Endeavors of the Enigmatic and Eccentric

by Ice Star

Boyfriend Lipstick [Drama] [Q]

Author's Note:

Boyfriend Lipstick

SOMBRA IS PRETTY PLEASE HELP ME.

(Also, a small note: drag queens reading stories to kids is a real thing.) 'Urban decay' is also a real lipstick shade.

Some inspirations and refs (all are SFW derpi images, I'm just too lazy to link them): 1613243, 854154, 1674772, 1602965, 1622259, and 1588148. This is sort of a bizarre interquel to Dressed to Impress and its sequel, and follows the theme of this anthology not using the clearest and most defined part of the timeline. Instead, it uses the murky year between the end of Favorable Alignment and before Enemy of Mine and further chronicles the time period Luna and Sombra spend dating, as this cluster of stories and anthology does. Sometimes words must flow, so here's a just for fun thing with some queer themes. The canon of this is mostly dubious, at least, because Dressed to Impress turned out so well... so I'm not sure? This just kinda happened? I wanted to expand on what I did, and offer some more... and this is the result.

"Which do you think would look better?" Sombra asks, holding two tubes of lipstick in his magic. The label on one simply reads 'scarlet' and the other is something bizarre labelled 'urban decay' and reminded me why I do not delve into cosmetics as deeply as my lover.

My muzzle crinkles in thought, and I try to sneak a peek at Sombra's outfit as subtly as possible for a comparison. He was wearing a fashionably cut sundress with a plain sash and faintly ruffled hem, and while it was quite nice I was not as drawn to it as he.

The straps rubbed the coat around his withers in such a way to make it extra scruffy in a way he would never admit was adorable, but did not chafe his coat like the dreadful fishnets I had him try one time, only to regret it when I had seen his displeasure. He has such a better eye for these sorts of styles beyond just describing them and quietly sorting them as feminine as I do. If I did these things with anypony else, I think I would wonder if there was something wrong with me.

Everything I suggest just seems so grossly exaggerated compared to what he wants to wear, and something embarrassing just happened every time we had a mishap. It felt like a little bit of it was my fault.

So I tried to look at his skirt carefully, for some secret of high-femininity to be revealed to me as it was to other mares, one that could help me select the proper kind of lipstick for my boyfriend. The pale shade of butterscotch merely continued to appear delicate and pastel. When his coat was colored a little differently for going out today, it would look even better.

I tried to think of this being like a painting, and I needed to just pick the next color, but all my mind did was remind me that I was selecting lipstick and this became infinitely more puzzling.

Should this not be fairly easy? He wanted to look pretty, he was already so pretty, and he made me feel beautiful for who I was.

But there was something complicated in all this, wasn't there?

Eventually, I thrust a forehoof toward his scarlet tube of lipstick. "This one looks a bit bolder, I think."

And really, I did think so, I just wasn't sure I was certain about it.

...

Sombra scrutinized his reflection carefully. His critical eye examined every inch of himself in the mirror he kept, and while the gray of his pocket realm was visible in the background, Sombra was the absolute star of all that was shone in his mirror.

I sat quietly next to him, only visible because I bothered to lean over and peer into the shining surface. I was faced with the frank sight of my owlish stare, and how my mane rippled and sparkled with an air of clear curiosity. My dark tiara and necklace were in place for now, but I was prepared to exchange all my regalia for more suitable apparel for a disguised date.

Sombra decided that today was a day to dress as a mare for such an occasion, and something about his dress wasn't satisfying him. I was not sure what it was, for at first glance it appeared to be fine, but Sombra's horn was lit steadily and he tugged at it.

The fabric of minidress was a bit tight, but I think that was how they were supposed to be. I would not be able to stand wearing such a thing, but Sombra wanted to. The low-cut wine colored fabric gave a wide view of his withers and clung to his hips and sides. He had told me that he had to get it custom made because there were places on a mare's garment that should be tight that a stallion would not desire. To me, that was immensely understandable, if for different reasons.

I think I liked that he chose to have the skirt longer than most dresses of its kind. Som loves long, flowing skirts dearly, so something more akin to a pencil skirt - that was what Cadance said they were called - was an odd sight to see on him. While the way that it clung to him made it very clear he was no mare, and could not pass for one all that well, he did look very charming.

I continued to quietly watch as he tugged at the smooth fabric, adjusting it near his hips so it did not wrinkle. His jaw, his hips, and other signs made it so obvious that he wasn't a mare, and I liked them. A lot.

His horn dimmed and he cocked his head to the side, eyes still trained on himself. I scooted closer to him, and gently laid a hoof on his wither. He flinched slightly, and I caught a glimpse of momentary surprise in his eyes, even if all the glittery eyeshadow he had on might be distracting, it couldn't take away the constant allure of his eyes.

"It's just me," I assured him, and he gave a slight nod, looking down slightly.

"I know, I-"

"Shh, it still happens sometimes. I understand that, but what I hope you understand is that I would adore doing your mane."

He turned his head and looked at me quickly, any hint of momentary worry gone and his ears perked with interest. His mauve lipstick made his odd, tiny frown of latent interest - a subtle quirk only I knew how to read on him - all the more cute, in a weirdly reassuring sort of way. I think this would go okay.

"Do you want to braid it?" he asks, quickly running his magic through the usual disheveled locks.

I nod eagerly, reaching up to stroke it absentmindedly. With how close we are, the smell of his shampoo is strong, and it has the aroma that I've come to understand is more strongly associated with stallion's mane care products - and expensive ones at that. There was the faint hint of mint in the air, along with the usual smell of wind, warmth, and wild places he carried.

Sombra clearing his throat was what pulled me from my happiness and made me realize that I had wrapped my forelegs around his neck and pulled him into a hug, my cheek casually pressed into his chest fluff that on some occasions maybe did look a little goofy.

