A Beginner's Guide to Gold Digging: Chapter 6

A Beginner’s Guide to Parental Approval

Crispin

13 Years Ago

I walked arm in arm with Julia Henderson, humming to myself as I brought her to the front door of her family’s mansion. We wore matching white tuxedos to prom, had danced the night away, and enjoyed a healthy afterparty together. All in all, it was a solid first date, and I was hoping we could see more of each other over the summer before college took us in separate directions: Harvard for me, and Wellsley for Julia so she could play softball.

Now, however, for the moment I’d been waiting all night for. 

We stood together under the lamplight of her front porch, her back to the door, our eyes locking together. A full moon hung in the sky, while cicadas sang in the background. A lush green lawn behind me, a possible future staring in front of me, I knew it was time to go for it. I’d been crushing on my good friend since freshman year when she beat me at arm-wrestling, and, with some prodding from our shared best friend O’Neil, I’d taken the plunge and gone to the dance with her when she asked me. God, I was over the moon. This beautiful, strong, intelligent woman had me wrapped around her finger. Now I just had to seal the deal.

“I had a really good time. Do you think maybe I could give you a good-night kiss-”

She kissed me before I could finish. Her lips press against mine, soft and luscious and painted red. Fireworks exploded inside my mind, and I opened my mouth to try to slip her some tongue… But was met with a wall of resistance. At which point it registered for me how uncomfortable Julia actually seemed: her back was stiff, her breath was slow and deliberate, her jaw was set, and her heart… Her heart wasn’t in it.

I’d kissed plenty of girls before tonight. Some good, some bad, some spectacular, some mediocre. But none of them had been as limp and lifeless as this. None of them felt as forced or as tortured as this one. 

I opened my eyes… And found Julia looking devastated. Like she wanted to retreat behind her curtain of long blonde hair and hide away from the world forever.

I pulled back. “Um… What’s-”

“Yup, that clinches it,” Julia said in a sad, small voice. “I’m definitely gay.”

I blinked. “Oh. That’s-”

She held up a hand, guilt and shame rippling through her face and body. “I’m sorry.”

“I-”

“Look, Cris, I… You’re a really good guy. Like, a total class-act. You’re sweet and you’re charming and you’re one of my best friends, and you’re objectively handsome, and I just figured… If there was any way I could… You know, force myself to like something… But I just don’t. I tried very hard, but I just don’t. I’m just gay.”

“Sorry, uh, just to be clear, did you ask me to prom specifically so you could test whether or not you’re gay?” I asked. The fact that I already knew the answer did nothing to quell the ravenous beast of pure dread and shame gnawing at my throat.

“Yes, Crispin,” she said, looking down. “And I’m sorry for using you. I know… I know you really like me a lot. And I do like you as a friend. But that’s-”

“All it’s ever gonna be?” I said. 

She nodded, pursing her lips. She was in so much pain. And I’d heard stories before, about how badly conversations like this could go. Naomi once told me about her wife’s ex-husband going apoplectic when she came out to him, screaming at her, berating her, threatening her to beat her bloody. I didn’t know what to say here, what to do. But I knew I didn’t want to be that guy. That Guy fucking sucked. 

“You’ll make some lucky girl very happy one day,” I said. “Thank you for a nice night.”

Tears leaving mascara-scars down her face, she nodded, then went inside and closed the door behind her.

My shoulders went slack, my eyes wide, my heart a piece of wet cardboard in the process of tearing itself apart. I lumbered across the verdant lawn, not bothering to stick to the brick path that led to the front porch, all the way back to Naomi in the limo.

“How’d it go?” Naomi asked as I climbed in and took a seat. “Did you kiss her?”

“Yeah, uh,” I started. Don’t be That Guy. “Turns out she’s gay. Guess I helped her figure it out.” My heart tore again, and again, and again-

“You okay?” Naomi asked. 

Don’t be That Guy don’t be That Guy don’t be That Guy- “It’s not really about me,” I said. “Can you just, uh, take me home? I need some sleep.”

Again and again and again-

“Sure thing, Cris,” Naomi said with a sad smile.

Now

I checked my phone for the hundredth time, hoping Julia would text me back. No such luck. So instead, I tugged at my collar and looked at the beautiful woman to my right.

