City of Canterlot, Valiant Manor, Chambers of Ryler Valiant

Ryler Valiant's coat was soft and smooth, the color of a brown meadow of rye hit by the summer sun. His mane was a complimentary dark brown in color. And if you had asked him, it cast him in a rather drab light. His parents had thought the look of him to be stately and appropriate, no neon colors, no silly pastels. His name was a play on the word "Ryley", which in older tongues meant both "Rye" and "Valiant". But, sooner or later, someone would have noticed they had essentially named the child "Valiant Valiant", and that was far too gauche a thing. Ryler it was then. A fine name for a fine child of a fine family, of fine and noble upbringing.

In and among the nobles houses of the kingdom of Equestria, there were many rules, and many truths. One of the most unspoken, but painful truths, was that it is easier to forgive an enemy than to forgive family. When one's life, one's purpose, one's tradition is bound up in sacred and time-honored ways, breaking from them for personal reasons, no matter how compelling, was a sin of the highest order. Ryler was expected to set aside his own ambitions, and his own dreams, for the good of the family. As his brothers had, and his father, and his father before him, and so on with the mares of his family. All dutifully sublimating their desires to the needs of the line, of the blood.

Ryler could do no less, of course. Serve the family, serve Equestria, serve the pegasai who dominated the skies, moved the weather, who looked down from on high at all those under them; everyone else. So Ryler did as he was taught, and as he was told, and denial became his most constant companion. Of course, the corollary unspoken truth was that the more you were denied something, the more you wanted to do it. Such a truth was given testimony in all the clandestine affairs, court scandals, and secret revelations that had ended both individual lives, and entire houses.

If self-denial is difficult for an adult in an environment of wealth and plenty, it was more so for a young colt who had only recently entered stallionhood. The natural urges of his age, coupled with the secret urges of his particular desires formed a heady mixture. Add in the benefits of a refined life, access, and opportunity. Seal in the pressure cooker of judgement and denial, and let the whole concoction steam for a few years. Something has to give eventually. And it finally did, right on the eve of the biggest wedding in Canterlot in ten generations.

The whole of house Valiant was awash in preparations. The estate itself was being prepared for the after-wedding parties, with each house trying to outdo the other. A visit, even a short one, from the newly wedded couple, one of the diarch princesses, or even one of the Element Bearers would be cachet and currency between the rival factions. Another notch on the belt. As the young Ryler walked the halls of his family’s estate, making his way to his room, he looked about the hallways filled with pegasus-related artifacts and wondered idly if Rainbow Dash would show up. He snorted with the idea that even now, his father might be calculating the cost-benefit analysis of having one of the most famous pegasai in Equestria there… set against the damage the notorious rambunctious mare was bound to cause. All the court would remember vividly the tales of the Grand Galloping Gala, and the Elements were well known for the devastation that seemed to come in their wake. It would seem, he mused, that for every act of magical harmony they performed came a cost in physical chaos and destruction.

The hall which held Ryler’s room also held those of his younger siblings as well as a few extras. While visiting family might be allowed to utilize them, the entire hall would be off-limits to all guests for the duration of the wedding festivities. As such, they had been tasked for other matters, and right now the entire corridor and all the other rooms were empty. Everyone had duties but him and that suited him just fine. He made his way down the hallway, hooves landing lightly and precisely against the stone floor. With a pause, he looked back over his shoulder to make double-sure none were watching, and continued his walk. He strode softly, stepping lightly, moving his legs fluidly, gracefully. Ryler took one feminine step, then another, sighing out as he moved. His steps lacked the harsh purposeful stride of a typical stallion and took on a more elegant set of motions. He let his hips sway some, just a little, as if he wanted his rear to be noticed, but not making too much of a show about it. A downward motion of his head flicked his mane back and over one side of his shoulders. It was a walk he could only ever manage in private, and he relished the chance to do so. For a moment, just a moment, he imagined himself as one of the mares at the court, maneuvering through corridors and ballrooms and court chambers with such an easy glide to their steps.

Ryler’s door was to his right, while the room to his left was unoccupied. With the upcoming festivities, it had been tasked to hold several rolling clothes racks full of dresses, gowns, and various other garments, both over and under. The door was open and he could see all of them. Temptation beckons different ponies in different ways depending on their experience. For some, it would take the Alicorn Amulet, the Mirror Pool, or the Crystal Heart. Others had simpler needs, but temptation, regardless of size and scope, all calls to the same primal hunger to finally relent to an urge that has been long denied. Today, Ryler relented. He turned left and ducked inside the room full of clothing racks. Once inside Ryler looked out the door, down the corridor, and then closed it, locking himself in the room.