"For the mare who is cruel enough to constantly accuse me of being a 'cuddlebug', you're being awfully huggy."

"Mmph," I protested.

"No," he scoffed, "of course I'm not complaining."

Being turned away from the mirror meant that Sombra saw a reflection of my mane, and thus missed the roll of my eyes. "Mmph mmh."

"Get your face out of my coat and say that to my face like a real mare." Sombra pulled me off of him with his magic brusquely, but not cruelly, and he glared at me without any genuine irritation.

I looked at his reflection again, watching his tail flick back and forth. "You really do love to be spoiled though, don't you?"

Sombra grumbled something I couldn't catch and was poor at pretending he didn't see the faint coloring of his own cheeks in the mirror.

"You're going to have to speak up," I whispered into his ear, and watching as he grouchily flicked it as my breath met it. I settled back down to where I was, giggling into a forehoof while he sighed.

"Maybe," he grumbled, sitting down with careful grumpiness and a glamorous wink at his reflection.

He let my magic tease a lock of his mane and accepted the signal to scoot closer to me. I began to hum as I combed through the dark hairs in order to make a proper braid while Sombra observed everything.

"What are you doing differently?"

My humming ceased. "Whatever do you mean, Som?"

"The way you're moving my mane is different this time. I think it's obvious you're going to be doing something differently too."

I smiled down at him. "I was thinking that a single Prancian braid would be nice. It would give your mane a nice wave when we take it out. Would you like that?" My magic moved down, ruffling his bangs teasingly. "I'll leave these as you like them."

This must have meant more to him than I thought, because after a brief silence, he answered me. "Yeah," Sombra said softly, searching his reflection for something I hoped he found, though I know not what it was, "I would like that a lot."

"Well, huzzah! That will be splendid, because after so many years of knowing these terribly ancient beauty secrets-" I winked at him "-I would love to do this for you."

He smiled at our reflection, but there was something unsure in his eyes. "Where did you learn to do this?"

"My sister," I replied, gathering more of his mane. There was something about stallions who kept their mane long that was enticing, and Sombra's was absolutely divine. Long manes on stallions and mares, and short coltish looks on mares were fine things. "She loved all things beauty as a a filly, or at least what she knew. As fillies, before all our travels, she would always want to play together. Now, I loved playing with her, but she only ever wanted to play together, not alone, and to play alone was so much more fun to me. She had whole hosts of dolls, dresses, tea sets, and such but made me her favorite. I was her daughter in every game of house and her dress-up baby before, when I was too young to protest, and everything else she sought to control in our games."

"That sounds like an incredibly one sided game," Sombra says, frowning in thought. I shall probably have to explain to him what things like 'house' are some other time, because I don't think he would know.

"They often could be, but hardly in any offensive way. She ruled, and wanted me to follow because I was the little sister. I didn't like having our mother's make up on me in excess, or dressed up in her dolls' clothes, and my mane styled every possible way, but it never hurt. Maybe there were times when my pride was wounded from awkwardness, but nothing else. Growing older was much more fun because then I finally got to be things I was more comfortable with. Those things were much more interesting, like being the knight to her queen. But it is because of her that I learned many things about beauty beyond the extent of which I would have normally thought to look into. She helped there just as much as she buys me admittedly embarrassing dresses to wear to galas and coronations."

And I would have given you those dresses if any of us had actually liked them and I really thought that they should be worn by anypony.

Sombra's braid was coming along well. He was so eager to watch my movements, to listen to what I had to say, and...

I love him. Poets spend lifetimes writing of love, philosophers war over matters of the heart, and here I am, having watched and read so much of it, but I just collect every little thing about being in love with him and cherish it.

I want me braiding his mane today to be a way that I tell him I love him, and I want him to know that. I have these peculiar doubts that I must ruminate on, and these complications all regarding a dress, and him, and all of it together and I must say them right. I don't want to say them, but I will have to. I don't want to talk about these things, not now when we have a date.

When his braid and done, and house is explained, and we've had more words to share, I make the extra effort to show Sombra himself in the mirror. I know it is always him because... well, Sombra is male. He never asks to be called otherwise, he gets confused when he is, and yet he doesn't quite correct anypony. I think I should understand this by now, about him and his dresses, but I do not, not fully. I don't know why. I always have questions I do not know how to ask him, or if I should.

What I do know is that sometimes, when he decides to dress like this, and is disguised properly, ponies will look at me with something like disgust when I refer to Sombra as male.

But right now, I really do try not to worry about that, and I get to see his expression. Now that I've finished, his bangs are slightly adjusted so the disheveled part of his mane covers one eye a bit more than the other, and his thick mane is in a fine Prancian braid.

He's smiling his crooked smile at the sight and his eyes look happy. And yet, that makes me feel rather crumpled inside, because I know that this isn't unhealthy, not in the slightest. But in all this, I'm missing something. I've been missing something about this, though Sombra has been wonderful enough to explain all to be, and I still don't understand something.

I'm missing something, and my emotions are rather... haphazard, I would say.

But stars, he looks pleased and confident. He even leans over to give his reflection a big kiss that leaves a clear lipstick imprint on the mirror.

He pulls away from the surface, giving an extremely satisfied look to his reflection, a lazy smirk on his face, and his lipstick in need of touching up. "I'm certainly looking forward to tonight, especially when I look like this. Are you ready to leave?"

I nod, knowing we can work on our disguises on the way without notice. "You're going to have the attention of everypony at the symphony."

"I'd rather have your undivided attention." The way he's watching me so calmly in the mirror, his stare so reasonable and sharp makes me think that he suspects something.

He can't know, can he?

...

"I truly doubt that I can pull this off properly," Sombra grumbles. He looks tired, or perhaps just dissatisfied behind his sharp cat-eye glasses, and ones he doesn't really need. He teases his messy mane once and lets his aura fidget with his pearl necklace freely. "And I can pull most things off. But a secretary?"

