. She was destined to marry one of them, but which one, the gypsy couldn't say. One of the men would offer her a life of sexual ecstasy and love, but the other would offer only pain. The gypsy's puzzlement was in deciding which was which. There seemed to be contradictory information in Louise's horoscope. It was not a matter of immediate concern, but Louise was cautioned to be very careful in her relationships.
THAT, at least, Louise found to be good advice. She'd had a couple of unfortunate affairs that had come to bad ends, and she ALWAYS tried to be careful.
For Anna, the gypsy found a simpler but similarly troubling forecast. Louise had never seen the tarot card of the bared buttocks before, but there it was, next to Anna's. It meant, the gypsy said, that she was about to have her bare bottom whipped, rather severely. There was nothing, the gypsy asserted, that Anna could do about this that would not make it worse in the long run. Accordingly, when she was presented with this threat, she should submit to it without argument.
Louise was horrified. The very idea that Anna should let someone whip her was offensive! Her lingering doubts about the gypsy were reinforced by this idiotic pronouncement. She told Anna on the way back to the office not to pay any attention to the ranting woman, but Anna wouldn't listen. The gypsy had been right about Louise's apartment, hadn't she? Anna was not about to ignore the woman's advice.
Louise did not see her friend again until after work, but when they boarded the bus to go home (Anna had invited Louise to stay with her until she could find a new flat of her own), she saw the suppressed tears in Anna's eyes, and the way she fidgeted on the hard seat and knew another prediction had proven true. Once back to Anna's flat, she had insisted on seeing the damage. Anna had tugged up her skirt to expose buttocks thoroughly bruised and nearly, but not quite, blistered by a vigorous paddling.
Louise dug out the details. The new vice-president, Mr. Endicott, had called Anna into his office about two. He'd pointed out to her a surprising number of spelling and grammatical errors in her work (Louise had to admit that Anna was not the world's most careful stenographer) and told her that perhaps she should seek another position.
Startled, Louise asked if her friend had been fired? Anna shook her head and said that had been Mr. Endicott's intention, but she had begged him for another chance. She had asked if there wasn't some other punishment for her mistakes that would let her keep her job?
Louise's eyes went wide, and Anna confessed that that had been Mr. Endicott's reaction as well. He had asked just what she had in mind, and Anna, spotting a heavy eighteen inch wooden ruler on his desk, had pointed to it and offered to be spanked good and hard on h er bare ass.
Horrified, Louise confirmed that her friend had VOLUNTEERED to be whipped!
Well, why not? Anna had asked. The gypsy had already told her she was going to get her ass whipped. At least this way she had saved her job! Mr. Endicott had been very nice about it, actually. He had warned her that she shouldn't do this if she didn't mean it, because he'd have to make it a real paddling if it was going to do any good. Anna had confirmed her intention to submit and had bent across his desk with her skirt over her back (and of course, she never wore panties, claiming that they ruined the lines of her skirt).
Mr. Endicott had obviously had no trouble deciding to take her at her word. He had smacked the ruler across the bared buttocks for what had seemed an hour at least! It had been, Anna admitted, a very long and painful spanking, but certainly no more than she deserved. And no more than she had expected, given the gypsy's prediction.
Louise was astounded that ANYONE could be so gullible. The idea that Anna should ASK her boss for a spanking, just because some damn gypsy fraud had said so, was appalling! Of course, she had to admit that her friend had been in something of a bind. Even a spanking was better than being fired, and it sounded like Anna had been in real danger of losing her job. Eventually she shrugged, deciding not to worry about things she couldn't do anything about anyway.
That night, Louise dreamed about two men.
And of course, Anna insisted they return to the gypsy the next day.
The gypsy was unimpressed with Anna's revelation about the accuracy of her prediction. Having established the pattern, the old woman said, Anna should expect to have her rump warmed regularly in the future. Shit! thought Louise. SHE could have predicted THAT! Mr. Endicott would probably be HUNTING for mistakes in Anna's work so he could get her across his desk again.
Then the gypsy turned to Louise, frowning. One of the men was near, she said, but she couldn't find out which one. She cautioned Louise that all was not as it seemed, which seemed to the skeptical brunette like one of those prophecies that couldn't be wrong.
That afternoon, Louise had met Mr. Endicott.
