Concerning Two Kinds of Dressing

If Denni’s misgivings upon taking Holly up on her offer had been noisy back at the bar, they spiked heavily when Holly’s aforementioned hotel room turned out to be a screamingly posh executive suite at the top of an equally ridiculous boutique hotel a couple of blocks away from the bus terminal. Denni found themself standing in the center of a marble floored living room with designer furniture that both appeared angular and weirdly comfy at the same time, while trying way too hard to project a vintage 60s aesthetic. Clutching their beat up suitcase, lovingly reinforced over the years with varying colors of duct tape, and their faded LL Bean backpack that they’d been hauling around since high school, Denni felt grossly shabby and out of place.

Holly seemed oblivious to Denni’s discomfort, blithely chattering about the evolution of 10th Avenue since her long ago days of coming back to the city when the area around Port Authority was 99% peep shows and porn theaters. “If you looked out the front doors of the terminal back then you’d be greeted by a giant neon vagina surrounded by gogo dancers underscored by the words ‘Welcome to New York,’” she was saying, casually flinging her Christmas nightmare coat over an aggressively pointy puke-green chair. “Honestly, I kinda miss that. That new Times building seems devoid of personality in comparison.”

Denni, still debating whether sinking into the marble floor was a possibility, was only half-listening, but detected enough of a pause in Holly’s breathless chatter to insert an “uh-huh” as they quietly tried to look like they weren’t panicking about the speculated cost of the suite.

Holly, belatedly noticing her guest’s distress, made a concerned face. “Do you need a snack or something to drink? There’s a mini-fridge in here if you need something quick or I can doordash something for you if…” she trailed off, frowning slightly at Denni’s rapidly paling face, before cottoning onto the source of their horror. “Oh, honey, they seriously don’t charge THAT much for taking stuff out of the minibar, I promise. Sure, it’s a little more than the same stuff at Duane Reade but… convenience.” She shrugged. “It’s really okay, it’s my dime.”

Denni closed their eyes and took a deep breath. “Sorry,” they mumbled. “Just feeling a bit fish out of water. Pretty sure this suite’s alone’s worth like several weeks of my paycheck.”

Holly pouted a little but it was sympathetic, not resentful. “I’m sorry. Is there anything I can do to make you feel more… comfortable seems like the wrong word, but it’s all my brain is coming up with.”

“Not really.” Denni offered their host a wry grin. :This is just weird, and I have the feeling it’s only going to get weirder before the night’s over.”

“Well, I certainly hope so.” Holly smiled, plopping herself down on the aggressively cuboid fuzzy sofa. “Seriously, raid the fridge, take a shower if you like, make yourself at home, we have some time before the party.”

“Oh right, about that…”

Holly lights up, clapping her hands. “Right! Something to wear. Let me make a phone call. Get a snack, seriously.” She pulled out her phone, pulled a face for the facial recognition lock, and excitedly poked her screen twice before holding the phone out in front of her. 

Denni gingerly opened the fridge while she did this, discovering a rather impressive array of tiny bottles of wine, several small cans of craft IPAs, the usual complement of sodas and seltzers (including both coke and pepsi products, unusually), several slim boxes of godiva truffles, a couple thin plastic tubs containing fancy salads, and a few small sandwiches on extremely chunky looking bread.

Holly’s phone emitted a series of low-pitched bloops, and a smooth, lightly-accented baritone voice spilled out of her phone. It immediately seemed familiar to Denni, though they couldn’t have placed it to save their life. “Well, hello, Pickle. That is absolutely creepy, I was just talking to Shel about you. Are you on your usual birthday bullshit?”

Holly grinned, and Denni realized belatedly that she was on a video call. “Hi yourself, Kolya. Yes, I am. Hi Shel, if you’re there.”

“Always,” a higher, more echoey voice chimed in.

“Kolenka, I need a favor. I know y’all are horribly busy, but I’ll make it worth your while.”

“Speak,” Kolya answered.

“So I’m going to the Natural History gala a little later tonight” — Denni quietly swallowed a squeak, as Holly had said it was a party not a gala — “and I have acquired a +1 at the last minute.” She poked her screen and aimed the phone’s rear camera at Denni. “Say hi, Denni!”

Denni made a face. “Hi Denni,” they parroted, giving an awkward wave at the camera.

