Heels: A Friend In Need

by Deane Christopher

 

Prologue

 

Several years ago, William Castle was dealing with the emotional fallout of a fairly messy divorce. Having taken his wedding vows seriously, Bill took the sudden and unexpected dissolution of his marriage hard. Though he and his wife had gone through some rocky times, Bill thought that he and his wife had ironed things out. Obviously his wife held with a different opinion.

Bill did not take the break-up well. In fact, once he faced the fact that his marriage was indeed over, he began to wallow in the black funk of depression. And though none of his friends or family thought that Bill was in danger of becoming suicidal, as his depression deepened it began to become a growing concern. However, as depressed as he was, there were two things that saved Bill from going off the deep end.

The first of those things had been his best friend, one Jeffery Whitehall. In the early weeks of the break up, Jeff had been there for Bill, doing everything he could think of and them some to try to bolster Bill's sagging spirits. Though it was anything but easy, Jeff fought an ongoing battle to keep Bill both busy and active. On Jeff's urgings, the two joined the local Y with their intention being to swim laps at least once a week. Granted, Jeff had to pressure Bill into going each and every Tuesday. But week after week, Jeff managed to somehow cajole Bill into meeting him at the Y's pool. Likewise, on Thursday evenings, Jeff pressured Bill into playing volleyball with a group of their high school cronies. After the games, the whole kit and caboodle of them headed over to an Irish flavored pub where they would cap off the night by shooting the shit with one another and they downing a few brewskies.

Though Jeff's intervention did help to lift Bill's sagging spirits, in the grand scheme of things it was little more than a stopgap measure. That is to say that it was not a cure-all for Bill's depression. Basically, Bill, in a zombie like fashion, went through the motions. Save for those rare and fleeting occasions, Bill, not wanting to put a damper on the proceedings, generally pretended to enjoy himself rather than setting his troubles aside, letting go and acutely enjoying himself. But all things considered, Jeff's ongoing struggle to keep Bill active went a long way in keeping Bill distracted from the woes that were doing a real number on his head.

That brings us to the second thing that saved Bill from being overwhelmed by the practically omnipresent doldrums that he seemed to relish wallowing in. And that thing, or more correctly those things, were the contents of a package that mysterious appeared on his doorstep one day. Keenly aware the he had not ordered anything recently, Bill first thought was that the parcel had been delivered to the wrong address, and that it probably belonged to one of his neighbors. However when Bill examined the address label, only to see his own name and address neatly printed on its face, he realized that he was indeed the intended recipient. Perplexing him all the more was the fact that both the address label and the return address label contained the same exact information, indicating in a nonsensical way that he had sent the package to himself. That of course was ludicrous, owing to the fact that Bill knew that had done no such thing.

Upon entering his house, Bill's first thought was to call the shipping company that had delivered the parcel in an effort to straighten out what he perceived to be an obvious mistake. Though the woman who answered the phone was sympathetic to Bill's quandary, the tracking number that was clearly printed on the shipping label bore no resemblance whatsoever to any tracking number the shipping company presently used, or for that matter, had ever used. Succinctly put, the woman politely informed Bill that the shipping company would not take the package back even if he were to try to drop it off at one of their distribution centers. As far as the shipping company was concerned, they had done their job. They had delivered the package to the correct address. Rightly or wrongly, the package and its contents belonged to the addressee, one William Castle.

Though slightly perturbed with the shipping company, Bill remained undaunted. Figuring that he would find some sort of invoice packed inside the parcel along with whatever merchandize it contained, Bill proceeded on to open the package. As one might expect, there was a whole slew of Styrofoam packing nodules cushioning what appeared to Bill to be a fairly standard sized shoebox. But there was no sign of an invoice. Figuring that the invoice must have been packed inside the shoebox, Bill continued on to lift the classy silver foiled top off of the shoebox's glossy black bottom. Once again, Bill found no invoice. What he did find inside the shoebox, wrapped in some sort of shimmering rainbow hued tissue paper, was a pair of extremely petite, black kidskin leather stiletto heeled opera pumps, along with a handsome calligraphy-penned note that contained but one word, with that word being 'Enjoy'. Setting the shoes aside for the moment, Bill examined first the shoebox, and then unusual tissue paper that the heels had been wrapped in, with the hope that they might give him a clue as to just who the manufacture was. Again, he found nothing. In a last ditch effort to determine who had mistakenly sent him what were obviously a pair of women's shoes, Bill turned to heels themselves, thinking that they would surely shed some light on the matter. However, search as he might, Bill once again came up short. With the exception of a small stylized 'Z" stamped in the bottom of the tiny heel cap of both of shoes, the pointy toed opera pumps bore no other markings to help Bill identify their origins.

Since he could not find out to whom he could return the pumps to, Bill figured that since he had no use for them himself, he would just go ahead and put the heels with the rest of the stuff he intending on eventually dropping off at Goodwill Store. However, just as he was about return the pumps to the shoebox they had come in, the phone rang, and he ended up leaving the heels sitting upright atop his living room's coffee table. And there they sat for the next several days.

Strange, but one of Bill's wife's ongoing complaints was that he was a neatness freak. However, on the day she walked out the door, that ever so irritating anal-retentive idiosyncrasy of his strolled out the door right alongside of her. To say that Bill's house was a mess would have been a kind way of putting it. In fact, a mess would have been a vast improvement over the disorganize quagmire that his house had quickly turned into in the wake of his wife's leave-taking. In all honesty, Bill's place looked as if a cyclone had not only camped out there, but had literally taken over the house's cleaning duties. In fact the mess got so bad at one point that even Bill's most unkempt friends began to find excuses not to stop by and pay him visit.

But, be that as it maybe, the significant point in all this is that the high heels remained on Bill's coffee table, standing upright, right alongside of the up-scale and extremely fashionable shoebox they had come in.

Several evenings later, as Bill sat on the sofa watching a baseball game between the home team and those despised New York Yankees, something monumental happened, something that would in fact change his life forever. Though he endeavored to keep his attention focused on the game, Bill found himself being at first distracted, and then intrigued, and finally preoccupied by the mere presence of the high heels.

Unable to discern why he was so attracted to the stiletto heels, Bill gave in to the compulsion to reexamine them. Picking up one of the ever so petite pumps, he proceeded on to turn it this way and that, as he diligently inspected it from every imaginable angel. Then, in an effort on his part to do a stare and compare, so as to determine the heel's approximate size, Bill hefted his left leg off the floor and rested the outer run of its ankle just behind the kneecap of his right leg. Having done that, Bill, using his right hand, positioned the heel in such a way so that he held it just beyond and parallel to the sole of his left foot. Though he wore only a man's size nine shoe, his foot appeared gigantic in comparison to the diminutive sized pump. That further perplexed Bill, for he could not envision a woman with a foot small enough to wear such a small shoe. A child, or perhaps a midget, might be able to wear such small pumps, but certainly not your average teenage girl, much less a full grown woman. And that begged the question as to why anyone would make that style of shoe in such a small size to begin with?

Bill never got around to pondering that question. Never sure as to what had motivated him to do so, Bill, in sort of a knee-jerk reaction, unthinking began to slide the open maw of the diminutive pump over the toe portion of the bulky-knit sock which enshrouded his raised left foot. Oddly enough and shocking the living shit out of Bill in the process, the high heel slide smoothly and comfortably into place about his foot.

As one might imagine, Bill was at a complete loss as to explain how a shoe that had no chance of fitting his foot, had done exactly that. Though snug, the heel neither pinched nor hurt. In fact, as flabbergasted as he was at that moment, Bill could not recall a shoe ever feeling as comfortable as the opera pump felt.

Then, startling him all the more, Bill became aware of the fact that his left foot, the very same foot upon which now sported an ever so provocative stiletto heeled pump, was no longer wearing a white bulky-knit sock. Rather, his left foot was enchantingly encased in the coffee brown weave of sheer nylon hosiery.

"What the fuck's going on here?" Bill frantically exclaimed, as he reached down, and with a harsh yank, pulled the spiked heel clear of his foot, only to see the hosiery that still encased his foot began to noticeable lighten, as it progressively made the transition back into a bulky-knit sock.

Having taken a rather protracted moment to assess what had just transpired, a thoroughly bewildered, but nonetheless extremely intrigued Bill decided to repeat the experiment. Chiding himself to pay close attention, a badly shaken Bill timidly slid the pump unto his awaiting appendage. "Well, I'll be dammed!" an astounded Bill bemusedly muttered, as he watched his sock transmogrify into a nylon footy; a footy whose upper extent began to flow steadily up his leg, to the point where the hosiery actually passed beneath the gathered cuff of the sweatpants he was wearing.

Not sure what to make of what was happening, Bill once again reached down and plucked the high heel from off of his foot. As he did so, the sheer nylon material encasing the lower portion of his left leg began to recede, as it progressively changed back into a sock. However, it seemed to Bill that it took a tad bit longer for the sock to reconstitute itself than it had previously.

Pushing the elastic hem of his sweatpants to just below his knee, Bill repeated the experiment for a third time. On this occasion, Bill allowed the sensual mesh of the nylon material to climb all the way up to mid-calf level before he reached down and lifted the opera pump clear of his foot. Not only did the transition from nylon hosiery back to wool sock take longer than it had before, but Bill thought that upon removing the spiked heel that his foot looked considerably more like a woman's foot than it did a man's. And the reason he initially thought that was because his foot looked smaller, smaller and cuter, and its' instep appeared to have a markedly higher arch than he ever remembered it having before. However, that impression of his soon passed, leading him to assume that his perception had gone wacky, and that his eyes had to be playing tricks on him.

On the fourth go-around, Bill held off removing the stiletto until he felt the nylon hosiery climbed to the mid-point of his left thigh. Immediately upon removal of the pump, a quick stare and compare of both of his feet confirmed the fact that his eyes had not deceived him. His left foot was indeed smaller than his right foot. Likewise, the instep of his left foot was at that particular moment in time arched higher than that of his right foot. Added to that, Bill realized that the shoe he was holding appeared to be a good deal larger than the one that still resided upon the coffee table, even though the one he held was already in the process of shrinking back to the diminutive size of its mate.

