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A Beginner's Guide to Gold Digging: Chapter 26
🕑 Added 2025-08-11 16:31:50 +0000 UTCA Beginner's Guide to Reconciliation
Lily
Two Days Later
I sat in my therapist’s office, staring at the ceiling, squeezing a stress-ball over and over again.
“So,” Dr. Pamela said, sitting across from me, “What happened?”
I told her, sparing not a single agonizing detail of the evening. It took nearly twenty-five minutes, but when it was over, it was out there. I’d told someone. Told how I’d given the man I love a panic attack in the middle of sex. Ugh.
“I see,” the good doctor replied. “And then what happened?”
“He spent the night staring at the wall, was silent the entire trip back home, and when I tried to check in with him before he left for work this morning, he just said he wasn’t ready to talk about it,” I answered.
“But you know what it’s about?”
“I know exactly what it’s about,” I nodded, my hand beginning to cramp from overusing the stress-ball. “I just wish he would talk to me. It’s so obvious what’s going on, and I want to apologize, but then when I try he’s all like ‘you haven’t done anything wrong, this is my fault’ and I can’t decide if that’s reassuring or infuriating.”
“Do you think it’s his fault?”
“No, it’s my fault!” I said, throwing the stress-ball to the floor. It immediately bounced back up and bonked me on the forehead. “Ow.”
“Why do you think it’s your fault?”
“Because I said the thing I wasn’t supposed to say!” I groaned. “Me and my stupid libido making everything worse again, making him uncomfortable, stepping over his boundaries… Why are you grinning? What about this is comical?”
“I just think it’s a little ironic, given he’s definitely had all of these thoughts about you.”
“I… That’s…”
“Lily,” she said, leaning forward in her chair, “Come on. The first thing you told me about this man is that he’s filtering himself around you because he’s scared of being disrespectful or hurting you. During your joint session together, he even said he spent the early parts of knowing you going out of his way to think about everything he said around you a million times before he said it out loud.”
“So now the tables have turned,” I said, gripping the stress-ball once again. “I did the thing he was scared of doing himself, and now he’s mad at me-”
“Why do you think he’s mad at you? Does he seem mad?”
“... No, no he doesn’t,” I said, putting the stress-ball down and rubbing my temples. “He seems like he’s just ashamed of himself. Like he feels dirty because of how much he enjoyed… How much he enjoys being with me. How much he enjoys doing things like what we did together. He’s… Oh, God. Oh Goddammit.”
Dr. Pamela raised an eyebrow. “Yes?”
“He liked it! He liked it when I said the thing! That’s what’s eating at him! He hates that he likes it, because it’s not… Not what he’s supposed to be! Holy shit! Holy fucking shit! He… He and I are the same,” I said, lying down on the couch and staring wide-eyed at the ceiling. “Heh. We really are made for each other, aren’t we?”
“You might very well be,” she said. “Let’s test that, real quick. I want you to do a little visualization for me right now, okay? Just picture yourself in ten years. You’re getting home from work. Who’s waiting for you at home?”
I nodded, and I closed my eyes, and I saw the future:
I’m driving home after a long day at work, sweaty and exhausted and desperate for a shower. I pull into the driveway, and… And Cris pulls in at the same time. His hair has started graying, salt mixed generously with pepper, and there’s a few lines on his face now. They make him look distinguished, almost regal. He climbs out of his car and before he does anything else he kisses me like I’m still the most precious thing in the world to him. And all the exhaustion and stress evaporates from my body, and I slide into him immediately. We cling to each other, arm in arm as we walk inside. We make love in the shower and cook dinner together, and by the time it’s done, there’s a knock on our door.
Julia is on the other side, and she’s holding hands with a toddler. A little girl with Cris’ eyes and hair, and she runs towards me and calls me momma and jumps into my arms and I smile. Julia waves good-bye, her day of babysitting done, and Cris and our daughter look at me with so much love in their eyes that I know this is it. I know this is how I want my life to look.
