A Beginner's Guide to Gold Digging: Chapter 5

A Beginner’s Guide to Makeovers

Lily

3 Years Ago

“What are you wearing?” Olivia said, eyes narrow, frown deep-set, fists on her hips. 

I stood in my kitchen, bathed in sunlight and awash with the marinara and garlic and oregano smell of the pasta sauce cooking on my stove. My shoulders went slack and I struggled to make eye contact. “Um… A dress. Does it look good?”

“Lily, honey, sweetheart, no. It does not,” Olivia said, strutting forward in her own baby blue sundress with white polka dots, tossing back her curtain of long red hair. She grabbed a fistful of my simple yellow shirt-dress, one which I’d gotten at a thrift store for only ten dollars. 

I’d been there looking for a new bookshelf for my comic collection, and I’d just… Seen the dress hanging from a rack in the clothes aisle. It wasn’t flashy or even particularly sexy, but it looked… Cute. And I was curious. I’d never worn a dress before. I’d only started socially transitioning two years prior, and I’d always been content to hide my feminized figure with baggy clothes, but something about this one, the way it made it more obvious that I had breasts and hips and long, smooth legs, the bright and sunny color, the soft, silky fabric… It was like it called out to me. I figured ‘what’s the harm? It can’t look that bad on me.’

Apparently, though, it did.

“What’s wrong with it?” I asked, an icy slash of shame knifing my chest. 

“It’s just… This isn’t for you, Lily,” Olivia said with a sad smile. “This isn’t you. You’re… You know? You wear sweatpants and hoodies. You don’t have much figure to show off, so maybe don’t try to? Plus, the way you usually dress makes this less obvious.”

She poked my soft belly, and the icy shame slashed again and again and again-

“You should really go get changed,” Olivia said. “I have a suit you can wear for dinner. Men’s wear looks much better on you. And besides, just because you’re a girl now doesn’t mean you need to do all this stereotypical stuff. Frankly, I kinda feel sorry for you for thinking you have to. Did someone tell you to dress like this? Because if they did, you don’t have to do any of that to be a woman. Girls like you just look like caricatures when you try to femme up like that.”

“O… Okay,” I said, all the joy I’d felt from the dress snuffed out in a blizzard of self-loathing. She was right, of course… I looked ridiculous. I used to be a man, so men’s clothes would always look better on me.

I let myself go numb as I climbed out of the dress and let Olivia put me back into a pair of pants. She was right. I’d never be able to pull off something like that dress.

I threw it into the trash once I got changed.

Now

“Oooohhhh, what about this one?” Rose said, taking a maxi-dress the color of sunshine off of a rack at Nordy’s. It had long sleeves and a long skirt and a modest neckline, plus a few white accents around the shoulders. She held it in front of me, and a familiar cut of cold shame slashed through me. 

“I, uh, I’m not really sure yellow is my color,” I said, wringing my hands together. 

“You sure? I feel like with your complexion-”

“Just… Please no yellow,” I said. 

She furrowed her brow, but then smiled and nodded gently. “Okay.”

“Thanks.”

“Of course! Girls like us gotta stick together, you know?”

“Yeah, yeah definitely,” I breathed out. 

I looked around. I’d never been to a place like this: white walls and floors and bright lights casting radiance over rows and rows and racks and racks of dresses and blouses and skirts. Sweet perfume smells emanated all around a wide-open expanse of white walls and sterile linoleum floors and bright overhead lights. The ceiling was high, classical music vibrated out of the speakers, and the whole place radiated femininity on every conceivable level. I felt woefully out of place, underdressed and mannish and disgusting, like some sort of crude facsimile of a woman intruding where I didn’t belong. It didn’t exactly help that there were literal supermodels doing a photoshoot involving beach balls that looked like disco balls, shimmering as they bounced through the air while the models strutted about in mini-dresses and spike-heels. 

I would never look like that. There was no point in trying. I shouldn’t want it. I should be content with the lazy tomboy look I’d resigned myself to. It had gotten me through life thus far. Still, some of these dresses were very pretty, even if I knew they’d make me look like a dwarven elephant with rabies and a staph infection. 

Besides, I had it easier than these girls. I didn’t have to conform to some impossible standard of femininity. I could just be… This. No matter how boring ‘this’ was. 

Whatever. I could wear a dress for one night and be done with it. 

“How about this one?” Rose said, holding a pastel blue sundress with short sleeves and a billowing skirt to me. 

“I dunno if-”

“Oh boys!” Rose called out over my shoulder. “What do you think of this one for Lily here?”

