The Misadventures of Hillary Hagg Ch. 01

Part 1: Meet Hillary Hagg

Prom was only two weeks away and Hillary Hagg still didn’t have a date. The young woman couldn’t quite understand why as she stood before the mirror in one of the lady’s rooms of Benjamin Dover High. She was wearing the tightest jeans she could squeeze her chunky thighs into, teetered around on the highest pair of square-toed platform boots she could find… she had read in a fashion magazine that square toes made ones feet appear smaller and even purchased them two sizes too small to give the illusion of having normal sized feet.

Withdrawing a pair of socks from her gym bag, she drenched them in her favorite perfume (Poison) in an attempt to cover the pungent smell that infused them after having worn them in gym class just the period prior. After she was satisfied, Hillary then stuffed one sock each into her already overflowing bra. She’d stuffed so much toilet paper into the bra that morning there was barely enough room in the double-D sized bra for her own double-A size breasts. But Hillary was determined, if not particularly bright, and within minutes she had given herself the illusion of having more cleavage. The fake breasts even looked almost real if one ignored the lumpiness, and the way her left tit had a tendency to veer to the left.

The bell announcing the beginning of the next period rang, but Hillary didn’t care. She would only be missing English class, and getting a date for prom was far more important. Besides, she could speak English just fine, why did she need too study such a pointless subject?

By the time Hillary was finished stuffing her bra and touching up her make-up, the class period was just about to end. Hillary, pleased with her work, began to smile at herself in the mirror but stopped when she noticed that any facial movement caused the pancake make-up (which she used to cover up her freckles and give herself what she thought looked like a porcelain complexion) to crumble and flake off.

“Note to self,” she said aloud to no one in particular in her nasally high-pitched voice, “I just have to remember not to smile.” Hillary then spun about in front of the mirror. “Wow! I look hot!” she said aloud, again. From one of the stalls came a loud snort and Hillary jumped in surprise.

“Hello?” she called out. “Is someone there? Are you okay? You sound sick.”

Tabitha Pester, one of the school’s hardcore Goths sauntered out of the stall and looked down her nose at Hillary. “Well, I WAS fine.” The pale brunette flicked her cigarette butt to the floor and brushed past Hillary on her way to the door.

“Oh, Tabby,” Hillary mewled, feigning concern, “Is there anything I can do?” Hillary always did her best to ingratiate herself with Tabitha as she was terrified of the beautiful Goth. Tabitha did indeed cut an imposing figure with her long black hair and heavy, dramatic makeup. But Hillary had more reason than that to fear her. Tabitha had beaten her up in kindergarten and stuffed her into the play oven during playtime. It was an experience that still gave Hilary nightmares. And what was worse, the teacher had not punished Tabitha because she’d said that Hillary has deserved the treatment for not having had the manners to share the Lego’s when Tabitha demanded them.

“Don’t call me, Tab-“ Tabitha stopped mid-sentence and sniffed, turning slightly green when the stench of the sickeningly sweet perfume and sweaty gym socks hit her. She pressed her face against the leather sleeve of her jacket. “What is that perfume you’re wearing? Malithon?” She backed away toward the bathroom door.

Hillary smiled. “Oh no, it’s Poison.”

“I believe it,” mumbled Tabitha pulling open the door and gulping down the fresh air.

“Thanks!” Hillary called after her, then gathered her own things and departed the bathroom just as the bell rang dismissing class.

When Hillary stepped into the sea of students her eyes immediately fell upon her prey: Thomas Seifer. Tom was the sexiest guy in school with his long blond hair, broad shoulders and sparkling blue eyes that could melt a woman with just one glance. And even better, last she’d heard, Tom had not yet found a date for Prom. She’d made up her mind that he would be her date, and she would do whatever it took. Besides how could he resist her with her newly acquired breasts and picture perfect make-up?

Sidling up in front of him, Hillary batted her long, obviously fake eyelashes at her prey, and cooed, “Do you have anything on for next period, Tom?”

“Just study hall,” the handsome young man answered laconically in a flat tone. “Why?”

“I thought we could go somewhere and get friendly,” Hillary answered in what she hoped was her best flirtatious manner.

