A Beginner's Guide to Gold Digging: Chapter 14

Author's Note: Happy Pride Month! Hope you're hungry, because you're getting multiple chapters this week!

A Beginner's Guide to Taking the Plunge

Lily

I’d expected something a bit like Crispin’s family house in the city from their beach house. Based on the sheer amount of praise he had for the place, logically, it must’ve been as ostentatious and huge and over-designed as their main house. And it was nice, incredibly nice, and very large, but there was something much humbler about it than what I’d pictured. 

There was a mudroom off to the side when we entered, but no chandelier, no stained glass, no fancy Persian carpet, no crown molding, no paintings on the walls or antiques sitting atop marble stands. The place was… Just a house, really. Hardwood floors with a deep brown finish, a plain stairwell leading up to the second and third floors, framed photos on the walls. 

I looked at them as I walked by: they were all of Crispin and his family. Him, his father, Lydia and Priscilla, and… Presumably his birth-mother. She was red-haired, with bouncing curls flowing down her back in every photo and alabaster skin lightly freckled. She was in all of them, always holding one of her kids. Most often, it was Crispin.  

The photos seemed to stop when he was around five years old, by the look of him. God, no wonder he revered his mom so much: she died when he was so young he hadn’t been able to develop any kind of negative feelings towards her. To him, she was this saintly woman who loved him and his older sisters to pieces and then was taken way too young. It was kind of sweet, in a tragic way, though I couldn’t help but wonder if it was entirely healthy. 

“You can pick out whatever bedroom you want,” Crispin said. “I’m just gonna take my old one on the top floor. There’s a full bathroom on each floor as well, so we won’t have to share.”

“I mean… I don’t mind sharing.” The words leapt from my mouth, propelled by new feelings I still hadn’t fully accepted.

He looked at me blankly. He blinked. Then he said, “Yeah, you do.”

I grimaced. “Yeah, I do,” I responded, since that was what he was expecting, since that was what I was supposed to say, since this was who I was supposed to be. 

“I’ll let you get settled in,” he said, looking away from me. Of course he was looking away- I’d made it weird with my weird words and my weird feelings and my weird everything. I’d look away from me too. “And, uh, I’m sorry about all this.”

“Cris, there are worse fates than spending a long weekend at a beautiful beach house with someone I love hanging out with,” I said gently. 

His cheeks went red and his eyes went wide. Dammit- now I was making him uncomfortable! “Uh… Right. I’m gonna go get changed and then take a swim.”

“Oh… Okay!” I said. “I’ll join you in a little bit.”

“Cool,” he said before heading up the stairs. 

I watched him climb them, and I… God help me, I checked out his ass! It was firm and tight by the look of it, and his jeans hugged them in a way that turned the gears inside my mind. Made me want to take a fistful of it and wrap myself around him, kiss his neck and cheeks and mouth, straddle him, fist his shirt and guide his hands to my boobs. I imagined how his hands, rough and soft at the same time, would feel around the globular flesh, pinching my nipples while he buried his tongue in my mouth-

He left my line of sight, and I kept standing there, mouth hanging open, eyes wide, nipples erect, confusion and fear overwhelming my every brain cell. 

Finally, as my head swam through the ocean of these strange, terrifying desires, I mounted the stairs and began the climb. I found a room on the second floor with a simple queen-sized bed under a tan comforter. A dresser and a nightstand and a small closet and a full-sized mirror brought the place together within the confines of the light blue walls. 

I set my bag on the floor and fished out my bathing suit- or at least, what passed for a bathing suit for me: a black sports’ bra and a pair of black basketball shorts. Ugh, I couldn’t wait to get the big operation and finally be able to wear bikinis. I had the boobs for them and the legs for them and I knew I’d look wicked cute… Just not yet. 

For now, though, this would have to do. 

I shut the door, then stood in front of the mirror. This dress… It looked good. Really good! I’d been reluctant to wear it when Rose picked it out for me, but it was cute and stylish and sexy all at once. The color looked great on me, contrasting my brown hair and my brown eyes perfectly with its bright, warm hues. It just looked so… Made me feel so… So freaking girly! Like warm serenity flowing through the ocean of my mind and filling me with bliss and comfort. I felt more like myself wearing this dress than I ever had in my baggy hoodies and ratty sweats. 

Part of me wanted to think that felt wrong, that I was betraying myself, that I was selling out, but… I knew that wasn’t true. I don’t know if I’d always been a girly girl underneath it all, but the changes I’d been making lately, the steps I’d taken towards becoming one… Dammit, it felt right. The only thing I didn’t like about how all this looked on me was that I wasn’t wearing any makeup, and the fact that THAT was my main objection spoke volumes. 

