Dressed to Impress

by Ice Star

Rating: teen
Tags: Romance, Princess Luna, King Sombra, My Little Pony: Friendship is Magic
Length: 4672

On a casual visit to spend time her lover, Luna finds something rather startling. Sombra is in a dress. He says he can explain. How could this possibly go...?

On a casual visit to spend time her lover, Luna finds something rather startling.

Sombra is in a dress.

He says he can explain.

How could this possibly go...?

Cover art is a cropped edit from an Evehly (link) comic. Contribute to the TVTropes page! Reading of the old version by Lotus Moon! Recommended by PresentPerfect!

Published 2017-12-14 23:50:13 UTC
Last updated 2017-12-14 23:50:13 UTC

Fancy Demons, Confused Goddesses

"Sombra?" I called. The werelight that was budding on my horn glowing with a soft bluish-white light. It cast a soft illumination on my immediate surroundings. I had never minded the usual lower light of his pocket realm; it felt like a dim study on a rainy day, when soft sunlight only glanced upon the windows.

Most of his things were very spread out, like a strange variety of underbrush or sculpted... things. An exact definition currently escaped me as I poked my way around the familiar space, wings flared laxly.

He lacked any truly ornamental items and kept few things that could be deemed worldly and were outside his passions and various interests. If something struck Sombra's curiosity, he would have it as long as he sees himself as able to obtain it. Anything lying about was peculiar, pragmatic, but still personal. The frame-less mattress that did its job, stacks of spare books, a sheathed sword against a box of curiosities, and the bookshelf substitutes of short and tree-like gray crystalline material that shone somberly under my werelight. They were lined with some of the hundreds of books that Sombra had obtained. In the times when he adjusted the light levels to something darker, their contorted shadows awed me, for they were eerie and I loved them.

Sombra wasn't out, I knew that much. Yesterday afternoon, I wrote to him, as I often did while having to suffer through a most annoying petitioner that Tia indulged her time in like some petty glutton indulges in pastries. 'Twas obnoxious to listen to. Was it any wonder I scribbled short letters to him instead, slipping them into a small canister of dragonfire and expertly hiding my smile when I withdrew his replies? Even if some did not make me smile in full, I know there was light in my eyes my sister did not catch as she bid her sycophant to speak on.

In his letters, he made it clear that he would be remaining upon Canterhorn Mountain today as well. That meant that I could drop by whenever I wanted, as was our usual arrangement.

"Sombra, are you here?"

Pricking my ears forward, I listened for any indication that he was here. If not, I might have to visit our usual haunts around the city. Maybe he was at the vegan eatery off Mane Street? He loved bringing me there so we could get something to 'take out' before slipping off somewhere more remote. Might he even be browsing the underground remains of Canterlote, the city beneath a city where I once walked alongside that whelps that were the Founders? Sombra and I frequently had our own little adventures there, and hiked through many of the surrounding mountains.

Lifting my head, I furrowed my brow in thought while my mane bobbed with the movement of my gesture. Us not meeting at exact times was not much of a problem. Sombra and I usually just set general times of day — moonrise, noon, dusk, dawn. Though, on the clock times were not out of the question if needed.

The faintest rustle of fabric behind me caught my attention, and I whirled around to meet the source swiftly. Once a warrior, always a warrior, after all.

And I saw...

Shock spread across my face, my wings flared fully, and I prepared to have myself poised for any movement needed when my flurry of movement had ceased.

I reacted like this not because I was startled by Sombra — few actions of stealth could even shock me remotely. At times, he has simply been lurking about the farther reaches of this monochrome realm, minding his own business until I stumble upon him, and other times he shall surprise me.

I searched his eyes, meeting his dark pupils that now began to show concern, my own confusion apparent.

I swallowed visibly, my mind racing for how best to begin to word my reply.

Sombra arched an eyebrow, scarlet eyeshadow glittering in the flickering glow of my werelight. Even after it snuffed out, my aura ceasing, there was still an unmistakable aura of sass in the twinkling cosmetics of Sombra's smoky eye.

"What's wrong?" he asked, eyes roaming across me to look for any telltale signs of what bothered me specifically. He tilted his head to the side, his usually long, loose, and disheveled mane now was mostly pulled back from his face. The exception was for his bangs and a wave of his dark mane that fell to the side of his face.

"Som, why in Tartarus' name are you outfitted so?" Stars, I suppose that was the best I could come up with off the top of my head. Must I expect eloquence from myself on all occasions?