“Don’t you have a class to go to?” Tom pointedly wondered, as Hillary was known to the entire populace of the school to be on the bottom of the senior class, grade wise. The only person who had a lower G.P.A. was a poor girl by the name of Felicity Green, who had died in a car crash the year before; although apparently the school administration hadn’t yet tumbled to the fact that she was dead and kept giving her zeros in her classes daily.

“It’s just that stupid old world history,” the young woman, who had once been voted by her classmates as being the closest thing to the bottom of the food chain, answered. “Who cares about the past? I want to live in the future,” Hillary emphatically claimed.

“Well, in the future, you’ll still be trying to get out of high school,” the handsome young man muttered.

“What?”

“Oh, nothing,” Tom responded.

Hillary wasn’t pretending that she had not heard. Her denial system was so solid that she would automatically filter out anything she was confronted with that didn’t fit her picture of herself. As a matter of fact, Hillary maintained straight D’s despite hardly ever attending class and when she did go, she paid absolutely no attention to the lecture, but instead spent the fifty-five minutes popping blackheads on her forehead.

The young woman kept her below average grades by doing extra credit busy work for each class. There were two reasons her teachers allowed this; one being it was necessary to pass as many students as possible to maintain the school’s funding from the state and federal authorities.

The second and much more important reason was her teachers couldn’t bear to keep Hillary in their classes a second longer than was necessary. The very idea of holding her back for another year was completely abhorrent to them. Her nasal whine alone brought discomfort to the entire class as it resembled nothing less than the awful screeching of a piece of chalk across a blackboard and it set everyone’s back teeth on edge.

As soon as the final bell rang and the hallways became completely devoid of students, Tom asked, “Where to?”

“The boys bathroom.”

“Oh, how romantic,” the handsome young man murmured sardonically.

“Yes, I think so too,” Hillary replied brightly.

Taking Tom by the hand, Hillary led him quickly down the hallway and into the men’s room. She continued to almost drag him along down to the last stall and pushed him in. Hillary quickly entered herself and latched the door immediately behind her, almost as if she had done this sort of thing before – no duh!

The young woman knelt down on the filthy bathroom floor, where Tom couldn’t help but notice that small puddles of urine were present. Ugh! he thought to himself. There is just no limit to this girl’s degradation.

Hillary pulled down the zipper on Tom’s pants and liberated his monstrous appearing eight-inch erection. It wasn’t that the young man was that aroused by Hillary’s actions, it was more due to the fact that he was eighteen years old and was almost always in a state of arousal.

In fact, the only time that Tom wasn’t sporting an erection was the several minutes following his experiencing an orgasm. To avoid undue embarrassment, he had taken to wearing baggy trousers several sizes too large to hide his constant boner. Tom would have been very chagrined to learn that he hadn’t fooled his friends at all with this maneuver, who referred to him as ‘the human erector set.’

And, as if that wasn’t bad enough, the young women in the high school were always groping Tom in the crowded hallways between classes for a quick feel of his Johnson. It was a wonder that the poor boy didn’t accidentally go off in his pants at any given time.

“Ooooh, you’re so big,” Hillary cooed.

“You say that every time,” the young man complained. “Does the expression short term memory loss mean anything to you?”

“Hmmm?” Hillary said, while looking up at him with a smile upon her lips. “Should I get naked for you?” she asked dreamily.

“No! For God’s sakes, keep your clothes on!” Tom protested most vociferously.

Aw, he’s so sweet when he gets flustered, the demented young woman thought. And he’s always looking out for me, he knows how embarrassed I’d be if someone came in here, while I didn’t have any clothes on. So he foregoes his own pleasure to protect me.

“Come on, Hillary, we don’t have all day, you know,” Tom spoke plaintively.

“Umph,” was all the young woman was able to answer due to her having already filled her torn pocket appearing mouth with Tom’s mammoth erection. As Hillary continued to slurp and slobber over the young man’s knob, Tom closed his eyes and fantasized that he was receiving oral sex from Hillary’s friend, Allison Wyndan.