She spun me around to face Kyle and Cris and held the dress over to me. Cris was on his phone, texting someone, while Kyle was standing there grinning with his hands in his pockets. “I think that would look beautiful on her. Cris? What do you think?”

Cris didn’t look up from his phone, simply grunting instead. Oh thank God, I don’t think I could live with the embarrassment if he-

Then Kyle smacked him on the shoulder in a way that looked only fifty percent playful and said, “Dude. Compliment your fiance. Now.”

“I’m not sure she-”

“Dude.”

I cut in with, “That’s alright-”

“DUDE.”

Rose (still standing way too close to me, a fact which sent a bizarre mixture of arousal and some alien sensation humming through my body) offered, “Kyle. Too much.”

“Sorry,” he laughed. “Just trying to pitch in.”

“I know you are, babe. Love you!”

“Love you too!”

“Ugh. Straight people,” I groaned. 

Rose whispered into my ear, “Yeah, uh, maybe less of that when we’re in public?”

“Sorry,” I grimaced. Shit, why did I say that out loud!?

Cris finally put down his phone and walked over, taking the dress out of Rose’s hands and holding it over me himself. I steeled myself for whatever disappointed barbs were about to come my way, but he only said, “I think this would look absolutely beautiful on you, angel.”

“A-are you fucking serious?” I balked. 

He squinted. “Yes. Obviously. Why wouldn’t I be?”

“I… I don’t know.”
“Well… It would look good. So yeah.”

I nodded, breathing out as I took the dress in hand and turned in the direction of the changing rooms… Only for a beach ball to hit me in the face. 

Cris was in front of me before the inflatable ball hit the ground. “Are you okay? Did it hurt? Do you need me to get you anything? Ice pack? Painkillers? Stiff drink?” he said at a hundred million miles per hour. I couldn’t decide if it was sweet or condescending. Maybe both.

“Cris, it was a beach ball,” I said. 

“Oh,” he said, kicking the sequined sphere errantly. “Right. That makes sense.”

Yeah, it was both.

“You’ve got a sequin in your hair, by the way,” he said, pointing at my head. 

“Where?” I said, raking a hand through my short curls. “Did I get it?”

“No, it’s… Uh…”

“Where is it?”

He reached his hand, put it in my hair, sliding through the smooth tresses until he came away with a sequin pinched between his fingers. “Here.”

My cheeks heated and a gulp went down my throat. That warm flooding feeling returned, attempting to sweep me away and send me God-knows-where. So instead I planted my feet and swallowed down deep. “Ask first before touching me!”

He flinched. Shit, that came out harsher than I wanted it to. Maybe I should apologize? No, no I’d set the boundary, I needed to maintain it. But how to make amends… Maybe a compliment. Yeah. Guys never get compliments, so he’d surely appreciate it.

“But uh, thank you. You’re good with your hands,” I said. Nailed it! … Wait, why was he blushing? Why was he looking away? God, why didn’t boys make any freaking sense?!

“Sorry about that,” a deep, booming voice reached towards us, pulling our attention away from each other (probably for the best). The source was a man who dwarfed even Kyle, easily the height of a basketball legend, if not taller. He was somewhere in his fifties by the look of him, with blonde-white hair and a Swedish accent. He was trailed by a small cadre of the above-mentioned supermodels, strutting about like sexy goddessess. I tried my best not to stare. 

Crispin, evidently, did not try that hard himself. Because he was fucking staring at the models in their skimpy clothes and high as fuck heels, with their perfect hair and makeup and breasts bobbling boobily as they sauntered about like they owned the place. Bitch, you what? Your fiance is standing literally right next to you… Okay, fake fiance, but still. 

“Paul Lindegard?” Rose said, walking past Cris and I. “Is that you?”

“It is indeed, My Lady O’Neil,” the huge Swede (Paul Lindegard, apparently) spoke. 

“You know this guy, Briar?” Kyle asked. 

“Yeah, remember that whole Seattle Fashion Week thing?” Rose said.

“Ohhh, he’s that guy,” Kyle said. 

“What’s happening?” I asked. 

“Rose headlined Seattle Fashion Week earlier this year,” Cris said. 

“What?” I balked. 

Cris just shrugged. “If it helps, my initial reaction was the same as yours.”

“What brings you to Boston, Mr. Lindegard?” Rose asked. 

“Opportunity,” Lindegard said. God, his voice was bigger than his body!

“So is this a photoshoot?” Kyle asked. 

“It is indeed!” Lindegard said. “An experimental one, of sorts.”

“What makes it experimental?” Cris asked. 