He shakes his head at the sight of his pencil skirt. "As much as I like my own butt, there's something dreadfully underwhelming about this costume. I just don't like it."

"Well," I said, watching him inspect the red blouse that he seemed to have moderate satisfaction with, "I thought that if we were going to do couple's Nightmare Night costumes, we should go as something with clothes we like. I would be the businesspony and you would be my secretary."

"Secretaries aren't even intimidating, and isn't that half of what the costumes are supposed to be?"

I looked at my own sharp suit in the mirror, and how it contrasted with my ceremonial cuff links and the tacky tie I had selected. I thought the goldfish pattern had some merit to in it, in a goofy and foalish sort of way that would appeal to the holiday, but my diva of a lover was quick to deem it tacky, though I didn't mind."That is half of it, but dressing up in disguise as something you are not is the other half, and you are certainly not like any secretary I have met. My sister's secretary is a gossipy, meek, and obsessive little mare and it seems that some of her habits are a bit of a trend in the profession. I thought you might wish to wear the dress."

Had I gotten it wrong? I would love to see how handsome Sombra would look in a suit for this, and a more conservative and practical secretary costume would be one I would enjoy pulling off, even if it did have a little skirt. A longer one could be substituted, if I wished it. But had I been wrong? Did Sombra not want to wear mare's clothing this time? Was I being presumptive? Or pressuring him?

He flipped the collar of the crimson shirt up. "The blouse is very nice, though. I really think we should try different costumes. This one really doesn't work, and I'm not sure I'm comfortable with it. What are Pink One and Glitter Sprinkle going as for this?" He toyed with the pearls some more, clearly intrigued by them. "I like this idea, the couple's costumes," he muttered. "It's... nice."

How romantic, I thought, knowing I might have something to tease Sombra about later.

"Cadance is going to be a cheerleader and Shining will be a hoofball player. He was the one who picked their costumes this year, going by those choices."

Sombra ran a forehoof through his mane. "Maybe we should do something equally plain then?"

"Perhaps we could. What did you have in mind?"

Sombra smirked, approaching me for the sole purpose of winding one of his forehooves into my mane and nibbling at my ear flirtatiously, and wrapping one forehoof around my withers. It was enough for me to see his telling smirk and the gleam in his eyes. These were the little signs that told me he liked how I smiled back, and every little reaction I had. His breath was warm on my ear, and I could feel him purr with the gesture.

"I was thinking," he whispered, "that we go as the handsome rogue and the clever maiden he loves so dearly."

"With pleasure," I said, laughing happily and nuzzling him. "I would adore it!"

We were already those things, to some degree, but we loved getting a chance amuse one another with those roles in more lighthearted, purely affectionate, and rather romanticized ways compared to how we really were.

And I really would adore it if the mood was right. The thought of Sombra and I dressed up as we chose and getting to indulge in affection and banter with one another so cleverly was exciting, and we were good actors, too. This lead to such sweet fun.

He happily returned the nuzzle and I was already imagining how he might look. With careful telekinesis, I pried off his sunglasses and kissed him right below the horn. There was a terrible inequality between a secretary and their employer, too, and it was not a status that held any joy, even in jest. On the other hoof, there was too much fun to be had when teasing one another so had roots in our natural behaviors.

"Enough with a secretary's guise then, Sombra. I want you to surprise me with what you pick. Cady and Shining will probably find our costumes underwhelming, but I think it will be splendid! Can I help with your mane?"

Sombra chuckled warmly and nuzzled into my mane. "Of course you can. Who else could I possibly consider?"

"Mhm, perhaps Cady? She taught you far too much about cosmetics-"

"Are you implying that my skills are dangerous?"

"Aye, they are as dangerous as your ability with spell and sword, Sombra," I said, gently guiding his forehoof from my mane with my own.

I looked into his eyes and knew that my words meant much more than I thought to him. Something very warm shone and grateful showed in his eyes.

I felt a bit guilty because of it. This was something that mattered to him, something secret that only I knew the extent of and Cady some of, and yet I was unable to understand something so fundamental about this.

I would tell him one day, for the sake of both of us.

...

My mane spilled out beneath me and I sighed contentedly, enjoying the sensation of the firm ground against my back. Grass brushed my coat and feathers, and the fresh air of the mountains was in my lungs, a scent that was familiar, crisp, and clear.

And the best part? It was just Sombra and I sprawled on this area of the Canterhorn, where we could laze above Canterlot and enjoy the peace of this place.

I was absorbed in the sight of the clouds and all their details as they floated across a vivid blue sky. They were large, thick, and silvery things that would be delightful to dip my feathers into.

My only interruption was when I heard the rustle of paper, and the thud of something being thrown. The impact of something against the nearby grass surprised me, and I swiftly sat up to see what it was, my mane rippling quickly. Like my ears, it flicked with interest, and I saw what had been tossed to me.

It was a newspaper. One of the page's corners had been folded purposely, though the paper itself was turned to the cover. The headline made it clear that of the capital's many newspapers, this one was Galloping Gazette, and one of the few I've known Sombra to read. He actively avoided getting much in terms of information from The Celestial Equestrian and The Canterlot Chronicle. There certainly were some present biases within those two, but he was quick to pick up the Gazette, which tended to just report on societal topics quite frankly, without needless equine interest stories shoved in to generate interest. Such a pragmatic paper was suitable for my pragmatic lover.

I scooped it up with my magic and flipped past the first few stories until I came to where Sombra folded the page. I quickly looked over the large photograph I was greeted with. Like many newspapers in Equestria, whether this one would contain primarily colored photographs, monochrome ones, or general infographics and similar visuals was uncertain, since it was one of the few things every paper had some bias towards. One instead of all, depending on what was desired.