Allison was the diametrical opposite of Hillary, at least, physically speaking. She had long reddish-brown hair, beautiful emerald eyes, a face that held the true facets of timeless beauty and an awesome hourglass figure. In addition, the young woman was incredibly smart and creative, had a wonderful offbeat sense of humor and was a very caring individual.

Tom was positive that he was in love with her and he was relatively certain that Allison returned his feelings. Unfortunately Hillary was the fly in their ointment. Every time that Tom made plans to spend time with Allison, Hillary managed to insert herself between them.

Such was the case currently, as Tom was going to meet Allison in study hall when Hillary accosted him in the hallway. As horny as Tom was, he easily could have held off from the young woman’s request except for one reason. Tom absolutely could not deal with the guilt from the look of total hurt and abandonment, which would have been on Hillary’s face if he had declined her offer.

The young woman realized that Tom’s orgasm was quickly approaching as his balls had tightened and he was now rocking his hips rhythmically. Hillary pulled her mouth off his throbbing manhood and looked up at him.

“Please don’t cum in my mouth,” she said.

“Okay,” Tom said and he proceeded to shoot his massive load of jism all over Hillary’s face.

With his cum dripping off practically everywhere on her face, Hillary muttered, “Note to self – be more specific.”

Hillary regained her feet rather quickly, considering she was more than usually befuddled. Attempting to wipe her face that was dripping with Tom’s orgasm with her hands in a rather haphazard fashion, Hillary smiled insipidly and cooed, “Give us a kiss, love.”

Tom felt his stomach flip-flop in instant nausea. Oh lord, save me, he thought as he mentally made the sign of the cross.

“Sorry, I’ve got to run,” Tom replied weakly. “I’m late for study hall.”

When Tom attempted to escape the entire abhorrent situation by quickly stepping by Hillary, she blocked him by literally throwing herself in front of him.

“Wait!” Hillary exclaimed. “I want to ask you something.”

“What is it, Hillary?” Tom asked resignedly.

“I want you to go the prom with me,” the deluded young woman answered cheerfully.

Try as he might, Tom was unable to keep a look of total disgust from crossing his handsome features. Tom began to laugh and then quickly regained his composure, as he couldn’t help but observe the hurt expression on Hillary’s face.

“I’m sorry, Hillary. I’m planning on asking Allison, but good luck on finding someone to go with,” he offered, stepping by the stunned young woman and making his escape from the restroom.

Hillary stood frozen in shock and horror. “Oh no!” she cried out. “Not Allison! I won’t allow it!”

Hillary was suddenly galvanized into more action that she had expended in the previous six months. She quickly stripped off her ugly square-toed black boots (the stench that arose from them was overwhelming) and, carrying them in her left hand, she sprinted across the restroom and out into the hallway.

At least in her mind she was sprinting, although in reality Hillary’s gait resembled a slow paced waddle. Hillary knew that Allison had study period during this time of the day and had a gut instinct, more like a homing pigeon, that Tom was on his way to see her to ask her to the prom.

After Hillary had left the immediate area, Tabitha stepped from behind her opened locker door. She had witnessed Hillary dragging Tom into the men’s rest room and was able to draw a valid conclusion as to what had transpired, as the evidence was still somewhat distinguished on Hillary’s face and even in her nappy, frizzy, reddish-brown hair, which always resembled a rodent’s nest.

Intrigued now, despite herself, Tabitha gleefully decided to follow the horrible young woman in order to catch the next scene in this sordid little tale.

As usual, the dim-witted Hillary had no sense of the fastest route to navigate to reach her friend and she set off in the direction that would take her the longest way around.

In this instance, Dame Fortune had smiled upon Hillary, as she would have been detained by the same hall monitor who had stopped Tom for being out of class without a hall pass.

Study hall was located in one half of the school library, as it always contained several ordinary classes of students simultaneously. Hillary paused after she entered the library and slipped on her black square-toed boots. She didn’t wanted to be confronted by a librarian or teacher at this point for not having shoes on.

She immediately observed Allison sitting at a table toward the back of the library and set off clip-clopping all the way. Tabitha was following closely behind.

When Hillary approached the table Allison was seated at, Hillary broke into tears. The odious young woman had taught herself to cry on command.

