A Beginner's Guide to Gold Digging: Chapter 27

Author's Note: Welcome to the penultimate chapter! Been a wild ride, and I hope you're ready for the climax!

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A Beginner's Guide to Roleplay

Lily

Three Weeks Later

The garage was fixed, my office in the attic restored, my trans pride flag hanging from the wall behind me. I unbuttoned my flannel, letting my sports’ bra show as I started doing squats against my desk. My six-pack had, regrettably, softened during my convalescence, but I still wasn’t entirely sure if I wanted it back or not. Being buff was fun, but there was something nice about being delicate too. 

Footsteps ascended the wooden stairs of my loft, expensive loafers pounding on equally expensive lumber. I let myself drop into sub-mode, telling myself ‘okay, time to be Mrs. Winfield.’ And it felt so damn good. 

I savored the burn as I did a squat, and Crispin walked in on me and stared hungrily at the sight before him. 

I plastered on a sneer. “Take a picture, it’ll last longer.”

He pulled out his phone and snapped a picture. 

“Uh, excuse me? The hell was that?” I said, strutting over to him without buttoning up my shirt even a little bit. 

“When a beautiful woman tells me to do something, I’m inclined to do it,” Cris said. 

I gulped. “Well then I don’t know why you did that, because I’m not beautiful.”

He threw his head back and laughed. 

“What was funny about what I just said?” I glared, hands on my hips, standing only an inch away from him. 

“It’s funny because you’re the most beautiful woman I’ve ever seen,” Cris said in a deep-throated growl and a cocky smirk. He pushed forward, and I stepped back. 

“Then you haven’t seen many women, have you?”

“Actually, I’ve seen quite a lot of women. Known quite a lot, in the Biblical sense,” he said, continuing his forward charge. Suddenly I was leaning against my desk and standing between his legs. “And none of them looked like you.”

Giddy warmth pulsed through my breastbone, and I fought off a hungry smile. “And what do I look like?”

“You look like the woman I’m gonna marry.”

“Is that so? Feeling bold, are we?”

“Always. It’s the only way to get what you want in this world. Sometimes you just gotta reach for what you want and take it,” he said, and his hand found mine, fingers drawing circles on my palms and electrifying my skin in the process. 

“We don’t even know each other’s names,” I said. 

“I’m Crispin Winfield IV,” he said, fingers tracing up my forearm now. 

“Wow. That has gotta be the most textbook douchey rich guy name I’ve ever heard.”

“Well if it helps, my friends call me Cris.”

“Are we friends, then?”

“I certainly hope so. If we’re gonna get married, a rock-solid friendship is a good foundation for something that will last.”

“Again with the marriage talk,” I rolled my eyes as the pulsing in my chest grew stronger by the second. My nipples stiffened, and wetness started to build up between my legs. “You don’t know my name yet.”

“Then tell me your name, angel,” he said, fingers reaching my shoulder. 

“Angel?”

“I call it like I see it.”

“Well then… My name is Lily.”

“Lily,” he moaned, hands tracing my neck. “Perfect. Lily Winfield has a nice ring to it, don’t you think?”

“Sounds awfully prissy to me,” I said. 

“What’s wrong with that?”

“It’s not really me.”

He thumbed my chin, and my back arched as his legs spread further around me and the space between us vanished entirely. “Bullshit.”

“Beg pardon?”

“It’s absolutely you. I mean, just look at you. You’re prissy. High-maintenance. Soft. Girly. Delicate,” he said, lips against my ears. “It’s who you are.”

Fucking hell, I was so damn wet. High-pitched pants and groans sputtered out of my throat as arousal snaked up from my loins into the rest of my body. My hands drifted towards his chest, laying flat on his hard pectorals. “You don’t know me as well as you think.”

“On the contrary, I know you quite well,” he said, forehead pressed mine.

“What if I’m not who you think I am?”

“Then I’ll just have to fix that.”

“Fix what, exactly? Maybe I’m not attracted to you at all.”

His free hand found my breast, and he pinched a nipple poking through the thin fabric of my bra. “This tells a story that directly contradicts what you just said.”

I purred as a fresh spark of pleasure launched towards my heart. “I still… I still think you’re full of shit. There’s no way you actually like my frumpy ass.”

He took my hand in his and brought it between his legs. Eight inches of rock-hard piping filled my grip. “I’m sorry, what was that?”

I blushed furiously as yearning saturated my mind. “You can’t… You can’t do things like that, Crispin.”

“Things like what? Prove you wrong? Because I’m prepared to spend my life doing that. Every time you think you’re not beautiful, think I’m not into you or you’re not into me, I’ll prove you wrong. Every time you say I’m not gonna wife you up, I’ll prove you wrong. Because angel, I am gonna wife you up so fucking hard.”

“How hard?”

“Hard as my dick is in your hand.”

“Cris-”

“Called me Cris. Looks like we’re friends. That’s step one right there.”

“Step one on the path that leads to us… Getting married?”

“Goddamn right, angel.”

His mouth crashed into mine, his stubble tickling my smooth face and his tongue penetrating my mouth. He ran one hand through my hair, pulling out the scrunchy that held my ponytail in place and freeing my curls to flow down my back, while the other worked my breast. Happy, sexy chemicals pumped through me.