She had been called to his office, and considering her friend's experience, had been more than a little worried. Mr. Endicott turned out to be a rather nice looking man, middle aged but in very good shape. He seemed not to know how to smile, and had talked about the need for a "disciplined" work force, which she thought she understood just fine. She admitted to feeling a bit prejudiced against him after Anna's story, but she softened up when he began to compliment her on her work. She was, he told her, obviously a valuable employee, and he offered her a promotion on the spot: to be his personal secretary.
That frightened her. On the one hand, she could certainly use the extra money, especially with all her belongings destroyed in the fire, but on the other, she had no intention of becoming one of his "disciplined" employees. Then too, she knew that the company frowned on turning down a promotion. Anyone who did so was unlikely to get another offer. Eventually, trembling a little, she had accepted.
In her third day on the new job, she had been ordered to send for Anna. The blonde had looked frightened as she went into Mr. Endicott's office, and evidently with good reason. Even with the door closed, Louise could hear the sounds of a prolonged application of the ruler, and knew that the gypsy had been right once more. Anna had emerged bravely trying to control her tears, and Louise had gotten very angry at her new boss.
Then it had been her turn to be frightened as she was called into his office.
Mr. Endicott had shown her several letters and documents with the most incredibly bad English. Louise knew immediately that these were the cause for Anna's spanking. He had told her that he knew she must have heard what happened and wanted her to understand. Anna's work was totally unsatisfactory, he said, but it had been the girl's own suggestion that she pay for her mistakes in the fashion Louise had overheard. As he didn't want to fire her, but couldn't let her continue to do work of this calibre, he had accepted her offer. Until the blonde grew more careful with her spelling and grammar, she would be across his desk rather often.
Louise realized that Mr. Endicott was really doing Anna a favor! Certainly SHE would have expected to be fired if she had done work like the papers he had showed her. It made her a little less worried about her own future.
That was a mistake, the gypsy told her the next day. Louise was going to have to make one of the predicted decisions of her own in the near future, she was warned. She would have to choose among poverty, submission and pain. Moreover, the second man would appear soon. Startled, Louise realized that Mr. Endicott must be one of the two men she was supposed to watch out for! She couldn't imagine him as a lover, but he didn't seem dangerous either. She went back to work feeling very confused.
It had been the following Monday when Louise had been called into her boss' office to discover him frowning very unhappily at a contract. He showed it to her and she knew it was one she had typed for him. She looked to see what she had done wrong, but couldn't find anything. Then it dawned on her. The price was wrong! Too low by several thousand dollars, and the other party had already signed it (gleefully, she was sure). She stammered out an apology, but of course, there was no excuse for such a mistake. She couldn't imagine what had been on her mind when she'd typed the contract.
Mr. Endicott allowed that perhaps he had made a mistake in promoting her. perhaps she wasn't yet ready for work at this level of importance. He certainly couldn't permit mistakes like this to continue. Anna's grammatical errors, he said, had been nuisances compared to the loss the company was going to take on this contract.
And Louise suddenly saw where the conversation was leading.
The gypsy had warned her about a "painful" choice! And now she was looking at a demotion, for cause, unless she wanted to opt for Anna's solution. Mr. Endicott, she decided, was a damn clever man! He hadn't made any statement that could be construed as harassment; he hadn't offered to whip her. He had just VERY subtly made her aware of an alternative to her demotion if she wanted to choose it.
She knew very well that if she went back to the steno pool, she'd never get out of it. Not here, not anywhere. This would stay on her record even if she changed jobs! The idea of volunteering to be whipped nearly made her gag, but the alternative was really terrible. Trembling, her voice unsteady, she asked if she could be punished like Anna.
Well, not quite.
Mr. Endicott had been very sorry, but while a paddling might be sufficient for Anna's carelessness, it was plainly not an adequate penalty for the sort of mistake she had made. Louise felt her heart sink as she asked what sort of punishment WOULD be adequate?
Her boss seemed hesitant, unsure whether he should proceed with this, but Louise assured him
she would do whatever he thought necessary. Clearing his throat, he said that perhaps a sound
strapping, three dozen repeated every Monday for a month, would serve as a reminder she would
be unlikely to forget.
She couldn't even answer for a couple of minutes. Her brain simply could not assimilate the prospect of having her boss thrash her with a strap, and not just once! Every Monday for a MONTH! Oddly, it occurred to her that the gypsy was batting 1.000. She hadn't missed a trick yet! Still, without a viable option, she had silently nodded her agreement.