Holly tapped her phone again, presumably switching back to the front camera. “Denni’s passing through New York, and does not have something to wear for this. I’m making a guess that they’d be most comfortable in a dark suit?” She looked up from the phone for confirmation and Denni managed a nod back. 

“Interesting. Where are you?” Kolya’s voice sounded as if he was holding back a laugh.

“Up the street at the Cachet. Room 406.”

“Noted. Denni, darling? Put them back on the screen.”

Holly flipped her camera again. “Uh, hi?” Denni asked, still flustered by the entire situation and also by a dude they couldn’t see using the correct pronoun and a pet name despite having never met them.

“Do you know your sizes? Approximately? Any size scale will do, I just need a range to pick items from.”

“Umm.” Denni felt the color rise in their face. “I wear a 16W pant, but last time I got it actually measured I’ve got a 27” inseam. Chest/waist/hip is 38, 32, 40… no wait, the top is actually about four or five inches smaller now, if you catch my drift?”

“Completely understood. Any idea about your shoulders?”

“Honestly, nah.”

“Hmm. Take your jacket off and stand up straight, please.”

Feeling more than a little self conscious, Denni shed their jean jacket, leaving them in a plain white t-shirt.

“Hmm, okay.” Kolya’s voice sounded satisfied. “I think I’ve got a few things that should work. Are we looking for ‘complimentary to Holly’s outfit but nondescript’ or we going to go slightly adventurous? You know what, don’t answer that, I’ll bring options for both. Holly, you demented little chihuahua, expect me in about 30 minutes.”

“Don’t keep him too long,” the other voice (Shel?) chimed in. “We’ve got other Christmas parties to outfit, you know.”

“An hour, tops, provided something he brings over works out,” Holly promised before ending the call.

I guess rich people don’t bother with goodbyes, Denni mused. 

Holly put her phone away. “Find anything good in there?”

Denni waved one of the salads. “This okay?”

“Of course. Eat fast though, if Kol said he’s going to be here in 30 minutes, that means he’ll be here in 20.”

Denni shakes their head. “So you just happen to have tailors on speed dial? And what kind of nickname is ‘Pickle?’” they asked, shoveling a forkful of salad into their face, briefly shocked at the fresh greens and lightly spicy dressing.

Holly grinned. “Kolya and I went to high school together. He and his partner run Nikolai & Shelby down the street from here.”

Denni nearly choked on their salad as puzzle pieces suddenly fell into place. “Wait, Kolya is Nikolai Shastov? The designer?”

“Oh, you’ve heard of him!” Holly seemed utterly delighted by this.

Denni blinked at her. Heard of him. Jesus Christ. Nikolai Shastov had caused a bit of a ruckus in the fashion world a few years previous by launching the Nikolai & Shelby line of ready to wear and bespoke suits specifically for the LGBTQIA+ community, emphasizing plus sizes, women, and non-binary/trans masculine bodies. Denni had a pinterest board full of their lookbooks, but as their suits were way outside of Denni’s price range, getting to actually wear one had been instantly written off as a pipe dream. “Fucking hell,” they murmured, covering their shock by stuffing more salad into their face.

“As for ‘Pickle,’” Holly shrugged mysteriously. “Lets just chalk it up to a long ago incident involving a school cafeteria and a LOT of vinegar.”

Denni decided they didn’t actually want to know.

Somehow even trying to mentally steel themself to the idea did not prepare Denni for Nikolai Shastov himself barreling into the suite upon Holly letting him in, instantly filling the room with a relentlessly businesslike cheer. The fact that he was six-foot fuck-you inches tall, built like a defensive linebacker and dressed in a pinstripe suit sharp enough to cut glass didn’t help, nor did the fact that in addition to the suit and the height, he had the gall to be gorgeous as well, with giant blue eyes that crinkled warmly when he smiled, and a head full of thick, perfectly coiffed, prematurely silver hair. Pictures and TV did not do the man any kind of justice. Denni usually didn’t feel attracted to cisgender men, but this beautiful behemoth was a rather unsettling exception.

He stooped to kiss Holly on both cheeks then dropped the full to bursting garment bag he had brought over the same chair Holly’s coat was draped on, making a face as he did so. “Really, Pickle, I can’t believe you’re still terrifying people with this abomination,” he sighed, shrugging out of his suit jacket and rolling his shirt sleeves to the elbow.