“You ready?” I asked Lily as we waited outside of her house. She was using her phone’s camera to check her lipstick; Rose had spent the second half of the afternoon running her through the basics of how to do her face, and Lily kept looking for problems with how she’d done it every five seconds. It was absurd. Like her face wasn’t already fucking beautiful. Like the makeup didn’t somehow make it look even more perfect. God fucking dammit. 

She wore the sequin dress from the mall, which I thought was way too fancy for our purposes, but she wouldn’t budge. I’d picked out a few other dresses for her while we were there, at her insistence. She’d wanted to get her hair done as well, but Rose’s sister Ruth couldn’t fit her in today and Rose was insistent Lily shouldn’t settle for anything less. Lily seemed exceptionally onboard with all this. Something about how we needed to sell the idea that she was using me for my money. I don’t know how she decided the version of this we needed to play up was the one where she was a gold digger, but she was holding tight to that idea and running with it. It didn’t exactly help that she kept slipping into that… That other version of herself. That accent. Those mannerisms. Still obviously her, but also… A version of her who was actually into me. 

I got a boner whenever she did it, the kind that strains against your pants and threatens to stain your undies in public. She talked like that, and I wanted to bend her over and fuck her on the spot, feel her from the inside, drink in her scent and lose myself in the music of her pleasure while she screamed my name. 

And then, inevitably, I felt like a perverted creep. Like That Guy. 

Lily popped her lips. For a girl who’d never worn makeup before, she was getting very particular about it very quickly. “Yes, I’m ready.”
Naomi’s limo pulled up in front of us. “Good,” I said. I opened the car door and beckoned her inside, and she did so. My heart was screaming at me. We were really doing this. We would get my parents off my back, and then it would be over. And I’d never be able to pretend again. 

It was for the best. 

“Why hello,” Naomi said from the driver’s seat. “You must be Lily. I have heard a lot about you.”

“You have?” Lily said, eyes widening. 

“Relax, angel. Naomi is in the know,” I said. 

“Oh, she’s ‘angel’, is she?” Naomi said as she shifted into drive and started us down the street.

“Just… Getting into character,” I said. 

“Good idea,” Lily said. Then she ran a finger beneath my chin and said in that fucking accent, “Dahling!”
Aaaaaaaaaaaaaaahhhhhhhhhh! 

It didn’t help that Naomi wouldn’t stop giggling and grinning the whole time. 

“Okay, so, a few questions my family will probably ask,” I said, pressing my legs together in an attempt to kill my boner. “What drew you to me, initially?”

“Your beautiful emerald eyes, dahling!”

Goddammit, she would not cease! “Hm. And where did I take you on our first date?”

“To a rooftop restaurant on Castiglioni Avenue, dahling!”

 I managed to get the strain in my pants to diminish, finally, after thirty straight seconds of squeezing my balls tight with my thighs. It was worth it. Unfortunately. “And when is our anniversary?”

“May 11th,” she said, then paused and nuzzled my shoulder. Aaannnd my boner came back. Dammit. “Dahling.”

“Good. And where did I take you for the anniversary?”

“You took me sailing on your boat and we ate caviar and drank wine under the moonlight,” she said. “Dah-”

“Please don’t that again,” I groaned. 

“... Okay,” she said, pulling away from me, staring at the floor. “Sorry.”

“It’s… It’s fine. Um… Your turn.”

Her posture straightened. “What first drew you to me?”

“Your abs,” I said. 

She chuckled. “And when did I tell you I’m trans?”

“Third date.”

“And how did you react?”

“I said it doesn’t matter to me one bit. You’re still my angel either way.”

“Damn right I am,” she said, snapping her fingers and pointing at me. “And why have you been fooling around with other girls on the side?”

“Because we both decided it was better to keep ours an open relationship for a while. We didn’t go exclusive until I popped the question yesterday.”

“And you haven’t put a ring on my finger because?”

“Because I wanted to use my mom’s engagement ring, and needed my father’s permission to use it,” I said. 

“Perfect.”

“What do you think, Naomi?” I asked. “Can we pull this off?”

I couldn’t help but notice her smirking as she said, “I think you’re gonna make this work, yeah. In spite of yourselves.”

