A Beginner's Guide to Gold Digging: Chapter 15

A Beginner's Guide to Gentlemanly Conduct

Crispin

I found Lily laying on the living room couch, curled up under a blanket and scrolling her phone with a distraught expression. Doom-spiralling, probably. Given the state of the world, I couldn’t exactly blame her. “Hey,” I said. “Wanna go into town, get some dinner?”

“D-dinner?” she said, clicking her phone off and slamming it onto the pillow. 

“Yeah, I’m hungry and there’s no food in this house. We could order delivery, if you really want, but there’s a place in town I’d love to take you to. You like Italian food, right?”

She quirked an eyebrow. “Yes, Crispin. I, a proud Italian-American, enjoy Italian food. However did you guess?”

“I’m just wicked smaht,” I said, putting on a thick Southie gloss. 

“Your accent needs work,” she deadpanned with a slight smile. “Also, I need time to get ready. Are you okay with that?”

“It’s a really casual place. Like, I’m probably just gonna do pizza and beer.”

“I… I still want to put on my face,” she said, eyes darting about. 

Okay, Cris, you know what to do. “Alright,” I nodded. “If that’s what you want, I can wait… What, thirty minutes?”

“It does not take me thirty minutes to do my makeup!” she said, standing up and stomping her foot playfully. 

“Then how long does it take?” I asked, stepping towards her. 

She took another step, and she was standing so damn close, looking right up at me, and her lips, even unpainted, just looked so damn good… That smile. God, I can’t believe she thought she had a resting bitch face. This was a smile, a face, a woman, who could launch a thousand ships. “Twenty. Maybe twenty-five.”

I laughed. It wasn’t that funny, but the smug, self-satisfied, faux-outraged look on her face had me in stitches. And she was standing on her tip-toes, her face right up in mine once again. It was exactly where I wanted it. Now all I had to do was shove down the desire to stick my tongue in her throat, grab her by the hips, put her up on the couch and fuck her right there. God, what was wrong with me? “Why don’t you go get ready then?” I said, unable to blink as her face hovered closer and closer and closer to mine. 

She went down on me, her smile flickering. “Okay. Twenty minutes.”

“I’ll set a timer,” I said as she trotted upstairs, and I definitely didn’t watch her ass bounce up and down as she climbed the steps. 

I thumbed through a comic while I waited (seriously, these had been this good the whole time and I’d denied myself for thirty-one years? God, I’m an idiot). 

It was then, however, that I realized something: “Wait a minute… ‘angel’ is what Steve calls Diana!” I whispered. Holy shit! And this whole time I’d been-

Footsteps descended the staircase, and my jaw dropped. I’d seen Lily with her face made up. I’d seen her in a dress. I’d seen her in That Fucking Dress. I hadn’t seen the combination in tandem, nor had I seen her with that combination and a pair of heels that took her from legs for days to legs for weeks and weeks and weeks. They went all the way up and put extra wiggle in her hips and bounce in her boobs. All I could think about was burying my face in her cleavage and going to town on her tits with my mouth as my hands kneaded her hips and ass like dough. All I could think about was my fingers working their way inside her entrance and coaxing an orgasm out of her, gently but firmly.

I stood up in frantic, jerking motion as I covered my crotch with the comic. Oh God, I was going to Hell. And that smile, with those lips painted wine-red… My mind was overwhelmed by a fresh batch of images of those lips on mine, ruining the makeup she’d worked so hard (and efficiently) on; images of those lips around my cock, that tongue swirling around my shaft and those teeth working my foreskin- yeah, yeah, directly to Hell. A special Hell reserved for guys who hit on lesbians and talked at the movies (not that I’d ever done the latter, but having to spend eternity burning with those tools was some Old Testament level divine retribution).

She came up to my eyeline in the heels, and the comic and my pants were doing the Lord’s work. “How do I-“

“…”

She pouted. She had to go and fucking pout with those big red fucking lips in That Fucking Dress. “Cris, when a girl asks you-“

“Fucking incredible,” I said.

She pursed her lips, which did nothing to purge my mind’s eye of images of my dick down her throat. “Okay, that works.”

“Sorry, I just… I didn’t want to make you uncomfortable.”

“Cris, you… You don’t make me feel uncomfortable. You never have. Angry, sure. Frustrated, yes. Flabbergasted, most definitely. But uncomfortable has never happened for you and I. And now you just make me feel… Safe. And… and Cared for. And… And… and Happy.”

“You… You really mean that?”

She responded by poking my nose and saying, “boop.”

I laughed. It wasn’t that funny, but… It was her. What else can I say?

I crooked my neck towards the front door and led her outside, holding it ajar for her as she struggled to keep her balance in those shoes. Going down the steps, the struggle became in vain, so I dove and broke the fall for her.

And then her lips were only an inch from mine again. “You’ve uh… you’ve really got to stop getting on top of me, Lil. People will talk.”

“You’re right,” she said, unmoving, forehead brushing mine. “Next time you can be on top instead.”