He lowered his ears slightly, taking in all my motions. While he still stood solidly, there was some hesitance to his posture. The hem of his elegant vibrant red cocktail dress swished faintly.

"You don't like it." It was a statement that held a question though it was not one.

I kicked a hoof, hearing my shoe strike the crystalline ground of this solitary plain. "I do not know..." I really couldn't take my eyes off of him. This was beyond his known eccentricities, to show up dressed so... how did he look to me? Feminine?

No, surprisingly that did not fit. Unusual? Oh, without a doubt, but Sombra was unusual.

Ceasing my descriptive verdict, I returned most of my focus to him.

"Sombra, where did you find these things? Were they crafted from your magic?" I asked, eyeing the way his gown was slit up the side, revealing hints of his scruffy coat and traces of scars on his hindquarters. The way it clung to his form so well was commendable, but still deeply confusing. The whole atmosphere of what was supposed to be a regular visit — as regular as our dates get — had become something more anxious.

His fuzzy ears twitch curiously. "I made the dress; the cosmetics I stole."

Ah, there was no surprise there. "The dress is..."

Sombra arched an eyebrow expectantly, tapping a hoof a couple of times while waiting. They were devoid of his usual metal boots. "I'm waiting."

My eyes found the floor.

I listened to a couple of beats of my heart.

I tried to untangle imaginary knots in my tongue.

I let my wings drop.

The echo of an unfinished sentence starting and consisting only of 'I...' rang in my ears. All I did was register my own voice. Words died clogged in my throat, locked in half-finished variations of what I felt I must convey and...

I just felt Sombra's magic carefully levitate me off the ground, a startled squeak escaped me. Then, he levitated his swivel chair over, promptly placing me upon its seat.

"Tell me what's wrong." He spoke firmly but did not command me. He never commanded me, and for that, I would always be glad.

"This... This does not feel like you." My voice was even enough, but I could not meet his eyes when I said it.

Stars, I even felt how worried he was. Sombra lit his horn with a softer crimson light and ran it through his mane, pulling out the hidden clips that had skillfully held it in place and letting the sleek dark locks fall into their usual place. Quickly reaching up with his forehoof he mussed his mane a bit more so that it was back to its more familiar state of dishevelment.

I swallowed again, my throat feeling much tighter, and I still did not dare to meet his gaze. "I'm sorry."

"Luna—"

"I should not have said that." Now, I speak into my forehooves. I have not locked up like this around him for almost a year, when he and I were still figuring things out. Because of him, I have locked up less and less even around others. "It was cruel of me, but I knew not what else I could say to you... seeing you like that, dressed..." What could I say now? I needed something true.

While Sombra gives me the silence I need, he tries to help. I listen carefully as he supplies a suggestion for me. "...Like a mare?"

"Y-yes, like a mare. A mare in a cocktail dress."

"Ball gowns aren't really my style," he says, resting a forehoof on mine.

I nod quietly. No matter the circumstances, I cannot imagine Sombra wearing a ballgown either. The weight of his forehoof on mine is just so grounding, and I could ask for no better help to ease my thoughts in a better direction.

"I still need something I have a chance of fighting in," he pauses to gently pry one hoof away from my face, and only because he knows that I will let him, "as well as look stunning in at the same time."

'Stunning' is certainly a good word for this.

His eyes aren't angry, but Sombra is so rarely irate with me. I stare quietly back at him, lowering my other foreleg.

"Sorry," I whisper.

He frowns a little and rolls his eyes, patting my forelock a bit brusquely. Though, his care for me was still apparent as his words were blunt. "Stop apologizing. I understand why you feel like this, and I can explain. While I'm all for marveling over myself, we're going to have to pass on that for now. This is... not the kind of attention I like. Even from you."

Sombra promptly sat on the ground, the vivid red of his skirt flaring around him like the petals of a poppy flower against the gray of everything else. The sight was striking as a drop of new blood on the freshest of fallen snow. He looks up at me with a steady gaze, no doubt knowing his own loveliness.

"Ask me any question on the matter, and I'll answer honestly," he says, cutting right to the point. "I'll have a few for you later."

Drawing in a deep breath, I pulled a clear question from my mind. Now that the storm of thoughts I had before was settled, I think I could pave a direction for my part of the conversation. "Do you... like wearing a dress?"

Sombra was unfazed by my awkward tone and looked at me with what could be mistaken for indifference. "No, Luna, I'm wearing this because I fancy that I appear like a sack of radishes and am just as appealing."