“I’ve never been with a man before,” I whispered into his mouth. 

“I figured you were gonna say that,” Cris whispered back as his hand lowered from my breast to my groin. His fingers gripped the zipper of my jeans and pulled it down, then reached inside and fiddled with my panties. “Fortunately for you, that’s what step two is for.”

“What’s step two?” I purred as he probed my front entrance through the fabric of my undies. 

“You really wanna know?” he said, now reaching past the undies and swiping his ring-finger over my wet lips. “You wanna know what I’m gonna do to you, angel?”

“Tell me,” I begged. 

His mouth found my ear again. “I’m gonna-”

And then he said those three little words, the ones he wasn’t supposed to say, the ones that I wasn’t supposed to want him to say, the ones that I’d wanted him to say from the second we met, as his fingers slid inside me and amplified my pleasure a thousand fold. 

“Ohhhh,” I purred, tumbling down deeper into sub-space. He found my clit and flicked at it, arching his fingers in a continual ‘come-hither’ motion that rubbed my vaginal walls and sparked against my g-spot. “No, no, you can’t, you can’t.”

“Bullshit,” he said, stroking and crooking and plunging into my wetness. 

“Stop,” I pleaded. Our actual safeword was ‘kusanagi-no-tsurugi.’ I’d been the one to come up with it after plowing through a few of Cris’ Japanese mythology books. He’d sported the most adorably overjoyed expression when I suggested it.

“I can’t,” he whispered. “You feel too good.”

My hands found his chest again, and I started unbuttoning his shirt and digging my fingernails into his hard, hairy chest. “If you don’t stop, I’ll hurt you.”

“Don’t threaten me with a good time.”

“I mean it!” 

“You’re worth the pain,” he said simply. 

I raked my nails over his skin, and for a split second he broke character and was so damn flustered again and I almost giggled. But he slipped back into dom-space just as fast and groaned with equal parts pain and pleasure as I carved red markings into his skin. 

He responded by putting another finger inside me, stimulating every single nerve ending and grinning with maniacal delight as I squirmed beneath his grasp. I dug my nails into his hips and bit his nipple, and that earned me a third finger. I reached below his waistline and tugged at his pubes, and this earned me a fourth. 

I moaned, “I can’t… I can’t take any more. Please no… No…”

“No what?”

“No…”

“You gotta tell me what not to do so I can do it, Lily,” he said, the fire in his eyes burning hotter than the day we’d truly first met. God, I’d thought he’d had horny-eyes all those months ago, thought he was unsubtle, but if anything… If anything, he’d been restraining himself even back then. This was what happened when you let Crispin Winfield IV off the leash. And apparently, this was what happened when you let me off the leash too… Or would that be on the leash? You get the idea. 

“More,” I begged. “MORE!”

“Anything for my angel,” he said. 

And just like that, his entire fist was inside me, opening up and wriggling all his fingers; and just like that, my first orgasm of the evening came crashing to the shores of my body, the dam bursting and flooding me with spectacular joy. My back finished arching, and he kissed me with hungry lust. His tongue in my mouth, his stubble tickling my cheeks, until he pulled away and put his finger in my mouth instead. It was still wet from me, and I tasted myself as I licked the fluids off his digits.

“Now, tell me: does that taste like someone who doesn’t like men?” he said. 

“I-I-”

“It tastes an awful lot like you loved it,” he said, lips on my neck, my cheek, my temple. 

“Y-y-y-”

“Say you loved it, Lily,” he commanded. 

“N-”

“Not taking no for an answer. Say you loved it. Say you love me.”

I pulled myself from his grip and dashed downstairs, zipping up as I fled the garage and was met with fresh pellets of rainfall. Today was the twenty-first. The equinox was upon us. How fitting that the season that brought us together ended as we renewed our commitment in the most ‘us’ way possible. How poetic that we ushered in a new season with a compromise we’d sorely needed, desperately wanted. How perfect that the first of the autumn rains hit, turning everything as wet as I was. 

The door was open, and I hurried inside and up the stairs. Void was asleep in his inside-hutch on the living room floor, and otherwise it was all clear for Cris and I to do whatever we wanted. Cris, with his longer legs and spectacular abs, was inside almost right away, chasing up the stairs. I could barely contain my giggles as he tore open the door to my room. 

“No,” I muttered. 

“I told you,” he said, closing the gap and pulling off my wet flannel. He tossed it to the floor, then pushed a wet lock of hair off of my forehead. “Not taking no for an answer.”

My lips trembled as he ran his fingers over them. “Please…”

“Please what?”

“Please don’t do this.”

“I’m sorry, angel. But I can’t stop. Not when you look this good. Not when you’re this perfect.”

“I’m not perfect.”

“You’re perfect for me,” he said. “Look how well I fit inside you.”

I slapped him. Obviously, I pulled the punch, but I still left an audible impact. He just laughed, the tent in his unzipped pants somehow growing larger. He grabbed me by the shoulders and threw me onto my bed, then reached underneath it and retrieved a rope. 

