Training Philip Pt. 01

Chapter One

- Realization-

Alison had owned and ran the oversized clothing and footwear shop on the corner of South Main and Dixon streets for nearly twenty years, and the business had continually improved. Alison and Phil lived just above the shop in a two-bedroom overhead apartment.

Her son Philip, whom she just called Phil, had recently been attending his final semester of college at the not-to-distant University that was reasonably nearby. Phil had just finished his schooling and majored in business and management and was soon to begin work there with her at the clothing shop. He was to take over and run the business entirely in time eventually.

After all the graduating procedures were complete, the two of them had planned to spend some time training him for the position he would fill soon enough.

Phil was already very familiar with the store and all the inner workings involved. He had spent much of his time there as a child until he reached high school and then not quite as much. So, it wasn't the business end of the job that Alison was concerned with when it came to Phil working there beside her at the shop.

But still, it was the footwear department that Alison was primarily concerned with when it came to Phil running things himself. The customers in the clothing department all pretty much cared for themselves, but the footwear section differed entirely.

Phil had always tended to get a little preoccupied with things around him sometimes, and it seemed he could not often pay close attention to detail, especially where it mattered and was most needed.

Alison had already attempted on more than one occasion to walk him through the complete process of providing the customers with a proper footwear fitting. But she seemed to be having difficulty getting him to fathom that you don't simply put a shoe on a customer's foot as much as you place their foot into the shoe.

"Big, big difference," she had to scold him repeatedly. "Not so much with a man, mind you," she said, "but with a woman, it was an absolute must that could not be overlooked, at the very least."

But her young son could not concentrate on what he was doing at almost any given time, and his eyes always seemed to wander across the room and be somewhere other than where they needed to be.

Alison knew she must come up with a solution soon if Phil was to overcome this hiccup and work alongside her at the family business, but she was utterly lost as to what she could do to help him with his situation.

It was a Sunday morning, and the shop would be closed for the day. Alison pulled on a light t-shirt, a pair of sweatpants, and flip-flops and quietly told herself this would be a good day and they would accomplish much. She slowly headed toward the kitchen for coffee and a little breakfast; there was no need to hurry as she knew she would have to wrangle Phil out of bed to get any use or cooperation out of him that day.

It seemed Phil wasn't much of a fan of weekend training. She generally didn't bother him very much on those days, but she was beginning to grow a little desperate as he would soon start the position in less than two weeks.

She had already recently lost an employee she had caught stealing from her, and the only other one than herself had also very recently given her a two-week notice, and this was to be her last week there as well.

Alison sat directly in front of Phil at the long-fitting bench in the footwear department located at the center of the building. She immediately noticed he seemed somewhat more alert and maybe even more focused as he carefully reached for a pair of heels and began cautiously putting her feet into them.

"What in the world had come over him," she suddenly wondered. She had certainly done nothing yet to change anything at this point; she was still utterly clueless about his whole problem and just how to go about possibly helping him resolve it. She was still merely guessing at solutions herself.

After a bit, Alison was reasonably satisfied with his performance so far for the time being, so they casually moved on to something else. Again, he seemed to be sharply focused on her every move, and he was right on point with everything she explained and showed him. He was completely different; she could not figure out why.

As the day drew on, she became even more impressed with this new attention span of his. She was purely amazed at the enormous change in his attitude and focus.

But she soon figured it all out a bit later when she got a phone call and had to run out suddenly for a brief spell. As she went to get dressed a little more appropriately for her short trip out and back, she gasped loudly at her image in the mirror as she suddenly understood it all completely.

Without a bra on beneath her thin white t-shirt, her stiff nipples and puffy pink areolas were rather somewhat visible as she stood there and glared shockingly at the reflection staring back at her. After a moment, she quickly slipped into a bra and some blue jeans, and out the door, she went.

As she quickly made her way to her destination, she could not shake the images of her prominent, robust nipples pressing tightly to the thin white material of her light t-shirt.