Even more intrigued than he had been before, Bill decided to switch feet. As expected, the other pump had the same effect on his right foot as its counterpart had had on his left foot. Bill also took note of another rather fascinating change that was occurring as the nylon hosiery fluidly flowed upwards towards his groin. The leg that the hosiery so sensually climbed was being systematically re-sculptured, going from a man's hairy and muscular leg to the alluring symmetry of a woman's ever so smooth, hairless, and sexy lower appendage.

Having reached the conclusion that the time for experimentation with just one foot was over, Bill reached down and adroitly plucked the pump from off of his right foot. Anxious to see what would happen when he tried on both shoes at the same time, Bill became impatient as he sat there waiting for his right leg to return to its normal manly disposition. Once it did, just to be on the safe side, Bill decided to give it another two minutes before proceeding.

Though he did so with a good deal of trepidation, Bill, starting with his right foot and moving immediately to his left, donned the heels. As before, the dirty white bulk-knit socks he was wearing began to metamorphose into coffee brown nylon hosiery. 'Damn!' he thought. 'I should've had the good sense to take off my sweatpants before I started. Oh, well...'

Oddly enough, as the heels' feminizing effect reached just beyond the level of those knobby knees of his, Bill realized that the sweatpants he was wearing were also being affected by what he had begun to think of as the inherent magical wherewithal of the heels. Though still baggy about the upper third his leg, the bottom two thirds of his sweatpants appeared to Bill to have constricted to form body-hugging leggings. And that was not the only change that his sweatpants were in the process of undergoing. While the baggy top one third was still a drab cotton/polyester mix, the body hugging bottom two thirds had the sheen and feel of a slinky nylon/lycra weave.

"Oh, my God!" Bill clamored, as he felt an eerie, though not all that unpleasant tingling sensation flow upwards through his groin. In an attempt to assess the damage, Bill thrust her right hand under the elastic waistband of the shimmering nylon/lycra leggings that showcased those shapely and ever so sexy legs of hers.

Even as her probing fingers came in contact with the multiple lip folds of that new, ultra feminine crease of hers, Bill felt her waist constrict and her tummy flatten. 'Holy shit!' her mind shirked. 'My pecker's gone! This is crazy. I've actually got a vagina down there now. These heels, they're actually changing me into a girl.'

Right then and there, Bill panicked. Hoping against hope that the damage could be undone, she hastily bent down and practically tore those magical high heels from off of her feet. A tense moment or two followed as Bill desperately tried to discern if she was beginning to retrogress back into manhood.

She was. And that made him very, very happy, to the point where he actually became ecstatic about it.

Ten minutes later, after a good stiff drink of scotch to bolster his resolve, Bill decided to have another go at it. However, before he donned the heels, he prudently relocated to the upstairs bathroom so that he could better monitor what was occurring in the full length mirror that was affixed to the back of the bathroom door. He also decided to take off all of his clothes. That way he could watch as that manly member of his reconfigured itself into a woman's pussy. Needless to say, a thoroughly turned-on Bill was amazed at not only how fluidly, but also how rapidly the transsexualization of her loin's occurred.

As soon as he stepped into the stilettos, Bill became aware of two things that he hadn't noticed before, owing to fact that prior to this he had been far too preoccupied with the primary changes that his donning of the heels invoked. First off, he realized that the mere act of wearing the pumps had made him horny as hell. Secondly, his horniness caused his pecker to engorge blood at an accelerated rate. That being the case, by the time the lower portion of his legs were those of an attractive woman, Bill was well on the way to sporting a first rate hard-on. Fighting the urge to jerk-off, Bill looked on in amazement as his blood-engorged penis began to swiftly dwindle down to the size of an infant's ere the multiple lip folds that had formed out of his testicles extended forward, fluidly engulfing the ever so sensitive clitoral nub that her penis had miraculously transmogrified into.

Though Bill was far to preoccupied with the changes that his primary sexual equipment was undergoing to notice, several other rather noteworthy changes were occurring almost simultaneously. That manly hung and hairy ass of Bill's was being re-sculptured into the ever so scrumptious, hairless, heart-shaped derriere of a lovely young sexpot's. Concurrent with that, Bill's hips splayed mere seconds before her waist began to contract, there by completing two-thirds of the bodacious hourglass figure she was destined to have.

Gazing at herself in the mirror, Bill had to laugh at how absolutely ludicrous she looked at that point in the proceedings. There she was, every bit the lovely young woman from the waist down, while from the waist up, she was still was very much the hairy chested man she had always been.

Though her beer-belly was only in their early stages of development, owing to the fact that Bill watched what she ate and tried to keep fit by exercising, and more recently swimming laps several times a week at the Y, she really enjoyed watching her budding stomach-paunch flatten out and form itself into a taut and trim little tummy.

Fancying herself a true connoisseur of women's breast, Bill eagerly anticipated the development of her own mammary glands. Oddly enough, she was initially disconcerted when that manly chest of hers lost all semblance of rigidity and droopily sagged. However, within a few seconds, Bill fears began to subside, as her areola began to both darken and enlarge. Concurrently to that, the area immediately surrounding her teats began to inflate in a balloon-like fashion into the slightly raised nubbins that are the hallmark of a female's early adolescence. A half a dozen heart beats after that, though her bosom was still on the small side, Bill could definitely lay claim having a pair, albeit not what she would ascribe to being a truly great and upstanding pair. But Bill's breast development did not stop there. The ballooning effect continued to expand those chest melons of hers to the point where Bill was starting to become fearful that her mammary might grow to gross proportions.

Luckily, that did not happen. Her breast development stopped at ample, or as Bill would later come to call it, the Goldilocks Point, with that point being neither to small, nor to large, but to her way of thinking, just right.

In Bill's admittedly biased opinion, her breast were about as perfect as perfect could be. She could not envision any woman with better breast than those magical high heels of hers had fitted her out with. Added to that, not only did they look absolutely fantastic, one touch, one teasing little finger-swipe of her nipples, confirmed the fact that they were as sensitive as all get-out.

Taking another look at herself in the mirror, Bill's mind clamored, 'God! Am I a sight, or what?'

And Bill was right. She was a sight. From neck down she was all woman, fitted out with a body that wouldn't quit. However, sitting atop that ever so alluring body of hers was perched a head that was still as masculine as it ever had been. Add to that, making her look like some sort of grotesque sexual amalgamation, her arms and hands were still very much that of the man she had been born to be.

Curious to see how she would look as a female, Bill had initially planned to allow the transsexualization process to run its course. However, as her neck began to take on the appearance of refined elegance, she began to second-guess herself. Then, just as her five o'clock shadow was beginning to fade from that manly sculptured face of hers, fearing that she would be stuck as woman for the rest of her life if she allowed the transsexualization to go full-term, Bill panicked and frantically stepped out of the heels.

Oddly enough, though she was extremely relived on one hand to see that her body was indeed changing back into that of a man's, Bill was thoroughly pissed-off at herself for chickening-out. In fact, she was so pissed-off at herself that she began to verbally castigate herself for being such a ninny about the whole thing. Much like the character Gollum in J. R. R. Tolkien's Lord of the Rings saga, Bill began to verbally debate with herself the pros and cons that were involved were she to go whole hog, and allow the transsexualization to run its course.

The logically aspects of Bill's mind questioned, 'Do you really want to see what you looked like as a woman?'

The emotional aspects of Bill's mind responded, 'Yes, very much so!'

That prompted the logically aspects of Bill's mind to pose another question. 'Do you think that if you let the process run its course you'll end up stuck as a woman?'

To wit, the emotional aspects of Bill's mind responded, 'No, not really. Given the way the heels seem to work, I'm inclined to believe that once I take them off, I'll simply change back into my old self.'

That answer caused the logically aspects of Bill's mind to ask yet another question. 'Yeah, but what if that's not the case? What if you're wrong about that, pal? Tell me, what the hell are you going to do if you find that you have to spend the rest of your life as a woman?'

The emotional aspects of Bill's mind responded, 'I don't know. What I do know is that I really want to try this. Look, I know it's risky. And I know that there's no way I could handle being a woman on a twenty-four seven bases. But I still want to try. I mean, I'll never forgive myself if I don't.'

In the end, round about the time that her fledgling beer-belly was beginning the process of reasserting itself, Bill's emotional side won the debate. In an effort on her part to restart her male to female transsexualization before her male genitalia put in a re-appearance, Bill nimbly stepped into first the right pump, and then the left.

It worked. As soon as the stilettos were back on her feet, the transsexualization process did an immediate one-eighty. Bill, though still apprehensive over what might or might not transpire, was nevertheless elated over the fact that things seemed to be back on track, and that she would soon be fondling and caressing the super-sensitive nipples of those magnificent new breast of hers once again.

Several minutes later, with a come-hither voice that gushed with raw and eager sense of sensuality, Bill giddily gasped, as coil after coil after of honey-gold terseness elongated to a point where they began to cascade down the middle of her back. "Oh, my God!" she joyfully shrieked. "I can't believe how beautiful I am! I mean, even if I do say so myself, I am one fine looking woman if ever there was one! I don't know how these heels did it, but I've got to admit that they done good! I look terrific! Hell! I look so good right now that if I still had that trusty old pecker of mine, it'd be standing at attention, and chomping at the bit for me to jump in and lend a hand..."

Though Bill's elation never entirely subsided, her growing sense of apprehension about whether or not she could ever return to her manly state did tend to take the edge off of it. That is to say that she was betwixt and between as to what she should do. Her indecision tormented her. Now that she was a woman, at least in a purely physical sense, Bill wondered is she should she do the prudent thing, and just go ahead and remove the heels to see if she would start to revert back? Or, should she do what she really wanted to do, and take some time to both explore and enjoy that bodacious new body of hers?