I have a funny feeling Cris wants it to look like this too.
“Oh shit, I want kids,” I said as my eyes shot open.
“Hm?”
“Or at least, I want them with Cris. I want… Oh God, I wanna build something with him. I wanna come home to him every day. I… I wanna shoulder all our burdens together!” I said.
“Including this one? Even if you’re worried he’s hurting because of something you said?”
“Yes, especially this one! Because it’s one I’ve dealt with, or at least I’ve dealt with something like,” I said. “And it’s not… Oh shit, it’s not really about me!”
“Then who is it about?”
I blinked rapidly, then realized my mind conjured an image of a specific babysitter for a reason. “I need to make a call. Two calls, actually- can I make two calls?”
“By all means.”
I started by pulling out my phone and dialing Rose. “Hey! Uh, just wondering- is Cris still at the office?”
“He left early,” Rose said on the other end. “I’m only just heading out myself. Is everything okay with you two? He seemed like he was only half-present most of the day.”
“It’s… It’s complicated. I need your help with something. Do you know where Cris goes when he’s grappling with guilt and shame and existential despair?”
“... I’ll text you the address and meet you there.”
Crispin
My legs bunched up against my knees as I stared at the tombstone. ‘Eleanor Sullivan-Winfield, beloved wife and mother’ etched into slate, stared back at me. I sat in the shadow of the church we’d gone to growing up, the one my mom always took us too, the one where she’d brought me every Friday night to make food for homeless people, the one where she’d spent summers organizing affordable housing builds out in rural Massachusetts, the one where she held fundraisers for cancer research, the one where she’d taught CCD, the one where she’d organized bake sales and potlucks and introduced me and Priscilla and Lydia to everyone she knew as the lights of her life.
She hadn’t been perfect. I knew that, at least intellectually. She wasn’t perfect, and neither was Lily, and neither was I. But I could be better, and lately… Maybe I hadn’t been. Maybe I’d fallen far, far short of who I was supposed to be.
I needed to talk to Lily about how I was feeling, but every time I tried, the words got lodged in my throat and a glacier of shame ran roughshod through my soul.
Footsteps approached over gravel from behind me, then softly stepped onto the grass. A familiar face sat down next to me. “Hey, bestie,” Julia said, looking straight ahead.
“Hi,” I said. “What are you doing here?”
“I knew you were here and figured you’d need the company.”
“I see. Is Rose-”
“Right here, my dude,” Rose said, also sitting down next to me and facing forward.
“Oh, Jesus. Lily put you up to this, didn’t she?” I said, rubbing my face with my hands.
“Got it in one,” Julia said.
“Is she here?” I said, turning my head back to look for her. Julia, however, grabbed me by the face and pointed me towards the grave again. “Jules, what the hell?”
“We’re having a long overdue conversation right now, Winfield,” Julia said flatly.
“Indeed we are,” Rose said.
I grunted. “And what conversation is that?”
“The one where I tell you to stop beating yourself up over something that happened nearly a decade and a half ago,” Julia said.
The glacier carved up the lining of my soul. Fuck. Fucking fuckity fuck fuck-
“And the one where I tell you to stop feeling guilty for not being a mind-reader,” Rose said.
“Okay, now I’m lost,” I said, eyes darting between my friends on either side of me.
“God, you’re dense,” Julia rolled her eyes.
“It is a very good thing you’re pretty,” Rose said.
“Uh… Is this supposed to be a pep-talk? Because if it is-”
“It’s not a pep-talk, it’s a call-out,” Rose said.
“Okay?”
“Cris,” Julia said, “I really need you to understand something right now: what happened between us wasn’t actually about you. It was about me and my bullshit, about this bizarre compulsion I felt to put myself in a box that did not fit me at all. I used you. I fucked up. But you never let me apologize. And because of that, I’ve spent nearly a decade and a half lugging around my own metric-ton of Catholic guilt. And I know why you did that.”