You ever feel your own cheeks go red? It’s fucking weird. But you know what’s weirder? When your dick gets so hard it physically fucking hurts! “Right,” I grunted, attempting to sit up in a way that wouldn’t put my boner into her belly. Again.

She made a look. I didn’t recognize it. I’d seen a lot of expressions on her, but never that one. She stood up and looked away from me, then stuck a hand into her purse and shoved her keys into my chest. “You should drive. My feet-“

“Yeah, yeah okay,” I said as my inner demons screeched at me for wasting another opportunity to roll her over, pin her down, and make my recent dream about anal sex into a glorious reality.

Yup, Special Hell. One way ticket. 

As I revved up her terrible, terrible car and backed us out of the driveway and onto the road, though, she surprised me yet again by asking, “How do I make you feel?”

“Uh… In what regard?”

“I mean… Do I ever make you uncomfortable?”

We came to a red light, because of course we did. I exhaled loudly. “No.”

“Are you sure?”

“Positive.”

“I mean I just… sometimes I worry that I’m hurting your chances of getting with someone else.”

“You don’t have to worry about that.”

“But-”

“I’m not looking at anyone else. We’re engaged.”

“Fake engaged.”

“So?” I said.

She frowned. “So you really haven’t been-“

“Nope.”

“Not even once? Not even with that milf at the country club yesterday?”

“Not since we started all this. Not since I put that rock on your finger,” I said.

“Why not? I mean, you were trying to fix me up with a girl today, so why aren’t you getting any for yourself?”

The light turned green. I’m sure there was a metaphor there, but Rose was always better at English than I was. I considered my words very carefully as I lowered my foot onto the gas. “Because… Because there’s not anyone who can give me what I want.” Except you. 

“And what you want is?”

You. In my bed. Wrapped around me. Screaming my name while your eyes roll back into your head and we ruin the linens. Not just once, but every fucking night until we’re old and gray- “I thought it was to whore around for the rest of my life.”

“And now?”

“Now I think I want something real. Someone to spend my life with.” Careful. CAREFUL. “Spending all this time with you has helped me realize that.” OH GOD NO-

“Thank you,” she said softly. Of course, everything about her was soft (other than her abs. Obviously)- her skin and her hips and her ass and her lips. “That’s very sweet of you. And, uh, likewise. I was never really sure if a long term relationship was in the cards for someone like me, but you… This… Us, it… It-“

“You don’t have to lie,” I cut her off.

“I’m not lying.”

“There’s no us, though,” I said, the words bitter on my tongue. No matter how much I wished there was an ‘us’ there would never be one-

“The fuck does that mean? I thought we were friends!”

Dammit. No, that came out wrong. “We are! Sorry, I didn’t realize that was what you meant.”

Town came into view, streetlights and old fashioned homes on both sides of the road. “Then what did you think I meant?”

“You do not want me to answer that.”

“Why not?”

“Because it’ll make you uncomfortable. And I just found out that I’ve yet to make you feel that way, and I’d really like to keep up my track record there.”

“Cris, what we established is that you don’t make me uncomfortable. That’s not something you can do,” Lily said as we drove past scores of couples and families walking the charming cobblestone streets and sidewalks.

“Yet. I haven’t done that to you yet. Trust me, if I answer this honestly, it will,” I said, my heart screaming in desperation as I held back a chorus of inner voices saying ‘tell her.’

“Cris. You’re doing it again. I thought I told you I wanted you unfiltered.”

“Dammit,” I grunted as the restaurant came into view. Someone had converted what was originally the only brownstone in town into a pizza place. Really shouldn’t have worked, but damn it was good. I pulled us into an open spot in the parking lot and turned off the car but didn’t loosen my hands from the wheel. 

“Cris,” Lily said, putting a hand on my arm and squeezing my tricep. Strong but precious was her grip- her in a nutshell, really. “I know there’s something you want to tell me, but think you shouldn’t. And I get you’re scared of hurting me, and I get the ever-present cloud of Catholic guilt you’ve got hanging over your all the time. But please. If you can respect me enough to only rescue me when I need it, you can respect me enough to be honest when I can take it. I need to know what’s going through your head. Are you… Are you having second thoughts? Do you want to stop this whole thing? Because we can get through this together if we just communicate- I’m… I’m not afraid to be vulnerable with you and I-”

I opened my mouth and started talking, because the alternative was developing a peptic ulcer on the spot. “Because, Lily, when you say things like that, sometimes I forget that this whole thing is supposed to be a charade. When you say things like ‘us’ it makes me think of a version of ‘us’ that’s more than friends. Because when you talk about us like you were just now, it makes me dream about a world where we’re actually dating. Because when you said ‘us’ it reminded me that we’re never going to be together. And that… For me, God help me, that hurts.”

“It… It hurts?” she said. “Why does it?”

“Why do you think?” I groaned as I knocked my skull back against the headrest, closing my eyes as tightly as possible.