"So, that's what that was all about back there," she giggled slightly.

She thought she should have known immediately what was happening, as she was always dressed in her work clothing whenever training with Phil on weekdays.

She then giggled again, "Men, who could figure them," she mused.

As she finished her business and headed back, ideas of her young son looking at her tits suddenly began to slip up on her; she had not seen him staring at her boobs, but what other explanation could there be for his unexpectedly impressive behavior at her attempts at job training him. It seemed as if she had had his undivided attention for once; she snickered lightly to herself.

Alison was surprised that she suddenly realized she did not seem upset about it and maybe even somewhat flattered by it. She may even be beginning to feel a bit giddy over the whole situation as she felt butterflies suddenly churning slightly in her belly.

"Holy shit," Alison exclaimed as she pulled into the driveway, and what she had been subconsciously suspecting the last few miles suddenly seemed to become a reality for her. Since she had left her destination and began to travel back toward home, she had slowly appeared to be growing a bit moist down there, and now she realized this had all suddenly become a genuine thing.

"Oh my God!" she thought as she braked lightly and then slowly turned up into the drive; she was becoming sexually motivated over her very own sweet son ogling her soft, firm tits for a brief time, and she hadn't even fucking seen him do it. Not even once, not even at all!

Alison very soon decided that her feelings toward this whole strange yet stimulating situation were just a by-product of exactly how lonely and sexually frustrated she had become over her years of sexual isolation. Alison had always been too busy with the shop to date, and time had just seemed to slip away, inevitably leaving her alone there with just Philip for comfort and a shoulder to lean or cry on when needed.

Realizing all this, she quickly brushed it from her mind as nothing serious and attempted to salvage some of what was left of the day. They didn't get much accomplished, though, as Phil was right back to his old, distracted self, so she soon decided that tomorrow would be another day, and she just gave up for the time being.

Alison suddenly realized that she may have also seemed distracted after her short little trip out and back earlier in the day.

Monday morning, Alison opened the shop promptly at 8:30 am as always, and soon they were back at the training again, hard and heavy whenever they had a chance between the customers and such.

Phil was his usual unproductive self as she again tried to run him through a shoe fitting for both a man and a woman. He was just totally disinterested in it all, and it showed badly. After receiving no forward progress with him, she informed him they would work on it later that evening after business hours as the store was getting rather busy anyway, and it needed her undivided attention.

Later that evening, after closing down the shop and then having a relaxing shower, she stood at the big mirror dressing for their late-night training session. As Alison pulled the thin white t-shirt down over her perky bra-less breast again just as before, she softly told herself, "Sometimes a mother just has to do what a mother has to do to teach their children the important life lessons that they need in this harsh environment."

She understood completely that that was all just simply a crock of bullshit she had just come up with and was telling herself to make herself feel better about it all. But that's what she was telling herself by God, and that was all she had for the moment, so she was just going to run with that for the time being, damn it!

She was very aware that she had enjoyed entirely the thought of what she had suspected about Phil, and she knew it well, but she could never admit it to herself, not about her very own son like that. The idea was just way too significant, very taboo to her.

She could feel her tits gently sway back and forth beneath the thin white shirt as she made her way back to the shop to find Phil and began the process of verifying for sure if what she suspected of him was indeed fact or fiction.

The moment Phil's eyes locked onto her bobbing breast as she casually strolled toward him, she felt the warmth suddenly spread through her loins, and she instantly realized that she was already in big trouble with this whole crazy mess.

She suddenly realized it didn't make a difference if she learned anything about Phil's actions. She didn't necessarily need to know about him anymore as she had just discovered something shocking and disturbing about herself.

She hadn't put the little white t-shirt back on to test Phil's reaction to it. No, not at all; Alison had suddenly figured out that she had put the shirt back on because she had wanted her sweet young son Phil to check out her pert shapely mature titties again, just as soon as remotely possible even.

