Cheerilee made her way through the streets of Canterlot toward her lodgings.
She could have cut right over to the main avenue and, from there, quickly made it to her home street. She did not. Instead, she wandered, obeying some strange whim not to go home.
As long as she remained out, she was in a sort of intercalary time between the disaster of that drunken party and the routine problems -- now made far worse by her need to change pretty much all her plans in the wake of her breakup with Tower Climber -- of her ordinary life. She had been putting this last off for a while now, and she still hadn’t decided what to do next.
While she wandered, she need not decide. Briefly, she could imagine herself whole and free again, as she had been as a child and adolescent. As she had been at thirteen.
She had hardly thought herself free, then, and perhaps she had in truth been less free than most young Ponies. In addition to school and chores, she had been forced to take responsibility for all her own decisions, and many affecting Berryshine. The fact that she had been almost entirely independent of parental supervision -- Strawberry lacked both the desire, and, really, the capability to supervise her -- was less blessing than burden, for it meant that, if she forgot to do something vital, it would not get done.
School was pleasure, rather than chore. She was Play Write’s most prized student, and she was aware that her teacher wanted her to apply for a scholarship to a good secondary school.
Absent such a scholarship, she would simply end her formal education next year; probably, get a job working for the vinyards of one of her actively-farming Berry kin. Most of them knew and liked her; she had worked for some of them over summers and helped out at harvests; and more than one of them had suggested hiring her long-term after she finished school.
These were good offers by Ponyville standards. Cheery was a hard worker and used to the tasks. As a well-regarded and well-educated Berry, she would reasonably expect to in time advance into the business end of berry-growing and wine-making. She might have opportunities to deal on her own account, or even start her own vinyards. She might do quite well for herself.
It was potentially a good life. But Play Write thought that her prize student could do better. Periodically, she handed Cheerilee application papers for various scholarships. Generally, this involved filling out a form and writing an essay on some topic or another. Strawberry also had to sign them.
Writing the essays was easy. Cheerilee liked to write.
Getting Strawberry’s signature was harder. Always, her mother wanted to “go over” the paperwork, which usually meant squirrel it away somewhere and forget about it until it was past due. After one or two such disasters, Cheerilee simply started forging Strawberry’s signature for this, as she did for other purposes.
It was not as if Strawberry would remember what she had or not signed weeks or months later, anyway. Strawberry had trouble remembering where she’d been two days ago.
Despite the effort she put into them, all those scholarship applications seemed somewhat theoretical to Cheerilee, not really part of her normal life. It was all sort of a game she played with her teacher, because it was fun to imagine going to some really good high school, and the attention was flattering. She was thus very surprised when, early in 1486, Play Write took her aside to inform her -- the teacher’s voice bubbling with badly-suppressed excitement -- that Cheerilee had won a full scholarship to Canterlot Secondary.
Cheerilee had, of course, heard of Canterlot Secondary. It was one of the elite preparatory academies, readying the daughters and sons of well-off Canterlot families for their careers, or to go on to university.
The tuition was well beyond anything Cheerilee could have ever dreamed of affording with any income she could earn as a teenager. It was, simply, the single biggest breakthrough Cheery could ever have hoped for.
Play Write had helped her get this chance, but her help did not end with the scholarship approval. It soon became apparent that the genteel Fillydelphia Mane Line born school teacher was by some means well aware of Strawberry’s irresponsibility, and hence that any funds placed into the trembling hooves of Cheerilee’s mother might well simply vanish down that mare’s thirsty throat, in the form of more-than-commonly liquid assets.
It was Play Write who asked Cheerilee which of her Berry kin could best be trusted, then had a trust-fund contract drawn up with a lawyer.
Then, Play Write had a private interview with Strawberry.
What it was, exactly, that Play Write said to Cheerilee’s mother, Cheery was never to know in detail. Later, when she was older, she could make an educated guess. While an adult Equestrian mare could drink as much as she wished, and have sex with anypony and everypony who consented -- even, in the case of the latter, do so for money -- and in the process commit no crimes, nevertheless, an alcoholic prostitue might well be judged no fit guardian for minor children.