Holly laughed. “What a thing to say about something you made.”

“As a joke. I wasn’t expecting anyone to actually fall in love with the eyesore, let alone humiliate me for five years by actually wearing it in public.”

Holly shrugged without remorse. “I keep my end of the bargain, Kolenka. I never tell anyone it’s you.”

Nikolai rolled his eyes, muttering what were clearly Russian curses under his breath before turning to Denni. With a genuinely warm smile, he stuck out his right hand. “Salutations, I am Nikolai. Please call me Kolya or Niko. Also I don’t know how you got mixed up with this insane hellion over here —”

“Hey, now,” Holly pouted.

“ — but condolences in advance for whatever madness she drags you into.”

Denni, willing themselves not to pass out from sheer starstruck, shook the offered hand, noting it was easily twice as big as their own. “Denni,” they manage to hoarsely squeak out.

“Charmed. Right. I am afraid my time is at a premium, so if you would not mind standing on…” Kolya’s eyes took in the entire room, spied an ottoman in the corner, and quickly relocated it in front of him. “Climb aboard,” he invited, pulling a tape measure and a gilded pin case out of his waistcoat pocket.

The next few minutes passed at a breakneck pace as Kolya efficiently and very respectfully took all of Denni’s measurements, being sure to ask for consent before each instance of touching Denni with the tape measure. Denni was certainly not expecting to be casually asked whether they would like their pants to accommodate “packing accessories” and definitely was not proud of the surprised squeak they emitted in response before mumbling with embarrassment that it wouldn’t be necessary. They were then sent into the bathroom repeatedly with different pants before they settled on a pair that was a shade of green so dark it was indistinguishable from black in all but the brightest of lights. They were sent back again to turn said pants inside out so Kolya could quickly whip-stitch them closer to Denni’s body. “What have you got for shoes?” he asked, careful not to drop any of the silver pins he held between his lips as he sewed.

“Just the Docs I came in with.”

“Those’ll be fine,” Kolya declared. “Holly, make yourself useful, put a towel over that dress and give those boots a good shining, there should be a brush and polish in the front of my bag. You remember how, yes?”

Holly rolled her eyes. “Contrary to apparently popular belief, I’m not a complete idiot,” she grumbled, disappearing into the bathroom to fetch the suggested towel. “If they bill me for the towel, though, I expect the same amount off the suit,” she called back.

Denni gulped. They had decided not to think about how much any of this was going to be, but it was hard not to when it was brought up.

Catching the gulp, Kolya winked. “Don’t worry about it,” he rumbled conspiratorially, softly enough that it could be mistaken for a hum if you were standing far enough away.

Denni frowned. “But —”

Kolya removed the pins from his mouth and held up a hand, his eyes crinkling at the corners. “It’s her birthday. And it’s Christmas. Think of it as me doing an old friend a solid. As for you, no doubt you are at the beginning of one hell of a roller coaster ride of a night. Least I can do to make it easier is to make sure you look smashing even as you get dragged along in Holly’s nonsense.”

“You know I can hear you, Kol, right?” Holly emerged from the bathroom with a towel tied around her neck like the world’s longest lobster bib, looking exasperated as she grabbed Denni’s discarded boots from the floor.

Kolya ignored her. “Just try to keep her from getting into too much trouble,” he continued with another wink, before tying off the running stitches and returning to conversational volume, which on him was more of a booming foghorn. “All right go flip these back around, then come back for the rest of this.”

Denni hadn’t the faintest idea how they were supposed to keep Holly out of trouble, so they just dumbfoundedly stayed quiet as they was buttoned into a whisper-soft collared shirt over the t-shirt, followed by a deep green plaid waistcoat and a bright red necktie matching Holly’s dress “for a pop of color,” according to Kolya. “Oh, before I forget,” he continued, pressing a small tin into Denni’s hand, “Go in the bathroom, take a quarter-sized dollop of this, rub it between your hands until it gets more liquid than waxy, then finger-comb it through your hair. Trust me,” he says warmly. “Are you okay? You’ve barely said anything during all this.”

“I feel like a doll,” Denni blurted out. “Not in a bad way? But I don’t think I’ve been dressed up like this since I was small enough to be forced into dresses.”

Kolya laughs. “Yes, I imagine that would be strange.” He sat back on his heels, considering Denni’s face. “May I ask a personal question?”