I grunted, the chafing inside me growing harsher every second. “Why did I do that, Julia?”
“Because you put women up on pedestals, bud,” Julia said. “You have done that as long as I’ve known you. And you’re not nearly as bad about it as most guys who do that, but it’s still not good, because when you do that, when you refuse to live in the world where women are flawed and messy and capable of hurting you without meaning to, that’s denying them agency and autonomy. That’s still acting like you have full responsibility for everything the women around you do. And it’s fucked up.”
I blinked, and I wanted to find some outraged, baffled part of me to tell her that was stupid, that obviously it was my fault, but all I could find was a mental image of me self-flagellating. “Alright,” I nodded, “That’s probably true. Certainly sounds like me. So then… Let’s hear that apology, Henderson.”
She smiled, and for half a second I remembered why I’d fallen so hard for her as a kid. But then I thought ‘I like Lily’s smile better.’ And that was okay. That was a good thing. “Crispin, I am sorry that I took advantage of your feelings for me in order to confirm something I already knew about myself. It was wrong, and I should’ve just done what I actually wanted to do and gone to prom with the captain of the girl’s wrestling team.”
Something wet blurred my vision, and this sense of lightness overtook me, like I’d had a twenty-pound weight strapped to my back and it was suddenly cut loose and unburdened from me. “I forgive you,” I said.
She kissed my cheek and rested her head on my shoulder. “Good. Rose, your turn.”
Rose breathed in deep. “Cris. You didn’t abandon me. I abandoned you.”
“What?” I said, genuinely aghast this time.
“Sarah told me about the conversation you two had on Fourth of July,” Rose said. “You think that because my toxic family drove you away, it’s your fault I was alone for a long time. And maybe you could’ve reached out more, but I can personally guarantee that at that point, I would’ve pushed you away regardless. I was in a lot of pain, but I never told you about any of it. You had no way of knowing. And yeah, I was in love with you, but I didn’t want you to save me. I needed to save myself. And I did. And at the end of the day, I have no regrets, because I became who I was meant to be and met the love of my life and I’m happier than I’ve ever been. And so did you. So I think things shook out pretty darn well.”
“Yeah, none of us were meant to be romantically involved with each other,” Julia said. “We were just… Kids going through it. And we had each other. And then we didn’t. But now we have each other again, and I think that’s fucking awesome.”
“So, while I can’t apologize for driving you away, I can absolutely apologize for not holding on tighter,” Rose said, resting her head on my shoulder now. “I’m sorry.”
“I forgive you,” I said, and another weight was taken off of me.
“Good,” Rose said.
“Can I talk to my wife now, please?” I sighed.
“She’s not your wife yet, loverboy,” Julia chuckled.
“I dunno, I’m in favor of trying it out now, seeing how it sounds,” Lily’s voice carried across the cemetery. I turned around, and I saw her, wearing that red and gold sundress Rose picked out for her, the one that she loved so damn much, that I loved seeing her in so damn much. She stepped out of her high heels as she reached the grass, walking barefoot over to us, hips swaying and curls blowing about in the last of the summer winds. Her plump, red lips parted as she stood over us and said, “It’s like when you met my folks: I’ll have you for a husband, if you’ll have me for a wife.”
“God, you’re beautiful,” I said as my heart threatened to shatter every last one of my ribs through sheer manic pounding.
And then, of course, she giggled.
“I think that’s our cue to leave,” Rose said to Julia.
“Probably a smart idea, yeah,” Julia said.
They both stood up, hugging Lily and waving good-bye to me.
Lily sat down, smoothing the hem of her dress and looking at the grave. “It’s nice to meet you, Mrs. Winfield. I’ve heard a lot about you. I don’t know what Cris has told you, but please know, I love your son more than I’ve ever loved anyone, anything else in my life. He makes me feel alive. Seen. Beautiful. And I want to marry him, to spend my life with him, to cherish him. He’s everything to me.”