He moved from outfit to outfit, scanning them, taking in details, and meanings. As far as he was concerned, every bit of stallion clothing conveyed only two messages: Look how awesome I am, and look how dapper I am. The clothing worn by mares was like an announcement in a subtle language few stallions ever truly could read. They could convey mood, status, availability, and demonstrate personality. Clothing could invite, it could reject. The right dress to convey a mare's harsh domination, or her eagerness to submit. Making that point once to his father had gotten him nothing back but a harsh look. He banished aside that memory and filed it back in its place with all the other misbegotten times he'd been foalish enough to speak his mind in public.

"Whoever said that bits can't buy happiness simply didn't know where to go shopping," Ryler muttered. His questing through the clothing racks brought him to a particular gown that left him shivering in want. The principal color was black with touches of gray, white, and silver threading. Black could be modest and arrogant at once, lazy, but also easy, even mysterious if done with the right aires. And black, he noted, went well against his brown-colored coat. He wasn't needed the rest of the night so nopony would come looking for him. He had no friends to speak of, and the family had long ago given up trying to penetrate his maudlin shell. His presence would not be missed from anything happening in the house that evening, and neither would the gown.

A snap decision, once made, leads to decisive action. Ryler had probably been browsing dresses for the better part of half an hour, but once he’d decided what he was going to do time sped up with urgency. He pulled down the black outfit he’d been eyeing, along with the accompanying stockings, undergarments, and some of the silver jewelry in one of the boxes. He gathered his haul, folded them all together, then set them on a dresser next to the door. Unlocking it, he peeked out, and found himself alone as ever. Still, the short trip across the hall, and through his bedroom door felt like an intense spy mission, and he panted with relief when he was safely locked within his own room, falling back against the door, and listening to the hammering of his heart in his chest. But the first goal had been accomplished and his blood quickened more with excitement than fear. The young stallion made his way to his bed and began to change.

Seeing mares in their clothing, studying them, even reading books about their clothing was hardly proper compensation for a lack of experience, and Ryler’s inexperience was bothersome in the extreme. Sliding on the stockings took delicate work, he had to be careful not to tear the material, or stretch it wrong. It should all be second nature, it should all just glide on, as if he were every inch the mare. But he wasn’t, and the divide between reality and fantasy kept creeping in -just- as he was getting into it. He slipped on the undergarments with a trepidation that gave way to quietly moaned sighs of pleasure at the feeling of the material against him, a combination of right and wrong that teased and aroused him. Her. That’s what Ryler felt like…he felt like a "her".

She moved with a slink along the bed, relishing the half-dressed state. In her mind, she imagined she was posing, showing off, saucily taunting some impressive stallion. Closing her eyes, she pitched her voice higher, and let out a whimper of arousal, which became a frustrated whine. Damn it. Being a mare was not all about sexuality, it certainly was more than writhing on the bed like a slutty noblemare waiting for her secret lover. Being a mare was a matter of spirit and personality, a matter of ones… oh sweet Celestia, was he really ruining this moment by delving into gender politics and matters of equity and social consideration? He wanted to be a mare in all respects, but right now he just wanted to be a mare in sensual heat. Just to pretend, just to run with it, just for once to let go and be the hot, sexy, slinky mare he wanted to be. ARGH!

With a grunt, Ryler got up. Since the arousal of the moment was broken, he… she… decided to finish dressing. It would be such a waste to have gone this far and not complete the transformation. And so she busied herself once again, sliding the dress on, tucking it here and there into position. The act was liberating, heady…. she felt as if she were floating on a cloud, each step in the process making her more and more a mare. She entertained thoughts of sneaking away from the family party and ducking into the revels of another house. Could she do that? Move among others at a party, flirt with available young stallions, touch her makeup up in the mare’s bathroom. The idea of doing so left her with a gleefully floating sensation, a giddiness to her senses.