“I guess, sure?”

“Do you wear makeup at all?”

Denni smiled. “Oh, that kind of personal. A little lipstick and eyeliner sometimes, not more than that.”

“Skip the lipstick, but consider the eyeliner if you have any,” Kolya waved Denni towards the bathroom. “Attend to your hair, then we can do the jacket.”

Denni’s eyes nearly fell out of their head when confronted with their reflection in the gigantic floor to ceiling bathroom mirror, taking in the full effect of the suit sans jacket on them. The few times they had attempted a dress suit, it always had the effect of a kid playing dress-up in their father’s closet, as they always had to go with items that were slightly too big everywhere else to accommodate and hide the hips and ass they’d been unfortunately blessed with before transitioning. Even without the jacket, the pieces worked with their shape rather than attempting and failing to hide them, yet did not make Denni appear feminine. Dragging their eyes to their face, they grudgingly admitted Kolya was right about the eyeliner before finger-combing the pomade through their hair as instructed, giving it a swoopy volume that squared off their usually rounder face.

“Excellent,” was all Kolya said when Denni returned. “And now the final piece,” he announced grandly, holding out a jacket that was not quite as dark a green as the pants but was just enough darker than the waistcoat to make it show up nicely. Denni obligingly stuck one arm into a sleeve, swinging the rest of the jacket around themself and buttoning it at the waist.

“Oh, you look absolutely perfect,” Holly exclaimed. “Kolya, how do you do it?”

“God-given talent,” Kolya retorted. “Denni, how does the jacket feel?”

Fantastic. Euphoric. Sexy. Gender affirming. Mysterious. Entirely unlike their usual self. Denni was unsure how to sum up all of these so they responded to the question with a grin and an awkward thumbs up.

“And yet another satisfied client for the books.” Kolya nodded and hoisted himself off of his knees with a groan. “Fuck getting old,” he complained, gathering up his tools and the rejected suit pieces he’d brought with him, smoothly packing them away in the garment bag. “One of you please drop the pants back at the shop tomorrow? The stitches I put in will hold for tonight, but I would like to make them more secure and permanent before handing them off to you for good.” 

Denni began to protest again, but Kolya cut them off with a gesture. “Once an outfit finds their person, it would be a crime to keep them apart for a reason as gauche as money. Besides, if you’re truly worried about the cost, I’m sure I can find a way for Holly to make it up.”

Holly pressed her lips together, muffling an indignant scream.

“But do keep it, with my compliments. You look fantastic.” 

Kolya flipped Denni a business card, with “N&S” lined in gold foil on one side and Kolya’s full name and a number on the other. “That’s my personal cell,” he rumbled. “Call me if she gets you into more trouble than you can handle tonight. Or, preferably, if you are ever in town again and need another outfit. We do casual wear as well.”

“Thank you,” Denni said, tucking the card into their pocket. “Thank you so much. Seriously, this is kind of a dream.”

Kolya face lit with a gigantic toothy grin. “Fantastic, Holly has brought me a fan. Lovely to meet you. And you!” He gathered Holly into a hug tight enough to lift her from the floor. “Be good, Pickle. And if you can’t be good, for the love of all things holy, don’t get caught.”

“Kol, I need my lungs regardless,” Holly gagged, still buried in the hug.

“Pfffffft.” Kolya let her go and swung his jacket back on. “Don’t be strangers, either of you.”

Denni checked their watch as Kolya — Nikolai fucking Shastov! — slammed his way jovially out the door, once again without saying goodbye. The whole encounter had taken forty-two minutes, far less than the hour promised.

“He’s a fucking wonder, isn’t he?” Holly giggled, her voice cutting through Denni’s starstruck fog. “I wish he could have stayed longer, the man has some wonderful stories and he’ll gladly tell them for hours if mildly provoked.”

“I’ll bet,” Denni said faintly. “I just met Nikolai Shastov,” they continued quietly to no one in particular.

Holly grinned. “You should finish your salad, then we should get going. The event starts in half an hour but if we show up between now and an hour from now we should be fine.”

“Shit,” Denni said. As they wolfed down the remainder of quite possibly the best pre-packaged salad they’d ever had in their life, they wondered if the rest of their evening was going to continue along the same improbable trajectory. They were rather shocked to realize that instead of being nervous, they were now rather looking forward to whatever came next.

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