“Ouch,” Lily said.

“Eh, that’s just Naomi. She’s like that.”

“Is she where you get your dearth of filter from?”

“Probably,” I shrugged.

“Definitely,” Naomi replied. “He learned from the best. The old master of brutal honesty and absolute candor.”

I bowed. “Yes, Sensei.”

We continued the drive, and eventually, my house came into view. 

“Holy fucking shit,” Lily said. “That’s where you live!?”

“Yup.”

“It’s huge!”

“Yup.”

“It probably has its own zip code!”

“Actually it shares one with the rest of the neighborhood, but in essence, yes.”

“It looks like it was built before World War I and has been immaculately maintained!”

“Three for three, killing it.”

She swatted my arm. “Why didn’t you tell me you were this level of rich!?”

“I thought it was obvious from the part where I’m subsidizing your transition and home renovation out of pocket,” I said. 

“... Okay, that’s a good point.”

“And if you didn’t figure it out from that, you would from the picture in our living room of my great-great grandfather shaking hands with Calvin Coolidge.”

“The president of the United States?!”

“He was just governor of the commonwealth back then, but yeah,” I said. 

“Jesus Christ, what have I gotten myself into?” Lily said, checking her makeup for the hundredth time. 

We pulled up in front of the house. “If you wanna back out now-”

“No, no, I can’t do that to you,” she said. 

“Or to yourself,” I offered. 

“Yeah. That too. Right.”

“You kids have fun tonight!” Naomi said. “Be good! Leave room for Jesus.”

“Goddammit, Naomi,” I muttered. 

We got out of the car and walked to the front door. 

“I’m gonna touch you now,” I said. 

Lily nodded. 

I interlocked her fingers with my own. Her calloused hands trembled, so I squeezed them tight until I found the soft center of her palms. That was her in general really: tough and hard on the edges, soft and delicate and vulnerable deep within. No matter how this went, I wanted to cherish her. I wanted to always be near her. I wanted… God, I’d settle for anything. Just being friends with her would be torture, that much I knew from experience, but I couldn’t stomach the idea of us drifting apart.

I opened the door to the Persian-rug adorned, marble-floored entryway, natural light filtering in through stained glass windows depicting our ancestors from as early as the colonial days, and was immediately greeted by the entire freaking family at once. God, I don’t even remember the last time everyone got together like this. It almost made me feel guilty… Actually, no, it really didn’t, most of my family fucking sucked. I wasn’t about to shed a tear over pulling one over on them. 

“Hi there! I’m Lydia!” my eldest sister said as she approached and immediately pulled an unprepared Lily into a hug. Shit, I probably should’ve warned her about that. Lydia was a hugger. She was also my favorite sibling by a country mile. Long black hair and blue eyes, clad in a simple blue skirt and a lacy black top, her own diamond engagement ring on her finger (her fiance, Chad, was out of the country for business), she was always smiling, always bubbly, always trying to help everyone achieve her perpetual good mood. She was also the only one who didn’t seem to object too much to my man-whoring, probably because prior to meeting Chad she’d had a different guy every week.

“Uh, hello,” Lily wheezed. 

Lydia removed her arms from my poor, poor fake future wife, and gave her an appraising look up and down. “Goddamn, you are PRETTY!”

“Oh, come on, no I’m not,” Lily said. 

“And humble as well! Maybe you can teach this nerd here how to be that,” Lydia said, pointing at me. 

“I’m not a nerd,” I said, my eyes narrowing. 

“Nobody believes that, no matter how many times you say it, little bro,” my older sister, Priscilla said as she came over and hugged Lily as well. Priscilla must’ve just come from work: she was dressed in a white pantsuit and her fanciest golden jewelry. She was a redhead, like Mom had been, and wore it in a simple chin-length bob. “Nice to meet you, Lily. I’m Priscilla. Hope my slutty little brother is being good to you.”

“He’s… He’s a perfect gentleman,” Lily said. 

“Ha! I’ll believe that when I see it,” Priscilla said. God, I swear, she got judgier every day. She’d spent high school slut-shaming Lydia… Until Lydia just punched her in the face one day, and so she’d started slut-shaming me instead.