I put a hand on her knee and said, “She says… She says to call her Eleanor.”
“Does she, now?”
“She does,” I smiled. “She also says that I’ve told her… Everything I know about you already. That I came here the day after we first met to tell her about you.”
“Really? And what did you tell her?”
“That I was annoyed at myself for making you uncomfortable,” I said, gathering her fingers around mine. “That I hoped we could still be friends. Then a few weeks later, I came back and told her I had a crush on you, that you were the funniest, coolest, most ridiculous person I’d ever met, but that I hated myself for wanting you.”
“And after we got engaged?”
“I told her I was down bad, that I didn’t wanna lose you as a friend but I was starting to wonder if maybe there could be more here after all. That I didn’t know whether or not to pull the trigger because I was… Because I’m a coward.”
“You’re not a coward, Crispin,” she said, running her fingers over the back of my hand. “You did what you thought was right. Honestly, I’m amazed you’ve put up with me as long as you have, when I keep pushing you to do things that make you uncomfortable.”
“Lily-”
“Please, just let me… Let me say it, okay?”
I nodded.
“I’m sorry for saying what I said,” she whispered, putting her chin on my shoulder. “I should have known how you would react.”
“I forgive you,” I said, and one more weight was released from my burden. “But I still shouldn’t have reacted the way I did.”
“Yes, but not for the reason you think.”
I furrowed my brow. “What does that mean?”
“When I said those three words to you,” she said, a coy mischievous grin forming on her cherry-red lips, “I don’t think it was just that you were afraid of being That Guy. I think you were freaked out by how much you liked it. How much the idea turned you on. I know because I went through something pretty similar. Something about… Liking something that fucks with your sense of self. Something that, in the wrong context, would be morally horrifying.”
I wanted to shrivel up, dissolve into the acid of my own shame. But she stood over me, offering me a hand up, wanting to take me back into the warmth and the light.
Of course she was. She was my angel.
“Yeah,” I said, tensing up for a second before finally, FINALLY, the last weight tying me down was cast aside. I sat up straight, and I put my arm around Lily’s waist and held her as close as possible. “You’re absolutely right.”
“If it helps at all, the fact that you’re so reluctant to admit that… That’s how I know you’re a good one. How I know you’re not That Guy. That you’re just a bit naughty,” Lily said, the grooves her hips settling against me. “Fortunately for you, so am I. Dahling.”
A deep, relieved laugh popped out of me. “Damn right.”
“Honestly, considering how slutty you are, I’m surprised it was so hard for you to admit,” Lily said. “But then again, I’m apparently the first girl to ever ask you how you wanted it.”
“Hey, I’m the first guy to ever ask you that too,” I said.
“You’re my first guy in a lot of ways, Winfield,” she grinned. “And I am so fucking glad it was you. You have no idea how happy that makes me. I only have one regret.”
“What’s that?”
“I wish I could have admitted it to myself sooner,” Lily sighed. “Like, ‘on the day we first met’ sooner. Just felt what I felt for you and let it guide me forward. We could’ve… We could’ve been friends faster. Could’ve been together faster. Just… I could’ve just gotten to know you, like I know you now, while I got to know myself.”
“There’s still plenty for us to learn about each other,” I pointed out. “You still haven’t told me when your birthday is.”
“Oh God, I haven’t. And I don’t know yours, either!”
“Holy shit.”
“Indeed,” she laughed. “Uh, well, mine is October 23rd.”
“You’re shitting me,” I balked.
“No. Why-”
“Lily, my birthday is October 23rd as well.”
She palmed her face with both hands and half-groaned half-laughed. “Fucking dammit; we’ve had the same birthday this entire time and not known it?!”
“Looks like it,” I said, kissing the crown of her curls.
“What else do we still need to know?”
“Uh… Hmm… I’m allergic to penicillin.”