Even her own.
Cheerilee reasonably speculated that Play Write had, rather insistently, reminded Strawberry of these facts, and used her mother's subsequent awareness of the situation to induce her to agree -- or at least acquiesce -- to the teacher's plans. It occurred to Cheerilee -- both then, and even more so later -- that this conversation must have been extremely unpleasant for both of them, and that Play Write had gone far beyond her normal duties as her teacher, in pursuit of Cheerilee's own interests.
Whenever she thought of this, Cheerilee felt grateful. For, while Strawberry's decline had, so far, not directly harmed either Cheerilee or her little sister; there had been no assurance that this would have continued to be the case, as Strawberry fell further.
Cheerilee was especially glad for Berryshine. While Cheerilee was sure that she herself could deal with any trouble Strawberry brought home, she sometimes worried about her little sister. Strawberry could not be trusted to watch her, and at seven she was in some ways even more likely to wander off into trouble than she had been at three. And Cheerilee would not be able to take her to live with her at Canterlot.
In the end, Play Write, Strawberry and Cheerilee arranged to have Berryshine taken in by the Wineberrys -- relatives who owned a fair-sized farm northeast of Ponyville, and easily close enough to town for the filly to complete her education. The Wineberrys welcomed their young kin, and Berryshine's help in their vinyard would defray the cost of her upkeep.
Play Write had the lawyer draw up, a notary witness, and Strawberry sign the necessary papers. In this case, there could be no shortcuts through Cheerilee's forgery: Strawberry's consent, even if grudging, had to be both geniuine and beyond successful challenge. Berryshine's whole future might depend upon it.
Cheerilee's wanderings had now taken her to a small square, about midway between the run-down townhouse and her own quarters. In the center was a sungold statue -- well, Cheerilee amended, it couldn't really have been pure sungold, as that much pure sungold would have been almost impossible to afford or cast, even by the standards of the Realm; certainly for such a trivial purpose as a single public statue. The statue was that of a stylized sun.
The inspiration for this sun was obvious. It was in the form of the most famous Cutie Mark in all Equestria: the one borne by Princess Celestia herself. By chance or design -- and Cheerliee strongly suspected the latter -- none of the tall towers around the little plaza blocked the rays of the real Sun, which gleamed most marvelously off the sungold metal, the reflections playing about the entire place.
The stylized Sun was supported by, and rose over, a white marble base, cunningly composed of three equine figures, all young mares: an Earth Pony, a Unicorn and a Pegasus. Their expressions shone with enthusiasic idealism: friendly and innocent. There was something about them that Cheerilee found fascinating, though she found it difficult to fathom precisely why.
She glanced around the Plaza. Ponies were crossing it from one street to the next, but none seemed interested at the moment in lingering. There were three wide benches before the statue, none of them currently occupied.
Cheerilee chose the center bench and sat down.
Young Cheerilee had secured lodgings not in Canterlot proper, but in Cantergate, the town three miles along the road down from Canterlot, proper. Cantergate had started as a small fort, guarding the ground approach up to the Palace at Canterlot, which spread out in all its marble-white and moonsilver and sungold glory on a southeastern part of the same great outcropping on which was built Canterlot the City. Any attacker driving up the road from below would have to first carry Cantergate, then the Palace, before they could do harm to the Ponies of Canterlot the City.
This was more than a purely-theoretical situation. It had happened many times before: most recently, in the Year of Harmony 1449 -- a mere thirty-seven years before Cheerilee came to Canterlot Secondary School -- when the horrid Formless allies of the Southern Secessionists had assaulted Cantergate, bombarding it with Moonfire and trying to overrun its walls.
Cheerilee's own father, Falcon Punch, had been a seventeen year old ensign at the time of that battle, though she didn't know if he'd been in it -- most of the Guard had been deployed elsewhere, fighting the Secessionists along the Motherwater and Gulf Rivers. That was why Princess Celestia was forced to lead a combination of the few Guards on the scene and a hastily-mobilized civilian militia to throw them back. Cantergate had burned, and the defenders had taken severe losses before a relief force could reach them, but the Palace and City themselves had both survived unscathed.