“Hello there, my name is Claudia,” my younger sister said as she came up next. She took after Karen: long blonde hair, brown eyes, dressed in a black tube-dress like she’d come here straight from a nightclub.

“Hi, I’m Lily-”

“Yes, I’m aware. And uh, let me know if you need any fashion advice sometime. You look like you could use it. Plus, maybe less thick with the lipstick next time, yeah? It makes you look cheap. Which I know you are, but still.”

Lily’s mouth opened, and her eyes narrowed, but no words came out.

“Asshole,” I snapped at Claudia. 

“Language, Crispin! Honestly, don’t you know there are ladies present? And, uh, whatever your little tramp here is as well.”
Lily’s expression shattered into crestfallen despair. My hands gathered into fists. “I swear to God-”

“Crrrriiiissssssppiiinnnn!” my father bellowed in his obnoxious faux-British accent (fucker claimed he’d picked it up studying at Cambridge, even though in his case, Cambridge meant Massachusetts and Harvard) as he race-walked towards us, pumping his arms all the while. His hair was white and longer than mine, and his beard much thicker, but otherwise… Yeah, I looked exactly like the old man. Same height. Same eyes. He wore a white tuxedo with a red kerchief in the breast-pocket, a fob watch dangling from his hip on a chain, a glass of aged brandy swirling in his hands. 

“Hi, Dad,” I groaned. “This is Lily.”

“Lilllllllyyyyy!” he said at the exact same volume as he grabbed Lily’s hand and shook it furiously. At the very least, she didn’t look upset any more. Mostly just confused. 

Behind him was my step-mother, Karen. Fifteen years younger than my sexagenarian father, platinum hair arranged in some sort of convoluted updo, clad in white slacks and a red sweater, Karen’s sickeningly sweet smile sat plastered onto her face. “Hah there!” Karen said in that obnoxious southern drawl of hers, kissing Lily on both cheeks. “Ahm Karen Anne Armitage-Winfield and it’s so so so lovely to meet you! Ah’ve waited so so so long for Cris to settle down and Ah already love you for taking care of that for us all!

Between the very forward physical contact and the million-miles-per-hour southern charm, Lily was at a loss for words.

Last and least, my shithead little brother Preston stood at the top of the stairwell just off of our front entrance. He wore designer jeans and a black polo shirt, his blonde hair gelled back, hands in his pockets… And he was glaring daggers at Lily.

“Preston, sugah, you wanna come down here and meet your soon to be sister-in-law,” Karen asked. At least she could be bothered to make nice for the sake of appearances. 

Preston, however… 

“I don’t see her anywhere here,” Preston said. 

“What are you talking about? She’s right there, silly,” Karen pointed at Lily. 

“But that’s not a girl, Mom,” Preston said flatly. 

All the noise in the room, in the whole house, the whole neighborhood, died like a fly meeting a swatter. I’m not really sure what happened next. All I can remember is a feeling akin to a brittle twig snapping before becoming kindling on a campfire exploding in my chest, and the next thing I knew I was up the stairs with my fists around my brother’s lapel. 

“You wanna try that again, you little shit?” I growled. 

“Crrrrisssssspppiinnnn! Pressssttttooonnnnnn!” Dad erupted as he raced up the stairs and pulled us off of each other. “Enough! Cease your childish sibling rivalry at once! We have guests present and as Winfields our sacred duty is to ENTAHTAIN!”

“Dad, I hear you, but that thing downstairs-”

“Is a lovely young lady!” Dad said. 

“Yeah! Exactly,” I started. Then I blinked. Wait a second… 

Dad grabbed us both by the ears and pulled us back downstairs, pain tugging at my skull while tears fell from Preston’s eyes. 

“Is this normal?” Lily asked Karen. 

“Yes, why?” Karen said, tilting her head to the side. 

“Unfortunately, she speaks the truth,” Priscilla said in a flat tone as Dad dropped Preston and I to the floor. My head was spinning with pain and emotional overload: so much was going on all at once and I was struggling to keep up. 

I’d expected Preston to react badly. I hadn’t expected him to react this badly. 

And I’d expected my dad to react significantly worse.

“Crisssspiinnn! Apologize to your brother for assaulting him!”