“Feats of strength and agility!” Lindegard exclaimed, somehow louder than ever. “Volleyball! The ball of volley! Obstacle courses! Scavenger hunts!”

“Lift-offs?” Kyle asked. 

“Yes, precisely!” Lindegard boomed, wagging a finger at Kyle enthusiastically. He turned back to Rose and said, “Would you care to join us?”

“Hmm, I don’t know, Paul. I think my modelling days are behind me,” Rose said. Then her eyes flickered over to me and panic rang like a gong inside my mind. “But perhaps my friend Lily here could be of service? Provided she’s allowed to keep the clothes.”

“Uh-”

“That can be arranged!” Lindegard said as he gave me an appraising look. 

I stammered, “I’m not sure-”

“Paul, come on now, be serious,” one of the models flanking him, a tall drink of water with raven hair worn in beach waves, clad in a pink bodycon tube dress that showed off her massive bazongas and tiny waistline, said in a pristine English accent. “This one can’t possibly hack it in our world. She isn’t woman enough.”

The fuck you say, asshole?!

She traipsed past Paul and walked over to Crispin and I… And put her hand on Crispin’s chest. “You. Beautiful man. What is your name?”

“Crispin,” he replied. “Why are you touching me?”

“And you are unattached?”

Like hell he is! I thought as a white hot burst of rage pulsed through me. I wrapped my arm around Crispin’s waist and dragged him close to me. “He’s very attached. To me. We are engaged. To be married. Because we’re madly in love!” 

The British woman blinked once. Twice. Thrice. Then she erupted with laughter. 

“What was funny about what she just said?” Crispin said, eyes narrowing. “She is my fiance. We are in love.”

“Oh good heavens, but why?” the British woman said. 

“Rebecca, come now,” Lindegard said. 

“I simply must know what could possibly compel such a beautiful man as this to tie himself down to…,” she trailed off, then gestured at my everything. 

“You know what?” I said, grinding my teeth together. “I’d love to be part of this photoshoot of yours.”

“I beg your pardon,” Rebecca said, flabbergasted. 

“Lily,” Cris said, looking at me with skepticism, “Are you sure-”

“Positive,” I said, forcing my face into a sweet smile. At least, I attempted to. No idea if I succeeded or not. 

“Excellent!” Lindegard said. “Come now, let us bring you to the wardrobe. We have an evening gown that I believe would look divine on you…”

“I’ll come with,” Rose said. 

“What should I do?” Kyle asked. 

“Uh, just keep Cris company. Talk about sports or something!”

As I was led away, I heard Kyle say, “So, uh, you see the Sox game last night?”

“More of a combat sports guy, honestly,” Crispin said. 

“Hm. Fair enough. Does hockey fighting count?”

“Sure, why not.”

I was dragged away from the masculine energy, and towards a realm of pure femininity. I gulped as I was led through a sea of girls who were prettier than me and shoved into a changing room, whereupon a dress was thrown over the door and landed in my arms,

It was a slinky number made of black sequins. The hemline stopped above my knees, while the neckline left little to the imagination. My hands were trembling as I pulled off my sweats and climbed into the evening gown, and my heart thundered as I turned around and looked in the mirror to find… 

That… It… Actually didn’t look completely awful. Huh. Olivia said I’d looked like a boy in a dress the one time I’d put one on, but, at least in this one… It looked kinda good? Showed off my figure, complimented my skintone, made me feel… Made me feel… Wicked girly! And I didn’t hate it like I expected to? Like, yeah, I could still hear Olivia’s voice screeching at me in the back of my head telling me I looked ridiculous, but it was drowned out by the warm and gentle sensation that hummed inside of me. It was like a sweet nectar flowed through my veins and turned my soul itself delightfully pink.  Like I was lying on the beach on a perfect summer day, the sand warm on my back and the waves crashing into the shore pushing a gentle seabreeze over me while the sun’s warm rays kept any cold shame or apprehension at bay. Like I was… 

Like I was me. 

Huh. 

I turned around again, and the skirt of the dress flared around me, spinning as I turned, and my jaw dropped as the warm, sweet, sense of ME grew even stronger. It spinned. Did they all do that? Why did nobody tell me this?!

I opened the door to find Rose waiting for me outside. “Hot damn, girl, you look fantastic!”

“You really think so?” I asked, looking down.

“Fuck yeah,” Rose said. 

“Thank you,” I said, my smile genuine for a change. “Hey, so did you know that when you spin while wearing a dress, the skirt spins with you?”

Rose put a hand over her heart and smiled. “It goes spinny, yes.”

“How am I just finding this out now?!”