But with just one exception, it seemed. Alison did indeed want her son to check out her body again seriously, but she would be carefully paying attention and watching him in return this time as well.

Alison suddenly realized that her training of Phil was no longer just about his career benefit but had somehow turned into something threatening to expose her neglected needs. This was just insane, she thought, "Completely bonkers."

Things went as expected, and she always seemed to have Phil's undivided attention. He excelled with every issue or situation she confronted him with. Even in the footwear department, things seemed to go well.

She had watched him closely the entire time and was more than satisfied that her unrestricted breast beneath the thin white t-shirt was, after all, the culprit behind the significant change in his concentration.

As she sat watching him watch her tits bounce and jiggle around beneath the white t-shirt, she became pretty stimulated by his longing gaze. Towards the end, she casually noticed the ridged form of his hard dick in his pants and suddenly felt as if a change of her underwear may be in order soon enough now.

"Wow," she thought, as she turned out the lights in the shop, "If a simple shoe fitting could do this to her, she might just have to walk him through a brazier and pantie procedure sometime!" She laughed softly at her crude joke as she flipped the switch off.

It was no longer funny the following morning as she had awoken seriously considering the bizarre idea. "Why not?" she mused. To maybe have a little fun with him, that's all. A bit more excitement in her life surely couldn't hurt anything, could it? She was pretty positive that Phil would undoubtedly enjoy it immensely, himself. She could stop it all whenever she needed to, right? She carefully considered.

Maybe just a brief peek at her little panties now and then or a quick accidental flash of her perfectly ample breast swaying about before him on occasion, "Just some little harmless stuff," she speculated with a sly grin.

She considered maybe just wearing a looser-fitting shirt occasionally and maybe doing a lot more bending over in front of him or something along those lines. Perhaps a pair of short shorts or a short little skirt. Panties could be an option with either, she quickly deciphered.

Maybe she could let him catch her in some see-through lingerie for a quick show. Or perhaps a bit later, she could even get some tiny, see-through panties and wear them around him.

She suspected. Eventually, she could allow him some quick peeks at the soft blond pubic hair that should be protruding from around the edges of them. "Just something safe and nothing too dangerous." she studied.

She should probably take it very slowly, though at first," she softly warned herself.

"But it could and should be quite a bit of fun for the both of them if it were done correctly on her part," she suddenly decided. "Now, just how to go about gently getting the ball rolling," she began to give some serious thought to.

She decided that since the shop would be closed all next week for renovations, she should be able to spend most of her time thoroughly addressing the stimulating issue; she just had to figure out how to get it all started without bringing much attention to her wicked little sinful scheme.

Tomorrow should be an exciting day, she imagined, as she drifted off to sleep while gently caressing her stiff nipples and anticipating the start of this new little adventure, she was to begin in her life very shortly.

Chapter Two

-A Teasing-

When Alison pulled on a loose-fitting thin blouse with a low V-shaped neckline and big saggy arm openings, she wondered if going braless in such a revealing garment already was possibly pushing things too far a bit too fast.

Nonetheless, she quickly brushed it off and then slipped into a fresh pair of undies. While the shorts she slid on over them were not all that short, they were also very loose-fitting around the leg openings.

Alison knew if she sat just so and opened her legs just a tiny bit, Phil would indeed positively be able to view a little bit of her panties from time to time. Women knew these things about themselves; they always knew if you could see their bra or panties. It was somehow a seventh sense that they possessed.

After just a short time of bending way over in front of him again and again and on occasion raising her arms real high, Alison was quite sure Phil had ultimately viewed her titties in all of their glory, pink puffy areolas, big fat nipples, and all!

"Now for the panties," she eagerly thought, and then uncharacteristically took Phil by the hand tightly and quietly led him off to the footwear section.

His eyes were positively glued to the space between her open legs as she sat on the fitting bench directly before him. While he attempted as best as he could at the moment to put shoes on her feet, she slowly spread her legs apart, revealing the lacy edges of her light blue panties to him.