This particular paper had a large colored photograph, which was a bit uncommon. In it, a mare with a broad smile and exaggerated makeup was sitting in what was clearly the foal's section of a library. She wore fine gloves and clutched a picture book. Her mane was styled boldly and wild curls were every which way, and her glittery dress swept downward like a waterfall of sequins to where a cluster of foals sat around her.

I looked over to Sombra, who sat beneath a small tree, enjoying the shade. He was clad in his usual cloak and nothing more. Despite the peaceful shadows, his hood was drawn. Sombra looked quite comfortable, but raised an eyebrow when he noted that I was watching him.

"Did you read the article?"

"Oh," I said, blowing a bit of my forelock out of my face. "I'm afraid I haven't."

He looked elsewhere, quickly finding something on the horizon to capture his attention. "It's interesting," Sombra said just loud enough for me to hear. "I thought you might like it."

I simply had to read it now, and dove into the article. The very headline I had so carelessly glanced over all but screamed about why Sombra was interested: these dramatic mares who outfitted themselves so notably were drag performers who dressed in finery the Canterlot elite found particularly trendy and entertained. In this instance, they read to foals throughout Canterlot at scheduled storytime events in libraries.

I admit, I probably should have paid greater attention to the details of this picture, but this mare did not look that unusual to me, and though I may be part of this sort of culture, I think, if only by some sort of technicality, I do not think I could be more greatly divorced from it, as I am from most things.

My only real exposure to these things are the confessions, revelations, and all the encouragement I offer to youth in their dreams over such matters. Quite a few have a favorite dragmare or stallion as an idol and are interested in this little subdivision of performing arts. Though, I do observe more than that on occasion. Sombra and I have our private celebrations of all these parts of identity, and it is impossible to avoid any of this in the era we live in. This is doubly true with Cadance as my friend and fellow princess, for she is just as excited for every June as she is each February.

"This whole event is rather sweet," I said, calling to him.

Sombra nodded, but looked distant. "I..." he trails off, gathering thoughts and playing with his tone carefully. "I like it too. The idea of these things..."

He trails off. Again. I frown. Rarely is he so reticent with me, and not like this.

"Som?" I probe gently.

His withers sag visibly despite his cloak. "...This appeals so much to me. The confidence, the boldness, the aesthetics... and I'll be damned if it can't be funny. Luna, I don't know how to tell you this..."

Sombra stopped, and swallowed. One of his ears flicked in frustration. "I don't know how to tell you this..."

He growled, lit his horn up with crimson, and teleported away. I know I didn't have to follow, that he needed time to sort things out, and that he needed this.

I didn't know something was bothering him so badly too.

But I didn't know how to respond.

...

I stared at the dress in the shop window. It was a canary and lilac sort of thing, and had the refinement I would expect from Canterlot tastes, but was also thoroughly unable to identify with. I would loathe to be in it, though loathe might be a bit strong, I would hardly enjoy the experience... as much as a mare I might be.

Sometimes things with Sombra made me wonder otherwise, but that only led to confusion and frustration at whatever this was. My identity was stable as well as familiar, and he was confident in his too... there were just communication issues.

Without any bother for elegance, I blew my bangs out of my face. My beloved blue mane had been exchanged for a cascade of darkish purple, one that hid a hint of sparkles of divinity that would not be easily hidden, and few, if any, would notice.

I looked very much the same too, for my eyes and coat were not exactly the subtlest guise, and my current mark may be fake, but was star related. My reflection confirmed this, and I continued to stand and stare curiously at the dress and ponyquin in the window with wide eyes. A walk in Canterlot was perfect for letting my thoughts stew and flow where they may, and nopony noticed me, so all was well.

I'm sure most thought me just another unicorn, and one that must be painfully average, as far as most residents of Canterlot go. I quietly enjoyed my unicorn disguise, for it was one I used when needed and felt like a comfortable extension of myself when I must use it at all.

The poster next to the ponyquin showed the Prancian-born model Fleur-de-Lis wearing the same type of dress in the boutique window. She was poised with the sort of cultured regality and dignity that was seeded so easily in Canterlot, but could appear a bit... stiff, in a way, like how any marble statue is still cold stone at every sunset, regardless of the wondrous detail and life of the carving.

Her and my sister were on the same sort of social circle form of acquaintanceship all the elite and royalty of Canterlot tended to have at some point, however brief. I spoke with her only a few times, because she was one of the few ponies that was interesting at the Gala, in the moments I bother to show up, and does not find the love of fencing we share to be 'unladylike' or unusual, and that is all I know of her. Her and her husband can prove socially exhausting, though I do not think they mean to be.

She is studded across so many beauty magazines, advertisement, and her name is frequently whispered at fashion events. Though, I only know most of this secondhoof. Twilight Sparkle's fiancée is knowledgeable on such matters, and though I am close to neither of them, I do hear most all that is sound around the castle.

I wonder what Sombra thinks of her, this mare who is such a conventional symbol of mortal beauty, and I know that is something I will have to ask him. I am sure he must have encountered the work she does in all his browsing of style.

I'm not sure I'll grasp it, how he has an interest in this and clearly something more, as well as all the other great passions and eccentric interests he has, shared or otherwise. I've learned to adore some of them, even if it is not as great as he, and we fuel something special by sharing them.

But I cannot dismiss this as a mere eccentricity. I am determined to know this as completely as I can, and support Sombra in something dear to him. This isn't what I thought it was, or whatever I am observing goes deeper than I thought.

Staring at this dress, and Fleur-de-Lis in her dainty gold jewelry doesn't give me much insight into anything feminine, and I feel deflated.

Sombra is not dainty, delicate, and he does not have this passive pastel pretentiousness some of these styles radiate, intentional or otherwise, even if he is in a dress. Sombra is alluring, he is bold... and wonderful. He is so terribly sassy and vivacious... and...