“Well, you said you’ve never worn a dress before,” Rose said. “I kinda just assumed that was a whole ‘not my vibe, not my aesthetic’ thing and you were being hyperbolic, but… Uh, you really have never worn one, have you?”

“I tried one on once, years ago, and it… It didn’t look good on me, so I threw it out,” I said, my fingers gathering into trembling fists. “But this is… You’re sure this looks good? My eyes aren’t playing tricks on me?”

“Lily,” Rose said. She was wearing heels, which brought her up to eye-level with me. “I promise you, you look good. And, while I’m sure this only matters so much to you, I know Crispin would agree.”

“You guys know each other pretty well, huh?” 

With a wistful sigh, she said, “Yeah. And he’s not the same as he was when we were kids, but neither am I. I am glad he’s back in my life, though.”

 A nervous flutter shook me. “Did, um, you guys ever-”

“No,” Rose said. 

“You didn’t let me finish.”

She put a hand on my shoulder. “Nothing ever happened between him and I. And I love Kyle very much, so I wouldn’t want anything to happen. In another lifetime, perhaps he and I would have been something, but I wouldn’t trade what I have now for anything in the universe. And I know he’d say the same thing.”

“What makes you say that? I’ve seen him giving you some looks-”

“That’s just how guys are. They don’t even notice they’re doing it half the time,” Rose said. “Besides, I think he’s pretty happy with what he’s got now.”

I rolled my eyes. “You mean my gay ass?”

She pursed her lips, while her beautiful blue eyes danced in a way I couldn’t interpret. “Something like that.”

“What does that mean?”

“Don’t worry about it, girly girl.”

“Oh, don’t. I am not a girly girl-”

“Why not?”

“I haven’t earned it!”

She furrowed her brow. “Yet another thing you’ll need to unpack at some point.”

“What-”

“It is time!” Lindegard’s voice exploded into the changing room. “Come now, Lily! We must paint your face!”

My eyes bulged. “Oh God, I didn’t think-”

Rose took me by the hand and dragged me out of the changing room area. “Relax. These people are professionals. They’ll only do what they know looks good on you.”

I nodded, anxiety festering in my throat as I was led to a vanity mirror and sat in a wooden chair. A heavily-pierced punk girl with sleeves of tattoos running up both arms and a messy black dye job put both her hands on my face. “Um, what are you-”

“Silence, my child!” the girl exclaimed. “I must feel my canvas before I complete my newest masterpiece!”

“That’s a little grandiose,” I deadpanned. “It’s just makeup.”

“JUST! MAKEUP?!” the young woman bellowed. “Unbelievable! Inconceivable! Heretical!”

“I- I’m sorry, I just-”

“Silence! Silencio! Fame la bouche!” the punk said. “For you have spoken the most blasphemous of words! As such, I must perform my most spiteful of acts upon thee!”

“Oh God, you’re gonna make me look even uglier than usual!?” I said, suddenly regretting my words and actions. All of them. From my entire twenty-five year old life. 

“Nay! I shall make you look beautiful! A heretic can only be converted through the most powerful and fabulous of magicks!”

“Huh-”

“Sssssiiiiiilllleeeecceee!” she hissed. 

And then she got to work painting my face. That warm sweetness returned, tripled, quadrupled as brushes worked powder onto my face and pencils and wands worked on my eyes. My skin wasn’t terrible by any means; I could probably stand to drink more water, but so could most people. Still, only a few acne scars were left over from an adolescence spent popping pimples. But when it was done, and the punk started putting lipstick on my mouth… I saw something I’d never expected to see. 

I’d known, objectively, that makeup could make a big difference. But actually seeing it first hand… It was something else. The red on my lips was the cherry on top of it all. I didn’t look different per se, but I looked… Goddamn, I looked good. My eyes were huge and my lashes were long and my skin was clear and smooth, and my lips… Holy shit, those were kissable as fuck!

Images flashed before my mind’s eye. Of Olivia kissing me. Of Rose kissing me. Of Crispin kissing me. That last one came through clearest and loudest, and the warm sweetness returned stronger than ever. I shook my head, trying to banish the image. I didn’t want to kiss Crispin, obviously. There was no way. It wasn’t possible. I was a lesbian and that was that. The image peristed, and the sweetness turned sickly, tainted with the blight of shame and anger. I heaved a deep breath, forcing myself not to feel it. I was just confused. Just getting in character. The whole Mid-Atlantic High Lady thing I’d channeled earlier.

The thing Crispin had told me never to do again. 