After a rather heated debate with herself, Bill reached a compromise. She would give herself a good fifteen minutes as a woman before removing the heels in order to see whether or not she would revert back.

Well, needless to say that once Bill got around to investigating how all those new erogenous zones of hers worked that fifteen-minute timeline hers went right out the window. An hour and a half later, having finger-flicked herself into a state of orgasmic ecstasy several times in quick succession, Bill, who was now a self avowed narcissist and a nymphomaniac to boot, came to the stark and troubling realization that she may have imprudently overstayed her welcome. In a knee-jerk reaction that was anything but lady-like, Bill quickly reached down and removed the stilettos, hoping and praying that she would begin to change back into a man in short order.

To Bill's chagrin, nothing happened. She remained the woman she was.

Riding roughshod over the damn near overwhelming and omnipresent urge to give into panic, Bill chided herself to give it five minutes, as if there was anything she could do about the situation then.

Five minutes became ten minutes and then fifteen and still Bill could see nothing to give her hope that a change back to normalcy was in the offing. For all Bill knew she was going to be stuck as a woman for the rest of what would now be a most unnatural life, owing to the fact that while her body was indeed as female as female could be, she perceived that her mind staunchly retained its manly orientation. One look at herself in the mirror was all Bill needed to confirm the fact that mentally speaking, she was still very much a man, a man who possessed not only a very healthy male libido, but also an extremely vivid and, in light of her new sexual status as a fully functional female, a lecherous and perverted imagination as well.

To say that Bill was pissed would have been the grossest of understatements. Though she had thoroughly enjoyed getting off as a girl, and would not mind being able to do so again, Bill desperately wanted to be a man again. The problem was that she had no idea how to achieve that desire of hers. She tried wishing. She tried praying. But nothing she did worked.

As frazzled and annoyed as she was, Bill went from being pissed to being paranoid in the blink of one of those ever so tantalizing baby blue eyes of hers. Given the heels had mysteriously shown up on her doorstep, Bill began to suspect that she was the butt of someone's cruel joke. That or someone really had it in for her. Grabbing a pencil and a piece of paper, she divided the sheet of paper into two columns and hastily began to jot down a list of possible suspects that fit either one, or the other, or in some cases, both of the categories.

Having done that, Bill began to run through both lists, evaluating, and by in large, eliminating names for one reason or another as she proceeded down the list of names she had jotted down. A second run through the lists whittled the possible suspects down to one sigh of a handful. Two were practical jokers. Another guy hated Bill's guts. And then there was Bill's ex.

While she sat perched on the edge of her bed, unaware of the fact that she had started playing around with one of those sensitive nipples of hers, an extremely distraught and overly suspicious Bill began to carefully reexamine the remaining four suspects. Grudgingly, Bill came to the conclusion that it was unlikely that either one of the two practical jokers that she knew would go to such extremes to pull off a prank.

The same could be said of that slimy son of a bitch who hated Bill's guts. The simple fact was that the bastard had neither the smarts nor patience to pull off something in the nature of the heels. While there was little doubt that SOB would have gotten a real kick out of turning Bill into a member of the opposite sex, knowing the guy as Bill did, Bill knew that he would not have left something like that to chance. Plus, the bastard would have wanted to be on hand to see Bill go from guy to gal. Then, knowing pretty much how that immoral asshole thought, Bill knew that the bastard would have found a way to forced her into going down on him, before getting down to the business of reaming her out.

That left Bill with one other person to consider, with that other person being none other than her ex-wife, Susan.

If someone had indeed sent Bills the heels with the hope that he would eventually try them on, and end up getting stuck as a female for the rest of her life, that person could have been Susan. Though Bill had not been aware of it prior to marrying her, he found out shortly after he did so that she was not what one would call a nice person. Susan had a short fuse and an extremely vengeful nature. Added to that, Bill had to admit that his ex was also both patient and diabolical enough to have sent him the heels. Susan was also a New Age kook, who bought into anything that even hinted at being of a metaphysical nature.

However, after careful consideration, Bill, who had once again started playing around with that new clit of hers, came to the conclusion that her ex could not have been the person responsible for sending her the heels. Bill based her reasoning on her ex's vanity. There was just no way that Susan would ever turn Bill into a woman who was prettier than she was. There was no way that Susan's vanity would allow something like that to happen.

After almost an hour and a half of trying to figure out who might have sent the high heels to her, a very horny and turned-on Bill was back to square one. While she was half tempted to call a few of the people that were on her short list of suspects, and demand that they tell her how to go about changing herself back into a man again, Bill thought better of it. Faced with the ignominy of having to confess that she had actually been foolish enough to have allowed her transsexualization to go full term, Bill realized that she did not want anyone to know how badly she had been duped, if in fact she had been duped.

Though it was a small hope at best, Bill, who was struggling hard to remain optimistic, hoped and prayed that those magical high heels of hers worked something like Cinderella's glass slippers, and that she would begin to change back into a man again at the stroke of midnight. The trouble with that was the fact that Bill's was not anything close to an optimist. She was a pragmatist, who endeavored to take the realistic view of things. Trouble was, whenever Bill offered a realistic view of any given situation, more times than not, he tended to sound more like a pessimist than he ever did an optimist. That was because the School of Hard Knocks had taught him that reality has a marked tendency to suck.

While she sat there on her bed, twiddling around with that nifty new clit of hers, Bill, aware that there was nothing she could do that night to get her old body back, decided to once again enjoy the perks of her new found femininity.

'Damn!' she thought. 'This new clit of mine sure feels a whole hell of lot bigger than it did earlier. Strange...' Bill was even more perplexed. 'Not only does it feel a good deal larger than it did before, it's nowhere near as sensitive as it felt earlier...'

Glancing downwards towards his groin, Bill failed to immediately recognize the fact that his view was no longer obstructed by those conical new endowments of his. Had he, he would have realized that he was well on the way to regaining his manhood. However, given his rather frazzled state of mind, Bill did not at first pick-up on the fact that he was in the process of changing back into a man again.

Aware that something was not as it should be, a befuddled Bill stared at his loins only to realize the fact that he was no longer fingering the elusive nub of a woman's clitoris. Though it took him a moment or two, it finally dawned on Bill that instead of fingering a woman's clitoris; he was instead employing the thumb and index finger of his right hand to ardently stroke a penis that was about the size of a toddler's.

"Well, what do you know! I've got my trusty old pecker back!" an extremely relieved and jubilant Bill joyously proclaimed, as he watched his penis continued to grow both larger and thicker. "Thank you, Lord! Thank you for changing me back into a man again!"

Though Bill had half a mind to try those magical high heels of his on again, he did not want to tempt fate. That being the case, he decided to do the prudent thing, and call it a night. But before he did that, Bill prudently picked up the discarded heels and, clearing a spot for them on his dresser, placed them there.

Needless to say, Bill was not very productive the following day at work. He was by far too preoccupied with thoughts of the heels, and how they had changed him into a bona fide woman. Added to that, he found that he was being constantly distracted by thoughts of how utterly fantastic he looked as a femme fatale. Worse, the damn near omnipresent memory of the unbelievable amounts of sheer unadulterated pleasure that he had had enjoyed as a woman made it damn near impossible for him to concentrate on anything that was work related. Throughout the day, all Bill could think of was going home and slipping back into those marvelous high heels of his.

As obsessed as Bill was thinking about those magical high heels of his, on his way home from work he began to piece together a theory revolving around the amount of time he had spent as a female after removing the stilettos. Reasonable sure that he had an explanation as to what had happened, Bill planned on putting that theory of his to the test as soon as he got home.

And that is just what Bill did. As soon as he got in the door, he sprinted up the stairs and into his bedroom. A moment later, he had his loafers off and was slipping those manly sized feet of his into those ever so petite heels. Taking a quick moment to jot down the time, Bill, oblivious to just how nimbly he maneuvered while wearing such perilous footwear, fairly dashed into the bathroom, and began to check himself out in the full-length mirror that awaited him there.

Bill, who was already horny from the day-long anticipation of what was to occur, became even hornier as he watched his body, and the clothes adorning it, make the steady and fluid transition from male to female. "Oh, my God!' she thought, as the charcoal slacks she had been wearing transmogrified into shimmering black Lycra/Spandex leggings. 'Have I got a great pair of legs, or what?' Several minutes later, as the white bulky knit sweater she was wearing smartly conformed to attractively showcase that new cleavage of hers, Bill, who had already started to teasingly caress that portion of the Spandex leggings concealing that revamped crotch of hers, mused aloud, "Holy, shit! Now that, my friend, is one fantastic set of knockers if ever there was one..."

Having worked herself into a sexual frenzy, Bill, her voice still a manly baritone, narcissistically clamored, "I can't stand it any longer! I've just got to get these clothes off so that I can have at myself!" Then, upon the realization that she would have to take off the heels in order to remove the leggings encasing her lower half, Bill, whose vagina had already begun leaking love-juices like a sieve, shit-canned that idea out of hand, opting to only remove her sweater for the time being. In a frantic, to be almost spastic, unlady-like performance, Bill yanked and tugged that ever so flattering fisherman knit sweater up and off her torso. 'Well, what do you know!" she sensually exclaimed with that silky smooth contra-alto voice of hers. "I'm wearing a bra. The T-shirt I was wearing must have up and changed into one. Well, isn't that convenient? And it's satin, no less! Imagine me, wearing a bra. Too bad it and these tights I'm wearing aren't silver. I just love seeing women wearing anything silver..."

At that precise moment in time, something occurred that shocked the living shit out of Bill. Even as she expressed her liking for women trussed up in shimmering silver duds, her pearl-white bra, and slinky black leggings, along with the heels themselves, instantaneously adopted a dazzling silver luster.

"Oh, my God!" she giddily clamored. "What the hell just happened? What the hell's going on here? I say I like seeing women decked out in silver, and just like that, everything I'm wearing is silver! Hell, even these heels of mine are now silver. This is great." Bill was ecstatic. "I wonder what else these heels of my can do..."