Every schoolday, Cheerilee washed her face, quickly brushed her mane, grabbed some morsel of breakfast, and walked almost four miles to school. Some might have considered this routine burdensome; to the tough country filly, young and healthy and strong, it was no hardship.
She no longer had to care for Berryshine as well, nor clean up after Strawberry when she came home, and the lifting of these shackles meant that her life was filled with time and energy as never before. She fairly flew up and down the road to school, trotting or even cantering most of the way. This saved her precious bits -- only when feeling ill did she deign to take the train.
As she ran up the road, her mane streaming in the wind, passerby often smiled at her, and she felt beloved by all theworld. She almost always smiled back, sometimes playfully tossing her head by way of greeting. She especially smiled when she saw the brave Guardsponies, for her father had been one of them, and for those she had even greater warmth inn her heart. But mostly, she just loved everypony.
She was full of joy, because, for the first time in five years -- for the first time since the death of her father -- she was free.
Cheerilee had been realistic enough, even at fourteen, to know that there might be problems for her, as a not-so-rich country filly, fitting in at an elite school full of rich Canterlot Ponies. She had come resolved to endure whatever hazings awaited her, and establish herself as a respected member of society among the students.
Things went even better than she expected.
To begin with, her fillyhood friend Mare Ivory Scroll was coming to school with her. That helped a lot, both emotionally and socially. The Scrolls were an old Mount Avalon family -- not from Canterlot itself, but from Colton in the foothills, which was a singificant step up, both in terms of altitude and of society, from Ponyville. What was more, Mare Ivory already had friends at the school.
So it was that Cheerilee, instead of coming in to Canterlot Secondary School as a friendless, hopeless country mouse, came as the friend of somepony who already had friends there, and hennce had an introduction into at least one segment of CSS society.
It was not the best segment, of course. Neither Cheerilee, nor her new friends, were either wealthy or highborn. Few even qualified in the gentry.
They were, instead, decent and solid children of the middle classes; of that order of Pony who were leading their nation into this new Age of Invention: the future businessponies and engineers and educators and scientists. While by no means merely a lot of grinds, they for the most part seriously valued the many educational and professional opportunities that the school afforded them.
Cheerilee had fallen among Ponies especially inclined to appreciate herself.
With the social grace that came naturally to her, she took ample advantage of the situation. She charmed many of her classmates, and made herself quite useful to the studies of quite a few. She as not as brilliant a scholar in the setting of Canterlot as she had been in rustic Ponyville, but she was still an intelligent and hard-working young mare, and she was very willing to help others excel.
She might have run afoul of bullying, by those envious of her intellect or desirous of her services without being willing to pay her in the coin of friendship. But she was no soft and pampered town filly -- she was a tough country girl, and it took more than the upper-class urban imitations of bullies to intimidate her. Her wit and charisma confounded social snobs, while her strength and courage fended off more direct physical challenges. It soon became apparent that the filly from Ponyville was too tough to abuse, and aggressors sought easier targets.
So Cheerilee did well, in every sense of the word, at Canterlot Secondary School. She was of course forced to live frugally -- she was being suported from the same small trust fund which was paying her tuition, but this did not go far given the high cost of living in Canterlot. Play Write had warned her of the expenses; however, the filly was still astonished at the price of food and clothing on Mount Avalon, let alone in the City proper.
Cheerilee had half-resigned herself to a very ascetic experience in Canterlot, observing the life and luxury of the capital city from the outside, like some ragamuffin orphan filly with her snout pressed pathetically against the great glass-paned front window of an amply-stocked sweet stock, unable to afford even a morsel of the rich bounty stored within, when the solution to her problem became clear.
Some of her schoolmates were, as has been intimated, very rich. Some were very smart. However, sad as it may be to relate, those who were very rich and those who were very smart were not always the same students.
In short, some had bits, and some had brains. Cheerilee fell squarely into the latter category.
Which suggested an obvious trade.