Maybe… Maybe this was what I wanted. Maybe this was the real me. Nobody had forced me into it. I’d volunteered myself for feminization every step of the way.

I did a twirl, feeling the skirt spin around me and watching it hoop out as I turned. God, it was so fun and cute and silly and pretty and… And that was what I wanted to be. That was who I wanted to be. So there I was. A girly girl, at a beach house with the man who’d put an engagement ring worth more than anything I owned onto my finger. If you’d gone back in time a year and told me this was my future, I’d have gone apoplectic. And yet here, now… I was happy. 

Reluctantly, I wiggled out of my sundress and put on my swimming outfit. 

As I walked out the back door of the house and onto the hot sand with a towel in hand, I braced myself. If what I was feeling for Cris was real and not just some kind of bizarre confusion stemming from my having had so few guy friends (and based on how I’d felt last night while caring for him, as well as the return of those feelings when I woke up in his arms with his stiffy pressing into me (not to mention that warm flustering I’d enjoyed when he said I looked gorgeous in the dress), I was unfortunately facing the distinct possibility that it was very real), I needed to steel myself. We were at a beach. He was likely shirtless and soaking wet, but I simply had to keep my wits about me and shove down any feelings I was getting tortured by until they withered and died from atrophy. Then everything would go back to normal for Crispin and I, and I could pretend nothing weird had ever happened, that I’d never experienced boy-liking at all and there was nothing wrong with me and I didn’t have to rethink my entire identity based around some stupid, warm, intoxicating sensations that went through me while I was touching him. It was all fine, fine fine fine-

Fine as fuck! Holy shit! 

Those were the next words that popped into my brain as I saw Cris walking out of the water in a tight pair of emerald-green swim trunks that matched his eyes perfectly, soaking wet with seawater that dripped from his chest hair and off his facial stubble. The trunks looked like they were a size too small, and the result hugged his package in a way that reinforced something I’d learned twice-over now: Crispin Winfield’s dick was ENORMOUS.

My nipples erected once more, and the warmth washed over me from my heart to mind to my stomach to my nether-regions. He was the tide, pulling me towards him, wanting to carry me away and guide me to places I’d never seen before. I wanted to get lost in him. I wanted him all around me. I wanted him to fill me up and overwhelm me so damn much I forgot who I was before. Because I WAS starting to forget who I was before I met him. And the really scary part was I liked this new me that I was becoming much better. 

He was like that dress. He fit perfectly, made me feel beautiful in a way I’d never experienced erstwhile. I hadn’t expected to like him this way. I hadn’t expected to be someone who would like him. And yet, here I was. A girly girl, at a beach house with a man who’d put a diamond ring on her finger. A man who she… 

A man who she was attracted to. 

Did I mention I was holding a tube of sunscreen when I saw him, and as he approached me I reflexively squeezed it and released a massive squirt of the liquid onto the sand below my feet? Because that also happened. 

God, why? Why did this have to happen to me?! There were no indications of this! It wasn’t like with the trans thing where I’d kinda known since I was at least eleven that I hated being a boy. There were no signs!

… At least, I didn’t think there were any. 

No, there definitely weren’t. This had come completely out of nowhere. It must have. There was no way I’d felt this before and just… Ignored it. How could I ever ignore something that felt this good, this right?

He walked up to me and looked me up and down, probably mentally comparing me to all the hotter, girlier, straighter, more cisgender girls he’d been with hithertofore. I’m sure I came up lacking. I mean, obviously. 

“Hey,” he said, his voice low and full and smooth.

“Hey,” I said in my softest, breathiest voice. God, this man was changing me. Not on purpose, not with any ill-intent. But his proximity was reshaping me, rearranging me, remaking me. And I loved it. “How’s the water?”

“Freezing,” he smiled. That fucking smile. If mine lit up the room, his warmed the whole planet. I felt good around him. Safe. Loved, even if it wasn’t in the way… The way I was starting to think I wanted. 

“That a good thing?”

“For me it is.”

“Well, it’s probably not that cold,” I laughed. 

“Care to test that theory?”

“I do indeed,” I said, walking towards the beginnings of the water, dipping a toe in. “Oh, God! That’s fucking freezing!”

He laughed as he said, “You barely even went in!”

“It’s… It’s… It’s cold,” I whined. 

“What’s the matter? I thought you were a tough girl, angel.”

“I am,” I pouted. 

He followed me into the ankle-deep ice-water, still laughing, still with that infuriatingly cocky smirk he made look good in the most annoying way possible. He put his wet hand to the small of my back, sending a tingling up my spine that altered my brain chemistry. He nudged me forward into the water, not pushing me, just… Guiding me. 