In the days and weeks that followed, Bill, through a lot of trail and error, pretty much provided answers for that very apropos question of hers.

Bill's hunch about lag girl-time proved to be correct. There was indeed a penalty time enacted each and every time he wore the pumps. For every unit of time Bill wore the heels in order to change himself into a bona fide member of the opposite sex, she would spend a like amount time as a female once she took off those magical high heels of hers. That is to say that if Bill spent an hour as a woman while wearing the heels, and then took them off, she would be penalized, and have to spend another hour as a femme fatale before she regressed back into a man again.

Co-opting a term he had learned when taking a course to become a certified scuba diver, Bill began to refer to this penalty, or lag-time, as Residual Girl Time.

Though the Residual Girl Time issue posed a potential problem for Bill, it was easily manageable. All that was needed was a little foresight, and some basic record keeping. The truth is that the only time that the Residual Girl Time business came close to causing a problem for Bill occurred one spring, a year or so after he came into possession of the heels. For some reason or another, Bill forgot to take into account the enactment of Daylight Saving Time. Owing to that oversight of his, Bill, who was scheduled to work that Sunday, woke up to shocking realization that he was still a she. Needless to say that Bill went into work an hour late that Sunday; earning him one glaring awshit from his asshole of a boss, which in turn, negated a hundred of those hard earned ataboys that he had managed to accumulate since his last evaluation.

Basically, the way Bill had it figured, weekdays did not present any problem whatsoever. If he had nothing planned, and so opted to spend the evening femmed-out to the max, as long as she took off the heels before midnight, she'd revert to being a man again before six the following morning. Weekends were another matter. Unlike weekdays, weekends required a little planning on Bill's part. And given the fact that Bill did not let to many days go by without logging a little girl-time, there were only a handful of weekends in which Bill did not spend at least a few hours as a certified member of the crotch creased club.

Bill was also quick to pick up on the fact that not only did the heels change any male attire he might be wearing into female attire, they also allowed her to drastically modify that female attire into anything that tickled that rather perverted male fancy of hers. That is to say that once female, Bill found that she could use the heels' inherent magical wherewithal to instantaneously reconfigure the garments she was presently wearing into anything that little lecherous heart of hers could devise. In other words, Bill could go from wearing a skimpy bikini to the splendor of an alluring evening gown in the mere blink of an eye. All she had to do was picture what she would like to be wearing in that staunchly male mind of hers, blink and - Whalla! - that is what she would find herself wearing.

When it came to Bill's magically manufacture feminine attire there was one interesting little codicil that the heels religiously enforced. The heels ensured that as a woman, Bill would always look her very best. No matter what Bill elected to wear when operating as a female, it would be both pleasing to the eye, and extremely flattering to that curvaceous figure of hers. Needless to say, Bill thoroughly enjoyed the ability that allowed her to alter her feminine attire to suit those manly couched whims of hers to the point where when it became time to clean the house, more times than not, Bill would do so decked out in the satin finery of a scantly clad French Maid.

As a woman, Bill took great pains to tease, and to please that healthy male libido of hers, adorning that sexy body of hers in all sort of fetish attire. Though she generally liked to lounge around the house in Lycra/Spandex tights, and either a bulky-knit sweater or luxurious satin blouse, occasionally Bill would opted for something along the lines of a Playboy Bunny Costume, or if not that, an I Dream of Jeannie styled harem girl ensemble.

In fact, it was the fetish attire business that led Bill to discover another rather novel and titillating facet of the heels' inherent magic. One evening while putting on a flash fetish fashion show for herself, Bill blinked herself out of a Dallas Cheerleader Outfit and into not only the stunning silver wetsuit that Angelina Jolie wore in Tomb Raider II, but into the spitting image of Angelina Jolie herself. Though shocked and amazed at first, Bill, not one to look a gift horse in mouth, decided in short order to put that new found talent of hers to the test. Grabbing an Entertainment Magazine to use as a point of reference, Bill began flipping through the pages, assuming the appearance and attire of one gorgeous babe after another as she did so. As a woman, Bill found that she could be tall or short, white or black, Oriental, or Asian, African or European, or any conceivable mixture. She could chose her eye color, her hair color, the length of hair, and whether that hair of hers was kinky, curly, or straight. She could pick her complexion, and damn near any other physical attribute that one could call to mind. Once on a whim, just to see hard far she could push the envelope, Bill went so far as to change herself into a blonde harried, blue eyed, ebony skinned Australian Aborigine.

There were several things that Bill could not do. For instances, the heels would not allow Bill to change herself into an unattractive woman. The heels were adamant that as a woman, Bill was going to be on the beautiful, to drop dead gorgeous side of attractive. In like manner, the heels would not allow Bill to change herself into either a prepubescent female or postmenopausal woman. The age of the woman Bill became had to fall within the nominal parameters of menstruation. Generally speaking, Bill liked to look in her early to mid-twenties when operating out in public as a female. It should also be noted that even though the heels allowed Bill to assume the appearance of any attractive menstruating female, once the novelty passed, ninety-nine percent of the time Bill spent femmed out to the max, she did so as the twenty-something, knock-down, drop-dead gorgeous blonde bombshell that her heels had initially turned her into.

 

+

 

 

Back in the beginning, back when Bill first began using the heels to turn himself into a bonfire woman, he was like that kid in a candy store that you are always hearing about. To put it bluntly, Bill found the sheer novelty of being able to spend time as a member of the opposite sex so erotically compelling that he spent almost all of his downtime as a female. But more than anything, as perverted and perverse as it might sound, Bill loved the multi-orgasmic rush that she enjoyed whenever she tickled that new fancy of hers, so much so that Bill quickly became mentally addicted to getting those female rocks of hers off.

As much as he enjoyed lounging around the house as a female, Bill found the prospect of going out in public as one to be quite daunting. He was absolutely terrified of attempting it. As far as Bill was concerned, turning oneself into a woman was one thing. Functioning as one out in the public eye as one was something else altogether.

As a man, Bill always had an aversion to feeling conspicuous. He did not like to stand out in a crowd. When and wherever possible, he liked to blend in. However, given how fantastic he looked decked out as a woman, Bill realized that people could not fail to notice her. Women, he presumed, would have a marked tendency to be envious of her good looks. And as far as men were concerned, Bill held no delusions. There was just no getting around the fact that men would be constantly eyeing his female persona up one side and down the other. And just the thought of having guys according him as a piece of eye-candy unnerved Bill to no end.

Somewhere around six weeks after those magical high heels had mysteriously appeared on his doorsteps, a bad bout of cabin fervor, working in conjunction with his renewed sense of self-confidence, drove Bill to make a monumental decision. Though it took a lot of soul searching on his part, he came to the conclusion that it was high time for him to venture out of the house for the first time as a member of the opposite sex. Donning the heels, Bill fought the urge to chicken out as he crammed that well entrenched male ego of his up inside of that nifty new honey pot of hers. Then, aware that that the slinky black catsuit that her pajamas had on their own accord transmogrified into were inappropriate attire for the day ahead, Bill opted for something of a more casual nature. Closing her eyes, Bill proceed on to blink herself into an outfit that consisted of a lightweight black leather jacket, a white turtleneck sweater, a pair of skintight designer jeans, and of course those magical high heels of hers.

Feeling as if everyone in the neighborhood was watching her, Bill rode roughshod over her inhibitions as she endeavored to casually saunter out to the curb where her pickup was parked. Climbing in behind the wheel, she adjusted both the front seat and the rearview mirror in order to compensate for her female body's slightly shorter stature. Turning on the ignition, Bill took a deep breath as a means to reinforce her resolve. Chiding herself that everything was going to be fine, and that no one would pick up on the fact that she was not really a girl at heart, an extremely nervous Bill headed off for a day of window shopping at the mall.

All things considered, the day went off a lot better than Bill had expected it would. While it was true that men were constantly giving her the hairy eyeball, Bill handled it far better than she ever thought she would. Truth be told, save for a few random occasions in which a few men's stares where so blatantly threatening that they unsettled her, Bill found that once she got passed the all the ignominy involved, she began to actually enjoy the extemporaneous thrill she derived when men gazed at her admiringly. Though she refused to admit it even to herself, as time went on Bill began to really enjoy playing the part of Little Miss Innocent, the dick teaser's dick teaser.

After that initial occasion of venturing out in public as a female, Bill began doing so with increasing frequency. In fact, after a time, practically all of his mundane shopping, such as grocery and the like, was accomplished while functioning as a member of the fairer sex.

The heels began to restore Bill's confidence and sense of self-worth. And as his confidence grew, women who would not have given him the time of day in the wake of his wife's leaving, eagerly began to acquiesce to going out on a date with him. Once on a date, Bill's newfound familiarity with the various ins and outs of the female anatomy, came into play. As one might expect, the insider knowledge Bill possessed of the subtle workings of all the various female erogenous zones, as a rule resulted in Bill's date inviting him in for a nightcap, with that nightcap involving a lot more than just something to drink. Needless to say that once the word of Bill's sexual prowess as a slow-handed lover got around, he became a sought after commodity with the ladies.

Having only dated a handful of women before hooking up with his soon to be divorced wife, Bill made the most out of his newfound popularity with the ladies. In other words, Bill took up a new hobby, with that hobby being none other than the tongue in grove pursuits of an amateur gynecology. Like a kid in a candy store, Bill went on a sexual binge, as he began to bed one woman after another, in an all out effort on his part to add notches to his thighbone.

Eventually, Bill began to tire of playing the field. While it was a hell of a lot of fun for him at first, Bill found that the amount satisfaction he derived from hoping from one woman's bed to another had begun to diminish as the number of women he bedded markedly increased. Somewhere along the line, after a good deal of soul searching, an extremely tuckered out Bill came to the conclusion that what he really looking for was quality over quantity.