I should probably just do what he told me. Not that I needed a man to tell me what to do, obviously (OBVIOUSLY), but he was helping me out… On the other hand, though, the look on his face when I’d done it the first time had been priceless. Maybe if I did it again dressed like this he’d freak out even more!

Heh. Watching him squirm was delightful. 

They put me in a pair of mild heels, only an inch high, which was still more than I was used to, but I got it pretty quickly. Heel-toe, heel-toe, heel-toe… 

“Hmph!” Rebecca said as I walked past her. I just flipped her off in response. Rose, to my delight, did the same. 

“So, bossman, what are we doing?” I said as I sauntered up to Lindegard, Rose giving me the thumbs-up off to the side. 

“We are engaging in one of the primordial contests of humankind, a struggle of champions that dares to ask a question we all seek the answers to, so that we might satisfy the longing for knowledge that burns inside of your soul,” he replied. 

“And what question is that?”

He gestured behind him, revealing two lines of models, each holding poles in rows. “How low can you go?”

Did I mention that all the models were wearing roller skates and slowly drifting backwards in time with each other? Because that was also happening.

“Oh, boy,” I whispered. 

“What’s the matter, tomboy? Afraid you’ll trip?” Rebecca said as she effortlessly lowered herself and began walking the massive procession of limbo bars. 

“Oh hell no!” I said, making myself go low (which was a weird experience with the heels fucking with my center of gravity). 

My shorter legs did their damndest to keep pace with Rebecca as we limbo raced in the moving procession, all while Lindegard trailed after us snapping photos. We wound up going out of Nordy’s and into the rest of the mall, up and down ramps, through a food court, past a game store filled with gawking teenage boys, into a collectibles shop wherein we navigated past an auction of people bidding over a Gundam model kit from forty years ago, past a massage parlor wherein oily men greased each other up and rubbed each other down. I nearly tripped when I found myself staring for some reason, but I composed myself when Rebecca actually did trip and fell out of line. 

“Hah! Suck it!” I pointed at her while still limboing, even as my back began to scream at me. Curse you giant mommy milkers! I mean, not really, they were great, but still! 

Two more models skated past us and began playing with the disco beach ball, knocking it between them over the procession as we made our way back into Nordy’s. A crowd of onlookers began to trail after us, a few from each place we’d gone through, applauding and hooping  and hollering as I drew closer to the finish line. Finally, we made it back to where we’d started, and I found Kyle and Crispin waiting there with Rose. 

The procession stopped. I cleared the final limbo line. 

And immediately fell backwards, expecting to land on my ass. 

I didn’t. 

Crispin caught me. 

His hands were on my hips. His face was right above mine. His chest was heaving in time with my own haggard breath. 

“You okay?” he asked, his warm breath mixing with his. 

“Mm,” I moaned. 

“Sorry, I should have asked-”

“No, it’s fine this time,” I said, that sweet warmth filling me again, this time without any taint on it at all. It was way too close, but it was also… Kind of nice. That he was willing to catch me as I fell was… “Very gentlemanly.”

“That’s what I aspire to,” he laughed nervously. 

“Helps that you really know how to go down on me,” I grinned. 

His face went so incredibly red. Redder than Rose’s hair. “That, uh, that-”

I let my voice go up and started glossing my words with the mid-Atlantic accent again. “Oh my darling, beloved Crispin, you Gentleman Douchebag-”

Then he let me fall on my ass. Eh, I deserved that one. 

He offered me a hand up. “The dress looks good, by the way.”

“Thanks,” I smiled, the sweetness nearly overtaking me, the warm flood turning to a gentle river I could bob down.

“Excellent! Truly excellent!” Lindegard said, clapping as he approached. Rebecca trailed behind him with a sour expression I couldn’t help but snicker at. Lindegard snapped his fingers, and a tired-looking college-aged intern approached with a large burlap sack with a green dollar sign stitched into it. “Your payment. In addition to the dress and shoes.”

I took the sack, and then nearly fell over again. “God, it’s heavy! What is in this?”

“Quarters,” Lindegard said. 

“Why do you-”

“In addition to my other business endeavors, I also own a line of vending machines.”

“Well alright then,” I said. “Uh, thanks. I guess we’ll be off now to finish our shopping?”

“Sounds good,” Rose said, her and Kyle walking back towards the rows of dresses hand in hand. 

“Here,” Cris said, reaching for the burlap sack. “Let me help you carry that. Share the load.”

“Sounds good,” I echoed. Carrying the weight with Cris alongside me wasn’t as bad as doing it on my own. “Sounds like a good plan.”

And so, one dress acquired, we went back into the fray.