And I think I might understand this now, even a little. Perhaps.

There is nothing exaggerated about him in a way that feels purely for performance, though he has an honest sense of humor, even if it can be wicked. He does not do this to be sultry, though I'm sure there's something attractive about this to him...

I flick a few locks of my mane aside, and see a look of something brazen and hopeful on my face.

...

On a day when my confidence in myself is certain, I find Sombra halfway up my leisurely trek of Canterhorn Mountain. He stands aloofly, with a long, loose floral skirt billowing in the wind. His mane is teased by the breeze and his bangs fall freely into his eyes, but he looks at me with cool stoicism. The rest of his mane and tail have a few odd curls worked into their natural state, but he's tried pulling his mane up in a bun.

...And I actually rather like it.

"Hello, Sombra," I offer with cautious affection in my tone.

There is a sullen downward curl to his mouth. "Hello yourself," he mumbles, horn lit with a light amount of crimson aura and tugging at one of his curls.

The gesture is one that holds a terribly irresistible quality to it. I trot a few places closer, listening to the sound my shoes make in the grass.

"We need to talk." There, I have said all that must be said in order to begin this.

"I know," Sombra says, nodding towards a cluster of rocks where we might sit. "But you know that I wish we didn't have to."

I alight myself carefully upon a stone, and Sombra leans against one in his stubborn, nonchalant way, one that I'm much more used to than seeing the way the fabric of his off-wither shirt pressed against the gray of sun-touched stone. Despite everything, his shadow was a crooked constant, and his eyes were the same. I could never doubt those eyes.

"I do too, Sombra, though you know we must. Would you wish to start this off?"

"No," he says quickly and with an assurance I wish I had right now, "I need to hear what you have to say first, and I need to hear it badly."

"I'm sorry," I whisper. "I can't believe that we've told each other everything before, and we couldn't tell each other this."

"We will." He flicks an ear with a hint of impatience, but there's a much softer look in his eyes. "And we're going to do it now. For the mare who understands everything and more about me, I don't know what I did wrong that could make this so difficult."

I laid my ears back slowly and nodded sadly, rubbing one of my fetlocks against the stone's coarse surface idly and trying to avoid wincing. Or Sombra noticing. My throat feels tight with all this foolish, congesting guilt.

Scowling, Sombra snatches up my forehoof in his magic roughly enough to make me yelp. "Don't," he growls. "We're going to do this together, and what reason could either of us have to come out hurt?"

"I apologize," I whisper again, flinching at how breakable my voice sounds. And yet, aren't I as fragile as I am strong? And as wounded as I can be defensive, at least when I feel so scraped up by these silly mistakes?

Sombra teleports and reappears next to me. He adjusts himself so that we can sit wither to wither, but insists on wrapping a foreleg firmly around me and pulling me close.

Stars, I love this stallion.

"Luna, I want to know what's wrong. Grant me that, because this situation can go many ways, but it will not go away."

I...

"I can do this?"

I sounded far more unsure of myself than I meant to, which is terrible to think, since my self-esteem is awfully fragmented right now.

"I certainly think you can," Sombra says, and he turns to me just so he can place a kiss on my neck. I know the effort is meant to comfort me, and I truly feel more properly pieced together because of the effort... but there is lipstick in my coat.

Sombra got lipstick on my coat.

And I did something horrible by tensing when he did that, and twitching because of the imprint it left on my coat. Usually I have time to brace myself for when I came in contact with his lipstick so I would not hurt him by appearing uncomfortable. I would also wonder what was wrong with me and why the sensation of lipstick was so detestable to me when I should be savoring Sombra's affections.

I have to face Sombra because I hurt him. I look at him directly, and stare into the eyes of a stallion I've hurt so deeply because of one terrible reaction, and watch him swallow visibly. His eyes look damp because of what I've done, and all he does is watch me.

He watches me look away, and make a choked gasp. He watches tears blur my vision because the last thing I ever wanted to do was hurt him, but he refuses to let me hide my face behind my mane and forehooves.

I'm seized and pulled into a fierce hug, and one I keep telling myself I don't deserve throughout its duration. I know I should not think like that. I know I need to think about everything I can earn and do. I know I can't hurt myself by thinking about what I deserve, because then I really will hurt myself and every thought will be a Tantabus again, and I will keep telling myself that I must hurt myself because I deserve it.

I know I should listen to Sombra, because I have before for these things, and how we have extracted all catharsis and confessions from each other.

I know I should listen to Sombra right now because he is telling me that he loves me.

...

"Shall I begin?" I ask him softly. When we pulled away from each other, I found myself quickly absorbed with fidgeting with my mane, and twirling the thick, blue locks 'round my forehooves.

We still sat next to one another. To do so was instinct now, and we enjoyed being next to one another in calm content. I did not feel him lean against my wither today, and that was how I knew he was upset instead of seeking the peculiar solitude we could still share side-by-side when most ponies would want to spoil such tranquility with wasted words.

Sombra nodded with his usual assurance and melancholy both. It was a melancholy of character that he had, one of experience and reticence. He bore it well, and it was a facet of strength he had, but I was always saddened to see how it could flare when his mood was disturbed.

"I have finally found something about you that I struggle to understand, and it terrifies me." There. That was how I shall begin.

Sombra looks at me with distress in his eyes. "Luna..." he lowers his ears, "I don't know how to begin if that's how you-"

"Shh," I cooed softly, placing one forehoof to his muzzle delicately. "You do not have to say anything, remember? Not right now. I know you have much to say too, but may I continue?"

Him lightly cuffing my foreleg away was not a gesture I would find offensive, not from Sombra. He nodded, but emotion brewed so very strongly in his eyes, for he was ruminating.