“Good to know,” she nodded. “I hate bananas. Like, I really fucking hate bananas. They taste so bad, and the texture is horrible.”
“Will never make you banana bread, gotcha,” I said. “More pertinently… You’re not the first trans girl I’ve been with. You’re the first one I’ve ever been serious about, though.”
“How many others?” she said, eyebrow raised and a good-natured smile on her face.
“Two,” I said. “One was a hookup I met at a bar three years ago. She hit it and quit it.”
“And the other?”
“A fuck-buddy from college,” I said. “We banged a couple times but didn’t really have much in common so neither of us ever pushed for more.”
“I see, I see. Uh… I think I had a crush on my friend Kevin growing up but didn’t realize it?” Lily said.
“Kevin, who outed you to your entire school?”
“Yeah, some mistakes were made,” she grimaced. Then she kissed my cheek. “I’ve traded way up, though.”
“Fuck yeah, you have. Anything else? We don’t have to cover everything right now, but like… While we’re having the conversation, you know?”
She ran her hands through my hair while I rubbed the small of her back. “I’m not sure if I wanna take your last name. Like, ‘Lily Winfield’ does sound super prissy in a way I kinda love, but also… My family’s legacy is really important to me. I’m not sure I’m willing to cut myself off from it in such a concrete, legal way.”
“That’s totally fine,” I said. “I honestly wasn’t expecting you to.”
“I don’t mind if you wanna introduce me to people as ‘Mrs. Winfield’ though,” Lily said. “Makes me feel all tingly.”
“You don’t have to have it legally changed, you know,” I pointed out. “Rose isn’t. She’s just going by Mrs. Duggan socially.”
“Hm. Intriguing,” Lily said. “Ms. DiGiacomo on the clock, Mrs. Winfield off the clock. Works for me.”
“Same here. Mrs. Winfield,” I said, growling it into her ear while my dick tented my pants. Fuck it- I wanted it like this. I wanted to take this woman and make her mine, wanted everyone to know it. Wanted her to know that I’d left my mark on her.
Lily’s response, naturally, was to nip my earlobe.
I shivered with pleasure. “God, Lily, my mom is here!”
She just giggled. “Your turn, by the way. Tell me something.”
“I…”
“C’mon. Out with it. Whatever it is, I can take it. Unless you’re a necrophiliac or something- that’s a dealbreaker.”
“Ha! No, uh… I think I want kids,” I said. “Not right now, obviously- we’re not actually married yet, and there’s still a lot up in the air, but when I picture us-”
She kissed me on the lips.
I blinked, then remembered how my wife preferred to communicate. “You want them too?”
She kissed me again.
“Awesome,” I grinned. “Is this a recent development, or-”
“I realized it earlier today. When I pictured us in ten years… We had a daughter.”
“A daughter,” I said, my brain conjuring an image of us holding a little girl, holding hands with her on each side as we walked on the beach together. The kid had some of my features, but her smile, her laugh, her energy- that was all Lily. “Okay. Cool. I am down to be a girl-dad.”
“And that is super hot, though if you also want a son I’m open to it,” Lily said. “Still: we’re not there yet. How about… How about in five years, we see if we’re both still on the same page? Figure out if we wanna adopt or do surrogacy or, hell, I’m open to fostering.”
“Works for me.”
Another kiss. God, I loved it when we did that.
“Anything else?” she said.
“Actually… Yeah. What you said earlier, about wishing we could’ve done it differently when we first met, wishing we could’ve both been a bit more honest with each other… Maybe that’s something we could work with.”
She raised an eyebrow. “What did you have in mind?”
“You said you like roleplay, right?”
Eyes wide, smile widening, she kissed me yet again. Oh yes, this was something we could indeed work with.
Comments
Helena Heissner
Two more chapters to go!!! And the ebook/paperback release will include a bonus epilogue chapter!
Gwen
this story is soooo good! I dont know if this was the final chapter but thanks for writing it!