He held me down, tying my hands to the headboard, then parting my legs with his own. He tossed his shirt to the floor and wriggled out of his pants, the scars on his chest showing through his hair. The scars he’d gotten for me, the scars he’d gotten from me. They completed him: the dents in his shining armor that showed how much he was willing to fight for my love. His lean, tight muscles, broad shoulders, washboard abs, and long, toned legs completed the ensemble. And as his boxers fell to the ground, the piece de resistance, all eight inches of him, stood before me. His magic wand, ready to cast its spell on me, complete my transformation into Mrs. Winfield. 

“Say you want it,” Crispin said, positioning himself over me, the head of his dick tracing my vaginal lips and leaving me purring. “Say you want me. Because you’re all wet, and it isn’t just from the rain. Your nipples are hard, but it’s not from the cold. Your face tells a story that doesn’t match up with your words.”

One more act of resistance would help make it as good for him as possible. Perfect. He needed to enjoy this too. He needed to like it, so he wouldn’t feel guilt or shame like the both of us had known. I bit into my favorite spot on his shoulder, a near-permanent mark forming from all the times I’d sunk my teeth into it. 

“Mmmmm,” he groaned, and I wondered if he knew that was the sound I always made. Probably he did. He knew me so well. “I do so love it when they fight back.”

“Pervert,” I spat. “Douchebag. Manwhore.”

“You speak the truth, Mrs. Winfield.”

“I’m not-”

“Not with that attitude, you’re not. Now say you want me.”

“I-I-”

“Say it, Lily. Say it once, and I’ll make sure you never regret it as long as you live.”

“I can’t.”

“Why not?”

“Because I’m not supposed to want this,” I said, tears welling up behind my eyes as I tugged against the loose bondage of the rope. “This isn’t what I’m supposed to be.”

“Well it’s who you are, angel,” my literal dream-man said. “I think it’s high-time you learned to like it.”

He eased into me, just the head at first, swirling it around at the start of my canal. Ribbons of ecstasy twirled about it in my loins. He had me right where he wanted me, all tied up and unable to run away from this, from him, from myself, any longer. And it was exactly where I wanted to be. 

“Say it,” he said, kissing my chest, face between my breasts, kissing both orbs intermittently. “Say you want me. Say you’ll be Mrs. Winfield.”

“I… I…”

He pushed another inch inside me, my toes curling, my hands clenching and nearly slipping free of the ropes. He’d tied them in the gentlest way possible, made sure not to make them too tight. God, even when he was being naughty he was still so damn kind.  

“Say it,” he said, adding another inch, then another, then another.

“No,” I said defiantly.

“Why not?”

“Because you haven’t gone all the way in yet!” I said, adopting a whiny tone. “How will I know until you’ve given me everything you’ve got?”

He laughed. God, that sound. “You still don’t know? God, you’re such a bimbo.”

“I am not a-”

“Just a silly bimbo who thinks she doesn’t know what she wants, even when it’s blatantly obvious to anyone with eyes.”

“How dare you!”

“Just calling it like I see it. And what I see is a bimbo in need of education.”

“Then… Then hurry up and put it all the way in already! So I can know for sure!”

“Heh. Such a needy bimbo. But if my angel insists, I’m happy to oblige.”

He bucked his hips and entered me in his totality. I took him raw, feeling myself around him as he thrusted back and forth, back and forth, lifting upwards to drag his shaft against the roof of my canal, swirling to make sure every inch of me was properly stimulated. He kissed my neck and fondled my breasts and rubbed the mermaid tattoo on my thigh. I hooked my legs over his back, squeezing my thighs together and gripping his length as tight as possible. I pushed against him, taking him as deep as I could and as hard as I could. 

Time blurred. Rain fell outside, exploding against the ground and casting petrichor into the air. We fucked and fucked and fucked, marking each other, changing each other, saving each other. A new tidal wave headed for the shores of my body, the stormwall already destroyed and its remnants ready to be washed away forever. 

“I want it,” I breathed. 

“What’s that, angel?”

“I want it,” I repeated. “I want you. I want to be Mrs. Winfield. Dahling.”

And with the words out of my mouth, the wave crashed into the shore, and I screamed and screamed and screamed as pleasures greater than any I’d previously known consumed me on every level. He was the sea, and I was his ship, rocked and battered by his might but still riding atop him and letting him guide me where I needed to go. He came in time with me, exploding inside and painting my inner walls with his seed. It was the final ingredient in the elixir that unlocked my true self, completed my transformation into who’d always been and who’d I’d always fought against being. 

It didn’t matter if this wasn’t what I was supposed to be. It was what- who- I wanted to be. Who I was. He’d helped me realize it, but I was the one who took the plunge. 

His load spent, Cris breathed out and collapsed on top of me, kissing my forehead and then reaching for my bonds and untying me. He tossed the rope to the floor, kissed my cheek as I stroked his hair. He put his head atop my breasts, breathing in and out slowly. I kept stroking his hair, holding him tight as we basked in the warm afterglow together. 

We’d formalize it eventually, but as far as I was concerned, I was Mrs. Lily Winfield, now and forever.