"As soon as I knew you were a demon, I knew you were not like other stallions. You aren't grounded in what makes a pony a pony, and... a sliding spectrum of gender that other creatures fall under, you do not. And I have loved you no less for it."

There was a faint, thoughtful crinkle in Sombra's muzzle. "Is this about how I'm grouped in with transgender ponies?"

It was Sombra who came to me at times, confused as to why ponies kept referring to him as female, among other things when he went out, disguised and dressed up. I had to explain to him that these ponies thought he was a transgender mare, and were aiming to be respectful. Both were things Sombra was not used to. He only knew so much about the particular demographic of ponies because of my work with queer youth in dreams, and Cadance's work in matchmaking. Otherwise, he had little reason to acknowledge or look into these ponies as anything but just another demographic.

"...No, I do not think so. Maybe. Sombra, both you and I are queer, as separate as we are from everything that involves the culture. Your demisexuality and my asexuality count as as such, even if we don't count ourselves in."

Even if I've never come out to anypony other than him and Cadance, and how the same is true for him.

Sombra nodded in clear understanding despite how awkward I felt something about the atmosphere of our conversation was. Then, he laughed shortly and shrugged. "And here I can't help but love who I love. Though, I admit that having a name for it helps."

I couldn't say I was quite the same way. "Sombra... have you ever known any word that describes you beyond 'genderless'?"

"I can't say I have." He didn't ask a question, but his eyes gleamed with the question of what I might know.

So I told him: "Sombra, have you considered... that you might be agender?"

I watched how he grew serious again so quickly, and how reflective too. "Agender...? I..." I watched him swallow and grit his teeth. "I don't know... I'll have to think about it."

I smile calmly at Sombra and let my aura twirl one of his curls soothingly. "You have all the time in all worlds to think of anything, Sombra. I would hope that you spare me the wait of eternity for an answer."

"Luna?" Sombra asks when my toying is done, and there is a nervous flicker in his expression regardless of how steady his tone is.

"What is it, dear Som?"

"I don't think it would actually matter if I was agender and..."

"Som, it would matter to you. I'll love you always, regardless of who you are... but would you ever wish to be called anything different? To be addressed as female when you look so? Or as neither when you desire?"

"No, Luna, I'm male. Can't I continue?" The last three words hold the softest of growls.

"I apologize-"

"You don't need to," he says more levelly. The look he gives me next is direct and honest, an indicator that now he has something to say. "Do you hate it when I dress like this? I know I don't do it often, but it's been enough to lead to this."

And really, he doesn't do it often. Most of the time I am presented with Sombra clad in a masculine manner.

"There's nothing I could hate about you," I said, petting his mane and watching as Sombra flushed slightly. "Nothing," I repeat in a murmur, withdrawing my hoof.

Though we may sit apart, Sombra's forehoof finds mine and rests atop it now that my fidgeting is done.

I think I can continue more clearly now.

"You look beautiful, Sombra." I smiled when I saw how Sombra finally give a tiny smile, followed by a low, delighted trill.

There was still some color in his cheeks, too.

"And you know what, Sombra?" I ask him, running the barest touch of telekinesis on the fuzzy edge of his ear. "You always look beautiful, and I thought that me saying I didn't understand this would make you feel less beautiful."

Right when I need it, Sombra wraps a foreleg around my withers for support and pulls me close to him. "We could have talked about this sooner. I can look good in anything, if it really was a problem, and you matter more than any clothes."

"I know, and I really am sorry, Som. But you don't feel less pretty, do you?"

"Tartarus no. If even you think I'm gorgeous, what's the real problem?"

"I... I don't like the feeling of lipstick against my coat or lips, and I knew that telling you would upset you," I blurt. "That is one thing."

I watch Sombra's expression darken. "I'm far more upset that I have been putting you through something you aren't comfortable with."

The silence weighing atop us is suffocating.

"Luna?" Sombra asks, voice low.

The comforting presence of his foreleg now feels like a terrible yoke I cannot free myself from, and he's only pulled me closer to him.

Is it because he's upset?

"Yes, Sombra?"

"What would the rest be?"

Taking one deep breath, I found the words I must say. "I find your glamour to be confusing, though you've explained it to me before. I still feel like when I stumbled across you in your red dress because I have not stopped stumbling through my thoughts on this. As beautiful as you are, I don't know this part of you. I have helped you to find clothes you like, to do your mane, and work to understanding and embracing this because I love you. Instead, I don't think I came any closer."

I paused to look at Sombra, who eyed the grass rather forlornly. Before he could notice, I leaned close to his chest. His off-wither top allowed me to carefully tuck my head near his fluffy chest and to tuck my crest under his chin, nudging him a so a few times to comfort him before retreating to my previous position.

I was able to get a few faint rumbles out of him, the worn purr an acknowledgement of some level of emotional comfort.

"May I continue?"

Sombra nodded, then adjusted himself so that his head rested on my wither. I wanted to tell him that the style he did so carefully would now be disheveled now, and that he need not gravitate to me if he was upset with me. I was unable to find those words, and I knew Sombra didn't care. More importantly, I knew that if Sombra did not care, little could change his mind. Thus, the pleas to liberate my wither would not be heeded.

I sat still while he got comfortable, wishing that he had soft purrs, dry jokes, and inquisitive remarks to offer. The absence of these things were telling enough to how he was feeling.

He did not look to be in the mood to have his mane teased either, though I would have liked to play with his curls.

"When I think of you, some of what comes to mind is how handsome you are. I know most ponies say otherwise, but they have very poor judgement. I think of you as a very rugged, roguish, and... very, very dashing, in looks and heart alike."

I concentrated on the great mountains in the horizon to calm myself, finding my thoughts steadied by this. Sombra was the only stallion I had ever thought truly handsome and the sole one I have loved.

Truthfully, Sombra may look wonderful, but his personality was more handsome than the face he was so proud of.