Ah, so he likes it quite a lot, then. To communicate our newfound understanding of that particular aspect of this whole ordeal, I punched Sombra's withers. In doing so, I was rewarded with something between a murp and a tch of acknowledgment.

I smiled briefly before asking, "How long have you... been up to this? Crossdressing, that is." The second bit I had added rather awkwardly. Hurrah, hurrah. It appears there are still times when newfound confidence can falter still.

He just shrugged with an odd air of glamour, unaffected, apathetic, or perhaps a bit of both. "It's hardly 'crossdressing' to me. Clothes are mostly just clothes. I discovered that with a few charms, an incomplete glamour, and small appearance modifying spells, I can get fairly far. When I use my magic to alter my vocal range enough I have passed well enough as... definitely not a stallion. Despite my build, whenever I needed to go unnoticed for lengths of time, this was enough to keep prying eyes away. Who would ever be looking for a mare when they intend to find me?"

"How clever of you." I shot him a smile and watched as Sombra puffed out his chest a bit, pridefully enjoying every little compliment I had to bestow.

"Do you really expect anything less from the Right-Honourable Lord Sombra?"

It took me a moment to realize that I wasn't sure if I should be referring to Sombra as male right now. Yet, Sombra had just called himself 'Lord' once again, however facetiously the intent was. I couldn't get the association between my Sombra as a stallion out of my mind right now. Surely until Sombra said otherwise or corrected me, there would be no issue to have my thoughts remain as they are?

"No, of course not," I murmured, reaching out to stroke his mane. A soft purr rumbled in his throat before he batted my forehoof away with one of his own, much to my surprise. He loved to have his mane stroked, twirled, braided, toyed with — he even allowed me to curl it once!

Why would he do this?

Noting my confusion, Sombra raised an eyebrow. "Can I continue?"

Nodding quietly, I let him. Getting to toy with Sombra's mane always reassured me in times of anxiety, but if he needed otherwise, I wouldn't dare impose.

With a flick of his aura, Sombra flipped a stray strand of his mane back in place. "Good. As I had been telling you, it originally began when I needed a convincing and unexpected disguise. I'm not a damned love-sucking parasite, so I can't shapeshift."

"But you are clever, Som," I said, poking his muzzle and enjoying the grumpy look he gave me. 'Can I finish?' his eyes asked.

So, I let him, wondering all the while what he had left to say. My anxiousness had abated enough, but I knew some lingered.

Another roll of his eyes."Finally. To 'crossdress' as you and everypony else has been calling it was my first choice. Ponies would look for somepony they always imagined as a stallion, and one with eleven centuries of history allegedly unknown to them. So, in the eyes of all mere mortals, I'd be a fool."

He laughed scornfully. "The whole lot of them are a bunch of bloody fools, these modern Equestrians, aren't they?"

I shrugged. "They do not burn prodigious young mares at the stake any longer. Surely, that is a slight improvement by your standards?"

"So I've observed," he mumbled, twirling a bit of his mane in his magic with cool nonchalance. "There's also a surprising lack of 'undesirable' infants being left to the snow."

"That is one of the results of my sister and I ruling, yes." I dared to stroke his mane again, and he permitted it for a short while.

"I really don't get it."

Confused by his response, I looked at Sombra, eyeing him with a questioning tilt of my head. "You do not understand what, dear Sombra?"

He waves one forehoof in a short circle rather aimlessly. "The whole ordeal with clothes. There's hardly any that need to be exclusive for mares and stallions, yet there's still some hold over the notion. Anypony can wear a suit or dress, though it's obvious that some clothes are universally ugly. Ballgowns. Nearly anything with an excessive amount of ruffles. Why do those still exist? At least corsets were done away with!"

His eyes meet mine more directly, and when I offer no answer, he accepts my silent indication for him to continue.

"I never had that boundary, and I don't think it ended with clothes. I've been around mortals too much at this point to still be thinking it's just clothes." He shrugs again, toying with a bit of his mane in his crimson aura. Sombra was flicking it about in a way that made me actively have to resist wanting to run my hooves through it myself. "Wearing a dress was only odd at first was because I hadn't done it before. Wasn't it the same with you? You were the warrior mare in the time of the tribes. Didn't any aspect of your actions and how you presented yourself feel strange at first?"

While awaiting my answer, Sombra cocked his head to the side, and regarded me carefully.

I swallowed. The roles I held across history were often made marginal compared to Celestia's, and all without my say in the matter. Of course, some were wiped away in the minds of many from more than the passing of time. Mortal records of history saw fit to lay its gaze upon many creatures, and for the longest time, I was never one of them.