I breathed in deep through my nose. Ugh. He was right. Preston might have been a little shit, and apparently a bigoted one, but he was still my brother, and we weren’t kids anymore. The days of us roughhousing to solve petty arguments were long-gone.

“I’m sorry, Preston,” I said. 

“Thanks,” Preston said, refusing to look at me. 

“Good. Now! Preston! Apologize to this sweet young debutante this instant!” Dad said. 

“That’s clearly a guy in a dr-”

“Preston! Enough!” Karen snapped. 

And just like that, the little ringworm’s smirk died on the vine. He didn’t apologize, though. He just got up and stalked away, slamming the front door behind him. 

I started to rise back to a standing position. Lily looked scared and overwhelmed and confused and more than a little angry. God, this was a disaster- how had this gone so badly so quickly. I reached out, then mouthed, ‘can I?’  

She nodded, and I put my arm around her shoulder. “Maybe we should go-”

“Nonsense,” Karen said. “Just because my youngest isn’t in a hospitable mood, that doesn’t mean Ah’m not. And Ah for one won’t feel right unless we make it up to you, Lily.”

I groaned, “I don’t think she’s-”

“That’s absolutely perfect, Mrs. Armitage-Winfield,” Lily said, her pitch rising, a hint of that affect glossing her words. “One malcontent isn’t enough to scare me away from my darling Crispin here, after all, and I would love to see more of this beautiful home of yours!”

Wait, what?

“Perfect!” Karen said, taking her in one hand, Lydia taking her in another and pulling her towards the sitting room. Dad and Priscilla followed nonchalantly, while Claudia tossed her hair back and sauntered in that general direction.

Confused, flabbergasted, frazzled, positively fucking baffled, I trailed behind tentatively.

The sitting room was heavily carpeted in a lush white rug, walled by shelf after shelf of classic literature, middled by a rectangular coffee table with couches on both sides, and accented by an unlit hearth next to it. Above the mantle was the portrait of my great-great grandpa shaking hands with Coolidge. Lily couldn’t stop staring at it, even as I caught up with her and pulled her down onto the couch next to me. 

‘I’m sorry,’ I mouthed. 

‘It’s fine,’ she mouthed back. 

‘What?’

‘Play along,’ Lily mouthed before turning to face my family. My sisters were sitting on the couch across from us, while my stepmother sat in a plush chair to my right-hand side. My father was at the dry-bar at the other end of the room chipping ice into a glass of whiskey. 

“Ah, such a lovely room,” Lily said, the accent only barely staying out of her tone. “I can imagine Crispin scampering about here as a youth. Tell me, was he always so effortlessly charming?”

Claudia raised her eyebrows and looked dumbstruck. Priscilla was bemused. Lydia was putting a hand over her heart and sighing with delight. Karen and my father nodded. Me? I felt a tight pinch in my breastbone as a swell of joy washed through me. 

She’s just acting, I reminded myself. 

“Crispin has always been a willful and passionate man, even when he was but a boy!” Dad said. “I looked at him the day he was born, held him in my arms as his eyes opened for the very first time and I saw that they were eyes exactly like mine own! So yes, he was a delightful lad growing up! I remember very fondly him running through this very room with an aerosol flamethrower-”

“She does not need to know that story,” I cut in. 

“I agree,” Lydia said. 

“Regardless, it’s always nice to hear more about this man,” Lily said, patting my knee with her calloused hand. “He’s taken my heart, you know? I’m hopelessly in love with him.”

“Awww,” Karen cooed. Fucking Karen- I was kinda banking on you of all people having a problem with this!

Claudia pulled out her phone and started scrolling. Priscilla looked about the scene with continually amused interest. Dad and Karen and Lydia, however, went all in on Lily. 

They asked all the questions I’d prepared her for, and Lily answered them with poise and confidence of such a quantity and quality that if I was meeting her for the first time I’d believe her myself. Holy hell, she was good at this. She laughed gently and primly at the right points, kept her hands on me but avoided getting into full-on PDA territory, and continually complimented Lydia and Karen on their hair and makeup! And they loved her!

It was… Honestly kind of nice? Usually it was only Lydia who was nice to my women, on the rare occasions that they actually wanted to interact with my family. But they loved Lily, and Lily, or at least this high lady version of her, seemed to love them. For a second, I wanted to forget, to pretend. To let myself believe this was really happening. 