"Sombra, I think of you as a stallion, not because you inherently are one, but because you make an effort to say that is who you are. What was I supposed to think when..." I stopped, and bit my lip. "What was I supposed to think when I learned you you enjoyed expressing yourself like a mare too? I know you are a diva, but this was a lot for me to try and piece together."

"Luna, this is more of a hobby for me than anything... and sometimes it feels right. You know I don't really understand the standards for any of these clothes. Don't get me wrong, I like to go out like this sometimes, and it can be too spectacular not to flaunt. I..."

"When you showed me that news article, you were going to tell me you wanted to participate in drag shows, weren't you?"

I can feel Sombra shift against my wither. "...I would. I know you don't understand it, but this is something that I feel strongly about and is bound to be misunderstood in ways like your dress and behavior was in the Tribal Era. I want you to understand this, and why there are times when I want to dress like this and have everypony get to hear my jokes and see me as I am, though they'll never really know me. I have a change to engage in something I find unusually interesting that caters to some of what I like to indulge in. I don't want to pass up on this."

I comb my magic through his mane quietly, wanting him to accept the affection while my stomach turns over on itself.

"Was this your piece then, dear Som?"

There was a thoughtful pause before he said, "I'm not sure you realize how badly I want you to understand this."

Sombra and I find ourselves in a rare time where the silence between us is awkward.

"Sombra?" I asked eventually, my voice coming out shyer than I had anticipated.

"What?" he replies, and I sense a kernel of irritation buried deep in his tone.

I don't know if he would be grateful to hear an apology, or if it would make my stomach feel any less ill.

"...W-What would your stage name be?"

I read the silence that follows as more of a stunned one, as Sombra sits right up and looks at me. Even without looking directly at him, I can feel his gaze looking over me.

"Cadance suggested 'Rhinestone Eyes'. I couldn't come up with anything better, and it does have a ring to it, don't you think?"

I look at Sombra, taking in his slightly rumpled skirt and the new untidy element to his mane. I think of the vivid look in his eyes, and the sunglasses he likes to wear. They have tiny ruby rhinestones in the frames that accentuate his eyes and gleam alongside them. I recall how he told me he didn't want expensive ones with real ruby shards, for it would be so dreadful if he ended up losing those. Instead, he go sharp, sleek shades that Cadance had declared suitably 'retro' or some similar thing.

"I like it," I admit with a whisper so unlike how strong I want to sound. Even Sombra notes this cursed, rare meekness and lowers his ears a bit more, knowing that I sound so much stronger when all is well.

"Luna, is there something else you need to tell me?" Now Sombra's tone was free of extremes. There was no apparent softness or concern, nor was there any gruffness or anger. His question was level and cool.

But his word choice made me feel dizzy. Sombra was one who knew life without luxury and that the needs of everypony were really quite pragmatic. He was commanding with others, but never about what they needed. Such things were not of primary importance like what he wanted somepony to do.

This doubled as one of the most honest courtesies, and one I could say that I was actually grateful for. He never told me about what I needed unless it was obvious or things seemed dire. I didn't need to tell him what was on my mind at all times. I didn't need to move. I didn't need to do this or that, and so on.

"I..."

Just tell him.

"I'm not attracted to you."

Sombra arches one eyebrow, and there is a boost of sassiness in the gesture because of the touch of makeup he has on. "Haven't we been over this? There's never been a problem with you not being sexually attracted to me."

"No, no... it isn't that. Som, when you wear these things, you are pretty. You... you just are not..."

There was that worry starting to spark in his eyes again, even if he remained unflinching and his eyebrow was still arched, it was unmistakable. How could I say such a thing to him? I was tormenting him, wasn't I?

"I'm not what, Luna?"

"You don't feel pretty to me. I look at you and know you are the one I love, but I think I hate myself for not seeing you in any way that feels as passionately as before. You're still you... but you feel like a mare too... a-and Som, I don't think I like mares."

Sombra's expression softens and his horn glows. A moment later, he's conjured a small scrap of fabric that he presses to my face to dry the tears that have started rolling down my muzzle.

"Well, Luna, I suppose one of us was going to wind up being straighter than the other."

When I am able to shake off a few low sob-shudders, I try and force a question past the swollen feeling in my throat. "...Y-You aren't mad at me?" I sputter, and dare to reach for one of his hooves.

In the back of my mind, I marveled at how steady his hoof was as he slipped it into mine.

"No," he mumbles. I know he means it, but he says it so that I know there's a lot on his mind.

"Som?" I ask, trying to focus on the clouds to help me relax. When all my tears were dried, I passed the cloth back to Sombra.

"Yes?"

"I like stallions."

"I can tell."

For that, I jabbed Som in the wither and was rewarded with a flat stare.

"Mares are different." I gave a heaving, frustrated sigh and looked down at my forehooves. In response to my mental exhaustion, my mane flowed languidly. "So, so different."

"What I've been doing has been making you uncomfortable, then?"

"...It was really just the lipstick. I know that I shall get the rest, in time. Lipstick just feels... slimy. I feel it and think of contact with the lips of the most lush, delicate, girlish little mare. And these mares that prance unwanted into my mind and the sensation are typical girly creatures, with such things embodied by most of the Element Bearers, yes? A regular cast of Fluttershys, Pinkamena Pies, Miss Rarities, and Twilight Sparkles. I feel that in lipstick... and yes, Som, that is what made me uncomfortable. I appear to have a stars-forsaken lipstick phobia of some sort."

To my surprise, he chuckles. "I won't wear it as much, then."

I managed to offer a murmured 'thank you'.

I heard Sombra sigh in relief, but before I could look at him, I felt a soothing scratch behind one of my ears. Out of the corner of my eye, I caught the glow of Sombra's horn.

With a comforting gesture, the weight on both of us felt lifted.

"Luna?"