Nopony in the modern age would know this. The flexibility of gender roles began around Discord's rule, enabling mares to become warriors and other professions once more. Though, none truly grasped what they were doing in that era save reintroducing equality that the pre-Collapse had always had, and many other nations never lost. The prejudice of the Tribal Era ponies had slain many good ideals for a time, and Equestrians were still a very different kind of pony compared to those in other nations.

But in the Unicorn Tribe's society, I stood out worse than a sore hoof. My mane was cut in something like the modern bob — one that Twilight Sparkle and the other Bearers observed my mane upon my return. For them, it was not a source of gossip or an oddity in this age.

Tia was closer to the feminine ideal of the unicorns. Her long tresses were maintained almost constantly, and her mane complemented by smaller braids within it and circlets atop her head. She always wore the latest gowns — ones with sleeves that were always long, and sometimes flaring out. I remember how she had such long, layered skirts that hid her legs, drew a modest amount of attention to some of her chubby form. The way they dragged upon the ground had led to far too many annoyances. The posterior that stallions drew too much attention to was hidden within all the petticoats. I had to sit through too many of her one-sided 'mare-talk' rants about how she either loved or loathed that feature.

I had wanted no such stiff and ornate fabrics for myself. Even as an adolescent, I knew that to don such garb was to encase myself in a cloth prison. Fur cloaks, hide boots, and short cut-tails became my attire. The scabbard and sabaton were my accessories. My forelock grew into an extended version of my bangs, but not the one that hid a mare's face like a veil as Tia had hers — something that would be seen as a sign of modesty. I had to scavenge for armor from fallen pegasi to allow my wings the freedom they needed as Tia cut slits into her gowns.

She had always had a girlish fancy for the less-lethal of the cosmetics favored by the unicorns. For that I am thankful. My sister was smart enough to not wear the powders with lead, which ate the faces of some noblemares away. Though, I only wore dark paint around my eyes to offer some kind of 'mask' against snowblindness. It used to make it slightly more difficult to peg down who I was, despite my wings and horn. The paint ran like a punk-filly's eyeshadow of today, and some feared the wild look it gave me.

...Had any of that ever felt wrong? I was faced with slander, of course. No matter how it hurt, I braced myself. I knew those ponies were wrong. Of course, some days it had hurt more than others. They thought me mad and said that I wanted to be a stallion. Thus, I had been considered the world's first known crossdresser. Except, I really had not been, not as ponies thought I was. Then, I was also a monster — to wear fur as I did, brazenly and openly without tailoring it to something 'elegant' was only a taboo. It was hardly different than how wearing fur today was considered murder and desecration. Though, I was not a monster any more than I was a 'false-stallion' as they had called it. Always, I had known I was a mare — and a strong one!

"No, Sombra," I said, fiddling with my mane, "it was nothing like that for me, but the taunts could dig deep sometimes...." I sighed, "...and occasionally, they could be quite crass. Still, I felt no oddity in such an action. I only did what I wanted and had to in order to secure my freedom... but I never stopped thinking I was a mare."

"I don't think I'm a mare," Sombra said, flicking an ear.

"I'm sorry," I said, sighing and stroking his mane again. "I still do not understand why you do this. To me, you have always been a stallion. I just don't know how to ask you if you aren't. Does it bother you when I call you such? "

Trilling a little in his throat, Sombra arched an eyebrow. "I think that when you do that, you're the only one that I don’t feel bothered by. When you call me masculine things, it doesn't feel like you're imposing anything on me... or my body. Nopony else has ever asked me what I am before, and I don’t think anypony buy you would show me acceptance for something like that.”

"Oh Som," I murmured, "you say that you don't mind if I address you like the way I would I male, but are you a stallion?"

Sombra hung his head — and the gesture cut itself into my memory sharply, for it lasted only a moment. "I don't get how ponies and Alicorns have those differences. I don't understand why I'm the only species that have these feelings written into me like I'm the one who is wrong for being different."

Blinking, I just opted to pat him on the head again. "I know that, Som... I just always knew you to be rugged, handsome, and roguish, and your flamboyant side feels like a mere 'streak' in comparison, yes?"

He narrowed his eyes, examining me carefully, and I withdrew my forehoof, wondering what was going on in his mind.

"Are you implying that I'm somehow not handsome right now?" An irritated flick of his ear followed.

"I..."

Oh...