That being the case, Bill began to date with his goal being to establishing an exclusive relationship with one woman at a time. And, for the most part, that is essentially what he did, with those one-on-one relationships of his lasting anywhere from several weeks to somewhere in the neighborhood of six months or more. Bill even went so far as to fall, if not in love; at least in lust with a handful of the women he dated. In fact, there were several women who forced Bill to consider the possibility of his getting married again.

But there were several closely related problems that factor into that rather monumental decision.

The first problem was that the heels had turned Bill into a narcissist of the First Water. The woman he was infatuated with most was none other than his own feminine alter ego. That meant that none of the women he entered into exclusive relationships with could ever measured up to his own feminine alter ego. Added to that, what Bill was looking for in a woman was someone who could not only accept him in both his male and female personas, but also engage in sexual relationships with both of those sexual persuasions of his. Being the realist that he was, Bill knew such a woman would be hard to find. And if he ever did find such an understanding and sexually ambidextrous woman, Bill was not at all sure how he would go about broaching the subject of his sexual duality.

As it happened, the heels, mysteriously showing up on his doorstep as they had, proved to be Bill's salvation. For all intent and purposes, they turned his life around. They proved to be the major factor involved in rebuilding his sense of self-worth. Basically, they made him feel good about himself. All things considered, even if it meant that he would remain a bachelor for the rest of his life, sexually speaking Bill felt that those magical high heels of his afforded him the best of both worlds. While he thoroughly enjoyed being the man he had been born to be, there was no getting around the fact that he also relished his almost daily sojourns as a vivacious young woman.

To put it bluntly, the heels allowed Bill the ability to live a very self-centered, to the point of being almost selfish, self-contained life. And while it is true that there were times, though infrequent and of short duration when he did just that, Bill was by far to gregarious an individual to cut himself off from friends and family for any extended period of time. As much as he treasured the time he spent operating as a female, Bill treasured the relationships he had with friends and family. However, fearing that it would be a rare individual who would be either understanding enough, or tolerant enough to abide his frequent forays into the fascinating world of the feminine mystique, Bill closely guarded the secret life that the heels afforded him. Though there were times when he felt the pressing need to tell someone about the heels and how they allowed him to function as an anatomically correct member of the opposite sex, he always thought better of it, save when it came to his sister. Though it was not easy thing for him to do so, Bill, feeling the pressing need for some coaching when it came to the ins and outs of the feminine mystique, looked to his sister for help.

Though Beth Castle was constantly poking fun at him and calling Bill names such as the pervert in petticoats, or her brother the transsexuals' transsexual, Bill's sister proved to be a real godsend. Without any qualms or qualifications, Beth took Sara, the name Bill had chosen for his feminine alter ego, under her wings and taught her how to accord herself as the young woman she appeared to be. In fact, as time went on, Beth confessed that she enjoyed spending time with her sister, Sara, more than she ever did with her brother, Bill. Though she was somewhat inebriated at the time, one evening while the two 'sisters' were commiserating with each other over a bottle of Chardonnay, Beth went so far as to teasingly imply that it was a real shame that Bill had not been born a girl. Slurring her words ever so slightly, Beth continued to point out the fact that Sara had a real zest for life, where as she found her brother her brother Bill was a real stick in the mud. Oddly enough, Sara, who was felling any pain either, found herself in total agreement with her sister's assessment.

 

Chapter 1

 

Three and a half years after he came into possession of those magical high heels of his, Bill was living what he deemed to be a rewarding, somewhat selfish, and generally carefree life of a bachelor slash part-time bachelorette. Having amicably ended a seven-month relationship with a very nice young lady, Bill was in one of his infrequent dating dry-spells when his oldest and dearest friend, one Jeff Whitehall, called early one evening and informed Bill that his wife, Stacy, had up and left him. Knowing that Jeff would take the break-up hard, Bill did not waste a minute. Grabbing his wallet, watch and his keys, Bill bounded out the door of his house. Climbing in behind the wheel of his pickup, Bill sped off to spend the evening commiserating with Jeff over the apparent dissolution of his friend's marriage.

As Bill suspected, Jeff was devastated by his wife's unexpected announcement that she was leaving him, and that he would be hearing from her lawyer within the next week or so. Jeff, having admitted to Bill that he and Stacy had been going through a rather rough spell, seemed to think that things were getting better. Apparently Stacy held another opinion.

Having gone through a rather messy divorce a few years prior himself, Bill knew that his friend was in for bad spell. But as bad as had been for Bill, it soon became apparent that Jeff was taking the dissolution of his marriage far harder than Bill ever had his. Where Bill's self-esteem had been severely dented in the wake of the break-up of his marriage, Jeff's sense of self-worth took a serious nose-dive, quickly plummeting to a point where it was for all practically purposes nonexistent.

In an effort to help his friend, Bill tried everything he could think of and then some to bolster Jeff's spirits. But try as he might, nothing Bill did seemed to work. Jeff stolidly remained a morose shell of his former self. Basically, Jeff became an automaton, going through the motions of living without allow himself any of the enjoyment that life bestows along the way.

As the weeks stretched into months, without any appreciable sign of Jeff beginning to claw his way out the doldrums that he wallowed in, Bill began to become increasingly concerned. While Bill did not think that his friend was in any way suicidal, he truly believed that a crisis was on the horizon, and that if Jeff did not snap out of his depression soon, something drastic would happened.

The heels had been Bill's salvation. That led Bill to speculate that they might just prove to be Jeff's as well.

As perverted as it was, Bill enjoyed spending time as a woman far too much to ever consider the notion of lending Jeff the heels. That was not an option. Bill was not about to part with those magical high heels of his even for a day, much less the months that it would take his friend to fully recover. Besides, lurking in the back of Bill's mind was the sneaky suspicion that those magical high heels of his would not work for Jeff the way they did for him. And Bill was right. Though he was completely unaware of it, the heels had formed a metaphysical bond him and owing to that, they would not work their magic on anyone else but him. Added to that was the fact that while Bill enjoyed spending time as a woman, it did not follow that Jeff would too.

Having taken all that into consideration, Bill came up with another idea. Reasoning that the quickest way to bolster Jeff's self-esteem was if a new woman were to enter Jeff's life. While it was true that Bill could arrange a date for Jeff with any one of several of the single women he knew, given his friend's present state of mind, doing so would be risky at best. When it came to the dating scene, Jeff was his own worst enemy, your quintessential accident waiting to happen. It would take a magical night, or a very special kind of woman to deal with someone as morose as Jeff tended to be. It did not take a rocket scientist to realize that it was just too risky to try to arrange a date for Jeff. Bill knew all to well that a bad experience at this stage of the game could well prove to be disastrous. It might even push Jeff right over the edge and send him into an emotional tailspin.

However, Bill knew that he did not need to set Jeff up with a date with any of the women he knew. While he in no way relished the idea, Bill was aware of the fact that he could use those heels of his to actually function as Jeff's date. In that way Bill could negate pretty much all the risk factors involved in such an undertaking in one fell swoop.

That left Bill with only one major problem. He had to come up with a cleaver way of hooking Jeff up on a date with his own feminine alter ego.

 

Chapter 2

 

Bill pondered the matter of how he could go about arranging a chance meeting between himself, in the beguiling guise of his feminine alter ego, Sara Keep and his best friend Jeff Whitehall for several days before he finally hit upon a scheme that had a chance of working. However, before Bill could put his plan into motion he had several purchases to make.

For a good while their Bill had it in the back of his mind to purchase a used car to tool around in when he was out operating as Sara. His rather harebrained scheme to help Jeff out of depression gave him the impetus do just that. Though it cost him a little more than he wished to pay, having always wanted to own one, Bill purchased a used MGB that was in mint condition from a friend of friend of a guy he used to work with. Thankfully the heels' inherent magical wherewithal would insure that the car's registration would dovetail itself to Bill's current sexual orientation. That is to say that if he functioned as Sara, the MG's registration would identify Sara Keep as the car's owner. Likewise, if Bill drove the car as himself, the car's registration would identify him as the car's owner.

The second item Bill acquired was a cell phone. If everything worked out as planned, Sara would end up giving her number to Jeff. It just would not do for that number to be the same as Bill's home phone, a number that Jeff would have surely noticed. The cell phone would suffice quite nicely.

The last of Sara's purchases encompassed several related items. The first of those was a woman's bathing suit, which was rather ironic for it was the first piece of feminine attire that Sara had ever had the need to buy for herself.

Prior to that, if Sara wanted to adorn that absolutely scrumptious body of hers in something that tickled that lecherous male fancy of hers, all she had to do was to close her eyes and picture herself wearing such provocative attire in her mind's eye. Those marvelous high heels would dutifully belly up to the bar and - Whalla! - upon opening her eyes that would be the outfit that Sara what she would find herself stunningly decked out in.

The reason why Sara found it necessary to purchase a bathing suit for herself was do to the fact that she planned to somehow nonchalantly engage Jeff in a casual conversation while the two of them were at the Y swimming laps. Though Sara had as yet figured out exactly how she was going to go about it, her hope was that once she engaged Jeff in a conversation, he would take the bait and follow up by asking her out on a date. Basically, unsure as to how she was going to actually go about it, Sara figured that she would just have to play it by ear and hope that an appropriate opportunity would present itself.

Back to Sara's last group of purchases. Along with a woman's basic black nylon/lycra tank suit, Sara prudently picked up a bathing cap, swim goggles, a pair of flip-flops, two extra fluffy towels and a distinctly woman's styled pink and white gym bag.

Making an early day of it on that Tuesday, the day on which he was to put his plan into play, an anxious Bill arrived home around three-thirty in the afternoon. As soon as he got in this house, Bill called Jeff's home and left a message on his friend's voice-mail confirming the fact that while he might be a little late, baring any unforeseen consequences he would hook up with Jeff at Y sometime that evening. Aware that if his plan was going to work, he had to build up enough Residual Girl Time to cover the time he would be spending devoid of the heels while swimming laps at the Y's pool, Bill prudently donned the heels. Having done that, he kicked back and began to relish the phenomenal sensual rush that went hand in hand with his fluid transformation into a bonafide member of the opposite sex. Once she was fully female, Sara stripped off her clothes as a prelude to getting down to the business of indulging those narcissistic needs of hers.

