A Beginner's Guide to Gold Digging: Chapter 13

A Beginner's Guide to Strategic Exits

Crispin

18 Hours Earlier

“Hey,” Sarah O’Neil said as she approached me, every ounce as beautiful as when I’d last laid eyes on her. 

“Uh… Hi,” I said, putting down my phone and standing up straight, a cold, metallic clamp gripping my spine. “Been a while.”

“It has,” Sarah said. “Can we talk?”

A torrent of memories struck me: at this very country club, nearly a decade earlier, this woman, drunken and heartbroken, had sat at a table alone upstairs. She was sobbing her eyes out over a half-empty bottle of vodka, and she’d looked like she wanted to die. 

I’d only interacted with Rose’s eldest sister a handful of times. She was beautiful, and I’d nursed a passive crush from afar at one point, but that was all it was. As I’d approached her, asking what was wrong, if there was anything I could do to help, she’d…

She’d come on to me. Still wearing her wedding ring, looking like guilt was eating her alive, she’d solicited me for sex. Hadn’t even been subtle about it: she’d fisted my shirt and said she wanted me, needed me, and… 

And I’d run away. 

` From her. From my best friend. From my own reputation. 

“Sure,” I said. Lily needed space. She was… I’d fucked up. I’d managed to do the thing I wasn’t supposed to do again because… Because I guess I thought it was my job to protect her, even when she didn’t need protecting. And she didn’t, at least not from Karen of all people. I may have found my stepmother annoying, but she would never put Lily in legitimate danger. Either way, my fiance needed to cool off. Somehow, I didn’t think today would be an appropriate time to tell her how I felt anymore. 

“So,” Sarah said, “I don’t know how much Rose has told you about… Everything that went down with our family in the past few months.”

“Everything,” I said. “She told me everything.”

“Okay. That makes sense,” Sarah said. “Then you… You have context for… For why I did that thing that I did. But that doesn’t make it okay. In fact, I think it’s one of the worst things I’ve done. Not the absolute worst- turning on my sisters, abandoning them, is the worst- but it still wasn’t good. You were… God, you were barely more than a kid when it happened, and I practically threw myself at you, and I… I feel disgusting. I’ve felt disgusting for a very long time. But I’ve been too afraid to say anything because… Well, because I’m a coward. And I always have been. But I want to change that. So, I’m sorry.”

I ran a hand through my hair. She… I… “I forgive you.”
Her jaw dropped. “Just… Just like that?”

“Just like that,” I nodded. “Because honestly… I feel guilty too.”

“What do you have to feel guilty about?”

“I abandoned my best friend,” I said flatly. “Rose and I… We’d been drifting for a few years by that point. And I wanted to tell her about what happened, but… She idolized you, Sarah. I couldn’t bring myself to say it. So I’m a coward too. Everything thinks… Everyone says I’m a guy with no filter, but when it counts, I avoid the hard conversations.”

“It takes two to tango, you know?” Sarah said, leaning back against the wall as she stood next to me. “Rose could have sought you out, forced the conversation to happen.”

“Yeah, I guess she could have. Guess it makes more sense now. There was a conversation she was avoiding having with me as well.”

“About her being trans or about her having a crush on you?” Sarah said. 

“Both, probably,” I shrugged. “Also, was it really that obvious to everyone besides me?”

“Yes,” Sarah said. “Honestly, I… I was afraid you would be what got her to take the next step. To come back out, be her real self.”

“Is that… Is that why you picked me?”

“No, I picked you because you were there in front of me,” Sarah said. 

“That honestly makes me feel better, so thank you,” I sighed. “Kyle is a lucky guy.”

“Yeah,” Sarah grimaced. “He definitely is.”

I saw Lily ascending the stairs with my sisters, probably heading back to the mansion for the afterparty. “How do you do it?” I asked. “How do you find the right words? How do you bring yourself to say something you’ve convinced yourself that you shouldn’t ever say?”

“Uh… Well, I started therapy earlier this week, and we figured that a way for me to live with all the guilt and shame was an apology tour-”

“No, I mean… How do you bring yourself to have a conversation that you know will change the way the other person looks at you?”

She crooked a curious smile at me. “We’re not still talking about Rose, right? Because while in another life you two would have been adorable-”

“In another life, Rose and I might have also dated for a month and then broke up and still wound up not talking for a decade,” I said. “And no, I’m not talking about her. There’s… There’s this other girl. Lily. She just left actually, but… I…”

“Do you love her?” Sarah asked. 