My horn is illuminated once more, and I quickly lift Sombra into the air before resting him in front of me, so we share his swivel chair. Pulling him into a big hug, I ensure I wrap my forelegs around him as tightly as possible, feeling his fuzzy coat, the silky fabric of his dress, and planting a kiss on his cheek before I shifted myself; resting my muzzle on his wither and nuzzling into his mane.

"You have always been exceptionally handsome, Sombra."

I'm just not sure if you're a handsome stallion.

"Even when I'm in a dress?" he ventures slyly, the smirk in his voice oh-so-obvious.

Sighing, I nuzzle him gently, all of my words spoken into his coat. "I... I still find you..."

Instead of listening to how my words trailed off, I simply buried my face into Sombra's mane. Doing so I meant that I could lean forward so that I could make a clumsy attempt to hide under it. He let me, but not without a small murp of surprise.

Do I still think Sombra is handsome and attractive? He wore a dress that even I would not ever wish to wear, as any mare would.

The last time I wore one was a gown for Twilight Sparkle's coronation. My sister had gotten it for me, to match some trinkets. I hadn't liked it at all, and had grumbled quite thoroughly to Tia about how I would be unable to fight in such formal wear, if the need arose. She simply doesn't understand the need for being able to move and sit properly.

Conversational jokes about dresses no longer having cage crinolines — a horror I never had to witness — did little to distract me. Even to this day, I cannot understand how I did not pout through the entire thing.

To say that the feminine dress was 'not my style' was a great understatement. Fine suits, cut for stallions and mares alike, and other kinds of attire I certainly had a fancy for, though. Just as I preferred the less-than-traditional feminine things for myself, I liked it in others too. Sombra's ruggedness and flamboyance were balanced well, and he was strong of will and mind. He was not a soft kind of mare. Even my dear friend Cadance had a good, lively spirit and the ability to fight well. That was something I did not see in the more conventional image of my sister, her student, and a good few of Twilight Sparkle's friends.

None of that made those ponies less of mares. It certainly didn't make me less of one.

Sombra, however, was such an odd case. As a genderless demon, he only was what his form was. There was no gender barrier to him.

I liked that notion.

...And I liked Sombra too, dress and all... I think.

"Yes, Sombra," I said, a light laugh infecting my words, "You are quite... alluring... even in your dress."

His prideful, warm trill was certainly worth all my words and adoration. Such a demanding demon I was stuck with! He was mad enough to make me think a stallion in a dress charming with all his wicked wiles.

"Though, I wonder, Sombra, if this has to do anything with... the status you have."

I feel nothing but a sense of wrongness calling him a demon and the slurs associated with it. The alternatives still came out a tad bit awkward, and were often worse. He knew what they meant, either way. I was thee exception to so many of his rules, preferences, and general aspects of his nature. If it were not such a creepy idea, I am certain that many others would think that we constantly read the minds of one another.

His horn brushes against mine. I shiver when I feel the movement and unmistakable presence of aura on it. He teleports us both to his pocket realm's ground, where we still embrace one another. I catch him mumbling about how the chair would eventually break under our shared weight.

I did not disagree.

Eventually, we manage to peel ourselves out of the other's hooves. I rest my head upon his wither, wrapping one wing around him.

"Honestly, Luna? It probably does have something to do with it; I don't care if it does. This is a fine dress too," he grumbles, "and I look pretty damn good in it. I'm not going to toss it."

Chuckling, I levitate a strand of his mane away from my muzzle. "If you look so good in a dress, do you think simply anypony could?"

I felt him shrug. "Somepony else could look good, yes. Mares look okay in dresses. Stallions certainly look pretty fine in them. Suits are sharp on both. So, of course somepony else is going to look good..." He jabbed my wither with his forehoof, getting a small startled noise out of me. "They just won't look as good as me."

I punch his withers back, only for him to roll his eyes as I would expect him to, never seeming to fully grasp the gesture.

Peering closely at him, I tilt Sombra's muzzle toward mine. He looks at me patiently, waiting for me to speak whatever has perplexed me, and I am greatly perplexed.

"Sombra?"

He raises an eyebrow. "Yes?"

"All this explains the dress very well, though there is still one big question that is perhaps more urgent than that, ah, pressing matter."

"And it is?"

"How and where did you ever learn to do your eyeshadow so well?!"

Author's Note

A little ficlet about the OTP being nutty and Sombra giving fuck all about gender norms, since being a genderless demon does that to you. Literally wholesome crossdressing/gender feels and also cuddles.

[Revised and updated for print on 11/29/2020 and made Sombra being trans more obvious even if No Specific Gender is said yet]
[Updated one final time on 12/18/2020]