Owing to all the anxiety she was feeling Sara arrived at the Y about a half an hour earlier than normal. Though she had been using women's public restrooms without giving it a second thought for several years, it was a novel and somewhat unnerving experience using the ladies' locker room in order to change into her bathing suit. She felt oddly conspicuous and though she tried to keep her eyes averted, Sara found herself hard pressed not to stare. Then, unnerving her all the more, was the dread she felt when she came face to face with the notion that she would have to leave her heels in the locker along with all her other clothes. While it was true that she had secured the locker in which she had stashed her stuff with a combination lock, it still troubled her greatly to be separated from those marvelous high heels of hers. Sara would never forgive herself if someone broke into her locker and absconded with them. In fact, Sara had half a mind to go back and get them; thinking that she could put them in her gym bag and take them out on the pool deck with her so that she could keep an eye on them while she swam. But if she did that, the risk of having someone steal them was greatly increased. So, even though she was still uncomfortable with the idea of leaving them in her locker along with all her other possessions, Sara, telling herself that she was being a real ninny about those heels of hers, decided in the end to do the prudent thing and leave them right where they were.

The clock mounted on the pool's far wall showed that the Y's swimming team had the exclusive use of the pool for another fifteen minutes. That being the case, Sara parked that succulent tush of hers on one of the benches that where parceled out around the pool's deck. Then, in an effort on her part to get her mind off the problems revolving around just how she would actually go about striking up a conversation with Jeff, Sara endeavored to focus her attention on a scuba class that was in the process of setting up their diving systems. Having been cajoled by Jeff into taking the very same class several years before as Bill, given some of the uncertainty that some of the students displayed while attempting to assemble their equipment, Sara assumed that this must either be their second or third pool session. Needless to say that Sara had to chuckle at seeing some of the ineptness that some of the student divers displayed. David, their instructor, the very same instructor who Sara had certified through, still appeared to have the patience of a saint. Sara could not help but marvel at how he casually pointed out what corrections needed to made, all the while good-naturedly grumbling that he would not be nearly as torrent in the future.

Swimming practice was finally over and the lifeguard on duty made the announcement that lanes one through six were open for swimming laps. The lifeguard then proceeded on to announce that lanes seven and eight were off limits due to the fact that the scuba class would be using those two lanes.

Jeff had as yet to put in an appearance. Sara, hoping that he would be there soon, decided that under the circumstance the best thing she could do was to avail herself of the pool and burn off some of her nervousness by swimming a few laps. As she headed for the pool's deep end, Sara began to fumble with the bathing cap she had purchased for herself. 'Damn! She mentally fumed as she struggled to cram that long blonde hair of hers up inside of it. 'I guess I'm going to have to add bathing caps to the list of things that I hate about being a woman. Besides, I think it's a stupid policy. I don't know why the Y insists that women wear bathing caps while the men don't have to...'

Owing to the fact that as yet no one was swimming in lane four, Sara decided that that was the lane she would at start off using. Entering the water with a well executed racing dive, Sara, who as Bill had been a competitive swimmer back in her high school days, set a fairly brisk pace for herself as she began to swim the eight laps that comprise the two hundred yard individual medley that had once been her forte. Completing the eight demanding laps in something less than three minutes, Sara was rather pleased with herself. Pulling her goggles down around that aristocratic neck of hers, Sara scanned first the pool and then the deck area hoping that Jeff had put in an appearance. Unfortunately, Jeff was still a no-show. Though disappointed, Sara, knowing that it was still early, decided that the best thing she could do was to swim some more laps.

And that's just what Sara did. However, instead of swimming another two hundred IM as she normally would have had she been there in the guise of her male alter ego, Sara opted to swim the eight laps using the breaststroke. That way every time she lifted her head to take a breath, she could make a quick scan for Jeff.

'Damn it!' a perturbed Sara fumed as she pushed off to begin another eight laps, electing to use sidestroke which, like the breaststroke, would allow her to survey the both the pool and the adjacent deck area while she swam. 'Where the hell is he? "I mean, here I go to all this trouble, and it'll be just my luck that he'll be no-show...'

Just then, just as she was about to expound upon that internalized tirade of hers, Sara, who was looking towards the door to the men's locker room and not looking where she was going, collided with another swimmer. Believing that she was at fault for the collision, a startled Sara was quick to offer an apology, "I'm sorry. I didn't mean to bump into you like that? Are you okay? I mean, I didn't hurt you did I?"

With a gurgle and a cough, the guy Sara had collided with sputtered, "Oh, you needn't worry about me." I'm fine." The other swimmer offered Sara a confession all his own. "Sorry miss. I'm afraid I was paying too much attention either. You see, I was keeping an eye out for a friend and I'm afraid that I wasn't watching where I was going. I promise, I'll try not to let that happen again." And with that said, the fellow turned and began strenuously stroking toward the pool's swallow end.

It was only then that a rather befuddled and flabbergasted Sara became cognizant of the fact that the guy she had just collided with had been none other than her friend, Jeffery Whitehall. 'Damn!' she mentally castigated herself for her ineptness. 'Why didn't you do something? I mean, he was right there! It was the perfect opportunity for you to saying something! But did you? Nooo! You, like a big ninny, let him slip right out of your hands. Now, what are you going to do girl? Act like a real klutz and run into him again...'

Not wishing to come off as some clumsy buffoon, Sara shelved the idea of bumping into Jeff again for the time being. However, she did not discount it out of hand. She told herself that if nothing else came to mind as a means to strike up a conversation with Jeff, she would use that tactic as a last resort.

For the next half an hour, as the two continually pass one another in the lane, Sara seesawed back and forth; sometimes castigating herself for flubbing an opportunity, while at other times wracking her brain to figure out an alternative means to strike up a conversation with Jeff. At a loss to come up with any imaginative ploy, an exasperated and desperate Sara resorted to prayer. 'Please God! Help me come up with a ploy that will allow me to strike up a conversation with Jeff.'

A few Moments later, as if in answer to her prayer, something most unexpected happened. As Sara pushed off from wall of the pool's deep end, the calf muscles of her left leg knotted to form an extremely painful cramp. Being an excellent swimmer, Sara was never in any real danger. She could have easily extricated herself from the pool. But coming unexpected as it had, the cramp served to arrest her forward progress while at the same time causing her to lose composure and begin noticeable flail about it the water. Jeff, who had been keeping an eye on the shapely young lady with whom he shared a lane with, took note of Sara's predicament and gallantly moved in to lend a hand.

Reaching Sara side, Bill adroitly slipped his hand into her armpit as a means to support her before calmly inquiring, "Leg cramp?"

"Yes." Sara, with a sputtering cough, dutifully replied as she felt herself being gently steered back to the wall of the pool's deep end.

Before Sara could adequately get her mind around what was happening, Jeff had hefted her out of the pool and had begun to skillfully massage the calf of that ever so tantalizing left leg of hers.

Then, even as Sara was trying to grapple with the unexpected turn of events, she heard Jeff ask, "Bad one, huh?

"Yes," she awkwardly replied. "It hurts like hell."

"I'll bet." Jeff continued to knead Sara's knotted calf. "Is this helping at all?"

"Oh, yeah," Sara honestly replied. "It's helping a lot..."

Though their conversation stumbled and stuttered-stepped a bit at first, it was Jeff who managed to get past the initially awkwardness they were both experiencing. And he did so by merely pointing out the fact that he had never seen Sara at the Y before. To wit Sara replied that she had just joined the Y and that this was the first time she had opted to use the pool.

With the ice broken, Sara employed those feminine wiles of hers to keep the conversation leapfrogging from one subject to another while Jeff dutifully continued to massage her knotted calf muscles. Oddly enough, the two of them became so engrossed in the conversation they were having that they lost track of time, to the point that they were both rather taken aback when the lifeguard blew her whistle and announced that the pool would be closing in another ten minutes. Having as yet to achieve the goal that she had set out to achieve, with that goal being to provide Jeff with her newly acquired cell phone's number with the hope being that he would take the hint and ask her out on a date, Sara seized the moment. Saying that she would really like to repay him for so gallantry coming to her aid, Sara insisted that the two of them go somewhere so that she could buy him a cup of coffee or soda or something. Nothing could have pleased Jeff more and so he readily accepted.

Jeff, according himself as a true gentleman, nimbly helped Sara to her feet. Having done so, he then proceeded to escort the hobbling Sara over to the entrance to the women's locker room. Saying that he would hook-up with her in the lobby, Jeff turned about and headed off for the men's locker room.

As before, Sara found the experience of showering and changing back into her street clothes to be a real eye opener. While none of the other women in the locker room could hold a candle to her in the looks department, there was no getting around the fact that there were several pieces of eye-candy that Sara found to quite attractive, there by sending that male libido of hers into overdrive. 'Damn!' she thought as she surreptitiously eyed a stunning brunette up one side and down the other. 'What I wouldn't give to slide that dipstick of mine up inside that tight little crankcase of hers. I mean to tell you, that is one fine piece of ass if ever there was one...'

Interesting enough, as Sara slid her feet into the inviting maw of those magical high heels of hers, the residual muscle aches of the cramp disappeared. Just like that they were gone. One second there were there and the next, they were gone. But that was to be expected. No matter what aches and pains Bill had as a guy, they always went away immediately upon his becoming Sara. Even scars disappeared, never to return, even upon his transition back into manhood. It was a nice little phenomenon. And need to say that it was one that Bill both cherished and appreciated

"I see your leg's doing a lot better," Jeff beamed as Sara briskly sashayed into the lobby with those high heels of hers clicking and a clacking.