Then Mr. Endicott had cleared his throat as if somewhat embarrassed himself. There might be, he said, another option. Surprised, Louise had looked up to see him resolutely starring into space, avoiding her eyes. She had asked what he meant?
He would, if she wished, rescind all of the strappings but one. In return, he would expect to make
a simple spanking a daily part of their work routine for the next month. He would expect her to
present herself first thing every morning to receive a dozen from his hand on each cheek of her
behind, bare of course.
Well of course! she thought. What was it the gypsy had said? A choice among poverty, submission and pain! Poverty was obvious if she accepted the demotion. Pain apparently meant the weekly strapping. And submission meant letting him spank her bare bottom every day for a month. One HELL of a choice! She asked what he meant by all the strappings BUT ONE?
Still seemingly embarrassed, he admitted that he found his new secretary rather beautiful. He was, he said, indulging his own libido at the expense of any real punishment. However, in view of the seriousness of her error, he could not adjure punishment altogether. He could not justify any result that did not include her bottom receiving at least ONE sound thrashing. He would, if she liked, postpone that reckoning until the end of the month, but on that last day, she would certainly have her three dozen, and well laid on.
Louise trembled at the sentence. There seemed to be nothing she could do to avoid accepting a
grotesque and humiliating penalty for her failure. Briefly, she pondered his first choice, but she
knew she could never volunteer to face the strap any more often than she had to. She felt herself
flush at the thought of the daily spanking, but she knew she was going to agree to it. He
obviously expected that result, Hell! he had sculptured the choices so that she would have to
agree! Taking a deep breath, she asked when he wished to begin her penance?
Immediately, of course.
Seating himself on his office sofa, he invited her to lift her skirts and lie across his knees. It was, she realized, a position of time-honored submission, and all the more humiliating for that reason. Sighing, she had tugged her skirt and slip up to her waist and lowered herself across his waiting lap. If there had been any doubt that he was telling the truth about indulging his libido, it would have been resolved by the feel of his very erect cock against her side. She wasn't quite sure whether to be insulted or complimented by his obvious arousal. And when his fingers had grasped the waistband of her panties and tugged them down her hips and thighs to her knees, she had moaned with embarrassment.
With his left hand around her waist, his right caressed her now naked buttocks. She was about to complain about the familiarity when he lifted the hand and swatted her, quite hard, on the left side. In the sudden stinging of that impact, she didn't notice that his hand remained in contact with her flesh for several moments. Raising his hand again, he laid a similar palm print on her other buttock.
Louise was unpleasantly surprised by the burning pain he managed to impart so quickly. Two dozen promised to be more than a little disagreeable.
By the sixth swat, Louise no longer noticed or cared where his hand rested between impacts. Her ass was, she was sure, already badly bruised. It certainly felt as if she had sat on a hot stove. Mr. Endicott, for all his protestations, was obviously VERY experienced in spanking a female rump.
After the first dozen, she realized that she was squirming and almost certainly displaying herself shamelessly as the swats added to the fire in her buttocks. She tried to be stoic, to hold herself still, but her body would not obey. At the very next swat of his hand, she had wriggled, her legs spreading widely and sobbed helplessly with the pain. She didn't even notice that his fingers strayed into the exposed area as he paused.
By eighteen, her squirming had taken on an entirely new aspect. When she felt his hand lift, she dug her toes into the rug, raising her rump to meet the next swat. The pain was certainly no less intense, but it seemed different somehow. Panting now, she did not notice that her nipples were rigidly erect, or that his hand, between swats, was exploring with ever greater enthusiasm between her thighs.
When he stopped, and pronounced her first installment paid, it was all she could do not to beg him to continue. Frustrated, and now feeling the full burning result of the spanking, Louise had cried openly as she tugged her garments back into place. Mr. Endicott made no effort to seduce her, although he must have known that it would have been terribly easy. Instead, he dismissed her, saying he would see her again the following morning.
She had spent a very uncomfortable night, alternating between feelings of self-pity for her tender rump, and frustration for unsatisfied arousal. When she slept, she found herself dreaming about her next spanking.