Later that night, as she lay in the dark on her big bed, she did something she had never come even close to considering before. Alison slipped her soft little hand down into her damp panties. She quietly pleasured herself to the thoughts of intentionally exposing her tits and panties to her very own son on a first-time occasion; suddenly, she trembled violently and deftly brought herself off very quickly all around her slick, slimy wet fingers as she relived his gaze between her open legs.

Alison had never masturbated to thoughts of Philip before, not of her very own son like that!

The next morning when her attire for the day consisted of a similar blouse thrown over her perky bra-less boobs again, but this time with a much shorter pair of shorts encasing her wide, shapely ass. Alison just knew that she for sure would again fall asleep later that night with her hand stuffed down her wet panties.

The day went well; she again intentionally exposed herself to him with a careful, cautious passion. Alison thoroughly scoped out Phil's hard dick beneath his thin shorts with every opportunity given to her. Her lust only grew severely as the day progressed. Later that evening, as she peeled her saturated panties down her long shapely legs to shower, she realized she wasn't going to be able to wait much longer to expose her complete pussy and full bush of light blond pubes to Phil; it seemed suddenly that she was pretty desperately dying for him to view her bare hairy crotch in its complete entirety already!

When Alison slipped into a short little skirt the following morning, she knew she was already upping the game considerably. Phil wasn't just about to get a quick glimpse of her panties, she thought. He was in for quite a treat if her legs were spread while she sat directly in front of him during a shoe fitting.

She wouldn't have to do a thing, she suddenly realized. He would spread her legs himself when he attempted to put her foot into a shoe. He could open them just as wide as he wished, and bam, her panty-clad crotch would be right there, staring him directly into his big, beautiful eyes.

Alison felt shivers run through her as she slipped on a short half-shirt that allowed the undersides of her boobs to show. She knew if she bent way over in front of Phil, the bottom of the short little shirt would fall up around her neck, and when she stood back up again, her perky tits would be out and standing at attention for him to view for a brief moment or two. Completely. She realized.

Late that evening, after her sinful day of festivities with Phil, Alison went to the lady's undergarment section before returning to the little apartment. She had shown Phil her pert, perky titties in their complete entirety several times and then some on that long hot day, so now for the next step, the only thing that he hadn't seen of her just yet.

Alison quickly procured the smallest pair of tiny black thongs in her size that was currently in stock and immediately available. A bit later that night, while thinking of what the next day was sure to bring her way, Alison excitedly masturbated twice before going to sleep that night.

She was planning to let Phil view a good bit of her bushy blond pleasure palace the following morning, and the thought of the devious action she had planned had her wet hairy cunt set ablaze, and it had been just totally burning up at that moment.

She had doused the flames considerably before dozing off, but Alison continued smoldering throughout the long, hot summer night.

When Alison sat down before Phil the following morning in another of her short skirts and loose-fitting blouses, she could tell that her son was again well pleased with her wardrobe choice for the long, hot summer day ahead.

When he reached for her foot and opened her legs slightly, Alison knew precisely what he must see of her. She had inspected herself very closely in the mirror before waking Phil and heading down to the shop just below.

She had seen how the little narrow strip of black cloth covering her sweet, moist quim left little to anyone's imagination as to what was beneath it. The thin strip of cloth had grown somewhat damp already from her excitement and had sunk up into Alison's hairy wet twat a good bit already.

She knew without looking down at herself that her blond pubic hair was completely obvious to each side of the little strip, and only her slick pink pussy lips seemed to be completely hidden from his view.

She watched his cock quickly proliferate and grow much larger beneath his shorts. Then she brought her eyes up to his and smiled cunningly at him as if to let him know that she was well aware that he was thoroughly inspecting her forbidden garden, which she had lain out before him intentionally for her son's viewing pleasure. And also, to let him know that she was immediately mindful of the effect it was having on his sweet young dick.