“Are you saying you… That you-”

“I love you!” My eyes exploded open as I finally said the thing I was never allowed to say aloud, and God, as terrifying as the aftermath of it would inevitably be, it felt good to hear it outside of my own cranium. “Not like a friend. Not like a coworker. And sure as hell not like family. If I could have you as my real girlfriend, or as my real fucking fiance, I would. But I can’t. I know I can’t. I didn’t wanna say anything because I knew it would hurt you to hear it more than it hurts me to let it remain unsaid.”

She didn’t say anything. She didn’t blink. She didn’t take her hand off of my arm. 

“I’m sorry,” I continued. “That’s why I didn’t want to say it. I just want you to be happy, and me telling you this is not me making you-”

She kissed me. Only a peck on the lips, over in a blink. But it happened, and an angelic choir sang inside my head when it did. Her face hovered in front of mine, her touch lingering as one hand gripped my right arm and the other my left shoulder. She held onto me as if for dear life, and my back straightened and my erection filled my pants once again. 

“Thank you,” she whispered.

“For what?” I said. 

“For being honest,” she said, still hovering in front of me. “And for being a gentleman.”

“Uh… Sure. Anytime,” I managed. 

She let go, unbuckled her seatbelt, and then climbed out of the car and started towards the restaurant’s interior. “You coming?”

“Uh- right, right,” I said as I hurried after her. That was just a thank you. A gesture of appreciation, like the one on the cheek earlier, I reasoned. If anything, it was a pity-kiss. She gave me all she can bring herself to give me, so I can know a final taste of her before I die sad and alone in a hot tub full of money. That’s it. That’s all I’m ever gonna get. I have to be satisfied with it. And I WILL be satisfied with it.

We stepped inside the brownstone-turned-pizza place, where a host was set up at a podium inside the mudroom and showed us to a table on the rooftop. The brick oven took up the majority of the first floor, so there were private dining rooms inside the bedrooms on the second and then an open area on top. I managed to tuck my boner up into my underwear in stealth mode while I followed Lily and the host up the stairs to the roof, where we were sat at a metal table beneath an umbrella and an outdoor heating lamp. The waiter, naturally, brought a candle and put it between Lily and I. 

It was mostly couples on the roof. Gay, lesbian, straight, who the fuck knew- the whole damn rainbow was here. They were all lovey-dovey, holding hands, kissing. Meanwhile, Lily was locked into a thousand yard stare, probably from having just done what was no doubt to her the most disgusting thing imaginable. 

She shouldn’t have to deal with me and my bullshit. I never should have dragged her into my mess to begin with. She almost got really hurt last night because of my mess, because of my bullshit. I loved her, yeah, but if she actually returned my feelings, surely she’d say something. 

I had to make it up to her. I could still help her get laid. 

My eyes scanned the roof for a single woman, any single woman at all, until I found one: a tall, pale, gothic-looking girl with short black bangs and black lipstick and a spiked choker and a variety of piercings, clad in a lesbian pride flag tie-dye shirt. 

“Hey, Lily,” I said. 

“Yeah?” she said, evidently relieved to have her train of thought interrupted. 

“See that goth girl over there?”

“Yeah.”

“Do you think she’s hot?”

Lily looked her up and down, pursed her lips, and nodded. “Yeah.”

“Why don’t you go flirt with her. Maybe you’ll be luckier this time.”

“I’m not sure-”

“I can order us some pizza if the waiter comes,” I said. “You go get your lez on.”

She looked at me with wide, pained eyes, the sheer awkwardness of the situation choking out the oxygen in the area, before she breathed in through her nose and got up and went over to the goth girl. 

I breathed a sigh of relief as she sat down and introduced herself. This would all be fine. She’d get laid- because how couldn’t she, she looked like Lily DiGiacomo and had the personality of Lily DiGiacomo and just was Lily DiGiacomo, the most alluring and charming woman in all of God’s creation. It should be easy for her. 

I watched from over my menu… Until I saw Lily’s posture slump and tears fall out of her eyes while the goth girl patted her on the back and whispered to her in what I imagined was a reassuring tone. Oh, hell no!

I marched right over, steaming with anger, and said, “How dare you make her cry! Do you know who you just rejected? Only the most amazing woman I’ve ever met! What do you think you can do better? Not possible- better doesn’t exist!”

Lily kept on shriveling up while the goth girl blinked rapidly. Then she turned to Lily, stroked her hair tenderly, and said, “You know something, Lily? I don’t think you have anything to worry about; this whole display speaks for itself. And remember, no matter what you decide, you’re still valid and beautiful and definitely loved. Don’t be too hard on yourself, okay?”

Lily just moaned. Wait, what the fuck was going on here?

“Take good care of her,” the goth girl said, before Lily stood up and marched back to our table. “She’s in a sensitive place right now, I can tell.”

“Um… Sorry, what just happened?”

“Just go to her.”

“Right. Uh, thanks.”

“No problem, guy I just met!” she smiled. 

I went back to the table, sat down, and looked at Lily. She was still doing a thousand-yard stare as the waiter approached our table.