“Oh Hillary, what’s happened?” Allison asked caringly, concern written across her beautiful features. If Allison hadn’t been such a loving person she would have gotten rid of Hillary a long time ago as she was extremely needy and annoying, but Allison couldn’t help feeling pity for the seemingly lost young woman. Deep inside she really wanted to try and help the pathetic Hillary.

Everyone else seated at the table stood up and pointedly moved elsewhere. Tabitha, who was standing within earshot, turned and pulled a book open from one of the shelves, pretending to be perusing it.

“Allison, it was awful,” Hillary blurted out.

Tears were falling down her face mixing with her heavy pancake makeup and Tom’s left over sperm, leaving a sticky gooey mess.

Lord, she looks a sight. I’ve never seen her look quite this bad before<,/I> Allison thought.

“What is it, Hillary? Please tell me,” her friend entreated again.

“Tom…Tom,” Hillary simpered.

“What about Tom?” Allison quickly asked, the alarm quite evident in her voice, which even Hillary could recognize.

If you’re upset now, you’re gonna be ape shit in a minute, Hillary thought maliciously.

The dim-witted, but extremely manipulative, young woman had the sense to wait a few beats to keep Allison on the edge of her seat and then she finally spoke, “Tom…Tom dragged me into the men’s room and tried to force me to give him a blow job.”

Hillary caused herself to begin to sob again as emphasis.

“Oh Hillary, are you sure? That doesn’t sound at all like Tom.”

Allison realized full well her friend’s predilection for stretching the truth completely out of shape sometimes. In fact, frequently every word out of her mouth was a lie, including the words ‘and’ and ‘the.’

“Of course I’m sure!” Hillary snapped at her. “Do you think I’d lie about something like this?”

Hillary’s face became contorted and swollen with rage. Heads were craning to look from all around the library.

“No, no, of course not,” Allison pleaded, now greatly embarrassed at the public spectacle the two of them were now offering the rest of the study hall.

A sudden thought struck the beautiful young woman. If this is true, something must been down about it immediately!

“Hillary, you must report this to the principal, this is very serious!”

“Oh no!” the other young woman wailed. “I could never get Tom in trouble.”

“But Hillary –“

“I refuse!” she interrupted and began to weep vociferously. Between sobs, Hillary managed to blurt out, “But the worst thing is, I was going to ask Tom to the prom and now I won’t be able to go because I won’t have a date.”

“I’ll go with you,” the kindhearted Allison offered.

Gotcha, you bimbo! Hillary inwardly smiled and her tears dried up immediately, much to Allison’s relief.

Now that Hillary had finally calmed down, Allison had time to notice that Hillary’s thin, chicken anus lips had a white, viscous substance smeared on them.

“Hillary, what’s that all over your lips?”

Hillary’s hand flew to her face and she quickly wiped away the lingering remains of Tom’s orgasm.

“It’s…toothpaste,” she stammered.

“Hmmm,” Allison said, while thinking, That’s strange, I’ve never known Hillary to brush her teeth much at all, let alone while at school.

The bell rang, signifying the end of class and interrupting Allison’s reverie. Students began to drift from the library.

“Come on, Hillary,” Allison directed, standing up from her chair. “I don’t want to be late for my next class.”

As the young women approached the library exit, Tom came racing in, gasping for breath. He had sprinted all the way, after finally being released by the hall monitor, in hopes of still reaching Allison before study hall let out.

“Oh Allison,” he wheezed, still short of breath. “I’m sorry –“

“Don’t you ever speak to me again, you son-of-a-bitch!” Allison spoke fiercely, slapping the living hell out of him. “Come Hillary, let’s away from this piece of garbage.”

Tom stood completely stunned, rubbing his sore cheek, and watched the two young women walk from the library. After passing under the archway, Hillary swiveled her head in a reptilian manner and grinned maliciously. Tom barely comprehended that there might be meaning behind the look that Hillary gave him, believing her to be a truly good person, if extremely dim.

Man, he thought, what’s up with her? All I did was be late to meet her in study hall.

Tabitha closed the book she was holding and replaced it on the shelf. She understood everything that had just transpired, but the young Goth had not decided what she might do about it.

To Tabitha knowledge was power, to be dispensed wherever and whenever she chose.