"Yes?"

"If I were a mare, would that be a problem for you?"

My heartbeat echoes in my ears. "Had you been physically a mare instead of a stallion, I would still love you. If you felt you were a mare in a body not right for you, I would still love you, and though you might be neither and nothing in your mind... I feel the same."

Sombra made a small mur in the back of his throat to acknowledge my words. "What is it that you would like in a mare? Maybe in the future, many ages from now, I would be interested in applying for the position of your marefriend."

"Oh, much that one would find in a stallion, I would think. Strength, courage, independence, introspection, wit, the ability to assert one's beliefs, masculinity-"

"Masculinity?" Sombra repeats slyly. "I think I understand now."

"Y-You do?" I look at him, and see how his eyes meet mine. There is the hint of a relaxed smile on his face.

"I wouldn't be saying that if it weren't true. You like stallions."

"Oh, absolutely! I care not whether a stallion is masculine, feminine, or born in such a way he had no say... it's like how you said, no? You love who you love, regardless of what they are?"

"I would think so," he replies, flicking at one of my ears with a brief display of aura.

"For me, that is what I know what I feel with stallions. You, however, are the most special, and far superior than of any mere guard who gets a moment of slight acknowledgment within my thoughts as pleasant-looking."

Sombra lets out a rumbly trill and leans forward to accept a kiss on the cheek. "And with mares?"

"I like tough mares. Mares like stallions. Not gentle, cute, and... ah, 'dorky' mares. I think that is how it is said? Androgynous ponies are darlings, and especially so with mares. Tomcolts are truly cute, hm?"

A wide smirk spread across Sombra's face. "Of course I would know," he said all too playfully, "I have the most terrible little imp to braid my mane."

I dodge another ear flick and end up getting prodded sharply in my side with his forehoof. Because of this, I wind up laughing deeply and uncontrollably, and all tension melts away. With all the worry gone from his face, it is so obvious that Sombra's crooked half-smile is the same as ever, and his eyes are just as warm as I know them to be, with or without skillfully applied mascara.

I can't pretend to know anything about what I'm doing other than trying to adjust to this part of Sombra, but I think I'm doing it much better than before. I certainly feel a bit giddier about things, and even if it doesn't last, Sombra's here.

Sombra's here and we have the whole day ahead of us for anything to happen. I have one problem solved, but of course that doesn't last.

I've quickly found myself in quite the dire straits, with Sombra hugging me almost desperately with all his might before I can recover from what I had suggested:

That maybe it was time Rhinestone Eyes was gifted their first show-dress.

Comments

[Ice Star]

9200578
I actually debated doing that, but DtI also feels too self-contained in its current state? So, I just decided against it.

[Nittany Discord]

Loved the last chapter, though when it comes to Sombra's gender, the story seems to do a lot of "beating around the bush" about it. It is because Luna is just too scared to ask Sombra about why he likes dresses, or does so much awkwardness exist between both characters on the subject that neither wants to get to the point, or are you keeping the subject of Sombra's gender and fashion preference intentionally vague to add mystery?

[Ice Star]

9211847

Loved the last chapter, though when it comes to Sombra's gender, the story seems to do a lot of "beating around the bush" about it.

Sombra's gender is a big point in this story, but it's actually not the main one. There was a reason that I chose deliberately for Luna to have lots of focus here. (See below.)

It is because Luna is just too scared to ask Sombra about why he likes dresses, or does so much awkwardness exist between both characters on the subject that neither wants to get to the point, or are you keeping the subject of Sombra's gender and fashion preference intentionally vague to add mystery?

It's not out of awkwardness or beating around the bush, but actually something about Luna. Aside from her having a habit of internalizing things and using introspection to process what she learns (as well as her general patience with things) this is about Luna's relationship with Sombra's enjoyment of this and self-expression. Luna's romantic orientation is contrasted what she sees about Sombra's sense of expression, and is the real Thing of the story. Just as is elaborated and stated, she had a very hard time understanding things and felt guilty about it.

Sombra is most certainly not cis by any standards. However, him never explicitly going along with acknowledging any name for his gender is more of just ignoring labels. Sombra's fashion preference is most certainly both masc and femme, and he has his own styles for each. He certainly wanted to get to a point because he had no idea Luna was upset (and was thus questioning what makes Sombra tick, and going through her own explorations, etc.).

I'd say that Sombra's gender is mostly clear at this point. At multiple points he is referred to as 'genderless' and acknowledges this himself. However, instead of it just being an attribute to his species, Sombra enjoys muddying the concept of gender further, especially because he doesn't have one, and is willing to roll with either. 'Genderless' is most certainly another way of describing someone who is agender, and the literal meaning of the word. Sombra is just fairly divorced from the concept of identifying himself under the trans umbrella. Sombra fits the definition quite literally, he just doesn't delve into it or question why he expresses himself the way he does in a way that specifically focuses on gender. (Especially because gender norms don't really exist to him.)

It's Luna's worries, relationship, and romantic orientation that are really the spotlight of the story. She has been told why he feels the way he does and why he does what he does, but struggles to fully understand her partner. She has no problem with how Sombra identifies and cares for him deeply, but fears that his gender expression and her romantic attraction clash. And they do, a bit. (Especially because of how much she's worried.) Luna outright states that Lots-O-Femininity is more or less (for lack of a better term) a turn-off to her.

The part that really says this the most is when Luna tells Sombra she thought of him as male-like/mostly male/etc. not out of black and white thinking, but because that was how Sombra decided to present and acknowledge himself. When he reveals he does both, she feels like she's doing something wrong and is deeply confused.

So, yes, Sombra's gender here is important, but Luna's relationship with how Sombra decides to be Sombra is what matters more. Hope that helps!

[Nittany Discord]

9212666
I see. It all makes sense now.

[Ice Star]

9213559
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