Once the dress was finished, she selected jewelry; anklets, a little tiara. The clip-on earrings would wait for the mirror and be her finishing touches. When the jewelry was done she slipped on the two pairs of shoes that went with the outfit, lacing them delicately. Finally, she sighed, eyes closed, spreading out her wings, and moving her hooves to feel out how the dress had settled over her body. This felt so right, so wonderful, so sexy and sultry, so… her, it felt so very her. She’d done it, she could do this… she could! All she would have to do was plan, maybe escape a bit now and again as her older brothers and sisters had from time to time. Nobody from this house would ever knew where to look for her, not at the clubs she had in mind to go to. But she’d heard of them, everyone had, whispered here and there. She could find them.

Closing her eyes, she laid back on the bed and she slowly touched herself all over her body, her mind awash in plans. Places to hide a cache of clothing, how to sneak out, what she might do, putting those dancing lessons to use, how to change her voice just so. Her thoughts drifted to other things whispered about; gender changing potions and spells, a permanent shift, even a new life, the life she should have had. She fluttered her eyes open and sighed with the sheer volume of possibilities. First, though, it was time to put on the earrings.

Ryler slid off the bed, all smiles and feminine motion, and walked her way up to the mirror. She took one shuddering breath, posed herself, and turned her head to look at the mare she had become.

It was disgusting.

Nothing was right. The shoulders were lopsided. He hadn’t managed to get the stockings to the same height on each leg. The fabric of the dress bunched up in all the wrong places and it was off-kilter back behind his wings. His mane was wrong. It was cut in a stallion style that contrasted obviously with the dress and he’d forgotten all about that. His tail as well was unkempt, not even remotely soft or styled like a mare’s. His face was too masculine, his posture all wrong. His supposed pretensions to being able to move like a mare were exposed for the obvious self-delusions they were. He had been floating, now he’d fallen, and hit the cold ground very hard.

He wasn’t a mare. He wasn’t even a passable imitation of a mare. He wasn’t even a campy joking passable imitation of a mare one might dress as for a comedy masquerade or a burlesque show. He was an utter laughing stock is what he was. This was why mares dressed one way, and stallions another. Maybe… maybe, with classes on how to act, and magic potions, and when he was old enough to live on his own… maybe then he could pull it off. Maybe. But right now, he was not a mare, he was not a femcolt, he was just a young stallion who had ruined a dress, and made a fool of himself. And by the time he could ever manage the freedom to be what he wanted to be… he would never be able to free himself. Family was everything, he couldn’t get away from it. Not like other stallions could. This whole enterprise had been a disaster from beginning to end.

Ryler sighed out, avoiding the mirror as he sat back down on the edge of the bed, pulling the last of the stockings off, flicking them away from him in disgust. The feeling that came over him was a dull, numbing, aching feeling, coupled with an extreme tiredness. The young pegasus wanted nothing more than to crawl into his bed, pull the covers securely over himself, and just cease to be for a while. In the back of his mind, he thought about collecting all of the clothing now scattered about the floor in the hope that, upon waking, there would not be a reminder of what had just happened. Right at that moment, though, he didn't think it would make a difference, and he didn't care either way.

Letting himself topple over to one side, Ryler landed on the bed with a soft thump against the sheets. He was reminded of a time as a foal when he'd seen a rather large cat make a leap for the dining room table, only to topple backwards and capsize over the edge like a sinking ship. That brief flash of happy memory brought out a giggle from the stallion, and then a frown as he sealed his lips tightly shut and felt another wave of melancholy wash over him.

Raising up one forehoof, he moved it to his neck, and stroked it up and down. That voice of his, that sound it made, it gnawed at him. It had bothered him so much that, for a while, he seriously considered going mute. Everything masculine about Ryler disturbed him. Worse than the mane and body that seemed to belong to someone else, or even the face that he couldn't recognize in the mirror, was the behavior that had typified male existence within his house, and his strata of society. When he caught himself doing what he had been told his whole life, what he should do as a stallion; being forceful, crude, powerful, and aggressive, it made him feel empty inside.

"You are the most miserable little pony in the world, aren't you?" The voice that spoke out hissed out each word with a certain crisp asperity, almost as if it was just a few intonations short of hissing each syllable. The sound sent Ryler bolting upright, and swiftly turning his head to gaze at the speaker. He was a tall, lithe unicorn stallion, with a dark red coat, and even darker red mane. There was something about him that was just off in every sense of the word. His eyes were pale gray and cruel, his bone-white teeth were unnaturally perfect, not a hair was out of place, and every muscle seemed sculpted. He was utterly beautiful in a way that made Ryler ache with desire, and terrifying in a way that left him feeling as if a knife's edge was already at his throat.