So it was that, a couple of months after her arrival at Canterlot Secondary School, Cheerilee set up a small tutoring service.
She would not help anypony cheat -- that was her ironclad principle. But she was willing to devote her not inconsiderable skills to teach her students, so that they didn't have to cheat -- and she was better at this than were most of the teachers at Canterlot Secondary School. In the process, she earned the respect and sometimes the friendship of those clients.
The fees she asked for these services were high by her previous Ponyville experience of money; bargain-basement by the elevated standards of Canterlot. It was Mare Ivory who brought this fact home to her, and told her what to do about it: with misgivings, Cheerilee raised her rates.
She was surprised to discover that she acquired even more clients this way. In her then-naive understanding of economics, that should not have been possible: later, she realized that by her initially-low rates, she had been undervaluing her services, and hence failing to make her clients fully appreciate them.
Soon, she found herself flush with money, compared to her own simple wants and needs. She already had enough income from her trust fund to pay for tuition, lodgings and basic nutriton: now, she could afford some luxuries. Treats from food shops; books not entirely necessary for her courses; pretty clothing for parties. For, now that she had made the acquaintance of some of the richer and classier Ponies through her tutoring, she found herself invited to some of their social gatherings.
At first, she was terrified; afraid that she would make a fool of herself by some gross social gaffe or rustic crudity. She fled to Mare Ivory, and that worthy suggested that she bring her to the party to help advise her on proper behavior. (Later, she realized that nopony had invited Mare Ivory to any of these parties, but she did not begrudge her friend the use of her tutoring connections, especially given that Cheerilee had received her initial introductions to school society that same old friend).
She need not have been worried. She simply bought a nice frock, got her mane done, and went to the party. In addition to the host, several of the other attendees were her clients: they appreciated the help she had given them, and welcomed her warmly into their company. Cheerilee behaved with her usual charm and decorum, and had a wonderful time.
In consequence, she received many more invitations.
Cheerilee loved her first year at high school.
If there was a fly in this ointment, it lay in her separation from her Ponyville friends.
Mare Ivory was at school with her, to be sure, but she missed many she had left behind -- her little sister Berryshine, her best filly friend Cup Cake, and her benefactor Play Write. Her mother she sometimes worried about, but, perhaps shamefully, could not really bring herself to miss at all.
And, of course, there was one other Pony whose absence she felt. Her -- she did not know exactly by what term to think of him -- dear friend and confidante, Big Mac Apple.
Cheerilee missed Big Mac. Not so much when things were going well: then, she sailed smoothly on the seas of Life, adroitly trimming her sheets to the winds, navigating past the rocks and maelstroms on which clumsier Ponies might crash. Often, she guided those other Ponies away from those hazards, for it was in her nature to keenly feel the misfortunes of others.
But, when the voyage was past, and she once again safe in harbor, then she much wanted to rest berthed beside a trusted friend, one to whom she could tell her tales, and share peace of spirit. And in the past, this had been Big Mac.
And worse, when her adventures went poorly, and the world hurt her, and she needed repair and resupply, or still worse rescue -- then, she really needed a loyal friend. And, on a few occasions in the past, this had also been Big Mac.
She was not sure what she felt for him. Strong friendship, to be sure. But now, as she approached fifteen -- the age which had once been that of maturity in Old Equestria, and which still had strong connotations to Ponykind, she was becoming increasingly aware that there were other and more intimate possible relations.
She had Cycled, with increasing intensity, for the last four years, and learned to deal with the intense, frightening feelings her time roused in her. She dealt with them decently, with suppressors and, in private, self-stimulation. She very much did not wish to be wanton, as her mother had become.
She saw that some of the Ponies in her grade were already beginning to court: not the childish courtship of colts and fillies, but the more mature courtship of young stallions and mares who were well-aware that in a few years they would be old enough to get decent jobs, marry and start families of their own. Some of the students in higher grades were already betrothing, or "getting engaged," as the Canterlot Ponies called it.