“... Maybe. I’m not sure. I’ve never… I’ve only had a couple of long term girlfriends. I’ve never let anything get serious for me before. I’ve never wanted anything serious before. It’s all just so complicated.”

“Why?”

I chuckled. “How long you got?”

“As much time as you need,” Sarah said. 

I smiled. And I told her. I’d already seen her at her most vulnerable, so why not return the favor. Every last detail of the story of Lily and I became known to Sarah O’Neil. 

By the time I was done, Sarah was flagging down a server and gulping a flute of champagne. I did the same myself. 

“God, that is complicated,” Sarah said. “You realize she’s most likely bi, right? Just hasn’t accepted it yet?”

“Then why did she get so grossed out by-”

“Because you were in public, dummy,” Sarah said, brushing her bangs out of her eyes. “Plus… Look, I’m bi as well. And I came at it from a different angle- it took me longer to realize I like girls than guys- but still… When everyone, everything, is constantly trying to get you to be one thing or the other, the idea that you’re allowed to be both can be slow to register.”

“That makes a depressing amount of sense.”

“Yeah. So I guess the question is less about whether or not she’s gay and more about whether or not she returns your feelings.”

“Yeah,” I nodded. “Should I tell her?”

“I can’t answer that question for you, Crispin,” Sarah said with a sad smile. “But I can ask you this: can you live in the reality where it remains forever unsaid?”

Now

I awoke from a very pleasant dream about anal sex to the feeling of a curvy, delicately feminine frame clinging to me. My first thought, before I even opened my eyes, was oh fuck, did I cheat on Lily? Fuck, okay, no, no, you are NOT gonna be That Guy. The relationship is fake but the commitment is real, at least for the time being. If you did… Then you go to Confession and beg forgiveness, because that’s the right thing to do in that situation. You are NOT gonna be That Guy, and if you have to prostrate yourself before God and before Lily as well to ensure you don’t become That Guy, you’ll do it.

God, I felt disgusting. And sore. I drew a deep breath through my nose as I slowly opened my eyes to face the music… And then opened them very wide very quickly as I registered that it was Lily draped around me. It was Lily in bed with me. It was Lily who had…

Had tended my wounds last night. Who’d stayed with me all night to make sure I was okay. Who was moaning softly into the crook of my neck. 

I tried to will my morning wood to go down. Oh, God, she was gonna be mortified when she woke up, mortified and embarrassed and probably disgusted. And all I could think about was her hands running over my shirtless chest, of her foot between my legs and skimming the inside as she made her way up to my groin, of her lips pressing against my neck and shoulder and mouth. And suddenly, that sex dream I’d been having registered for me much more clearly. 

As the highlight reel played in the theater of my mind, I forced myself to imagine a priest walking up and dumping a bucket of ice-cold Holy Water onto my dick. Do not. Get. Carried. Away, I told myself. She just had to deal with that shit last night, just had to deal with some straight guy being gross around her. Now stop being horny for your fake fiance!

Of course, that was a little hard when she rolled over in her sleep and wound up quite literally on top of me.

Well, shit. Do I… Do I move? Do I wake her up?

She muttered something under her breath, something about how she’d never tried something like this before, and my cock somehow grew harder and started pressing against her stomach. At which point, her eyes opened, and her face was an inch above mine, and her mouth was curved into that gorgeous smile of hers. 

Kiss her, my libido screamed at me. Kiss her, kiss her, kiss her, shove your tongue down her throat ,grab her hips and pin her beneath you and ride her, kiss her, kiss her, kiss her, cup her breasts, pinch her nipples, bite her shoulder, kiss her kiss her kiss her-

She blinked. “Good morning,” she said in a tiny voice, her smile shrinking but not vanishing. 

“Uh… Hi,” I said. 

“I must’ve fallen asleep in here,” said Lily, who either didn’t register the fact that she was on top of me or that our lips only had a few inches of air between them or that my erection was stabbing her in the six-pack again or, more likely, was politely pretending not to notice. 

Because that’s what friends do, apparently. 

“Guess so,” I said, wondering how red my cheeks were. Very, if I had to guess. 

“How are you feeling?” she said. 

“Good,” I squeaked. 

“Oh, uh, I’m top of you, aren’t I?” she said, as if finally registering where she was. 