Much as Ryler hated his life, years of training and discipline had hardened him some and prepared him for the unexpected. He could at least take some solace in that he didn't cower. He pulled himself up as best he could from his position on the bed, and spoke out calmly as he could muster. His voice wavered some, but he managed to keep most of the fear out of it. "What's it to be then? Kidnapping? Assassination? You probably picked the least valuable member of this family to attack you know. Nobody's going to shed a tear over my death, or pay much for my ransom... whomever you are."

The unicorn smirked at him. "Rasp... call me Rasp." He grinned. "I like the way you think, pony. It's very tactical... you're trying to undervalue yourself and are willing to sacrifice someone else in your family just to keep your own hide intact. Excellent!"

"Wait!" Ryler protested. "It didn't mean it like that. I just meant..."

Rasp cut him off with the wave of a hoof. "No no, boy. Don't sell yourself short. Personally I think it's wonderful you have such a self-interest in your own survival. And it would be such -delicious- irony for you if it was one of your brothers kidnapped, taken, and made to whimper and beg for his life..." Rasp paused, and smirked at Ryler. "...like a little mare perhaps? But you needn't worry, I am not here to kidnap you or kill you." He chuckled, looking down, and picked up one of the discarded artifacts of clothing. Holding up a set of silk undergarments, he twirled them around a hoof. "Entertaining a guest, young pony, or are these perhaps yours?"

Ryler shot Rasp an angry look, sneering at him. "Like I would tell you anything. What then? One of my father's friends? Did you come in here perhaps hoping to bugger one of your associate's children?"

Once again Rasp gave him an approving grin. Something about Rasp approving of anything he did or said was oddly disturbing. "Well done again, pony. You evade the truth rather than weave a lie, confirming nothing, and offering no story that could later be picked apart. You attack with barbed words, hoping my angry response will expose a weakness. You'll make an excellent Infiltrator."

The pegasus blinked a few times. "A what? What are you going on about? No..." He rolled his eyes and gestured with a wing. "You know what, keep going on and being enigmatic. Reveal what this is all about at a snail's pace. You have no idea how that thrills me," Ryler said with an utterly deadpan voice.

Rasp shot the young lord an amused look. "You have a wonderfully feminine lilt to your voice when you're being venemous, do you know that?" The unicorn slowly paced the room as he spoke. "Actually, I'm here to give you a little gift. Something you've always wanted, pony. Something you've ached for so much that even now it's keeping you from shouting for the guards, pulling the hidden alarm bell behind your bed, or going for a weapon. It's the least I can do to reciprocate all the sustenance you have given me."

Ryler worked his mouth for a few moments, though nothing came out. Rendered mute on one of the few times he would have liked to have spoken immediately and clearly. He looked back up at the disturbingly perfect stallion and blushed intensely as he was made aware of something he himself had not consciously realized. Rasp was right, Ryler was, in the back of his head, hoping... hoping this would end in a very particular way, a way he'd daydreamed about many times. It shamed him to admit it to himself. It shamed him further since all reason told him life just did not play out in the manner of some erotic fantasy. And if it was going to, it certainly wouldn't happen to him. Still, no alarm was sounded, no scream went out. Ryler gulped softly, bit his lip for a moment, a moment....

But no, it was gone. His ears folded down, and he spoke out sharply to Rasp. "No. I don't know what you're going on about, but I'm going to believe you're here to do me favors as much as I believe you're Princess Celestia."

"Very well, " Rasp said. "Be it so."

With that, his horn flashed with a sick, mutagenic green glow. Equally green flames formed a circle around where he stood and then rose around his body. Rasp vanished in a flash of magic light and flame, leaving Princess Celestia was standing in his place. She looked down at Ryler, and smiled a very un-Celestia smile. Ryler had seen the princess before any number of times in his life; she had always been serene, saintly, her smiles comforting, forgiving, welcoming. To see her have the smile of a sadistic predator was downright disturbing. A bit like having your favorite stuffed animal come to life and try and kill you.

On balance, this really wasn't Ryler's best night ever.

Author's Note

A lot of Ryler's feelings in this chapter are both autobiographical, and reflective of the experiences of others in the trans community that I know.

Special thanks to Korenav and WellaWeiss, again, for their amazing help editing this chapter. Watching them editing live via Google Docs was a vivid reminder of just how much effort a good editor puts into their work.