In that context, the possibility of relieving her desires by means other than masturbation became increasingly plausible. She would not sleep around -- no, she was determined to be a good mare -- but she might be willing to permit serious liberties to a stallion she loved, even before marriage.
Needless to say, thoughts of such dalliances often occupied her mind during the times she spent alone in her bed, relieving herself of the pressures of her Cycles, lest she behave badly among actual stallions. And at those times, Big Mac sometimes figured in her fantasies.
Had Big Mac been her age, of her educational class, and lived in the same town as her, she knew what she might have done; what she probably would have done. Not given herself wholly to him, no, not yet, for she was a decent young mare.
But she would have gone out walking with him, and talking with him. And they would have found some semi-private place and leaned with him, and held it just that bit longer, so that he would have known that she was sweet on him. And the talk might have become increasingly affectionate, and if it led to hugging and kissing -- she would not have objected.
No, she would not have objected at all.
And the other things she imagined, when she lay alone in her bed during her Cycle, with her hoof or tail between her legs touching her most private places in the special manner that every young mare learns when she begins to Cycle -- well, in time, if he was good to her, she might do those things with him as well. She could control herself. She knew that. She was good.
And Big Mac had always been very good to her.
It always seemed simple -- so very simple -- when she touched herself. There were no problems, no issues of where they lived or how well they were educated, or even what they wanted to do with their lives. There was only Big Mac, as she remembered him, big and warm and loving, bringing her to wonderful new worlds of delight such as they never really had when they had been together as friends in their childhood together.
To her, childhood was past. It had started to end when her father had died and she had to be the parent Strawberry refused to be. But it had really ended when she went to Canterlot Secondary School. Now she was fifteen. And Mackie was thirteen.
And that was the real problem, might always be the real problem (to young Cheerilee, brilliant though she was, "always" still had the short time horizon of the adolescent mind). There was no way that a mare could go stepping out with a colt, a child two years younger than her.
So it was that, when she went home on her vacations, she did not do any of the romantic things, even the tamer things, that she had imagined doing with Big Mac. She was a very clear-headed young mare. That was fantasy -- perhaps a vaguely sinful fantasy, given that he was two years her junior. This was reality.
And in reality, it would be a terrible thing to do to her dear friend, the one who had helped her stay sane after her father's death, to seduce him and use him and then have to drop him when she found a real colt-friend. This would be true, even if she went no further than hugging and kissing, because she knew Mackie well enough to know that, to him, it would be serious. She knew that if she treated him like this, she would break his heart.
So her times back in Ponyville with Big Mac stayed mostly chaste, though she did of course walk with him and talk with him, sometimes in semi-private places. She was not entirely immune to the pleasure of being alone in the woods with an admittedly handsome and muscular and bright and friendly and entirely dear colt, for she was despite her best intentions still a rather young mare, and the hearts of young mares do beat a bit faster in such situations, even if they are geniuses who win scholarships to top secondary schools.
She could of course sense that Mackie wanted her, and as more than just a friend. This would have been obvious even were they not both Ponies, even if she could not, nestled close to him as they sat and leaned together alone in the woods, hear his own heart beat faster, smell his own arousal, with all her equine senses. She would have known this in any case, for she knew Big Mac better than she knew all but perhaps one or two of her other closest friends.
With another stallion ... colt, she reminded herself, only a colt ... things might have gotten more difficult. He would have pressed his suit, begun kissing and nibbling her, and she would have had to break away to avoid temptation. Certainly, she would have broken away.
Though at this point in her life, nopony had yet behaved this way with Cheerilee, because she had not met anypony save Big Mac about whom she seriously felt the temptation and thus put herself in a situation in which they might try to take such liberties, she knew the sort of things that went on. She was a sophisticated young mare, she told herself, nopony's fool.
But Big Mac was shy. Not normally all that shy with her, but that particular situation -- being with her and pereceiving her as a desirable young mare -- that situation made him shy again, shyer than he had ever been before with Cheerilee. Also, he deeply repected marehood, and he would never touch her in any way she had not previously accepted, without her clear invitation.