There was nobody here but us, so I decided to let him. I trusted him. 

The water rose to my knees, my thighs, my waist. I guided his hand from my back to my waist, and leaned against him, reveling in his body heat and the tickle of his hair and the musky man-scent of his heightened by the saltwater. 

“How does that feel?” he said softly, his breath on my skin and his words reverberating in my bones. 

“It’s… It’s not bad,” I said reluctantly. “But it’s still cold.”

“There’s only one way to fix that, you know.”

“Turn around and run away?” 

“‘Fraid not, angel. You gotta take the plunge.”

“I- I-”

“It’s the only way you’ll get used to it.”

“I’m scared,” I said into his chest. 

“That’s okay. I can take it with you, if that would help.”

“It… It would help a lot, yeah,” I said, reminding myself that we were still talking about the ocean. 

“Okay. Put your arms around me?”
… Were we still talking about the ocean?

I did as he asked, and not for the first time, I found that I really liked doing what he told me to do. He held me tight, looking down at me as my breasts pushed against his bare chest. Warm, steady, solid, safe. And just like that morning, our faces were so close together. 

“Ready to take the plunge?” he asked. 

I nodded. And those thoughts started entering my head again, those thoughts that scared me, those thoughts that breathed new life into me: kiss him kiss him kiss him-

He pulled me down into the water as a wave washed over us, submerging me in the frigid brine of the Atlantic. He held me tight, never taking his eyes off me even as the shock of being underwater with him slammed into me. I felt like the old me was being washed away, dissolved by the tide like some kind of enchantment broken by running water. And what remained, what would still remain when I broke the surface, was a new me. 

Kiss him kiss him kiss him-

However, he chose that moment to scoop me up into his arms and carry me back above the surface. I was in his arms, held like a bride as a rush of clean air entered my lungs. The sun shone over us, sparkling off the water and off his eyes and he was so damn close and kiss him kiss him kiss him-

“How was that?” he asked, voice resonating with low-pitched warmth.

My face moved before I could stop myself, and my lips pressed against his stubbled cheek. He flinched, but the look on his face… I couldn’t quite read it, but it didn’t exactly look displeased. “What was that for?” he said. Genuine confusion- that was it. 

“Just… A thank you, for saving me last night,” I said, reveling in his fingers pressing into my back and shoulders. “I was in real trouble, and you saved me. So good job.”

“Oh, uh… Well, you’re welcome then,” he said, eyes half-hooded. 

“I’m sorry, I should’ve asked first before I did that-”

“It’s fine,” Cris said. “I really don’t mind one bit.”

“Okay,” I nodded. “And I’d also say thank you for getting me all wet, but you probably hear that from girls all the time.”

He laughed, and the low rumbling that came with it made me very happy, feel very protected and wrapped up in him. “I mean, it wouldn’t be the first time.”

“Hm, fair enough,” I said. 

“Wanna take another dip?” he asked. 

It felt nice, being under the water with him, so I nodded. 

And we took the plunge once more. 

We spent hours in the water, swimming, splashing each other, having races, riding waves. I’d honestly forgotten how much I loved the beach, and being there with him made it all the more magical. And as my arms and legs grew tired, he carried me to shore in his arms. Didn’t ask, just scooped me up and held me, and I rested my head against his shoulder while he brought us onto the sand. 

He set me down on a towel he’d spread out next to a tote bag, and then he kissed my forehead. The shock of it made my heart skip a beat, made me want more and more and more. “What was that for?” I giggled. God, there it was again. 

“Just… Wanted to thank you for taking care of me last night,” he said, looming over me. I tried my best to look in his eyes, but my gaze was continually drawn towards the bulge in his shorts. I really hope he didn’t notice it. 

“Yeah, no problem,” I said. “I’ll play nurse for you anytime.” Oh Goddammit, I did it again!

He simply looked me up and down with a gentle smile, then sat next to me and reached into his tote bag. “Gonna read for a little bit,” he said as he pulled out a Wonder Woman comic. 

“Wait, is that-”

“The last volume of the run you recommended to me, yeah,” Cris said. “The 2000s one.”
“You… You’ve read the rest of it?”

“Yup, and I picked up the writer’s 2016 run too,” he said. “The way you talked about it sounded cool, so I decided to give it a shot.”

“That… I mean… What did you think?” Didn’t you call them ‘low art’ when I told you about them?

“I loved it,” he said. “Great stuff. The mythology and espionage- fucking epic.”

“You… Sorry, I just can’t believe you started reading comics. It… It didn’t really seem like your thing.”