AAAAAHHHHHHHHHHHHH! “Yeah, angel, you are. You, uh, wanna maybe get off?” Oh Goddammit why did I say it like that?!

Her smile died, then. Her face shifted back to what she apparently assumed was her default setting of ‘grumpy’ as her eyes narrowed a bit and she rolled off of my chest. Made sense: the sheer proximity to my embarrassed ass had probably been amusing until the early morning brain fog began to clear, and now her sheer disgust at the situation was taking over. 

I kept waiting for her to defuse it with a joke, possibly about the size of my morning wood, and I could reply with some lame comeback, and we could reassert the equilibrium of our deeply weird relationship. But it never came. She simply sat on the edge of her side of the bed, legs hanging off, and stared directly forward.

Oh, God. I’d really done it now. “Hey, uh… I’m really sorry about all this, but I swear, nothing happened-”

She laughed, and it sounded oddly bitter. “Relax, Cris, I know you would never do that to me. I know you’re not that kind of guy.”

“Y… You do?” I said as I sat up.

“Yeah,” she said, her shoulders slumped, still not looking. “Honestly, I feel like I should be apologizing to you. The last thing you want is to wake up to me clinging to you-”

Um, not really? Initial shock notwithstanding, it was pretty dope. 

“-And I just… I feel embarrassed,” Lily continued. “Like I crossed a line. I should have left once I got tired instead of just assuming I could sleep with you.”

Why would YOU say it like that? I whined internally. “It’s all good,” I managed to get out without stammering.

“Are you sure?” She said, still with her back to me.

I got out of bed, still in my khakis, still not wearing a shirt. I walked over to her, and found her beautiful (stop it) face smeared with yesterday’s makeup and her beautiful (STOP IT) eyes watering. “I’m sure,” I said. “And… Thank you. For taking care of me last night. You didn’t have to do that-”

“Yeah I did,” she said instantly. “You’re my best friend.”

“Well then thank you regardless. And, uh, you’re my best friend, too.”

She winced when I said that. Figured. I’d made it weird by saying it.

Awkward silence occupied the room like a foreign army. We both looked at each other like there was something we wanted to say but wouldn’t let ourselves. 

“Uh… do you think one of your sisters would loan me some makeup wipes?” Lily asked, hands gripping her knees, posture still slumped. “I didn’t bring any.”

This was a good start. Not much, but a start. “Do you one better- I got some in my medicine cabinet.”

She quirked an eyebrow at me. “You keep makeup wipes in your bathroom?”

I shrugged. “I like to be prepared for whatever any of my overnight guests need. I also keep a box of tampons in there.”

She laughed, revealing her dimples, as she pushed aside a lock of curly brown hair. “I don’t think I need those.”

“Fair.”

“Though I suppose I could’ve plugged up your bloody nose with them last night.”

“Hah,” I said in monotone. “Go get cleaned up. Take a shower if you want- I got extra towels in there too, plus some ladies body wash. Though I imagine you just wanna use mine.”

“Why? Is me smelling like you a fantasy of yours?” she said, dimpling further as her grin turned shit-eating. 

“I can honestly say that no, it isn’t,” I replied. Hopefully it would cool the fire a bit for me as well. “I’ll rustle up some breakfast for us.”

“Okay,” she said softly. Had her voice always been that breathy? 

I left her to her devices, tossing on a baggy Soundgarden t-shirt and ambling downstairs to the kitchen. The place was empty but for the help, in the midst of cleaning up the remnants of Claudia’s party. “Morning, Juanita,” I said as I passed her by scrubbing at a stain on the tile floor. One that was most likely… My blood. “You, uh, need any help with that? It is my fault, after all.”

“That’s alright, Crispin,” the older lady smiled. “Honestly I’m too impressed to be annoyed.”

“Impressed with what?” I raised an eyebrow.

“Your display of chivalry. We’re all talking about it.”

“I mean… I kinda acted like a caveman,” I said as I scratched at the back of my head. 

“Not how Miss Lily was looking at you when it happened, at least from what Trevor saw,” Juanita grinned. “He said she was looking at you like you were her knight in shining armor.”

Then it was my turn to give a bitter laugh. Yeah, maybe in my dreams. My inappropriate, non-platonic dreams involving, amongst other things, anal sex. And oral. And titty-fucking. “You eat yet? Want breakfast?”

“I’m all set,” Juanita said. “You just spend the long weekend with your fiancé, alright? I like this one. She’s good for you.”