And she, amoral monster that she was, as she later told herself when she was free of the temptation of his sweet presence, she took full advantage of this shyness and respect. For when she was with him, she could not see him as a colt with a mare, but instead, she saw him as her stallion. And she could enjoy stepping out with her stallion, without having to do anything that would in all decency make her his mare for real.
And of course, she never went stepping out with Mackie when she was actually on her Cycle. If she did that, she greatly feared that they would both lose all self-control.
When others were around, they were but friends as they always were. Though her two other best friends, Ivory Scroll and Cup Cake, sometimes eyed her suspiciously, when she stated clearly that she and Mackie were no more than friends.
"It's nothing romantic," she told Cup Cake once. "No more than you with your friend Carrot Stalk."
"Um ... okay, sure, hon," replied Cup, looking embarrassed about something. "No more than me and Stalkie. Heh."
At the time, Cheerilee congratulated herself at the highly-successful deception she had practiced upon one of her best friends.
Another time, she had been walking in the woods with Big Mac, and they had perhaps leaned wordlessly against each other a bit too long, and she had perhaps let him hug her once too often, and experienced a brief wordless thrill when she pressed against his belly more tightly than usual, and felt his arousal against her own hide in a manner she never had done with anypony before ... and he kissed her.
Not on the lips, because she turned aside at the last moment, and received that kiss on her cheek. And she looked into his deep green eyes then, and she saw something in them that frightened her, because it was beyond friendship, beyond lust, it was love, and she felt her own soul responding to his call, and she couldn't, all her schoolfriends would laugh at her, if she started seriously dating a colt of thirteen.
She couldn't just ignore Mackie either, that would be too horribly cruel, so instead she smiled at him, and gave him a quick peck on the cheek also by way of return, "You're my best friend," she told Big Mac, and it was very true, but also deliberately incomplete.
Suddenly she felt that what she was doiing with him was very wrong. Not that she had come very close to sparking with him, but that she was stringing him along. Because no matter what she let him do, she could never be his mare. He just didn't fit into her new life, her new world.
What am I doing? she asked herself, dismayed. He's always been good to me, always been there for me, and I'm just going to use him for a thrill! No!!!
"This is wrong," she said aloud, and saw his face fall, his ears droop, and she wanted to explain to him what she really meant, but could see no way to do it that would not make him feel far worse. "I have to go. I just have to go."
She went, galloping away.
He did not try to stop her. He was, as always, respectful of her wishes.
Sometimes, later on, she wished he hadn't been quite so respectful of her.
For, by then, she knew she didn't deserve it. Had never really deserved it.
But that was much later. The rest of that summer, she and Big Mac continued to be friends, but not quite as close and before. He did not try to kiss her any more.
And then she went off again to school.
Cheerilee had another birthday. She turned sixteen.
She became even more popular at school. She still didn't have a steady colt-friend, but she started to accept invitations to school dances. She dressed more boldly, in extreme fashions of skirts and socks and leggings, hair teased out into huge mops, in the manner that was then coming into mode then.
The colts ... no, young stallions ... began to flock around her. And they often tried to lean her, and sometimes to hug her or kiss her. And sometimes she let them kiss her, though not very deeply.
But she was not very interested in the young stallions, and she did not want to think too much about why. Because, when she looked into their eyes, she did not see what she wanted.
They were mostly good stallions -- though once or twice she had to show an overly-fresh stallion how a Ponyville filly dealt with male presumption, and he went away with her hoof-mark on his cheek. Only once or twice. For they were mostly good stallions, and Cheerilee had a good reputation at that school.
But their eyes were the eyes of strangers, or at best casual friends. They were not deep green eyes, gazing at her with utter caring and devotion from a red, freckled face, huge and heavy-jawed, and oh so dear and familiar. They were not his eyes.
And she began to wonder if sixteen and fourteen was as big a gap in age as fifteen and thirteen, let alone fourteen and twelve. And she began to imagine that, perhaps, she might behave a bit differently toward Mackie the next summer.
Then everything changed.
For she met Cool Lines.
And for the first time in her life, or so she thought, she really fell in love.