With a bright and inviting smile affixed upon her face, Sara pleasantly replied, "Yes. Yes, it is. It's doing a lot better." Then, having said that and knowing fully well that there was a Denny's just down the street, Sara continued on to coquettishly inquire, "Now, how 'bout that cup coffee? Oh, and since I new in town, Jeff, I don't suppose have any suggestions as to where we might go to get one?"

Sara, seated behind the wheel of her MGB, followed Jeff to Denny's. Once seated in a booth, they started off by ordering a cup of coffee apiece. However, before they had finished that first cup, Jeff, saying that he was famished as an excuse to extend their time together, suggested that they might as well just go ahead and order something to eat; saying that it would be his treat. Sara readily agreed, but only on the understanding that the meal was on her. In the end, after a quick perusal of the menu, they both ended up ordering a Meat Lovers Special from the breakfast portion of the menu.

As they ate, Sara very tactfully got Jeff to talk about himself. Though she had heard it all many times before, to the point of ad nauseam, Sara patiently and tactfully drew him out and managed to keep him talking about himself. With a sympathetic ear she attentively listened as Jeff talked about his wife's leaving and the subsequent and as yet unresolved dissolution of his marriage.

Then, after the better part of an hour, it was Sara's turn in the proverbial witness chair. Jeff, who was smiling all over himself, wanted to know everything he could about her. Sara, who had come prepared with a bogus cover story, was more than happy to comply. Though she provided Jeff with many frivolous details about her supposed life prior to relocating there, Sara made sure to include some extremely pertinent, though fraudulent, details that she hoped would make life a lot easier for her if Jeff took the bait and asked her out.

Sara told Jeff that while she would be looking for a place of her own eventually, for the time being she was staying at a college friend's apartment. Then, having said that, she proceed on to explain that staying at her friend's place was not the best of situations; owing to the fact that this so called friend of hers had been raped during her senior year and because she had, she had this thing about men. Succinctly put, Sara drove home the salient point that her friend was terrified of men and therefore did not allow men to enter her apartment for any reason whatsoever. Men were strictly verboten, adding another important point that her friend was so paranoid that she became extremely upset whenever she answered the phone only to hear a man's voice on the other end of the line. Though Sara admitted that she had always planned on getting one, it was her friend's paranoia that had been the prime reason behind her purchasing a cell phone.

Sara's mere mentioning of her cell phone was all the impetus that Jeff needed to ask Sara if he could have her number. Flashing an endearing smile, Sara teasingly informed Jeff that she was wondering when he was going to get around to asking her for it; adding that he had not asked she would have taken the bull by the horns and given it to him for they parted company.

Unable to believe his good fortune, a besotted and therefore tongue-tied Jeff continued on to gingerly inquire if Sara might do him the honor of going out on a date with him either that Friday or Saturday. Saying that she had been hoping all along that he would ask her, Sara readily accepted; suggesting that Jeff call her the next evening so they could work out the details. Then Sara surprised herself by insinuating that if their date on Friday worked out as she fully suspected it would, given to how much they seem to have in common, she might be opened to spending a good deal more of the weekend in Jeff's company.

A little after twelve, Jeff, over Sara repeated protests, left a tip and paid the bill for their meals. He then walked Sara out to her car and though he had not planned to do so, he stepped in and kissed her full on the lips. It was not a long or what one might term a passionate kiss, but it was a kiss all the same. Needless to say, coming unexpected as it was, the kiss threw Sara for a loop. A guy, who was none other than her best friend, had haul off and kissed her full on the lips, sending her mind, or more specifically that staunchly male ego of hers into convulsions of the most repugnant and repulsive kind. Though the kiss had shocked the living shit out of her, to Sara's credit, she did not flinch. As shocked as she was, Sara just stood there and took it like the man she no longer could claim to be. Then, fearing that she make have come off a little frigid, which in turn might have sent Jeff the wrong sort message, Sara in a frenzied, Chinese Fire Drill sort of way, sought to repair any damage she might have engendered. She kissed him back, save that where Jeff's kiss had been soft and tender, hers was hard and passionate.

"Holy shit!" a much-befuddled and thoroughly perturbed Sara murmured to herself as she pulled out of Denny's parking lot. "What the shit have you gotten yourself into, girl? What in God's Name ever possessed you to haul off and kiss him like that? You know that you were supposed to take it slow. Actually, you were supposed to take it slower than slow. Now what are you going to do? I mean, you know as well as I do what kind of a message a kiss like that sends..."

 

Chapter 3

 

The next day, with the next day being Wednesday, Bill called Jeff shortly after six in the evening so as to clear the decks for his feminine alter ego to put in an appearance. The first thing Bill did was to apologize for being a no-show at the Y. Feeling none to good about having to lie to his friend, Bill made the bogus excuse that he had a flat tire and that by the time he got it changed he was far too grimy to head over to the pool. Jeff, aware that unexpected things happen, accepted Bill's explanation at face value. Then, once that subject was out of the way, a very upbeat Jeff jubilantly told Bill about the drop-dead gorgeous girl he had met while swimming laps at the Y. With a renewed sense of confidence conveyed in the timbre of his voice, an ecstatic Jeff proceeded on to tell Bill about Denny's and how he had gotten up the gumption to make a date with the very same blue eyed blonde bombshell. Though Bill was eager to get off the phone and don those magical high heels of his, he chided himself to be patient and to listen attentively as Jeff enthusiastically gave him a rundown on that new lady-friend of his and what the two of them had talked about.

As their conversation was winding down, Bill prudently took the initiative to stem off a potential problem. Knowing fully well that Jeff might try and call Sara immediately upon the termination of their conversation, Bill, who would needed a few minutes to change into Sara, suggested that it might be better for Jeff to wait until at least seven thirty to place the call. Then, when Jeff indignantly asked him as to why he might want to go that route, Bill replied that if Jeff were to call to early it might make him appear anxious and therefore needed. "Come on, pal," Bill good naturally chided. "I know you like this girl. But take my word. The last thing you want to do right now is come off as being too eager. In other words, don't crowd her..."

Hoping that he had gotten through to his friend, Bill hung up the phone's receiver and immediately slipped his feet into the awaiting throat of those magical high heels of his. As always, the erotic rush that went hand and hand with his transformation into a member of the fairer sex engulfed him, sending Bill's horniness quotient skyrocketing through the roof in the process. A few minutes later, with that staunchly male libido of hers spurring her on, Sara, who's head, arms and hands were still those of a man, was busily using the middle finger of her right hand to aggressively caress the elusive and ever so sensitive nub of that new clit of hers. A few minutes later, a fully transformed Sara climaxed and shortly thereafter entered the serene and self-indulgent mental state of the warm-fuzzes of post-orgasmic splendor.

Knowing Jeff as she dad, Sara was dubious that he would heed the advice that she had given him as Bill. Feeling like he would call at any minute, Sara, who found herself as anxious as Jeff had seemed during their phone conversation, decided to make herself as comfortable as possible. While it was true that the clothing that she had been wearing as Bill had transformed into comparable female attire in conjunction with the transsexualization that her heels had engendered, Sara did not feel that the outfit lent itself to an evening of lounging around the house. While the charcoal slacks and white fisherman knit turtleneck sweater she was wearing did indeed flattered that hourglass figure of hers, Sara opted to adorn herself in something that was both sexy and comfortable, all at the same time. Though she was half tempted to adorn herself in scanty and provocative harem girl attire as she did every now and again, Sara thought better of it. Forming a mental picture of something a little less ostentatious in the crucible of her mind's eye, Sara blinked and - Whalla! - she found herself attired in a pair of slinky black nylon/lycra running tights, a shimmering pale blue satin sleep shirt and of course those magical stiletto heels of hers.

Feeling a lot more comfortable, but no less nervous, Sara strode into the kitchen and got herself a can of soda out of the refrigerator. Returning to the living room, she plopped down on the sofa, placed the can of soda on the end table alongside of her cell phone and then turned on the television. Hoping that she could find something interesting to watch in the interim, an anxious and apprehensive Sara began flipping through the channels. Though she had seen the program that was on the History Channel twice before, given that nothing else had grabbed her interest, Sara, who did enjoy watching shows about World War II, ended up electing to watch it for a third time.

As expected, Jeff did not heed Bill's advice. Though he knew his friend's advice was sound, Jeff just could not wait till seven thirty to call Sara. However, to his credit, he did hold off until quarter after to seven to place the call.

Ironically, Jeff's call was the very first time that Sara's cell phone rang. And when it did ring, it startled the living shit out of Sara, causing her to fumble and drop it, not once mind you, but twice, before she finally managed to pry it open and push the button to answer it.

Though their conversation was awkward and stilted at first, once they got past the preliminaries of shoring up the date and discussing the various options that Jeff presented Sara with, their shared sense of nervousness dissipated. Within the first few minutes Sara and Jeff's conversation quickly reverted back to the ease and free flowing exchange that they had enjoyed on Tuesday. The two of them prattled about anything and everything as they gleefully leaped from one topic to another.

Though Sara was not at all happy over the fact that she had to lie that pert and perky ass of hers off in order to feed Jeff a lot of bull about her past, Sara consoled herself that she was doing so for a greater good. Granted, Sara had to continually watch her P's and Q's least she misspeak herself and there by divulge the fact that she had insider information that by rights she should not have had. But even though she did have to watch what she said, Sara nonetheless found herself really enjoying the conversation she was having with her friend. Jeff was a great guy and their conversation only served to reinforce Sara's rather laudable opinion of him. She also found herself both heartened and more than a little flattered whenever Jeff made mention of his best friend Bill and how great a guy Bill was.

All in all, the two of them talked for a grand total of a little over four hours. It was almost eleven thirty when they finally bid one another goodnight and concluded their conversation.

Sara went to bed that night elated, feeling as though she had done a good thing. Jeff, she truly believe, had turned the corner. Thanks to Sara, Jeff had his self-esteem back and he was anything but depressed. He now had something to look forward to. Sara had given Jeff the gift of herself, leaving Sara with just one question to ponder. Just how much of herself was she willing to give? Friendship was one thing. Virginity was something else altogether.