“Too good for me is more like it,” I sighed as I stuck my hands into my pockets and entered the kitchen.

I turned on the stove beneath a clean skillet, poured on a splash of olive oil, and grabbed the carton of eggs and a sleeve of sliced ham and a bag of shredded cheese from the fridge. I mixed them together in a bowl before pouring it onto the now sizzling skillet and watched the scramble cook as I waited patiently while holding a wooden spoon. 

“Is that for me?” Lydia’s voice reached me. I turned to see her entering the kitchen in a black and pink kimono, dark hair pulled back in a loose ponytail.

“‘Fraid not,” I said. 

She peered over the skillet. “Lotta food for just you.”

“It’s uh, well it’s also for Lily.”

“Aww, that’s cute,” Lydia said. And then her eyes went wide with fear. “Wait. WAIT. Lily is coming here? Now?”

“Actually, she’s already here,” I said. “Taking a shower right now, in my bathroom.”

“Shit,” Lydia said. “Okay, I’m gonna stall for you, but you and her both need to get out here like right this second!”

“What? Why?”

“Dad and Karen came home last night,” Lydia said. “Got in around 2 AM. Dad is pissed at you for getting into a fight with Chuck-”

“Chuck had it coming,” I glared.

“And I agree with you on that, but Dad doesn’t.”

“I’m not allowed to defend my fiancé from a fucking pervert?” I said, fists gathering.

“Not when he was about to close a deal with Chuck’s dad.”

“Fuck,” I said.

“Yeah. If it were just you, I’d say it’s better to weather the storm, but I don’t think I need to explain to you why you don’t want that poor girl to have to feel the wrath.” 

“FUCK!” I shouted. “Uh… The food is all yours. I guess I can stay at her place for the rest of the weekend-”

“That’s the first place he’ll think to look for you!”

I ran a hand through my hair. Shit. Rose and Kyle were going to Maine for the rest of the weekend to visit Kyle’s family, so we couldn’t hide out with them. Julia had an ‘overnight guest’, meaning the proverbial sock was on her door knob. And I didn’t know Lisa and Rachel nearly well enough to impose. Goddammit, Goddammit, God-fucking-dammit. “Okay, new plan. Tell him Lily and I went to her place. I’ll think of somewhere else to wait out the storm.”

My oldest sister nodded and gave me a quick hug before I dashed off.

By the time I got to my room, Lily was stepping out of the shower with a towel around her waist. Which… Holy shit, her boobs were… were… They hadn’t always been that big, right? That round? No, no time for that right now. Focus!

“Knock much?” She said, face furiously red.

“Get dressed,” I said, tossing her the dress she’d discarded on my carpeted floor. 

“Uh… Isn’t this the part where you’re like ‘it’s my room, DiGiacomo, I come when I-”

Hating myself even as I reveled in touching her bare shoulders, I grabbed her and said, “Lily, I’m serious. We need to go. Right now. My dad is on the warpath, and you do not wanna get caught up in that.”

“Oookay then. Uh, fair enough. Just one question: go where?” She said, looking away as her grip on her towel tightened.

I  reluctantly let her go and grabbed my suitcase from my closet, trying my best to give her a reassuring grin. “Let’s get out of town for a few days. We’ll pick up your stuff on the way. Rob can feed Void and water your plants for the weekend, right?”

Her eyes darted back and forth, clearly apprehensive about all this. But she finally nodded in agreement. I ran into the bathroom to brush my teeth and throw together some supplies, and by the time I was out, she was dressed and putting clothes into my suitcase for me. 

 ***

The drive out to Cape Cod took a little over two hours, by which point my greatest fears were confirmed: I was in love. She’d spent the ride being wicked nice to me, which started mildly disconcerting before slowly winding up feeling great. 

“You seem stressed.” “Do your injuries hurt?” Innocent enough. But then it started shifting: “Is there anything I can do to take the edge off for you?” “Tell me what will make you happy.” “Who do you need me to be right now?”

It all kept putting images in my brain. 

And then she’d… She’d… She’d put on grunge music and started singing along with it and playing air guitar! It was fucking adorable! It was so adorable that I wound up singing along with her for the entirety of Nirvana’s In Utero!

It also didn’t help that she’d changed clothes while we stopped at her place, and that she’d put on a red sundress with a golden floral pattern and a slit running up her leg. It stopped at mid-thigh and offered a generous view of her plunging neckline. I’d never seen that dress before; it wasn’t one of the ones I’d bought for her on our first shopping trip, so where the hell had she gotten it? 