Mr. Endicott, she quickly determined, was the man destined to cause her pain. Every morning that week, she had lowered herself across his knees to be spanked, and had arisen much later with the most intense feelings of frustration and distress. Every spanking seemed to build on the previous one, in every way. She realized that her lewd squirming was growing worse every day, and even though her ass was complaining bitterly about the burning pain, she was lifting her buttocks eagerly after the first six or eight swats. She found it increasingly impossible to sit comfortably at her desk, and was further embarrassed by her continuous squirming on her very tender bottom.
Friday night, after work, she had gone to a local bar and gotten very drunk.
She had awakened, naked, in a strange bed. Fighting panic, she had hastily covered herself with a sheet when a strange man, equally naked, had entered the bedroom carrying a tray. He seemed entirely unconcerned about his own exposure, setting the tray on a small table and pouring two mugs of steaming coffee. Louise realized that she must have let him pick her up last night, and had obviously shared his bed.
Smiling, he told her he would trade her a mug of the freshly brewed coffee for the sheet. Startled and embarrassed by the implications, Louise hesitated, then thought that he had obviously already seen her naked, and besides, the coffee smelled very good. She allowed him to draw the sheet away from her body. As she accepted the mug, she felt his eyes hot on her breasts, and she blushed to notice his cock growing rigidly erect. If HE was embarrassed, he hid it well. Over the coffee, he told her she was the most beautiful woman he had ever known.
The gypsy's predictions rang in her mind, one man to cause her pain, another to bring ecstasy. She didn't know his name, but plainly this must be the second man.
He finished his coffee and stood before her, his erection rising firmly from his belly, and asked
what he was bid for a heaping platter of ham and eggs? She had laughed at his audacity, then lay
back on the bed, spreading her thighs in invitation, and asked if this would be sufficient?
Grinning, he had joined her, entering her in one easy, well-practiced movement.
It was disappointing.
He was gentle, and enthusiastic, and praised her beauty continually, but he had boiled over almost immediately, leaving her thoroughly unsatisfied. She had lied that it was good for her too as he rose to prepare the breakfast.
That was disappointing too. The ham was overcooked and too salty, and the eggs runny. Well, the gypsy hadn't said he would be a good cook. She learned that his name was Bill. Just Bill, he insisted, no last name. That was a third disappointment.
She had stayed the weekend with him, with very mixed results. He was very attentive, always complimentary, and continually horny. If she so much as crossed her legs in a chair, he was instantly erect and eager for sex. But he had no staying power whatever. By Sunday night, when she returned to Anna's flat, she had not experienced a single orgasm in spite of being fucked almost continuously for two days. In a hot tub, she had masturbated desperately, bringing some release, but not nearly enough.
Monday morning's spanking was the worst one yet. Still aroused and frustrated from her weekend, she found Mr. Endicott's efforts almost unbearable. She had bitten her tongue to keep from begging him to fuck her after the lengthy punishment.
By Thursday, she was desperate. She saw the gypsy again, explaining that she had met the two men, but had not seen the situation resolved as she had expected. The gypsy raised her eyebrows and told her the cards had nothing more to say. She must make her own choices now. But, the old woman warned, the wrong choice would be disastrous.
That night, she had gone to Bill's flat, almost tearing off her clothes as soon as she walked in. He welcomed her eagerly, telling her in obviously sincere terms how much he had missed her. His eyes and hands on her bare tits had had her panting with arousal when he carried her to his bed.
And that was all.
He had fucked her, three times in rapid succession, but each time for no more than a few moments. His own obviously spectacular orgasms just made her more frustrated as she could never quite keep him active long enough to reach her own. In the middle of the night, she had left him asleep and fled.
Friday morning, when she presented herself to Mr. Endicott, he had a surprise for her. Since he would be away from the office the following Monday, he proposed to give her both spankings this morning, if she had no objection.
A double spanking? Louise knew she could never endure it. Eyes wide, she said she would agree on one condition, that he fuck her afterwards.
It had been Mr. Endicott's turn to be surprised. He asked if she meant that, and she assurred him that she certainly did. In that case, he had said, perhaps she should take this spanking entirely naked. Taking a deep breath, she had begun to strip.
Like Billy, Mr. Endicott was very complimentary of her body, but in very different terms. A magnificent rump like hers, he told her, should never be allowed to grow cold. A strapping, like the one she still faced, should be a common event in her life, and she ought never to go a day without a good spanking. Louise trembled as she assumed the usual position across his knees, but she realized that she was less frightened by the pending spanking than by the fact she was AGREEING with him!