“Only because I’d never tried them before,” he shrugged. “You’ll never know if you like something until you try it.”

“Right,” I nodded, dying inside. 

“And besides, I wanted to understand you better,” he smiled. 

That was… That was about the sweetest thing I’d ever heard. Maybe it was all the times Olivia had called my interests stupid, my passions childish or worse, boyish. Maybe it was all the other times I’d heard a date roll their eyes or cringe when I started talking about my hobby. Or maybe it was just that it was him. Either way, a new image stampeded over my fragile consciousness: us holding hands as we walked into a comic shop together, cuddling while we read together, kissing-

Oh God. It’s not just physical, I realized. I wasn’t just attracted to Crispin Winfield. I LIKED him. I had a crush on him. I wanted to go on dates with him and I wanted to be cute and flirtatious with him and I wanted to swoon over him when he did sweet things for me and oh God, why?! How could this happen to me?!

“Lemme know if you’ve got any more to recommend,” he said as he leaned back and opened the comic. 

“Okay,” I whispered as my eyes traced his body up and down and my mind begged me to lean into him and read with him. 

I needed to reassert equilibrium. This was wrong, all kinds of wrong. I looked around for a girl, any girl, to gawk at, just reassure myself I hadn’t been fully converted when I wasn’t looking. A few dozen yards down the beach, I found one: a tall, leggy blonde in a bikini that left little to the imagination. Fucking hell, those breasts, those cheekbones, those shoulders, those legs- I licked my lips as I drooled over her soaking wet form. 

Okay, I still liked girls. Thank God. Maybe Crispin was just… A fluke. A passing fancy born of forced proximity and strong social chemistry. An exception to my otherwise unblemished homosexuality.

Aaaaannnndddd then a guy lumbered out of the ocean next to her, a beautiful bear with short black hair and bronze skin. His bathing suit was a full-on rainbow-colored speedo that made his package look massive, while his hairy chest and tight tummy offered an enticing view. 

I chewed my lower lip as I imagined myself as the meat in the proverbial sandwich of those two. So no, Cris was apparently not a fluke. Fuck.

“You should go talk to her,” Crispin said. 

“Hm? Who?” I said, trying to avoid looking at him. 

“That girl you’re drooling over,” Cris said. I stole a quick glance and found that he wasn’t even looking away from his comic. “Go tell her she’s pretty.”

“B-but she’s with someone- what if that’s her boyfriend?”

“He’s wearing a pride flag as a swimsuit, there is no way that he’s her boyfriend.”

“Uh- I just-”

“Look, Lily, you’ve got needs. I understand. And it’s just us here, so there’s no risk of my family catching you. Go lez that girl up and get laid. Bring her back to the beach house tonight if you want, just remember to put a sock on your doorknob.”

“A-are you sure?”

He finally looked at me, and those eyes, oh God those eyes… “Yeah,” he nodded. “I’m sure.”

I gulped, but I found myself nodding back and getting up and going over to the leggy blonde. I didn’t want to. I was supposed to want to. She was devastatingly hot, if maybe a bit more femme than I usually went for. But I didn’t want to. I wanted to lay next to Crispin. 

I sighed as I finished my approach. “Hi,” I squeaked out. 

“Hi,” the blonde said, eyeing me up and down in a very suggestive way. 

“I’m Lily.”

“Nice to meet you, Lily,” the blonde said while her very handsome bara friend covered his laughter with his hand and walked away. “I’m Sandra. And I must say, it’s very nice to meet you.”

“You as well,” I said with little enthusiasm in my voice. 

“Oh, what’s wrong? What’s a beautiful lady like you got to be upset about?”

I stared forward, dead-eyed and slack-shouldered, before it all started spilling out: “I’m in a fake engagement to a guy I thought I wasn’t attracted to but now I am and I’m having an existential crisis because I’m realizing I might actually be bisexual when I thought I was gay and it scares the shit out of me but it doesn’t matter in the first place because he’s not into me like that and he told me to come over here and hit on you because he wanted me to have some fun but all I want is to spend time with him and now I hate myself because I can’t even do what he wants me to do even though it’s something I already like-”

Sandra started backing away slowly after about five words. Her flirtatious smile never wavered, even as she said, “Yeah, uh, have fun with that. Sellout.” And as she caught up to her gay friend, I heard her say, “God, another one bites the dust, I swear.”

My jaw dropped as the sting of her words pierced me. After the two of them faded from my line of sight, however, I just turned around and walked back to Crispin. 

“No dice?” he asked, not looking up from his comic. 

“She wasn’t interested,” I said, voice hollow. 

“Oh well. Next time, then,” Crispin shrugged. 

“Right. Next time,” I said.