Technically speaking, Sara was not a virgin. That is to say that her hymen was no longer intact. Shortly after coming into the possession of the heels, one evening while vigorous finger-fucking herself in an effort to see what worked and what did not, she had inadvertently gone and popped her own cherry.

Sara was not at all sure that she would be able to go to the extreme of allowing Jeff to make love to her. In fact, she was adamant that she would never allow things to get that far. Sara figured that more than likely she would probably have to let him get to first base. In a pinch, she might even have to bite the bullet and allow him get to second base. But that would be the be all and end all of it. There was no way that Sara was going to let Jeff get to third base, much less steal home.

After all, while Sara was all girl in a purely physically sense, her mind was as manly attuned as if ever was. The mere idea of having a guy's gnarled up 'thing' rammed up inside of her was an anathema. The very thought of being on the receiving end of things made her stomach retch.

While it was true that Bill enjoyed spending a get deal of his time as an anatomical correct female, Bill did not have a homosexual bone in his body. He was as heterosexual as heterosexual could be. Sara was another matter all together. When Bill functioned in the guise of his feminine alter ego Sara, only then would he as a she find herself classified as a homosexual. Be he male or female at any given moment in time, there was one constant in Bill's life, with that constant being that he was attracted to women.

 

Chapter 4

 

While the question surrounding how far he would go to bolster his friend sense of self-worth troubled Bill every now and again throughout the day that Thursday, he really began to worry about consequences of what he had embarked on later that evening.

Every Thursday evening Bill and Jeff hooked up with a group of guys they had paled around with since high school to play volleyball. After a couple hours of volleyball, the whole group of them would head over to an Irish flavored pub to down some brewskies and just shoot the shit with one another. It was there that Bill realized that in his attempt to help Jeff out of the doldrums that he wallowed in, Bill might have gotten in way over his head.

As soon as Bill bellied up to the bar, Jeff sidled up to him, seeking some friendly advice. Having been out of the dating scene for quite a few years, Jeff sought his friend's counsel on the sexual aspects of dating, specifically as to how fast or slow he should try to move things along.

Needless to say, Bill was taken aback by his friend's rather pointed questions. Though he found the whole conversation unsettling, Bill managed to somehow retain the presence of mind to hide the fact that his friend's questions had unnerved him. Then, just as he was on the verge of offering his friend a half-baked replied, Bill realized that Jeff's questions were nothing more than a blessing in disguise. "Well..." Bill began his reply thoughtfully. "If I were you, I'd take it slow. In fact, I'd take it real slow. You know, like some in the order of a snail's pace. I mean, the last thing you want to do right now is to come on too strong. Do that and you might just frighten her off. Word to the wise. Don't rush things. Take your time. Look Jeff, if you really like this girl, which it sounds to me like you do, my suggestion is that you work on building a good solid relationship first. Then, after you've got a good solid relationship going, the two of you can begin to explore the sexual aspects of the relationship."

"Yeah," Jeff reluctantly concurred. "You're probably right. I guess the best thing for me to do is to kind take my cues from her."

Thinking that he might be out of the woods so to speak, Bill readily agreed, "Yeah, that's exactly what I would do if I were you."

"Yeah..." an anything but jubilant, Jeff thoughtfully speculated. "You're right. That's probably the best approach for me to take. But then again, considering all the intimate stuff we talked about last night, not to mention the way Sara hauled off and kissed me in Denny's parking lot, I'm not all that sure that she wants me to take it slow. I mean to tell you. That kiss of hers was pretty spectacular, to say the least..."

Bill knew at that moment that he, in the guise of his feminine alter ego, had royally screwed up on Tuesday. 'Damn it!' Bill mentally chided himself. 'What in the hell have you gotten yourself into now?' Then, borrowing a euphemism that a young cousin of his liked to use, Bill continued to mentally berate himself. 'You big dummy dunderhead! Thanks to you and that impulsive kiss of yours, your friend here not only wants to get into your panties, but he also thinks that's what Sara wants as well.'

"Hey!" Jeff irately demanded. "Are you listening to me? Have you heard anything I've been saying? I mean, here I am, asking for your advice and from the looks of things you haven't heard a thing of what I've been saying."

"I'm sorry pal." Bill, aware that he was a guilty as charged, offered his friend an apology. "I didn't mean for my mind to wander off like that. The problem is that I've just had a lot on my plate here lately." Then, in a vain attempt to reinforce his early suggestion, Bill hammered home the point he had endeavor to make before, "Look man, I don't know what to tell you, save to say that I really think you ought to take it slow, at least for the time being.

"Yeah, but what happens if she doesn't want me to take it slow?"

Thinking fast, Bill replied with the first thing that came to mind. "Well, in that case, I were you, I'd use the First Headache Approach."

"Huh?" Jeff apparently had never heard of the First Headache Approach. "First headache? What the hell are you talking about?"

Having mentally castigated himself up one side and down the other for the slip-up, Bill replied, "Oh, it's just something a Marine buddy of mine told me about. And let me tell you. I've tried it and it works like a charm. In fact, it works so well that I pretty much use it whenever I start dating somebody new."

With his curiosity peeked, Jeff countered, "Okay! I'll bite. Go ahead. Explain how this First Headache Approach of yours works."

Though he was none too happy about it, knowing fully well that he was digging himself in even deeper than he already had, Bill began to fill Jeff in on how the First Headache Approach worked. Prefacing his explanation by emphatically stating if the First Headache Approach is to work, that the guy never broaches the subject of sex. The girl has to initiate the subject of their going to bed together. She has to take the lead and do all the asking. Otherwise, the First Headache Approach will not work. The guy only gets one chance at using the approach. And because he does, he has to get it right the first time.

Once the girl broaches the subject, clearly suggesting that the two of them engage in sexual intercourse, as much as the man might want to accede to his date's request to hop in the sack and have his way with her, he has to differ. However in doing so, the guys has to say something to the affect of that while he can think of nothing he would rather do than to make love to her, he has to say that he thinks it might be for the best if they both waited. Then, when the girl demands an explanation, and there is little doubt that she will not demand one, the guy has to lay it on thick, heavily emphasizing the fact that he really likes her. He might even go so far as to insinuate that he is well on the way to falling in love with her. However, having said that, the guy has to impress upon the young lady that he does not want to do something that might jeopardizing the relationship the two of them are in the process of building. Basically, the guys has to tell his date that come morning, he dose not want her to in any way regret her decision of going to bed with him. Then, having said something to that affect, the guy needs to suggest that his date take some time to really think about her decision as to whether or not she really wants to take the next step and make love.

Without saying anything, by the mere act of informing his date that he wants her to be sure that she really wants to have sex with him, the guy has established a couple of things. On the one hand, the guy has established the fact that he really likes her and would love to go to bed with her. And on the other, without him ever having to actually come right out and say it, he has demonstrated the fact that he respects the shit out of her, gaining for himself a lot of Brownie Points in the process. Basically, the guy has created a win/win situation for himself.

Generally at that point in the proceedings, the girl, thinking that she has hooked herself a keeper, will begin to press the issue and do everything she can think of to entice the guy into going to bed with her like right then and there. Bluntly put, she is not about to let such a great catch get away. She means to set the hook and she plans to use sex as the way to accomplish it.

But the guy has another card to play before the two of them head for the bedroom. When she starts begging him to go to bed with her, he agrees on one condition, with that condition being that she abides to the tenets of the Three Times Rule. He explains that if the two of them are going to go to bed together, she has to promise him that they will do it at least three times. Having said that, the guy goes on to explain the logic behind why he wants her to promise to go to bed with him on three separate occasions. Prefacing his comments with the notion that everybody can have a bad night in the performance department, due to nerves, awkwardness or just being tired, or any number of other valid reasons, the Three Times Rules provides a sort of safeguard, or insurance if you will. One person might have an off-night on one occasion, while the other person might have an off-night on another, but if the two of them experience three bad nights in a row, then maybe they ought to reconsider their options. Granted, even after three bad nights in a row, they can always elect to keep trying to see if they can get it right. But if one or the other wants to call it quits, they can do so knowing that they gave it a fair shot.

Thinking that his friend had to be pulling his leg, an incredulous Jeff sought Bill's reassurance. "You're kidding me, right?"

"No! I'm not kidding you at all, pal. Look, I know how crazy it all sounds. But, as God is my witness, I have never failed using the First Headache Approach. In fact, I've gotten laid every single time I've used it."

"You're shittin' me, right?"

"No! I'm not shittin' you at all. The First Headache Approach works likes a charm just as long as make sure that you use the Three Times Rule in conjunction with it..."

 

+

 

 

As Bill climbed in behind the wheel of his pickup, he began to verbally castigate himself. "You know something, pal? You really are an asshole. Thanks to you and that stupid kiss of yours, your friend wants to fuck your brains out. Just what in the hell were you thinking?" Then, in answer to his own question, a thoroughly disgruntle and self-deprecating Bill despondently quipped, "The problem is you weren't thinking. Had you been, you never would have done something that outrageous. I mean, that kiss of yours had 'fuck me' written all over it..."

Bill knew exactly what the problem was. He had spent far to much time planning the logistics of how to go about hooking his friend up with his feminine alter ego while never giving any thought to the both the advisability and the repercussions of hooking Jeff up with Sara. Bill did not blame Jeff one iota for wanting to go to bed Sara. Hell, if Bill had met a girl who looked as terrific as Sara did, he had to concede the fact that he would have been chomping at the bit to have his way with her. Jeff was not the problem. Bill knew perfectly well that he had been the problem. He had let his vagina do the thinking for him and not that manly attuned brain of his. He had started something without giving any thought as to how he would ever finish it.

And there was an even bigger problem. If Sara were to suddenly break off the relationship it could send Jeff reeling and plunge him right back into the Pit of Despair that he had been wallowing in for far to long.

Bill was in a quandary as to what he should do.

 

(continued)

  

  

  

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