To act like I really was gonna marry this woman. 

But that was ridiculous. And it wasn’t the plan. We needed to stick to the plan-

“There is one thing you should all probably know about me,” Lily said, interlocking our fingers once again. 

Oh, God. She was gonna… Of course, it made sense now! They didn’t realize it. But Lily was gonna tell them now and… I was prepared to fight my way out of here to keep her safe. 

“I’m a transgender woman,” Lily said, squeezing my hand tight. Was she… She was trembling again. She was really nervous. Okay, Cris, you know what to do. She’s a good person and you’ll do anything to protect her. Once the stormwall hits, be ready to-

“Is that all?” Karen laughed. 

Lily blinked. “I… Um, yes, I suppose it is. Is… Is that a problem-”

“Why on earth would that be a problem?” Karen asked in her dixie accent that I’d heard used to wax poetic about the ‘true America’ down south. “Ahm thrilled to have one of y’all in our little family. It’ll make for great optics: the little people can know we stand with them this way.” Oh, Jesus Christ- why would you say that?!

“Indeed, it takes all sorts to make a world,” Dad said with a shrug. “I for one pride myself on an open mind in keeping with the values imparted upon me by my professors at Cambridge.”

“Harvard, Dad, you went to Harvard.”

“And, during my studies, and I knew and loved several women such as yourself-”

“I’m sorry, what?” I balked.

“So I see this as but another way in which mine eldest boy-child can carry on his father’s NOBLE LEGACY!” You cannot be serious, old man!

“I have no issue with this,” Lydia said with a polite smile and a slight shrug.

“I wouldn’t have even known if you hadn’t said anything,” Priscilla offered. “You’re very convincing. Definitely one of the good ones.” Goddammit, Priscilla. 

“Whatever,” Claudia said, not looking up from her phone. “I still think you’re trying too hard. But like… It’s whatever.”

My heartbeat screamed inside my chest as pressure built up and threatened to burst. This was bad. This was bad bad bad; they weren’t supposed to be okay with it. I mean, yeah, other than Lydia they were being passive-aggressive and self-congratulatory and virtue-signalling about it, but still! They were supposed to pretend like ‘oh there’s nothing wrong with that but you’re not really an appropriate match so let’s send you on your way with some money so there’s no hard feelings.’ But this… This… This had gone on long enough. Time to come clean. Getting cut off would suck but I had a job and I had savings and I could probably stay in Rose’s spare room while I looked for my own place-

“Oh,” Lily said in a quiet, tiny voice. “Oh, well that’s… Just wonderful!”

I gulped. 

“Isn’t it, Cris?” she nudged me. 

The pressure expanded. “Yeah.”

“Oh, I’m so happy to have your family’s approval for our pending nuptials,” Lily said, that phony mid-atlantic accent coming out in full. She turned to me. She smiled, even as fear flared up behind her eyes. “This is the happiest moment of my life.”

And for another moment, I let myself pretend. I let the fantasy wash over my mind and carry me away. I let the lie that she loved me calm me down from the frantic, screeching state my consciousness was otherwise consumed by. Looking at her there, leaning into me, those big brown eyes meeting mine, it felt good. It felt real.

Then she kissed me. 

I flinched as her lips, plump and painted, pressed against mine; as her soft body leaned against my larger frame; as her fire and soul mixed with mine; as her tongue slipped into my mouth; as her calloused fingers and soft palms ran through my hair. 

I’d kissed lots of girls before now. I’d had good kisses, bad ones, spectacular ones, and mediocre ones. I’d kissed a lesbian before, known exactly what it was like when the girl felt nothing, what it felt like when she was trying to force herself to enjoy something she simply never would. 

This didn’t feel like that. The heat, the fire, the passion, the joy, the gentle probing and tentative exploration and nervous glee of a girl kissing someone she was genuinely attracted to… That was what I felt. 

And when she ended it, her face still mere inches away from mine, her eyes half-hooded and her smile brimming with contentment, I told myself ‘she’s just acting. She’s just selling the bit. She’s just trying to save face.’

I almost believed it. But another part of me was too busy asking, ‘what is going on here?’