It was a terrible spanking, the worst one yet. And the best. Her rump was on fire! And so were her loins. His exploring fingers had driven her closer to the edge of ecstasy than Billy had managed in a night of sex.
And when he pushed her off his lap, she had eagerly rolled to her hands and knees, offering him her reddened bottom. Mr. Endicott had quickly removed his trousers and knelt behind her. Almost as soon as she felt him enter her, she began to tremble in rapture. her orgasm, delayed so long was shattering. She nearly passed out.
As she was regaining her senses, she realized that Mr. Endicott was still in her, moving with slow expertise. Quickly her passions returned and she felt a second climax, this one not so powerful, but incredibly satisfying. And still her partner seemed unmoved by it all. As she was trembling a third time, she finally felt him tense and deliver his own orgasm into her.
She lay on his rug, naked, for nearly half an hour, unable even to rise. As she finally found her returning strength adequate to get up, she realized that he was fully dressed, and hard at work. Embarrassed, she had gathered her clothing and fled into his private bathroom to dress.
At her desk, later, she found herself unable to concentrate on her work. Nearly exhausted by her morning, she couldn't even bring herself to try to work on the stack of contracts on her desk.
One man would cause her pain and the other ecstasy; that's what the gypsy had said. She had assumed that Mr. Endicott's spankings were the former. But there were, she realized, different kinds of pain. Her buttocks assured her that her morning had been very painful indeed, but it was just a physical pain, one easily assimilated into her following sexual rapture. By contrast, her night with Billy had been gentle and sweet. And totally miserable!
If the gypsy was right, she was to marry one of these two. Mr. Endicott had already warned her what life would be like as HIS wife. She would feel the strap, and probably that wooden ruler and Heaven knew what else on her poor bottom more often than she cared to think about. Her ass would be on fire more often than not if she married HIM. But he would fuck her afterwards, REALLY fuck her! If this morning was any kind of indication, she would know the kind of ecstasy that novel writers talk about but no one really gets.
On the other hand, life with Billy would be peaceful. He was obviously in love with her, and would do everything he could to make her happy. She doubted that it would ever occur to HIM to spank her, let alone apply a leather strap to her bare bottom. But Billy would never satisfy her either. In two nights in his bed, she had YET to experience even a LITTLE orgasm, let alone anything like the shattering explosion of this morning.
At lunch, she went to see the gypsy again.
She tried to tell the old woman about her quandary, but she received neither sympathy nor guidance. The gypsy read her star charts and told her pretty much what she already knew. It was time to choose. Pain or ecstasy. But the gypsy had one piece of advice: she better make up her mind quickly. If she didn't choose soon, she would lose both men, and her future then looked long and bleak.
That afternoon, she made up her mind.
At four, she had knocked on Mr. Endicott's door. Without preamble, she asked if he had his strap available? Eyebrows raised, he had opened a drawer and produced the implement in question. Heavy and well oiled, more than two feet long and nearly three inches wide with a doubled handle at one end, it was rather obviously an old-fashioned razor strop. It would be, Louise was quite sure, terribly painful.
Taking a deep breath, she told him she had done almost no work at all that day, and plainly deserved a thorough thrashing. It would be best, she suggested if she were required to strip quite naked for the strapping, and that the three dozen she had been promised for an earlier offense seemed an appropriate sentence for her sloth.
Taking his agreement for granted, she began to strip. His eyes eagerly followed every revelation of her body, and she realized he had never seen her naked before that morning. She tugged off her last garment and posed for him. Then she said she would like to ask a favor. He nodded.
After she had been properly punished, she asked, would he be so kind as to fuck her again?
Mr. Endicott had looked at her for several moments. Then he said he would like to ask a favor of his own. Surprised, she had nodded in her turn.
He asked if she would consider accompanying him on his trip that would keep him out of the office next Monday?
She asked if he would bring the strap?
He assured her that he would.
Needing no further conversation, Louise walked to his sofa and knelt on the cushions. Spreading her thighs widely, she leaned forward to rest her crossed arms on the cushioned back, presenting her rump in obvious invitation.
As Mr. Endicott approached her, strap in hand, she seemed to hear the voice of the old gypsy congratulating her on her choice.
Copyright 1997 Hawkwood