“Does it look okay?” she’d asked, and she’d been so fucking nervous when she’d asked it, and I got that: it wasn’t just for the bit, she really had changed her presenatation. I had three sisters and I actually listened when women talked to me: I knew how big a deal it was when most girls did that. I didn’t fully understand it, but I had it on good authority it was very often nerve-wracking. And for a trans girl, that was probably even more so. And because I’m an idiot, I responded, slack-jawed and wide-eyed and overheated, with, “It looks gorgeous on you.”

God, that dress, that fucking dress. I couldn’t handle it. She looked too good in it. Made me want to tear it off of her, flip her over onto her stomach, pin her down and-

“You brought me to your family’s beach house?” Lily said, blinking rapidly and taking in the scenery. Three story house, painted the same red as her dress (serendipity is a real asshole), right on the water and with a mostly private swath of beach as its backyard- I couldn’t exactly blame her for the dropped jaw.

Damn, her mouth could open real wide. Could probably fit my entire-

“Yeah. I mean, I did tell you to bring a bathing suit,” I said, trying to imagine the cold ocean water around my groin. 

“Won’t your dad think to look for it here?” 

“No, he hates coming here. Reminds him too much of Mom… and Karen knows it, so she doesn’t like it here either.”

“Ahhh.”

“Yeah, so, historically when I do something like this, I’m hiding out at one of my college buddies’ houses,” I said as I climbed out of her old, beaten-up, barely street-legal mustang, then ran over to the other side to open Lily’s driver side door for her.

She sat there, looking up at me. “Aren’t you gonna offer me your hand?” 

“Uh… Don’t you usually want me to ask first?”

“I think after this morning we’re past that point,” she said, facing me, giving me a clear view of her cleavage. Fuck, that was a valley I could get lost in. “Besides, I don’t mind if it’s someone I trust.”

“You… You trust me?”

“Of course I do,” she said, holding out a hand. “You’re my fiancé.”

I grinned, even as I reminded myself not to betray that trust under any circumstances. Yes, we were at the place where my father had proposed to my mother, yes it was hot and the ocean was right there, and yes we were here by ourselves, but I would not be That Guy. 

So, I took her hand. “You take this all very seriously.”

“I take everything seriously,” she said as she gripped my hand and stood up, her boobs bouncing inside the confines of that fucking dress. 

“You do. It’s very charming,” I said before I could stop myself. 

“Oh? I’m charming now?” She said as she pulled me towards the trunk of her alleged car and opened it.

“I mean… Yeah,” I said as I grabbed my bag and hers and one-fisted both of them. 

“Wow, so I’m beautiful and I’m charming,” she said, with that bioluminescent smile. 

“I mean, yeah? Have you met you?” I said, thinking nothing of it. This was fine- it would help build up her confidence and make things easier for whatever lucky girl she wound up finger-banging for the rest of her life. She wouldn’t want to be with me after last night, after this morning, after she’d gotten a real look at what being around me long-term was like. My family and their ridiculous bullshit and our so-called friends acting like sociopathic parasites all the time. She deserved better than what I could give her. Maybe, eventually, I could come clean about how I felt, but right now… Right now, the idea just didn’t feel right.

She giggled. Because I guess that was a thing she did now. Fuck, it was like an auditory aphrodisiac. “Careful, douchebag, or I might get the impression you actually like me.”

Say it say it say it- I wanted to. I really wanted to say it. But I didn’t let myself. So instead, as I led the two of us up the front steps, I gave a lame chuckle befitting of a brace-faced teenager and said, “Yeah, I mean… Can you imagine?”

Her smile died again. Dammit. What did I say? I thought we were trading barbs?! “No, I really can’t,” she sighed.

A silence infinitely more suffocating than the one we’d suffered earlier saturated the air. After a few minutes of staring at her, I managed to form a coherent thought in the form of ‘I should probably unlock the door.’

But to do that, I needed a spare hand… At which point I realized the one not gripping our luggage was still intertwined with Lily’s delicate yet calloused fingers. 

She seemed to realize it too, because she kept staring at it. 

Another thirty seconds died torturously before she peeled her hand out of mine. “I should let you have that back so we can go inside.”

“Right,” I choked out as my brain started showing me images of her taking that hand and sticking it down my pants and gripping my throbbing dick and-

I shook my head as I unlocked the door and beckoned her inside.